GB1465353A - Fused pyrimidine derivatives and preparation thereof - Google Patents

Fused pyrimidine derivatives and preparation thereof

Info

Publication number
GB1465353A
GB1465353A GB1553674A GB1553674A GB1465353A GB 1465353 A GB1465353 A GB 1465353A GB 1553674 A GB1553674 A GB 1553674A GB 1553674 A GB1553674 A GB 1553674A GB 1465353 A GB1465353 A GB 1465353A
Authority
GB
United Kingdom
Prior art keywords
alkyl
prepared
mes
compounds
iii
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1553674A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Inc
Original Assignee
Pfizer Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of GB1465353A publication Critical patent/GB1465353A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1465353 Heterocyclic and carbocyclic fused pyrimidin-4-ones PFIZER Inc 8 April 1974 [20 Feb 1974] 15536/74 Addition to 1458205 Heading C2C [Also in Division A5] Novel compounds I, II and III and cationic salts thereof (in which R is Me, Et, CH 3 CO or -COR<SP>0</SP> (in which R‹ is OH, C 1-4 alkoxy, hydroxy C 1-4 alkoxy, amino or -NH-OH), Y is H, C 1-4 alkyl, C 2-5 carbalkoxy C 1-4 alkyl, carboxy C 1-4 alkyl, or a group -(CH 2 ) m -O-CO-C 6 H 5 or -(CH 2 ) m -O-C 2-5 -alkanoyl (where m is 2 to 4), R 1 is H, C 1-4 alkyl or phenyl and each of R 2 , R 3 and R 4 is H, halo, MeS, MeSO, C 1-4 alkyl, C 1-4 alkoxy or benzyloxy, or R 2 and R 3 or R 3 and R 4 are together methylenedioxy or ethylenedioxy and R 4 or R 2 respectively is as defined above and R 5 is H, halo, MeS, MeSO, C 1-4 alkyl, C 1-4 alkoxy or benzyloxy with the provisos that (i) except where R is Et or CH 3 CO, R<SP>6</SP> is hydroxy C 1-4 alkyl, or Y is other than H, then at least one of R 2 , R 3 , R 4 and R 5 is a benzyloxy, MeS or MeSO group and (ii) when R‹ is amino or -NHOH then Y is hydrogen) are prepared by the methods disclosed in parent Specification 1,458,205. In addition (a) compounds I, III (R=Et) are prepared by reacting a 2-aminoquinoline - 3 - carboxamide or 2 - aminonicotinamide with propionic acid anhydride or triethyl orthopropionate and those where R is CH 3 CO by oxidation of the ethyl group, (b) compounds I, II, III (R = MeSO) are prepared by oxidizing the corresponding MeS compound and (c) compounds I (Y is other than H) are prepared by alkylating the corresponding compound where Y is H. Compounds I (R 1 = R 2 = R 5 =H, R 3 = R 4 = MeO, Y=H, Me, EtOOC- (C 1-2 alkyl) or CH 3 COO-CH 2 CH 2 , R=Et, COOEt or COOCH 2 CH 2 OH) and (R 1 =R 2 = R 4 =R 5 =Y=H, R 3 =MeS, R=COOEt) and compound III (R 2 =R 3 =R 4 =H, R=Et) are prepared. 6 - methylthio - 2 - amino - quinoline - 3 - carboxamide is prepared by cyclizing α-cyano-#- (2<SP>1</SP> - amino - 5<SP>1 </SP>- methylthiophenyl)acrylamide obtained in situ by reduction of the corresponding 2<SP>1</SP>-nitro compound which is prepared by nucleophilic substitution of α-cyano-#-(2-nitro- 5-chlorophenyl)acrylamide using MeS<SP>(-)</SP>Na<SP>(+)</SP>. Compounds I, II and III have anti-allergy activity.
GB1553674A 1974-02-20 1974-04-08 Fused pyrimidine derivatives and preparation thereof Expired GB1465353A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US44413874A 1974-02-20 1974-02-20

Publications (1)

Publication Number Publication Date
GB1465353A true GB1465353A (en) 1977-02-23

Family

ID=23763661

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1553674A Expired GB1465353A (en) 1974-02-20 1974-04-08 Fused pyrimidine derivatives and preparation thereof

Country Status (1)

Country Link
GB (1) GB1465353A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7482455B2 (en) * 2002-10-16 2009-01-27 Smithkline Beecham Corporation Chemical compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7482455B2 (en) * 2002-10-16 2009-01-27 Smithkline Beecham Corporation Chemical compounds

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee