CA2670340C - Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators - Google Patents

Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators Download PDF

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Publication number
CA2670340C
CA2670340C CA2670340A CA2670340A CA2670340C CA 2670340 C CA2670340 C CA 2670340C CA 2670340 A CA2670340 A CA 2670340A CA 2670340 A CA2670340 A CA 2670340A CA 2670340 C CA2670340 C CA 2670340C
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CA
Canada
Prior art keywords
compound
salt
pyridin
cyclopenta
tetrahydro
Prior art date
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Active
Application number
CA2670340A
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English (en)
French (fr)
Other versions
CA2670340A1 (en
Inventor
Konstantinos Gavardinas
Jonathan Edward Green
Prabhakar Kondaji Jadhav
Donald Paul Matthews
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.)
Eli Lilly and Co
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Eli Lilly and Co
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Publication of CA2670340A1 publication Critical patent/CA2670340A1/en
Application granted granted Critical
Publication of CA2670340C publication Critical patent/CA2670340C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • 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
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • 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
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • 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
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (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)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Reproductive Health (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Gynecology & Obstetrics (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Vascular Medicine (AREA)
  • Immunology (AREA)
  • Anesthesiology (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
CA2670340A 2006-11-20 2007-11-06 Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators Active CA2670340C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US86648406P 2006-11-20 2006-11-20
US60/866,484 2006-11-20
PCT/US2007/083745 WO2008063867A2 (en) 2006-11-20 2007-11-06 Tetrahydrocyclopenta[b] indole compounds as androgen receptor modulators

Publications (2)

Publication Number Publication Date
CA2670340A1 CA2670340A1 (en) 2008-05-29
CA2670340C true CA2670340C (en) 2014-05-20

Family

ID=39415431

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2670340A Active CA2670340C (en) 2006-11-20 2007-11-06 Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators

Country Status (36)

Country Link
US (1) US7968587B2 (OSRAM)
EP (1) EP2094658B1 (OSRAM)
JP (1) JP5399259B2 (OSRAM)
KR (1) KR101121471B1 (OSRAM)
CN (1) CN101541749B (OSRAM)
AR (1) AR063559A1 (OSRAM)
AT (1) ATE538091T1 (OSRAM)
AU (1) AU2007324046B2 (OSRAM)
BR (1) BRPI0719092B8 (OSRAM)
CA (1) CA2670340C (OSRAM)
CL (1) CL2007003182A1 (OSRAM)
CO (1) CO6190513A2 (OSRAM)
CR (1) CR10802A (OSRAM)
CY (1) CY1112284T1 (OSRAM)
DK (1) DK2094658T3 (OSRAM)
EA (1) EA015627B1 (OSRAM)
EC (1) ECSP099350A (OSRAM)
ES (1) ES2376048T3 (OSRAM)
HR (1) HRP20120032T1 (OSRAM)
IL (1) IL198410A (OSRAM)
JO (1) JO2800B1 (OSRAM)
MA (1) MA31072B1 (OSRAM)
MX (1) MX2009005251A (OSRAM)
MY (1) MY154547A (OSRAM)
NO (1) NO342531B1 (OSRAM)
NZ (1) NZ576296A (OSRAM)
PE (1) PE20081161A1 (OSRAM)
PL (1) PL2094658T3 (OSRAM)
PT (1) PT2094658E (OSRAM)
RS (1) RS52191B (OSRAM)
SI (1) SI2094658T1 (OSRAM)
TN (1) TN2009000189A1 (OSRAM)
TW (1) TWI398438B (OSRAM)
UA (1) UA98777C2 (OSRAM)
WO (1) WO2008063867A2 (OSRAM)
ZA (1) ZA200903096B (OSRAM)

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US8268872B2 (en) 2008-02-22 2012-09-18 Radius Health, Inc. Selective androgen receptor modulators
MX2010009162A (es) 2008-02-22 2010-12-21 Radius Health Inc Moduladores selectivos del receptor de androgeno.
BRPI0912394A2 (pt) * 2008-05-16 2016-07-26 Lilly Co Eli moduladores do receptor de androgênio à base de tetra-hidrociclopenta[b]indol
AR078862A1 (es) 2009-11-13 2011-12-07 Lilly Co Eli Ester isopropilico del acido ((s)-7-ciano-4-((2r,3s)-3-hidroxitetrahidrofuran-2-ilmetil)-1,2,3,4-tetrahidro-ciclopenta(b)indol-2-il)carbamico, composiciones farmaceuticas que lo comprenden y su uso en terapia
EP2531029B1 (en) 2010-02-04 2016-10-19 Radius Health, Inc. Selective androgen receptor modulators
WO2011143469A1 (en) 2010-05-12 2011-11-17 Radius Health,Inc Therapeutic regimens
US8642632B2 (en) 2010-07-02 2014-02-04 Radius Health, Inc. Selective androgen receptor modulators
BR112013007685B1 (pt) 2010-09-28 2021-11-09 Radius Pharmaceuticals, Inc Compostos moduladores de receptor andrógeno seletivos, composição farmacêutica compreendendo os referidos compostos, método de identificação de um composto capaz de modular um receptor andrógeno, usos de um composto ou da composição e processo para a preparação de um composto
EP2707373A1 (de) 2011-05-10 2014-03-19 Bayer Intellectual Property GmbH Bicyclische (thio)carbonylamidine
CN103265479B (zh) * 2013-06-14 2017-12-08 南开大学 一种6‑氯甲基烟酸叔丁酯的合成方法
US9421264B2 (en) 2014-03-28 2016-08-23 Duke University Method of treating cancer using selective estrogen receptor modulators
FI3834824T3 (fi) 2014-03-28 2025-12-05 Univ Duke Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla
TWI677489B (zh) 2014-06-20 2019-11-21 美商基利科學股份有限公司 多環型胺甲醯基吡啶酮化合物之合成
JOP20180072A1 (ar) * 2014-09-11 2019-01-30 Lilly Co Eli علاج الأعراض المرتبطة بالعلاج بالحرمان من الأندروجين
JP7221699B2 (ja) 2016-06-22 2023-02-14 エリプセス ファーマ エルティーディー Ａｒ＋乳癌の治療方法
US20180185347A1 (en) 2016-11-16 2018-07-05 Transition Therapeutics (Ireland 2) Limited Tetrahydrocyclopenta[b]indole compounds and phosphodiesterase inhibitors for the treatment of the signs and symptoms of bhp
KR102881465B1 (ko) 2017-01-05 2025-11-04 래디어스 파마슈티컬스, 인코포레이티드 Rad1901-2hcl의 다형 형태
SG11202013177WA (en) 2018-07-04 2021-01-28 Radius Pharmaceuticals Inc Polymorphic forms of rad 1901-2hcl
KR20210127961A (ko) 2019-02-12 2021-10-25 래디어스 파마슈티컬스, 인코포레이티드 방법 및 화합물
US20230096602A1 (en) * 2020-01-27 2023-03-30 Eirgen Pharma Ltd. Tetrahydrocyclopenta[b]indole compounds for treatment of renal disease
US11986461B1 (en) * 2023-08-24 2024-05-21 King Faisal University 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol as an antitumor and antimicrobial compound

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US4988820A (en) * 1986-02-21 1991-01-29 Bayer Aktiengesellschaft Cycloalkano(1,2-B) indole-sulponamides
GB8924392D0 (en) * 1989-10-30 1989-12-20 Bayer Ag Substituted cycloalkano/b/dihydroindole-and-indolesulphonamides
GB9008108D0 (en) * 1990-04-10 1990-06-06 Bayer Ag Cycloalkano(b)dihydroindoles and-indolesulphonamides substituted by heterocycles
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Also Published As

Publication number Publication date
NZ576296A (en) 2011-11-25
MX2009005251A (es) 2009-08-19
BRPI0719092B1 (pt) 2020-08-18
EA200970500A1 (ru) 2009-10-30
PL2094658T3 (pl) 2012-05-31
SI2094658T1 (sl) 2012-04-30
JO2800B1 (en) 2014-03-15
TN2009000189A1 (en) 2010-10-18
EA015627B1 (ru) 2011-10-31
CR10802A (es) 2009-07-13
CN101541749A (zh) 2009-09-23
ES2376048T3 (es) 2012-03-08
MA31072B1 (fr) 2010-01-04
WO2008063867A2 (en) 2008-05-29
IL198410A (en) 2013-09-30
BRPI0719092B8 (pt) 2021-05-25
PT2094658E (pt) 2012-02-22
BRPI0719092A2 (pt) 2013-12-03
HK1134089A1 (en) 2010-04-16
AR063559A1 (es) 2009-02-04
PE20081161A1 (es) 2008-08-15
ECSP099350A (es) 2009-06-30
AU2007324046B2 (en) 2012-04-05
UA98777C2 (en) 2012-06-25
EP2094658B1 (en) 2011-12-21
JP5399259B2 (ja) 2014-01-29
HRP20120032T1 (hr) 2012-02-29
KR101121471B1 (ko) 2012-02-28
CY1112284T1 (el) 2015-12-09
DK2094658T3 (da) 2012-02-13
CA2670340A1 (en) 2008-05-29
MY154547A (en) 2015-06-30
TWI398438B (zh) 2013-06-11
TW200827347A (en) 2008-07-01
RS52191B (sr) 2012-10-31
NO342531B1 (no) 2018-06-11
CO6190513A2 (es) 2010-08-19
CN101541749B (zh) 2013-03-27
ATE538091T1 (de) 2012-01-15
EP2094658A2 (en) 2009-09-02
WO2008063867A3 (en) 2008-07-31
CL2007003182A1 (es) 2008-06-27
IL198410A0 (en) 2010-02-17
US20100069404A1 (en) 2010-03-18
NO20092103L (no) 2009-05-28
KR20090082229A (ko) 2009-07-29
ZA200903096B (en) 2010-07-28
US7968587B2 (en) 2011-06-28
AU2007324046A1 (en) 2008-05-29
JP2010510231A (ja) 2010-04-02

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