CN102304124B - 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 - Google Patents
具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 Download PDFInfo
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- CN102304124B CN102304124B CN201110316386.3A CN201110316386A CN102304124B CN 102304124 B CN102304124 B CN 102304124B CN 201110316386 A CN201110316386 A CN 201110316386A CN 102304124 B CN102304124 B CN 102304124B
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- Prior art keywords
- compound
- low
- carbonyl
- phenyl
- dihydroquinoline
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
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Classifications
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
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- 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
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Description
受试化合物 | GR结合率(%) | 受试化合物 | GR结合率(%) |
化合物1-19 | 100 | 化合物6-57 | 100 |
化合物1-21 | 82 | 化合物6-59 | 96 |
化合物1-46 | 100 | 化合物6-75 | 100 |
化合物3-21 | 97 | 化合物6-76 | 100 |
化合物3-22 | 99 | 化合物6-77 | 100 |
化合物3-33 | 100 | 化合物6-78 | 100 |
化合物3-44 | 98 | 化合物6-79 | 100 |
化合物3-45 | 98 | 化合物12-17 | 100 |
化合物3-48 | 100 | 化合物12-19 | 100 |
化合物3-56 | 98 | 化合物12-20 | 100 |
化合物3-57 | 98 | 化合物12-21 | 100 |
化合物3-58 | 100 | 化合物12-22 | 100 |
化合物3-59 | 100 | 化合物12-25 | 100 |
化合物3-61 | 100 | 化合物12-33 | 100 |
化合物3-62 | 100 | 化合物12-42 | 99 |
化合物3-67 | 100 | 化合物12-53 | 100 |
化合物3-68 | 100 | 化合物12-54 | 100 |
化合物3-69 | 100 | 化合物12-58 | 100 |
化合物3-72 | 100 | 化合物12-67 | 100 |
化合物3-74 | 100 | 化合物12-69 | 100 |
化合物3-85 | 95 | 化合物12-73 | 100 |
化合物3-91 | 100 | 化合物12-75 | 100 |
化合物3-94 | 100 | 化合物12-76 | 100 |
化合物3-98 | 100 | 化合物14-1 | 100 |
化合物3-99 | 100 | 化合物14-11 | 100 |
化合物5-3 | 100 | 化合物14-12 | 100 |
化合物5-4 | 95 | 化合物14-13 | 100 |
化合物6-20 | 100 | 化合物14-15 | 99 |
化合物6-24 | 100 | 化合物14-21 | 99 |
化合物6-27 | 100 | 化合物14-40 | 100 |
化合物6-36 | 98 | 化合物14-41 | 100 |
化合物6-37 | 100 | 化合物14-43 | 100 |
化合物6-40 | 99 | 化合物14-45 | 100 |
化合物6-43 | 100 | 化合物14-47 | 100 |
化合物6-45 | 96 | 化合物14-48 | 100 |
化合物6-47 | 100 | 化合物15-2 | 76 |
化合物6-53 | 95 | 化合物15-7 | 100 |
Claims (15)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005266622 | 2005-09-14 | ||
JP2005-266622 | 2005-09-14 | ||
JP2006-027128 | 2006-02-03 | ||
JP2006027128 | 2006-02-03 |
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CN200680033078.7A Division CN101263119B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
Publications (2)
Publication Number | Publication Date |
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CN102304124A CN102304124A (zh) | 2012-01-04 |
CN102304124B true CN102304124B (zh) | 2014-10-22 |
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CN200680033078.7A Expired - Fee Related CN101263119B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
CN201110316386.3A Expired - Fee Related CN102304124B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
CN2011101034745A Expired - Fee Related CN102229562B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
CN201110320070.1A Expired - Fee Related CN102311385B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
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CN200680033078.7A Expired - Fee Related CN101263119B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
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CN2011101034745A Expired - Fee Related CN102229562B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
CN201110320070.1A Expired - Fee Related CN102311385B (zh) | 2005-09-14 | 2006-09-14 | 具有糖皮质激素受体结合活性的1,2-二氢喹啉衍生物 |
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Country | Link |
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US (2) | US8017775B2 (zh) |
EP (1) | EP1944290B1 (zh) |
KR (1) | KR101390094B1 (zh) |
CN (4) | CN101263119B (zh) |
AU (1) | AU2006289751A1 (zh) |
BR (1) | BRPI0615892A2 (zh) |
CA (1) | CA2621292C (zh) |
ES (1) | ES2455142T3 (zh) |
HK (2) | HK1165800A1 (zh) |
NO (1) | NO20081787L (zh) |
PL (1) | PL1944290T3 (zh) |
RU (1) | RU2008114369A (zh) |
WO (1) | WO2007032556A1 (zh) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101390094B1 (ko) | 2005-09-14 | 2014-04-28 | 산텐 세이야꾸 가부시키가이샤 | 글루코코르티코이드 수용체 결합 활성을 갖는 신규1,2-디히드로퀴놀린 유도체 |
PT1995242E (pt) | 2006-03-14 | 2012-11-22 | Santen Pharmaceutical Co Ltd | Novos derivados de 1,2,3,4-tetra-hidroquinoxalina tendo actividade de ligação ao receptor de glucocorticóides |
WO2008059866A1 (fr) | 2006-11-14 | 2008-05-22 | Santen Pharmaceutical Co., Ltd. | Nouveau dérivé 1,2-dihydroquinoline comprenant un groupe alkyle inférieur à substitution phénylamino et un groupe phényle dans lequel est introduit un ester en tant que substituants |
JP2008255112A (ja) * | 2007-03-13 | 2008-10-23 | Santen Pharmaceut Co Ltd | 2,2,4−トリメチル−6−フェニル−1,2−ジヒドロキノリン誘導体からなるグルココルチコイド受容体アゴニスト |
US8193187B2 (en) * | 2007-05-29 | 2012-06-05 | Santen Pharmaceutical Co., Ltd. | 1,2,3,4-tetrahydroquinoxaline compound with a phenyl group substituent having a sulfonic acid ester structure or a sulfonic acid amide structure introduced therein and having glucocorticoid receptor-binding activity |
US20090042936A1 (en) * | 2007-08-10 | 2009-02-12 | Ward Keith W | Compositions and Methods for Treating or Controlling Anterior-Segment Inflammation |
JP2009084273A (ja) * | 2007-09-13 | 2009-04-23 | Santen Pharmaceut Co Ltd | 1,3,3−トリメチル−7−フェニル−3,4−ジヒドロ−1h−キノキサリン−2−オン誘導体からなるグルココルチコイド受容体アゴニスト |
WO2009035068A1 (ja) * | 2007-09-13 | 2009-03-19 | Santen Pharmaceutical Co., Ltd. | 新規1,3,3-トリメチル-7-フェニル-3,4-ジヒドロ-1h-キノキサリン-2-オン誘導体 |
CA2724055C (en) * | 2008-05-12 | 2016-08-02 | Santen Pharmaceutical Co., Ltd. | Glucocorticoid receptor agonist comprising 2,2,4-trimethyl-6-phenyl-1,2 -dihydroquinoline derivatives having substituted oxy group |
US8664221B2 (en) * | 2008-09-12 | 2014-03-04 | Santen Pharmaceutical Co., Ltd. | Method for treating an inflammatory disease by administering a 1,2,3,4- tetrahydroquinoxaline compound containing a phenyl group having a sulfonic acid ester structure introduced therein as a substituent |
WO2012108455A1 (ja) | 2011-02-09 | 2012-08-16 | 参天製薬株式会社 | 3-ヒドロキシ-6H-ベンゾ[c]クロメン-6-オン誘導体およびその製造方法 |
US20120316199A1 (en) | 2011-06-07 | 2012-12-13 | Ward Keith W | Compositions and methods for treating, controlling, reducing, or ameliorating inflammatory pain |
CN104136432A (zh) * | 2012-01-20 | 2014-11-05 | 参天制药株式会社 | 1,2-二氢喹啉衍生物或其盐的工业制备方法及其制备中间体 |
RU2644944C1 (ru) * | 2017-04-06 | 2018-02-15 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Способ получения (Z)-этил 2-(4-(4-хлорфенил)-2,4-диоксо-3-(3-оксо-3,4-дигидрохиноксалин-2(1Н)-илиден)бутанамидо)-4-метил-5-фенилтиофен-3-карбоксилата |
EP3639855A4 (en) | 2017-06-16 | 2021-03-17 | The Doshisha | COMPOUNDS HAVING CASPASE INHIBITORING ACTIVITY, PHARMACEUTICAL AGENT CONTAINING THEM FOR THE TREATMENT OR PREVENTION OF SYMPTOMS, DISORDERS OR DISEASES OF CORNEAL ENDOTHELIUM, AND APPLICATION OF SUCH PHARMACEUTICAL AGENT |
CA3067332A1 (en) | 2017-06-16 | 2018-12-20 | The Doshisha | Mtor-inhibitor-containing medicine for treating or preventing ophthalmic symptoms, disorders, or diseases, and application thereof |
Citations (1)
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WO2004018429A2 (en) * | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted hihydroquinolines as glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
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ATE252560T1 (de) | 1994-12-22 | 2003-11-15 | Ligand Pharm Inc | Steroidrezeptor-modulator verbindungen und methoden |
US5693647A (en) * | 1994-12-22 | 1997-12-02 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
DK1053239T3 (da) * | 1998-02-13 | 2003-04-22 | Abbott Lab | Gluccocorticoid-selektive, anti-inflammatoriske midler |
ATE303369T1 (de) | 2000-10-30 | 2005-09-15 | Pfizer Prod Inc | Glucocorticoid rezeptor modulatoren |
US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
CA2581327A1 (en) * | 2004-07-14 | 2006-02-23 | Ligand Pharmaceuticals, Inc. | Intracellular receptor modulator compounds and methods |
KR101390094B1 (ko) | 2005-09-14 | 2014-04-28 | 산텐 세이야꾸 가부시키가이샤 | 글루코코르티코이드 수용체 결합 활성을 갖는 신규1,2-디히드로퀴놀린 유도체 |
WO2008059866A1 (fr) * | 2006-11-14 | 2008-05-22 | Santen Pharmaceutical Co., Ltd. | Nouveau dérivé 1,2-dihydroquinoline comprenant un groupe alkyle inférieur à substitution phénylamino et un groupe phényle dans lequel est introduit un ester en tant que substituants |
JP2008255112A (ja) | 2007-03-13 | 2008-10-23 | Santen Pharmaceut Co Ltd | 2,2,4−トリメチル−6−フェニル−1,2−ジヒドロキノリン誘導体からなるグルココルチコイド受容体アゴニスト |
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WO2004018429A2 (en) * | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted hihydroquinolines as glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
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Yi-Yin Ku,等."Asymmetric Synthesis of A-240610.0 via a New Atropselective Approach for Axially Chiral Biaryls with Chirality Transfer".《J. AM. CHEM. SOC.》.2002,第124卷(第16期),第4282-4286页. |
Yi-Yin Ku,等."Asymmetric Synthesis of A-240610.0 via a New Atropselective Approach for Axially Chiral Biaryls with Chirality Transfer".《J. AM. CHEM. SOC.》.2002,第124卷(第16期),第4282-4286页. * |
Also Published As
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NO20081787L (no) | 2008-06-10 |
ES2455142T3 (es) | 2014-04-14 |
US20110263589A1 (en) | 2011-10-27 |
EP1944290B1 (en) | 2013-12-04 |
CN102229562A (zh) | 2011-11-02 |
CN101263119A (zh) | 2008-09-10 |
CA2621292A1 (en) | 2007-03-22 |
US8017775B2 (en) | 2011-09-13 |
CN102229562B (zh) | 2013-11-13 |
CN102311385B (zh) | 2015-01-14 |
BRPI0615892A2 (pt) | 2011-05-31 |
RU2008114369A (ru) | 2009-10-27 |
US20090326009A1 (en) | 2009-12-31 |
EP1944290A1 (en) | 2008-07-16 |
CN101263119B (zh) | 2014-04-09 |
US8420635B2 (en) | 2013-04-16 |
WO2007032556A1 (ja) | 2007-03-22 |
HK1166072A1 (zh) | 2012-10-19 |
PL1944290T3 (pl) | 2014-07-31 |
CA2621292C (en) | 2014-05-27 |
KR20080046230A (ko) | 2008-05-26 |
HK1165800A1 (zh) | 2012-10-12 |
CN102311385A (zh) | 2012-01-11 |
KR101390094B1 (ko) | 2014-04-28 |
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CN102304124A (zh) | 2012-01-04 |
EP1944290A4 (en) | 2011-01-12 |
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