1 marpat basics (markush structures). 2 where did the term markush come from? in 1923 dr eugene a...

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MARPAT Basics(Markush Structures)

2

Where did the term Markush come from?In 1923 Dr Eugene A Markush filed a patent application in the United States concerning a method of preparing pyrazoline dyes that could be used for wool or silk.Claim 1 of this application read:

…coupling with a halogen substituted pyrazolone a diazotizated unsulphonated material selected from a group consisting of aniline, homologues of aniline and halogen substitution products of aniline.

The claim was challenged as being too unspecific. On appeal the US Commissioner of Patents ruled on the propriety of such claims. The patent was granted in 1924 as US 1,506,316.

Introduction

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Markush StructuresMarkush structures in patents condense an entire set of implied substances into a single representation using real atoms and R groups.

R1 = alkyl of 1-6 carbon atoms or alkenyl of 2-6 carbon atoms R2 = alkyl of 1-6 carbon atoms R3 and R4 = H or alkyl of 1-6 carbon atoms

R2

R1

R3

R4

Introduction

4

Introduction

Prophetic substances, e.g., those encompassed by the Markush structures in patent claims, are not indexednot indexed in CAPLUS and REGISTRY (if missing).

5

Introduction

Prophetic substances, e.g., those encompassed by the Markush structures in patent claims, are not indexednot indexed in CAPLUS with RNs, even if they are indexed in REGISTRY.

6

Introduction

But any patent containing Markush structures has examples But any patent containing Markush structures has examples correlated to the Markush structures.correlated to the Markush structures.

7

R

R’

R = pyridyl ring (isolated/embedded)

R' = carbon chain of any length

No additional fusion on the polycyclic ring

Additional substitution allowed at all open sites

What has been reported on compounds with the following structural characteristics?

Introduction

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=> fil reg=> Uploading C:\Program . .

=> d

N

N

N

N

O

Ak

Introduction

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=> l1 fullFULL SEARCH INITIATED 04:51:57FULL SCREEN SEARCH COMPLETED - 100.0% PROCESSED 4 ITERATIONS SEARCH TIME: 00.00.01 L3 0 SEA SSS FUL L1 => fil marpat

Introduction

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=> l3 fullFULL SEARCH INITIATED 04:52:43FULL SCREEN SEARCH COMPLETED - 100.0% PROCESSED 139 ITERATIONSSEARCH TIME: 00.00.02 L5 3 SEA SSS FUL L1

Introduction

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MARPAT Overview

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• The MARPAT database– produced by CAS and available only on STN,– contains structural representations of the

Markush structures that appear in patent claims.

• A Markush structure condenses a set of implied substances into a single representation.

• Only Markush structures are searchable in Only Markush structures are searchable in MARPAT.MARPAT.

MARPAT Overview

13

• The same types of structure queries can be searched in REGISTRY and MARPAT.

• MARPAT queries may contain:– Specific atoms and shortcuts– Variable groups– G-groups– Specific bonds– Unspecified bonds– Isolated rings– Ring/chain nodes– Not ring/chain bondsNot ring/chain bonds

MARPAT Overview

14

In Marpat are available the following structure searches:

SSS CSS

Sample Full Range Subset

MARPAT Overview

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Search Scope Iterations Answers Minutes Online SAMPLE 2,000 50 5 Subset SAMPLE 2,000 50 5 Online FULL 100,000 100,000 30 Subset FULL 100,000 100,000 30 BATCH FULL 150,000 150,000 180 Online RANGE 100,000 100,000 30 Subset RANGE 100,000 100,000 30 BATCH RANGE 150,000 150,000 180

MARPAT Overview

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MARPAT OverviewYears of Coverage Currently 1988+ ;

When addition is complete, 1961+

Update Frequency Weekly

Markush Structures Over 640,000 Markush structures in MARPAT Over 27M small molecule structures in REGISTRY

Source of Data 50 patent-granting authorities

Patent Records 247,000 (in MARPAT)5.1M (in CA)

Bibliographic Data Displayable; Searchable in CAPLUS

SDI availability Yes

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MARPAT Enhacements

Approximately 40,000 Markush structures derived from Institute National de la Propriete Industrielle (INPI) data have been added to MARPAT from the pre-1988 time period. Additional records back to the early 1960s will continue to be added during 2006.

MARPAT does not have File Segments, but each INPI Markush structure includes the following note: “Record may include structures from Record may include structures from disclosuredisclosure.”

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MARPAT Enhacements

=> fil marpat => Record may include structures from disclosureRecord may include structures from disclosureL1 40359 RECORD MAY INCLUDE STRUCTURES FROM DISCLOSURE (RECORD(W)MAY(W)INCLUDE(W)STRUCTURES(1W)DISCLOSURE)

=> sel l1 1-10000 anL2 SEL L1 1-10000 AN : 10047 TERMS

=> fil hcaplus => l2/dnL5 10047 L2/DN

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MARPAT Enhacements

=> l5 and polymers/cc=> l5 and polymers/ccL6 293 L5 AND POLYMERS/CCL6 293 L5 AND POLYMERS/CC TI Preparation of amides from nitriles and amines TI Olefinic benzocyclobutene polymers and processes for their preparation TI N-tert-alkyl-n-sec-alkyl secondary amine compounds TI N-substituted carbamoyl lactams TI Catalysts for the polymerization of olefins

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MARPAT Enhacements

=> l5 and alloys/cc=> l5 and alloys/ccL7 46 L5 AND ALLOYS/CCL7 46 L5 AND ALLOYS/CC TI Benzoylalamine as corrosion inhibitor for aqueous systems TI Dicyclopentadiene dicarboxylic acid salts as corrosion inhibitors TI Copper etching process and solution

TI Alkaline cleaning bath for aluminum

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MARPAT Enhacements

=> d l1 1, 40359 an AN 2003:785279 HCAPLUSDN 139:283282DN 139:283282 Correction of: 104:177615 Correction of: 104:177615 AN 1912:8178 CAPLUSDN 6:8178DN 6:8178OREF 6:1274g-i

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MARPAT Enhacements

1CI 1907 v1 6CI 1957 V51 1908 v2 1958 V52 1909 v3 1959 V53 1910 v4 1960 V54 1911 v5 1961 V551961 V55. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4CI 1937 v31 1938 v32 12CI 1987 V106 and V107 1939 v33 1988 V108 and V109 1940 v34 1989 V110 and V1111989 V110 and V111

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Feature Notes

Source of the Markush structures

Structure from claim – or disclosure if no Markush in the claims

Additional details from disclosure

Search access points

Substructure seraching

Text terms from MPL, NTE, and other text fields associated with the Markush structure

CAplus information Displayable, not searchable

MARPAT Overview

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• All MARPAT records are also in CAplus.All MARPAT records are also in CAplus.

• They have the same Accession Number (DN).

• CAplus information can be displayed in MARPAT.

MARPAT Overview

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AN 133:290336 MARPATTI Coordination compounds with ligands of a nitrogen heterocycle and Organic electroluminescent device using these complexesIN Kim, Kong-Kyeom; Son, Se-Hwan; Kim, Ok-Hee; Yoon, Seok-Hee; Bae, Jae-Soon; Lee, Youn-Gu; Kim, Hyo-SeokPA LG Chemical, Ltd., S. KoreaSO PCT Int. Appl., 47 pp. CODEN: PIXXD2DT PatentLA EnglishIC ICM C07F001-00 ICS C07F003-00; C09K011-06; H05B033-14CC 78-7 (Inorganic Chemicals and Reactions) Section cross-reference(s): 28, 73

o o o

BIB information.

MARPAT Overview

/DN in CAPlus

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o o oFAN.CNT 1PI PATENT NO. KIND DATE APPLICATION NO. DATE ------------- ---- ---- --------------- -----PI WO 2000058315 A1 20001005 WO 2000-KR289 20000330 W: CA, CN, JP RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SEPRAI KR 1999-11160 19990331 AB Disclosed are new coordination compds. having light-emitting and electron-transporting

o o oST zinc benzothiazole deriv complex prepn electroluminescent deviceIT Electroluminescent devices (zinc benzothiazole deriv. complex as electron- transporting material for)IT 7429-90-5D, Aluminum, complexes with nitrogen- contg. heterocycles

o o o(continued on next page)

Caplus subject and CAS RN indexing.

CAplus abstract.

BIB information includes patent family members.

MARPAT Overview

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IT 103-72-0, Phenyl isothiocyanate 105-53-3, Diethyl malonate 122-39-4, Diphenylamine, reactions 557-34-6, Zinc acetate 1076-38-6, 4-Hydroxycoumarin 1677-46-9 RL: RCT (Reactant) (reactant for prepn. of zinc benzothiazole deriv. complexes as electron-transporting material for electroluminescent devices)RE.CNT 6RE(1) Chen, C; US 6020078 A 2000 CAPLUS(2) Lg Chemical Ltd; WO 9837736 A1 1998 CAPLUS(3) Lg Chemical Ltd; WO 9963023 A1 1999 CAPLUS(4) Sanyo Electric Co Ltd; EP 0743809 A2 1996 CAPLUS(5) Shinko Electric Industries Co Ltd; EP 0801518 A2 1997 CAPLUS(6) Xerox Corporation; EP 0862353 A2 1998 CAPLUS

o o o

Citations from the patent.

MARPAT Overview

RNs, not searchablenot searchable.

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MSTR 1

G1 = 7 / (SC 26 / 40 / 57 / 74 / 95 / 104 / 113 / 122 / 131)

(continued on next page)

G5G1 G8

7

NG2

G4

26

G2

N 40

G2

N

57

G2

N

74

G2

N95

G2

NN

N

104

G2

NN 113

G2

N

Markush structure from the patent claims.

MARPAT Overview

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G2 = CH2 (SO) / O / S / Se / 8

G3 = alkyl (SO) / aryl (SO)G4 = R<TX "moiety to form aromatic or heterocyclic ring">G5 = 15 / (SC 140 / 153 / 166 / 182 / 195 / 211 / 227 / 253 / 265 / 277 / 289 / 301 / 314)

o o oG6 = O / S / 20

G7 = R<TX "moiety to form aromatic or heterocyclic ring">G8 = R<TX "metal"> / (SC Li / Be / Zn / Mg / Ga / In / Al) MPL: claim 1 NTE: as complex with G8

122

G2

N

N

131

G2

NS

8N G3

15G6

O

G7

HO140

G6

OHO153

G6

OHO

Me

166G6

OHO

20N G3

MARPAT Overview

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• Searching both MARPAT and REGISTRY enhances substructure search recall of the patent literature by retrieving both– Specific compoundSpecific compound matches, from REGISTRY– Prophetic compoundProphetic compound matches, from MARPAT

• Techniques for conducting a substructure search in MARPAT are similar to those used in REGISTRY.

MARPAT Overview

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Specific Substances, from a patent, are indexed in Registry, and in CAPlus, with a RN.

MARPAT Overview

For patent documents, the following substances are

indexed with a RN.

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From examplesFrom examples

From tables (disclosure)From tables (disclosure)

From claims when a MarkushFrom claims when a Markush structure is exactly structure is exactly defined (1980 only)defined (1980 only)

MARPAT Overview

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CAS RN 191411-58-2

(CH2)4 OEt

OEt

P

O

S

NH2

Compound indexed from Example 1

MARPAT Overview

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CAS RN 191411-86-6

PO3H2S CH2 CH2 CH

OH

CH

Compound indexed from Claim 4

MARPAT Overview

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AN 127:62046 MARPATTI Preparation of arylthioalkyl- and arylthioalkenylphosphonic acids and derivatives as herbicides

IT 191411-58-2P 191411-61-7P 191411-63-9P 191411-65-1P 191411-67-3P 191411-69-5P 191411-71-9P 191411-73-1P 191411-74-2P 191411-75-3P 191411-76-4P 191411-77-5P 191411-78-6P 191411-79-7P 191411-80-0P 191411-81-1P 191411-82-2P 191411-83-3P 191411-84-4P 191411-85-5P 191411-86-6P 191411-87-7P 191411-88-8P 191411-89-9P 191411-90-2P 191411-91-3P 191411-92-4P 191411-93-5P 191411-94-6P 191411-95-7P 191411-96-8P 191411-97-9P 191411-98-0P 191411-99-1P 191412-00-7P RL: AGR (Agricultural use); SPN (Synthetic preparation); BIOL (Biological study); PREP (Preparation); USES (Uses) (prepn. as herbicide)

CAS RN 191411-58-2 from Example 1

(CH2)4 OEt

OEt

P

O

S

NH2

CAS RN 191411-86-6 from Claim 4

PO3H2S CH2 CH2 CH

OH

CH

MARPAT Overview

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• PropheticProphetic substances, e.g., those represented by Markush structures in patent claims, are not generally indexed in CAplus.

• Markush structures provide structure-searchable access (ONLYONLY) to the substances covered by patent claims and disclosures, such as the prophetic substances.

• Only patents with Markush structures are indexed in Marpat

MARPAT Overview

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Each specific compound generated based on the Markush variables is not indexed in CAplus.

MARPAT Overview

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MSTR 1

G1 = H / F / Cl / Br / IG2 = NH2 / OH / alkylcarbonyloxy<(1-4)> / OCHO /OCOPhG3 = S / S(O) / SO2

G1

G2

9G3 G4 11P

O

G5

G9

MARPAT Overview

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G5 = OH / 26 / 32

G6 = alkyl<(1-4)> / 28

G8 = alkali metal atom / NH3 /

R<TX "organic ammonium cation">

G4 = CH2CH2CH2CH2 / 13-9 16-11 / 17-9 20-11 / 21-9 24-11

13HC CH CH216CH2 17H2C CH CH 20CH2 21

H2C CH2 CH 24CH

26O G6 32OH G8

MARPAT Overview

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• Consider searching both REGISTRY and MARPAT when

– It is important to comprehensively search all structural possibilities covered in patent claims

– REGISTRY searches turn up no hits

– It is important to cover "incompletely defined" compounds (/ IDS) that might not match your query specifications in REGISTRY

MARPAT Overview

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Search Question:

What has been reported on compounds with the following structural characteristics?

R1 = pyridyl ring (isolated/embedded)R2 = carbon chain of any lengthNo additional fusion on the polycyclic ringAdditional substitution allowed at all open sites

MARPAT Overview

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MARPAT Overview

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chain nodes :20 21 ring nodes :1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 chain bonds :2-21 3-20 ring bonds :1-2 1-6 2-3 3-4 4-5 5-6 5-7 6-9 7-8 7-10 8-9 8-13 10-11 11-12 12-13 14-15 14-19 15-16 16-17 17-18 18-19 exact/norm bonds :2-21 3-20 5-6 5-7 6-9 7-8 7-10 8-9 8-13 10-11 11-12 12-13 exact bonds :1-2 1-6 2-3 3-4 4-5 normalized bonds :14-15 14-19 15-16 16-17 17-18 18-19 Match level :1:Atom 2:Atom 3:Atom 4:Atom 5:Atom 6:Atom 7:Atom 8:Atom 9:Atom 10:Atom 11:Atom 12:Atom 13:Atom 14:Atom 15:Atom 16:Atom 17:Atom 18:Atom 19:Atom 20:CLASS 21:CLASS 22:CLASS

MARPAT Overview

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=> FILE REGISTRY=>Uploading mar1.strL1 STRUCTURE UPLOADED

=> D L1L1 HAS NO ANSWERSL1 STR

(continued on next page)N

N

NO

N

Ak

MARPAT Overview

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=> S L1 SSS SAM

L2 0 SEA SSS SAM L1

=> S L1 SSS FULL

L3 0 SEA SSS FUL L1

The REGISTRY search turns up no substances.

MARPAT Overview

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• "No hits" in REGISTRY means that no substances represented by the structure query were indexed in CAplus from 1967-present (or in CAOLD from the 1957-1966 Molecular Formula Indexes).

• The substance of interest could be encompassed in the prophetic substances covered by the Markush structure in a patent claim.

MARPAT Overview

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=> FILE MARPAT

=> S L3 SSS SAMSAMPLE SEARCH INITIATED 13:55:20 FILE 'MARPAT' SAMPLE SCREEN SEARCH COMPLETED - 7 TO ITERATE100.0% PROCESSED 7 ITERATIONS 0 ANSWERSSEARCH TIME: 00.00.03FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE**PROJECTED ITERATIONS: 7 TO 299PROJECTED ANSWERS: 0 TO 0

L5 0 SEA SSS SAM L1


Searching MARPAT for prophetic substance matches

Use a SAMPLE search in MARPAT to verify the search will run to completion.

MARPAT Overview

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=> S L3 SSS FULLFULL SEARCH INITIATED 13:54:52 FILE 'MARPAT' FULL SCREEN SEARCH COMPLETED - 89 TO ITERATE100.0% PROCESSED 89 ITERATIONS 3 ANSWERSSEARCH TIME: 00.00.09

L4 3 SEA SSS FUL L1

=> D 1-3 BIB ABS

L6 ANSWER 1 OF 3 MARPAT COPYRIGHT 2000 ACSAN 127:293247 MARPATTI Preparation of pyrrolopyrazines as GABAa receptor ligandsIN Blum, Charles; Hutchison, AlanPA Neurogen Corp., USA

o o o

The MARPAT search retrieves 3 patents.

HELPFUL HINT:HELPFUL HINT: Search the L-number resulting from the REGISTRY substructure Search the L-number resulting from the REGISTRY substructure search to take advantage of a lower, “extended” search fee in MARPAT.search to take advantage of a lower, “extended” search fee in MARPAT.For additional information on file-specific charges see HELP COST in the file.

MARPAT Overview

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L6 ANSWER 2 OF 3 MARPAT COPYRIGHT 2000 ACSAN 126:199581 MARPATTI aryl substituted pyrrolopyrazines as a new class of GABA brain Receptor ligandsIN Blum, Charles; Hutchison, AlanPA Neurogen Corporation, USASO U.S., 16 pp. Cont.-in-part of U.S. 5,286,860. CODEN: USXXAM

o o oL6 ANSWER 3 OF 3 MARPAT COPYRIGHT 2000 ACSAN 120:245160 MARPATTI Preparation of indolopyrazines and related compounds as brain GABAa agonists, antagonists, or inverse agonistsIN Blum, Charles; Hutchison, AlanPA Neurogen Corp., USASO U.S., 17 pp.

o o o(continued on next page)

MARPAT Overview

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o o oFAN.CNT 3

PATENT NO. KIND DATE APPLICATION NO. DATE --------------- ---- -------- --------------- --------PI US 5286860 A 19940215 US 92-975409 19921112 WO 9411374 A1 19940526 WO 93-US10870 19931110 W: AT, AU, BB, BG, BR, BY, CA, CH, CZ, DE, DK, ES, FI, GB, HU, JP, KP, KR, KZ, LK, LU, MG, MN, MW, NL, NO, NZ, PL, RO, RU, SD, SE, SK, UA, US, VN RW: AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG AU 9455526 A1 19940608 AU 94-55526 19931110 US 5606059 A 19970225 US 95-436252 19950512 US 5668283 A 19970916 US 95-486595 19950607

o o o

MARPAT Overview

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Formats showing structures:

Use this format If you want to displayHITSTR In CAplus: The structure(s) of the

specific compounds(s) that caused theanswer to be retrieved

FQHIT In MARPAT: The hit portion only for thefirst hit Markush structure in the answer

FHIT In MARPAT: The hit Markush structure inthe answer with the hit portionshighlighted

MSTR In MARPAT: All the Markush structuresassociated with an answer

Note: This display can be very long forcomplex Markush structures

CASLINK

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=> d an fhit

AN 127:293247 MARPAT

MSTR 2A

1NG3 3

N

N

G1

HG1 = Ph (SO (1-2) G2) / thienyl (SO (1-2) G2) / pyridyl (SO (1-2) G2)

MARPAT Overview

N

N

NO

N

Ak

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1NG3 3

N

N

G1

HG3 = 14-3 15-1 / 74-3 75-1

14G6

15G4G5

G5 74G29

G30

75G34

MARPAT Overview

N

N

NO

N

Ak

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14G6

15G4G5

G5 74G29

G30

75G34

G4 = (0-2) CH2G5 = H / alkyl<(1-6)>G6 = 19 / C(O) / 22 . . . . . . . . . . . . .

MARPAT Overview

N

N

NO

N

Ak

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REGISTRY and MARPAT, Retrieval Differences:

• In REGISTRY, only specific substituents are present in the database compounds. Substructures match against specific substituents.

• In MARPAT, substructures may match against– Specific substituents: H, CF3, CN, etc.– Generic substituents: X, HY, alkoxycarbonyl, etc.

MARPAT Overview

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• Answers in each database are different:

– Answers in REGISTRY are compounds. The bibliographic references and abstracts associated with each compound (from patents and journals) are available in CAplus.

– Answers in MARPAT are references to patents.

MARPAT OverviewREGISTRY and MARPAT, Retrieval Differences:

57

Retrieval in MARPAT of incompletely defined substances (IDS/CIIDS/CI)

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Incompletely defined substances are assigned CAS RNs in REGISTRY when all of the atoms in the structure are defined and the only uncertainty is one or more of the following:

Attachment position for a substituent

Site of saturation/unsaturation

Site of esterification/etherification

Branching of an alkyl group

Generally it is not possible to anticipate and allow for all of these possibilities in a structure query for REGISTRY. As a result, some potentially interesting substances may be missed in a substructure searchsubstructure search in REGISTRY.

Incompletely defined substances

59

MARPAT can effectively encompass an incompletely defined portion of the molecule in the Markush structure with its ability to support:

Variable attachment points for substituents G-group lists of substituent possibilities


60

Find all non-polymeric glycerides Find all non-polymeric glycerides containing oleic and/or stearic containing oleic and/or stearic fatty acid. fatty acid. Show as Marpat can find some Show as Marpat can find some patents,due to IDS compound, not patents,due to IDS compound, not retrieved by structure search.retrieved by structure search.


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Incompletely defined substances => fil marpat L1 STRUCTURE UPLOADED

=> l1 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE**

O CH2

CH2

Me7-7

7-7

O

CH2

CH

CH2

O

O

62

Incompletely defined substances=> fil reg => c h o/elf(p)21-57/c(p)4-6/o not (pms/ci or rsd/fa)L3 17741 C H O/ELF(P)21-57/C(P)4-6/O NOT . . . . => fil hcaplus => l3 and marpat/osL4 2860 L3 AND MARPAT/OS => fil marpat => l4L5 2860 L4 => l1 full subset=l5L7 870 SEA SUB=L5 SSS FUL L1 ((Patents in MarpatPatents in Marpat))

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=> fil reg => l1 full subset=l3L9 1517 SEA SUB=L3 SSS FUL L1 => l3 and (propan? or glycer?)/cns(l)(octadecen? or oleic? or octadecan? or stear?) L10 1330 L3 AND (PROPAN? OR GLYCER?)/CNS(L) . . => l10 and ids/ciL11 909 L10 AND IDS/CI => l11 not l9L12 885 L11 NOT L9 ((Extra IDS compounds fromExtra IDS compounds from dictionarydictionary))

64


=> fil hcaplus => l9 and p/dtL13 1805 L9 AND P/DT ((Patents from structurePatents from structure)) => l11 and p/dtL14 6344 L11 AND P/DT((Patents from extra IDSPatents from extra IDS)) => l14 not l13L15 5906 L14 NOT L13 ((Patents only from extra IDSPatents only from extra IDS)) => l7L16 870 L7 ((Patents from MarpatPatents from Marpat)) => l15 and l16L17 234 L15 AND L16 ((Patents, only extra IDS,Patents, only extra IDS, retrievedretrieved by Marpatby Marpat))

65


RN 25496-72-4 HCAPLUS CN 9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol CM 1 CRN 112-80-1 CMF C18 H34 O2 Double bond geometry as shown.

(CH2)7 (CH2)7MeHO2C

Z

CM 2 CRN 56-81-5 CMF C3 H8 O3

CH CH2CH2

OH

OHHO

66

Locate information on substances with the following structural characteristics?

Any substitution at all open sitesHy = heterocycle containing exactly 3 N and no O, S, or PAll rings are isolated/embedded-SO3H groups attached at any position on the benzene rings

Cl

N O N

NN O

Cl

Hy

Cl

N

S

O

O

O S

O

O

O


67

=> 5/nrrs(s)c18n2o2/rf(p)cnrs>=3(p)c6/ea(p)3 n/rel and cl>=3(p)s>=2(p)o>=8(p)n>=8L1 509 5/NRRS(S)C18N2O2/RF . . .

=> l1 and ids/ci 234090 IDS/CIL2 160 L1 AND IDS/CI


68

(CH2)3Ph

Cl

Cl

ClNO

ON

H2N

NHN

N

N

N

S CH

O

O

CH2

SO3HD12


=> FILE REGISTRY

L3 STRUCTURE UPLOADED

=> D L3

=> l3 full

L4 115 SEA SSS FUL L3


O

N

N

O

Cl

Cl

N

N

Hy

S

O

O

O

S

O

O

ON

Cl

=> fil marpat

=> l4 full




=> fil caplus=> d his (FILE 'HOME' ENTERED AT 06:29:23 ON 08 MAR 2004) FILE 'REGISTRY' ENTERED AT 06:29:41 ON 08 MAR 2004L1 505 5/NRRS(S)C18N2O2/RF(P)CNRS>=3(P)C6/EA(P)3 N/REL AND CL>=3(P)S>=L2L2 160 L1 AND IDS/CIL3 STRUCTURE UPLOADEDL4 115 L3 FULL FILE 'MARPAT' ENTERED AT 06:32:31 ON 08 MAR 2004L5 51 L4 FULL

72


=> l2 and p/dtL6 21 L2 AND P/DT (Reg. IDS/CAPlus) => l4 and p/dtL7 28 L4 AND P/DT (Reg. Str./CAPlus) => l5L8 51 L5 (Marpat)

73


=> l6 and l7L9 3 L6 AND L7 => l6 not l9L10 18 L6 NOT L9 => l10 and l5 51 L5L11 2 L10 AND L5 (IDS structures recovered in MARPAT)

74

CASLINK

75

• The CASLINK tool provides one-step searching of both the– Specific substancesSpecific substances in REGISTRY– Prophetic substancesProphetic substances in MARPAT

• CASLINK also retrieves the references to the specific substances from CAplus and eliminates any duplicate hits between CAplus and MARPAT.

CASLINK

76

Search Question:

Locate references on the following substances:

R1 = Any non-hydrogen substituent ring or chainR2 = any ring or chain carbon atomNo additional fusion on the ringAdditional substitution allowed at all open sites

CASLINK

77

1Enter the CASLINK cluster of files=> FILE CASLINKFILE 'REGISTRY' ENTEREDFILE 'MARPAT' ENTERED FILE 'CAPLUS' ENTERED

Predefined command sequences will be executed in REGISTRY, MARPAT, MARPATPREV, and CAPLUS.

2Perform the upload=>Uploading mar1.str


CASLINK

78

3 Verify the structure online=> D L1

L1 HAS NO ANSWERS

L1 STR

N

O

O

O

A

CASLINK

79

Run a SAMPLE search

=> S L1 SSS SAM

PROJECTED ITERATIONS: 4669 TO 6691

PROJECTED ANSWERS: 68 TO 532

L2 15 SEA SSS SAM L1

CASLINK

80

S L2 SSS SAM FILE=MARPAT

FULL FILE PROJECTIONS: ONLINE **COMPLETE**

BATCH **COMPLETE**

PROJECTED ITERATIONS: 9195 TO 11845

PROJECTED ANSWERS: 3 TO 164

L3 3 SEA SSS SAM L1

CASLINK

81

• Each answer from REGISTRY is a specific compound that matches the structure query.

• Each answer from MARPAT is a document record (patent) in which the Markush structure contains fragments that matchs the structure query.

• D SCAN is used to determine if the REGISTRY and MARPAT answers are on target. D SCAN content is file-specific.

CASLINK

82

=> D SCAN L2L2 15 ANSWERS REGISTRY COPYRIGHT 2000 ACSIN 3-Pyrrolidinecarboxylic acid, 4-ethenyl-2-oxo- 1-(phenylmethyl)-, Methyl ester, (3R,4R)-rel-

(9CI)MF C15 H17 N O3

Relative stereochemistry.

HOW MANY MORE ANSWERS DO YOU WISH TO SCAN? (1):0(continued on next page)

MeO

Ph

O

O N

CH2S S

Note: Substance identification information from REGISTRY.

CASLINK

83

=> D SCAN L3

MSTR 1

G5 = CHOG6 = 22

MPL: claim 1STE: diastereoisomers and mixtures

HOW MANY MORE ANSWERS DO YOU WISH TO SCAN? (1):0

G1

OC(O)G6

G4

22

NO OG5

CASLINK

N

O

O

O

A

84

• When a FULL structure search is requested in CASLINK, STN:

1 Runs FULL structure searches in REGISTRY, MARPAT

2 Searches the REGISTRY answers in Caplus

3 Removes duplicateRemoves duplicate** answers between CAplus and MARPAT and creates a single answer set

CASLINK

85

=> S L1 SSS FULL

S L1 SSS FUL FILE=REGISTRY


S L4 SSS FUL FILE=MARPATL5 54 SEA SSS FUL L1

S L4 FILE=CAPLUS

L7 161 FILE CAPLUS

CASLINK

86

DUP REM L5 L7 (this dup rem is useless)(this dup rem is useless)

PROCESSING COMPLETED FOR L5

PROCESSING COMPLETED FOR L7

L8 209 DUP REM L6 L5 L7 (6 DUPLICATES REMOVED)

ANSWERS '1-54' FROM FILE MARPAT

ANSWERS '55-209' FROM FILE CAPLUS

CASLINK

87

Illustration: FQHIT vs. FHIT in MARPAT

With FQHIT display format, only the portions of the Markush structure that caused it to be a "hit" are displayed. The format is useful to

Get a general idea of the context in which a structure hit Determine if a structure query is too broad Display large numbers of MARPAT hits

CASLINK

88

Step 6: Display Results

=> D 5 FQHIT

L8 ANSWER 5 OF 209 MARPAT COPYRIGHT 2000 ACS DUPLICATE 6 MSTR 1

G7 = alkoxycarbonyl<(1-8)> (SO (1-) G8)G11 = OMPL: claim 1

N

G1

G1

G7

G9

G10

G12G11

89

Illustration: FQHIT vs. FHIT in MARPAT

With FHIT display format, all G-group definitions are shown. It is useful when you need to see the entire context in which a structure hit.

CASLINK

90

=> D 5 FHITL8 ANSWER 5 OF 209 MARPAT COPYRIGHT 2000 ACS DUPLICATE 6 MSTR 1

G1 = H / X / CF3 / CN / Me / 13 / 16 / SMe / 20 / SO2Me / 23 / 30 / (SC Cl)

G2 = 13 / 18 / CF3

G3 = Me / COPhG4 = H / MeG5 = pyridyl (SO (1-) G6)G6 = X / CF3G7G7 = X / CN / CO2H / alkoxycarbonyl<(1-8)> (SO (1-)alkoxycarbonyl<(1-8)> (SO (1-) G8) G8) / cycloalkyloxycarbonyl<(3-8)> (SO (1-) G13) / (SC Cl / CO2Et) / (EX 54 / 43)


N

G1

G1

G7

G9

G10

G12G11

13F2C CF2 H

16O G2

20S Me

O23C N O G3

G4 30O G5

13F2C CF2 H

18F2C H

The parts that caused the answer to be a "hit" are highlighted.

CASLINK

91

G8 = X / CF3 / Ph / cycloalkyl<(3-7)>G9 = alkyl<(1-4)> (SO (1-) cyclopropyl) / cycloalkyl<(3-4)> (SO (1-) Me) / alkenyl<(2- 4)> / (SC Et / CH=CH2) / (EX 48)

G10 = H / X / (SC F)G11G11 = OO / SG12 = H / X / (SC Cl)G13 = X / CF3 / Ph / alkyl<(1-5)>MPL: claim 1

43C(O) O CH2Me

54C(O) O CH

Me

48H2C

The parts that caused the answer to be a "hit" are highlighted.

Helpful Hint:Helpful Hint: Markush displays can be very complicated.OptionOption: Consider displaying the associated CAplus abstract. Many contain structural summaries of the claimed substances.

CASLINK

92

Markush displays in MARPAT consist of• Base structure• G-groups defining the variability in the structure

G-groups in MARPATdisplays may contain

Example

Real atoms G1 = O / S / NH / CH2

Variable groups G2 = H / X / CF3 / CN / Me

Variable groups with deeperlevels of definition

G3 = OH / / Hy<EC (3-7) A (1-2)Q (1-2) N (0) OTHERQ, RC (1),RS (1) X7> (SO) / NMe2

CASLINK

93

G - g r o u p s i n M A R P A Td i s p l a y s m a y c o n t a i n

E x a m p l e

S t r u c t u r a l f r a g m e n t si d e n t i f i e d b y n o d e n u m b e r s

G 4 = 1 3 / 1 8 / C F 3

1 3F 2 C C F 2 H

1 8F 2 C H

G e n e r i c t e x t s h o r t c u t s G 5 = O H / a l k o x y / X / N H 2 /a l k o x y c a r b o n y l / C O 2 H /

T e x t u a l i n f o r m a t i o nd e s c r i b i n g a n o n - s t r u c t u r a le n t i t y

G 6 = R < T X " p r o t e c t i n gg r o u p " > / C H 2 P h /C H 2 C H = C H 2

CASLINK

94

Levels in Marpat

95

Search Question:

Locate references discussing compounds with the following structure:

R1 = heterocyclic ring with at least one =O attached R2, R3 = any type of carbon chain (substituted or unsubstituted)The oxygen-containing ring may be isolated or embedded in a larger ring systemAny substitution at all open sites

All of the atoms in the structure, except for the benzopyran ring, may match real atoms or generic groups in Markush structures.The benzopyran ring may match only real atoms.

Levels in Marpat

96

Hy

Hy=O

Ak (conn. = any)

Ring Isolated

Connectivity: any

Class

Class

Atom

Levels in Marpat

97

• Match Levels may be changed on a single node or a group of nodes.

• To change match level of a single node1 Right click on the node. A pop-up menu appears. Select

Markush Attributes

Levels in Marpat

98

• Match Levels may be changed on a single node or a group of nodes.• To change match level of a single node

2 The Markush Attributes dialog box appears. Do the following:– Click the radio button associated with the Match Level of interest.

– Click OK.

Levels in Marpat

99

• To change match level on multiple nodes all at once, 1 Highlight the nodes using the highlighting tool.

Levels in Marpat

100

• To change match level on multiple nodes all at once, 2 From the Query Def pull-down menu, select Markush Attributes. An alert dialog box appears. Click OK.

The Markush Attributes dialog box appears. Do the following:

a Click the radio button associated with the Match Level of interest.

b Click OK.

Levels in Marpat

By default STN Express assign the level CLASS to all chains, By default STN Express assign the level CLASS to all chains, and level ATOM to all rings. But you can (must) change it.and level ATOM to all rings. But you can (must) change it.

101

• Verifying Match Levels Assignments1 From the Query Def pull-down menu, select Query Verification.2 The Query Verification dialog box appears.

a Click the Select radio button.

b Click in the match level box.

c Click OK.

Levels in Marpat

102

• Verifying Match Levels Assignments3 A Query Verification pop-up dialog appears and Match Levels

for all atoms display. Click OK.

(You can better verify clicking on the Q button)

Levels in Marpat

103

=> FILE CASLINK

=>

Uploading mar2.str


=> D L1

L1 HAS NO ANSWERS

L1 STR

CLASS match level on:Cl, Ak, O, Hy

ATOM match level on:All atoms in the benzopyran ring.

Levels in Marpat

104

=> S L1 SSS SAMS L1 SSS SAM FILE=REGISTRY

o o oL2 0 SEA SSS SAM L1

o o oS L2 SSS SAM FILE=MARPAT

o o o L3 4 SEA SSS SAM L1

o o o

=> D SCAN L3 FQHIT

Levels in Marpat

105

L3 4 ANSWERS MARPAT COPYRIGHT 2000 ACS MSTR 1A

G1 = 11

G2 = alkyl<(1-6)>G3 = alkyl<(1-6)>G7 = Hy<EC (4-5) C (1-2) N (0) OTHERQ, AN (1-) N

(1-) C, BD (1) D (0) T, RC (1), RS (1) E6 (0) OTHER> (SO)

o o o HOW MANY MORE ANSWERS DO YOU WISH TO SCAN? (1):0

Note that FQHIT shows only the fragments that caused the structure to hit. For example, the complete definition of G6 is not shown - only the part that caused the answer to be a hit (G7) is shown.

Levels in Marpat

106

=> S L1 SSS FULLS L1 SSS FUL FILE=REGISTRY

o o oL4 6 SEA SSS FUL L1

o o oS L4 SSS FUL FILE=MARPAT

o o oL5 42 SEA SSS FUL L1

o o oS L4 FILE=CAPLUSL7 14 FILE CAPLUS

o o o L8 51 DUP REM L6 L5 L7 (5 DUPLICATES REMOVED) ANSWERS '1-42' FROM FILE MARPAT

ANSWERS '43-51' FROM FILE CAPLUS

Levels in Marpat

107

=> D 1 BIB ABS FQHITL8 ANSWER 1 OF 51 MARPAT COPYRIGHT 2000 ACS DUPLICATE 1

AN 121:255814

MSTR 1

G1 = X

G3 = alkyl<(1-6)>

MPL: claim

Answers from MARPAT.

Levels in Marpat

108

Levels in Marpat=> D 45 51 BIB ABS HITSTR

L8 ANSWER 45 OF 51 CAPLUS COPYRIGHT 2000 ACS

AN 1988:112204 CAPLUS

DN 108:112204

Answers from CAplus/REGISTRY.

109

Search REGISTRY/CAplus and MARPAT to locate references discussing substances with the following structure

R1 = nitrogen in a ring or chainR1 = nitrogen in a ring or chain

R2 = anything, including hydrogenR2 = anything, including hydrogen

R3,R4 = alkyl chainR3,R4 = alkyl chain

Nitrogen-containing ring may be isolated or Nitrogen-containing ring may be isolated or embedded in a larger ring systemembedded in a larger ring system

Any substitution is allowed at all open sitesAny substitution is allowed at all open sitesConsider Class the rings and Atoms the chainsConsider Class the rings and Atoms the chains

Display the final answer set using the following formats:

For MARPAT answers use BIB ABS FQHIT

For CAplus answers use BIB ABS HITSTR

Skills Practice

110

=> fil reg=> Uploading C:\STNEXP\Queries\19a.strL1 STRUCTURE UPLOADED

N

Ak

N

Ak

CH2SO2

N

111

=> l1FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE**PROJECTED ITERATIONS: 1864 TO 3216PROJECTED ANSWERS: 8 TO 329 L2 8 SEA SSS SAM L1 => d scan

NHEtMeO

CH2 CH2

NH

CH2SNH

O

O

CH2CH2

112

=> l1 fullL4 170 SEA SSS FUL L1

=> fil caplus => l4L5 1132 L4

113

=> d l5 bib abs hitstr L5 ANSWER 1 OF 1132 CAPLUS COPYRIGHT 2006 ACS on STN AN 2006:151208 CAPLUS Full-textTI Transnasal composition having immediate action and high absorbability. . . . . . . . . . . . . . . . . . . . AB Disclosed is a powdery composition for transnasal administration which contains a nonpeptidic nonproteinaceous drug and crystalline cellulose masses having a specific mesh-size as a carrier therefor. This composition can exert an immediate action of the drug and a high absorbability. For example, morphine hydrochloride 65 mg and Avicel PH-F20 (crystalline cellulose) 135 mg were blended and nasally administered to monkeys for the determination of pharmacokinetic parameters of morphine.

http://chemport.cas.org/cgi-bin/ex_sdcgi?rQe7Seza0TKDWP2keXQu@r7c5QpdBFfMF4xlTePiaHbJAMrZggxB94zN5XoBBf2OhkcNeiNI3fteLWRrnrDubr@knWrZ_mQ6QTS5sfa_z2boYlrNw@RBwgx0iQaH7t3CEQYixfx@UMsrRAYyye0AwvKioyZBPAIS1DeAwbWK3y@krB70KJcUl9BLyjDpIMmq

114

IT 103628-46-2, SumatriptanRN 103628-46-2 CAPLUS CN 1H-Indole-5-methanesulfonamide, 3-[2- (dimethylamino)ethyl]-N-methyl- (9CI) (CA INDEX NAME)

NMe2MeNH CH2 CH2

NH

CH2S

O

O

115

=> fil marpat => l4FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE**PROJECTED ITERATIONS: 16297 TO 19783PROJECTED ANSWERS: 2 TO 125 L7 2 SEA SSS SAM L1

=> d scan

116

L7 2 ANSWERS MARPAT COPYRIGHT 2006 ACS on STN . . . . . . . . . . . . . . . . . . . . . . . . TI Preparation of indole derivatives as antagonists of gonadotropin releasing hormone. . . . . . . . . . . . . . . . . . . . . . . . . MSTR 1

N9

G8G15

G16G17

G16G16

G48 12N 13G1 14G49

G47

991G9

117

=> l4 fullL9 63 SEA SSS FUL L1 => d bib abs fqhit

L10 ANSWER 1 OF 44 MARPAT COPYRIGHT 2006 ACS on STN AN 143:341070 MARPAT Full-textTI Synergistic broad-spectrum microbicide compositions containing sulfamoyl compounds and dipeptides or basic copper chloride. . . . . . . . . . . . . . . . . . . . . . . . . . . .GI

NSO2

N

NN SO2

O

O

NH

Pr-iNH

O O

NR1R2

R3R4R5

R6

R7

R8

R1 OR3

R2

I

II

http://chemport.cas.org/cgi-bin/ex_sdcgi?_QU7beAacTFDZPIwcXAuJrectQ2d3FIMr4flfeNirHrJ3M0iNgSB64eNFXdBRfkOikDNuijIifMe7WtQerDuwrPkcWrZMmq6vTi5ff@_L2roVlRRc@nBUgL0xQrHjtCCQYixfx@QMsrRAY3yx0AweKJocZGPDI01PeWwNWL3v@CrQ7QrpcUl9BWy_D4IXmq

118

AB The microbicide compns. contain (A) sulfamoyl compds. I [R1, R2 = C1-4 alkyl; R1R2 may form C4-6 alkylene; Y = H, halo, C1-8 alkyl, C1-6 alkoxy, C1-10 alkylthio, C1-6 haloalkyl, C1-6 haloalkylthio, (un)substituted benzylthio, (un)substituted Ph, (un)substituted benzyl; R3-R8 = H, C1-8 alkyl, C3-8 cycloalkyl, C2-8 alkenyl, C5-8 cycloalkenyl, C2-8 alkynyl, C1-8 alkoxy, etc.] and/or their agrochem. acceptable salts and (B) dipeptides II (R1 = iso-Pr, Ph; R2 = Me; R3 = Ph substituted with R4 at the 4-position, 2-benzothiazolyl which may be substituted with R5; R4, R5 = F, Cl, Me, Et, MeO, cyano) or (C) basic copper chloride (copper oxychloride) (III). Concomitant application of 1-(N,N-dimethylsulfamoyl)- 3-(3-bromo-6-fluoro-2-methylindol-1-yl)sulfonyl-1,2,4-triazole (at 0.625 g/ha) and Me ()-RS-[3-(N-isopropoxycarbonyl-S-valinyl)amino]-3-(4- chlorophenyl)propanoate (at 2.5 g/ha) showed 80% control of disease caused by Phytophthora infestans in potato.

NSO2

N

NN SO2 G1

G2G5

G5G5G5

G5G5

G5 = alkyl <containing 1-4 C> (substd. by G7) G7 = dialkylamino <each alkyl containing 1-6 C> / dialkylaminosulfonyl <each alkyl containing 1-6 C>

119

Precision Tools

120

• Techniques for modifying structure queries for Markush searching are available.

• These structure drawing tools will either expand or reduce the number of answers retrieved in MARPAT file.

Precision Tools

121

Match level (limited, unlimited) Generic definitions (Generic Groups) Element count (Generic Groups)

Precision Tools

122

• Each atom in a query structure is assigned a default Match Level.

• Match Level controls how query atoms match specific atoms and generic groups in the MARPAT database.

• Three Match Level options are possible

Database Retrieval possibilities

REGISTRY Specific atoms

MARPAT Specific atoms

Generic groups that matchthe query definition

Match Level is ignored in REGISTRY

Precision Tools

123

Match Level

• Markush structures include both real atoms and generic nodes, both of which may be matched against the real atoms and generic nodes (Ak, Cb, Hy,Cy) of the search query.

• Match levelMatch level determines the degree to which query nodes match with nodes in the candidate answers.

• Changing the degree of matching will increase or decrease the number of answers retrieved.

Precision Tools

124

Match Level

There are three match levels:

AtomAtom ClassClass AnyAny

Precision Tools

125

Match Level Atom

• Match level atom is the most restrictive match level.

• It retrieves the most precise set of answers: Specific atoms in the query match only

specific atoms in candidate answers. Generic groups in the query match only

specific atoms in candidate answers.

Precision Tools

126

Example Match Retrieval

Query atom Database hit

Atom

Real atoms

Br

Br

X Br, Cl, F, etc

Pyridine ring Pyridine ring

Hy Pyridine, thiophene, benzofuran, etc

Precision Tools

Match Level Atom

127

Match Level Atom

Query node

Candidate answer node

Match?

Cl Cl Yes

Cl Br No

Cl X No

X Cl or Br or F or I or At

Yes

X X No

Precision Tools

128

Match Level ClassMatch level class causes more answers to be retrieved than match

level atom: Specific atoms in the query match specific

atoms and “generic nodes” in candidate answers.

Generic groups in the query match specific atoms and generic groups in candidate answers.

HINTHINT:: the Class level is the most important level and you the Class level is the most important level and you

should always run searches in Marpat at this levelshould always run searches in Marpat at this level

Precision Tools

129



Class Real atoms Generic

groups (Q X M Ak Hy Cb Cy)

Br

X

Br, X

Br, Cl F, etc., X

Pyridine ring Pyridine ring, “Hy”

Hy Pyridine, thiophene, benzofuran, etc., Hy

Precision Tools

Match Level Class

130

Query node


Match?

Cl Cl Yes

Cl Br No

Cl X Yes


Yes

X X Yes

Precision Tools

Match Level Class

131

Match Level Any• Match level any is the least restrictive match level

option. • In addition to specific atoms and generic nodes,

candidate answers also include R-nodes. • R-nodes are indefinite substituents described with

text terms such asOrganic groupGroup to form ringAnionProtecting group

Precision Tools

132



Any Real atoms

Generic groups

Any Rb

Br Br, X, R

Pyridine ring Pyridine ring, Hy, R

Precision Tools

Match Level Any

133

Query node


Match?

Cl Cl Yes

Cl Br No

Cl X Yes

Cl R-node Yes


Yes

X X Yes

X R-node Yes

Match Level Any

Precision Tools

134

Helpful HINT

Using match level any for an entire query is a nonsense. It retrieves far too many irrelevant answers and greatly extends the search time. Assign match level any to selected nodes in the query to

Broaden the query Increase the recall Match R-nodes like “protecting group”

Precision Tools

Match Level Any

135

In Marpat all pieces of structures (in query, or in the file) are also converted in

Generic GroupsGeneric Groups

Precision Tools

136

CH

CHN

CHCH2

CH2Me

Cl

Ak Hy X

Cy

Precision Tools

137

CH

CHN

CHCH2

CH2Me

Cl

In Marpat then, to the above structure is associated, in any case, the following string:

Ak*-Hy*(or Cy*)-X*

* Indicates that are generated Generic Groups and not original Generic Groups

Precision Tools

138

In searches at atom level the query does not match generated generic groups or original generic groups, but only specific atoms or groups (i.e. phenyl, ethyl, etc.)

In searches at class level the query matches also generated generic groups or original generic groups, but never query generated generic but never query generated generic groups match file generated generic groupsgroups match file generated generic groups

Precision Tools

139

O ||C=C-C-O-Ak-X

G1 O | ||CH2=C-C-O-CH2-ClG1 = H / Me

Hit (atom)

O ||CH2=CH-CH2-C-O-Ak-Br No Hit

O ||G2-C-O-G1G1 = alkyl (SO X) / PhG2 = alkenyl <2-6> / loweralkyl

Hit (class)

Q*

||

Ak*-Q*-Ak-X

O

||

Ak-C-O-Ak-BrHit (class)

Precision ToolsQUERY FILE

140

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

Ak

CH2 CH2 NH2

M.le All Class

M.le All Atom

Yes

No

Precision Tools

FILE

141

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

Me

CH2 CH2 NH2

M.le All Class

M.le All Atom

Yes

Yes

Precision Tools

FILE

142

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

Ak

Ak NH2

M.le All Class

M.le All Atom

Yes

No

Precision Tools

FILE

143

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

Ak

Ak CH2 NH2

M.le All Class

M.le All Atom

Yes

No

Precision Tools

FILE

144

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

Ak

CH2 CH2 NH2

M.le All Class

M.le All Atom

No

NoAk

Precision Tools

FILE

145

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

CH

CHN

CH

R

CH2 CH2 NH2

M.le All Class

M.le All Atom

No

NoFILE

146

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

M.le All Class

M.le All Atom

Yes

NoEt-Hy-Ak-NH2FILE

147

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

M.le All Class

M.le All Atom

Yes

NoAk-Hy-Ak-NH2

Precision Tools

FILE

148

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

M.le All Class

M.le All Atom

No

NoAk-Cb-Ak-NH2

Precision Tools

FILE

149

CH

CHN

CH

Ak

CH2 CH2 N

QUERY

M.le All Class

M.le All Atom

Yes

NoAk-Cy-Ak-NH2

Precision Tools

FILE

150

Default Match Level in STN Express

• Structure queries automatically include default match level assignment.

• This assignment is only taken into account when searching MARPAT or MARPATprev.

• The default settings for match levels are AtomAtom, for ring atoms and the ring

generic groups Cy, Cb, and Hy ClassClass, for chain atoms and the

chain generic group Ak

Hint: change this default, in Preferences, and put all atoms at class level

Precision Tools

151

Match Level Assumptions in STN ExpressBy default, Match

Level is set asFor the following parts of a structure

Atom All atoms in a ring system

Hy, Cb, Cy

Class All chain atoms in a structure

Precision Tools

152

If in the query there is Consider this Match Level option

A chain spacer of a certain length that must be present

Change the Match Level for the chain to ATOM

Precision Tools

Tips for setting ATOM Match Levels

153

Tips for setting CLASS Match LevelsIf in the query there is Consider this Match Level

option

A specific ring system When you want to retrieve thereal atom ring system, plusgeneric groups that encompassthe ring definition, change MatchLevel for all atoms in the ring toCLASS

Change Match Level for all ring atoms to CLASS.

Precision Tools

154

If in the query there is Consider this Match Leveloption

Hy, Cb, Cy When you want to retrieve realatom rings matching the ringgeneric group, plus the genericgroup, change Match Level onthe generic group to CLASS

Change Match Level to CLASS.

Precision Tools

Tips for setting CLASS Match Levels

155


M, Q, X, or A as part of aring system

When you want to match specificelements, as well as thecorresponding generic groups,change the Match Level on thoseatoms to CLASS.

Tips for setting CLASS Match Levels

Precision Tools

Change Match Level to CLASS. Rest of ring atoms are ATOM.

156


A substituent that is oftendescribed generically inpatent claims, e.g., anelectron withdrawinggroup

Assigning Match Level ANY tothose types of substituents.

Change Match Level for the G1 G1 substituentssubstituents to ANY to also match R which might be defined as an “electron withdrawing group.”

Precision Tools

Tips for setting ANY Match Levels

157

Consider match level any, if the query contains

For example:

A substituent that you want to also match on that substituent with "substitution optional" (SO) or "substitution required" (SR) in the textual information

A portion that could match on "acyl" as a textual description of the attachment

Change match level for Ak to any to retrieve hits such as

G1=X/NO2/phenyl (SR)

Change match level for X to any to match the textual phrase "acyl".

Precision Tools

Tips for setting ANY Match Levels

158

1 Use MARPAT to locate patents on compounds with the following structure:

R1, R3, R4, R5 = an alkyl chain of any length with no substitutionsR2 = any ring system with no substitutionsNitrogen-containing ring is not isolated

All the ring systems may match real atom rings or generic groupsThe -CH2-Si-CH2-Si- chain may match only real atomsThe alkyl groups may match real atoms or generic groups

(follows in the next slide)

Skills Practice

159

1 Use MARPAT to locate patents on compounds with the following structure:

R1, R3, R4, R5 = an alkyl chain of any length with no substitutionsR2 = any ring system with no substitutionsNitrogen-containing ring is not isolated

All the ring systems may match only real atom ringsThe -CH2-Si-CH2-Si- chain may match only real atomsThe alkyl groups may match only real atoms

(Look at the differences between the results in this search and the previous one)

Skills Practice

160

=> fil marpat=> Uploading C:\Program Files\stnexp\Queries\19a.strL1 STRUCTURE UPLOADED

isolated ring systemsisolated ring systems :containing 1 : Connectivity Connectivity :10:1 E exact RC ring/chain 11:1 E exact RC ring/chain 12:1 E exact RC ring/chain 13:1 E exact RC ring/chain 14:1 E exact RC ring/chain Match levelMatch level :1:CLASS 2:CLASS 3:CLASS 4:CLASS 5:CLASS 6:Atom 7:Atom 8:Atom 9:Atom 10:CLASS 11:CLASS 12:CLASS 13:CLASS 14:CLASS

161

=> l1 fullL3 1 SEA SSS FUL L1 => d l3 fhit L3 ANSWER 1 OF 1 MARPAT COPYRIGHT 2003 ACS MSTR 1

G1 = loweralkyl / CH=CH2 / CH2CH=CH2 / CH2Ph / Ph (SO) /20 / biphenylyl

NN

NCH2SiCH2SiG1

G1

G1

G1

G1

162

=> Uploading C:\Program Files\stnexp\Queries\19abis.strL4 STRUCTURE UPLOADED

Match levelMatch level :1:Atom 2:Atom 3:Atom 4:Atom 5:Atom 6:Atom 7:Atom 8:Atom 9:Atom 10:Atom 11:Atom 12:Atom 13:Atom 14:Atom

163

=> l4 fullL5 1 SEA SSS FUL L4 => d l5 fhit

L5 ANSWER 1 OF 1 MARPAT COPYRIGHT 2003 ACS MSTR 1G1 = loweralkyl / CH=CH2 / CH2CH=CH2 / CH2Ph / Ph (SO) /20 / biphenylyl

NN

NCH2SiCH2SiG1

G1

G1

G1

G1

164

Run two searches in Marpat on the previous structure.

R1 = unsubstituted carbon chain (Level: atom, class) R2 = O, S, or N,no other substitutions on this atom (Level: atom) R3 = Any type of ring system (Level: atom, class) R4 = Nitrogen in a chain (Level: atom) The nitrogen-containing ring is isolated.

Look at the differences

Skills Practice

165


Ak, Cy Class

166

N N

NG8

G1

G2010CH

G4012G33

G3824G7

G41

G7 = alkyl<(1-6)> (SO) Ak

G41 = 13 / aryl (SO (1-) G28) / Cy cycloalkyl<(3-9)> (SO (1-) G28) / cycloalkenyl<(4-9)> (SO (1-) G28) / Hy (SO (1-) G28)

Ak, Cy Class

167

Ak, Cy Atom

168

G22G30

3G31 G1 5G17

6G19

G3 = / (SC NHCH2Ph) Cy

G40 = / Bu-i Ak

Ak, Cy Atom

169

Suggestions:Suggestions:

Start always a structure search in Marpat with all nodes at Start always a structure search in Marpat with all nodes at Class LevelClass Level and save it (results in Lx); then, if necessary, run and save it (results in Lx); then, if necessary, run a subset structure search on Lx, changing some nodes at a subset structure search on Lx, changing some nodes at Atom Level.Atom Level.

Remember that if you draw in your query a specific group (i.e. Remember that if you draw in your query a specific group (i.e. pyridine), also at Class Level (pyridine), also at Class Level (LimitedLimited), you find ), you find onlyonly Generic Generic Groups which encompass your designed group (i.e. … a Groups which encompass your designed group (i.e. … a heterocycle with N …) heterocycle with N …) notnot other Generic Groups. other Generic Groups.

In order to get the best results it is a general rule to run a In order to get the best results it is a general rule to run a structure search, in Marpat, on a set previously created either structure search, in Marpat, on a set previously created either from Registry eiher from CAPlus.from Registry eiher from CAPlus.

170

Skills Practice

Find patents on cytomegalovirus, and Markush structures that match the structure query:

O Hy

Hy

171

=> fil caplus => (cytomegalovir? or cmv? or cytamegalo?(s)virus) and p/dt L1 2433 (CYTOMEGALOVIR? OR CMV? OR . . . . . . .=> sel rn SmartSELECT INITIATED TERM LIMIT EXCEEDED: 1458 ANSWERS PROCESSEDL2 SEL L1 1- RN : 50359 TERMS => sel l1 rn 1459- SmartSELECT INITIATED L3 SEL L1 1459- RN : 12961 TERMS

172

=> fil reg=> l2 or l3L6 61198 L4 OR L5 => Uploading C:\Program Files\stnexp\Queries\virus.str=> dL7 HAS NO ANSWERSL7 STR

O Hy

Hy

173

=> l7 full subset=l6FULL SUBSET SEARCH INITIATED 10:15:52FULL SUBSET SCREEN SEARCH COMPLETED - 30485 TO ITERATE 100.0% PROCESSED 30485 ITERATIONS 85 ANSWERSSEARCH TIME: 00.00.03 L8 85 SEA SUB=L6 SSS FUL L7

174

FILE 'CAPLUS' ENTERED AT . . . .L1L1 2433 (CYTOMEGALOVIR? . . . . . . . . . L2 SEL L1 1- RN : 50359 TERMSL3 SEL L1 1459- RN : 12961 TERMS FILE 'REGISTRY' ENTERED AT 10:10:05 ON 27 OCT 2003L4 50359 S L2L5 12961 S L3L6 61198 S L4 OR L5L7 STRUCTURE UPLOADEDL8L8 85 L7 FULL SUB=L6

175

=> fil caplus=> l8 and l1 11188 L8L9 15 L8 AND L1 => d hitstr

MeMe

HOO

O

S

S

NO

+

S

R

S

R

O Hy

Hy

176

FILE 'CAPLUS' ENTERED AT 10:04:43 ON 27 OCT 2003L1L1 2433 (CYTOMEGALOVIR? OR CMV? OR . . . . . L2 SEL L1 1- RN : 50359 TERMSL3 SEL L1 1459- RN : 12961 TERMS FILE 'REGISTRY' ENTERED AT 10:10:05 ON 27 OCT 2003L4 50359 S L2L5 12961 S L3L6 61198 S L4 OR L5L7 STRUCTURE UPLOADEDL8L8 85 L7 FULL SUB=L6 FILE 'CAPLUS' ENTERED AT 10:16:17 ON 27 OCT 2003L9 15 L8 AND L1

177

=> fil marpat=> l1L10 325 L1

=> l8 full subset=l10FULL SUBSET SEARCH INITIATED 10:19:16FULL SUBSET SCREEN SEARCH COMPLETED - 278 TO ITERATE 100.0% PROCESSED 278 ITERATIONS 34 ANSWERSSEARCH TIME: 00.00.02 L11 34 SEA SUB=L10 SSS FUL L7

178

FILE 'CAPLUS' ENTERED AT 10:04:43 ON 27 OCT 2003L1L1 2433 (CYTOMEGALOVIR? OR CMV? OR . . . . .L2 SEL L1 1- RN : 50359 TERMSL3 SEL L1 1459- RN : 12961 TERMS FILE 'REGISTRY' ENTERED AT 10:10:05 ON 27 OCT 2003L4 50359 S L2L5 12961 S L3L6 61198 S L4 OR L5L7 STRUCTURE UPLOADEDL8 85 L7 FULL SUB=L6 FILE 'CAPLUS' ENTERED AT 10:16:17 ON 27 OCT 2003L9L9 15 L8 AND L1 FILE 'MARPAT' ENTERED AT 10:17:40 ON 27 OCT 2003L10 325 L1L11L11 34 L8 FULL SUB=L10

179

=> file caplus=> l11L12 34 L11 => l12 not l9L13 31 L12 NOT L9 => sel l13 rn SmartSELECT INITIATED New TRANSFER and ANALYZE Commands Now AvailableSee HELP TRANSFER and HELP ANALYZE for Details L14 SEL L13 1- RN : 2630 TERMS

180

=> fil reg=> l14L15 2630 L14 => l7 full subset=l15FULL SUBSET SEARCH INITIATED 10:26:22FULL SUBSET SCREEN SEARCH COMPLETED - 2444 TO ITERATE 100.0% PROCESSED 2444 ITERATIONS 0 ANSWERSSEARCH TIME: 00.00.01 L16 0 SEA SUB=L15 SSS FUL L7

181

FILE 'CAPLUS' ENTERED AT 10:16:17 ON 27 OCT 2003L9L9 15 L8 AND L1 FILE 'MARPAT' ENTERED AT 10:17:40 ON 27 OCT 2003L10 325 L1L11L11 34 L8 FULL SUB=L10 FILE 'CAPLUS' ENTERED AT 10:19:35 ON 27 OCT 2003L12 34 L11L13L13 31 L12 NOT L9L14 SEL L13 1- RN : 2630 TERMS FILE 'REGISTRY' ENTERED AT 10:25:22 ON 27 OCT 2003L15 2630 L14L16 0 L7 FULL SUB=L15

182

=> fil marpat

=> l9L17 12 L9 => l11 not l17L18 31 L11 NOT L17 => d fhit

183

NN

CH2NO

OG2

OC(O) NH CH2 G1

G2 = alkyl<(1-6)> (SO (1-3) G3)alkyl<(1-6)> (SO (1-3) G3) / (SC Me / Et / 129 / 139 / 144 / 148 / 154 / 161)

G3 = OH / NH2 / 37 / morpholinomorpholino /

O Hy

Hy

184

Generic Groups

185

Generic Groups are very important in Marpat because, at level Class, they are they are always involvedalways involved (generated or original)

Generic Groups

186

• Ak Any carbon chain (only first atom need be carbon); any bond value allowed

• Cy Any cyclic group• Hy Any cyclic group with one (1) or

more non-carbon atoms• Cb Any cyclic group with all carbon atoms

Generic Groups

187

Attribute Options Generic groups Saturated: all of the bonds are single exact

Unsaturated: at least one bond is double, triple or normalized

<7 ≥7 Monocyclic

Polycyclic Linear: all of the AK atoms have only one or two attachments to other non-hydrogen atoms

Branched: at least one of the AK atoms has more than two attachments to a non-hydrogen atom 1 >1

Saturation Hy, Cb, Cy, Ak

No. of C atoms

Hy, Cb, Cy, Ak

No. of hetero atoms

Hy, Cy

Type of ring system

Hy, Cb, Cy

Type of chain

Ak

Generic Groups

188

Generic Groups

Ak Cy Hy Cb

Remember that you can use the Element Count:

Minimum, Maximum, Exact, Range

to estabilish the number of atoms

189

Generic Text Shortcuts Ak-based• Ak is a chain of 1 or more carbons, linear or

branched, saturated or unsaturatedAlkanoyl Alkyl -C(O)-, H - C(O) -

AlkenylAk with one or more double bonds, no triple bonds, and two or more carbons, Ak<EC(2-) C,BD (1-) D (0) T> -

An unsaturated monovalent radical chain of two or more carbons, branched or linear, containing one or more carbon-to-carbon double bonds, but no triple bonds

Formed by the removal of one hydrogen from thecorresponding alkene, e.g., CH3 - CH = CH - CH2 -

Generic Groups

190

Alkenylene

An unsaturated divalent hydrocarbon chain radical of at least two carbon atomscontaining one or more double bonds, but notriple bonds

Formed by the removal of two hydrogens from the parent branched or linear alkene,

e.g., - CH = CH -

Alkenylenedioxy - O - alkenylene - O -

Alkoxy alkyl - O -

also called alkyloxy and alkoxyl

Generic Text Shortcuts Ak-based

Generic Groups

- Ak<EC (2-) C,BD (1-) D (0)T> -

191

Alkyl Ak with all bonds single exact

A totally saturated monovalent radical chain, branched or linear

Formed from an alkane by removal of onehydrogen, e.g., Me-, Et-, t-Bu-

Alkylene - alkyl -

A divalent saturated hydrocarbon radical

Formed by the removal of two hydrogens

from the branched or linear parent alkane,e.g., - CH2 -


Generic Groups

192

Alkylidene alkyl = A divalent alkyl radical that is attached to the parent by a double bond or two (2) singlebonds from the same carbon,

e.g., = CH - CH2 - CH3

Alkynyl Ak with no double bonds, one (1) or moretriple bonds, and two (2) or more carbons, Ak< EC (2-) C, BD (1-) T (0) D>An unsaturated monovalent radical chain oftwo (2) or more carbons, branched or linear,containing one or more carbon-to-carbontriple bonds, but no double bonds

Formed by the removal of one hydrogen

from the corresponding alkyne, e.g., HC C , HC C CH2


Generic Groups

193

Lower Any of the “alk” terms may be preceded bythe term “lower” which implies a total

carboncount one (1) to six (6) carbons for

alkanes;2-6 carbons for alkenes and alkynes. Thisterm is used only when no carbon count isgiven in the patent

Loweralkyl Ak with all bonds single exact and one (1)to six (6) carbons

PerhaloalkylAlkyl with all hydrogens replaced by halogenatoms


Generic Groups

194

• Cb is any monocyclic or polycyclic group containing all carbon atoms with any bond values between atoms.

• Hy is any monocyclic or polycyclic group containing one or more non-carbon atoms with any bond values between the atoms.

Generic Text Shortcuts Cb/Hy-based

Generic Groups

195

Aryl Cb with one or more aromatic rings, six (6)or more normalized bonds, and one (1) ormore six (6)-membered rings

Arylene - aryl -

A divalent aromatic radical

Formed by the removal of two (2) hydrogensfrom two different carbon atoms on thearomatic molecule, e.g., phenylene


Generic Groups

196

Cycloalkenyl Cb with one (1) or more double bonds andno triple bonds

An unsaturated monovalent monocyclic orpolycyclic radical containing one (1) or morecarbon-to-carbon double bonds

Formed by the removal of one (1) hydrogenfrom the corresponding cycloalkene, e.g.,cyclopentadienyl, cyclohexenyl

Cycloalkyl Cb with all bonds single exact

A saturated monovalent alicyclic radical

Formed by the removal of one (1) hydrogenfrom the corresponding cycloalkane, e.g.,cyclopropyl, decahydronaphthyl


Generic Groups

197

Heteroaryl Hy with one (1) or more aromatic rings withsix (6) or more normalized bonds and one(1) or more six (6)-membered rings

Hy with one (1) or more aromatic rings andtwo (2) or more double bonds and one (1) ormore five (5)-membered rings

A monovalent radical derived from anaromatic molecule that contains at least one(1) heteroatom.

Formed by removal of one (1) hydrogen fromthe pyridyl, benzopyranyl


Generic Groups

198

Acyl Carbonyl bonded to Ak (which may have R’son it), at the carbonyl carbon

Carbonyl bonded to R, at thecarbonyl carbon

Formyl

Aralkyl Alkyl bonded to one-to-three (1-3) aryls,

HydrocarbylAk

Cb bonded to Ak

Generic Text Shortcuts Hybrids

Generic Groups

199

MARPAT Codes

200

Structure Displays

• MSTR

Display label for the Markush Structure

Example: MSTR 4

Translation: This is the 4th Markush structure in the document

MARPAT Codes

201

• VAR G#Defines the alternatives for a G#

Example: VAR G1 = O / S / 16 / NULL

Translation: G1 is O or S or node 16 or G1 is a direct bond

Node sixteen (16) appears in the structure diagram portion of the display

Structure Displays

MARPAT Codes

202

• REP G#=

Defines a REPeating group and the number of times it repeats

Example: REP G3 = (0-7) CH2

Translation: CH2 repeats (0-7) times

Structure Displays

MARPAT Codes

203

• CVAThe Conditional Variable statement, currently ignored at search time

Example: VAR G1 = H / OH / X VAR G2 = NO2 / Me / Et CVA = If G1 = OH, THEN G2 = MeTranslation: If G1 is the OH alternative, then G2 must be Me and not NO2 or Et. Searched as G1 = H, OH, X and G2 = NO2, Me, Et (STN Express) as VAR G1 = H / OH / X and VAR G2 = NO2 / Me / Et

Structure Displays

MARPAT Codes

204

• DER

DERivative information that cannot be structured

Searched as single words in the Basic Index (default)

Example: DER: or salts or metal complexes

Structure Displays

MARPAT Codes

205

• NTE

General NoTEs


Example: NTE: substitution restricted

Structure Displays

MARPAT Codes

206

• MPL

Location of the Markush structure in the patent


Example: MPL: claim 1

Structure Displays

MARPAT Codes

207

• STE

STEreochemistry


Example: STE: 41,42-cis

Structure Displays

MARPAT Codes

208

• Generic Group Attributes • AN, AR, BD, CH, DC,EC, FA, RC, RS, TXAN, AR, BD, CH, DC,EC, FA, RC, RS, TX

– Found in < > following the generic group they modify– The marked attributes are searched as Generic Definitions

(STN Express queries) or Generic Group Categories (STR command queries)

– All others are ignored while searching

MARPAT Codes

Structure Displays

209

Abbreviation Example Translation

AN Attachment Nodes AN (3) A

AN (2) N

Attached through 3nodes of any kind (A)

Attached through 2 Nnodes

AR Aryl AR (1-)AR (0)

1 or more aromatic ringsis not aromatic

BD* Bonds BD (0) TBD (1-) D (2) SE

no triple (T) bonds1 or more double (D)bonds and two singleexact (SE) bonds

CH Charge CH (2) +CH (1) +-

total of two (2) positivechargesone (1) positive ornegative charge

DC** Degree of Connectivity

DC (0) M3DC (1-) M3

no branchingbranched

EC*** Element Count

EC (1-8) CEC (2-3 N

1-8 carbon (C) atoms2-3 nitrogen (N) atoms

MARPAT Codes

Structure Displays

210

Abbreviation Example Translation

FA**** Fusion Atoms

FA (2-4) CFA (2-) C

2-4 carbon (C) atomsfuse rings2 or more carbon Catoms fuse rings

RC**** Ring Count

RC (2-)RC (1)

polycyclic with 2 ormore ringsmonocyclic

RS Ring Size RS (2-3) E6RS (1) M5 (1) X6and RC (1)

2-3 6-membered rings5- to 6-membered ring

TX Text Qualifiers

R <TX“protectinggroup”>R <TX“residue”>

the patent said“protecting group”the patent said “residue”

* See workshop manual for definitions of asterisks

MARPAT Codes

Structure Displays

211

Precision Qualifiers - EX and SC

• Found in parentheses at the end of the variable definition

• Additional alternatives for the G-group

MARPAT Codes

212

EXAlternatives are found in the EXamples (in the disclosure)Example: VAR G1 = R<TX “leaving group”> /(EX Cl/ Br / I)Translation: Cl, Br and I are alternatives for G1 and were found in the disclosure. VAR denotes variability G1 is the tag on the variable group

Precision Qualifiers

MARPAT Codes

213

SC

Alternatives are Specifically Claimed

Example: VAR G3 = H / alkyl / alkoxy /

(SC Me / OMe)

Translation: Methyl and methoxy are alternatives for G3 and are specifically claimed

Precision Qualifiers

MARPAT Codes

214

Substitution Qualifiers - SO and SR

• Found in parentheses immediately after the group they modify

• In the current implementation, SO and SR are both searched as SO; i.e., as if the substituent were present on the group any number of times, including zero

MARPAT Codes

215

Substitution Qualifiers

SO

Alternative is Substituted Optionally by this group

Example: VAR G1 = Ph (SO 5X) / alkoxycarbonyl (SO CO2H)

Translation: Phenyl is substituted with zero (0) to five (5) halogens Alkoxycarbonyl is substituted with zero (0) or more carboxy groups

MARPAT Codes

216

SR

Alternative has Substitution Required by one (1) or more of this groupCurrently searched as SOExample: VAR G1 = Ph (SR 5X) / alkoxycarbonyl (SR CO2H)Translation: Phenyl is substituted with one (1) to five (5) halogens Alkoxycarbonyl is substituted with one (1) or more carboxy groups Currently searched as zero (0) to five (5) halogens and zero (0) or more carboxy groups

Substitution Qualifiers

MARPAT Codes

217

Occurrence Counts

Occurrence Counts are found in front of the alternative they modify

Used to limit the substitution by specifying how many times an alternative is present

The occurrence counts are not currently searchable

MARPAT Codes

218

(n)

Alternative occurs exactly “n” times

Example: VAR G1 = (1) X / Me

Translation: Exactly one (1) of the G1’s is X Searched as G1 = X,Me (STN Express); VAR G1=X/Me (STR command)

Occurrence Counts

MARPAT Codes

219

(n-)

Alternative occurs “n” or more timesExample: VAR G3 = (2-) H / loweralkyl / X

Translation: Two (2) or more of the G3’s are H Searched as G3 = H, Ak , X (STN Express); VAR G3= H / Ak, X Me (STR command)

Occurrence Counts

MARPAT Codes

220

(-n)Alternative occurs zero (0) to “n” timesExample: VAR G6 = (-1) H / alkyl / CH2PhTranslation: Zero (0) or one (1) of the G6’s are H Searched as G6 = H, Ak , CH2Ph (STN Express); VAR G6 = H / Ak, CH2Ph (STR command)

Occurrence Counts

MARPAT Codes

221

(m-n)Alternative occurs “m” to “n” timesExample: VAR G2 = X / CF3 / Ph (SO (1-2) G3)Translation: The phenyl (Ph) is optionally substituted by one (1) or two (2) of the variable G3’s Searched as the phenyl (Ph) substituted by zero (0) to five (5) G3’s

Occurrence Counts

MARPAT Codes

1 marpat basics (markush structures). 2 where did the term markush come from? in 1923 dr eugene a...

Documents

fil marpat introduction

d introduction slide

marpat queries

term markush

marpat database

patent claims

screen search

carbon atoms r3