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CA2002415A1 - Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents - Google Patents

Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents

Info

Publication number
CA2002415A1
CA2002415A1 CA002002415A CA2002415A CA2002415A1 CA 2002415 A1 CA2002415 A1 CA 2002415A1 CA 002002415 A CA002002415 A CA 002002415A CA 2002415 A CA2002415 A CA 2002415A CA 2002415 A1 CA2002415 A1 CA 2002415A1
Authority
CA
Canada
Prior art keywords
trifluoromethyl
alpha
methyl
acetic acid
benzylamino
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.)
Abandoned
Application number
CA002002415A
Other languages
English (en)
French (fr)
Inventor
Gilbert A. Youngdale
John C. Sih
Steven P. Tanis
Chiu-Hong Lin
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of CA2002415A1 publication Critical patent/CA2002415A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002002415A 1988-11-14 1989-11-07 Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents Abandoned CA2002415A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US27055488A 1988-11-14 1988-11-14
US07/270,554 1988-11-14

Publications (1)

Publication Number Publication Date
CA2002415A1 true CA2002415A1 (en) 1990-05-14

Family

ID=23031777

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002002415A Abandoned CA2002415A1 (en) 1988-11-14 1989-11-07 Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents

Country Status (6)

Country Link
JP (1) JPH04501722A (ko)
KR (1) KR920701152A (ko)
AU (1) AU4649189A (ko)
CA (1) CA2002415A1 (ko)
IL (1) IL92294A0 (ko)
WO (1) WO1990005721A1 (ko)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2110574A1 (en) * 1991-06-21 1993-01-07 Lawrence I. Kruse Tryptamine analogues, their synthesis and their use as 5-ht1-like or 5-ht2 receptor agonists
US5158969A (en) * 1991-08-21 1992-10-27 Neurosearch A/S Indole derivatives as potassium channel blockers
GB9523999D0 (en) 1995-11-23 1996-01-24 Lilly Co Eli Indolyl neuropeptide y receptor antagonists
US6200957B1 (en) 1995-12-14 2001-03-13 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5780437A (en) * 1995-12-14 1998-07-14 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5849764A (en) * 1995-12-14 1998-12-15 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6197975B1 (en) 1995-12-14 2001-03-06 Merck & Co. , Inc. Antagonists of gonadotropin releasing hormone
US5756507A (en) * 1995-12-14 1998-05-26 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
CA2275394A1 (en) * 1996-12-23 1998-07-02 Merck & Co., Inc. Antidiabetic agents
US5981550A (en) * 1997-06-05 1999-11-09 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6156767A (en) * 1997-06-05 2000-12-05 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6156772A (en) * 1997-06-05 2000-12-05 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5985901A (en) * 1997-06-05 1999-11-16 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6004984A (en) * 1997-06-05 1999-12-21 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6159975A (en) * 1998-02-11 2000-12-12 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6077847A (en) * 1998-04-02 2000-06-20 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5998432A (en) * 1998-04-02 1999-12-07 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US5985892A (en) * 1998-04-02 1999-11-16 Merck & Co., Ltd. Antagonists of gonadotropin releasing hormone
US6110931A (en) * 1998-04-02 2000-08-29 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6228867B1 (en) 1998-04-02 2001-05-08 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6025366A (en) * 1998-04-02 2000-02-15 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
WO2000053185A1 (en) 1999-03-10 2000-09-14 Merck & Co., Inc. 6-azaindole compounds as antagonists of gonadotropin releasing hormone
CA2367121A1 (en) 1999-03-10 2000-09-14 Merck & Co., Inc. 6-azaindole compounds as antagonists of gonadotropin releasing hormone
JP2003526618A (ja) 1999-03-10 2003-09-09 メルク エンド カムパニー インコーポレーテッド 性腺刺激ホルモン放出ホルモン拮抗薬としての６−アザインドール化合物
IL130169A (en) * 1999-05-27 2006-08-20 Neurim Pharma 1991 Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them
PE20010580A1 (es) * 1999-09-03 2001-05-25 Takeda Chemical Industries Ltd Composicion farmaceutica para tratar la diabetes
EP1305285B1 (en) 2000-07-25 2007-05-16 Merck & Co., Inc. N-substituted indoles useful in the treatment of diabetes
US6620824B2 (en) 2001-04-11 2003-09-16 Merck & Co., Inc. Process for the synthesis of gonadotropin releasing hormone antagonists
WO2005044261A1 (en) * 2003-10-27 2005-05-19 University Of Iowa Research Foundation Melatonin analogue prodrugs
WO2005065050A2 (ja) * 2003-12-25 2005-07-21 Asahi Kasei Pharma Corporation ２環化合物
CA2582079A1 (en) 2004-09-27 2006-05-04 Organix, Inc. Indole compounds useful as serotonin selective agents
KR100807718B1 (ko) * 2006-10-17 2008-02-28 한국생명공학연구원 인돌 유도체를 유효성분으로 함유하는 대사성 질환 예방 및치료용 약학적 조성물
DE102008030206A1 (de) 2008-06-25 2009-12-31 Bayer Schering Pharma Aktiengesellschaft 3-Cyanoalky- und 3-Hydroxyalkyl-Indole und ihre Verwendung
DE102008030207A1 (de) 2008-06-25 2009-12-31 Bayer Schering Pharma Aktiengesellschaft Substituierte 7-Sulfanylmethyl-, 7-Sulfinylmethyl- und 7-Sulfonylmethyl-Indole und ihre Verwendung
CA2770724A1 (en) * 2009-08-10 2011-02-17 Galenea Corporation 5-ht inhibiting indole compounds
GB201411239D0 (en) * 2014-06-25 2014-08-06 Takeda Pharmaceutical Novel compounds
CN114601825B (zh) * 2022-02-18 2023-08-04 复旦大学附属中山医院 一种肠道菌群代谢物吲哚-3-甲醛在防治动脉粥样硬化中的应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2542869A (en) * 1948-03-19 1951-02-20 Merck & Co Inc N-pyridoxyl-amino acids and process of preparing the same
US3074942A (en) * 1958-01-13 1963-01-22 Geigy Chem Corp alpha-substituted glycine derivatives
NL125657C (ko) * 1963-11-26
GB1080470A (en) * 1963-12-31 1967-08-23 Merck & Co Inc Indole derivatives
EP0031653A1 (en) * 1979-12-19 1981-07-08 Beecham Group Plc N-Substituted alpha-amino acids, processes for making them and pharmaceutical compositions containing them
LU85035A1 (fr) * 1983-10-07 1985-06-19 Midit Derives d'amides d'acides amines,leurs preparation et utilisation ainsi que les compositions contenant ces derives

Also Published As

Publication number Publication date
WO1990005721A1 (en) 1990-05-31
JPH04501722A (ja) 1992-03-26
AU4649189A (en) 1990-06-12
KR920701152A (ko) 1992-08-11
IL92294A0 (en) 1990-07-26

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued