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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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| EP00106034 | 2000-03-27 |
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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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| Country | Link |
|---|---|
| US (2) | US7211601B2 (pt) |
| EP (1) | EP1268419B1 (pt) |
| JP (2) | JP2003528854A (pt) |
| KR (1) | KR100714585B1 (pt) |
| CN (1) | CN1296354C (pt) |
| AR (1) | AR029499A1 (pt) |
| AT (1) | ATE330940T1 (pt) |
| AU (2) | AU5620901A (pt) |
| BG (1) | BG107132A (pt) |
| BR (1) | BR0109900A (pt) |
| CA (1) | CA2401242A1 (pt) |
| CY (1) | CY1105519T1 (pt) |
| CZ (1) | CZ20023243A3 (pt) |
| DE (1) | DE60120940T2 (pt) |
| DK (1) | DK1268419T3 (pt) |
| EA (1) | EA006424B1 (pt) |
| EE (1) | EE200200555A (pt) |
| ES (1) | ES2261404T3 (pt) |
| HK (1) | HK1054031B (pt) |
| HR (1) | HRP20020705A2 (pt) |
| HU (1) | HUP0300994A2 (pt) |
| IL (1) | IL151912A0 (pt) |
| MX (1) | MXPA02009382A (pt) |
| NO (1) | NO323969B1 (pt) |
| NZ (1) | NZ521060A (pt) |
| PL (1) | PL358001A1 (pt) |
| PT (1) | PT1268419E (pt) |
| SI (1) | SI1268419T1 (pt) |
| SK (1) | SK13832002A3 (pt) |
| UA (1) | UA74362C2 (pt) |
| WO (1) | WO2001072705A1 (pt) |
| YU (1) | YU73502A (pt) |
| ZA (1) | ZA200206799B (pt) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1268418T1 (sl) * | 2000-03-27 | 2006-10-31 | Applied Research Systems | Farmacevtsko aktivni pirolidinski derivati kot bax-inhibitorji |
| CZ20033475A3 (en) * | 2001-06-18 | 2004-05-12 | Appliedáresearchásystemsáarsáholdingán@V | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| 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 |
| US7632858B2 (en) * | 2002-11-15 | 2009-12-15 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| EP1597229B1 (en) | 2003-02-27 | 2009-11-18 | Merck Serono SA | 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 |
| EP1725526B1 (en) * | 2004-02-26 | 2007-12-12 | Laboratoires Serono SA | Method for preparing pyrrolidine oximes |
| 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 |
| WO2010080357A1 (en) * | 2008-12-18 | 2010-07-15 | 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 |
| 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 |
| CN114621962B (zh) * | 2022-03-21 | 2024-05-14 | 广西大学 | 花生AhBI-1基因VIGS沉默体系 |
| WO2024165071A1 (zh) * | 2023-02-09 | 2024-08-15 | 上海葆正医药科技有限公司 | 亚胺化合物及其制备方法和应用 |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL23907A (en) | 1964-08-05 | 1971-05-26 | Upjohn Co | Lincomycin analogues and a process for their production |
| 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 |
| EP1097929A4 (en) * | 1998-07-14 | 2005-12-21 | Ono Pharmaceutical Co | AMINO ACID DERIVATIVES AND MEDICAMENTS IN WHICH THESE DERIVATIVES ARE THE ACTIVE INGREDIENTS |
| IL141063A (en) * | 1998-08-07 | 2005-06-19 | Applied Research Systems | Derivatives of pyrrolidine-2-carboxylic acid and piperidine-2-carboxylic acids and pharmaceutical compositions comprising said derivatives for treating infertility |
| SK10742001A3 (sk) * | 1999-01-27 | 2002-08-06 | Ortho-Mcneil Pharmaceutical, Inc. | Peptidylové heterocyklické ketóny použiteľné ako inhibítory tryptázy |
| CN1157224C (zh) * | 1999-02-18 | 2004-07-14 | 科研制药株式会社 | 用作生长激素促分泌剂的新酰胺衍生物 |
| IL145430A0 (en) * | 1999-03-15 | 2002-06-30 | Axys Pharm Inc | N-cyanomethyl amides, processes for the preparation thereof and pharmaceutical compositions containing the same |
| EP1176959B1 (en) * | 1999-05-05 | 2006-03-08 | Merck & Co., Inc. | Novel prolines as antimicrobial agents |
| GB0000079D0 (en) * | 2000-01-05 | 2000-02-23 | Ferring Bv | Novel antidiuretic agents |
| SI1268418T1 (sl) * | 2000-03-27 | 2006-10-31 | Applied Research Systems | Farmacevtsko aktivni pirolidinski derivati kot bax-inhibitorji |
-
2001
- 2001-03-20 UA UA2002097675A patent/UA74362C2/uk unknown
- 2001-03-20 HU HU0300994A patent/HUP0300994A2/hu unknown
- 2001-03-20 SI SI200130566T patent/SI1268419T1/sl unknown
- 2001-03-20 KR KR1020027012744A patent/KR100714585B1/ko not_active IP Right Cessation
- 2001-03-20 NZ NZ521060A patent/NZ521060A/en unknown
- 2001-03-20 DE DE60120940T patent/DE60120940T2/de not_active Expired - Lifetime
- 2001-03-20 EE EEP200200555A patent/EE200200555A/xx unknown
- 2001-03-20 SK SK1383-2002A patent/SK13832002A3/sk unknown
- 2001-03-20 US US10/239,912 patent/US7211601B2/en not_active Expired - Fee Related
- 2001-03-20 WO PCT/EP2001/003171 patent/WO2001072705A1/en not_active Application Discontinuation
- 2001-03-20 AU AU5620901A patent/AU5620901A/xx active Pending
- 2001-03-20 JP JP2001570618A patent/JP2003528854A/ja not_active Withdrawn
- 2001-03-20 EA EA200201026A patent/EA006424B1/ru unknown
- 2001-03-20 AU AU2001256209A patent/AU2001256209B2/en not_active Ceased
- 2001-03-20 PL PL01358001A patent/PL358001A1/xx not_active Application Discontinuation
- 2001-03-20 ES ES01929439T patent/ES2261404T3/es not_active Expired - Lifetime
- 2001-03-20 CA CA002401242A patent/CA2401242A1/en not_active Abandoned
- 2001-03-20 BR BR0109900-0A patent/BR0109900A/pt not_active IP Right Cessation
- 2001-03-20 IL IL15191201A patent/IL151912A0/xx unknown
- 2001-03-20 AT AT01929439T patent/ATE330940T1/de not_active IP Right Cessation
- 2001-03-20 DK DK01929439T patent/DK1268419T3/da active
- 2001-03-20 YU YU73502A patent/YU73502A/sh unknown
- 2001-03-20 CZ CZ20023243A patent/CZ20023243A3/cs unknown
- 2001-03-20 PT PT01929439T patent/PT1268419E/pt unknown
- 2001-03-20 CN CNB018071767A patent/CN1296354C/zh not_active Expired - Fee Related
- 2001-03-20 MX MXPA02009382A patent/MXPA02009382A/es active IP Right Grant
- 2001-03-20 EP EP01929439A patent/EP1268419B1/en not_active Expired - Lifetime
- 2001-03-26 AR ARP010101425A patent/AR029499A1/es not_active Application Discontinuation
-
2002
- 2002-08-26 ZA ZA200206799A patent/ZA200206799B/en unknown
- 2002-08-28 HR HRP20020705 patent/HRP20020705A2/hr not_active Application Discontinuation
- 2002-09-23 BG BG107132A patent/BG107132A/bg unknown
- 2002-09-25 NO NO20024598A patent/NO323969B1/no unknown
-
2003
- 2003-09-05 HK HK03106333.0A patent/HK1054031B/zh not_active IP Right Cessation
-
2006
- 2006-07-28 CY CY20061101060T patent/CY1105519T1/el unknown
-
2007
- 2007-04-09 US US11/783,341 patent/US20080167318A1/en not_active Abandoned
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2012
- 2012-05-09 JP JP2012107898A patent/JP5580364B2/ja not_active Expired - Fee Related
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