SK13832002A3 - Pyrolidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Pyrolidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK13832002A3
Authority: SK; Slovakia
Prior art keywords: pyrrolidinecarboxamide; methoxyimino; biphenyl; carbonyl; hydroxy
Prior art date: 2000-03-27

Application number

SK1383-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Serge Halazy

Anna Quattropani

Alexander Scheer

Matthias Schwarz

Russel Thomas

Anthony Baxter

Original Assignee

Applied Research Systems Ars Holding N. V.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-03-27

Filing date

2001-03-20

Publication date

2003-03-04

2001-03-20 Application filed by Applied Research Systems Ars Holding N. V. filed Critical Applied Research Systems Ars Holding N. V.

2003-03-04 Publication of SK13832002A3 publication Critical patent/SK13832002A3/sk

Links

150000003235 pyrrolidines Chemical class 0.000 title claims abstract description 57
239000003112 inhibitor Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 550
-1 premature labor Chemical compound 0.000 claims abstract description 515
238000000034 method Methods 0.000 claims abstract description 500
238000002360 preparation method Methods 0.000 claims abstract description 67
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 51
125000003118 aryl group Chemical group 0.000 claims abstract description 41
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 25
229960001723 oxytocin Drugs 0.000 claims abstract description 25
101800000989 Oxytocin Proteins 0.000 claims abstract description 24
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 24
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims abstract description 24
102000004279 Oxytocin receptors Human genes 0.000 claims abstract description 22
108090000876 Oxytocin receptors Proteins 0.000 claims abstract description 22
238000011282 treatment Methods 0.000 claims abstract description 18
208000006399 Premature Obstetric Labor Diseases 0.000 claims abstract description 17
208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 14
206010036600 Premature labour Diseases 0.000 claims abstract description 14
208000026440 premature labor Diseases 0.000 claims abstract description 14
229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
230000001404 mediated effect Effects 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
230000002265 prevention Effects 0.000 claims abstract description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 188
239000004305 biphenyl Substances 0.000 claims description 135
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 79
125000001841 imino group Chemical group [H]N=* 0.000 claims description 75
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
235000010290 biphenyl Nutrition 0.000 claims description 40
ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical compound CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 32
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 27
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
229920006395 saturated elastomer Polymers 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
230000008569 process Effects 0.000 claims description 18
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
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 description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
UTMYYLVADKNKHS-UHFFFAOYSA-N CON=C1CCNC1C(N)=O Chemical compound CON=C1CCNC1C(N)=O UTMYYLVADKNKHS-UHFFFAOYSA-N 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
125000003107 substituted aryl group Chemical group 0.000 claims description 12
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
230000027455 binding Effects 0.000 claims description 10
239000007822 coupling agent Substances 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
238000005897 peptide coupling reaction Methods 0.000 claims description 10
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 9
125000005309 thioalkoxy group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
102000005962 receptors Human genes 0.000 claims description 8
108020003175 receptors Proteins 0.000 claims description 8
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 description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 6
230000003042 antagnostic effect Effects 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
LLTLYZAEWLUNPU-IBGZPJMESA-N (2s)-n-(2-hydroxyethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 LLTLYZAEWLUNPU-IBGZPJMESA-N 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
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
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
HADXULRQRGBKGE-SANMLTNESA-N (2S)-4-methoxyimino-1-(4-phenylbenzoyl)-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC=1C=C2C=CC=NC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 HADXULRQRGBKGE-SANMLTNESA-N 0.000 claims description 4
MANHLYREAYIEJU-QFIPXVFZSA-N (2S)-N-(2,1,3-benzothiadiazol-4-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC=1C2=NSN=C2C=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MANHLYREAYIEJU-QFIPXVFZSA-N 0.000 claims description 4
XIDWXIFKVPDMSG-FQEVSTJZSA-N (2S)-N-(2-methoxyethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound COCCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 XIDWXIFKVPDMSG-FQEVSTJZSA-N 0.000 claims description 4
MLMDRTCOOJIVBB-SKCDSABHSA-N (2s)-n-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-(4-phenylbenzoyl)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=C1 MLMDRTCOOJIVBB-SKCDSABHSA-N 0.000 claims description 4
125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 4
125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 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
150000003857 carboxamides Chemical class 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
FZTXOCKBUUSPBK-LJAQVGFWSA-N (2S)-1-(2,2-diphenylacetyl)-4-[(4-methoxyphenyl)methoxyimino]-N-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CON=C1CN(C(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)[C@H](C(=O)NCC=2SC=CC=2)C1 FZTXOCKBUUSPBK-LJAQVGFWSA-N 0.000 claims description 3
ROYLDTQXKBDKRH-MHZLTWQESA-N (2S)-1-(4-cyanobenzoyl)-4-[(3,4-dichlorophenyl)methoxyimino]-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CON=C1CN(C(=O)C=2C=CC(=CC=2)C#N)[C@H](C(=O)NC=2C=C3C=CC=NC3=CC=2)C1 ROYLDTQXKBDKRH-MHZLTWQESA-N 0.000 claims description 3
RRVOWCLKRNJCPL-SANMLTNESA-N (2S)-4-(chloromethylidene)-1-(4-phenylbenzoyl)-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NC=1C=C2C=CC=NC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RRVOWCLKRNJCPL-SANMLTNESA-N 0.000 claims description 3
QBUYLWOBNZZGJW-FQEVSTJZSA-N (2S)-4-(chloromethylidene)-N-(2-methoxyethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound COCCNC(=O)[C@@H]1CC(=CCl)CN1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 QBUYLWOBNZZGJW-FQEVSTJZSA-N 0.000 claims description 3
GEAOOMNUVSTJAS-QFIPXVFZSA-N (2S)-4-(chloromethylidene)-N-(furan-2-ylmethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NCC=1OC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GEAOOMNUVSTJAS-QFIPXVFZSA-N 0.000 claims description 3
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 description 3
GJARWOXPMIVMAS-QFIPXVFZSA-N (2S)-4-(cyanomethylidene)-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(=CC#N)C1 GJARWOXPMIVMAS-QFIPXVFZSA-N 0.000 claims description 3
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 description 3
HDGANIMJTQRQLA-LJAQVGFWSA-N (2S)-4-benzylidene-N-[2-(diethylamino)ethyl]-1-(2,2-diphenylacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCCN(CC)CC)C(=CC=2C=CC=CC=2)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 HDGANIMJTQRQLA-LJAQVGFWSA-N 0.000 claims description 3
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 description 3
RZAUTCKGFSGBFU-QHCPKHFHSA-N (2S)-4-methoxyimino-N-(naphthalen-1-ylmethyl)-1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C2=CC=CC=C2C=CC=1)C(=O)COC1=CC=CC=C1 RZAUTCKGFSGBFU-QHCPKHFHSA-N 0.000 claims description 3
PRZAUXKSVVMGHD-IBGZPJMESA-N (2S)-4-methoxyimino-N-(naphthalen-1-ylmethyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxamide Chemical compound CC(=O)CC(=O)N1CC(=NOC)C[C@H]1C(=O)NCC1=CC=CC2=CC=CC=C12 PRZAUXKSVVMGHD-IBGZPJMESA-N 0.000 claims description 3
OGEOEUIVZVOGHU-QHCPKHFHSA-N (2S)-N-(1,3-benzodioxol-5-ylmethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C=C2OCOC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OGEOEUIVZVOGHU-QHCPKHFHSA-N 0.000 claims description 3
WHVVULWWIGBFTH-QFIPXVFZSA-N (2S)-N-(2,1,3-benzothiadiazol-4-yl)-1-(2,2-diphenylacetyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC=1C2=NSN=C2C=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 WHVVULWWIGBFTH-QFIPXVFZSA-N 0.000 claims description 3
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 description 3
AZYBUEPYNZBXOY-DEOSSOPVSA-N (2S)-N-(2-anilinoethyl)-4-methoxyimino-1-(4-pyridin-2-ylbenzoyl)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=N1 AZYBUEPYNZBXOY-DEOSSOPVSA-N 0.000 claims description 3
COVNFXDYELILDR-DEOSSOPVSA-N (2S)-N-(2-anilinoethyl)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)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=CN=C1 COVNFXDYELILDR-DEOSSOPVSA-N 0.000 claims description 3
KKECGIOIEZVARE-DEOSSOPVSA-N (2S)-N-(2-anilinoethyl)-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)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=NC=C1 KKECGIOIEZVARE-DEOSSOPVSA-N 0.000 claims description 3
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 description 3
IBMUSXSBECWIRX-LJAQVGFWSA-N (2S)-N-(naphthalen-1-ylmethyl)-1-(2-phenoxyacetyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC=1C=CC=CC=1)C(=O)NCC=1C2=CC=CC=C2C=CC=1)C(=O)COC1=CC=CC=C1 IBMUSXSBECWIRX-LJAQVGFWSA-N 0.000 claims description 3
OHIUDCXQBIKLRY-QHCPKHFHSA-N (2S)-N-[(1-hydroxycyclohexyl)methyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC1(O)CCCCC1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OHIUDCXQBIKLRY-QHCPKHFHSA-N 0.000 claims description 3
FDDHELBWNLMABK-UIOOFZCWSA-N (2S)-N-[(1R)-2-hydroxy-1-phenylethyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@@H](CO)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C FDDHELBWNLMABK-UIOOFZCWSA-N 0.000 claims description 3
JRPIBZDLVDDCCG-ZTCOLXNVSA-N (2S)-N-[(1R,2R)-2-(hydroxymethyl)cyclohexyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@H]1[C@@H](CCCC1)CO)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 JRPIBZDLVDDCCG-ZTCOLXNVSA-N 0.000 claims description 3
ATPGDENZRBBJIZ-GSDHBNRESA-N (2S)-N-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@@H](CO)[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ATPGDENZRBBJIZ-GSDHBNRESA-N 0.000 claims description 3
CHTUEMGLMPLXGT-GSDHBNRESA-N (2S)-N-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N[C@@H](CO)[C@@H](O)C=1C=CC=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 CHTUEMGLMPLXGT-GSDHBNRESA-N 0.000 claims description 3
CPFIDJYLGSIOIX-VABKMULXSA-N (2S)-N-[(1S,2S)-2-hydroxycyclohexyl]-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)O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 CPFIDJYLGSIOIX-VABKMULXSA-N 0.000 claims description 3
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RVXXYBNSDGMHHM-BJKOFHAPSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 RVXXYBNSDGMHHM-BJKOFHAPSA-N 0.000 claims description 3
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HHDFBJZTIBOOEC-DEOSSOPVSA-N (2S)-N-[(3,4-dimethoxyphenyl)methyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C=C(OC)C(OC)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 HHDFBJZTIBOOEC-DEOSSOPVSA-N 0.000 claims description 3
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YYSGGCIQDQMGFO-QHCPKHFHSA-N [(2s)-2-(1h-benzimidazol-2-yl)-4-methylidenepyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=C)C=1NC2=CC=CC=C2N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 YYSGGCIQDQMGFO-QHCPKHFHSA-N 0.000 claims description 3
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Classifications

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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/02—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 containing two hetero rings
- C07D405/06—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 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/02—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 containing two hetero rings
- C07D405/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/14—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 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/02—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 containing two hetero rings
- C07D417/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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SK1383-2002A 2000-03-27 2001-03-20 Pyrolidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie SK13832002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00106034		2000-03-27
PCT/EP2001/003171 WO2001072705A1 (en)	2000-03-27	2001-03-20	Pharmaceutically active pyrrolidine derivatives as bax inhibitors

Publications (1)

Publication Number	Publication Date
SK13832002A3 true SK13832002A3 (sk)	2003-03-04

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ID=8168169

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1383-2002A SK13832002A3 (sk)	2000-03-27	2001-03-20	Pyrolidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (33)

Country	Link
US (2)	US7211601B2 (pl)
EP (1)	EP1268419B1 (pl)
JP (2)	JP2003528854A (pl)
KR (1)	KR100714585B1 (pl)
CN (1)	CN1296354C (pl)
AR (1)	AR029499A1 (pl)
AT (1)	ATE330940T1 (pl)
AU (2)	AU5620901A (pl)
BG (1)	BG107132A (pl)
BR (1)	BR0109900A (pl)
CA (1)	CA2401242A1 (pl)
CY (1)	CY1105519T1 (pl)
CZ (1)	CZ20023243A3 (pl)
DE (1)	DE60120940T2 (pl)
DK (1)	DK1268419T3 (pl)
EA (1)	EA006424B1 (pl)
EE (1)	EE200200555A (pl)
ES (1)	ES2261404T3 (pl)
HK (1)	HK1054031B (pl)
HR (1)	HRP20020705A2 (pl)
HU (1)	HUP0300994A2 (pl)
IL (1)	IL151912A0 (pl)
MX (1)	MXPA02009382A (pl)
NO (1)	NO323969B1 (pl)
NZ (1)	NZ521060A (pl)
PL (1)	PL358001A1 (pl)
PT (1)	PT1268419E (pl)
SI (1)	SI1268419T1 (pl)
SK (1)	SK13832002A3 (pl)
UA (1)	UA74362C2 (pl)
WO (1)	WO2001072705A1 (pl)
YU (1)	YU73502A (pl)
ZA (1)	ZA200206799B (pl)

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US7820702B2 (en)	2004-02-04	2010-10-26	Bristol-Myers Squibb Company	Sulfonylpyrrolidine modulators of androgen receptor function and method
EA011026B1 (ru) *	2004-02-26	2008-12-30	Лаборатуар Сероно Са	Способ получения пирролидиноксимов
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
US9120776B2 (en)	2011-09-22	2015-09-01	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
EP3753921A1 (en)	2014-07-02	2020-12-23	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
TW202435864A (zh)	2023-02-09	2024-09-16	大陸商上海葆正醫藥科技有限公司	亞胺化合物及其製備方法和應用
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

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2001
- 2001-03-20 ES ES01929439T patent/ES2261404T3/es not_active Expired - Lifetime
- 2001-03-20 HU HU0300994A patent/HUP0300994A2/hu unknown
- 2001-03-20 DK DK01929439T patent/DK1268419T3/da active
- 2001-03-20 PT PT01929439T patent/PT1268419E/pt unknown
- 2001-03-20 UA UA2002097675A patent/UA74362C2/uk unknown
- 2001-03-20 WO PCT/EP2001/003171 patent/WO2001072705A1/en not_active Ceased
- 2001-03-20 CN CNB018071767A patent/CN1296354C/zh not_active Expired - Fee Related
- 2001-03-20 HK HK03106333.0A patent/HK1054031B/zh not_active IP Right Cessation
- 2001-03-20 US US10/239,912 patent/US7211601B2/en not_active Expired - Fee Related
- 2001-03-20 HR HRP20020705 patent/HRP20020705A2/hr not_active Application Discontinuation
- 2001-03-20 NZ NZ521060A patent/NZ521060A/en unknown
- 2001-03-20 JP JP2001570618A patent/JP2003528854A/ja not_active Withdrawn
- 2001-03-20 SI SI200130566T patent/SI1268419T1/sl unknown
- 2001-03-20 MX MXPA02009382A patent/MXPA02009382A/es active IP Right Grant
- 2001-03-20 SK SK1383-2002A patent/SK13832002A3/sk unknown
- 2001-03-20 DE DE60120940T patent/DE60120940T2/de not_active Expired - Lifetime
- 2001-03-20 KR KR1020027012744A patent/KR100714585B1/ko not_active Expired - Fee Related
- 2001-03-20 AU AU5620901A patent/AU5620901A/xx active Pending
- 2001-03-20 IL IL15191201A patent/IL151912A0/xx unknown
- 2001-03-20 PL PL01358001A patent/PL358001A1/pl not_active Application Discontinuation
- 2001-03-20 AU AU2001256209A patent/AU2001256209B2/en not_active Ceased
- 2001-03-20 BR BR0109900-0A patent/BR0109900A/pt not_active IP Right Cessation
- 2001-03-20 YU YU73502A patent/YU73502A/sh unknown
- 2001-03-20 EE EEP200200555A patent/EE200200555A/xx unknown
- 2001-03-20 EA EA200201026A patent/EA006424B1/ru unknown
- 2001-03-20 CZ CZ20023243A patent/CZ20023243A3/cs unknown
- 2001-03-20 EP EP01929439A patent/EP1268419B1/en not_active Expired - Lifetime
- 2001-03-20 AT AT01929439T patent/ATE330940T1/de not_active IP Right Cessation
- 2001-03-20 CA CA002401242A patent/CA2401242A1/en not_active Abandoned
- 2001-03-26 AR ARP010101425A patent/AR029499A1/es not_active Application Discontinuation
2002
- 2002-08-26 ZA ZA200206799A patent/ZA200206799B/en unknown
- 2002-09-23 BG BG107132A patent/BG107132A/bg unknown
- 2002-09-25 NO NO20024598A patent/NO323969B1/no unknown
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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- 2012-05-09 JP JP2012107898A patent/JP5580364B2/ja not_active Expired - Fee Related

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Publication number	Publication date
DE60120940T2 (de)	2007-01-25
EE200200555A (et)	2004-06-15
EA200201026A1 (ru)	2003-02-27
KR100714585B1 (ko)	2007-05-07
MXPA02009382A (es)	2003-01-28
EP1268419B1 (en)	2006-06-21
CA2401242A1 (en)	2001-10-04
JP2003528854A (ja)	2003-09-30
DK1268419T3 (da)	2006-10-02
DE60120940D1 (de)	2006-08-03
US7211601B2 (en)	2007-05-01
AR029499A1 (es)	2003-07-02
PT1268419E (pt)	2006-08-31
HK1054031A1 (en)	2003-11-14
CZ20023243A3 (cs)	2003-01-15
IL151912A0 (en)	2003-04-10
JP5580364B2 (ja)	2014-08-27
JP2012149098A (ja)	2012-08-09
HK1054031B (zh)	2007-05-04
ATE330940T1 (de)	2006-07-15
WO2001072705A1 (en)	2001-10-04
KR20020095195A (ko)	2002-12-20
BR0109900A (pt)	2003-06-03
YU73502A (sh)	2005-11-28
HRP20020705A2 (en)	2004-12-31
AU5620901A (en)	2001-10-08
NO323969B1 (no)	2007-07-23
NO20024598L (no)	2002-11-25
EP1268419A1 (en)	2003-01-02
US20080167318A1 (en)	2008-07-10
UA74362C2 (uk)	2005-12-15
PL358001A1 (pl)	2004-08-09
CN1419541A (zh)	2003-05-21
AU2001256209B2 (en)	2006-02-16
EA006424B1 (ru)	2005-12-29
ZA200206799B (en)	2003-08-26
CY1105519T1 (el)	2010-07-28
HUP0300994A2 (hu)	2003-08-28
SI1268419T1 (sl)	2006-10-31
BG107132A (bg)	2003-04-30
US20030212012A1 (en)	2003-11-13
NZ521060A (en)	2004-05-28
ES2261404T3 (es)	2006-11-16
NO20024598D0 (no)	2002-09-25
CN1296354C (zh)	2007-01-24

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