SK10972002A3 - Duálne inhibítory cholesterylesteru a syntéza voskového esteru na liečenie ochorení tukových žliaz - Google Patents

Duálne inhibítory cholesterylesteru a syntéza voskového esteru na liečenie ochorení tukových žliaz Download PDF

Info

Publication number: SK10972002A3
Authority: SK; Slovakia
Prior art keywords: acne; acetyl; triisopropylphenyl; sulfamic acid; ester
Prior art date: 2000-02-02

Application number

SK1097-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Reynold Homan

Original Assignee

Warner-Lambert Company

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.)

2000-02-02

Filing date

2001-01-23

Publication date

2003-07-01

2001-01-23 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2003-07-01 Publication of SK10972002A3 publication Critical patent/SK10972002A3/sk

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Classifications

- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- 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

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

SK1097-2002A 2000-02-02 2001-01-23 Duálne inhibítory cholesterylesteru a syntéza voskového esteru na liečenie ochorení tukových žliaz SK10972002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US17977800P	2000-02-02	2000-02-02
PCT/US2001/002190 WO2001056556A2 (fr)	2000-02-02	2001-01-23	Doubles inhibiteurs de la synthese d'ester de choslesteryle et d'ester de cire utilises dans le traitement des troubles des glandes sebacees

Publications (1)

Publication Number	Publication Date
SK10972002A3 true SK10972002A3 (sk)	2003-07-01

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Application Number	Title	Priority Date	Filing Date
SK1097-2002A SK10972002A3 (sk)	2000-02-02	2001-01-23	Duálne inhibítory cholesterylesteru a syntéza voskového esteru na liečenie ochorení tukových žliaz

Country Status (34)

Country	Link
US (2)	US6730703B2 (fr)
EP (1)	EP1263421B1 (fr)
JP (1)	JP2003531113A (fr)
KR (1)	KR20020073574A (fr)
CN (1)	CN1398182A (fr)
AP (1)	AP2002002612A0 (fr)
AT (1)	ATE295724T1 (fr)
AU (1)	AU781563B2 (fr)
BG (1)	BG107042A (fr)
BR (1)	BR0107954A (fr)
CA (1)	CA2398219A1 (fr)
CR (1)	CR6712A (fr)
DE (1)	DE60110897T2 (fr)
DZ (1)	DZ3288A1 (fr)
EA (1)	EA004255B1 (fr)
EE (1)	EE200200429A (fr)
ES (1)	ES2239145T3 (fr)
GE (1)	GEP20043286B (fr)
HR (1)	HRP20020717A2 (fr)
HU (1)	HUP0301010A3 (fr)
IL (1)	IL150865A0 (fr)
IS (1)	IS6478A (fr)
MA (1)	MA26872A1 (fr)
MX (1)	MXPA02007309A (fr)
NO (1)	NO20023659L (fr)
NZ (1)	NZ520330A (fr)
OA (1)	OA12173A (fr)
PL (1)	PL357041A1 (fr)
PT (1)	PT1263421E (fr)
SK (1)	SK10972002A3 (fr)
UA (1)	UA75345C2 (fr)
WO (1)	WO2001056556A2 (fr)
YU (1)	YU57502A (fr)
ZA (1)	ZA200206075B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1281399A3 (fr) *	2001-08-01	2004-02-11	Warner-Lambert Company	Inhibiteurs doubles de la synthèse des des esters de cires et des esters du cholestérol pour inhiber la production de sébum
US20050031699A1 (en)	2003-06-26	2005-02-10	L'oreal	Porous particles loaded with cosmetically or pharmaceutically active compounds
AU2004280134B2 (en)	2003-10-09	2007-10-11	Medicis Pharmaceutical Corporation	Pharmaceutical compositions comprising malonamide derivatives for decreasing sebum production
EP1856029A1 (fr)	2005-02-24	2007-11-21	Warner-Lambert Company LLC	Inhibiteur cristallin de la acat
FR2903999B1 (fr) *	2006-07-19	2008-09-05	Galderma Res & Dev S N C Snc	Modulateurs de sc4mol dans le traitement de l'acne ou de l'hyperseborrhee
FR2904002A1 (fr) *	2006-07-19	2008-01-25	Galderma Res & Dev S N C Snc	Modulateurs de la lanosterol synthetase dans le traitement de l'acne ou de l'hyperseborrhee
FR2938342A1 (fr) *	2008-11-13	2010-05-14	Galderma Res & Dev	Ciblage de modulateurs de ces1 et/ou ces3 dans le traitement de l'acne, d'une dermatite seborrheique ou de l'hyperseborrhee
US20100226983A1 (en)	2009-01-28	2010-09-09	Nanobio Corporation	Compositions for treatment and prevention of acne, methods of making the compositions, and methods of use thereof
AU2019290231A1 (en) *	2018-06-21	2020-12-17	Dermavant Sciences GmbH	Topical formulations of DGAT1 inhibitors and their methods of use

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4545977A (en) *	1985-01-11	1985-10-08	G. D. Searle & Co.	Compositions and methods for treating severe acne with isotretinoin
US4751026A (en)	1986-03-24	1988-06-14	Warner-Lambert Company	Substituted anilides of oleic, linoleic, or linolenic acid as inhibitors of acyl-coa:cholesterol acyltransferase
US4722927A (en)	1986-04-28	1988-02-02	Warner-Lambert Company	Pyrimidine amides of oleic or linoleic acid, composition containing them and their use as inhibitors of acyl-CoA cholesterol acyltransferase
JPS6323848A (ja)	1986-07-11	1988-02-01	ワ−ナ−−ランバ−ト・コンパニ−	Ω−（置換フエニルオキシ）−アルカン酸のアリ−ル−およびアラルキルアミド
US4716175A (en)	1987-02-24	1987-12-29	Warner-Lambert Company	Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase
US5015644A (en)	1987-06-02	1991-05-14	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic urea and carbamate compounds
IE61716B1 (en)	1987-06-02	1994-11-30	Warner Lambert Co	Antihyperlipidemic and antiatherosclerotic urea compounds
JPH0193569A (ja)	1987-07-02	1989-04-12	Warner Lambert Co	アシル‐ＣｏＡ：コレステロールアシルトランスフエラーゼのＮ‐〔（２，６‐ジ置換）フエニル〕尿素およびカルバメート阻害剤
US4948806A (en)	1988-03-30	1990-08-14	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic compounds and compositions
US4868210A (en)	1988-03-30	1989-09-19	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic compounds and compositions
US5030653A (en)	1988-03-30	1991-07-09	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic compounds and compositions
US4999373A (en)	1988-03-30	1991-03-12	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic compounds and compositions
US5116848A (en)	1988-03-30	1992-05-26	Warner-Lambert Company	N-(((2,6-disubstituted)phenyl)-n-diarylalkyl)ureas as antihyperlipidemic and antiatherosclerotic agents
US5155127A (en)	1989-02-09	1992-10-13	Warner-Lambert Company	N-(substituted aryl)-n'-(substituted alkoxy)-ureas and thioureas as antihypercholesterolemic and antiatherosclerotic agents
US4923896A (en)	1989-02-09	1990-05-08	Warner-Lambert Company	N-(substituted aryl)-N'-(substituted alkoxy)-ureas and thioureas as antihypercholesterolemic and antiatherosclerotic agents
US4994465A (en)	1989-02-17	1991-02-19	Warner-Lambert Company	Antihyperlipidemic and antiatherosclerotic trisubstituted urea compounds
AU632809B2 (en)	1989-05-25	1993-01-14	Takeda Chemical Industries Ltd.	Benzocycloalkane benzopyran and benzothiopyran urea derivatives and production thereof
AU629376B2 (en)	1989-08-04	1992-10-01	Mitsubishi Chemical Corporation	1-phenylalkyl-3-phenylurea derivatives
WO1991004027A1 (fr)	1989-09-15	1991-04-04	Pfizer Inc.	Nouveaux derives de n-aryle de n-heteroarylamide et d'uree en tant qu'inhibiteurs d'acyl coenzyme a: cholesterol acyl transferase
TW205037B (fr)	1989-10-06	1993-05-01	Takeda Pharm Industry Co Ltd
JPH05310678A (ja)	1990-01-22	1993-11-22	Mitsubishi Kasei Corp	１−フェニルアルキル−３−フェニル尿素誘導体
US5362878A (en)	1991-03-21	1994-11-08	Pfizer Inc.	Intermediates for making N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase (ACAT)
JP2668163B2 (ja)	1992-01-23	1997-10-27	ファイザーインク．	コレステロール血症および抗アテローム動脈硬化症薬としての４−アリール−３−（ヘテロアリールウレイド）−１，２−ジヒドロ−２−オキソ−キノリン誘導体
WO1993024458A1 (fr)	1992-05-28	1993-12-09	Pfizer Inc.	Nouveau derives n-aryle et de n-heteroaryluree en tant qu'inhibiteurs de l'acylcoenzime a: cholesterol acyltransferase (acat)
US5565472A (en)	1992-12-21	1996-10-15	Pfizer Inc.	4-aryl-3-(heteroarylureido)-1,2-dihydro-2-oxo-quinoline derivatives as antihypercholesterolemic and antiatherosclerotic agents
US5491172A (en)	1993-05-14	1996-02-13	Warner-Lambert Company	N-acyl sulfamic acid esters (or thioesters), N-acyl sulfonamides, and N-sulfonyl carbamic acid esters (or thioesters) as hypercholesterolemic agents
US5596001A (en)	1993-10-25	1997-01-21	Pfizer Inc.	4-aryl-3-(heteroarylureido)quinoline derivatves
US5494172A (en) *	1994-05-12	1996-02-27	Miller Compressing Company	Magnetic pulley assembly
US6133326A (en) *	1994-08-31	2000-10-17	Pfizer Inc	Compositions and methods for decreasing sebum production
ATE248845T1 (de) *	1998-06-25	2003-09-15	Tularik Inc	Arylsulfonanilid-phosphate
AU2001292874B2 (en) *	2000-09-27	2006-06-15	Merck & Co., Inc.	Benzopyrancarboxylic acid derivatives for the treatment of diabetes and lipid disorders

2001
- 2001-01-23 GE GEAP20016597A patent/GEP20043286B/en unknown
- 2001-01-23 US US10/182,847 patent/US6730703B2/en not_active Expired - Fee Related
- 2001-01-23 DZ DZ013288A patent/DZ3288A1/fr active
- 2001-01-23 MX MXPA02007309A patent/MXPA02007309A/es active IP Right Grant
- 2001-01-23 DE DE60110897T patent/DE60110897T2/de not_active Expired - Fee Related
- 2001-01-23 EE EEP200200429A patent/EE200200429A/xx unknown
- 2001-01-23 EP EP01948936A patent/EP1263421B1/fr not_active Expired - Lifetime
- 2001-01-23 NZ NZ520330A patent/NZ520330A/en unknown
- 2001-01-23 BR BR0107954-9A patent/BR0107954A/pt not_active Application Discontinuation
- 2001-01-23 HU HU0301010A patent/HUP0301010A3/hu unknown
- 2001-01-23 PT PT01948936T patent/PT1263421E/pt unknown
- 2001-01-23 PL PL01357041A patent/PL357041A1/xx not_active Application Discontinuation
- 2001-01-23 YU YU57502A patent/YU57502A/sh unknown
- 2001-01-23 AP APAP/P/2002/002612A patent/AP2002002612A0/en unknown
- 2001-01-23 CN CN01804520A patent/CN1398182A/zh active Pending
- 2001-01-23 ES ES01948936T patent/ES2239145T3/es not_active Expired - Lifetime
- 2001-01-23 SK SK1097-2002A patent/SK10972002A3/sk not_active Application Discontinuation
- 2001-01-23 UA UA2002076160A patent/UA75345C2/uk unknown
- 2001-01-23 AT AT01948936T patent/ATE295724T1/de not_active IP Right Cessation
- 2001-01-23 WO PCT/US2001/002190 patent/WO2001056556A2/fr not_active Ceased
- 2001-01-23 HR HR20020717A patent/HRP20020717A2/hr not_active Application Discontinuation
- 2001-01-23 IL IL15086501A patent/IL150865A0/xx unknown
- 2001-01-23 JP JP2001556248A patent/JP2003531113A/ja active Pending
- 2001-01-23 KR KR1020027009943A patent/KR20020073574A/ko not_active Ceased
- 2001-01-23 EA EA200200764A patent/EA004255B1/ru not_active IP Right Cessation
- 2001-01-23 CA CA002398219A patent/CA2398219A1/fr not_active Abandoned
- 2001-01-23 OA OA1200200234A patent/OA12173A/en unknown
- 2001-01-23 AU AU29718/01A patent/AU781563B2/en not_active Ceased
2002
- 2002-07-19 IS IS6478A patent/IS6478A/is unknown
- 2002-07-24 CR CR6712A patent/CR6712A/es not_active Application Discontinuation
- 2002-07-30 ZA ZA200206075A patent/ZA200206075B/en unknown
- 2002-08-01 NO NO20023659A patent/NO20023659L/no not_active Application Discontinuation
- 2002-08-01 MA MA26756A patent/MA26872A1/fr unknown
- 2002-08-29 BG BG107042A patent/BG107042A/bg unknown
2004
- 2004-02-06 US US10/773,354 patent/US20040161393A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EA200200764A1 (ru)	2002-12-26
CR6712A (es)	2004-01-14
PL357041A1 (en)	2004-07-12
AU781563B2 (en)	2005-06-02
PT1263421E (pt)	2005-08-31
HRP20020717A2 (en)	2003-12-31
OA12173A (en)	2006-05-08
MA26872A1 (fr)	2004-12-20
BR0107954A (pt)	2002-10-22
ZA200206075B (en)	2003-10-30
NO20023659D0 (no)	2002-08-01
IL150865A0 (en)	2003-02-12
KR20020073574A (ko)	2002-09-27
ES2239145T3 (es)	2005-09-16
GEP20043286B (en)	2004-07-26
CN1398182A (zh)	2003-02-19
CA2398219A1 (fr)	2001-08-09
ATE295724T1 (de)	2005-06-15
DE60110897D1 (de)	2005-06-23
HUP0301010A2 (hu)	2003-08-28
MXPA02007309A (es)	2002-11-29
AP2002002612A0 (en)	2002-09-30
AU2971801A (en)	2001-08-14
EA004255B1 (ru)	2004-02-26
EP1263421B1 (fr)	2005-05-18
WO2001056556A3 (fr)	2002-03-07
US20030060507A1 (en)	2003-03-27
JP2003531113A (ja)	2003-10-21
EP1263421A2 (fr)	2002-12-11
WO2001056556A2 (fr)	2001-08-09
NO20023659L (no)	2002-09-25
US6730703B2 (en)	2004-05-04
IS6478A (is)	2002-07-19
DE60110897T2 (de)	2006-03-23
DZ3288A1 (en)	2001-08-09
EE200200429A (et)	2003-12-15
US20040161393A1 (en)	2004-08-19
UA75345C2 (en)	2006-04-17
BG107042A (bg)	2003-04-30
YU57502A (sh)	2006-01-16
NZ520330A (en)	2004-02-27
HUP0301010A3 (en)	2005-03-29

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Date	Code	Title	Description
2010-02-08	FC9A	Refused patent application

Publication	Publication Date	Title
EP0098743B1 (fr)	1988-09-28	Dérivés de phényl-alpha-acyloxyacétamides et leur utilisation thérapeutique
US8679552B2 (en)	2014-03-25	Acne vulgaris treatment regimen
RU2619851C2 (ru)	2017-05-18	Композиция, включающая дииндолилметан и ретиноид для лечения кожной патологии
US6133326A (en)	2000-10-17	Compositions and methods for decreasing sebum production
JPH07196497A (ja)	1995-08-01	アクネ又は脂漏症を阻止するのに適した医薬組成物
HUP0202548A2 (hu)	2003-02-28	Faggyútermelés gátlásánál alkalmazható viaszészter- és koleszterilészter-szintézist gátló kettős inhibitorok és ezeket tartalmazó gyógyszerkészítmények
US3934028A (en)	1976-01-20	Acne and psoriasis treatment with retinoic acid analogs
US4588750A (en)	1986-05-13	Therapeutic compositions for reducing sebum secretion
US4021573A (en)	1977-05-03	Psoriasis treatment with retinoic acid analogs
SK10972002A3 (sk)	2003-07-01	Duálne inhibítory cholesterylesteru a syntéza voskového esteru na liečenie ochorení tukových žliaz
JPH0899889A (ja)	1996-04-16	アトピー性皮膚炎治療剤
US4035510A (en)	1977-07-12	Treatment of acne utilizing N-methyldiethanolamine
US5369126A (en)	1994-11-29	Nonatetraenoic acid derivative for use in treating acne
JPS58103319A (ja)	1983-06-20	皮膚塗布用組成物
JPS6360935A (ja)	1988-03-17	皮脂抑制用外用剤
JPH0449216A (ja)	1992-02-18	メラニン抑制剤
HK1001375A1 (en)	1998-06-19	Use of acetylsalicylic acid in the manufacture of a drug for the treatment of skin injuries