DE10064823A1 - New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension - Google Patents

New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension

Info

Publication number
DE10064823A1
DE10064823A1 DE10064823A DE10064823A DE10064823A1 DE 10064823 A1 DE10064823 A1 DE 10064823A1 DE 10064823 A DE10064823 A DE 10064823A DE 10064823 A DE10064823 A DE 10064823A DE 10064823 A1 DE10064823 A1 DE 10064823A1
Authority
DE
Germany
Prior art keywords
alkyl
aryl
cycloalkyl
aralkyl
alkynyl
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.)
Withdrawn
Application number
DE10064823A
Other languages
German (de)
Inventor
Herve Geneste
Andreas Kling
Udo Lange
Arnulf Lauterbach
Werner Seitz
Claudia Isabella Graef
Thomas Subkowski
Wilfried Hornberger
Michael Kluge
Rainer Spriesterbach
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.)
Abbott GmbH and Co KG
Original Assignee
Knoll GmbH
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 Knoll GmbH filed Critical Knoll GmbH
Priority to DE10064823A priority Critical patent/DE10064823A1/en
Priority to PCT/EP2001/014924 priority patent/WO2002051810A2/en
Publication of DE10064823A1 publication Critical patent/DE10064823A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

(Hetero)aryl-substituted aliphatic carboxylic acid derivatives (I) are new. (Hetero)aryl-substituted aliphatic carboxylic acid derivatives of formula (I) and their salts, prodrugs, pure enantiomers or diastereomers and tautomers are new. T = COOH, a group hydrolyzable to COOH or bioisostere of COOH; U = -(Xu)a-(CR1R2)b-(CH2)c-, -(Xu)a-(CR1R2)b-C(R1)=C(R2)c- or -(Xu)a-(CR1R2)b-CC-; a = 0 or 1; Xu = -(CR3R4)d-, O or S; b, c, d = 0 - 2; R1 - R4 = H, T, OH or halo; or 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-7C cycloalkyl, mono- or di-(1-6C alkyl)-aminoalkyl, 1-2C alkylene-T, 2C alkenylene-T, 2C alkynylene-T, aryl or aralkyl (all optionally substituted (os)); or R1 + R2, R3 + R4 or R1 + R3 = group (completing an os 3-7 membered ring containing 0-3 of O, S and N as heteroatom(s)); G = mono- or bicyclic 6-10C aryl (os) or 5-10C heteroaryl residue (substituted by U and X in adjacent positions); X = CO, CONR'1, NR'1CO, NR'1, S, SO, SO2, SO2NR'1, NR'1SO2, CS, NR'1CS, CS-O, O-CS, CO-O, O-CO, O, CC, CR'2-O-CR'3, CR'2R'3, CR'2R'3-NR'3, C(=CR'2R'3), CR'2=CR'3, CR'2(OR'4)-CR'3, CR'2CR'3(OR'4) or 4-11 membered, mono- or polycyclic cycloaliphatic or aromatic ring (os and containing 0-6 double bonds and 0-6 of O, S and N as heteroatom(s)); R'1 = H or 1-8C alkyl, 2-8C alkenyl, 2-8C alkynyl, OR'5, 3-7C cycloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, (1-6C) alkylcarbonyl, (1-6C) alkoxycarbonyl, 1-6C alkylsulfonyl, aralkoxycarbonyl, aralkylcarbonyl, arylcarbonyl, arylsulfonyl, heteroarylcarbonyl, aralkylsulfonyl, heteroarylsulfonyl or heteroaralkylsulfonyl (all os); R'2, R'3 = H, OH or (1-6C alkyl, 1-4C alkoxy, 2-6C alkenyl, 2-6C alkynyl, cycloalkylalkyl, 3-7C cycloalkyl, aryl, aralkyl, heteroaryl or heteroaralkyl (all os); R'4, R'5 = H or 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, cycloalkylalkyl, 3-7C cycloalkyl, aryl, aralkyl, heteroaryl or heteroaralkyl (all os); A = 4-8 membered, monocyclic, saturated, unsaturated or aromatic ring (os and containing 1-4 of O, S and N as heteroatom(s)), 9-14 membered, polycyclic, saturated, unsaturated or aromatic ring (os and containing 1-6 of O, S and N as heteroatom(s) or -C(=Z)-Z'; Z, Z' = O, S or N (os); R18, R 19 = H or 1-8C alkyl, 2-6C alkenyl, 2-6C alkynyl, (1-4C) alkoxy-(1-5C) alkyl, mono- or dialkylaminoalkyl, acylaminoalkyl, aryl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, 3-7C cycloalkyl, 3-7C cycloalkyl-(1-4C) alkyl, aralkyl, heterocycloalkyl-(1-4C) alkyl, heterocycloalkenyl-(1-4C) alkyl, heteroaralkyl, SO2R20, COOR20, CONR20R21 or COR20 (all os); R20, R21 = H or 1-8C alkyl, 2-6C alkenyl, 2-6C alkynyl, (1-4C) alkoxy-(1-5C) alkyl, mono- or dialkylaminoalkyl, acylaminoalkyl, aryl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, 3-7C cycloalkyl, 3-7C cycloalkyl-(1-4C) alkyl, aralkyl, heterocycloalkyl-(1-4C) alkyl, heterocycloalkenyl-(1-4C) alkyl or heteroaralkyl (all os); and E = spacer element covalently linking A with G, such that the number of atomic bonds along the shortest possible route through E is 2-15.
DE10064823A 2000-12-22 2000-12-22 New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension Withdrawn DE10064823A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE10064823A DE10064823A1 (en) 2000-12-22 2000-12-22 New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension
PCT/EP2001/014924 WO2002051810A2 (en) 2000-12-22 2001-12-18 Integrin receptor ligands

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10064823A DE10064823A1 (en) 2000-12-22 2000-12-22 New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension

Publications (1)

Publication Number Publication Date
DE10064823A1 true DE10064823A1 (en) 2002-06-27

Family

ID=7668842

Family Applications (1)

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DE10064823A Withdrawn DE10064823A1 (en) 2000-12-22 2000-12-22 New (hetero)aryl-substituted aliphatic carboxylic acid derivatives, useful as integrin receptor ligands for treating, e.g. atherosclerosis, restenosis, rheumatoid arthritis, cancer, osteoporosis or hypertension

Country Status (2)

Country Link
DE (1) DE10064823A1 (en)
WO (1) WO2002051810A2 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7521473B2 (en) 2004-02-25 2009-04-21 Wyeth Inhibitors of protein tyrosine phosphatase 1B
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds
US12030903B2 (en) 2020-02-18 2024-07-09 Gilead Sciences, Inc. Antiviral compounds
US12054507B2 (en) 2020-02-18 2024-08-06 Gilead Sciences, Inc. Antiviral compounds
US12116380B2 (en) 2022-08-16 2024-10-15 Gilead Sciences, Inc. Phospholipid compounds and methods of making and using the same

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0412259B1 (en) 2003-07-22 2019-08-20 Astex Therapeutics Limited 3,4-Disubstituted 1H-pyrazole compounds as cyclin-dependent kinase (CDK) modulators, their uses, process for their preparation and pharmaceutical composition
AR054425A1 (en) 2005-01-21 2007-06-27 Astex Therapeutics Ltd PIPERIDIN ADDITION SALTS 4-IL-ACID AMID 4- (2,6-DICLORO-BENZOILAMINO) 1H-PIRAZOL-3-CARBOXILICO.
US8404718B2 (en) 2005-01-21 2013-03-26 Astex Therapeutics Limited Combinations of pyrazole kinase inhibitors
US8329703B2 (en) 2005-02-15 2012-12-11 Xtl Biopharmaceuticals Ltd. Pyrazole compounds
WO2008048589A2 (en) 2006-10-13 2008-04-24 Xtl Biopharmaceuticals Ltd Compounds and methods for treatment of hcv
CN110446708B (en) 2017-07-21 2022-12-02 安塔比奥公司 Chemical compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0889877B1 (en) * 1996-03-29 2001-08-29 G.D. Searle & Co. META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS
AU748621B2 (en) * 1998-08-13 2002-06-06 Merck & Co., Inc. Integrin receptor antagonists

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7521473B2 (en) 2004-02-25 2009-04-21 Wyeth Inhibitors of protein tyrosine phosphatase 1B
US11767337B2 (en) 2020-02-18 2023-09-26 Gilead Sciences, Inc. Antiviral compounds
US12030903B2 (en) 2020-02-18 2024-07-09 Gilead Sciences, Inc. Antiviral compounds
US12054507B2 (en) 2020-02-18 2024-08-06 Gilead Sciences, Inc. Antiviral compounds
US11697666B2 (en) 2021-04-16 2023-07-11 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
US12116380B2 (en) 2022-08-16 2024-10-15 Gilead Sciences, Inc. Phospholipid compounds and methods of making and using the same

Also Published As

Publication number Publication date
WO2002051810A3 (en) 2003-03-20
WO2002051810A2 (en) 2002-07-04

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