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

Info

Publication number
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
Authority
CN
China
Prior art keywords
indole
mmol
trifluoromethyl
carbonitrile
mixture
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.)
Active
Application number
CN201380048232.8A
Other languages
English (en)
Chinese (zh)
Other versions
CN104619693A (zh
Inventor
P.S.特恩布尔
R.卡迪拉
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.)
GlaxoSmithKline Intellectual Property No 2 Ltd
Original Assignee
GlaxoSmithKline Intellectual Property No 2 Ltd
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=49117887&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN104619693(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by GlaxoSmithKline Intellectual Property No 2 Ltd filed Critical GlaxoSmithKline Intellectual Property No 2 Ltd
Publication of CN104619693A publication Critical patent/CN104619693A/zh
Application granted granted Critical
Publication of CN104619693B publication Critical patent/CN104619693B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C07D209/24—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (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)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (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

Publications (2)

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

Family

ID=49117887

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201380048232.8A Active CN104619693B (zh) 2012-07-17 2013-07-15 作为选择性雄激素受体调节剂的吲哚腈类

Country Status (39)

Country Link
US (5) US8957104B2 (https=)
EP (1) EP2875013B1 (https=)
JP (1) JP6106746B2 (https=)
KR (1) KR102127939B1 (https=)
CN (1) CN104619693B (https=)
AR (1) AR091770A1 (https=)
AU (1) AU2013291721B2 (https=)
BR (1) BR112015000940B1 (https=)
CA (1) CA2879104C (https=)
CL (1) CL2015000119A1 (https=)
CO (1) CO7240378A2 (https=)
CR (1) CR20150008A (https=)
CY (1) CY1120064T1 (https=)
DK (1) DK2875013T3 (https=)
DO (1) DOP2015000004A (https=)
EA (1) EA026371B8 (https=)
ES (1) ES2657912T3 (https=)
HR (1) HRP20180061T1 (https=)
HU (1) HUE036238T2 (https=)
IL (1) IL236448A (https=)
IN (1) IN2014KN02993A (https=)
JO (1) JO3384B1 (https=)
LT (1) LT2875013T (https=)
ME (1) ME02996B (https=)
MX (1) MX349943B (https=)
MY (2) MY173845A (https=)
NZ (1) NZ703129A (https=)
PE (1) PE20150371A1 (https=)
PH (1) PH12015500104B1 (https=)
PL (1) PL2875013T3 (https=)
PT (1) PT2875013T (https=)
RS (1) RS56810B1 (https=)
SG (1) SG11201408493WA (https=)
SI (1) SI2875013T1 (https=)
SM (1) SMT201800115T1 (https=)
TW (1) TWI574946B (https=)
UY (1) UY34911A (https=)
WO (1) WO2014013309A1 (https=)
ZA (1) ZA201500096B (https=)

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
KR102127939B1 (ko) * 2012-07-17 2020-06-29 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴
EP3097077A1 (en) * 2014-01-21 2016-11-30 Glaxosmithkline Intellectual Property (No. 2) Limited Crystalline forms of (r)-1 -(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)indoline-5-carbonitrile
MX2017004819A (es) * 2014-10-16 2018-06-12 Gtx Inc Metodos de tratamiento de transtornos urológicos usando sarm.
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
EE200000486A (et) 1998-02-25 2002-02-15 Genetics Institute, Inc. Fosfolipaasensüümide inhibiitorid, neid sisaldav farmatseutiline kompositsioon ning meetod põletikulise reaktsiooni raviks imetajal
BR9911365A (pt) * 1998-06-19 2001-03-13 Pfizer Prod Inc Compostos pirrolo[2,3-d]pirimidina
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
CN1980917B (zh) 2004-05-03 2014-02-12 詹森药业有限公司 作为选择性雄激素受体调节剂（sarms）的新的吲哚衍生物
CN1980891B (zh) 2004-05-03 2011-03-09 詹森药业有限公司 作为选择性雄激素受体调节剂(sarms)的吲哚、苯并呋喃和苯并噻吩衍生物
US7427682B2 (en) 2004-05-03 2008-09-23 Janssen Pharmaceutica N.V. Indole derivatives as selective androgen receptor modulators (SARMS)
BRPI0613876A2 (pt) * 2005-07-29 2011-02-15 Pfizer Prod Inc derivados de pirrolo [2,3-d] pirimidina; seus intermediários e sìntese
GB0526246D0 (en) * 2005-12-22 2006-02-01 Novartis Ag Organic compounds
BRPI0709612A2 (pt) * 2006-03-15 2011-07-19 Wyeth Corp composto de fórmula i; método para o tratamento de um distúrbio no sistema nervoso central relacionado ou afetado pelo receptor histamina-3 em um paciente que necessita deste tratamento; método para a inibição do receptor h3; composição farmacêutica; e processo para a preparação de um composto de fórmula i
JP4884570B2 (ja) * 2008-08-20 2012-02-29 ファイザー・インク ピロロ［２，３−ｄ］ピリミジン化合物
US9095572B2 (en) 2009-01-09 2015-08-04 Board Of Regents Of The University Of Texas System Pro-neurogenic compounds
CA2776028C (en) * 2009-10-15 2015-12-01 Pfizer Inc. Pyrrolo[2,3-d]pyrimidine compounds
ES2461967T3 (es) * 2009-12-18 2014-05-21 Pfizer Inc. Compuestos de pirrolo[2,3-d]pirimidina
RU2598842C2 (ru) * 2011-01-20 2016-09-27 Мерк Шарп Энд Домэ Корп. Антагонисты рецептора минералокортикоидов
KR102032934B1 (ko) * 2011-12-21 2019-10-16 지앙수 헨그루이 메디슨 컴퍼니 리미티드 피롤 6원 헤테로아릴 고리 유도체, 그의 제조 방법, 및 그의 의약 용도
KR102127939B1 (ko) * 2012-07-17 2020-06-29 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴
EP3097077A1 (en) * 2014-01-21 2016-11-30 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

Also Published As

Publication number Publication date
ZA201500096B (en) 2017-07-26
JP2015522603A (ja) 2015-08-06
AU2013291721B2 (en) 2016-02-25
MX349943B (es) 2017-08-21
EP2875013A1 (en) 2015-05-27
AU2013291721A1 (en) 2015-02-26
PH12015500104A1 (en) 2015-03-02
US20140024694A1 (en) 2014-01-23
HRP20180061T1 (hr) 2018-02-23
US20190127326A1 (en) 2019-05-02
SI2875013T1 (en) 2018-03-30
AR091770A1 (es) 2015-02-25
US20200270210A1 (en) 2020-08-27
CN104619693A (zh) 2015-05-13
CO7240378A2 (es) 2015-04-17
US20150080449A1 (en) 2015-03-19
PL2875013T3 (pl) 2018-06-29
MX2015000825A (es) 2015-07-17
KR20150032333A (ko) 2015-03-25
US10196353B2 (en) 2019-02-05
US8957104B2 (en) 2015-02-17
KR102127939B1 (ko) 2020-06-29
IL236448A0 (en) 2015-02-26
PT2875013T (pt) 2018-02-28
MY198512A (en) 2023-09-01
SG11201408493WA (en) 2015-02-27
ME02996B (me) 2018-10-20
BR112015000940B1 (pt) 2022-05-17
CA2879104C (en) 2020-08-25
US10710963B2 (en) 2020-07-14
CY1120064T1 (el) 2018-12-12
UY34911A (es) 2014-02-28
CA2879104A1 (en) 2014-01-23
JO3384B1 (ar) 2019-03-13
ES2657912T3 (es) 2018-03-07
US20170073309A1 (en) 2017-03-16
US9533948B2 (en) 2017-01-03
DOP2015000004A (es) 2015-03-15
EA201492237A1 (ru) 2015-06-30
IN2014KN02993A (https=) 2015-05-08
LT2875013T (lt) 2018-02-26
EA026371B1 (ru) 2017-03-31
CL2015000119A1 (es) 2015-04-24
SMT201800115T1 (it) 2018-03-08
PH12015500104B1 (en) 2015-03-02
CR20150008A (es) 2015-03-09
PE20150371A1 (es) 2015-03-27
NZ703129A (en) 2017-06-30
TW201416349A (zh) 2014-05-01
US11299457B2 (en) 2022-04-12
BR112015000940A2 (pt) 2017-06-27
EP2875013B1 (en) 2017-11-29
RS56810B1 (sr) 2018-04-30
HUE036238T2 (hu) 2018-06-28
MY173845A (en) 2020-02-24
DK2875013T3 (en) 2018-01-22
WO2014013309A1 (en) 2014-01-23
IL236448A (en) 2016-10-31
JP6106746B2 (ja) 2017-04-05
TWI574946B (zh) 2017-03-21
HK1208867A1 (en) 2016-03-18
EA026371B8 (ru) 2017-06-30

Similar Documents

Publication Publication Date Title
CN104619693B (zh) 作为选择性雄激素受体调节剂的吲哚腈类
JP2008515998A (ja) 化合物
JP2007526336A (ja) 選択的アンドロゲン受容体モジュレーターとしてのアニリン誘導体
US11001556B2 (en) Crystalline forms
HK1208867B (en) Indolecarbonitriles as selective androgen receptor modulators
UA112898C2 (uk) Індолкарбонітрили як селективні модулятори андрогенного рецептора
KR20150139917A (ko) 고나도트로핀-방출 호르몬 수용체 길항제로서 사용하기 위한 스피로인돌린 유도체

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CP03 Change of name, title or address
CP03 Change of name, title or address

Address after: Steve Niki

Patentee after: GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) Ltd.

Country or region after: Britain

Address before: The Middlesex County

Patentee before: GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) Ltd.

Country or region before: Britain