UA75145C2 - Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) - Google Patents
Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) Download PDFInfo
- Publication number
- UA75145C2 UA75145C2 UA20031211897A UA20031211897A UA75145C2 UA 75145 C2 UA75145 C2 UA 75145C2 UA 20031211897 A UA20031211897 A UA 20031211897A UA 20031211897 A UA20031211897 A UA 20031211897A UA 75145 C2 UA75145 C2 UA 75145C2
- Authority
- UA
- Ukraine
- Prior art keywords
- biphenyl
- ylcarbonyl
- oxadiazol
- methyloxime
- pyrrolidinone
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- NXDWUAQXIVWQRL-UHFFFAOYSA-N oxadiazole;pyrrolidine Chemical compound C1CCNC1.C1=CON=N1 NXDWUAQXIVWQRL-UHFFFAOYSA-N 0.000 title abstract description 9
- 150000004867 thiadiazoles Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 259
- 238000000034 method Methods 0.000 claims abstract description 116
- -1 preterm labor Chemical compound 0.000 claims abstract description 69
- 101800000989 Oxytocin Proteins 0.000 claims abstract description 38
- 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 abstract description 38
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims abstract description 38
- 229960001723 oxytocin Drugs 0.000 claims abstract description 38
- 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 abstract description 36
- 102000004279 Oxytocin receptors Human genes 0.000 claims abstract description 23
- 108090000876 Oxytocin receptors Proteins 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 208000005107 Premature Birth Diseases 0.000 claims abstract description 16
- 206010036590 Premature baby Diseases 0.000 claims abstract description 13
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 11
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 230000002265 prevention Effects 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims description 379
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 48
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 48
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 39
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
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- 108020003175 receptors Proteins 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 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
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 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
- 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
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005251 aryl acyl group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- JUOXYWXXPHUSAI-UHFFFAOYSA-N ethylamino acetate Chemical compound CCNOC(C)=O JUOXYWXXPHUSAI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005253 heteroarylacyl group Chemical group 0.000 claims description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 1
- NIXQLMVKRBUSPF-UHFFFAOYSA-N 3-(dimethylamino)propanamide Chemical compound CN(C)CCC(N)=O NIXQLMVKRBUSPF-UHFFFAOYSA-N 0.000 claims 1
- ZMDWVDOBEGZQJC-UHFFFAOYSA-N 3-piperidin-1-ylpropanamide Chemical compound NC(=O)CCN1CCCCC1 ZMDWVDOBEGZQJC-UHFFFAOYSA-N 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 15
- 208000006399 Premature Obstetric Labor Diseases 0.000 abstract description 12
- 239000005557 antagonist Substances 0.000 abstract description 8
- 230000006806 disease prevention Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 134
- 239000000243 solution Substances 0.000 description 110
- 239000000203 mixture Substances 0.000 description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
- 238000005481 NMR spectroscopy Methods 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
- 239000007858 starting material Substances 0.000 description 56
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- 238000006243 chemical reaction Methods 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 45
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- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- 239000002253 acid Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 21
- 229910000029 sodium carbonate Inorganic materials 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 229940125782 compound 2 Drugs 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 229910052700 potassium Inorganic materials 0.000 description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
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- 239000003480 eluent Substances 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
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Classifications
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- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01113632 | 2001-06-18 | ||
PCT/EP2002/006629 WO2002102799A2 (fr) | 2001-06-18 | 2002-06-14 | Derives de pyrrolidine oxadiazoles et thiadiazoles |
Publications (1)
Publication Number | Publication Date |
---|---|
UA75145C2 true UA75145C2 (en) | 2006-03-15 |
Family
ID=8177641
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA20031211897A UA75145C2 (en) | 2001-06-18 | 2002-06-14 | Pyrrolidine oxadiazole and thiadiazole derivatives, pharmaceutical composition based thereon, a method for producing thereof (variants) |
Country Status (27)
Country | Link |
---|---|
US (2) | US7115639B2 (fr) |
EP (1) | EP1444225B1 (fr) |
JP (1) | JP4426284B2 (fr) |
KR (1) | KR20040030678A (fr) |
CN (1) | CN100564378C (fr) |
AR (1) | AR036108A1 (fr) |
AU (1) | AU2002319237B2 (fr) |
BG (1) | BG108424A (fr) |
BR (1) | BR0211030A (fr) |
CA (1) | CA2449578C (fr) |
CZ (1) | CZ20033475A3 (fr) |
EA (1) | EA006212B1 (fr) |
EE (1) | EE200400022A (fr) |
ES (1) | ES2397305T3 (fr) |
HK (1) | HK1074204A1 (fr) |
HR (1) | HRP20031017A2 (fr) |
HU (1) | HUP0400238A2 (fr) |
IL (1) | IL159219A0 (fr) |
MX (1) | MXPA03011441A (fr) |
MY (1) | MY128890A (fr) |
NO (1) | NO20035399L (fr) |
PL (1) | PL367275A1 (fr) |
RS (1) | RS99503A (fr) |
SK (1) | SK15552003A3 (fr) |
UA (1) | UA75145C2 (fr) |
WO (1) | WO2002102799A2 (fr) |
ZA (1) | ZA200309402B (fr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1444225B1 (fr) | 2001-06-18 | 2012-10-10 | Merck Serono SA | Derives de pyrrolidine oxadiazoles et thiadiazoles utilisees en tant qu'antagonistes de l'oxytocine |
JP4773335B2 (ja) * | 2003-02-27 | 2011-09-14 | メルク セローノ ソシエテ アノニム | オキシトシンアンタゴニストとしてのピロリジン誘導体 |
DK1725526T3 (da) * | 2004-02-26 | 2008-03-03 | Serono Lab | Fremgangsmåde til fremstilling af pyrrolidinoximer |
KR101562549B1 (ko) | 2005-05-10 | 2015-10-23 | 인사이트 홀딩스 코포레이션 | 인돌아민 2,3-디옥시게나제의 조절제 및 이의 사용방법 |
CA2634198C (fr) | 2005-12-20 | 2014-06-03 | Incyte Corporation | N-hydroxyamidinoheterocycles en tant que modulateurs d'indoleamine 2,3-dioxygenase |
WO2008036642A2 (fr) * | 2006-09-19 | 2008-03-27 | Incyte Corporation | N-hydroxyamidinohétérocycles en tant que modulateurs d'indoléamine 2,3-dioxygénase |
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. |
EA029781B1 (ru) | 2008-07-08 | 2018-05-31 | Инсайт Корпорейшн | 1,2,5-оксадиазолы в качестве ингибиторов индоламин-2,3-диоксигеназы |
EP2845850A1 (fr) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Dérivés de pyrrolidine comme antagonistes des récepteurs V1a de vasopressine/oxytocine |
SI3066085T1 (sl) | 2013-11-08 | 2020-08-31 | Incyte Holdings Corporation | Postopek sinteze inhibitorja indolamina 2,3-dioksigenaze |
EP2886107A1 (fr) | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Formules orales de dérivés de pyrrolydine |
EA031353B1 (ru) | 2014-07-02 | 2018-12-28 | Обсева Са | Кристаллический о-метилоксим (3z,5s)-5-(гидроксиметил)-1-[(2'-метил-1,1'-бифенил-4-ил)карбонил]пирролидин-3-он, полезный в способах лечения состояний, связанных с активностью ot-r |
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 |
CA2210138A1 (fr) | 1995-01-24 | 1996-08-01 | Peter D. Williams | Antagonistes tocolytiques des recepteurs de l'oxytocine |
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 (fr) * | 1999-05-05 | 2006-03-08 | Merck & Co., Inc. | Prolines en tant qu'agents antimicrobiens |
EP1268418B1 (fr) * | 2000-03-27 | 2006-06-14 | Applied Research Systems ARS Holding N.V. | Derives de la pyrrolidine pharmaceutiquement actifs comme inhibiteurs de bax |
US7211601B2 (en) * | 2000-03-27 | 2007-05-01 | Applied Research Systems Ars Holding N.V. | Pharmaceutically active pyrrolidine derivatives |
WO2002032864A1 (fr) * | 2000-10-17 | 2002-04-25 | Applied Research Systems Ars Holding N.V. | Derives de sulfanilide actifs du point de vue pharmaceutique |
ES2303854T3 (es) * | 2001-03-20 | 2008-09-01 | Laboratoires Serono Sa | Derivados de ester de pirrolidina con actividad moduladora de oxitocina. |
EP1444225B1 (fr) | 2001-06-18 | 2012-10-10 | Merck Serono SA | Derives de pyrrolidine oxadiazoles et thiadiazoles utilisees en tant qu'antagonistes de l'oxytocine |
DE60207755T2 (de) * | 2001-12-20 | 2006-07-27 | Applied Research Systems Ars Holding N.V. | Triazole als oxytocin-antagonisten |
UA78058C2 (en) * | 2002-07-05 | 2007-02-15 | Applied Research Systems | Pyrrolidine derivative as oxitocin antagonists |
-
2002
- 2002-06-14 EP EP02748785A patent/EP1444225B1/fr not_active Expired - Lifetime
- 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 ES ES02748785T patent/ES2397305T3/es not_active Expired - Lifetime
- 2002-06-14 EA EA200400049A patent/EA006212B1/ru not_active IP Right Cessation
- 2002-06-14 AU AU2002319237A patent/AU2002319237B2/en not_active Ceased
- 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 BR BR0211030-0A patent/BR0211030A/pt not_active IP Right Cessation
- 2002-06-14 KR KR10-2003-7016485A patent/KR20040030678A/ko not_active Application Discontinuation
- 2002-06-14 UA UA20031211897A patent/UA75145C2/uk unknown
- 2002-06-14 JP JP2003506272A patent/JP4426284B2/ja not_active Expired - Fee Related
- 2002-06-14 CZ CZ20033475A patent/CZ20033475A3/cs unknown
- 2002-06-14 CA CA2449578A patent/CA2449578C/fr not_active Expired - Fee Related
- 2002-06-14 IL IL15921902A patent/IL159219A0/xx unknown
- 2002-06-14 WO PCT/EP2002/006629 patent/WO2002102799A2/fr not_active Application Discontinuation
- 2002-06-14 EE EEP200400022A patent/EE200400022A/xx unknown
- 2002-06-14 MX MXPA03011441A patent/MXPA03011441A/es active IP Right Grant
- 2002-06-14 PL PL02367275A patent/PL367275A1/xx not_active Application Discontinuation
- 2002-06-14 HU HU0400238A patent/HUP0400238A2/hu 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 HR HR20031017A patent/HRP20031017A2/xx not_active Application Discontinuation
- 2003-12-08 BG BG108424A patent/BG108424A/xx unknown
-
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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