CA2539297C - Substituted triazole derivatives as oxytocin antagonists - Google Patents
Substituted triazole derivatives as oxytocin antagonists Download PDFInfo
- Publication number
- CA2539297C CA2539297C CA2539297A CA2539297A CA2539297C CA 2539297 C CA2539297 C CA 2539297C CA 2539297 A CA2539297 A CA 2539297A CA 2539297 A CA2539297 A CA 2539297A CA 2539297 C CA2539297 C CA 2539297C
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- CA
- Canada
- Prior art keywords
- compound
- tautomer
- triazol
- methoxypyridin
- methyl
- Prior art date
- 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.)
- Expired - Fee Related
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- 239000003336 oxytocin antagonist Substances 0.000 title abstract description 9
- 229940121361 oxytocin antagonists Drugs 0.000 title abstract description 9
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 15
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 14
- 206010036596 premature ejaculation Diseases 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 327
- -1 chloro, methyl Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
- 239000012453 solvate Substances 0.000 claims description 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
- 230000001568 sexual effect Effects 0.000 claims description 29
- 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 26
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 101800000989 Oxytocin Proteins 0.000 claims description 21
- 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 21
- 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 21
- 229960001723 oxytocin Drugs 0.000 claims description 21
- 229910052720 vanadium Inorganic materials 0.000 claims description 21
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 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
- 229910052721 tungsten Inorganic materials 0.000 claims description 13
- 229910052727 yttrium Inorganic materials 0.000 claims description 13
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
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- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 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 4
- 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 4
- 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 4
- 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 4
- JSWNOVXSWSYLDJ-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenyl)-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=C(F)C=C1C JSWNOVXSWSYLDJ-UHFFFAOYSA-N 0.000 claims description 4
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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 4
- RCQOQEWBNAKEGY-UHFFFAOYSA-N 5-(4-fluoro-2-methylphenyl)-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=C(F)C=C1C RCQOQEWBNAKEGY-UHFFFAOYSA-N 0.000 claims description 4
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- 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 3
- 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 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- UAFXQKAEBVQYOV-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-5-[5-(2-methoxyethoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COCCOC)=NN=C1C(C=N1)=CC=C1C1=CC=CC(C)=C1C UAFXQKAEBVQYOV-UHFFFAOYSA-N 0.000 claims description 2
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- XYAMCELLHQCEOZ-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-5-[5-(2-methoxyethoxymethyl)-4-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]pyridine Chemical compound C=1C=C(OC)N=CC=1N1C(COCCOC)=NN=C1C(C=N1)=CC=C1C1=CC(F)=CC(F)=C1 XYAMCELLHQCEOZ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/12—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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Pregnancy & Childbirth (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0322159A GB0322159D0 (en) | 2003-09-22 | 2003-09-22 | New substituted triazoles for use as novel pharmaceuticals |
| GB0322159.5 | 2003-09-22 | ||
| GB0403150.6 | 2004-02-12 | ||
| GB0403150A GB0403150D0 (en) | 2004-02-12 | 2004-02-12 | Novel pharmaceuticals |
| GB0415110.6 | 2004-07-05 | ||
| GB0415110A GB0415110D0 (en) | 2004-07-05 | 2004-07-05 | Substituted triazole derivatives as oxytocin antagonists |
| PCT/IB2004/002977 WO2005028452A1 (en) | 2003-09-22 | 2004-09-10 | Substituted triazole derivatives as oxytocin antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2539297A1 CA2539297A1 (en) | 2005-03-31 |
| CA2539297C true CA2539297C (en) | 2010-07-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2539297A Expired - Fee Related CA2539297C (en) | 2003-09-22 | 2004-09-10 | Substituted triazole derivatives as oxytocin antagonists |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1673355A1 (enExample) |
| JP (1) | JP2007505888A (enExample) |
| AR (1) | AR045791A1 (enExample) |
| BR (1) | BRPI0414663A (enExample) |
| CA (1) | CA2539297C (enExample) |
| MX (1) | MXPA06003158A (enExample) |
| NL (1) | NL1027084C2 (enExample) |
| PA (1) | PA8613001A1 (enExample) |
| PE (1) | PE20050950A1 (enExample) |
| TW (1) | TW200526606A (enExample) |
| UY (1) | UY28524A1 (enExample) |
| WO (1) | WO2005028452A1 (enExample) |
Families Citing this family (18)
| 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 |
| ES2594874T3 (es) * | 2004-11-18 | 2016-12-23 | Synta Pharmaceuticals Corp. | Compuestos de triazol que modulan la actividad de HSP90 |
| AP2007004047A0 (en) | 2005-01-20 | 2007-06-30 | Pfizer Ltd | Substituted triazole derivatives as oxtocin antagonists |
| WO2006100557A1 (en) * | 2005-03-21 | 2006-09-28 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| WO2006100588A1 (en) * | 2005-03-21 | 2006-09-28 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| EP2305674A1 (en) | 2005-07-09 | 2011-04-06 | AstraZeneca AB | Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes |
| WO2007017752A1 (en) * | 2005-08-10 | 2007-02-15 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| 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. |
| NZ592297A (en) | 2008-09-22 | 2012-11-30 | Cayman Chemical Co Inc | 2-Aryl-5-heteroaryl pyridine and pyrimidine derivatives as pharmaceutical active agents |
| ES2716862T3 (es) | 2014-12-22 | 2019-06-17 | Ferring Bv | Terapia con antagonistas del receptor de oxitocina en la fase lútea para la implantación y embarazo en mujeres que se someten a tecnologías de reproducción asistida |
| JP2020502211A (ja) | 2016-12-21 | 2020-01-23 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 縮合環基を有するアザシクロブチルトリアゾール誘導体、その製造方法および医薬におけるその使用 |
| TW201823231A (zh) | 2016-12-28 | 2018-07-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 氮雜雙環基取代的三唑類衍生物、其製備方法及其在醫藥上的應用 |
| 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)
| 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 |
| WO2001087855A1 (en) * | 2000-05-19 | 2001-11-22 | Yamanouchi Pharmaceutical Co., Ltd. | Triazole derivatives |
| ATE297913T1 (de) * | 2001-07-05 | 2005-07-15 | Pfizer Prod Inc | Sulfonyl-heteroaryl-triazole als entzündungshemmende und analgetische mittel |
| DK1458381T3 (da) * | 2001-12-20 | 2006-03-20 | Applied Research Systems | Triazoler som oxytocinantagonister |
-
2004
- 2004-09-10 MX MXPA06003158A patent/MXPA06003158A/es active IP Right Grant
- 2004-09-10 CA CA2539297A patent/CA2539297C/en not_active Expired - Fee Related
- 2004-09-10 EP EP04769366A patent/EP1673355A1/en not_active Withdrawn
- 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
- 2004-09-20 PE PE2004000912A patent/PE20050950A1/es not_active Application Discontinuation
- 2004-09-20 UY UY28524A patent/UY28524A1/es not_active Application Discontinuation
- 2004-09-21 TW TW093128603A patent/TW200526606A/zh unknown
- 2004-09-21 AR ARP040103392A patent/AR045791A1/es unknown
- 2004-09-21 PA PA20048613001A patent/PA8613001A1/es unknown
- 2004-09-22 NL NL1027084A patent/NL1027084C2/nl not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| UY28524A1 (es) | 2005-04-29 |
| EP1673355A1 (en) | 2006-06-28 |
| NL1027084C2 (nl) | 2006-01-24 |
| PE20050950A1 (es) | 2005-11-11 |
| JP2007505888A (ja) | 2007-03-15 |
| WO2005028452A1 (en) | 2005-03-31 |
| BRPI0414663A (pt) | 2006-11-21 |
| TW200526606A (en) | 2005-08-16 |
| NL1027084A1 (nl) | 2005-03-24 |
| PA8613001A1 (es) | 2005-08-04 |
| MXPA06003158A (es) | 2006-06-05 |
| AR045791A1 (es) | 2005-11-16 |
| WO2005028452A9 (en) | 2005-07-21 |
| CA2539297A1 (en) | 2005-03-31 |
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| EEER | Examination request | ||
| MKLA | Lapsed |