KR102127939B1 - 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴 - Google Patents
선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴 Download PDFInfo
- Publication number
- KR102127939B1 KR102127939B1 KR1020157003959A KR20157003959A KR102127939B1 KR 102127939 B1 KR102127939 B1 KR 102127939B1 KR 1020157003959 A KR1020157003959 A KR 1020157003959A KR 20157003959 A KR20157003959 A KR 20157003959A KR 102127939 B1 KR102127939 B1 KR 102127939B1
- Authority
- KR
- South Korea
- Prior art keywords
- mmol
- indole
- trifluoromethyl
- carbonitrile
- methyl
- 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.)
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- 0 *C(CC1c2c3*)[C@]1N(C(*)(*)*)c2ccc3C#N Chemical compound *C(CC1c2c3*)[C@]1N(C(*)(*)*)c2ccc3C#N 0.000 description 1
- HPARFQNSNPVVPU-UHFFFAOYSA-N C#Cc(c(F)ccc1C#N)c1C#N Chemical compound C#Cc(c(F)ccc1C#N)c1C#N HPARFQNSNPVVPU-UHFFFAOYSA-N 0.000 description 1
- LYONXIBQMPXJSL-UHFFFAOYSA-N CC(C(C)(C)O)[n](c(C(F)F)cc1c2C#N)c1ccc2C#N Chemical compound CC(C(C)(C)O)[n](c(C(F)F)cc1c2C#N)c1ccc2C#N LYONXIBQMPXJSL-UHFFFAOYSA-N 0.000 description 1
- XUBMVHIMUATVQU-UHFFFAOYSA-N CC(C)(C(C)(C)O)[n](ccc1c2Cl)c1ccc2C#N Chemical compound CC(C)(C(C)(C)O)[n](ccc1c2Cl)c1ccc2C#N XUBMVHIMUATVQU-UHFFFAOYSA-N 0.000 description 1
- RNBVAGFCAZYDFR-UHFFFAOYSA-N CC(CSC)[n](c(C)cc1c2C(F)(F)F)c1ccc2C#N Chemical compound CC(CSC)[n](c(C)cc1c2C(F)(F)F)c1ccc2C#N RNBVAGFCAZYDFR-UHFFFAOYSA-N 0.000 description 1
- QHCQYGFKDSEJQF-UHFFFAOYSA-N CC(CSC)[n](ccc1c2C(F)(F)F)c1ccc2C#N Chemical compound CC(CSC)[n](ccc1c2C(F)(F)F)c1ccc2C#N QHCQYGFKDSEJQF-UHFFFAOYSA-N 0.000 description 1
- RJQQAAMUEHNMSQ-UHFFFAOYSA-N CCC(C(C)(C)O)N Chemical compound CCC(C(C)(C)O)N RJQQAAMUEHNMSQ-UHFFFAOYSA-N 0.000 description 1
- LTAWDXBPZZKCBI-UHFFFAOYSA-N CCC(C(C)(C)O)[n](ccc1c2C(F)(F)F)c1ccc2C#N Chemical compound CCC(C(C)(C)O)[n](ccc1c2C(F)(F)F)c1ccc2C#N LTAWDXBPZZKCBI-UHFFFAOYSA-N 0.000 description 1
- SDMGKVKBQKZCCL-UHFFFAOYSA-N CCC(C(OC)=O)[n](ccc1c2C(F)(F)F)c1ccc2C#N Chemical compound CCC(C(OC)=O)[n](ccc1c2C(F)(F)F)c1ccc2C#N SDMGKVKBQKZCCL-UHFFFAOYSA-N 0.000 description 1
- UQHKCPZMKDHRQU-UHFFFAOYSA-N CCC(c1cc(C#N)ccc1)[n](ccc1c2C(F)(F)F)c1ccc2C#N Chemical compound CCC(c1cc(C#N)ccc1)[n](ccc1c2C(F)(F)F)c1ccc2C#N UQHKCPZMKDHRQU-UHFFFAOYSA-N 0.000 description 1
- ZEIZKWWYQJOIHU-UHFFFAOYSA-N CCCc1cc2c(C(F)(F)F)c(C#N)ccc2[n]1C(C)C(C)(C)O Chemical compound CCCc1cc2c(C(F)(F)F)c(C#N)ccc2[n]1C(C)C(C)(C)O ZEIZKWWYQJOIHU-UHFFFAOYSA-N 0.000 description 1
- HLZKHALITFFSBC-GOSISDBHSA-N CC[C@H](c1cc(C#N)cnc1)[n](ccc1c2C#N)c1ccc2C#N Chemical compound CC[C@H](c1cc(C#N)cnc1)[n](ccc1c2C#N)c1ccc2C#N HLZKHALITFFSBC-GOSISDBHSA-N 0.000 description 1
- FJBVHQWKWFCOIJ-HNNXBMFYSA-N C[C@@H](C(OC)=O)N(Cc1ccccc1)Cc1ccccc1 Chemical compound C[C@@H](C(OC)=O)N(Cc1ccccc1)Cc1ccccc1 FJBVHQWKWFCOIJ-HNNXBMFYSA-N 0.000 description 1
- SKDVMPZQJMZEAC-SECBINFHSA-N C[C@H](CS(C)(=O)=O)[n](ccc1c2C(F)(F)F)c1ccc2C#N Chemical compound C[C@H](CS(C)(=O)=O)[n](ccc1c2C(F)(F)F)c1ccc2C#N SKDVMPZQJMZEAC-SECBINFHSA-N 0.000 description 1
- JUHNPHRIRBQQRV-UHFFFAOYSA-N Cc(c(F)ccc1S)c1Br Chemical compound Cc(c(F)ccc1S)c1Br JUHNPHRIRBQQRV-UHFFFAOYSA-N 0.000 description 1
- DAKOVCWDJHXVTB-UHFFFAOYSA-N N#Cc(ccc(F)c1I)c1Cl Chemical compound N#Cc(ccc(F)c1I)c1Cl DAKOVCWDJHXVTB-UHFFFAOYSA-N 0.000 description 1
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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- 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
- 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
Landscapes
- 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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261672455P | 2012-07-17 | 2012-07-17 | |
| US61/672,455 | 2012-07-17 | ||
| US201361748874P | 2013-01-04 | 2013-01-04 | |
| US61/748,874 | 2013-01-04 | ||
| PCT/IB2013/001530 WO2014013309A1 (en) | 2012-07-17 | 2013-07-15 | Indolecarbonitriles as selective androgen receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150032333A KR20150032333A (ko) | 2015-03-25 |
| KR102127939B1 true KR102127939B1 (ko) | 2020-06-29 |
Family
ID=49117887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157003959A Active KR102127939B1 (ko) | 2012-07-17 | 2013-07-15 | 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴 |
Country Status (39)
Families Citing this family (8)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050222148A1 (en) | 2004-03-30 | 2005-10-06 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| WO2005118539A1 (en) | 2004-06-01 | 2005-12-15 | F.Hoffmann-La Roche Ag | 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitor |
| WO2007108936A2 (en) | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| 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 |
Family Cites Families (19)
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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2013
- 2013-07-15 CN CN201380048232.8A patent/CN104619693B/zh active Active
- 2013-07-15 PT PT137589750T patent/PT2875013T/pt unknown
- 2013-07-15 ES ES13758975.0T patent/ES2657912T3/es active Active
- 2013-07-15 KR KR1020157003959A patent/KR102127939B1/ko active Active
- 2013-07-15 TW TW102125297A patent/TWI574946B/zh active
- 2013-07-15 PE PE2015000039A patent/PE20150371A1/es active IP Right Grant
- 2013-07-15 BR BR112015000940-9A patent/BR112015000940B1/pt active IP Right Grant
- 2013-07-15 JO JOP/2013/0214A patent/JO3384B1/ar active
- 2013-07-15 WO PCT/IB2013/001530 patent/WO2014013309A1/en not_active Ceased
- 2013-07-15 HR HRP20180061TT patent/HRP20180061T1/hr unknown
- 2013-07-15 AU AU2013291721A patent/AU2013291721B2/en active Active
- 2013-07-15 UY UY0001034911A patent/UY34911A/es not_active Application Discontinuation
- 2013-07-15 ME MEP-2018-16A patent/ME02996B/me unknown
- 2013-07-15 MY MYPI2018001949A patent/MY198512A/en unknown
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