CN100384852C - 作为糖原磷酸化酶抑制剂的杂环酰胺衍生物 - Google Patents
作为糖原磷酸化酶抑制剂的杂环酰胺衍生物 Download PDFInfo
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- CN100384852C CN100384852C CNB038102145A CN03810214A CN100384852C CN 100384852 C CN100384852 C CN 100384852C CN B038102145 A CNB038102145 A CN B038102145A CN 03810214 A CN03810214 A CN 03810214A CN 100384852 C CN100384852 C CN 100384852C
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- China
- Prior art keywords
- oxo
- pyrroles
- thieno
- chloro
- tetrahydroquinoline
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008275 solid aerosol Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 239000012622 synthetic inhibitor Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
- QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
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| GBGB0205165.4A GB0205165D0 (en) | 2002-03-06 | 2002-03-06 | Chemical compounds |
| GB0205165.4 | 2002-03-06 |
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| CN1653070A CN1653070A (zh) | 2005-08-10 |
| CN100384852C true CN100384852C (zh) | 2008-04-30 |
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| BR (1) | BR0308146A (enExample) |
| CA (1) | CA2477667A1 (enExample) |
| GB (1) | GB0205165D0 (enExample) |
| IL (1) | IL163803A0 (enExample) |
| MX (1) | MXPA04008614A (enExample) |
| NO (1) | NO20043852L (enExample) |
| NZ (1) | NZ534990A (enExample) |
| PL (1) | PL372973A1 (enExample) |
| TW (1) | TW200305412A (enExample) |
| WO (1) | WO2003074532A1 (enExample) |
| ZA (1) | ZA200406679B (enExample) |
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| CA2495943C (en) * | 2002-08-29 | 2009-07-21 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| GB0222909D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222912D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0320422D0 (en) * | 2003-08-30 | 2003-10-01 | Astrazeneca Ab | Chemical compounds |
| AU2004312530A1 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| US7498341B2 (en) * | 2004-01-31 | 2009-03-03 | Sanofi Aventis Deutschland Gmbh | Heterocyclically substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| US7402674B2 (en) | 2004-01-31 | 2008-07-22 | Sanofi-Aventis Deutschland Gmbh, | 7-Phenylamino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| US7470706B2 (en) | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| DE102004004971B3 (de) * | 2004-01-31 | 2005-09-15 | Aventis Pharma Deutschland Gmbh | Cycloalkyl substituierte 7-Amino-4-chinolon-3-carbonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arnzeimittel |
| ATE438645T1 (de) * | 2004-01-31 | 2009-08-15 | Sanofi Aventis Deutschland | 7-phenylamino-4-chinolon-3-carbonsäure-derivate verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| WO2006053274A2 (en) | 2004-11-15 | 2006-05-18 | Bristol-Myers Squibb Company | 2-amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7226942B2 (en) | 2004-11-15 | 2007-06-05 | Bristol-Myers Squibb Company | 2-amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7365061B2 (en) | 2004-11-15 | 2008-04-29 | Bristol-Myers Squibb Company | 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7223786B2 (en) | 2004-11-15 | 2007-05-29 | Bristol-Myers Squibb Company | 2-aminonaphthalene derivatives and related glycogen phosphorylase inhibitors |
| WO2006076598A2 (en) * | 2005-01-12 | 2006-07-20 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid receptor modulators |
| DE102005063244A1 (de) * | 2005-12-21 | 2007-06-28 | Eberhard-Karls-Universität Tübingen | Modifiziertes 2-Nitroimidazol-Derivat |
| KR101294014B1 (ko) | 2006-01-06 | 2013-08-09 | 선오비온 파마슈티컬스 인코포레이티드 | 모노아민 재흡수 저해제로서의 시클로알킬아민 |
| JP5438975B2 (ja) | 2006-01-06 | 2014-03-12 | サノビオン ファーマシューティカルズ インク | テトラロン系モノアミン再取り込み阻害剤 |
| WO2007082026A2 (en) * | 2006-01-10 | 2007-07-19 | The Trustees Of Boston College | Catalytic enantioselective silylations of substrates |
| CA2648121C (en) | 2006-03-31 | 2013-08-06 | Sepracor Inc. | Preparation of chiral amides and amines |
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| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| BRPI0811639A2 (pt) | 2007-05-31 | 2014-09-30 | Sepracor Inc | Cicloaquilaminas fenil substituídas como inibidores da recaptação de monoamina |
| SG10201406631TA (en) * | 2009-10-16 | 2014-11-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EA201270568A1 (ru) | 2009-10-16 | 2012-11-30 | Риб-Экс Фармасьютикалз, Инк. | Антимикробные композиции и способы их получения и применения |
| JP2018507881A (ja) | 2015-03-11 | 2018-03-22 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物化合物ならびにこれらを作製および使用する方法 |
| EP3452479A1 (en) | 2016-05-06 | 2019-03-13 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| CN109553580B (zh) * | 2017-09-25 | 2023-08-11 | 南京长澳医药科技有限公司 | 硝基咪唑类化合物中间体及其盐的制备方法 |
| CN112442022B (zh) * | 2019-09-02 | 2022-05-20 | 承德医学院 | 苯并嗪-4-酮类化合物、其制备方法及医药用途 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
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| EP1088824A2 (en) * | 1999-09-30 | 2001-04-04 | Pfizer Products Inc. | Bicyclic pyrrolyl amides as glycogen phosphorylase inhibitors |
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2002
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- 2003-03-04 NZ NZ534990A patent/NZ534990A/en unknown
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- 2003-03-04 AU AU2003214377A patent/AU2003214377A1/en not_active Abandoned
- 2003-03-04 JP JP2003573000A patent/JP2005526058A/ja not_active Withdrawn
- 2003-03-04 CA CA002477667A patent/CA2477667A1/en not_active Abandoned
- 2003-03-04 KR KR10-2004-7013863A patent/KR20040096661A/ko not_active Ceased
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1088824A2 (en) * | 1999-09-30 | 2001-04-04 | Pfizer Products Inc. | Bicyclic pyrrolyl amides as glycogen phosphorylase inhibitors |
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| PL372973A1 (en) | 2005-08-08 |
| BR0308146A (pt) | 2004-12-07 |
| GB0205165D0 (en) | 2002-04-17 |
| CN1653070A (zh) | 2005-08-10 |
| JP2005526058A (ja) | 2005-09-02 |
| US7129249B2 (en) | 2006-10-31 |
| US7276517B2 (en) | 2007-10-02 |
| KR20040096661A (ko) | 2004-11-16 |
| AR038888A1 (es) | 2005-02-02 |
| TW200305412A (en) | 2003-11-01 |
| NZ534990A (en) | 2006-02-24 |
| AU2003214377A1 (en) | 2003-09-16 |
| CA2477667A1 (en) | 2003-09-12 |
| MXPA04008614A (es) | 2004-12-06 |
| IL163803A0 (en) | 2005-12-18 |
| US20050131015A1 (en) | 2005-06-16 |
| NO20043852L (no) | 2004-09-14 |
| ZA200406679B (en) | 2005-01-18 |
| WO2003074532A1 (en) | 2003-09-12 |
| US20070043069A1 (en) | 2007-02-22 |
| EP1483270A1 (en) | 2004-12-08 |
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