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AU7756494A - Substituted heterocyclic carboxamides, their preparation andtheir use as pharmaceuticals - Google Patents

Substituted heterocyclic carboxamides, their preparation andtheir use as pharmaceuticals

Info

Publication number
AU7756494A
AU7756494A AU77564/94A AU7756494A AU7756494A AU 7756494 A AU7756494 A AU 7756494A AU 77564/94 A AU77564/94 A AU 77564/94A AU 7756494 A AU7756494 A AU 7756494A AU 7756494 A AU7756494 A AU 7756494A
Authority
AU
Australia
Prior art keywords
preparation
pharmaceuticals
substituted heterocyclic
heterocyclic carboxamides
andtheir
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.)
Granted
Application number
AU77564/94A
Other versions
AU676775B2 (en
Inventor
Karl-Heinz Baringhaus
Martin Bickel
Georg Tschank
Klaus Weidmann
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.)
Hoechst AG
Original Assignee
Hoechst AG
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
Priority claimed from DE4337271A external-priority patent/DE4337271A1/en
Priority claimed from DE19944410881 external-priority patent/DE4410881A1/en
Priority claimed from DE19944433928 external-priority patent/DE4433928A1/en
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of AU7756494A publication Critical patent/AU7756494A/en
Application granted granted Critical
Publication of AU676775B2 publication Critical patent/AU676775B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Obesity (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention relates to compounds of the formula I <IMAGE> a process for their preparation, and their use as medicaments. In particular, the compounds are employed for the inhibition of collagen biosynthesis, as inhibitors of proline hydroxylase and as fibrosuppressants.
AU77564/94A 1993-11-02 1994-10-31 Substituted heterocyclic carboxamides, their preparation andtheir use as pharmaceuticals Ceased AU676775B2 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE4337271 1993-11-02
DE4337271A DE4337271A1 (en) 1993-11-02 1993-11-02 ubstd. heterocyclic carboxylic acid amides and their prepn.
DE4410881 1994-03-29
DE19944410881 DE4410881A1 (en) 1994-03-29 1994-03-29 Substd. heterocyclic carboxylic acid amides and their prepn.
DE19944433928 DE4433928A1 (en) 1994-09-23 1994-09-23 Substd. heterocyclic carboxylic acid amides and their prepn.
DE4433928 1994-09-23

Publications (2)

Publication Number Publication Date
AU7756494A true AU7756494A (en) 1995-05-18
AU676775B2 AU676775B2 (en) 1997-03-20

Family

ID=27205714

Family Applications (1)

Application Number Title Priority Date Filing Date
AU77564/94A Ceased AU676775B2 (en) 1993-11-02 1994-10-31 Substituted heterocyclic carboxamides, their preparation andtheir use as pharmaceuticals

Country Status (20)

Country Link
EP (1) EP0650961B1 (en)
JP (1) JPH07228571A (en)
KR (1) KR950014072A (en)
CN (1) CN1107145A (en)
AT (1) ATE149486T1 (en)
AU (1) AU676775B2 (en)
CA (1) CA2134866A1 (en)
CY (1) CY2120B1 (en)
CZ (1) CZ289356B6 (en)
DE (1) DE59401924D1 (en)
DK (1) DK0650961T3 (en)
ES (1) ES2101421T3 (en)
GR (1) GR3023174T3 (en)
HK (1) HK1006711A1 (en)
IL (1) IL111454A (en)
MY (1) MY112413A (en)
NO (1) NO301880B1 (en)
NZ (1) NZ264821A (en)
PL (1) PL179794B1 (en)
TW (1) TW399046B (en)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL135495A (en) * 1995-09-28 2002-12-01 Hoechst Ag Intermediate compounds for the preparation of substituted quinoline-2-carboxylic acid amides
DE19746287A1 (en) * 1997-10-20 1999-04-22 Hoechst Marion Roussel De Gmbh Substituted isoquinoline-2-carboxylic acid amides, their preparation and their use as medicaments
FR2803592A1 (en) * 2000-01-06 2001-07-13 Aventis Cropscience Sa NOVEL DERIVATIVES OF 3-HYDROXYPICOLINIC ACID, PROCESS FOR THEIR PREPARATION AND FUNGICIDAL COMPOSITIONS CONTAINING SAME
DE10123587B4 (en) * 2001-05-08 2005-04-07 Schering Ag Cyanoanthranylamide derivatives and their use as pharmaceuticals
DE10123573B4 (en) * 2001-05-08 2005-06-02 Schering Ag N-Oxidanthranylamide derivatives and their use as pharmaceuticals
WO2003000678A1 (en) 2001-05-08 2003-01-03 Schering Aktiengesellschaft Cyanoanthranilamide derivatives and the use thereof as medicaments
JP2005524612A (en) 2001-12-06 2005-08-18 ファイブローゲン、インコーポレーテッド Method for increasing endogenous erythropoietin (EPO)
CN101664553B (en) * 2001-12-06 2013-08-21 法布罗根股份有限公司 Stabilization of hypoxia inducible factor (HIF) alpha
EP2295060B1 (en) 2001-12-06 2018-10-31 Fibrogen, Inc. Treatment or prevention of ischemic or hypoxic conditions
US7615565B2 (en) 2002-07-31 2009-11-10 Bayer Schering Pharma Aktiengesellschaft VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines
US8124582B2 (en) 2002-12-06 2012-02-28 Fibrogen, Inc. Treatment of diabetes
US7618940B2 (en) 2002-12-06 2009-11-17 Fibrogen, Inc. Fat regulation
US8614204B2 (en) 2003-06-06 2013-12-24 Fibrogen, Inc. Enhanced erythropoiesis and iron metabolism
SI1644336T1 (en) 2003-06-06 2011-06-30 Fibrogen Inc Nitrogen-containing heteroaryl compounds and their use in increasing endogeneous erythropoietin
EP1655295A1 (en) 2004-11-03 2006-05-10 Schering Aktiengesellschaft Anthranilamide pyridinureas as VEGF receptor kinase inhibitors
US7906533B2 (en) 2004-11-03 2011-03-15 Bayer Schering Pharma Ag Nicotinamide pyridinureas as vascular endothelial growth factor (VEGF) receptor kinase inhibitors
EP1657241A1 (en) 2004-11-03 2006-05-17 Schering Aktiengesellschaft Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors
JP4792048B2 (en) 2005-03-02 2011-10-12 ファイブロゲン インコーポレイティッド Thienopyridine compounds and methods of use thereof
JP5390184B2 (en) * 2005-06-06 2014-01-15 ファイブローゲン、インコーポレーテッド Improved treatment of anemia
WO2006138511A2 (en) 2005-06-15 2006-12-28 Fibrogen, Inc. Use of hif 1alfa modulators for treatment of cancer
MX2008009581A (en) 2006-01-27 2009-01-07 Fibrogen Inc Cyanoisoquinoline compounds and methods of use thereof.
EP3124489B1 (en) 2006-04-04 2020-07-15 Fibrogen, Inc. Thiazolo-pyridine compounds as hif modulators
PL2044005T3 (en) 2006-06-26 2011-04-29 Akebia Therapeutics Inc Prolyl hydroxylase inhibitors and methods of use
WO2009002533A1 (en) 2007-06-27 2008-12-31 The Brigham And Women's Hospital, Inc. Inflammatory bowel disease therapies
EP2188252B1 (en) * 2007-09-20 2011-04-13 Amgen Inc. 1-(4-(4-benzylbenzamido)-benzyl)azetidine-3-carboxylic acid derivatives and related compounds as s1p receptor modulators for the treatment of immune disorders
CN102272117B (en) 2008-11-14 2015-06-17 菲布罗根有限公司 Thiochromene derivatives as hip hydroxylase inhibitors
KR101007675B1 (en) * 2010-08-13 2011-01-13 김병두 Plasma spray gun with auxiliary cap and plasma spray system using the same
KR101007674B1 (en) * 2010-08-13 2011-01-13 김병두 High speed spray gun and coating device with auxiliary cap
NO2686520T3 (en) 2011-06-06 2018-03-17
CA2866556C (en) 2012-03-09 2020-01-07 Fibrogen, Inc. 4 -hydroxy-isoquinoline compounds as hif hydroxylase inhibitors
HUE037765T2 (en) 2012-07-04 2018-09-28 Agro Kanesho Co Ltd 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
SI3470397T1 (en) 2012-07-16 2022-07-29 Fibrogen, Inc. Crystalline forms of a prolyl hydroxylase inhibitor
KR102145272B1 (en) 2012-07-16 2020-08-18 피브로겐, 인크. Process for making isoquinoline compounds
US8883823B2 (en) 2012-07-16 2014-11-11 Fibrogen, Inc. Crystalline forms of a prolyl hydroxylase inhibitor
TWI685487B (en) 2013-01-24 2020-02-21 美商費比羅根公司 Crystalline forms of {[1-cyano-5-(4-chlorophenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-acetic acid
CN111728951A (en) 2013-06-06 2020-10-02 菲布罗根有限公司 Pharmaceutical formulations of HIF hydroxylase inhibitors
CA2914662C (en) 2013-06-13 2022-05-31 Robert Shalwitz Compositions and methods for treating anemia
CR20200220A (en) 2013-11-15 2020-11-18 Akebia Therapeutics Inc Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof
US10150734B2 (en) 2015-01-23 2018-12-11 Akebia Therapeutics, Inc. Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof
CN106146395B (en) * 2015-03-27 2019-01-01 沈阳三生制药有限责任公司 3- hydroxypyridine compound, preparation method and its pharmaceutical applications
KR20240038132A (en) 2015-04-01 2024-03-22 아케비아 테라퓨틱스 인코포레이티드 Compositions and methods for treating anemia
CA3097219A1 (en) 2018-05-09 2019-11-14 Akebia Therapeutics, Inc. Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid
CA3106385A1 (en) * 2018-09-13 2020-03-19 Kissei Pharmaceutical Co., Ltd. Imidazopyridinone compound
US11524939B2 (en) 2019-11-13 2022-12-13 Akebia Therapeutics, Inc. Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4015255A1 (en) 1990-05-12 1991-11-14 Hoechst Ag OXALYL-AMINOSA-E-LEED DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICAMENT FOR INHIBITING THE PROLYL HYDROXYLASE
EP0541042A1 (en) * 1991-11-05 1993-05-12 Hoechst Aktiengesellschaft 2,4- and 2,5-pyridine-dicarboxylic acid derivatives, process for their preparation and their use
JPH07504654A (en) * 1992-03-11 1995-05-25 ナルヘックス　リミテッド Amine derivatives of oxo- and hydroxy-substituted hydrocarbons
TW352384B (en) * 1992-03-24 1999-02-11 Hoechst Ag Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals

Also Published As

Publication number Publication date
KR950014072A (en) 1995-06-15
TW399046B (en) 2000-07-21
NZ264821A (en) 1997-02-24
IL111454A0 (en) 1994-12-29
EP0650961B1 (en) 1997-03-05
CN1107145A (en) 1995-08-23
CZ289356B6 (en) 2002-01-16
GR3023174T3 (en) 1997-07-30
DK0650961T3 (en) 1997-09-15
ATE149486T1 (en) 1997-03-15
DE59401924D1 (en) 1997-04-10
NO301880B1 (en) 1997-12-22
AU676775B2 (en) 1997-03-20
HK1006711A1 (en) 1999-03-12
PL179794B1 (en) 2000-10-31
NO944162L (en) 1995-05-03
IL111454A (en) 2001-08-08
CZ268394A3 (en) 1995-05-17
EP0650961A1 (en) 1995-05-03
JPH07228571A (en) 1995-08-29
CY2120B1 (en) 2002-04-26
CA2134866A1 (en) 1995-05-03
MY112413A (en) 2001-06-30
ES2101421T3 (en) 1997-07-01
NO944162D0 (en) 1994-11-01
PL305646A1 (en) 1995-05-15

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Legal Events

Date Code Title Description
MK14 Patent ceased section 143(a) (annual fees not paid) or expired