EE03241B1 - Androstenooni derivaat 17ß-N-(2,5-bis(trifluorometüül))fenüülkarbamoüül-4-asa-5a-androst-1-een-3-oon ja selle farmatseutiliselt vastuvõetavad solvaadid - Google Patents

Androstenooni derivaat 17ß-N-(2,5-bis(trifluorometüül))fenüülkarbamoüül-4-asa-5a-androst-1-een-3-oon ja selle farmatseutiliselt vastuvõetavad solvaadid

Info

Publication number
EE03241B1
EE03241B1 EE9600130A EE9600130A EE03241B1 EE 03241 B1 EE03241 B1 EE 03241B1 EE 9600130 A EE9600130 A EE 9600130A EE 9600130 A EE9600130 A EE 9600130A EE 03241 B1 EE03241 B1 EE 03241B1
Authority
EE
Estonia
Prior art keywords
androst
phenylcarbamoyl
aza
trifluoromethyl
bis
Prior art date
Application number
EE9600130A
Other languages
English (en)
Estonian (et)
Inventor
William Batchelor Kenneth
Vernon Frye Stephen
Original Assignee
Glaxo Wellcome Inc.
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=22407744&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EE03241(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Glaxo Wellcome Inc. filed Critical Glaxo Wellcome Inc.
Publication of EE03241B1 publication Critical patent/EE03241B1/xx

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J3/00Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26Androgens
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/82Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0066Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by a carbon atom forming part of an amide group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J73/00Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C07J73/001Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
    • C07J73/005Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/14Benz[f]indenes; Hydrogenated benz[f]indenes
EE9600130A 1993-09-17 1994-09-16 Androstenooni derivaat 17ß-N-(2,5-bis(trifluorometüül))fenüülkarbamoüül-4-asa-5a-androst-1-een-3-oon ja selle farmatseutiliselt vastuvõetavad solvaadid EE03241B1 (et)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12328093A 1993-09-17 1993-09-17
PCT/US1994/010530 WO1995007927A1 (en) 1993-09-17 1994-09-16 Androstenone derivative

Publications (1)

Publication Number Publication Date
EE03241B1 true EE03241B1 (et) 1999-12-15

Family

ID=22407744

Family Applications (1)

Application Number Title Priority Date Filing Date
EE9600130A EE03241B1 (et) 1993-09-17 1994-09-16 Androstenooni derivaat 17ß-N-(2,5-bis(trifluorometüül))fenüülkarbamoüül-4-asa-5a-androst-1-een-3-oon ja selle farmatseutiliselt vastuvõetavad solvaadid

Country Status (41)

Country Link
US (2) US5565467A (fi)
EP (1) EP0719278B1 (fi)
JP (1) JP2904310B2 (fi)
KR (1) KR100364953B1 (fi)
CN (1) CN1057771C (fi)
AP (1) AP494A (fi)
AT (1) ATE162199T1 (fi)
AU (1) AU690925B2 (fi)
BG (1) BG62363B1 (fi)
BR (1) BR1100329A (fi)
CA (2) CA2170047C (fi)
CY (2) CY2219B1 (fi)
CZ (1) CZ286069B6 (fi)
DE (2) DE10399022I2 (fi)
DK (1) DK0719278T3 (fi)
EE (1) EE03241B1 (fi)
ES (1) ES2113127T3 (fi)
FI (1) FI115216B (fi)
GR (1) GR3026144T3 (fi)
HK (1) HK1004334A1 (fi)
HR (1) HRP940563B1 (fi)
HU (1) HU220060B (fi)
IL (1) IL110978A (fi)
IS (1) IS1713B (fi)
LU (1) LU91027I2 (fi)
MY (1) MY119778A (fi)
NL (1) NL300122I2 (fi)
NO (2) NO306117B1 (fi)
NZ (1) NZ274642A (fi)
OA (1) OA10575A (fi)
PE (1) PE15095A1 (fi)
PL (1) PL180002B1 (fi)
RO (1) RO117455B1 (fi)
RU (1) RU2140926C1 (fi)
SA (1) SA94150231B1 (fi)
SG (1) SG52650A1 (fi)
SI (1) SI0719278T1 (fi)
SK (1) SK281869B6 (fi)
TW (1) TW369521B (fi)
WO (1) WO1995007927A1 (fi)
ZA (2) ZA947118B (fi)

Families Citing this family (76)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2135167A1 (en) * 1992-05-20 1993-11-25 Donald W. Graham New 17-ester, amide, and ketone derivatives of 3-oxo-4- azasteroids as 5a-reductase inhibitors
WO1994007861A1 (en) * 1992-10-06 1994-04-14 Merck & Co., Inc. 17β-CARBOXANILIDES OF 4-AZA-5α-ANDROSTAN-3-ONES AS 5α-REDUCTASE INHIBITORS
TW408127B (en) * 1993-09-17 2000-10-11 Glaxo Inc Androstenones
US5547957A (en) 1993-10-15 1996-08-20 Merck & Co., Inc. Method of treating androgenic alopecia with 5-α reductase inhibitors
TW382595B (en) * 1993-10-15 2000-02-21 Merck & Co Inc Pharmaceutical composition for use in arresting and reversing androgenic alopecia
ATE175420T1 (de) * 1993-10-21 1999-01-15 Merck & Co Inc 16-substituierte-4-aza-androstan-5-alpha- reduktase-isozym-i-inhibitoren
US5817818A (en) * 1994-09-16 1998-10-06 Glaxo Wellcome Inc. Androstenones
US6001844A (en) * 1995-09-15 1999-12-14 Merck & Co., Inc. 4-Azasteroids for treatment of hyperandrogenic conditions
US5872126A (en) * 1996-09-06 1999-02-16 Merck & Co., Inc. Methods and compositions for treating preterm labor
US5935968A (en) 1997-03-17 1999-08-10 Merck & Co., Inc. Methods for treating polycystic ovary syndrome
GB9717428D0 (en) * 1997-08-19 1997-10-22 Glaxo Group Ltd Pharmaceutical composition
JP2001521000A (ja) * 1997-10-28 2001-11-06 メルク エンド カムパニー インコーポレーテッド 誘発性急性閉尿の予防
EP1321146A3 (en) * 1998-03-11 2004-06-02 Endorecherche Inc. Inhibitors of type 5 and 3 17beta-hydroxysteroid dehydrogenase and methods for their use
BR9908592A (pt) * 1998-03-11 2001-04-24 Endorech Inc Processo para inibir a atividade de 17ß-hidroxiesteróide desidrogenase tipo 5, composição farmacêutica, inibidor de 17ß-hidroxiesteróide desidrogenase tipo 5, processo para inibir 17ß-hidroxiesteróide desidrogenase tipo 3, inibidor de 17ß-hidroxiesteróide desidrogenase tipo 3, processos para tratar, ou reduzir o risco de desenvolver, câncer da próstata, hiperplasia prostática benigna, acne, seborréia, hirsutismo ou alopécia androgênica, sìndrome de ovário policìstico, câncer de mama, endometriose ou leiomioma, para inibir as secreções hormonais testiculares, para tratar puberdade precoce, e, kit
US5998427A (en) * 1998-05-14 1999-12-07 Glaxo Wellcome Inc. Androstenones
WO1999066915A2 (en) * 1998-06-23 1999-12-29 Southern Illinois University At Carbondale Therapeutic applications of estrogenic carboxylic acids
US6410565B1 (en) 1999-02-03 2002-06-25 Eli Lilly And Company α1-adrenergic receptor antagonists
DK1175433T3 (da) 1999-05-04 2005-09-19 Strakan Int Ltd Androgenglycosider og androgen aktivitet deraf
US6645974B2 (en) 2001-07-31 2003-11-11 Merck & Co., Inc. Androgen receptor modulators and methods for use thereof
JP4490689B2 (ja) * 2001-10-03 2010-06-30 メルク・シャープ・エンド・ドーム・コーポレイション アンドロゲン受容体調節剤としてのアンドロスタン17β−カルボキサミド類
EP1468983B1 (en) * 2002-01-25 2007-11-21 Asahi Glass Company Ltd. Process for producing 2,5-bis(trifluoromethyl)nitrobenzene
WO2003090753A1 (en) * 2002-04-24 2003-11-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical combination for the treatment of benign prostatic hyperplasia or for the long-term prevention of acute urinary retention
US20050131005A1 (en) * 2002-04-30 2005-06-16 Jiabing Wang 4-azasteroid derivatives as androgen receptor modulators
US7326717B2 (en) * 2003-05-06 2008-02-05 L'oreal Pyrimidine n-oxide compounds for stimulating the growth of keratin fibers and/or reducing loss thereof
US7022854B2 (en) * 2003-07-17 2006-04-04 Dr. Reddy's Laboratories, Limited Forms of dutasteride and methods for preparation thereof
US20050059692A1 (en) * 2003-09-09 2005-03-17 Dr. Reddy's Laboratories Limited Process for the preparation of 17beta-N-[2,5-bis(trifluoromethyl)phenyl] carbamoyl-4-aza-5-alpha-androst-1-en-3-one
EP1746998A1 (en) * 2004-03-22 2007-01-31 Ranbaxy Laboratories, Ltd. Combination therapy for lower urinary tract symptoms
WO2005097127A2 (en) * 2004-04-02 2005-10-20 Merck & Co., Inc. Method of treating men with metabolic and anthropometric disorders
AU2005280334A1 (en) * 2004-08-25 2006-03-09 Merck Sharp & Dohme Corp. Androgen receptor modulators
US7998970B2 (en) * 2004-12-03 2011-08-16 Proteosys Ag Use of finasteride, dutasteride and related compounds for the prevention or treatment of neurologically-associated disorders
US20060193804A1 (en) * 2005-02-24 2006-08-31 L'oreal Haircare use of cyclic amine derivatives
AU2006229840B2 (en) 2005-03-25 2010-12-23 Merck Sharp & Dohme Corp. Method of treating men with testosterone supplement and 5alpha-reductase inhibitor
WO2007120263A2 (en) * 2005-11-10 2007-10-25 Dr. Reddy's Laboratories Ltd. Preparation of dutasteride
EP1897533A1 (en) * 2006-09-08 2008-03-12 Revotar Biopharmaceuticals AG Use of 1,6-Bis [3-(3-carboxymethylphenyl)-4-(2-alpha -D-mannopyranosyl-oxy)-phenyl] hexane for the preparation of cosmetic compositions
EP1946756A1 (en) * 2007-01-17 2008-07-23 Revotar Biopharmaceuticals AG Use of entacapone in cosmetic, dermatological and pharmaceutical compositions
FR2920309B1 (fr) 2007-08-28 2010-05-28 Galderma Res & Dev Utilisation de travoprost pour traiter la chute des cheveux
US20090076057A1 (en) * 2007-09-13 2009-03-19 Protia, Llc Deuterium-enriched dutasteride
EP2050436A1 (en) 2007-12-21 2009-04-22 Siegfried Generics International AG Pharmaceutical composition containing dutasteride
AR070313A1 (es) 2008-01-03 2010-03-31 Gador Sa Un procedimiento para preparar una forma solida y cristalina de dutasteride, una forma polimorfica del compuesto (forma iii) y una composicion farmaceutica que incluye dicha forma
FR2929118B1 (fr) 2008-03-28 2010-05-07 Oreal Utilisation de l'association de madecassoside et/ou de terminoloside et d'une arginine pour induire et/ou stimuler la croissance de ces fibres keratiniques humaines et/ou freiner leur chute
FR2929117B1 (fr) 2008-03-28 2010-05-07 Oreal Utilisation de l'association du 2,4-diaminopyrimidine 3-n-oxyde et du madecassosside et/ou du terminoloside pour induire et/ou stimuler la croissance de ces fibres keratiniques humaines et/ou freiner leur chute
PT2273994E (pt) 2008-04-03 2016-03-15 Neurmedix Inc Formas de estado sólido de um produto farmacêutico
US20100048598A1 (en) * 2008-08-21 2010-02-25 Sateesh Kandavilli Topical compositions comprising 5-alpha reductase inhibitors
CN101759762B (zh) * 2008-11-06 2013-03-20 天津金耀集团有限公司 4ad在制备度他雄胺中的应用
US8563728B2 (en) * 2009-07-09 2013-10-22 Aurobindo Pharma Ltd. Process for the preparation of Dutasteride
FR2949052B1 (fr) 2009-08-13 2015-03-27 Oreal Procede de traitement cosmetique du cuir chevelu.
EP2468262A1 (en) 2010-12-06 2012-06-27 Krka Tovarna Zdravil, D.D., Novo Mesto Pharmaceutical composition comprising dutasteride
BRPI1103204A2 (pt) * 2011-06-03 2014-02-25 Eurofarma Lab S A Composição farmacêutica para o tratamento de hiperplasia prostática benigna
HU230730B1 (hu) 2011-06-30 2017-12-28 Richter Gedeon Nyrt Eljárás (5alfa,17béta)-N-[2,5-bisz-(trifluormetil)-fenil]-3-oxo-4-aza-5-androszt-1-én-17-karbonsavamid előállítására
CN103059098B (zh) * 2011-10-24 2015-04-01 成都国为医药科技有限公司 一种度他雄胺的制备方法
US9622981B2 (en) 2011-11-17 2017-04-18 Mylan Inc. Liquid-filled hard gel capsule pharmaceutical formulations
CN102382165B (zh) * 2011-12-02 2014-05-07 华润赛科药业有限责任公司 一种度他雄胺的制备方法
CN103554210A (zh) * 2012-01-05 2014-02-05 中国药科大学 甾体类5α-还原酶抑制剂、其制备方法及其医药用途
CN102532236B (zh) * 2012-01-05 2014-04-16 中国药科大学 甾体类5α-还原酶抑制剂、其制备方法及其医药用途
KR101976137B1 (ko) 2012-01-25 2019-05-09 한미약품 주식회사 두타스테라이드 함유 자가 유화 약물전달 시스템용 조성물 및 이의 제조 방법
WO2015065716A1 (en) 2013-10-15 2015-05-07 Case Western Reserve University Compositions and methods of modulating short-chain dehydrogenase activity
PT2838533T (pt) 2012-04-16 2017-11-22 Univ Texas Composições e métodos de modulação da atividade de 15-pgdh
WO2014002015A1 (en) 2012-06-25 2014-01-03 Ranbaxy Laboratories Limited Pharmaceutical composition comprising dutasteride
WO2014158875A1 (en) * 2013-03-14 2014-10-02 Pellficure Pharmaceuticals Inc. Novel therapy for prostate carcinoma
CN103254268A (zh) * 2013-05-16 2013-08-21 寿光市富康化学工业有限公司 一种制备度他雄胺的工艺
BR102013020508B1 (pt) 2013-08-12 2021-01-12 Ems S/A. Forma de dosagem que compreende um inibidor de esteroide 5-alfa-redutase e um bloqueador alfa, processo para a preparaçãode uma forma de dosagem e uso da forma de dosagem
EP2949319A1 (en) 2014-05-26 2015-12-02 Galenicum Health S.L. Pharmaceutical compositions comprising an active agent
KR101590072B1 (ko) 2014-12-23 2016-01-29 한미약품 주식회사 두타스테라이드를 포함하는 자가유화 약물전달 시스템용 조성물
EP3268129A2 (en) * 2015-03-13 2018-01-17 Dow Global Technologies LLC Olefin oligomerisation process with a catalyst comprising a chromium complex with a phosphacycle-containing ligand
KR102503428B1 (ko) 2015-12-22 2023-02-24 한미약품 주식회사 두타스테라이드를 포함하는 경구용 연질 캡슐 제형용 포장재
AU2017233134A1 (en) 2016-03-16 2018-10-04 Hanmi Pharm. Co., Ltd. Dutasteride- and tamsulosin-containing hard capsule complex and preparation method therefor
KR101716878B1 (ko) 2016-05-12 2017-03-15 주식회사 유유제약 글리세롤 지방산에스테르유도체 또는 프로필렌글리콜 지방산에스테르유도체를 함유한 두타스테리드와 타다라필의 복합 캡슐제제 조성물 및 이의 제조방법
US11690847B2 (en) 2016-11-30 2023-07-04 Case Western Reserve University Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof
JP2020514323A (ja) 2017-02-06 2020-05-21 ケース ウエスタン リザーブ ユニバーシティ 短鎖デヒドロゲナーゼ活性を調節する組成物と方法
BR112020004197A2 (pt) 2017-09-01 2020-09-08 Jw Pharmaceutical Corporation preparação sólida compreendendo dutasterida e método para preparar a mesma
KR101996597B1 (ko) 2017-10-13 2019-07-31 주식회사 유유제약 두타스테리드와 타다라필을 용해시킨 경구용 캡슐 제형의 복합제제
KR102281252B1 (ko) 2018-05-21 2021-07-23 (주)인벤티지랩 두타스테라이드를 포함하는 마이크로 입자 및 이의 제조 방법
WO2019225924A1 (ko) * 2018-05-21 2019-11-28 (주)인벤티지랩 두타스테라이드를 포함하는 마이크로 입자 및 이의 제조 방법
EA202191422A1 (ru) 2018-11-21 2021-10-21 Кейс Вестерн Ризерв Юниверсити Композиции и способы модулирования активности короткоцепочечной дегидрогеназы
KR20200074759A (ko) 2018-12-17 2020-06-25 동국제약 주식회사 두타스테라이드를 함유하는 고형제제
PE20230777A1 (es) 2020-05-20 2023-05-09 Rodeo Therapeutics Corp Composiciones y metodos para modular la actividad de deshidrogenasas de cadena corta

Family Cites Families (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377584A (en) * 1978-04-13 1983-03-22 Merck & Co., Inc. 4-Aza-17β-substituted-5α-androstan-3-one-reductase inhibitors
AU527030B2 (en) * 1978-04-13 1983-02-10 Merck & Co., Inc. 4-aza-17-substituted-5a-androstan-3-ones
US4191759A (en) * 1978-04-13 1980-03-04 Merck & Co., Inc. N-substituted-17β-carbamoylandrost-4-en-3-one 5α reductase inhibitors
US4220775A (en) * 1979-03-15 1980-09-02 Merck & Co., Inc. Preparation of 4-aza-17-substituted-5α-androstan-3-ones useful as 5α-reductase inhibitors
US4317817A (en) * 1979-08-27 1982-03-02 Richardson-Merrell Inc. Novel steroid 5α-reductase inhibitors
DK465481A (da) * 1980-11-21 1982-05-22 Hoffmann La Roche Fremgangsmaade til fremstilling af d-homostemoider
ATE67503T1 (de) * 1984-02-27 1991-10-15 Merck & Co Inc 17-beta-substituierte-4-aza-5-alpha-androstenon und ihre anwendung als 5-alpha-reduktaseinhibitoren.
US5049562A (en) * 1984-02-27 1991-09-17 Merck & Co., Inc. 17β-acyl-4-aza-5α-androst-1-ene-3-ones as 5α-reductase inhibitors
US4760071A (en) * 1984-02-27 1988-07-26 Merck & Co., Inc. 17β-N-monosubstituted carbamoyl-4-aza-5α-androst-1-en-3-ones which are active as testosterone 5α-reductase inhibitors
NZ211145A (en) * 1984-02-27 1988-10-28 Merck & Co Inc 4-aza-5-alpha-androst-1-en-3-ones and pharmaceutical compositions
GB8505862D0 (en) * 1985-03-07 1985-04-11 Erba Farmitalia Steroidic 5alpha-reductase inhibitors
EP0271219B1 (en) * 1986-11-20 1992-07-29 Merck & Co. Inc. Topical pharmaceutical composition containing 17-beta-methoxycarbonyl-4-methyl-4-aza-5-alpha-androst-1-en-3-one
US4845104A (en) * 1986-11-20 1989-07-04 Merck & Co., Inc. Oxidized analogs of 17β-N-monosubstituted-carbamoyl-4-aza-5-α-androstan-3-ones
US4888336A (en) * 1987-01-28 1989-12-19 Smithkline Beckman Corporation Steroid 5-alpha-reductase inhibitors
US5110939A (en) * 1987-01-28 1992-05-05 Smithkline Beecham Corporation Intermediates in the preparation of steriod 5-alpha-reductase inhibitors
US4814324A (en) * 1987-03-06 1989-03-21 Merck & Co., Inc. Sterol inhibitors of testosterone 5α-reductase
DE3888378T2 (de) * 1987-04-03 1994-09-29 Merck & Co Inc Behandlung von Prostatacarcinoma mit 17-beta-n-monosubstituierten-Carbamoyl-4-aza-5-alpha-Androst-1-en-3-onen.
DE3888994T2 (de) * 1987-04-03 1994-11-03 Merck & Co Inc Behandlung von androgener Alopecia mit 17-beta-n-mono-substituierten-carbamoyl-4-aza-5-alpha-androst-1-en-3-onen.
US4910226A (en) * 1987-04-29 1990-03-20 Smithkline Beckman Corporation Steroid 5-alpha-reductase inhibitors
US5041433A (en) * 1987-04-29 1991-08-20 Smithkline Beecham Corporation 11-keto or hydroxy 3,5-diene steroids as inhibitors of steriod 5-α-reductase
ZA883034B (en) * 1987-04-29 1989-03-29 Smithkline Beckman Corp Steroid 5-alpha-reductase inhibitors
NZ225100A (en) * 1987-06-29 1991-09-25 Merck & Co Inc Reaction of steroids (including 4-azasteroids) with a silylating agent in the presence of a quinone to introduce a delta' double bond and silylated intermediates
CA1331457C (en) * 1988-05-25 1994-08-16 Dennis Alan Holt Aromatic steroid 5-–-reductase inhibitors
US4954446A (en) * 1988-05-25 1990-09-04 Smithkline Beecham Corporation Aromatic steroid 5-α-reductase inhibitors
US5237061A (en) * 1988-10-31 1993-08-17 Merck & Co., Inc. Methods of synthesizing benign prostatic hypertropic agents and their intermediates
US4946834A (en) * 1988-12-23 1990-08-07 Smithkline Beecham Corporation Phosphonic acid substituted steroids as steroid 5α-reductase inhibitors
US4970205A (en) * 1988-12-23 1990-11-13 Smithkline Beecham Corporation Sulfonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase
US5026882A (en) * 1988-12-23 1991-06-25 Smithkline Beecham Corporation Phosphinic acid substituted steroids as inhibitors of steroid 5α-reductase
US4882319A (en) * 1988-12-23 1989-11-21 Smithkline Beckman Corporation Phosphonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase
US4937237A (en) * 1988-12-23 1990-06-26 Smithkline Beckman Corporation Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase
US4966897A (en) * 1989-08-15 1990-10-30 Merrell Dow Pharmaceuticals Inc. 4-substituted 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors
US4966898A (en) * 1989-08-15 1990-10-30 Merrell Dow Pharmaceuticals Inc. 4-substituted 17β-(cyclopropylamino)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors
CA2023157A1 (en) * 1989-08-21 1991-02-22 Gary H. Rasmusson 17 beta-acyl-4-aza-5 alpha-androst-1-ene-3-ones as 5 alpha-reductase inhibitors
US5032586A (en) * 1989-08-24 1991-07-16 Smithkline Beecham Corporation 7-keto or hydroxy 3,5-diene steroids as inhibitors of steroid 5-alpha reductase
US5021575A (en) * 1989-11-13 1991-06-04 Merck & Co., Inc. Method for introducing a 1,2 double bond into azasteroids
US5100917A (en) * 1989-12-29 1992-03-31 Merrell Dow Pharmaceuticals Inc. Novel a-nor-steroid-3-carboxylic acid derivatives
GB9002922D0 (en) * 1990-02-09 1990-04-04 Erba Carlo Spa 17 beta-substituted-4-aza-5 alpha-androstan-3-one derivatives and process for their preparation
US5098908A (en) * 1990-06-20 1992-03-24 Merck & Co., Inc. 17β-hydroxybenzoyl-4-aza-5α-androst-1-en-3-ones as testosterone reductase inhibitors
EP0462662A3 (en) * 1990-06-20 1992-08-19 Merck & Co. Inc. 17beta-n-monosubstituted adamantyl/norbornanyl carbamoyl-4-aza-5alpha-androst-1-en-3-ones and androstan-3-ones
US5061802A (en) * 1990-06-20 1991-10-29 Merck & Co. Inc. 17β-aminobenzoyl-4-aza-5α-androst-1-en-3-ones as benign prostatic hypertrophy agents
EP0462664A3 (en) * 1990-06-20 1992-11-25 Merck & Co. Inc. Specific 17beta-thiobenzoyl-4-aza-5alpha-androst-1-en-3-ones as antiandrogenic agents
EP0462665A3 (en) * 1990-06-20 1993-06-30 Merck & Co. Inc. Selected 17beta-polyaroyl-4-aza-5alpha-androst-1-en-3-ones as steroidal reductase inhibitors
US5318961A (en) * 1990-08-01 1994-06-07 Merrell Dow Pharmaceuticals Inc. 4-amino-Δ4-steroids and their use as 5α-reductase inhibitors
NZ239141A (en) * 1990-08-01 1994-04-27 Merrell Dow Pharma 4-amino-delta-4,6-steroids; preparatory processes and pharmaceutical compositions
AU637247B2 (en) * 1990-08-01 1993-05-20 Merrell Dow Pharmaceuticals Inc. 4-amino-delta4-steroids and their use as 5alpha-reductase inhibitors
US5091534A (en) * 1990-08-27 1992-02-25 Merck & Co., Inc. Trialkylsilyl trifluoromethanesulfonate mediated α-methylenic carbon functionalization of 4-AZA-5α-androstan-3-one steroids
US5120847A (en) * 1990-08-27 1992-06-09 Merck & Co., Inc. Process for iodinating or brominating the α-methylenic carbon of a secondary amide
US5061801A (en) * 1990-09-24 1991-10-29 Merck & Co., Inc. Intermediate for making 3-oxo-4-aza-androst-1-ene 17β-ketones
US5061803A (en) * 1990-09-24 1991-10-29 Merck & Co., Inc. Process for making 17-beta alkanoyl 3-oxo-4-aza-5-α-androst-1-enes
CA2050824A1 (en) * 1990-09-24 1992-03-25 John M. Williams Process for making 3-oxo-4-aza-androst-1-ene 17-.beta.-ketones
IE76452B1 (en) * 1990-10-29 1997-10-22 Sankyo Co Azasteroid compounds for the treatment of prostatic hypertrophy their preparation and use
IL101245A0 (en) * 1991-03-20 1992-11-15 Merck & Co Inc Pharmaceutical compositions for the treatment of prostatic cancer
IL101243A (en) * 1991-03-20 1999-12-22 Merck & Co Inc Pharmaceutical preparations for the treatment of benign prostatic hyperplasia containing steroid history
AU1893492A (en) * 1991-04-17 1992-11-17 Merck & Co., Inc. Pharmaceutical combination for the treatment of benign prostatic hyperplasia comtaining a 5 alpha-reductase inhibitor
GB9115676D0 (en) * 1991-07-19 1991-09-04 Erba Carlo Spa Process for the preparation of 17 beta substituted-4-aza-5 alpha-androstan-3-one derivatives
US5304562A (en) * 1991-10-09 1994-04-19 Ciba-Geigy Corporation 17β-substituted Aza-androstane derivatives
CA2126203A1 (en) * 1991-12-20 1993-07-08 Stephen V. Frye Inhibitors of 5-alpha-testosterone reductase
JP3164389B2 (ja) * 1991-12-25 2001-05-08 三共株式会社 4−アザステロイド類
AU676478B2 (en) * 1992-05-20 1997-03-13 Merck & Co., Inc. New delta-17 and delta-20 olefinic and saturated 17beta- substituted-4-aza-5alpha-androstan-3-ones as 5alpha- reductase inhibitors
AU675225B2 (en) * 1992-05-20 1997-01-30 Merck & Co., Inc. 17-amino substituted 4-azasteroid 5alpha-reductase inhibitors
US5536727A (en) * 1992-05-20 1996-07-16 Merck & Co., Inc. 17-Ethers and thioethers of 4-aza-steroids
US5620986A (en) * 1992-05-20 1997-04-15 Merck & Co., Inc. 17 urea, thiourea, thiocarbamyl and carbamyl4-azasteroid 5-reductase inhibitors useful in the prevention and treatment of hyperandrogenic disorders
US5710275A (en) * 1992-05-20 1998-01-20 Merck & Co., Inc. 7β-substituted-4-aza-5α-androstan-3-ones as 5α-reductase inhibitors
WO1993023419A1 (en) * 1992-05-20 1993-11-25 Merck & Co., Inc. NEW 7β-SUBSTITUTED-4-AZA-5α-CHOLESTAN-ONES AS 5α-REDUCTASE INHIBITORS
CA2135167A1 (en) * 1992-05-20 1993-11-25 Donald W. Graham New 17-ester, amide, and ketone derivatives of 3-oxo-4- azasteroids as 5a-reductase inhibitors
CA2135173A1 (en) * 1992-05-20 1993-11-25 Bruce E. Witzel Ester derivatives of 4-aza-steroids
WO1993023039A1 (en) * 1992-05-20 1993-11-25 Merck & Co., Inc. Substituted 4-aza-5a-androstan-ones as 5a-reductase inhibitors
UA35589C2 (uk) * 1992-05-21 2001-04-16 Андорешерш Інк. ІНГІБІТОРИ ТЕСТОСТЕРОН 5-<font face="Symbol">a</font>-РЕДУКТАЗИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ІНГІБУВАННЯ АКТИВНОСТІ ТЕСТОСТЕРОН 5-<font face="Symbol">a</font>-РЕДУКТАЗИ
GB9210880D0 (en) * 1992-05-21 1992-07-08 Smithkline Beecham Corp Compounds
GB9216284D0 (en) * 1992-07-31 1992-09-16 Erba Carlo Spa Fluorinated 17beta-substituted 4-aza-5alpha-androstane-3-one derivatives
GB9216329D0 (en) * 1992-07-31 1992-09-16 Erba Carlo Spa 17beta-substituted 4-aza-5alpha-androstan-3-one derivatives
HU212459B (en) * 1992-10-02 1996-06-28 Richter Gedeon Vegyeszet Process for producing new 17-beta-substituted 4-aza-androstane-derivatives and pharmaceutical compositions containing them
US5278159A (en) * 1992-10-06 1994-01-11 Merck & Co., Inc. Aryl ester derivatives of 3-oxo-4-aza-androstane 17-β-carboxylates as 5-α-reductase inhibitors
WO1994007861A1 (en) * 1992-10-06 1994-04-14 Merck & Co., Inc. 17β-CARBOXANILIDES OF 4-AZA-5α-ANDROSTAN-3-ONES AS 5α-REDUCTASE INHIBITORS
AP9300589A0 (en) * 1992-11-18 1994-01-31 Smithkline Beecham Corp Novel 17a and 17b substituted acyl-3-carboxy 3,5-diene steroidal compounds, pharmaceutical compositions containing these compounds, and methods for using these compounds to inhibit steroid 5-a-reductase.
AP459A (en) * 1992-12-18 1996-02-14 Glaxo Wellcome Inc Substituted 6-azaandrostenones.
US5380728A (en) * 1993-02-10 1995-01-10 Merck & Co., Inc. Aldehyde metabolite of 17β-N-monosubstituted-carbamoyl-4-aza-5α-a
US5438061A (en) * 1993-07-16 1995-08-01 Merck & Co., Inc. 7-substituted-δ4-6-azasteroid derivatives as 5α-reductase inhibitors
TW408127B (en) * 1993-09-17 2000-10-11 Glaxo Inc Androstenones

Also Published As

Publication number Publication date
ZA947119B (en) 1995-05-26
CA2462061A1 (en) 1995-03-23
JPH09502731A (ja) 1997-03-18
ES2113127T3 (es) 1998-04-16
BG100410A (bg) 1996-09-30
PL180002B1 (pl) 2000-11-30
DK0719278T3 (da) 1998-09-14
AP494A (en) 1996-05-15
IL110978A0 (en) 1994-11-28
CY2004002I1 (el) 2009-11-04
HRP940563B1 (en) 2000-10-31
US5565467A (en) 1996-10-15
HU9600656D0 (en) 1996-05-28
BG62363B1 (bg) 1999-09-30
CY2219B1 (en) 2003-04-18
WO1995007927A1 (en) 1995-03-23
AP9400669A0 (en) 1994-10-31
LU91027I2 (fr) 2004-04-28
DE69407978T2 (de) 1998-05-07
NO961080L (no) 1996-03-15
NO961080D0 (no) 1996-03-15
IS1713B (is) 1998-12-30
HRP940563A2 (en) 1997-02-28
JP2904310B2 (ja) 1999-06-14
NL300122I1 (nl) 2003-06-02
SK281869B6 (sk) 2001-08-06
CY2004002I2 (el) 2009-11-04
EP0719278B1 (en) 1998-01-14
AU690925B2 (en) 1998-05-07
SK34796A3 (en) 1996-07-03
KR100364953B1 (ko) 2003-04-08
NO2003003I2 (no) 2007-06-11
US5846976A (en) 1998-12-08
CZ74596A3 (en) 1996-09-11
NO306117B1 (no) 1999-09-20
HU220060B (hu) 2001-10-28
ZA947118B (en) 1995-05-26
CA2170047C (en) 2004-11-09
RO117455B1 (ro) 2002-03-29
NZ274642A (en) 1997-11-24
RU2140926C1 (ru) 1999-11-10
HK1004334A1 (en) 1998-11-20
ATE162199T1 (de) 1998-01-15
FI961231A0 (fi) 1996-03-15
FI961231A (fi) 1996-03-15
CN1131424A (zh) 1996-09-18
GR3026144T3 (en) 1998-05-29
DE69407978D1 (de) 1998-02-19
MY119778A (en) 2005-07-29
DE10399022I1 (de) 2004-01-15
CA2170047A1 (en) 1995-03-23
CN1057771C (zh) 2000-10-25
OA10575A (en) 2002-06-25
EP0719278A1 (en) 1996-07-03
DE10399022I2 (de) 2012-09-13
IS4205A (is) 1995-03-18
IL110978A (en) 1999-01-26
SI0719278T1 (en) 1998-06-30
PE15095A1 (es) 1995-06-04
AU7875194A (en) 1995-04-03
HUT73850A (en) 1996-09-30
BR1100329A (pt) 2000-06-13
SG52650A1 (en) 1998-09-28
NL300122I2 (nl) 2003-09-01
SA94150231B1 (ar) 2005-05-04
TW369521B (en) 1999-09-11
CZ286069B6 (cs) 2000-01-12
PL313492A1 (en) 1996-07-08
FI115216B (fi) 2005-03-31

Similar Documents

Publication Publication Date Title
EE03241B1 (et) Androstenooni derivaat 17ß-N-(2,5-bis(trifluorometüül))fenüülkarbamoüül-4-asa-5a-androst-1-een-3-oon ja selle farmatseutiliselt vastuvõetavad solvaadid
FI944310A0 (fi) Heteroaryyliamino- ja heteroaryylisuolfonamidosubstituoituja 3-bentsyyliaminometyylipiperidiinejä ja vastaavia yhdisteitä
ITMI940144A0 (it) Soluzioni e loro preparazione
FI944624A (fi) 4-aryyliaminobentsopyraani- ja niiden kaltaisia yhdisteitä
ZA976222B (en) N-(4-aryl-thiazol-2-yl)-sulphonamide derivatives and their use.
DK0853617T3 (da) 2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalinylderivater
AU6636598A (en) Novel 3,4-dialkoxyphenyl derivatives and the use thereof
DE69431965D1 (de) Wirkstoff gegen fettsucht
DE4495960D2 (de) Phoropter
AU7978794A (en) 3,17-dihydroxy-3,7,16 and/or 17-methyl-androst-5-ene compounds, derivatives thereof, and their use
NO954767D0 (no) 4-amino-17 delser som C17-20-lyase- og 5
PT811593E (pt) Agentes insecticidas e acaricidas 1,4-diaril-2-fluor-2-buteno
DE9303053U1 (de) Schaftfräser
HU9502863D0 (en) 7-azabicyclo-[2.2.1]-heptane and -heptene derivatives as analgesics and anti-inflammatory agents
FI934624A0 (fi) Enantiomera cis-3-(4,6-dihydroxikroman-3-ylmetyl)bensoesyror
EP0630059A3 (en) Superconductive device having a Peltier element preventing dew from integrating therein.
ITMI962503A0 (it) Procedimento per progettare una apparecchiatura impiegante superconduttivita&#39; e apparecchiatura impiegante superconduttivita&#39;
AU7075694A (en) Novel cross-linking agents and use thereof
AU6871696A (en) N-(1-isopropyl-2-methyl-1-propenyl)heteroaryloxyacetamides and the use thereof as herbicides
ITMI920870A1 (it) Poliestereimmide trmotropica, procedimento per la sua preparazione e suo impiego
NO306672B1 (no) N,N-dietyl-8,8-dipropyl-2-azaspiro[4,5]decan-2-propanamindimaleat, farmasöytisk blanding omfattende forbindelsen samt anvendelse derav
DE9320527U1 (de) Einstellbarer Monitor
DE9319697U1 (de) Monitor
NO944024L (no) 1,2-dihydro-2-okso-pyridin
KR950007960U (ko) 회전의자

Legal Events

Date Code Title Description
KB4A Valid patent at the end of a year

Effective date: 20021231

KB4A Valid patent at the end of a year

Effective date: 20031231

KB4A Valid patent at the end of a year

Effective date: 20041231

GB1A Change in the ownership or in the address of the owner
KB4A Valid patent at the end of a year

Effective date: 20051231

KB4A Valid patent at the end of a year

Effective date: 20061231

KB4A Valid patent at the end of a year

Effective date: 20071231

KB4A Valid patent at the end of a year

Effective date: 20081231

KB4A Valid patent at the end of a year

Effective date: 20091231

KB4A Valid patent at the end of a year

Effective date: 20101231