AP494A - Androstenone derivative. - Google Patents

Androstenone derivative. Download PDF

Info

Publication number: AP494A
Authority: AP; ARIPO
Prior art keywords: compound; formula; testosterone; mediated disease; pharmaceutically acceptable
Prior art date: 1993-09-17

Application number

APAP/P/1994/000669A

Other languages

English (en)

Other versions

AP9400669A0 (en

Inventor

Kenneth William Batchelor

Stephen Vernon Fyre

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.)

1993-09-17

Filing date

1994-09-15

Publication date

1996-05-15

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=AP494(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-09-15 Application filed by Glaxo Wellcome Inc filed Critical Glaxo Wellcome Inc

1994-10-31 Publication of AP9400669A0 publication Critical patent/AP9400669A0/xx

1996-05-15 Application granted granted Critical

1996-05-15 Publication of AP494A publication Critical patent/AP494A/en

Links

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125000003710 aryl alkyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
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230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
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229940125846 compound 25 Drugs 0.000 description 1
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239000007891 compressed tablet Substances 0.000 description 1
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OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
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MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
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238000002347 injection Methods 0.000 description 1
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229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
JBGNFLUETJDDBA-UHFFFAOYSA-N n,n-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)N(C(F)(F)F)C1=CC=CC=C1 JBGNFLUETJDDBA-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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239000012286 potassium permanganate Substances 0.000 description 1
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201000007094 prostatitis Diseases 0.000 description 1
238000011552 rat model Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
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229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
WSRBRQQGWDWSON-UHFFFAOYSA-M sodium;3,7-dimethylpurine-2,6-dione;2-hydroxybenzoate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O.CN1C(=O)NC(=O)C2=C1N=CN2C WSRBRQQGWDWSON-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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150000005846 sugar alcohols Polymers 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
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VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic 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
- C07C235/82—Carboxylic 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0066—Normal 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids 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
- C07J73/005—Steroids 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- 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
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

APAP/P/1994/000669A 1993-09-17 1994-09-15 Androstenone derivative. AP494A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US12328093A	1993-09-17	1993-09-17

Publications (2)

Publication Number	Publication Date
AP9400669A0 AP9400669A0 (en)	1994-10-31
AP494A true AP494A (en)	1996-05-15

Family

ID=22407744

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1994/000669A AP494A (en)	1993-09-17	1994-09-15	Androstenone derivative.

Country Status (41)

Country	Link
US (2)	US5565467A (es)
EP (1)	EP0719278B1 (es)
JP (1)	JP2904310B2 (es)
KR (1)	KR100364953B1 (es)
CN (1)	CN1057771C (es)
AP (1)	AP494A (es)
AT (1)	ATE162199T1 (es)
AU (1)	AU690925B2 (es)
BG (1)	BG62363B1 (es)
BR (1)	BR1100329A (es)
CA (2)	CA2170047C (es)
CY (2)	CY2219B1 (es)
CZ (1)	CZ286069B6 (es)
DE (2)	DE10399022I2 (es)
DK (1)	DK0719278T3 (es)
EE (1)	EE03241B1 (es)
ES (1)	ES2113127T3 (es)
FI (1)	FI115216B (es)
GR (1)	GR3026144T3 (es)
HK (1)	HK1004334A1 (es)
HR (1)	HRP940563B1 (es)
HU (1)	HU220060B (es)
IL (1)	IL110978A (es)
IS (1)	IS1713B (es)
LU (1)	LU91027I2 (es)
MY (1)	MY119778A (es)
NL (1)	NL300122I2 (es)
NO (2)	NO306117B1 (es)
NZ (1)	NZ274642A (es)
OA (1)	OA10575A (es)
PE (1)	PE15095A1 (es)
PL (1)	PL180002B1 (es)
RO (1)	RO117455B1 (es)
RU (1)	RU2140926C1 (es)
SA (1)	SA94150231B1 (es)
SG (1)	SG52650A1 (es)
SI (1)	SI0719278T1 (es)
SK (1)	SK281869B6 (es)
TW (1)	TW369521B (es)
WO (1)	WO1995007927A1 (es)
ZA (2)	ZA947119B (es)

Families Citing this family (78)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07508033A (ja) *	1992-05-20	1995-09-07	メルク　エンド　カンパニー　インコーポレーテッド	５α−レダクターゼ阻害剤としての３−オキソ−４−アザステロイドの新規１７−エステル，アミド及びケトン誘導体
DE69329933T2 (de) *	1992-10-06	2001-07-19	Merck & Co., Inc.	17-beta-carboxanilid derivate von 4-aza-5-alpha-androstan-3-one als 5-alpha-reduktase-hemmende arzneimittel
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
DE69415824T2 (de) *	1993-10-21	1999-08-05	Merck & Co., Inc., Rahway, N.J.	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
EP1032400A4 (en) *	1997-10-28	2006-04-12	Merck & Co Inc	PREVENTION OF SUDDEN ACUTE URINRETENTION
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
EP1321146A3 (en) *	1998-03-11	2004-06-02	Endorecherche Inc.	Inhibitors of type 5 and 3 17beta-hydroxysteroid dehydrogenase and methods for their use
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
AU2512800A (en) *	1999-02-03	2000-08-25	Eli Lilly And Company	Alpha1-adrenergic receptor antagonists
BR0010708A (pt)	1999-05-04	2002-02-19	Strakan Ltd	Glicosìdeos androgênicos e atividade androgênica dos mesmos
US6645974B2 (en)	2001-07-31	2003-11-11	Merck & Co., Inc.	Androgen receptor modulators and methods for use thereof
WO2003029268A1 (en) *	2001-10-03	2003-04-10	Merck & Co., Inc.	Androstane 17-beta-carboxamides as androgen receptor modulators
ES2297123T3 (es) *	2002-01-25	2008-05-01	Asahi Glass Company Ltd.	Procedimiento para producir 2,5-bis(trifluorometil)nitribenceno.
JP2005524693A (ja) *	2002-04-24	2005-08-18	ベーリンガーインゲルハイムファルマゲゼルシャフトミットベシュレンクテルハフツングウントコンパニーコマンディトゲゼルシャフト	良性前立腺増殖症の治療又は急性尿閉の長期予防用の医薬組成物
AU2003223754B2 (en) *	2002-04-30	2007-08-16	Merck Sharp & Dohme Corp.	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
EP1734963A4 (en)	2004-04-02	2008-06-18	Merck & Co Inc	METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER
CN101005841A (zh) *	2004-08-25	2007-07-25	默克公司	雄激素受体调节剂
EP1824495A2 (en) *	2004-12-03	2007-08-29	ProteoSys AG	Finasteride, dutasteride and related compounds for preventing/treating 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
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
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
CN102215845A (zh)	2008-04-03	2011-10-12	哈博生物科学公司	药学试剂的固体形式
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
WO2011004242A2 (en) *	2009-07-09	2011-01-13	Aurobindo Pharma Limited	An improved 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
WO2012162776A1 (pt) *	2011-06-03	2012-12-06	Eurofarma Laboratórios 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
CA2870666A1 (en)	2012-04-16	2013-10-24	Case Western Reserve University	Compositions and methods of modulating 15-pgdh activity
WO2014002015A1 (en)	2012-06-25	2014-01-03	Ranbaxy Laboratories Limited	Pharmaceutical composition comprising dutasteride
HK1220356A1 (zh) *	2013-03-14	2017-05-05	Pellficure Pharmaceuticals, Inc.	用於前列腺癌的新颖疗法
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
JP6517197B2 (ja)	2013-10-15	2019-05-22	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および方法
ES2555485T1 (es)	2014-05-26	2016-01-04	Galenicum Health S.L.	Composiciones farmacéuticas que contienen un agente activo
US11351155B2 (en)	2014-12-05	2022-06-07	Case Western Reserve University	Compositions and methods of modulating s-nitrosylation
KR101590072B1 (ko)	2014-12-23	2016-01-29	한미약품 주식회사	두타스테라이드를 포함하는 자가유화 약물전달 시스템용 조성물
BR112017019446A2 (pt) *	2015-03-13	2018-04-24	Dow Global Technologies Llc	complexo de cromo com um ligante contendo fosfaciclo e catalisador de oligomerizacão de olefina do mesmo
KR102503428B1 (ko)	2015-12-22	2023-02-24	한미약품 주식회사	두타스테라이드를 포함하는 경구용 연질 캡슐 제형용 포장재
KR101968754B1 (ko)	2016-03-16	2019-04-12	한미약품 주식회사	두타스테라이드 및 탐수로신 함유 경질 캡슐 복합제 및 그 제조방법
KR101716878B1 (ko)	2016-05-12	2017-03-15	주식회사 유유제약	글리세롤 지방산에스테르유도체 또는 프로필렌글리콜 지방산에스테르유도체를 함유한 두타스테리드와 타다라필의 복합 캡슐제제 조성물 및 이의 제조방법
EP3548035A4 (en)	2016-11-30	2020-07-22	Case Western Reserve University	COMBINATIONS OF 15-PGDH INHIBITORS WITH CORCOSTEROIDS AND / OR TNF INHIBITORS AND THEIR USES
NZ755890A (en)	2017-02-06	2025-12-19	Univ Case Western Reserve	Compositions and methods of modulating short-chain dehydrogenase activity
EP3677253A4 (en)	2017-09-01	2020-11-04	JW Pharmaceutical Corporation	SOLID PREPARATION INCLUDING DUTASTERIDE AND RELATED PREPARATION PROCESS
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
AU2019384821B2 (en)	2018-11-21	2025-09-18	Board Of Regents Of The University Of Texas System	Compositions and methods of modulating short-chain dehydrogenase activity
KR20200074759A (ko)	2018-12-17	2020-06-25	동국제약 주식회사	두타스테라이드를 함유하는 고형제제
JP2023527279A (ja)	2020-05-20	2023-06-28	ロデオ・セラピューティクス・コーポレイション	短鎖デヒドロゲナーゼ活性を調節する組成物及び方法
WO2024144084A1 (ko) *	2022-12-26	2024-07-04	주식회사 유영제약	주 1회 투여를 위한 정제 형태의 고함량 두타스테리드 약제학적 조성물 및 이의 제조방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0484094A2 (en) *	1990-10-29	1992-05-06	Sankyo Company Limited	Azasteroid compounds for the treatment of prostatic hypertrophy, their preparation and use

Family Cites Families (78)

* 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
US4191759A (en) *	1978-04-13	1980-03-04	Merck & Co., Inc.	N-substituted-17β-carbamoylandrost-4-en-3-one 5α reductase inhibitors
AU527030B2 (en) *	1978-04-13	1983-02-10	Merck & Co., Inc.	4-aza-17-substituted-5a-androstan-3-ones
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
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
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.
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
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
ATE78827T1 (de) *	1986-11-20	1992-08-15	Merck & Co Inc	Topisches arzneimittel enthaltend 17-beta-methoxy-carbonyl-4-methyl-4-aza-5-alpha androst-1-en-3- one.
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.
EP0285382B1 (en) *	1987-04-03	1994-04-13	Merck & Co. Inc.	Treatment of androgenic alopecia with 17beta-n-monosubstituted-carbamoyl-4-aza-5alpha-androst-1-en-3-ones
ZA883034B (en) *	1987-04-29	1989-03-29	Smithkline Beckman Corp	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
US4910226A (en) *	1987-04-29	1990-03-20	Smithkline Beckman Corporation	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
JP2675418B2 (ja) *	1988-05-25	1997-11-12	スミスクライン・ベックマン・コーポレイション	芳香族ステロイド５‐α‐レダクターゼ抑制剤
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
US4937237A (en) *	1988-12-23	1990-06-26	Smithkline Beckman Corporation	Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase
US4882319A (en) *	1988-12-23	1989-11-21	Smithkline Beckman Corporation	Phosphonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase
US4970205A (en) *	1988-12-23	1990-11-13	Smithkline Beecham Corporation	Sulfonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase
US4946834A (en) *	1988-12-23	1990-08-07	Smithkline Beecham Corporation	Phosphonic acid substituted steroids as steroid 5α-reductase inhibitors
US5026882A (en) *	1988-12-23	1991-06-25	Smithkline Beecham Corporation	Phosphinic acid substituted steroids as inhibitors of steroid 5α-reductase
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
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
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
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
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
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
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
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
AU637247B2 (en) *	1990-08-01	1993-05-20	Merrell Dow Pharmaceuticals Inc.	4-amino-delta4-steroids and their use as 5alpha-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
AU642757B2 (en) *	1990-08-01	1993-10-28	Merrell Dow Pharmaceuticals Inc.	4-amino-delta4, 6-steroids and their use as 5alpha-reductase inhibitors
US5120847A (en) *	1990-08-27	1992-06-09	Merck & Co., Inc.	Process for iodinating or brominating the α-methylenic carbon of a secondary amide
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
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
US5061801A (en) *	1990-09-24	1991-10-29	Merck & Co., Inc.	Intermediate for making 3-oxo-4-aza-androst-1-ene 17β-ketones
CA2050824A1 (en) *	1990-09-24	1992-03-25	John M. Williams	Process for making 3-oxo-4-aza-androst-1-ene 17-.beta.-ketones
NZ241979A (en) *	1991-03-20	1996-01-26	Merck & Co Inc	Treatment of benign prostatic hyperplasia using 5alpha-reductase inhibitor and an alpha1-adrenergic recepter blocker
IL101245A0 (en) *	1991-03-20	1992-11-15	Merck & Co Inc	Pharmaceutical compositions for the treatment of prostatic cancer
WO1992018132A1 (en) *	1991-04-17	1992-10-29	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
DE69225244T2 (de) *	1991-12-20	1998-09-24	Glaxo Wellcome Inc	Inhibitoren von testosteron-5-alpha reductase.
JP3164389B2 (ja) *	1991-12-25	2001-05-08	三共株式会社	４−アザステロイド類
JPH07508032A (ja) *	1992-05-20	1995-09-07	メルク　エンド　カンパニー　インコーポレーテッド	５α−レダクターゼ阻害剤としての新規Δ−１７−及びΔ−２０オレフィン性並びに飽和１７β−置換４−アザ−５α−アンドロスタン−オン
DE69329149T2 (de) *	1992-05-20	2001-03-29	Merck & Co., Inc.	4-azasteroide als 5-alpha-reduktase
EP0649306B1 (en) *	1992-05-20	2001-01-10	Merck & Co. Inc.	Ester derivatives of 4-aza-steroids
JPH07508033A (ja) *	1992-05-20	1995-09-07	メルク　エンド　カンパニー　インコーポレーテッド	５α−レダクターゼ阻害剤としての３−オキソ−４−アザステロイドの新規１７−エステル，アミド及びケトン誘導体
WO1993023040A1 (en) *	1992-05-20	1993-11-25	Merck & Co., Inc.	17-ethers and thioethers of 4-aza-steroids
WO1993023420A1 (en) *	1992-05-20	1993-11-25	Merck & Co., Inc.	NEW 7β-SUBSTITUTED-4-AZA-5α-ANDROSTAN-3-ONES AS 5α-REDUCTASE INHIBITORS
FI945442A7 (fi) *	1992-05-20	1994-11-18	Merck & Co Inc	Uudet 7beta-substituoidut 4-atsa-5alfa-kolestanonit 5alfa-reduktaasi-i nhibiittoreina
WO1993023039A1 (en) *	1992-05-20	1993-11-25	Merck & Co., Inc.	Substituted 4-aza-5a-androstan-ones as 5a-reductase inhibitors
JPH07508034A (ja) *	1992-05-20	1995-09-07	メルク　エンド　カンパニー　インコーポレーテッド	１７−アミノ置換４−アザステロイド５α−レダクターゼ阻害剤
EP0641211A1 (en) *	1992-05-21	1995-03-08	Endorecherche Inc.	INHIBITORS OF TESTOSTERONE 5$g(a)-REDUCTASE ACTIVITY
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
DE69329933T2 (de) *	1992-10-06	2001-07-19	Merck & Co., Inc.	17-beta-carboxanilid derivate von 4-aza-5-alpha-androstan-3-one als 5-alpha-reduktase-hemmende arzneimittel
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

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Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0484094A2 (en) *	1990-10-29	1992-05-06	Sankyo Company Limited	Azasteroid compounds for the treatment of prostatic hypertrophy, their preparation and use

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CZ286069B6 (cs)	2000-01-12
SG52650A1 (en)	1998-09-28
DE10399022I1 (de)	2004-01-15
PL313492A1 (en)	1996-07-08
HUT73850A (en)	1996-09-30
SI0719278T1 (sl)	1998-06-30
ES2113127T3 (es)	1998-04-16
EP0719278A1 (en)	1996-07-03
HRP940563A2 (en)	1997-02-28
CN1057771C (zh)	2000-10-25
NO2003003I2 (no)	2007-06-11
BG100410A (bg)	1996-09-30
RO117455B1 (ro)	2002-03-29
ZA947118B (en)	1995-05-26
SK34796A3 (en)	1996-07-03
IS1713B (is)	1998-12-30
CY2219B1 (en)	2003-04-18
CZ74596A3 (en)	1996-09-11
SK281869B6 (sk)	2001-08-06
NZ274642A (en)	1997-11-24
RU2140926C1 (ru)	1999-11-10
DE69407978T2 (de)	1998-05-07
CA2170047C (en)	2004-11-09
AU7875194A (en)	1995-04-03
CA2170047A1 (en)	1995-03-23
CY2004002I1 (el)	2009-11-04
US5565467A (en)	1996-10-15
HRP940563B1 (en)	2000-10-31
NO961080D0 (no)	1996-03-15
BR1100329A (pt)	2000-06-13
SA94150231B1 (ar)	2005-05-04
NL300122I2 (nl)	2003-09-01
FI961231L (fi)	1996-03-15
OA10575A (en)	2002-06-25
IL110978A (en)	1999-01-26
PL180002B1 (pl)	2000-11-30
GR3026144T3 (en)	1998-05-29
DK0719278T3 (da)	1998-09-14
LU91027I2 (fr)	2004-04-28
TW369521B (en)	1999-09-11
DE69407978D1 (de)	1998-02-19
FI115216B (fi)	2005-03-31
US5846976A (en)	1998-12-08
KR100364953B1 (ko)	2003-04-08
NO961080L (no)	1996-03-15
HU220060B (hu)	2001-10-28
FI961231A0 (fi)	1996-03-15
NO306117B1 (no)	1999-09-20
PE15095A1 (es)	1995-06-04
AU690925B2 (en)	1998-05-07
CA2462061A1 (en)	1995-03-23
IL110978A0 (en)	1994-11-28
DE10399022I2 (de)	2012-09-13
JPH09502731A (ja)	1997-03-18
NL300122I1 (nl)	2003-06-02
EE03241B1 (et)	1999-12-15
WO1995007927A1 (en)	1995-03-23
ATE162199T1 (de)	1998-01-15
CY2004002I2 (el)	2009-11-04
HK1004334A1 (en)	1998-11-20
JP2904310B2 (ja)	1999-06-14
AP9400669A0 (en)	1994-10-31
MY119778A (en)	2005-07-29
BG62363B1 (bg)	1999-09-30
EP0719278B1 (en)	1998-01-14
CN1131424A (zh)	1996-09-18
ZA947119B (en)	1995-05-26
IS4205A (is)	1995-03-18
HU9600656D0 (en)	1996-05-28

Publication	Publication Date	Title
AP494A (en)	1996-05-15	Androstenone derivative.
HK1004334B (en)	1998-11-20	Androstenone derivative
EP0719277B1 (en)	1997-12-17	Androstenones
EP0674651B1 (en)	1998-10-28	Substituted 6-azaandrostenones
US5998427A (en)	1999-12-07	Androstenones
US5708001A (en)	1998-01-13	Substituted 6-azaandrostenones
US5817818A (en)	1998-10-06	Androstenones
JP3824636B2 (ja)	2006-09-20	アンドロステノン
WO1996030391A1 (en)	1996-10-03	Substituted 6-azacholesten-3-ones