CN104619693B - 作为选择性雄激素受体调节剂的吲哚腈类 - Google Patents

作为选择性雄激素受体调节剂的吲哚腈类 Download PDF

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CN104619693B
CN104619693B CN201380048232.8A CN201380048232A CN104619693B CN 104619693 B CN104619693 B CN 104619693B CN 201380048232 A CN201380048232 A CN 201380048232A CN 104619693 B CN104619693 B CN 104619693B
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indole
mmol
trifluoromethyl
carbonitrile
mixture
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CN104619693A (zh
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P.S.特恩布尔
R.卡迪拉
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GlaxoSmithKline Intellectual Property No 2 Ltd
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    • 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
    • C07D209/24—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 alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • 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
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06—Anabolic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26—Androgens
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • 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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Endocrinology (AREA)
  • Neurology (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hospice & Palliative Care (AREA)
  • Pulmonology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
CN201380048232.8A 2012-07-17 2013-07-15 作为选择性雄激素受体调节剂的吲哚腈类 Active CN104619693B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261672455P 2012-07-17 2012-07-17
US61/672455 2012-07-17
US201361748874P 2013-01-04 2013-01-04
US61/748874 2013-01-04
PCT/IB2013/001530 WO2014013309A1 (en) 2012-07-17 2013-07-15 Indolecarbonitriles as selective androgen receptor modulators

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CN104619693A CN104619693A (zh) 2015-05-13
CN104619693B true CN104619693B (zh) 2019-08-13

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Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10155099B2 (en) 2009-09-21 2018-12-18 Cook Regentec Llc Method for infusing stem cells
CN104619693B (zh) 2012-07-17 2019-08-13 葛兰素史克知识产权第二有限公司 作为选择性雄激素受体调节剂的吲哚腈类
WO2015110958A1 (en) * 2014-01-21 2015-07-30 Glaxosmithkline Intellectual Property (No.2) Limited Crystalline forms of (r)-1 -(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)indoline-5-carbonitrile
KR20190077607A (ko) * 2014-10-16 2019-07-03 지티엑스, 인코포레이티드 Sarm을 이용하는 비뇨기 장애의 치료 방법
CN105130872B (zh) * 2015-08-25 2018-01-30 江西师范大学 一种3位三氟甲基取代吲哚的制备方法
CN110437125B (zh) * 2019-09-06 2021-03-12 苏州旺山旺水生物医药有限公司 一种Tezacaftor中间体II的制备方法
WO2022204235A1 (en) * 2021-03-23 2022-09-29 Nido Biosciences, Inc. Bicyclic compounds as androgen receptor modulators
CN115010574B (zh) * 2022-06-06 2024-01-05 爱斯特（成都）生物制药股份有限公司 1-溴-2-氯-4-氟-2碘苯的合成方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1960973A (zh) * 2004-03-30 2007-05-09 惠氏公司 作为去甲肾上腺素(ne)与血清素(5－h t)活性和单胺重摄取的调控剂以治疗血管舒缩症状(vms)的1－(1h－吲哚－1－基)－3－(4－甲基哌嗪－1－基)－1－苯基丙烷－2－醇衍生物和相关化合物
CN1993321A (zh) * 2004-06-01 2007-07-04 弗·哈夫曼-拉罗切有限公司 作为单胺再摄取抑制剂的3－氨基－1－芳基丙基吲哚类化合物
WO2008042571A2 (en) * 2006-09-29 2008-04-10 Smithkline Beecham Corporation Substituted indole compounds
CN101426778A (zh) * 2006-03-15 2009-05-06 惠氏公司 作为组胺-3拮抗剂的n-经取代-氮杂环基胺
WO2010118287A1 (en) * 2009-04-10 2010-10-14 Radius Health, Inc. Selective androgen receptor modulators

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ID27280A (id) 1998-02-25 2001-03-22 Genetics Inst Inhibitor-inhibitor dari enzim-enzim fosfolipase
AU3951899A (en) * 1998-06-19 2000-01-05 Pfizer Products Inc. Pyrrolo(2,3-d)pyrimidine compounds
US6576265B1 (en) 1999-12-22 2003-06-10 Acell, Inc. Tissue regenerative composition, method of making, and method of use thereof
ES2471240T3 (es) 2002-05-24 2014-06-25 Bayer Cropscience Ag Procedimiento de preparación de derivados de tioalquilamina
US7517899B2 (en) * 2004-03-30 2009-04-14 Wyeth Phenylaminopropanol derivatives and methods of their use
CA2564953A1 (en) 2004-05-03 2005-11-24 Janssen Pharmaceutica N.V. Novel indole derivatives as selective androgen receptor modulators (sarms)
WO2005111028A1 (en) 2004-05-03 2005-11-24 Janssen Pharmaceutica N.V. Novel indole derivatives as selective androgen receptor modulators (sarms)
ATE525354T1 (de) 2004-05-03 2011-10-15 Janssen Pharmaceutica Nv Benzofuranderivate als selektive androgenrezeptormodulatoren (sarms)
WO2007012953A2 (en) * 2005-07-29 2007-02-01 Pfizer Products Inc. Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis
GB0526246D0 (en) * 2005-12-22 2006-02-01 Novartis Ag Organic compounds
WO2007108936A2 (en) 2006-03-15 2007-09-27 Wyeth N-substituted-azacyclylamines as histamine-3 antagonists
RS53382B (sr) * 2008-08-20 2014-10-31 Zoetis Llc Jedinjenja pirol [2,3-d]pirimidina
US9095572B2 (en) 2009-01-09 2015-08-04 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
AU2010308028A1 (en) * 2009-10-15 2012-04-19 Pfizer Inc. Pyrrolo[2,3-d] pyrimidine compounds
CA2782720A1 (en) * 2009-12-18 2011-06-23 Pfizer Inc. Pyrrolo[2,3-d]pyrimidine compounds
RU2598842C2 (ru) * 2011-01-20 2016-09-27 Мерк Шарп Энд Домэ Корп. Антагонисты рецептора минералокортикоидов
JP6075736B2 (ja) * 2011-12-21 2017-02-08 ジエンス ヘンルイ メデイシンカンパニー リミテッドＪｉａｎｇｓｕ Ｈｅｎｇｒｕｉ Ｍｅｄｉｃｉｎｅ Ｃｏ．，Ｌｔｄ． ピロール−６員ヘテロアリール環誘導体、その合成法およびその医薬用途
CN104619693B (zh) * 2012-07-17 2019-08-13 葛兰素史克知识产权第二有限公司 作为选择性雄激素受体调节剂的吲哚腈类
WO2015110958A1 (en) * 2014-01-21 2015-07-30 Glaxosmithkline Intellectual Property (No.2) Limited Crystalline forms of (r)-1 -(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)indoline-5-carbonitrile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1960973A (zh) * 2004-03-30 2007-05-09 惠氏公司 作为去甲肾上腺素(ne)与血清素(5－h t)活性和单胺重摄取的调控剂以治疗血管舒缩症状(vms)的1－(1h－吲哚－1－基)－3－(4－甲基哌嗪－1－基)－1－苯基丙烷－2－醇衍生物和相关化合物
CN1993321A (zh) * 2004-06-01 2007-07-04 弗·哈夫曼-拉罗切有限公司 作为单胺再摄取抑制剂的3－氨基－1－芳基丙基吲哚类化合物
CN101426778A (zh) * 2006-03-15 2009-05-06 惠氏公司 作为组胺-3拮抗剂的n-经取代-氮杂环基胺
WO2008042571A2 (en) * 2006-09-29 2008-04-10 Smithkline Beecham Corporation Substituted indole compounds
WO2010118287A1 (en) * 2009-04-10 2010-10-14 Radius Health, Inc. Selective androgen receptor modulators

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BR112015000940B1 (pt) 2022-05-17
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CL2015000119A1 (es) 2015-04-24
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EA026371B1 (ru) 2017-03-31
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JP2015522603A (ja) 2015-08-06
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DOP2015000004A (es) 2015-03-15
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US10710963B2 (en) 2020-07-14
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CR20150008A (es) 2015-03-09
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NZ703129A (en) 2017-06-30
TW201416349A (zh) 2014-05-01
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US11299457B2 (en) 2022-04-12
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