UA80407C2 - 3-phenyl-2-arylalkylthiopropionic acid derivatives as selective agonists of parp-alpha - Google Patents

3-phenyl-2-arylalkylthiopropionic acid derivatives as selective agonists of parp-alpha Download PDF

Info

Publication number: UA80407C2
Authority: UA; Ukraine
Prior art keywords: phenyl; methylthio; dioxo; tetrahydro; carbamoyl
Prior art date: 2001-12-19

Application number

UA20040604534A

Other languages

English (en)

Ukrainian (uk)

Inventor

Lindstedt Eva-Lotte Alstermark

Original Assignee

Astrazeneca Ab

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.)

2001-12-19

Filing date

2002-12-18

Publication date

2007-09-25

2002-12-18 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-09-25 Publication of UA80407C2 publication Critical patent/UA80407C2/uk

Links

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- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A—HUMAN NECESSITIES
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
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Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Obesity (AREA)
Hematology (AREA)
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Cardiology (AREA)
Emergency Medicine (AREA)
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Epidemiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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UA20040604534A 2001-12-19 2002-12-18 3-phenyl-2-arylalkylthiopropionic acid derivatives as selective agonists of parp-alpha UA80407C2 (en)

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SE0104333A SE0104333D0 (sv)	2001-12-19	2001-12-19	Therapeutic agents
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US (1)	US7276539B2 (is)
EP (1)	EP1458677B1 (is)
JP (2)	JP3810770B2 (is)
KR (1)	KR20040068589A (is)
CN (1)	CN100343229C (is)
AR (1)	AR038046A1 (is)
AT (1)	ATE428691T1 (is)
AU (1)	AU2002352426A1 (is)
BR (1)	BR0215090A (is)
CA (1)	CA2470066C (is)
CO (1)	CO5590908A2 (is)
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RU (1)	RU2004117776A (is)
SE (1)	SE0104333D0 (is)
TW (1)	TW200410678A (is)
UA (1)	UA80407C2 (is)
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CA2489834C (en)	2002-06-20	2006-10-03	Astrazeneca Ab	Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance
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GB0314134D0 (en) *	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
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GB0427524D0 (en) *	2004-12-16	2005-01-19	Astrazeneca Ab	Chemical process
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AU2008221673B2 (en)	2007-03-08	2013-03-28	Albireo Ab	2 -substituted- 3 -phenylpropionic acid derivatives and their use in the treatment of inflammatory bowel disease

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5089514A (en)	1990-06-14	1992-02-18	Pfizer Inc.	3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents
US5232945A (en)	1992-07-20	1993-08-03	Pfizer Inc.	3-aryl-2-hydroxypropionic acid derivatives and analogs as antihypertensives
AU1903799A (en)	1997-12-05	1999-06-28	Eisai Co. Ltd.	Compositions and methods for modulating the activity of fibroblast growth factor
DE69941777D1 (de) *	1998-03-10	2010-01-21	Ono Pharmaceutical Co	Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten
MA26634A1 (fr) *	1998-06-04	2004-12-20	Astra Ab	Nouveaux derives de l'acide 3-aryl propionique et analogues
SE9801990D0 (sv)	1998-06-04	1998-06-04	Astra Ab	New 3-aryl propionic acid derivatives and analogs
SE9801992D0 (sv) *	1998-06-04	1998-06-04	Astra Ab	New 3-aryl-2-hydroxypropionic acid derivative I
GB9822473D0 (en) *	1998-10-16	1998-12-09	Glaxo Group Ltd	Chemical compounds
HRP20010795A2 (en)	1999-04-28	2003-02-28	Aventis Pharma Gmbh	Di-aryl acid derivatives as ppar receptor ligands
TWI262185B (en)	1999-10-01	2006-09-21	Eisai Co Ltd	Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives
TW574193B (en)	1999-12-03	2004-02-01	Astrazeneca Ab	Novel phenalkyloxy-phenyl derivatives, pharmaceutical composition containing the same and their uses
SE9904421D0 (sv)	1999-12-03	1999-12-03	Astra Ab	New compounds
SE0000772D0 (sv)	2000-03-08	2000-03-08	Astrazeneca Ab	Chemical compounds
MXPA02007603A (es)	2000-03-09	2003-02-24	Aventis Pharma Gmbh	Usos terapeuticos de mediadores ppar.
SE0003766D0 (sv)	2000-10-18	2000-10-18	Astrazeneca Ab	Novel formulation
EG26979A (en)	2000-12-21	2015-03-01	Astrazeneca Ab	Chemical compounds
TWI311133B (en)	2001-04-20	2009-06-21	Eisai R&D Man Co Ltd	Carboxylic acid derivativeand the salt thereof
SE0101978D0 (sv)	2001-06-01	2001-06-01	Astrazeneca Ab	New compounds
GB0121337D0 (en)	2001-09-04	2001-10-24	Astrazeneca Ab	Chemical compounds
GB0121621D0 (en)	2001-09-07	2001-10-31	Astrazeneca Ab	Chemical compounds
GB0121622D0 (en)	2001-09-07	2001-10-31	Astrazeneca Ab	Chemical compounds
MY131995A (en)	2001-09-08	2007-09-28	Astrazeneca Ab	Benzothiazepine and benzothiadiazepine derivatives with illeal bile acid transport (ibat) inhibitory activity for the treatment hyperlipidaemia
SE0104334D0 (sv)	2001-12-19	2001-12-19	Astrazeneca Ab	Therapeutic agents
GB0229931D0 (en)	2002-12-21	2003-01-29	Astrazeneca Ab	Therapeutic agents
GB0209467D0 (en)	2002-04-25	2002-06-05	Astrazeneca Ab	Chemical compounds
GB0213669D0 (en)	2002-06-14	2002-07-24	Astrazeneca Ab	Chemical compounds
SE0201936D0 (sv)	2002-06-20	2002-06-20	Astrazeneca Ab	Therapeutic agents
CA2489834C (en)	2002-06-20	2006-10-03	Astrazeneca Ab	Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance
SE0201937D0 (sv)	2002-06-20	2002-06-20	Astrazeneca Ab	Therapeutic agents
GB0314129D0 (en)	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314078D0 (en)	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314131D0 (en)	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314136D0 (en)	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314075D0 (en)	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314130D0 (en) *	2003-06-18	2003-07-23	Astrazeneca Ab	Therapeutic agents
GB0314260D0 (en)	2003-06-19	2003-07-23	Astrazeneca Ab	Therapeutic agents

2001
- 2001-12-19 SE SE0104333A patent/SE0104333D0/xx unknown
2002
- 2002-12-18 HU HU0402093A patent/HUP0402093A3/hu unknown
- 2002-12-18 PL PL02370623A patent/PL370623A1/xx unknown
- 2002-12-18 CA CA002470066A patent/CA2470066C/en not_active Expired - Fee Related
- 2002-12-18 NZ NZ533365A patent/NZ533365A/en unknown
- 2002-12-18 US US10/499,042 patent/US7276539B2/en not_active Expired - Fee Related
- 2002-12-18 AU AU2002352426A patent/AU2002352426A1/en not_active Abandoned
- 2002-12-18 MX MXPA04005992A patent/MXPA04005992A/es not_active Application Discontinuation
- 2002-12-18 DE DE60232018T patent/DE60232018D1/de not_active Expired - Lifetime
- 2002-12-18 WO PCT/GB2002/005743 patent/WO2003051826A1/en not_active Ceased
- 2002-12-18 UA UA20040604534A patent/UA80407C2/uk unknown
- 2002-12-18 RU RU2004117776/04A patent/RU2004117776A/ru not_active Application Discontinuation
- 2002-12-18 AT AT02788144T patent/ATE428691T1/de not_active IP Right Cessation
- 2002-12-18 TW TW091136517A patent/TW200410678A/zh unknown
- 2002-12-18 BR BR0215090-5A patent/BR0215090A/pt not_active IP Right Cessation
- 2002-12-18 JP JP2003552714A patent/JP3810770B2/ja not_active Expired - Fee Related
- 2002-12-18 CN CNB028281225A patent/CN100343229C/zh not_active Expired - Fee Related
- 2002-12-18 KR KR10-2004-7009348A patent/KR20040068589A/ko not_active Withdrawn
- 2002-12-18 EP EP02788144A patent/EP1458677B1/en not_active Expired - Lifetime
- 2002-12-18 ES ES02788144T patent/ES2324025T3/es not_active Expired - Lifetime
- 2002-12-18 IL IL16237802A patent/IL162378A0/xx unknown
- 2002-12-19 AR ARP020105003A patent/AR038046A1/es not_active Application Discontinuation
2004
- 2004-06-08 IS IS7303A patent/IS7303A/is unknown
- 2004-06-09 ZA ZA200404585A patent/ZA200404585B/en unknown
- 2004-07-16 NO NO20043084A patent/NO20043084L/no not_active Application Discontinuation
- 2004-07-16 CO CO04068143A patent/CO5590908A2/es not_active Application Discontinuation
2006
- 2006-03-20 JP JP2006077296A patent/JP2006241162A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
CO5590908A2 (es)	2005-12-30
ZA200404585B (en)	2005-10-26
NO20043084L (no)	2004-07-16
JP3810770B2 (ja)	2006-08-16
NZ533365A (en)	2006-05-26
AR038046A1 (es)	2004-12-22
HUP0402093A2 (hu)	2005-02-28
IS7303A (is)	2004-06-08
PL370623A1 (en)	2005-05-30
HUP0402093A3 (en)	2008-08-28
BR0215090A (pt)	2004-11-16
JP2005511785A (ja)	2005-04-28
US7276539B2 (en)	2007-10-02
EP1458677B1 (en)	2009-04-15
EP1458677A1 (en)	2004-09-22
CA2470066C (en)	2007-04-10
IL162378A0 (en)	2005-11-20
AU2002352426A1 (en)	2003-06-30
CN1620430A (zh)	2005-05-25
CN100343229C (zh)	2007-10-17
JP2006241162A (ja)	2006-09-14
HK1068866A1 (en)	2005-05-06
US20050215630A1 (en)	2005-09-29
WO2003051826A1 (en)	2003-06-26
RU2004117776A (ru)	2006-01-10
ATE428691T1 (de)	2009-05-15
TW200410678A (en)	2004-07-01
CA2470066A1 (en)	2003-06-26
ES2324025T3 (es)	2009-07-29
KR20040068589A (ko)	2004-07-31
MXPA04005992A (es)	2004-09-27
SE0104333D0 (sv)	2001-12-19
DE60232018D1 (de)	2009-05-28

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TWI253444B (en)	2006-04-21	Therapeutic agents
AU2003290309B2 (en)	2007-01-18	Therapeutic agents
AU2003240101B2 (en)	2006-09-21	Benzoic acid derivatives as modulators of PPAR alpha and gamma
UA77574C2 (en)	2006-12-15	Method for metal strip heat treatment
JP3810770B2 (ja)	2006-08-16	ＰＰＡＲαの選択的アンタゴニストとしての３−フェニル−２−アリールアルキルチオプロピオン酸誘導体
JP3782818B2 (ja)	2006-06-07	インスリン抵抗性の処置のためのオルト置換安息香酸誘導体
KR20060023994A (ko)	2006-03-15	치료제
AU2004249494B2 (en)	2008-03-20	2-ethoxy-3-phenylpropionic acid derivatives for the treatment of lipid disorders
UA76627C2 (en)	2006-08-15	Benzoic acid derivatives with ortho-substituents for treating insulin resistance
AU2004249485A1 (en)	2004-12-29	Potassium or sodium salt of (-)-2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoic acid and their use in medicine
HK1068866B (en)	2009-09-11	3-phenyl-2-arylalkylthiopropionic acid derivatives as selective agonists of ppar-alpha