ZA200206799B - Pharmaceutically active pyrrolidine derivatives. - Google Patents
Pharmaceutically active pyrrolidine derivatives. Download PDFInfo
- Publication number
- ZA200206799B ZA200206799B ZA200206799A ZA200206799A ZA200206799B ZA 200206799 B ZA200206799 B ZA 200206799B ZA 200206799 A ZA200206799 A ZA 200206799A ZA 200206799 A ZA200206799 A ZA 200206799A ZA 200206799 B ZA200206799 B ZA 200206799B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrrolidinecarboxamide
- methoxyimino
- biphenyl
- hydroxy
- carbonyl
- Prior art date
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- 150000003235 pyrrolidines Chemical class 0.000 title description 6
- -1 hydroxy, mercapto Chemical class 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 101800000989 Oxytocin Proteins 0.000 claims description 25
- 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 25
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 25
- 229960001723 oxytocin Drugs 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 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 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 102000004279 Oxytocin receptors Human genes 0.000 claims description 12
- 108090000876 Oxytocin receptors Proteins 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 7
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010036600 Premature labour Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000026440 premature labor Diseases 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 102000005962 receptors Human genes 0.000 claims description 5
- 108020003175 receptors Proteins 0.000 claims description 5
- 208000005107 Premature Birth Diseases 0.000 claims description 4
- 206010036590 Premature baby Diseases 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 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 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 76
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 76
- 239000004305 biphenyl Substances 0.000 claims 43
- 235000010290 biphenyl Nutrition 0.000 claims 39
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims 23
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 11
- 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 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- QMCCLVXCIVLBNN-QFIPXVFZSA-N (2S)-1-(2,2-diphenylacetyl)-4-methoxyimino-N-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1SC=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 QMCCLVXCIVLBNN-QFIPXVFZSA-N 0.000 claims 1
- QUNFVGWIGJQUQB-SKCDSABHSA-N (2S)-1-(4-benzoylbenzoyl)-N-(2-hydroxy-2-phenylethyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 QUNFVGWIGJQUQB-SKCDSABHSA-N 0.000 claims 1
- RHYYTDRYAYVCRS-NRFANRHFSA-N (2S)-4-(chloromethylidene)-N-[(3,4-dimethoxyphenyl)methyl]-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NCC=2C=C(OC)C(OC)=CC=2)CC(=CCl)C1 RHYYTDRYAYVCRS-NRFANRHFSA-N 0.000 claims 1
- PCWNGXKLPJXYBV-VWLOTQADSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-1-[4-(dimethylamino)butanoyl]-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound CN(C)CCCC(=O)N([C@@H](C1)C(=O)NC=2C=C3C=CC=NC3=CC=2)CC1=NOCC1=CC=C(Cl)C(Cl)=C1 PCWNGXKLPJXYBV-VWLOTQADSA-N 0.000 claims 1
- JEERIKYDXKKSMC-LJAQVGFWSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-N-[2-(diethylamino)ethyl]-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCCN(CC)CC)C(=NOCC=2C=C(Cl)C(Cl)=CC=2)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 JEERIKYDXKKSMC-LJAQVGFWSA-N 0.000 claims 1
- VKGSGSSHMIOOIV-ZDUSSCGKSA-N (2S)-4-methoxyimino-1-(3-oxobutanoyl)-N-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound CC(=O)CC(=O)N1CC(=NOC)C[C@H]1C(=O)NCC1=CC=CS1 VKGSGSSHMIOOIV-ZDUSSCGKSA-N 0.000 claims 1
- OBECWEZHIKUBKA-SANMLTNESA-N (2S)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]-N-(2-phenylethyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C OBECWEZHIKUBKA-SANMLTNESA-N 0.000 claims 1
- LPGOHZHKQUUHKJ-ANYOKISRSA-N (2S)-N-(2,3-dihydroxypropyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCC(O)CO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 LPGOHZHKQUUHKJ-ANYOKISRSA-N 0.000 claims 1
- ONFXYAGQOSYQNP-SFHVURJKSA-N (2S)-N-(2-amino-2-oxoethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCC(N)=O)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 ONFXYAGQOSYQNP-SFHVURJKSA-N 0.000 claims 1
- IHVYLODBADSGMC-VWLOTQADSA-N (2S)-N-(2-anilinoethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCNC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 IHVYLODBADSGMC-VWLOTQADSA-N 0.000 claims 1
- HRLJULKFMHSCIS-VWLOTQADSA-N (2S)-N-(2-anilinoethyl)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCNC=1C=CC=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 HRLJULKFMHSCIS-VWLOTQADSA-N 0.000 claims 1
- BFEQEXFXHHGWGJ-XLTVJXRZSA-N (2S)-N-(2-hydroxy-2-naphthalen-2-ylethyl)-4-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=C2C=CC=CC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1OC BFEQEXFXHHGWGJ-XLTVJXRZSA-N 0.000 claims 1
- IBXGJPAYWMFXSF-PMCHYTPCSA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C IBXGJPAYWMFXSF-PMCHYTPCSA-N 0.000 claims 1
- ODZMUKAUQUQRQC-NASUQTAISA-N (2S)-N-(2-hydroxy-3-phenoxypropyl)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)COC=1C=CC=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ODZMUKAUQUQRQC-NASUQTAISA-N 0.000 claims 1
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- XGFPVJRVRSBXJN-IBGZPJMESA-N (2S)-N-(3-amino-3-oxopropyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCC(N)=O)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 XGFPVJRVRSBXJN-IBGZPJMESA-N 0.000 claims 1
- DEANAXAKRAFIOX-FQEVSTJZSA-N (2S)-N-(3-hydroxypropyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCCO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 DEANAXAKRAFIOX-FQEVSTJZSA-N 0.000 claims 1
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- CUSSSJCUURTDOI-JRFVFWCSSA-N (2S)-N-[(1R,2S)-2-(hydroxymethyl)cyclohexyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@H]1[C@H](CCCC1)CO)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 CUSSSJCUURTDOI-JRFVFWCSSA-N 0.000 claims 1
- AIAHGYFWJNRBHB-VXNXHJTFSA-N (2S)-N-[(1R,2S)-2-carbamoylcyclohexyl]-1-[4-(2,6-dimethylphenyl)benzoyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@H]1[C@H](CCCC1)C(N)=O)C(=O)C(C=C1)=CC=C1C1=C(C)C=CC=C1C AIAHGYFWJNRBHB-VXNXHJTFSA-N 0.000 claims 1
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Applications Claiming Priority (1)
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| ZA200206799B true ZA200206799B (en) | 2003-08-26 |
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| ZA200206799A ZA200206799B (en) | 2000-03-27 | 2002-08-26 | Pharmaceutically active pyrrolidine derivatives. |
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| NZ (1) | NZ521060A (et) |
| PL (1) | PL358001A1 (et) |
| PT (1) | PT1268419E (et) |
| SI (1) | SI1268419T1 (et) |
| SK (1) | SK13832002A3 (et) |
| UA (1) | UA74362C2 (et) |
| WO (1) | WO2001072705A1 (et) |
| YU (1) | YU73502A (et) |
| ZA (1) | ZA200206799B (et) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL151911A0 (en) * | 2000-03-27 | 2003-04-10 | Applied Research Systems | Pyrolidine derivatives, their preparation and pharmaceutical compositions containing them |
| IL159219A0 (en) * | 2001-06-18 | 2004-06-01 | Applied Research Systems | Pyrrolidine oxadiazole derivatives, their preparation and pharmaceutical compositions containing them |
| AR034897A1 (es) | 2001-08-07 | 2004-03-24 | Hoffmann La Roche | Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos |
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| US7405234B2 (en) | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| UA78058C2 (en) * | 2002-07-05 | 2007-02-15 | Applied Research Systems | Pyrrolidine derivative as oxitocin antagonists |
| EP1567487A4 (en) * | 2002-11-15 | 2005-11-16 | Bristol Myers Squibb Co | OPEN-CHAINED, PROLYL-FROSTED MODULATORS OF ANDROGEN RECEPTOR FUNCTION |
| WO2004076407A2 (en) * | 2003-02-27 | 2004-09-10 | Applied Research Systems Ars Holding N.V. | Pyrrolidine derivatives as oxytocin antagonists |
| US7820702B2 (en) | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
| SI1725526T1 (sl) * | 2004-02-26 | 2008-04-30 | Serono Lab | Postopek priprave pirolidoin-oksimov |
| US7625923B2 (en) | 2004-03-04 | 2009-12-01 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7696241B2 (en) | 2004-03-04 | 2010-04-13 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| EP2379524A1 (en) * | 2008-12-18 | 2011-10-26 | Boehringer Ingelheim International GmbH | Serotonin 5-ht2b receptor inhibitors |
| EP2759533B1 (en) | 2011-09-22 | 2017-08-02 | Takeda Pharmaceutical Company Limited | Condensed heterocyclic compound |
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| MX371068B (es) | 2014-07-02 | 2020-01-15 | ObsEva SA | ((3z,5s)-5-(hidroximetil)-1-[(2'-metil-1,1'-bifenil-4-il)carbonil ]pirrolidin-3-ona o-metiloxima cristalina y métodos de uso de la misma. |
| CN117044622A (zh) * | 2023-09-22 | 2023-11-14 | 贵州师范大学 | 一种无花瓣芥菜型油菜的选育方式 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL33548A (en) | 1964-08-05 | 1972-04-27 | Upjohn Co | Galactopyranosides which are intermediates for lincomycin |
| US3555007A (en) | 1968-07-22 | 1971-01-12 | Upjohn Co | 7-deoxy-7-halo lincomycin d derivatives |
| US3674647A (en) | 1970-10-07 | 1972-07-04 | Upjohn Co | Preparation of lincomycin analogues |
| US4596819A (en) * | 1984-01-23 | 1986-06-24 | Warner-Lambert Company | Modified tripeptides |
| GB9316162D0 (en) | 1993-08-04 | 1993-09-22 | Zeneca Ltd | Fungicides |
| 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 |
| AR016133A1 (es) * | 1997-07-31 | 2001-06-20 | Wyeth Corp | Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria |
| US6329418B1 (en) * | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| WO2000004005A1 (fr) * | 1998-07-14 | 2000-01-27 | Ono Pharmaceutical Co., Ltd. | Derives acides amines et medicaments dont ces derives sont les principes actifs |
| JP4511042B2 (ja) * | 1998-08-07 | 2010-07-28 | メルク セローノ ソシエテ アノニム | 不妊症の治療のためのｆｓｈ模倣物 |
| EE200100391A (et) * | 1999-01-27 | 2002-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Peptidüül-heterotsüklilised ketoonid, nende kasutamine ja farmatseutiline kompositsioon |
| AU759022B2 (en) * | 1999-02-18 | 2003-04-03 | Kaken Pharmaceutical Co., Ltd. | Novel amide derivatives as growth hormone secretagogues |
| DK1178958T3 (da) * | 1999-03-15 | 2004-06-21 | Axys Pharm Inc | N-cyanomethylamider som proteaseinhibitorer |
| JP2002543129A (ja) * | 1999-05-05 | 2002-12-17 | メルク エンド カムパニー インコーポレーテッド | 抗微生物剤としての新規なプロリン類 |
| GB0000079D0 (en) * | 2000-01-05 | 2000-02-23 | Ferring Bv | Novel antidiuretic agents |
| IL151911A0 (en) * | 2000-03-27 | 2003-04-10 | Applied Research Systems | Pyrolidine derivatives, their preparation and pharmaceutical compositions containing them |
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- 2001-03-20 DE DE60120940T patent/DE60120940T2/de not_active Expired - Lifetime
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- 2001-03-20 MX MXPA02009382A patent/MXPA02009382A/es active IP Right Grant
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- 2001-03-20 CA CA002401242A patent/CA2401242A1/en not_active Abandoned
- 2001-03-20 CN CNB018071767A patent/CN1296354C/zh not_active Expired - Fee Related
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- 2001-03-20 CZ CZ20023243A patent/CZ20023243A3/cs unknown
- 2001-03-20 DK DK01929439T patent/DK1268419T3/da active
- 2001-03-20 ES ES01929439T patent/ES2261404T3/es not_active Expired - Lifetime
- 2001-03-20 SK SK1383-2002A patent/SK13832002A3/sk unknown
- 2001-03-20 AT AT01929439T patent/ATE330940T1/de not_active IP Right Cessation
- 2001-03-20 EP EP01929439A patent/EP1268419B1/en not_active Expired - Lifetime
- 2001-03-20 JP JP2001570618A patent/JP2003528854A/ja not_active Withdrawn
- 2001-03-20 WO PCT/EP2001/003171 patent/WO2001072705A1/en not_active Application Discontinuation
- 2001-03-20 NZ NZ521060A patent/NZ521060A/en unknown
- 2001-03-20 AU AU5620901A patent/AU5620901A/xx active Pending
- 2001-03-20 KR KR1020027012744A patent/KR100714585B1/ko not_active IP Right Cessation
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2002
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- 2002-09-23 BG BG107132A patent/BG107132A/bg unknown
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2003
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