CA2543122A1 - 3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety - Google Patents

3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety Download PDF

Info

Publication number: CA2543122A1
Authority: CA; Canada
Prior art keywords: formula; compound; group; ring; alkyl
Prior art date: 2003-10-23
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002543122A

Other languages

English (en)

French (fr)

Inventor

Kevin K Barvian

Anthony L Handlon

Donald L Hertzog

Clifton E Hyman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Individual

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.)

2003-10-23

Filing date

2004-10-21

Publication date

2005-05-12

2004-10-21 Application filed by Individual filed Critical Individual

2005-05-12 Publication of CA2543122A1 publication Critical patent/CA2543122A1/en

Status Abandoned legal-status Critical Current

Links

208000008589 Obesity Diseases 0.000 title claims abstract description 25
235000020824 obesity Nutrition 0.000 title claims abstract description 25
238000011282 treatment Methods 0.000 title claims abstract description 20
206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 16
208000019901 Anxiety disease Diseases 0.000 title claims abstract description 13
239000005557 antagonist Substances 0.000 title claims abstract description 13
230000036506 anxiety Effects 0.000 title claims abstract description 13
LVAGVGLOKJYPSZ-UHFFFAOYSA-N 3-(4-aminophenyl)thieno[3,2-d]pyrimidin-4-one Chemical class C1=CC(N)=CC=C1N1C(=O)C(SC=C2)=C2N=C1 LVAGVGLOKJYPSZ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 141
238000000034 method Methods 0.000 claims abstract description 42
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
239000003814 drug Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 36
-1 hydroxy, cyano, acetyl Chemical group 0.000 claims description 35
239000012453 solvate Substances 0.000 claims description 34
125000005843 halogen group Chemical group 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 14
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000004953 trihalomethyl group Chemical group 0.000 claims description 10
125000004043 oxo group Chemical group O=* 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004951 trihalomethoxy group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
JOAYEJZDGOLEDZ-QGZVFWFLSA-N 6-(4-chlorophenyl)-3-[4-[(3r)-3-hydroxypyrrolidin-1-yl]-3-methoxyphenyl]thieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CC[C@@H](O)C1 JOAYEJZDGOLEDZ-QGZVFWFLSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
241000894007 species Species 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
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238000010168 coupling process Methods 0.000 claims description 3
238000005859 coupling reaction Methods 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
SYEXCHNVDLNLJK-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-(3-methoxy-4-pyrrolidin-1-ylphenyl)thieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CCCC1 SYEXCHNVDLNLJK-UHFFFAOYSA-N 0.000 claims description 2
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239000007868 Raney catalyst Substances 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
238000006619 Stille reaction Methods 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
239000012190 activator Substances 0.000 claims description 2
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150000001413 amino acids Chemical class 0.000 claims description 2
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ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
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JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical group OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 2
229940044551 receptor antagonist Drugs 0.000 claims description 2
239000002464 receptor antagonist Substances 0.000 claims description 2
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WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
JOAYEJZDGOLEDZ-KRWDZBQOSA-N 6-(4-chlorophenyl)-3-[4-[(3s)-3-hydroxypyrrolidin-1-yl]-3-methoxyphenyl]thieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CC[C@H](O)C1 JOAYEJZDGOLEDZ-KRWDZBQOSA-N 0.000 claims 1
JWZFGZYJZKNIMR-QGZVFWFLSA-N 6-(4-fluorophenyl)-3-[4-[(3r)-3-hydroxypyrrolidin-1-yl]-3-methoxyphenyl]thieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC(F)=CC=2)=O)=CC=C1N1CC[C@@H](O)C1 JWZFGZYJZKNIMR-QGZVFWFLSA-N 0.000 claims 1
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
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Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hematology (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
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Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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CA002543122A 2003-10-23 2004-10-21 3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety Abandoned CA2543122A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US51380003P	2003-10-23	2003-10-23
US60/513,800		2003-10-23
PCT/US2004/034846 WO2005042541A1 (en)	2003-10-23	2004-10-21	3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety

Publications (1)

Publication Number	Publication Date
CA2543122A1 true CA2543122A1 (en)	2005-05-12

Family

ID=34549304

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002543122A Abandoned CA2543122A1 (en)	2003-10-23	2004-10-21	3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety

Country Status (15)

Country	Link
US (1)	US20070078125A1 (2)
EP (1)	EP1678184A1 (2)
JP (1)	JP2007509158A (2)
KR (1)	KR20060100412A (2)
CN (1)	CN1871242A (2)
AU (1)	AU2004285913A1 (2)
BR (1)	BRPI0415667A (2)
CA (1)	CA2543122A1 (2)
CO (1)	CO5690599A2 (2)
IL (1)	IL174693A0 (2)
MA (1)	MA28111A1 (2)
MX (1)	MXPA06003997A (2)
NO (1)	NO20061909L (2)
WO (1)	WO2005042541A1 (2)
ZA (1)	ZA200603181B (2)

Families Citing this family (22)

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JP2009501217A (ja) *	2005-07-15	2009-01-15	アストラゼネカアクチボラグ	治療薬
CN101273026A (zh)	2005-09-30	2008-09-24	霍夫曼-拉罗奇有限公司	作为mch受体拮抗剂的茚满衍生物
US8618115B2 (en) *	2005-10-26	2013-12-31	Bristol-Myers Squibb Company	Substituted thieno[3,2-d]pyrimidinones as MCHR1 antagonists and methods for using them
US7745447B2 (en) *	2005-10-26	2010-06-29	Bristol-Myers Squibb Company	Substituted thieno[3,2-D]pyrimidines as non-basic melanin concentrating hormone receptor-1 antagonists
US8329704B2 (en)	2005-12-21	2012-12-11	Janssen Pharmaceutica, N.V.	Substituted pyrazinone derivatives for use in MCH-1 mediated diseases
US7553836B2 (en)	2006-02-06	2009-06-30	Bristol-Myers Squibb Company	Melanin concentrating hormone receptor-1 antagonists
EP1987020B1 (en) *	2006-02-15	2012-10-03	Sanofi	Azacyclyl-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments
WO2007093365A2 (en) *	2006-02-15	2007-08-23	Sanofi-Aventis	Novel amino alcohol-substituted arylthienopyrimidinones, process for their preparation and their use as medicaments
EP1986646A1 (en)	2006-02-15	2008-11-05	Sanofi-Aventis	Novel azacycly-substituted arylthienopyrimidinones, process for their preparation and their use as medicaments
KR20080094699A (ko) *	2006-02-15	2008-10-23	사노피-아벤티스	신규 아미노알콜-치환된 아릴디하이드로이소퀴놀리논, 이의제조 방법 및 이의 약물로서의 용도
MX2008015662A (es) *	2006-06-08	2009-01-12	Lilly Co Eli	Nuevos receptores antagonistas de la hormona concentradora de melanina (mch).
WO2008020799A1 (en)	2006-08-18	2008-02-21	Astrazeneca Ab	Thienopyrimidin-4-one and thienopyridazin-7-one derivatives as mch rl antagonists
EP2121654A1 (en)	2007-01-10	2009-11-25	Albany Molecular Research, Inc.	5-pyridinone substituted indazoles
JP2010525077A (ja)	2007-04-25	2010-07-22	ブリストル−マイヤーズスクイブカンパニー	非塩基性メラニン凝集ホルモン受容体−１アンタゴニスト
KR20100044225A (ko)	2007-07-21	2010-04-29	알바니 몰레큘라 리써치, 인크.	5-피리디논 치환된 인다졸
PE20091928A1 (es)	2008-05-29	2009-12-31	Bristol Myers Squibb Co	Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos
WO2010104818A1 (en) *	2009-03-09	2010-09-16	Bristol-Myers Squibb Company	Aza pyridone analogs useful as melanin concentrating hormone receptor-1 antagonists
HUP1100241A3 (en)	2011-05-06	2013-12-30	Richter Gedeon Nyrt	Oxetane substituted pyrimidones
KR20130013199A (ko) *	2011-07-27	2013-02-06	한미약품 주식회사	신규 피리미딘 유도체 및 이를 활성성분으로 포함하는 약학 조성물
EP2747693B1 (en)	2011-08-26	2018-05-09	ON Light Sciences, Inc.	Tattoo removal system and method
AU2021206286A1 (en) *	2020-01-10	2024-08-08	Consynance Therapeutics, Inc.	Therapeutic combinations of drugs and methods of using them
HUP2200222A1 (hu)	2022-06-17	2023-12-28	Richter Gedeon Nyrt	MCHR1 antagonisták a Prader-Willi szindróma kezelésére

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2004
- 2004-10-21 US US10/576,765 patent/US20070078125A1/en not_active Abandoned
- 2004-10-21 AU AU2004285913A patent/AU2004285913A1/en not_active Abandoned
- 2004-10-21 MX MXPA06003997A patent/MXPA06003997A/es unknown
- 2004-10-21 KR KR1020067009417A patent/KR20060100412A/ko not_active Withdrawn
- 2004-10-21 CA CA002543122A patent/CA2543122A1/en not_active Abandoned
- 2004-10-21 BR BRPI0415667-6A patent/BRPI0415667A/pt not_active IP Right Cessation
- 2004-10-21 WO PCT/US2004/034846 patent/WO2005042541A1/en not_active Ceased
- 2004-10-21 JP JP2006536779A patent/JP2007509158A/ja active Pending
- 2004-10-21 EP EP04795941A patent/EP1678184A1/en not_active Withdrawn
- 2004-10-21 CN CNA2004800313000A patent/CN1871242A/zh active Pending
2006
- 2006-03-30 IL IL174693A patent/IL174693A0/en unknown
- 2006-04-20 ZA ZA200603181A patent/ZA200603181B/en unknown
- 2006-04-21 CO CO06038136A patent/CO5690599A2/es not_active Application Discontinuation
- 2006-04-25 MA MA28965A patent/MA28111A1/fr unknown
- 2006-04-28 NO NO20061909A patent/NO20061909L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA200603181B (en)	2008-01-30
JP2007509158A (ja)	2007-04-12
US20070078125A1 (en)	2007-04-05
MXPA06003997A (es)	2006-07-05
BRPI0415667A (pt)	2006-12-19
CO5690599A2 (es)	2006-10-31
WO2005042541A1 (en)	2005-05-12
KR20060100412A (ko)	2006-09-20
EP1678184A1 (en)	2006-07-12
MA28111A1 (fr)	2006-08-01
NO20061909L (no)	2006-05-03
IL174693A0 (en)	2006-08-20
CN1871242A (zh)	2006-11-29
AU2004285913A1 (en)	2005-05-12

Legal Events

Date	Code	Title	Description
2007-01-16	EEER	Examination request
2008-10-21	FZDE	Discontinued

Publication	Publication Date	Title
CA2543122A1 (en)	2005-05-12	3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety
EP1543011B1 (en)	2006-05-03	Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine h4 receptor ligands
DE69719191T2 (de)	2003-11-27	Tetrahydroisoquinoline derivate als modulatoren von dopamine d3 rezeptoren
JP5277256B2 (ja)	2013-08-28	ｍａｘｉ−Ｋチャネル開口薬としてのピリミジン、ピリジン及びトリアジン誘導体
BG107438A (bg)	2003-09-30	Циклопентаноиндоли, състави, които ги съдържат, иметоди за лечение
KR20070097441A (ko)	2007-10-04	11-β 하이드록실 스테로이드 데하이드로게나제 유형 1의억제제 및 이를 사용하는 방법
KR20070024639A (ko)	2007-03-02	아미도 화합물 및 약제로서의 이의 용도
KR101216296B1 (ko)	2012-12-28	티에노피리디논 화합물 및 치료 방법
CN101146776A (zh)	2008-03-19	治疗炎性疾病的pgd2受体拮抗剂
WO2003057161A2 (en)	2003-07-17	BENZOTHIENO [3,2-c]PYRAZOLYL AND BENZOFURANO [3,2-c] PYRAZOLYL COMPOUNDS, THEIR USE IN DISEASES ASSOCIATED WITH THE 5-HT2C RECEPTOR AND INTERMEDIATE COMPOUNDS THEREOF
JP5227806B2 (ja)	2013-07-03	三環性化合物およびその医薬用途
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JP2010509402A (ja)	2010-03-25	Ａ１アデノシン受容体のアロステリック調節剤
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