NL1027084C2 - Gesubstitueerde triazoolderivaten als oxytocine-antagonisten. - Google Patents

Gesubstitueerde triazoolderivaten als oxytocine-antagonisten. Download PDF

Info

Publication number: NL1027084C2
Authority: NL; Netherlands
Prior art keywords: triazol; methoxypyridin; methyl; fluoro; pyrazine
Prior art date: 2003-09-22

Application number

NL1027084A

Other languages

English (en)

Dutch (nl)

Other versions

NL1027084A1 (nl

Inventor

Alan Daniel Brown

David Ellis

Christopher Ronald Smith

Original Assignee

Pfizer

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.)

2003-09-22

Filing date

2004-09-22

Publication date

2006-01-24

2003-09-22 Priority claimed from GB0322159A external-priority patent/GB0322159D0/en

2004-02-12 Priority claimed from GB0403150A external-priority patent/GB0403150D0/en

2004-07-05 Priority claimed from GB0415110A external-priority patent/GB0415110D0/en

2004-09-22 Application filed by Pfizer filed Critical Pfizer

2005-03-24 Publication of NL1027084A1 publication Critical patent/NL1027084A1/nl

2006-01-24 Application granted granted Critical

2006-01-24 Publication of NL1027084C2 publication Critical patent/NL1027084C2/nl

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239000003336 oxytocin antagonist Substances 0.000 title description 5
229940121361 oxytocin antagonists Drugs 0.000 title description 5
229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 274
238000002360 preparation method Methods 0.000 claims description 274
-1 methoxy, ethoxy, 2-methoxyethoxy, dimethylamino, 1,2,3-triazol-2-yl Chemical group 0.000 claims description 188
238000000034 method Methods 0.000 claims description 107
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 34
230000001568 sexual effect Effects 0.000 claims description 31
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 23
101800000989 Oxytocin Proteins 0.000 claims description 22
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims description 22
229960001723 oxytocin Drugs 0.000 claims description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
238000011282 treatment Methods 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
229910052720 vanadium Inorganic materials 0.000 claims description 14
230000008602 contraction Effects 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
229910052727 yttrium Inorganic materials 0.000 claims description 13
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 12
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125000005842 heteroatom Chemical group 0.000 claims description 12
229910052721 tungsten Inorganic materials 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
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229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
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150000001204 N-oxides Chemical class 0.000 claims description 8
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MFRYLRNQOQUDDZ-UHFFFAOYSA-N 5-(2,3-dimethylphenyl)-2-[4-(6-methoxypyridin-3-yl)-5-(pyrrolidin-1-ylmethyl)-1,2,4-triazol-3-yl]pyridine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=CC=2)C=2C(=C(C)C=CC=2)C)=NN=C1CN1CCCC1 MFRYLRNQOQUDDZ-UHFFFAOYSA-N 0.000 claims description 7
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JTBHLQXMGZKKRH-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=CC(F)=CC=2)C)=NN=C1C JTBHLQXMGZKKRH-UHFFFAOYSA-N 0.000 claims description 5
UWVQTFRVRSCGAZ-UHFFFAOYSA-N 2-(5-fluoro-2-methoxyphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(C=N1)=CC=C1C1=CC(F)=CC=C1OC UWVQTFRVRSCGAZ-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
206010011953 Decreased activity Diseases 0.000 claims description 5
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125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
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125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
QHESCAMHVWJIJA-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=C(C)C=CC=2)C)=NN=C1C QHESCAMHVWJIJA-UHFFFAOYSA-N 0.000 claims description 4
YHKZSUNEWODEEO-UHFFFAOYSA-N 4-[5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazin-2-yl]-3-methylbenzonitrile Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=CC(=CC=2)C#N)C)=NN=C1C YHKZSUNEWODEEO-UHFFFAOYSA-N 0.000 claims description 4
AUIGHINKBLJVFJ-UHFFFAOYSA-N 4-[6-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-methylbenzonitrile Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CC=C1C1=CC=C(C#N)C=C1C AUIGHINKBLJVFJ-UHFFFAOYSA-N 0.000 claims description 4
WWCKNCVBSIWKGU-UHFFFAOYSA-N 5-(2,3-dimethylphenyl)-2-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CC=C1C1=CC=CC(C)=C1C WWCKNCVBSIWKGU-UHFFFAOYSA-N 0.000 claims description 4
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125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
PFIGDGJSZCKKLC-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyrazine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CN=C1C1=CC=CC(C)=C1C PFIGDGJSZCKKLC-UHFFFAOYSA-N 0.000 claims description 3
ZSIWQFWQNSLVMF-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(C=N1)=CC=C1C1=CC=CC(C)=C1C ZSIWQFWQNSLVMF-UHFFFAOYSA-N 0.000 claims description 3
WIGMUHOLXOUURZ-UHFFFAOYSA-N 2-(2-fluoro-5-methoxyphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound COC1=CC=C(F)C(C=2N=CC(=NC=2)C=2N(C(C)=NN=2)C=2C=NC(OC)=CC=2)=C1 WIGMUHOLXOUURZ-UHFFFAOYSA-N 0.000 claims description 3
HWPDYNZUAISOPP-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-1,2,4-triazol-3-yl]pyrazine Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CC(=NC=2)C=2C(=C(F)C=CC=2)OC)=NN=C1C HWPDYNZUAISOPP-UHFFFAOYSA-N 0.000 claims description 3
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YROLZLACGLYWCR-UHFFFAOYSA-N 4-[5-[5-(methoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyrazin-2-yl]-3-methylbenzonitrile Chemical compound C=1C=C(OC)N=CC=1N1C(COC)=NN=C1C(N=C1)=CN=C1C1=CC=C(C#N)C=C1C YROLZLACGLYWCR-UHFFFAOYSA-N 0.000 claims description 3
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102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Health & Medical Sciences (AREA)
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Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
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Cardiology (AREA)
Gynecology & Obstetrics (AREA)
Heart & Thoracic Surgery (AREA)
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Neurology (AREA)
Neurosurgery (AREA)
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Diabetes (AREA)
Urology & Nephrology (AREA)
Pregnancy & Childbirth (AREA)
Gastroenterology & Hepatology (AREA)
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Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NL1027084A 2003-09-22 2004-09-22 Gesubstitueerde triazoolderivaten als oxytocine-antagonisten. NL1027084C2 (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB0322159A GB0322159D0 (en)	2003-09-22	2003-09-22	New substituted triazoles for use as novel pharmaceuticals
GB0322159		2003-09-22
GB0403150		2004-02-12
GB0403150A GB0403150D0 (en)	2004-02-12	2004-02-12	Novel pharmaceuticals
GB0415110		2004-07-05
GB0415110A GB0415110D0 (en)	2004-07-05	2004-07-05	Substituted triazole derivatives as oxytocin antagonists

Publications (2)

Publication Number	Publication Date
NL1027084A1 NL1027084A1 (nl)	2005-03-24
NL1027084C2 true NL1027084C2 (nl)	2006-01-24

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ID=34381637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1027084A NL1027084C2 (nl)	2003-09-22	2004-09-22	Gesubstitueerde triazoolderivaten als oxytocine-antagonisten.

Country Status (12)

Country	Link
EP (1)	EP1673355A1 (pt)
JP (1)	JP2007505888A (pt)
AR (1)	AR045791A1 (pt)
BR (1)	BRPI0414663A (pt)
CA (1)	CA2539297C (pt)
MX (1)	MXPA06003158A (pt)
NL (1)	NL1027084C2 (pt)
PA (1)	PA8613001A1 (pt)
PE (1)	PE20050950A1 (pt)
TW (1)	TW200526606A (pt)
UY (1)	UY28524A1 (pt)
WO (1)	WO2005028452A1 (pt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7745630B2 (en)	2003-12-22	2010-06-29	Justin Stephen Bryans	Triazolyl piperidine arginine vasopressin receptor modulators
EP1817295B1 (en) *	2004-11-18	2012-11-07	Synta Pharmaceuticals Corp.	Triazole compounds that modulate hsp90 activity
AP2007004047A0 (en) *	2005-01-20	2007-06-30	Pfizer Ltd	Substituted triazole derivatives as oxtocin antagonists
EP1863795B1 (en) *	2005-03-21	2008-10-29	Pfizer Limited	Substituted triazole derivatives as oxytocin antagonists
US20080214622A1 (en) *	2005-03-21	2008-09-04	Alan Daniel Brown	Substituted Triazole Derivatives As Oxytocin Antagonists
KR101346902B1 (ko)	2005-07-09	2014-01-02	아스트라제네카 아베	당뇨병 치료에 있어 ｇｌｋ 활성화제로서 사용하기 위한헤테로아릴 벤즈아미드 유도체
JP2009504628A (ja) *	2005-08-10	2009-02-05	ファイザー・リミテッド	オキシトシン拮抗薬としての置換トリアゾール誘導体
FR2903985B1 (fr)	2006-07-24	2008-09-05	Sanofi Aventis Sa	Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique
FR2904316B1 (fr)	2006-07-31	2008-09-05	Sanofi Aventis Sa	Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique.
DE102006059710A1 (de) *	2006-12-18	2008-06-19	Freie Universität Berlin	Substituierte 4-Hydroxypyridine
FR2910473B1 (fr)	2006-12-26	2009-02-13	Sanofi Aventis Sa	Derives de n-(amino-heteroaryl)-1h-pyrrolopyridine-2- carboxamides, leur preparation et leur application en therapeutique.
US8536185B2 (en)	2008-09-22	2013-09-17	Cayman Chemical Company, Incorporated	Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases
EP3037101B1 (en)	2014-12-22	2019-03-06	Ferring B.V.	Oxytocin receptor antagonist therapy in the luteal phase for implantation and pregnancy in women undergoing assisted reproductive technologies
US10889569B2 (en)	2016-12-21	2021-01-12	Jiangsu Hengrui Medicine Co., Ltd.	Condensed ring group azacyclobutyl triazole derivative, preparation method therefor and use thereof in medicine
EP3564231A4 (en)	2016-12-28	2020-08-12	Jiangsu Hengrui Medicine Co., Ltd.	AZABICYCLO-SUBSTITUTE TRIAZOLE DERIVATIVE, METHOD OF PREPARATION AND APPLICATION IN MEDICINE
WO2019242642A1 (zh) *	2018-06-20	2019-12-26	江苏恒瑞医药股份有限公司	一种otr抑制剂的可药用盐、晶型及制备方法
CN113004250B (zh) *	2019-12-19	2022-07-26	上海森辉医药有限公司	一种制备取代的三唑衍生物的方法
JP2022042278A (ja) *	2020-09-02	2022-03-14	国立大学法人浜松医科大学	化合物又はその塩及び中枢オキシトシン受容体イメージング剤

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2000063363A (ja) *	1998-08-12	2000-02-29	Yamanouchi Pharmaceut Co Ltd	新規なトリアゾール誘導体
WO2001058880A1 (en) *	2000-02-08	2001-08-16	Yamanouchi Pharmaceutical Co., Ltd.	Novel triazole derivatives
SK16242002A3 (sk) *	2000-05-19	2003-04-01	Merck Patent Gmbh	Derivát triazolu a farmaceutický prostriedok, ktorý ho obsahuje
DE60204633T2 (de) *	2001-07-05	2006-06-14	Pfizer Prod Inc	Sulfonyl-Heteroaryl-Triazole als entzündungshemmende und analgetische Mittel
ES2249636T3 (es) *	2001-12-20	2006-04-01	Applied Research Systems Ars Holding N.V.	Triazoles como antagonistas de la oxitocina.

2004
- 2004-09-10 EP EP04769366A patent/EP1673355A1/en not_active Withdrawn
- 2004-09-10 CA CA2539297A patent/CA2539297C/en not_active Expired - Fee Related
- 2004-09-10 WO PCT/IB2004/002977 patent/WO2005028452A1/en not_active Ceased
- 2004-09-10 BR BRPI0414663-8A patent/BRPI0414663A/pt not_active IP Right Cessation
- 2004-09-10 JP JP2006526721A patent/JP2007505888A/ja active Pending
- 2004-09-10 MX MXPA06003158A patent/MXPA06003158A/es active IP Right Grant
- 2004-09-20 PE PE2004000912A patent/PE20050950A1/es not_active Application Discontinuation
- 2004-09-20 UY UY28524A patent/UY28524A1/es not_active Application Discontinuation
- 2004-09-21 AR ARP040103392A patent/AR045791A1/es unknown
- 2004-09-21 PA PA20048613001A patent/PA8613001A1/es unknown
- 2004-09-21 TW TW093128603A patent/TW200526606A/zh unknown
- 2004-09-22 NL NL1027084A patent/NL1027084C2/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
PA8613001A1 (es)	2005-08-04
TW200526606A (en)	2005-08-16
UY28524A1 (es)	2005-04-29
NL1027084A1 (nl)	2005-03-24
AR045791A1 (es)	2005-11-16
BRPI0414663A (pt)	2006-11-21
WO2005028452A1 (en)	2005-03-31
PE20050950A1 (es)	2005-11-11
EP1673355A1 (en)	2006-06-28
CA2539297A1 (en)	2005-03-31
MXPA06003158A (es)	2006-06-05
JP2007505888A (ja)	2007-03-15
WO2005028452A9 (en)	2005-07-21
CA2539297C (en)	2010-07-20

Legal Events

Date	Code	Title	Description
2005-06-01	AD1A	A request for search or an international type search has been filed
2005-12-01	RD2N	Patents in respect of which a decision has been taken or a report has been made (novelty report)	Effective date: 20050922
2006-04-03	PD2B	A search report has been drawn up
2009-06-02	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20090401

Publication	Publication Date	Title
NL1027084C2 (nl)	2006-01-24	Gesubstitueerde triazoolderivaten als oxytocine-antagonisten.
US10150752B2 (en)	2018-12-11	Substituted triazole derivatives as oxytocin antagonists
JP2007534740A (ja)	2007-11-29	バソプレッシンＶ１ａ受容体の阻害剤としての３−ヘテロシクリル−４−フェニル−トリアゾール誘導体
US20110092529A1 (en)	2011-04-21	1,2,4-Triazole Derivatives and Their Use as Oxytocin Antagonists
WO2005082866A2 (en)	2005-09-09	Substituted 1, 2, 4- triazole derivatives as oxytocin antagonists
US20080214622A1 (en)	2008-09-04	Substituted Triazole Derivatives As Oxytocin Antagonists
US20070185078A1 (en)	2007-08-09	Substituted triazole derivatives as oxytocin antagonists
US7875615B2 (en)	2011-01-25	Substituted triazole derivatives as oxytocin antagonists
US7449462B2 (en)	2008-11-11	Triazole derivatives which inhibit vasopressin antagonistic activity
US20100222365A1 (en)	2010-09-02	Substituted triazole deriviatives as oxytocin antagonists
US7618972B2 (en)	2009-11-17	Substituted triazole derivatives as oxytocin antagonists
HK1113927B (en)	2011-04-29	Substituted triazole derivatives as oxytocin antagonists