ZA200309402B - Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. - Google Patents
Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. Download PDFInfo
- Publication number
- ZA200309402B ZA200309402B ZA200309402A ZA200309402A ZA200309402B ZA 200309402 B ZA200309402 B ZA 200309402B ZA 200309402 A ZA200309402 A ZA 200309402A ZA 200309402 A ZA200309402 A ZA 200309402A ZA 200309402 B ZA200309402 B ZA 200309402B
- Authority
- ZA
- South Africa
- Prior art keywords
- biphenyl
- ylcarbonyl
- methyloxime
- oxadiazol
- pyrrolidinone
- Prior art date
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- -1 Pyrrolidine oxadiazole- and thiadiazole oxime Chemical class 0.000 title claims description 71
- 229940122828 Oxytocin receptor antagonist Drugs 0.000 title 1
- 239000004305 biphenyl Substances 0.000 claims description 85
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
- 235000010290 biphenyl Nutrition 0.000 claims description 32
- 101800000989 Oxytocin Proteins 0.000 claims description 26
- 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 26
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- NXDWUAQXIVWQRL-UHFFFAOYSA-N oxadiazole;pyrrolidine Chemical class C1CCNC1.C1=CON=N1 NXDWUAQXIVWQRL-UHFFFAOYSA-N 0.000 claims description 26
- 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 26
- 229960001723 oxytocin Drugs 0.000 claims description 26
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 13
- FWSFUZVSSAWOCA-UHFFFAOYSA-N n-methoxy-3,4-dihydro-2h-pyrrol-5-amine Chemical compound CON=C1CCCN1 FWSFUZVSSAWOCA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 102000004279 Oxytocin receptors Human genes 0.000 claims description 11
- 108090000876 Oxytocin receptors Proteins 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 102000005962 receptors Human genes 0.000 claims description 9
- 108020003175 receptors Proteins 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 7
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 7
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 7
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 6
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- 206010036590 Premature baby Diseases 0.000 claims description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
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- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005251 aryl acyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 2
- ZCYVMCAHYDRHRY-DEOSSOPVSA-N 1-[4-[[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]methyl]piperazin-1-yl]ethanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CN2CCN(CC2)C(C)=O)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZCYVMCAHYDRHRY-DEOSSOPVSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- 241000630665 Hada Species 0.000 claims 1
- KRIVWZIPRHSVHX-IBGZPJMESA-N [(2s)-2-[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CCO)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KRIVWZIPRHSVHX-IBGZPJMESA-N 0.000 claims 1
- VKAVWUGMFLJAHN-IBGZPJMESA-N [(2s)-2-[5-(2-hydroxyethyl)-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CCO)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 VKAVWUGMFLJAHN-IBGZPJMESA-N 0.000 claims 1
- UGIYMJOAGGMXOQ-IBGZPJMESA-N [4-(2-chloro-4-fluorophenyl)phenyl]-[(2s)-2-[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CCO)N=1)C(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1Cl UGIYMJOAGGMXOQ-IBGZPJMESA-N 0.000 claims 1
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- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000009984 peri-natal effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- 150000003858 primary carboxamides Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- QLNJFJADRCOGBJ-LBPDFUHNSA-N propanamide Chemical compound CC[13C](N)=O QLNJFJADRCOGBJ-LBPDFUHNSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- UXUYQXXOPCMNLU-UHFFFAOYSA-N pyrrolidine;thiadiazole Chemical class C1CCNC1.C1=CSN=N1 UXUYQXXOPCMNLU-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- KJFDNYXPZQIAKH-NOZRDPDXSA-N tert-butyl (3r)-3-[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)[C@H]1CN(CCC1)C(=O)OC(C)(C)C)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KJFDNYXPZQIAKH-NOZRDPDXSA-N 0.000 description 1
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01113632 | 2001-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200309402B true ZA200309402B (en) | 2004-12-03 |
Family
ID=8177641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200309402A ZA200309402B (en) | 2001-06-18 | 2003-12-03 | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US7115639B2 (uk) |
| EP (1) | EP1444225B1 (uk) |
| JP (1) | JP4426284B2 (uk) |
| KR (1) | KR20040030678A (uk) |
| CN (1) | CN100564378C (uk) |
| AR (1) | AR036108A1 (uk) |
| AU (1) | AU2002319237B2 (uk) |
| BG (1) | BG108424A (uk) |
| BR (1) | BR0211030A (uk) |
| CA (1) | CA2449578C (uk) |
| CZ (1) | CZ20033475A3 (uk) |
| EA (1) | EA006212B1 (uk) |
| EE (1) | EE200400022A (uk) |
| ES (1) | ES2397305T3 (uk) |
| HK (1) | HK1074204A1 (uk) |
| HR (1) | HRP20031017A2 (uk) |
| HU (1) | HUP0400238A2 (uk) |
| IL (1) | IL159219A0 (uk) |
| MX (1) | MXPA03011441A (uk) |
| MY (1) | MY128890A (uk) |
| NO (1) | NO20035399L (uk) |
| PL (1) | PL367275A1 (uk) |
| RS (1) | RS99503A (uk) |
| SK (1) | SK15552003A3 (uk) |
| UA (1) | UA75145C2 (uk) |
| WO (1) | WO2002102799A2 (uk) |
| ZA (1) | ZA200309402B (uk) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ20033475A3 (en) | 2001-06-18 | 2004-05-12 | Appliedáresearchásystemsáarsáholdingán@V | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| EP1597229B1 (en) | 2003-02-27 | 2009-11-18 | Merck Serono SA | Pyrrolidine derivatives as oxytocin antagonists |
| EP1725526B1 (en) * | 2004-02-26 | 2007-12-12 | Laboratoires Serono SA | Method for preparing pyrrolidine oximes |
| ES2401482T3 (es) | 2005-05-10 | 2013-04-22 | Incyte Corporation | Moduladores de la indolamina 2,3-dioxigenasa y métodos de uso de los mismos |
| EP1971583B1 (en) | 2005-12-20 | 2015-03-25 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (es) | 2006-09-19 | 2008-02-08 | Incyte Corp | Compuestos derivados de heterociclo n-hidroxiamino; composicion farmaceutica, util para tratar cancer, infecciones virales y desordenes neurodegenerativos entre otras. |
| ES2444574T3 (es) * | 2006-09-19 | 2014-02-25 | Incyte Corporation | N-hidroxiamidinoheterociclos como moduladores de la indolamina 2,3-dioxigenasa |
| RS53688B9 (sr) | 2008-07-08 | 2020-01-31 | Incyte Holdings Corp | 1,2,5-oksadiazoli kao inhibitori indoleamin 2,3-dioksigenaze |
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| US9321755B2 (en) | 2013-11-08 | 2016-04-26 | Incyte Corporation | Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor |
| EP2886107A1 (en) | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| EP3164384B1 (en) | 2014-07-02 | 2019-12-04 | ObsEva S.A. | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime useful in methods of treating conditions related to the ot-r activity |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2722190B1 (fr) * | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
| EP0805681A4 (en) | 1995-01-24 | 1998-05-06 | Merck & Co Inc | TOCOLYTIC ANTAGONISTS OF OXYTOCIN RECEPTORS |
| US5756497A (en) | 1996-03-01 | 1998-05-26 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| EP1176959B1 (en) | 1999-05-05 | 2006-03-08 | Merck & Co., Inc. | Novel prolines as antimicrobial agents |
| SI1268418T1 (sl) * | 2000-03-27 | 2006-10-31 | Applied Research Systems | Farmacevtsko aktivni pirolidinski derivati kot bax-inhibitorji |
| UA74362C2 (uk) * | 2000-03-27 | 2005-12-15 | Еплайд Рісьорч Системз Ерс Холдінг Н.В. | Фармацевтично активні похідні піролідину |
| AU1401902A (en) * | 2000-10-17 | 2002-04-29 | Applied Research Systems | Pharmaceutically active sulfanilide derivatives |
| ATE394371T1 (de) * | 2001-03-20 | 2008-05-15 | Serono Lab | Pyrrolidinesterderivate mit oxytocinmodulierender wirkung |
| CZ20033475A3 (en) | 2001-06-18 | 2004-05-12 | Appliedáresearchásystemsáarsáholdingán@V | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| EP1458381B1 (en) * | 2001-12-20 | 2005-11-30 | Applied Research Systems ARS Holding N.V. | Triazoles as oxytocin antagonists |
| UA78058C2 (en) * | 2002-07-05 | 2007-02-15 | Applied Research Systems | Pyrrolidine derivative as oxitocin antagonists |
-
2002
- 2002-06-14 CZ CZ20033475A patent/CZ20033475A3/cs unknown
- 2002-06-14 RS YU99503A patent/RS99503A/sr unknown
- 2002-06-14 US US10/480,992 patent/US7115639B2/en not_active Expired - Fee Related
- 2002-06-14 JP JP2003506272A patent/JP4426284B2/ja not_active Expired - Fee Related
- 2002-06-14 KR KR10-2003-7016485A patent/KR20040030678A/ko not_active Application Discontinuation
- 2002-06-14 ES ES02748785T patent/ES2397305T3/es not_active Expired - Lifetime
- 2002-06-14 PL PL02367275A patent/PL367275A1/xx not_active Application Discontinuation
- 2002-06-14 EP EP02748785A patent/EP1444225B1/en not_active Expired - Lifetime
- 2002-06-14 EA EA200400049A patent/EA006212B1/ru not_active IP Right Cessation
- 2002-06-14 CA CA2449578A patent/CA2449578C/en not_active Expired - Fee Related
- 2002-06-14 MX MXPA03011441A patent/MXPA03011441A/es active IP Right Grant
- 2002-06-14 BR BR0211030-0A patent/BR0211030A/pt not_active IP Right Cessation
- 2002-06-14 WO PCT/EP2002/006629 patent/WO2002102799A2/en not_active Application Discontinuation
- 2002-06-14 CN CNB028159446A patent/CN100564378C/zh not_active Expired - Fee Related
- 2002-06-14 SK SK1555-2003A patent/SK15552003A3/sk not_active Application Discontinuation
- 2002-06-14 IL IL15921902A patent/IL159219A0/xx unknown
- 2002-06-14 HU HU0400238A patent/HUP0400238A2/hu unknown
- 2002-06-14 UA UA20031211897A patent/UA75145C2/uk unknown
- 2002-06-14 AU AU2002319237A patent/AU2002319237B2/en not_active Ceased
- 2002-06-14 EE EEP200400022A patent/EE200400022A/xx unknown
- 2002-06-18 MY MYPI20022260A patent/MY128890A/en unknown
- 2002-06-21 AR ARP020102353A patent/AR036108A1/es unknown
-
2003
- 2003-12-03 ZA ZA200309402A patent/ZA200309402B/en unknown
- 2003-12-04 NO NO20035399A patent/NO20035399L/no unknown
- 2003-12-08 BG BG108424A patent/BG108424A/xx unknown
- 2003-12-08 HR HR20031017A patent/HRP20031017A2/xx not_active Application Discontinuation
-
2005
- 2005-09-16 HK HK05108106.9A patent/HK1074204A1/xx not_active IP Right Cessation
-
2006
- 2006-06-09 US US11/449,802 patent/US20060229343A1/en not_active Abandoned
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