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 PDFInfo
- Publication number
- SK13832002A3 SK13832002A3 SK1383-2002A SK13832002A SK13832002A3 SK 13832002 A3 SK13832002 A3 SK 13832002A3 SK 13832002 A SK13832002 A SK 13832002A SK 13832002 A3 SK13832002 A3 SK 13832002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- pyrrolidinecarboxamide
- methoxyimino
- biphenyl
- carbonyl
- hydroxy
- Prior art date
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
- NZAANOFONGEKMX-DQEYMECFSA-N (2S)-N-[(2R)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC[C@H](O)C=1C=CC=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 NZAANOFONGEKMX-DQEYMECFSA-N 0.000 claims description 3
- SIISTOSOAGENHP-BJKOFHAPSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-pyridin-2-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=CC=N1 SIISTOSOAGENHP-BJKOFHAPSA-N 0.000 claims description 3
- 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
- UINONIOMTOPUCM-BJKOFHAPSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-pyridin-4-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=NC=C1 UINONIOMTOPUCM-BJKOFHAPSA-N 0.000 claims description 3
- 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
- BMTXORUAJGVLCT-HKBQPEDESA-N (2S)-N-benzyl-1-(2,2-diphenylacetyl)-4-[(4-methoxyphenyl)methoxyimino]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=2C=CC=CC=2)C1 BMTXORUAJGVLCT-HKBQPEDESA-N 0.000 claims description 3
- QMFNIKCCMRPRCF-VWLOTQADSA-N (2S)-N-benzyl-1-(2,2-diphenylacetyl)-4-ethoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC)C(=O)NCC=1C=CC=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 QMFNIKCCMRPRCF-VWLOTQADSA-N 0.000 claims description 3
- NIXWYJQVHUCOIO-DEOSSOPVSA-N (2S)-N-benzyl-1-(2,2-diphenylacetyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C=CC=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 NIXWYJQVHUCOIO-DEOSSOPVSA-N 0.000 claims description 3
- KKZVQMIXHGZZGV-KRWDZBQOSA-N (2S)-N-cyclopropyl-4-[(3,4-dichlorophenyl)methoxyimino]-1-(3-oxobutanoyl)pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)CC(=O)C)=NOCC=1C=C(Cl)C(Cl)=CC=1)NC1CC1 KKZVQMIXHGZZGV-KRWDZBQOSA-N 0.000 claims description 3
- GRMHPNANLFOBAN-SANMLTNESA-N (2s)-4-methylidene-1-(4-phenylbenzoyl)-n-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=C)C(=O)NC=1C=C2C=CC=NC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GRMHPNANLFOBAN-SANMLTNESA-N 0.000 claims description 3
- CYPUELVXQAORFO-NRFANRHFSA-N (2s)-n-(3-hydroxypropyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCCO)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 CYPUELVXQAORFO-NRFANRHFSA-N 0.000 claims description 3
- UHKCJPBWXIGXIL-IBGZPJMESA-N (2s)-n-(furan-2-ylmethyl)-4-methylidene-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NCC=2OC=CC=2)CC(=C)C1 UHKCJPBWXIGXIL-IBGZPJMESA-N 0.000 claims description 3
- ULZCNPAMNXLAFJ-QFIPXVFZSA-N (2s)-n-(furan-2-ylmethyl)-4-methylidene-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=C)C(=O)NCC=1OC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ULZCNPAMNXLAFJ-QFIPXVFZSA-N 0.000 claims description 3
- ZAXLCZWBAWDNPZ-SANMLTNESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(C1=CC=C(C=C1)C=1C=NC=CC=1)=O ZAXLCZWBAWDNPZ-SANMLTNESA-N 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
- PPBMVZJOBAGISL-DEOSSOPVSA-N 2-[4-[(2S)-2-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-4-methoxyiminopyrrolidine-1-carbonyl]phenyl]benzonitrile Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N1CCN(CCO)CC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C#N PPBMVZJOBAGISL-DEOSSOPVSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- BFRUZKHRRFWGJT-RRPUWOKSSA-N O[C@@H]1CC[C@H](CC1)NC(=O)[C@H]1N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)OC Chemical compound O[C@@H]1CC[C@H](CC1)NC(=O)[C@H]1N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)OC BFRUZKHRRFWGJT-RRPUWOKSSA-N 0.000 claims description 3
- 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
- OXGGVPAXYUXIIN-QHCPKHFHSA-N (2S)-1-(2,2-diphenylacetyl)-4-ethoxyimino-N-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC)C(=O)NCC=1SC=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 OXGGVPAXYUXIIN-QHCPKHFHSA-N 0.000 claims description 2
- 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 description 2
- DLSSSJJOCVWFHE-LOSJGSFVSA-N (2S)-4-(chloromethylidene)-N-[(2S)-2-hydroxy-2-phenylethyl]-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC[C@@H](O)C=2C=CC=CC=2)C(=CCl)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DLSSSJJOCVWFHE-LOSJGSFVSA-N 0.000 claims description 2
- VQBAYXBAHVYLSM-FQEVSTJZSA-N (2S)-4-methoxyimino-N,N-dimethyl-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)N(C)C)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 VQBAYXBAHVYLSM-FQEVSTJZSA-N 0.000 claims description 2
- ACEHRKFWLWNRHT-IBGZPJMESA-N (2S)-4-methoxyimino-N-methyl-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound CNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 ACEHRKFWLWNRHT-IBGZPJMESA-N 0.000 claims description 2
- ZZYUULYGCJERAG-FQEVSTJZSA-N (2S)-N-(1,3-dihydroxypropan-2-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NC(CO)CO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 ZZYUULYGCJERAG-FQEVSTJZSA-N 0.000 claims description 2
- RIIIAZBMLPOXHR-QFIPXVFZSA-N (2S)-N-(1,3-dihydroxypropan-2-yl)-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NC(CO)CO)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1C RIIIAZBMLPOXHR-QFIPXVFZSA-N 0.000 claims description 2
- SSOPUEMIOHRNOB-QHCPKHFHSA-N (2S)-N-(2,1,3-benzothiadiazol-4-yl)-4-(cyanomethylidene)-1-(2,2-diphenylacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(NC=2C3=NSN=C3C=CC=2)=O)C(=CC#N)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 SSOPUEMIOHRNOB-QHCPKHFHSA-N 0.000 claims description 2
- 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 description 2
- SSAYUODWILWTGG-UXMRNZNESA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-(2-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1OC1=CC=CC=C1 SSAYUODWILWTGG-UXMRNZNESA-N 0.000 claims description 2
- JHGWDCHZOYWRIM-SKCDSABHSA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-(3-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 JHGWDCHZOYWRIM-SKCDSABHSA-N 0.000 claims description 2
- QLDUJAZJZNHNJZ-SKCDSABHSA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-(3-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=1)=CC=CC=1C1=CC=CC=C1 QLDUJAZJZNHNJZ-SKCDSABHSA-N 0.000 claims description 2
- SPAZBDHTZSSFON-FQEVSTJZSA-N (2S)-N-(2-hydroxyethyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCO)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 SPAZBDHTZSSFON-FQEVSTJZSA-N 0.000 claims description 2
- LNHQULPQGICQEZ-NRFANRHFSA-N (2S)-N-(2-hydroxyethyl)-4-methoxyimino-N-methyl-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)N(C)CCO)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 LNHQULPQGICQEZ-NRFANRHFSA-N 0.000 claims description 2
- PZODJMQTMYTHKH-FQEVSTJZSA-N (2S)-N-(3-amino-3-oxopropyl)-1-[4-(2,6-dimethylphenyl)benzoyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCC(N)=O)N1C(=O)C1=CC=C(C=2C(=CC=CC=2C)C)C=C1 PZODJMQTMYTHKH-FQEVSTJZSA-N 0.000 claims description 2
- SKYWIFYUQDJKCR-FQEVSTJZSA-N (2S)-N-(3-hydroxypropyl)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCCO)N1S(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 SKYWIFYUQDJKCR-FQEVSTJZSA-N 0.000 claims description 2
- TWHNUPUEYATMAV-NRFANRHFSA-N (2S)-N-(4-hydroxybutyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCCCCO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 TWHNUPUEYATMAV-NRFANRHFSA-N 0.000 claims description 2
- KNSJHMQVMVOGCT-IBGZPJMESA-N (2S)-N-(furan-2-ylmethyl)-4-methoxyimino-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NCC=2OC=CC=2)CC(=NOC)C1 KNSJHMQVMVOGCT-IBGZPJMESA-N 0.000 claims description 2
- LENBGPWMSPRMCV-QFIPXVFZSA-N (2S)-N-(furan-2-ylmethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1OC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LENBGPWMSPRMCV-QFIPXVFZSA-N 0.000 claims description 2
- DGCINFPIPJZUHE-ZRBLBEILSA-N (2S)-N-[(1R,2S)-2-carbamoylcyclohexyl]-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)C(N)=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DGCINFPIPJZUHE-ZRBLBEILSA-N 0.000 claims description 2
- BVRAGJVUGWUNBX-DNRDEDMTSA-N (2S)-N-[(1S,2S,3R,4R)-3-carbamoyl-2-bicyclo[2.2.1]hept-5-enyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@H]1[C@H]([C@@H]2C=C[C@H]1C2)NC(=O)[C@H]1N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C BVRAGJVUGWUNBX-DNRDEDMTSA-N 0.000 claims description 2
- SIISTOSOAGENHP-ZEQRLZLVSA-N (2S)-N-[(2R)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-pyridin-2-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=CC=N1 SIISTOSOAGENHP-ZEQRLZLVSA-N 0.000 claims description 2
- RVXXYBNSDGMHHM-ZEQRLZLVSA-N (2S)-N-[(2R)-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-ZEQRLZLVSA-N 0.000 claims description 2
- UINONIOMTOPUCM-ZEQRLZLVSA-N (2S)-N-[(2R)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-pyridin-4-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=NC=C1 UINONIOMTOPUCM-ZEQRLZLVSA-N 0.000 claims description 2
- IFSWENYMWHDBOW-MHZLTWQESA-N (2S)-N-[2-(3-hydroxyphenyl)ethyl]-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCC=1C=C(O)C=CC=1)C(=O)C(C(=C1)C)=CC=C1C1=CC=CC=C1C IFSWENYMWHDBOW-MHZLTWQESA-N 0.000 claims description 2
- PILBJJQELKVQHB-SKCDSABHSA-N (2S)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-4-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC(O)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1OC PILBJJQELKVQHB-SKCDSABHSA-N 0.000 claims description 2
- RKVVLWLASJYMGS-PMCHYTPCSA-N (2S)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-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(O)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C RKVVLWLASJYMGS-PMCHYTPCSA-N 0.000 claims description 2
- QIDARADRWBGLRJ-SKCDSABHSA-N (2S)-N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC(=CC=1)[N+]([O-])=O)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QIDARADRWBGLRJ-SKCDSABHSA-N 0.000 claims description 2
- IJWQJDQXKIQXIH-NASUQTAISA-N (2S)-N-[2-hydroxy-3-(4-methoxyphenoxy)propyl]-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)COC=1C=CC(OC)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 IJWQJDQXKIQXIH-NASUQTAISA-N 0.000 claims description 2
- PIUNNVSTUDZYRR-HNNXBMFYSA-N (2S)-N-benzyl-4-methoxyimino-1-(3-oxobutanoyl)pyrrolidine-2-carboxamide Chemical compound CC(=O)CC(=O)N1CC(=NOC)C[C@H]1C(=O)NCC1=CC=CC=C1 PIUNNVSTUDZYRR-HNNXBMFYSA-N 0.000 claims description 2
- GJMUWHSVYVPFNP-DEOSSOPVSA-N (2S)-N-benzyl-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GJMUWHSVYVPFNP-DEOSSOPVSA-N 0.000 claims description 2
- CECYCJXNLCRXAB-LOSJGSFVSA-N (2s)-1-[4-(2-chlorophenyl)benzoyl]-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyiminopyrrolidine-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=CC=C1Cl CECYCJXNLCRXAB-LOSJGSFVSA-N 0.000 claims description 2
- SERKKACUUOMZSL-MHZLTWQESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1 SERKKACUUOMZSL-MHZLTWQESA-N 0.000 claims description 2
- NHSFKYKHMRBWGQ-SANMLTNESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(C1=CC=C(C=C1)C1=CC=NC=C1)=O NHSFKYKHMRBWGQ-SANMLTNESA-N 0.000 claims description 2
- LPZHFAIXHNLHJD-QFIPXVFZSA-N (4-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)O)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1 LPZHFAIXHNLHJD-QFIPXVFZSA-N 0.000 claims description 2
- VCHOKELVQXEXCY-QFIPXVFZSA-N (4-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)O)S(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 VCHOKELVQXEXCY-QFIPXVFZSA-N 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- QDYNVCIMQYLRPH-QHCPKHFHSA-N 1-[(2S)-2-(1H-benzimidazol-2-yl)-4-methoxyiminopyrrolidin-1-yl]-2,2-diphenylethanone Chemical compound CON=C1CN([C@@H](C1)C1=NC2=C(N1)C=CC=C2)C(C(C1=CC=CC=C1)C1=CC=CC=C1)=O QDYNVCIMQYLRPH-QHCPKHFHSA-N 0.000 claims description 2
- ZACTXZHUFYEMRD-IBGZPJMESA-N 1-[(2S)-2-(4-acetylpiperazine-1-carbonyl)-4-[(3,4-dichlorophenyl)methoxyimino]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C(CON=C2CN([C@@H](C2)C(=O)N2CCN(CC2)C(C)=O)C(C=C)=O)C=CC=1Cl ZACTXZHUFYEMRD-IBGZPJMESA-N 0.000 claims description 2
- CORONZGQECMTKT-FQEVSTJZSA-N 4-[[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carbonyl]amino]butanoic acid Chemical compound C1(=CC=C(C=C1)C(=O)N1[C@@H](CC(C1)=NOC)C(=O)NCCCC(=O)O)C1=CC=CC=C1 CORONZGQECMTKT-FQEVSTJZSA-N 0.000 claims description 2
- AAYGLUCTFBTTKO-PMVMPFDFSA-N C1(=CC=C(C=C1)C(=O)N1[C@@H](CC(C1)=NOC)C(=O)N[C@@H]1CC[C@H](CC1)O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C(=O)N1[C@@H](CC(C1)=NOC)C(=O)N[C@@H]1CC[C@H](CC1)O)C1=CC=CC=C1 AAYGLUCTFBTTKO-PMVMPFDFSA-N 0.000 claims description 2
- PUOKDQHOLIIUKL-NDEPHWFRSA-N [(2S)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidin-2-yl]-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C PUOKDQHOLIIUKL-NDEPHWFRSA-N 0.000 claims description 2
- LPUUOJWCFXGWSJ-VWLOTQADSA-N [4-(2-hydroxyethyl)piperazin-1-yl]-[(2S)-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)CCO)C(=O)C1=C(C=C(C=C1)C1=C(C=CC=C1)C)C LPUUOJWCFXGWSJ-VWLOTQADSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 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 description 2
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- IBXGJPAYWMFXSF-DCWQJPKNSA-N (2R)-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-DCWQJPKNSA-N 0.000 claims 1
- KNWCIKJGJWANBM-SANMLTNESA-N (2S)-1-[4-(2,6-dimethylphenyl)benzoyl]-N-[2-(3-hydroxyphenyl)ethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCC=1C=C(O)C=CC=1)C(=O)C(C=C1)=CC=C1C1=C(C)C=CC=C1C KNWCIKJGJWANBM-SANMLTNESA-N 0.000 claims 1
- CMMIYGWQOYKAPX-INIZCTEOSA-N (2S)-1-acetyl-N-cyclopropyl-4-[(3,4-dichlorophenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)C)=NOCC=1C=C(Cl)C(Cl)=CC=1)NC1CC1 CMMIYGWQOYKAPX-INIZCTEOSA-N 0.000 claims 1
- IJDLKEFKYYEMFB-MBABXSBOSA-N (2S)-N-(1-hydroxypropan-2-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NC(C)CO)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 IJDLKEFKYYEMFB-MBABXSBOSA-N 0.000 claims 1
- BHMIBXUVZFWQQQ-IJHRGXPZSA-N (2S)-N-(2,3-dihydroxypropyl)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound C1C(=NOC)C[C@@H](C(=O)NCC(O)CO)N1S(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 BHMIBXUVZFWQQQ-IJHRGXPZSA-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
- 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
- ZWFOHTWIILLQNE-GSDHBNRESA-N (2S)-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-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)[N+]([O-])=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZWFOHTWIILLQNE-GSDHBNRESA-N 0.000 claims 1
- PIKZDPDQPMBMLA-BJKOFHAPSA-N (2S)-N-[(2S)-2-hydroxy-2-(4-nitrophenyl)ethyl]-4-methoxyimino-1-(4-pyridin-2-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC[C@@H](O)C=1C=CC(=CC=1)[N+]([O-])=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=N1 PIKZDPDQPMBMLA-BJKOFHAPSA-N 0.000 claims 1
- AZWIHVUPVASMLM-LOSJGSFVSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]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=CC=C1OC AZWIHVUPVASMLM-LOSJGSFVSA-N 0.000 claims 1
- NFFPMIZCDVSWEF-QHCPKHFHSA-N (2S)-N-[2-(diethylamino)ethyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound CCN(CC)CCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 NFFPMIZCDVSWEF-QHCPKHFHSA-N 0.000 claims 1
- FONGKLKJCGSJKT-SKCDSABHSA-N (2S)-N-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=C(O)C=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 FONGKLKJCGSJKT-SKCDSABHSA-N 0.000 claims 1
- IVFWRENFYZXHJY-NMXAJACMSA-N (2S)-N-[3-(4-acetamidophenoxy)-2-hydroxypropyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)COC=1C=CC(NC(C)=O)=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 IVFWRENFYZXHJY-NMXAJACMSA-N 0.000 claims 1
- XJVDFRDPCAAANB-INIZCTEOSA-N (2S)-N-cyclopropyl-4-[(3,4-dichlorophenyl)methoxyimino]-1-(2-methoxyacetyl)pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)COC)=NOCC=1C=C(Cl)C(Cl)=CC=1)NC1CC1 XJVDFRDPCAAANB-INIZCTEOSA-N 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- DAJNANNJGQLQCG-UHFFFAOYSA-N 5,5-dichloro-2-phenylcyclohexa-1,3-diene Chemical compound C1=CC(Cl)(Cl)CC=C1C1=CC=CC=C1 DAJNANNJGQLQCG-UHFFFAOYSA-N 0.000 claims 1
- RZRSXJVNVKHMEC-QHCPKHFHSA-N [(2s)-2-(1h-benzimidazol-2-yl)-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1NC2=CC=CC=C2N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RZRSXJVNVKHMEC-QHCPKHFHSA-N 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 14
- 208000005107 Premature Birth Diseases 0.000 abstract description 9
- 206010036590 Premature baby Diseases 0.000 abstract description 9
- 239000005557 antagonist Substances 0.000 abstract description 9
- 206010013935 Dysmenorrhoea Diseases 0.000 abstract 2
- 230000006806 disease prevention Effects 0.000 abstract 1
- RPEKVXSOLUPBLF-QMMMGPOBSA-N (2s)-4-methoxyimino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CON=C1C[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C1 RPEKVXSOLUPBLF-QMMMGPOBSA-N 0.000 description 223
- 238000004128 high performance liquid chromatography Methods 0.000 description 187
- 239000000243 solution Substances 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 63
- 239000000047 product Substances 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 36
- OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 31
- 239000000543 intermediate Substances 0.000 description 30
- ULSIYEODSMZIPX-UHFFFAOYSA-N alpha-hydroxyphenethylamine Natural products NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 26
- 230000008020 evaporation Effects 0.000 description 26
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- SNSIPZVPHKFNNE-AWEZNQCLSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)CC1=NOCC1=CC=C(Cl)C(Cl)=C1 SNSIPZVPHKFNNE-AWEZNQCLSA-N 0.000 description 24
- CIGUFUOEWMSYRZ-VIFPVBQESA-N (2s)-4-ethoxyimino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CCON=C1C[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C1 CIGUFUOEWMSYRZ-VIFPVBQESA-N 0.000 description 24
- ULLGRIBXGPATMA-QMMMGPOBSA-N (2s)-4-methylidene-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=C)C[C@H]1C(O)=O ULLGRIBXGPATMA-QMMMGPOBSA-N 0.000 description 24
- ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000005336 allyloxy group Chemical group 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 20
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- XDWPYVCCHXZUIF-QMMMGPOBSA-N (2s)-4-(chloromethylidene)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=CCl)C[C@H]1C(O)=O XDWPYVCCHXZUIF-QMMMGPOBSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- JKBGXBVHOKKEJO-UHFFFAOYSA-N 2-oxo-6-pentylpyran-3-carbonyl chloride Chemical compound CCCCCC1=CC=C(C(Cl)=O)C(=O)O1 JKBGXBVHOKKEJO-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- GYUKEVKPDRXPAB-UHFFFAOYSA-N 4-pyridin-3-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CN=C1 GYUKEVKPDRXPAB-UHFFFAOYSA-N 0.000 description 14
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- CKYGSXRXTIKGAJ-ZETCQYMHSA-N Boc-L-Pro(4-oxo) Chemical compound CC(C)(C)OC(=O)N1CC(=O)C[C@H]1C(O)=O CKYGSXRXTIKGAJ-ZETCQYMHSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- BVMAZGVZDDQOCK-VIFPVBQESA-N (2S)-4-(cyanomethylidene)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=CC#N)C[C@H]1C(O)=O BVMAZGVZDDQOCK-VIFPVBQESA-N 0.000 description 12
- LZGDLTYIHXNYJS-UHFFFAOYSA-N 2-methyl-4-(2-methylphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C(=CC=CC=2)C)=C1 LZGDLTYIHXNYJS-UHFFFAOYSA-N 0.000 description 12
- NDNIPPKLIDCYGD-UHFFFAOYSA-N 4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 NDNIPPKLIDCYGD-UHFFFAOYSA-N 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- KFWHBPOVEJXVMG-AWEZNQCLSA-N (2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylmethoxyiminopyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)CC1=NOCC1=CC=CC=C1 KFWHBPOVEJXVMG-AWEZNQCLSA-N 0.000 description 11
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 11
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 11
- LRGHHVXWOZHPJF-UHFFFAOYSA-N 4-(dimethylamino)butanoyl chloride Chemical compound CN(C)CCCC(Cl)=O LRGHHVXWOZHPJF-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 11
- 239000012346 acetyl chloride Substances 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- RJAKZBYHWDNYMB-JTQLQIEISA-N (2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-[(2-methylpropan-2-yl)oxyimino]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)ON=C1C[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C1 RJAKZBYHWDNYMB-JTQLQIEISA-N 0.000 description 10
- CESHOVLNBLNJFH-JTQLQIEISA-N (2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-prop-2-enoxyiminopyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=NOCC=C)C[C@H]1C(O)=O CESHOVLNBLNJFH-JTQLQIEISA-N 0.000 description 10
- VCGOBBQPUHQZAG-HNNXBMFYSA-N (2s)-4-[(4-methoxyphenyl)methoxyimino]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CON=C1CN(C(=O)OC(C)(C)C)[C@H](C(O)=O)C1 VCGOBBQPUHQZAG-HNNXBMFYSA-N 0.000 description 10
- XTBFLTVDBQAKKZ-AWEZNQCLSA-N (2s)-4-benzylidene-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)CC1=CC1=CC=CC=C1 XTBFLTVDBQAKKZ-AWEZNQCLSA-N 0.000 description 10
- USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 10
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 10
- ULSIYEODSMZIPX-MRVPVSSYSA-N (1s)-2-amino-1-phenylethanol Chemical compound NC[C@@H](O)C1=CC=CC=C1 ULSIYEODSMZIPX-MRVPVSSYSA-N 0.000 description 9
- DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 9
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 9
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical compound COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 9
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 9
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 9
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 9
- DZLGZIGLHCRIMF-UHFFFAOYSA-N 4-pyridin-4-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=NC=C1 DZLGZIGLHCRIMF-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 150000002923 oximes Chemical group 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 description 8
- AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 description 8
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- LDNLTMRRJNZNRE-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)benzoic acid Chemical compound CC1=CC=CC(C)=C1C1=CC=C(C(O)=O)C=C1 LDNLTMRRJNZNRE-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- ULSIYEODSMZIPX-QMMMGPOBSA-N (1r)-2-amino-1-phenylethanol Chemical compound NC[C@H](O)C1=CC=CC=C1 ULSIYEODSMZIPX-QMMMGPOBSA-N 0.000 description 5
- VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- AQIPNZHMXANQRC-UHFFFAOYSA-N 4-pyridin-2-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=N1 AQIPNZHMXANQRC-UHFFFAOYSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 5
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical compound NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 description 5
- JUCGVCVPNPBJIG-IUCAKERBSA-N (1s,2s)-2-amino-1-phenylpropane-1,3-diol Chemical compound OC[C@H](N)[C@@H](O)C1=CC=CC=C1 JUCGVCVPNPBJIG-IUCAKERBSA-N 0.000 description 4
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 4
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 4
- PAIOJXKJICQPAT-UHFFFAOYSA-N 1-ethyl-9h-carbazol-3-amine Chemical compound N1C2=CC=CC=C2C2=C1C(CC)=CC(N)=C2 PAIOJXKJICQPAT-UHFFFAOYSA-N 0.000 description 4
- UPBHYYJZVWZCOZ-QMMMGPOBSA-N 1-o-tert-butyl 2-o-methyl (2s)-4-oxopyrrolidine-1,2-dicarboxylate Chemical compound COC(=O)[C@@H]1CC(=O)CN1C(=O)OC(C)(C)C UPBHYYJZVWZCOZ-QMMMGPOBSA-N 0.000 description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 4
- DRLGIZIAMHIQHL-UHFFFAOYSA-N 2,1,3-benzothiadiazol-4-amine Chemical compound NC1=CC=CC2=NSN=C12 DRLGIZIAMHIQHL-UHFFFAOYSA-N 0.000 description 4
- DZOWZBGCZPHHLM-UHFFFAOYSA-N 2-amino-1-(4-nitrophenyl)ethanol Chemical compound NCC(O)C1=CC=C([N+]([O-])=O)C=C1 DZOWZBGCZPHHLM-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 4
- YQLGXBYAHYGABI-UHFFFAOYSA-N 4-(2-methoxyphenyl)benzoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 YQLGXBYAHYGABI-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000010976 amide bond formation reaction Methods 0.000 description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 229960000367 inositol Drugs 0.000 description 4
- 239000012948 isocyanate Chemical group 0.000 description 4
- 150000002513 isocyanates Chemical group 0.000 description 4
- GHFGJTVYMNRGBY-UHFFFAOYSA-N m-tyramine Chemical compound NCCC1=CC=CC(O)=C1 GHFGJTVYMNRGBY-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 4
- RQWDNMOAQIUREU-UHFFFAOYSA-N n-[4-(3-amino-2-hydroxypropoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(O)CN)C=C1 RQWDNMOAQIUREU-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- LRCXRAABFLIVAI-UHFFFAOYSA-N norfenefrine Chemical compound NCC(O)C1=CC=CC(O)=C1 LRCXRAABFLIVAI-UHFFFAOYSA-N 0.000 description 4
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 4
- 229960001634 ritodrine Drugs 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- DXNKJRKPVQVDJW-NTSWFWBYSA-N (1s,2r)-2-aminocyclohexane-1-carboxamide Chemical compound N[C@@H]1CCCC[C@@H]1C(N)=O DXNKJRKPVQVDJW-NTSWFWBYSA-N 0.000 description 3
- OCYJXSUPZMNXEN-IUCAKERBSA-N (1s,2s)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol Chemical compound OC[C@H](N)[C@@H](O)C1=CC=C([N+]([O-])=O)C=C1 OCYJXSUPZMNXEN-IUCAKERBSA-N 0.000 description 3
- MLMDRTCOOJIVBB-LOSJGSFVSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-phenylbenzoyl)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=CC=C1 MLMDRTCOOJIVBB-LOSJGSFVSA-N 0.000 description 3
- PQZOLIMRVXLZDK-UXMRNZNESA-N (2s)-n-(2-hydroxy-2-phenylethyl)-4-oxo-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCC(O)C=2C=CC=CC=2)C(=O)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PQZOLIMRVXLZDK-UXMRNZNESA-N 0.000 description 3
- LNOLJFCCYQZFBQ-BUHFOSPRSA-N (ne)-n-[(4-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=N/O)/C1=CC=CC=C1 LNOLJFCCYQZFBQ-BUHFOSPRSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XUSXTHMTOSFZII-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1(O)CCCCC1 XUSXTHMTOSFZII-UHFFFAOYSA-N 0.000 description 3
- KFQPRNVTVMCYEH-UHFFFAOYSA-N 1-amino-3-(4-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CN)C=C1 KFQPRNVTVMCYEH-UHFFFAOYSA-N 0.000 description 3
- CRVBQABBEKLFIN-UHFFFAOYSA-N 1-phenylethane-1,2-diamine Chemical compound NCC(N)C1=CC=CC=C1 CRVBQABBEKLFIN-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 3
- GDMZHPUPLWQIBD-UHFFFAOYSA-N 2-pyrrol-1-ylaniline Chemical compound NC1=CC=CC=C1N1C=CC=C1 GDMZHPUPLWQIBD-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100248451 Arabidopsis thaliana RICE2 gene Proteins 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229940122828 Oxytocin receptor antagonist Drugs 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000012317 TBTU Substances 0.000 description 3
- GCWPGEWXYDEQAY-NKWVEPMBSA-N [(1r,2r)-2-aminocyclohexyl]methanol Chemical compound N[C@@H]1CCCC[C@H]1CO GCWPGEWXYDEQAY-NKWVEPMBSA-N 0.000 description 3
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 239000000048 adrenergic agonist Substances 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000001275 ca(2+)-mobilization Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical group ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 3
- 150000002540 isothiocyanates Chemical group 0.000 description 3
- 208000037805 labour Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- PHIYHIOQVWTXII-SECBINFHSA-N (1r)-3-amino-1-phenylpropan-1-ol Chemical compound NCC[C@@H](O)C1=CC=CC=C1 PHIYHIOQVWTXII-SECBINFHSA-N 0.000 description 2
- SCQSHSJVMGGQKR-BNHYGAARSA-N (1r,2s,3r,4s)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1[C@@H]2C=C[C@H]1[C@@H](N)[C@H]2C(N)=O SCQSHSJVMGGQKR-BNHYGAARSA-N 0.000 description 2
- PHIYHIOQVWTXII-VIFPVBQESA-N (1s)-3-amino-1-phenylpropan-1-ol Chemical compound NCC[C@H](O)C1=CC=CC=C1 PHIYHIOQVWTXII-VIFPVBQESA-N 0.000 description 2
- PQMCFTMVQORYJC-WDSKDSINSA-N (1s,2s)-2-aminocyclohexan-1-ol Chemical compound N[C@H]1CCCC[C@@H]1O PQMCFTMVQORYJC-WDSKDSINSA-N 0.000 description 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 description 2
- BSOLESBXSVPDAV-PMCHYTPCSA-N (2S)-1-[2-(4-chlorophenoxy)acetyl]-4-[(3,4-dichlorophenyl)methoxyimino]-N-(2-hydroxy-2-phenylethyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCC(O)C=2C=CC=CC=2)C(=NOCC=2C=C(Cl)C(Cl)=CC=2)CN1C(=O)COC1=CC=C(Cl)C=C1 BSOLESBXSVPDAV-PMCHYTPCSA-N 0.000 description 2
- SYRQZKJVBWTQRA-SKCDSABHSA-N (2S)-1-[4-(3,4-dichlorophenyl)benzoyl]-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=C1C1=CC=C(Cl)C(Cl)=C1 SYRQZKJVBWTQRA-SKCDSABHSA-N 0.000 description 2
- USWMANJNGPQNGZ-SANMLTNESA-N (2S)-1-benzoyl-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@H](C(=O)NC=2C=C3C=CC=NC3=CC=2)C1 USWMANJNGPQNGZ-SANMLTNESA-N 0.000 description 2
- UYYYPUFJMIFSRT-PMCHYTPCSA-N (2S)-4-(acetylhydrazinylidene)-N-(2-hydroxy-2-phenylethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NNC(=O)C)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 UYYYPUFJMIFSRT-PMCHYTPCSA-N 0.000 description 2
- RYFNREVOJPOJRU-QWAKEFERSA-N (2S)-N-(2,3-dihydroxypropyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]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)C=C1 RYFNREVOJPOJRU-QWAKEFERSA-N 0.000 description 2
- YQQQPQPFVLLOOC-SKCDSABHSA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-(methylhydrazinylidene)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NNC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 YQQQPQPFVLLOOC-SKCDSABHSA-N 0.000 description 2
- GKLWVFORFUTTFB-QMMMGPOBSA-N (2S)-N-(2-methoxyethyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound COCCNC(=O)[C@@H]1CC(=NOC)CN1 GKLWVFORFUTTFB-QMMMGPOBSA-N 0.000 description 2
- QRPWTYXVHXMYBP-QFIPXVFZSA-N (2S)-N-[(1-hydroxycyclohexyl)methyl]-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC1(O)CCCCC1)C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 QRPWTYXVHXMYBP-QFIPXVFZSA-N 0.000 description 2
- WKXFOPDKOGFFPV-SDHOMARFSA-N (2S)-N-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)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=NC=C1 WKXFOPDKOGFFPV-SDHOMARFSA-N 0.000 description 2
- DHALQIDCVXDZBY-IZZNHLLZSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(3-methyl-4-phenylbenzoyl)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=C1C)=CC=C1C1=CC=CC=C1 DHALQIDCVXDZBY-IZZNHLLZSA-N 0.000 description 2
- XSNMARAPVLZPOL-LOSJGSFVSA-N (2S)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-[4-[2-(trifluoromethyl)phenyl]benzoyl]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=CC=C1C(F)(F)F XSNMARAPVLZPOL-LOSJGSFVSA-N 0.000 description 2
- PQYQVUPCTGPBJE-IZZNHLLZSA-N (2S)-N-[(3R)-3-hydroxy-3-phenylpropyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PQYQVUPCTGPBJE-IZZNHLLZSA-N 0.000 description 2
- PQYQVUPCTGPBJE-UIOOFZCWSA-N (2S)-N-[(3S)-3-hydroxy-3-phenylpropyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC[C@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PQYQVUPCTGPBJE-UIOOFZCWSA-N 0.000 description 2
- HLYIUIAODDCEFB-SVBPBHIXSA-N (2S)-N-[(3S)-3-hydroxy-3-phenylpropyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC[C@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C HLYIUIAODDCEFB-SVBPBHIXSA-N 0.000 description 2
- AQNGNLLVMPBMSC-MHZLTWQESA-N (2S)-N-[2-(4-hydroxyphenyl)ethyl]-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCC=1C=CC(O)=CC=1)C(=O)C(C(=C1)C)=CC=C1C1=CC=CC=C1C AQNGNLLVMPBMSC-MHZLTWQESA-N 0.000 description 2
- KFBDLVSNARYKNS-VWLOTQADSA-N (2S)-N-benzyl-4-methoxyimino-N-methyl-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N(C)CC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KFBDLVSNARYKNS-VWLOTQADSA-N 0.000 description 2
- FEXKDCIQCLQUGX-SANMLTNESA-N (2S)-N-benzyl-N-(2-hydroxyethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N(CCO)CC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 FEXKDCIQCLQUGX-SANMLTNESA-N 0.000 description 2
- NBRAKNKPMMFFAZ-VWLOTQADSA-N (2S)-N-benzyl-N-(2-hydroxyethyl)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N(CCO)CC=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 NBRAKNKPMMFFAZ-VWLOTQADSA-N 0.000 description 2
- DRQRLKKDHPSEIG-SANMLTNESA-N (2S)-N-cyclopropyl-4-[(3,4-dichlorophenyl)methoxyimino]-1-(2,2-diphenylacetyl)pyrrolidine-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CON=C1CN(C(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)[C@H](C(=O)NC2CC2)C1 DRQRLKKDHPSEIG-SANMLTNESA-N 0.000 description 2
- HLYIUIAODDCEFB-RRPNLBNLSA-N (2s)-n-[(3r)-3-hydroxy-3-phenylpropyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C HLYIUIAODDCEFB-RRPNLBNLSA-N 0.000 description 2
- MLMDRTCOOJIVBB-FEWLIHMASA-N (2s,4e)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C\C(C1)=N/OC)C(=O)NC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MLMDRTCOOJIVBB-FEWLIHMASA-N 0.000 description 2
- MWGOCMCGXRJYQT-MHZLTWQESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)S(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 MWGOCMCGXRJYQT-MHZLTWQESA-N 0.000 description 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- NBOOZXVYXHATOW-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)piperazine Chemical compound C=1C=C2OCOC2=CC=1CN1CCNCC1 NBOOZXVYXHATOW-UHFFFAOYSA-N 0.000 description 2
- CCYVIVOXBQDOKH-UHFFFAOYSA-N 1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)COC1=CC=CC=C1 CCYVIVOXBQDOKH-UHFFFAOYSA-N 0.000 description 2
- PXFJLKKZSWWVRX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCNCC1 PXFJLKKZSWWVRX-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
- FMHLUYMKOSEANZ-UHFFFAOYSA-N 1-phenylpiperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC=CC=C1 FMHLUYMKOSEANZ-UHFFFAOYSA-N 0.000 description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 2
- MZICESGONBDFKR-UHFFFAOYSA-N 2-(thiophen-2-ylmethyl)pyrrolidine-1,2-dicarboxamide Chemical compound NC(=O)N1CCCC1(C(N)=O)CC1=CC=CS1 MZICESGONBDFKR-UHFFFAOYSA-N 0.000 description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 2
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 2
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 2
- VFUQEPLYJYIJSA-OYKVQYDMSA-N 2-hydroxy-3-[[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound C1(=CC=C(C=C1)C(=O)N1[C@@H](CC(C1)=NOC)C(=O)NCC(C(=O)O)O)C1=CC=CC=C1 VFUQEPLYJYIJSA-OYKVQYDMSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- KUZNURGIXXKBEJ-UHFFFAOYSA-N 3-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=CN=C1 KUZNURGIXXKBEJ-UHFFFAOYSA-N 0.000 description 2
- YMOCYJHFDJRMGY-UHFFFAOYSA-N 3-(oxomethylidene)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1NCCC1=C=O YMOCYJHFDJRMGY-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- ZGBAXFOVTPCBRW-UHFFFAOYSA-N 3-methyl-4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1C ZGBAXFOVTPCBRW-UHFFFAOYSA-N 0.000 description 2
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 2
- UQTIMPXCTPPTSJ-UHFFFAOYSA-N 4-(1-oxidopyridin-1-ium-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C[N+]([O-])=C1 UQTIMPXCTPPTSJ-UHFFFAOYSA-N 0.000 description 2
- MZIFVOLYXURHDM-UHFFFAOYSA-N 4-(2-cyanophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C#N MZIFVOLYXURHDM-UHFFFAOYSA-N 0.000 description 2
- BNNVIEYGJYMYHU-UHFFFAOYSA-N 4-(3-methylpyridin-2-yl)benzoic acid Chemical compound CC1=CC=CN=C1C1=CC=C(C(O)=O)C=C1 BNNVIEYGJYMYHU-UHFFFAOYSA-N 0.000 description 2
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 2
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 2
- MAUFTTLGOUBZNA-UHFFFAOYSA-N 6-n-Pentyl-alpha-pyrone Chemical compound CCCCCC1=CC=CC(=O)O1 MAUFTTLGOUBZNA-UHFFFAOYSA-N 0.000 description 2
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 101000986765 Homo sapiens Oxytocin receptor Proteins 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- CPCSMTDGCKVENS-UHFFFAOYSA-N N=C1C(N(CC1)C(=O)OC(C)(C)C)C(=O)O Chemical compound N=C1C(N(CC1)C(=O)OC(C)(C)C)C(=O)O CPCSMTDGCKVENS-UHFFFAOYSA-N 0.000 description 2
- HBVZRPAKZOLBPL-UHFFFAOYSA-N O-Acetylethanolamine Chemical compound CC(=O)OCCN HBVZRPAKZOLBPL-UHFFFAOYSA-N 0.000 description 2
- 102100028139 Oxytocin receptor Human genes 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QGMMKSUHQMVLRO-OSMVPFSASA-N [(1s,2r,3s,4r)-3-amino-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1C[C@]2([H])[C@@H](CO)[C@@H](N)[C@@]1([H])C2 QGMMKSUHQMVLRO-OSMVPFSASA-N 0.000 description 2
- BHZIXWRWYBBDHE-UHFFFAOYSA-N [4-(3-methylpyridin-2-yl)phenyl]methanol Chemical compound CC1=CC=CN=C1C1=CC=C(CO)C=C1 BHZIXWRWYBBDHE-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 210000004696 endometrium Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000010230 functional analysis Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- MVSMBIBGGPSEHQ-UHFFFAOYSA-N o-[(4-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CON)C=C1 MVSMBIBGGPSEHQ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000003336 oxytocin antagonist Substances 0.000 description 2
- 229940121361 oxytocin antagonists Drugs 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- PTGYSDQJBTUHDE-AWEZNQCLSA-N tert-butyl (2S)-2-(1H-benzimidazol-2-yl)-4-methoxyiminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=NOC)C[C@H]1C1=NC2=CC=CC=C2N1 PTGYSDQJBTUHDE-AWEZNQCLSA-N 0.000 description 2
- MKFPOJRBPDTTOF-NSHDSACASA-N tert-butyl (2S)-2-(2-methoxyethylcarbamoyl)-4-methoxyiminopyrrolidine-1-carboxylate Chemical compound COCCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)OC(C)(C)C MKFPOJRBPDTTOF-NSHDSACASA-N 0.000 description 2
- GXUCZIZHYAWICH-AWEZNQCLSA-N tert-butyl (2S)-2-[(2-aminophenyl)carbamoyl]-4-methoxyiminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=NOC)C[C@H]1C(=O)NC1=CC=CC=C1N GXUCZIZHYAWICH-AWEZNQCLSA-N 0.000 description 2
- MNDIAGQXNDMLCK-JKSUJKDBSA-N tert-butyl (2S)-2-[[(2S)-2-hydroxy-2-phenylethyl]carbamoyl]-4-methoxyiminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=NOC)C[C@H]1C(=O)NC[C@@H](O)C1=CC=CC=C1 MNDIAGQXNDMLCK-JKSUJKDBSA-N 0.000 description 2
- WPGLRFGDZJSQGI-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(N)C1 WPGLRFGDZJSQGI-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229940125712 tocolytic agent Drugs 0.000 description 2
- 239000003675 tocolytic agent Substances 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
- GEJJWYZZKKKSEV-KGLIPLIRSA-N (1s,2r)-2-amino-1,2-diphenylethanol Chemical compound C1([C@H](O)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1 GEJJWYZZKKKSEV-KGLIPLIRSA-N 0.000 description 1
- VLXDQDJEENQBCU-UHFFFAOYSA-N (2-amino-1-phenylethyl) acetate Chemical compound CC(=O)OC(CN)C1=CC=CC=C1 VLXDQDJEENQBCU-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- CWSHOHJOWSYWKA-HKBQPEDESA-N (2S)-1-(2-ethoxynaphthalene-1-carbonyl)-N-(9-ethylcarbazol-3-yl)-4-[(2-methylpropan-2-yl)oxyimino]pyrrolidine-2-carboxamide Chemical compound C1=CC=C2C3=CC(NC(=O)[C@@H]4CC(CN4C(=O)C4=C5C=CC=CC5=CC=C4OCC)=NOC(C)(C)C)=CC=C3N(CC)C2=C1 CWSHOHJOWSYWKA-HKBQPEDESA-N 0.000 description 1
- IZPPGUFSYASDJP-LJAQVGFWSA-N (2S)-1-(2-oxo-6-pentylpyran-3-carbonyl)-4-phenylmethoxyimino-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N(C1)[C@H](C(=O)NC=2C=C3C=CC=NC3=CC=2)CC1=NOCC1=CC=CC=C1 IZPPGUFSYASDJP-LJAQVGFWSA-N 0.000 description 1
- NBHPCNSZGYCHTO-LJAQVGFWSA-N (2S)-1-(4-cyanobenzoyl)-4-[(3,4-dichlorophenyl)methoxyimino]-N-(naphthalen-1-ylmethyl)pyrrolidine-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)NCC=2C3=CC=CC=C3C=CC=2)C1 NBHPCNSZGYCHTO-LJAQVGFWSA-N 0.000 description 1
- RBOUOOFKTBEFGY-SANMLTNESA-N (2S)-1-(4-cyanobenzoyl)-N-(9-ethylcarbazol-3-yl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=NOC)CN1C(=O)C1=CC=C(C#N)C=C1 RBOUOOFKTBEFGY-SANMLTNESA-N 0.000 description 1
- DQLVKUFMHSUNTR-QHCPKHFHSA-N (2S)-1-(4-cyanobenzoyl)-N-(furan-2-ylmethyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CC(C1)=NOCC=1C=CC=CC=1)C(=O)C=1C=CC(=CC=1)C#N)NCC1=CC=CO1 DQLVKUFMHSUNTR-QHCPKHFHSA-N 0.000 description 1
- QMOMVBYOZHBYDV-SFHVURJKSA-N (2S)-1-(4-cyanobenzoyl)-N-[2-(diethylamino)ethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CCN(CC)CCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C1=CC=C(C#N)C=C1 QMOMVBYOZHBYDV-SFHVURJKSA-N 0.000 description 1
- OOVVCTZUOMXAKU-VWLOTQADSA-N (2S)-1-N-benzoyl-2-N-(9-ethylcarbazol-3-yl)-4-methoxyiminopyrrolidine-1,2-dicarboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=NOC)CN1C(=O)NC(=O)C1=CC=CC=C1 OOVVCTZUOMXAKU-VWLOTQADSA-N 0.000 description 1
- CVINOHYMCWNZIQ-VWLOTQADSA-N (2S)-1-N-benzoyl-2-N-benzyl-2-N-methyl-4-phenylmethoxyiminopyrrolidine-1,2-dicarboxamide Chemical compound O=C([C@H]1N(CC(C1)=NOCC=1C=CC=CC=1)C(=O)NC(=O)C=1C=CC=CC=1)N(C)CC1=CC=CC=C1 CVINOHYMCWNZIQ-VWLOTQADSA-N 0.000 description 1
- JSVFEODLGBFGKU-AWEZNQCLSA-N (2S)-1-N-benzoyl-4-(chloromethylidene)-2-N-cyclopropylpyrrolidine-1,2-dicarboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NC1CC1)C(=O)NC(=O)C1=CC=CC=C1 JSVFEODLGBFGKU-AWEZNQCLSA-N 0.000 description 1
- RADAHCNSLKRPAY-SANMLTNESA-N (2S)-1-N-benzoyl-4-(cyanomethylidene)-2-N-(9-ethylcarbazol-3-yl)pyrrolidine-1,2-dicarboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=CC#N)CN1C(=O)NC(=O)C1=CC=CC=C1 RADAHCNSLKRPAY-SANMLTNESA-N 0.000 description 1
- FKCYOWAYHLPHHX-MHZLTWQESA-N (2S)-1-[2-(4-chlorophenoxy)acetyl]-4-ethoxyimino-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC)C(=O)NC=1C=C2C3=CC=CC=C3N(CC)C2=CC=1)C(=O)COC1=CC=C(Cl)C=C1 FKCYOWAYHLPHHX-MHZLTWQESA-N 0.000 description 1
- DGNUQDYMLFUJBX-SANMLTNESA-N (2S)-1-[4-(2,6-dimethylphenyl)benzoyl]-N-[2-(4-hydroxyphenyl)ethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCCC=1C=CC(O)=CC=1)C(=O)C(C=C1)=CC=C1C1=C(C)C=CC=C1C DGNUQDYMLFUJBX-SANMLTNESA-N 0.000 description 1
- BSUPMCNNJTTYSG-BGERDNNASA-N (2S)-1-acetyl-4-[(3,4-dichlorophenyl)methoxyimino]-N-(2-hydroxy-2-phenylethyl)pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)C)=NOCC=1C=C(Cl)C(Cl)=CC=1)NCC(O)C1=CC=CC=C1 BSUPMCNNJTTYSG-BGERDNNASA-N 0.000 description 1
- OICFKOWYEOVEIE-SFHVURJKSA-N (2S)-1-acetyl-4-[(3,4-dichlorophenyl)methoxyimino]-N-(furan-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)C)=NOCC=1C=C(Cl)C(Cl)=CC=1)NCC1=CC=CO1 OICFKOWYEOVEIE-SFHVURJKSA-N 0.000 description 1
- SJNPBGZFUOXKST-DEOSSOPVSA-N (2S)-1-acetyl-4-[(3,4-dichlorophenyl)methoxyimino]-N-(naphthalen-1-ylmethyl)pyrrolidine-2-carboxamide Chemical compound CC(=O)N([C@@H](C1)C(=O)NCC=2C3=CC=CC=C3C=CC=2)CC1=NOCC1=CC=C(Cl)C(Cl)=C1 SJNPBGZFUOXKST-DEOSSOPVSA-N 0.000 description 1
- JZFOCRNKTMQCAX-QFIPXVFZSA-N (2S)-1-acetyl-4-ethoxyimino-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CC(=NOCC)C[C@H]1C(=O)NC1=CC=C(N(CC)C=2C3=CC=CC=2)C3=C1 JZFOCRNKTMQCAX-QFIPXVFZSA-N 0.000 description 1
- PJXMMRSMAYDWLN-NRFANRHFSA-N (2S)-1-acetyl-N-(9-ethylcarbazol-3-yl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=NOC)CN1C(C)=O PJXMMRSMAYDWLN-NRFANRHFSA-N 0.000 description 1
- YNMXVLBIGBTEDB-INIZCTEOSA-N (2S)-1-benzoyl-4-(chloromethylidene)-N-(furan-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NCC=1OC=CC=1)C(=O)C1=CC=CC=C1 YNMXVLBIGBTEDB-INIZCTEOSA-N 0.000 description 1
- MNMQKUBNWPBPLD-QHCPKHFHSA-N (2S)-1-benzoyl-4-(cyanomethylidene)-N-(naphthalen-1-ylmethyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(NCC=2C3=CC=CC=C3C=CC=2)=O)C(=CC#N)CN1C(=O)C1=CC=CC=C1 MNMQKUBNWPBPLD-QHCPKHFHSA-N 0.000 description 1
- WWPKSFBOUQFLRC-HKBQPEDESA-N (2S)-1-benzoyl-4-benzylidene-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=CC=2C=CC=CC=2)CN1C(=O)C1=CC=CC=C1 WWPKSFBOUQFLRC-HKBQPEDESA-N 0.000 description 1
- HEIUXJPLLGWWDY-QHCPKHFHSA-N (2S)-1-benzoyl-N-(furan-2-ylmethyl)-4-[(4-methoxyphenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CON=C1CN(C(=O)C=2C=CC=CC=2)[C@H](C(=O)NCC=2OC=CC=2)C1 HEIUXJPLLGWWDY-QHCPKHFHSA-N 0.000 description 1
- GCSMDENMFQNJFL-SFHVURJKSA-N (2S)-1-benzoyl-N-[2-(diethylamino)ethyl]-4-ethoxyiminopyrrolidine-2-carboxamide Chemical compound C1C(=NOCC)C[C@@H](C(=O)NCCN(CC)CC)N1C(=O)C1=CC=CC=C1 GCSMDENMFQNJFL-SFHVURJKSA-N 0.000 description 1
- JEJPJOLEPPUXCH-KRWDZBQOSA-N (2S)-1-benzoyl-N-[2-(diethylamino)ethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CCN(CC)CCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C1=CC=CC=C1 JEJPJOLEPPUXCH-KRWDZBQOSA-N 0.000 description 1
- MHANLVCVBBCLDI-IBGZPJMESA-N (2S)-1-benzoyl-N-benzyl-4-(chloromethylidene)-N-methylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CC(C1)=CCl)C(=O)C=1C=CC=CC=1)N(C)CC1=CC=CC=C1 MHANLVCVBBCLDI-IBGZPJMESA-N 0.000 description 1
- YMTJJYIIMBRJND-QHCPKHFHSA-N (2S)-2-N-(1,3-benzodioxol-5-ylmethyl)-4-[(4-methoxyphenyl)methoxyimino]-1-N-pentylpyrrolidine-1,2-dicarboxamide Chemical compound CCCCCNC(=O)N([C@@H](C1)C(=O)NCC=2C=C3OCOC3=CC=2)CC1=NOCC1=CC=C(OC)C=C1 YMTJJYIIMBRJND-QHCPKHFHSA-N 0.000 description 1
- KBPLAFNDCSHNNA-INIZCTEOSA-N (2S)-2-N-(2,1,3-benzothiadiazol-4-yl)-1-N-(3,5-dichlorophenyl)-4-methoxyiminopyrrolidine-1,2-dicarboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NC=1C2=NSN=C2C=CC=1)C(=O)NC1=CC(Cl)=CC(Cl)=C1 KBPLAFNDCSHNNA-INIZCTEOSA-N 0.000 description 1
- ZHZBZGRSNBXIBX-XJDOXCRVSA-N (2S)-2-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-N-(3-methylphenyl)pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)NC1=CC=CC(C)=C1 ZHZBZGRSNBXIBX-XJDOXCRVSA-N 0.000 description 1
- IBWOAIHUHHQWTO-LBPRGKRZSA-N (2S)-2-N-(2-hydroxyethyl)-4-methoxyimino-1-N-pentylpyrrolidine-1,2-dicarboxamide Chemical compound CCCCCNC(=O)N1CC(=NOC)C[C@H]1C(=O)NCCO IBWOAIHUHHQWTO-LBPRGKRZSA-N 0.000 description 1
- UABAIRNCPKKQRB-KRWDZBQOSA-N (2S)-2-N-(2-methoxyethyl)-1-N-(3-methoxyphenyl)-4-[(2-methylpropan-2-yl)oxyimino]pyrrolidine-1,2-dicarboxamide Chemical compound COCCNC(=O)[C@@H]1CC(=NOC(C)(C)C)CN1C(=O)NC1=CC=CC(OC)=C1 UABAIRNCPKKQRB-KRWDZBQOSA-N 0.000 description 1
- LDBXSFUUZGPJPG-PMERELPUSA-N (2S)-2-N-(9-ethylcarbazol-3-yl)-1-N-pentyl-4-phenylmethoxyiminopyrrolidine-1,2-dicarboxamide Chemical compound CCCCCNC(=O)N([C@@H](C1)C(=O)NC=2C=C3C4=CC=CC=C4N(CC)C3=CC=2)CC1=NOCC1=CC=CC=C1 LDBXSFUUZGPJPG-PMERELPUSA-N 0.000 description 1
- XILUKNNQMBHDNC-DEOSSOPVSA-N (2S)-2-N-(9-ethylcarbazol-3-yl)-4-methoxyimino-1-N-pentylpyrrolidine-1,2-dicarboxamide Chemical compound CCCCCNC(=O)N1CC(=NOC)C[C@H]1C(=O)NC1=CC=C(N(CC)C=2C3=CC=CC=2)C3=C1 XILUKNNQMBHDNC-DEOSSOPVSA-N 0.000 description 1
- VYULFYVNZYBADO-SANMLTNESA-N (2S)-2-N-benzyl-4-benzylidene-2-N-methyl-1-N-(3-methylphenyl)pyrrolidine-1,2-dicarboxamide Chemical compound O=C([C@H]1N(CC(C1)=CC=1C=CC=CC=1)C(=O)NC=1C=C(C)C=CC=1)N(C)CC1=CC=CC=C1 VYULFYVNZYBADO-SANMLTNESA-N 0.000 description 1
- QEYKKJQOHWJOQN-KRWDZBQOSA-N (2S)-2-N-benzyl-4-methoxyimino-1-N-pentylpyrrolidine-1,2-dicarboxamide Chemical compound CCCCCNC(=O)N1CC(=NOC)C[C@H]1C(=O)NCC1=CC=CC=C1 QEYKKJQOHWJOQN-KRWDZBQOSA-N 0.000 description 1
- CDFPAXQHIQEGIB-FQEVSTJZSA-N (2S)-2-[4-(1,3-benzodioxol-5-ylmethyl)piperazine-1-carbonyl]-4-methoxyimino-N-pentylpyrrolidine-1-carboxamide Chemical compound CCCCCNC(=O)N1CC(=NOC)C[C@H]1C(=O)N1CCN(CC=2C=C3OCOC3=CC=2)CC1 CDFPAXQHIQEGIB-FQEVSTJZSA-N 0.000 description 1
- LGENUJCILYPUNL-LBPRGKRZSA-N (2S)-2-methyl-4-methylidene-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=C)C[C@@]1(C)C(O)=O LGENUJCILYPUNL-LBPRGKRZSA-N 0.000 description 1
- CUZFAPWXYPCCPQ-SANMLTNESA-N (2S)-4-(chloromethylidene)-N-(9-ethylcarbazol-3-yl)-1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=CCl)CN1C(=O)COC1=CC=CC=C1 CUZFAPWXYPCCPQ-SANMLTNESA-N 0.000 description 1
- RELYSOBMJCYDBI-KRWDZBQOSA-N (2S)-4-(chloromethylidene)-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=CCl)CN1 RELYSOBMJCYDBI-KRWDZBQOSA-N 0.000 description 1
- BXNWBKWCOOMUGU-QHCPKHFHSA-N (2S)-4-(chloromethylidene)-N-(naphthalen-1-ylmethyl)-1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NCC=1C2=CC=CC=C2C=CC=1)C(=O)COC1=CC=CC=C1 BXNWBKWCOOMUGU-QHCPKHFHSA-N 0.000 description 1
- KDLFLLAOXJOGIC-YTTGMZPUSA-N (2S)-4-(cyanomethylidene)-N-(9-ethylcarbazol-3-yl)-1-(4-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=CC#N)CN1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 KDLFLLAOXJOGIC-YTTGMZPUSA-N 0.000 description 1
- YNVFLEJCEAXWJB-FQEVSTJZSA-N (2S)-4-(cyanomethylidene)-N-(furan-2-ylmethyl)-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NCC=2OC=CC=2)CC(=CC#N)C1 YNVFLEJCEAXWJB-FQEVSTJZSA-N 0.000 description 1
- ZFQJGQDUCQNBMJ-PMCHYTPCSA-N (2S)-4-(dimethylhydrazinylidene)-N-(2-hydroxy-2-phenylethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NN(C)C)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZFQJGQDUCQNBMJ-PMCHYTPCSA-N 0.000 description 1
- NPNSNUUJITVVCA-INIZCTEOSA-N (2S)-4-[(2-methylpropan-2-yl)oxyimino]-N-(2-pyrrol-1-ylphenyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC(C)(C)C)CN[C@@H]1C(=O)NC1=CC=CC=C1N1C=CC=C1 NPNSNUUJITVVCA-INIZCTEOSA-N 0.000 description 1
- CCUHKGBPYRLJRD-NDEPHWFRSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-1-(2,2-diphenylacetyl)-N-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=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 CCUHKGBPYRLJRD-NDEPHWFRSA-N 0.000 description 1
- WRTJHGQHJKEFIV-DEOSSOPVSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-1-(2-methoxyacetyl)-N-(naphthalen-1-ylmethyl)pyrrolidine-2-carboxamide Chemical compound COCC(=O)N([C@@H](C1)C(=O)NCC=2C3=CC=CC=C3C=CC=2)CC1=NOCC1=CC=C(Cl)C(Cl)=C1 WRTJHGQHJKEFIV-DEOSSOPVSA-N 0.000 description 1
- KZFNNHXVXRCJBT-SFHVURJKSA-N (2S)-4-[(3,4-dichlorophenyl)methoxyimino]-N-(furan-2-ylmethyl)-1-prop-2-enoylpyrrolidine-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CON=C1CN(C(=O)C=C)[C@H](C(=O)NCC=2OC=CC=2)C1 KZFNNHXVXRCJBT-SFHVURJKSA-N 0.000 description 1
- DSXCTVYGHZZKTQ-QHCPKHFHSA-N (2S)-4-[(4-methoxyphenyl)methoxyimino]-N-(3-methylphenyl)-2-(morpholine-4-carbonyl)pyrrolidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CON=C1CN(C(=O)NC=2C=C(C)C=CC=2)[C@H](C(=O)N2CCOCC2)C1 DSXCTVYGHZZKTQ-QHCPKHFHSA-N 0.000 description 1
- GWGBZKYOTDILJU-PMERELPUSA-N (2S)-4-benzylidene-1-[4-(dimethylamino)butanoyl]-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C([C@H](N(C1)C(=O)CCCN(C)C)C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C1=CC1=CC=CC=C1 GWGBZKYOTDILJU-PMERELPUSA-N 0.000 description 1
- XXINCLIJRITIJP-VWLOTQADSA-N (2S)-4-benzylidene-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=CC1=CC=CC=C1 XXINCLIJRITIJP-VWLOTQADSA-N 0.000 description 1
- KFBIKYAXAWYUME-QHCPKHFHSA-N (2S)-4-benzylidene-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C([C@H](NC1)C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C1=CC1=CC=CC=C1 KFBIKYAXAWYUME-QHCPKHFHSA-N 0.000 description 1
- BCACQVKGBBSVOK-KRWDZBQOSA-N (2S)-4-ethoxyimino-1-(2-methoxyacetyl)-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound COCC(=O)N1CC(=NOCC)C[C@H]1C(=O)NC1=CC=C(N=CC=C2)C2=C1 BCACQVKGBBSVOK-KRWDZBQOSA-N 0.000 description 1
- CVSZCMVTGQLJBZ-MHZLTWQESA-N (2S)-4-ethoxyimino-N-(9-ethylcarbazol-3-yl)-1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC)C(=O)NC=1C=C2C3=CC=CC=C3N(CC)C2=CC=1)C(=O)COC1=CC=CC=C1 CVSZCMVTGQLJBZ-MHZLTWQESA-N 0.000 description 1
- FRESNKVFBDHLMQ-YTTGMZPUSA-N (2S)-4-ethoxyimino-N-(9-ethylcarbazol-3-yl)-1-(4-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOCC)C(=O)NC=1C=C2C3=CC=CC=C3N(CC)C2=CC=1)C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 FRESNKVFBDHLMQ-YTTGMZPUSA-N 0.000 description 1
- QZZCJOBLOWFROL-SFHVURJKSA-N (2S)-4-ethoxyimino-N-(9-ethylcarbazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOCC)CN[C@@H]1C(=O)NC1=CC=C(N(CC)C=2C3=CC=CC=2)C3=C1 QZZCJOBLOWFROL-SFHVURJKSA-N 0.000 description 1
- QJIANKRGNBISEJ-UXMRNZNESA-N (2S)-4-hydrazinylidene-N-(2-hydroxy-2-phenylethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NN)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QJIANKRGNBISEJ-UXMRNZNESA-N 0.000 description 1
- FOFZTCNHKOSZDH-QHCPKHFHSA-N (2S)-4-methoxyimino-1-(2-oxo-6-pentylpyran-3-carbonyl)-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NC=2C=C3C=CC=NC3=CC=2)CC(=NOC)C1 FOFZTCNHKOSZDH-QHCPKHFHSA-N 0.000 description 1
- XITNPBZKNRGYFK-NRFANRHFSA-N (2S)-4-methoxyimino-1-(2-phenoxyacetyl)-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)COC1=CC=CC=C1 XITNPBZKNRGYFK-NRFANRHFSA-N 0.000 description 1
- GQOYGLQCRXNIPA-QFIPXVFZSA-N (2S)-4-methoxyimino-1-(4-phenylbenzoyl)-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=C1)=CC=C1C1=CC=CC=C1 GQOYGLQCRXNIPA-QFIPXVFZSA-N 0.000 description 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 description 1
- WHCKSTGSTIIPLS-DEOSSOPVSA-N (2S)-N-(1,3-benzodioxol-5-ylmethyl)-1-(4-cyanobenzoyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(NCC=2C=C3OCOC3=CC=2)=O)C(=NOCC=2C=CC=CC=2)CN1C(=O)C1=CC=C(C#N)C=C1 WHCKSTGSTIIPLS-DEOSSOPVSA-N 0.000 description 1
- STIVORZOCUYCCM-QHCPKHFHSA-N (2S)-N-(2,1,3-benzothiadiazol-4-yl)-1-(4-cyanobenzoyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(NC=2C3=NSN=C3C=CC=2)=O)C(=NOCC=2C=CC=CC=2)CN1C(=O)C1=CC=C(C#N)C=C1 STIVORZOCUYCCM-QHCPKHFHSA-N 0.000 description 1
- RXYGUJQQLMATGZ-QHCPKHFHSA-N (2S)-N-(2,1,3-benzothiadiazol-4-yl)-1-benzoyl-4-[(4-methoxyphenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CON=C1CN(C(=O)C=2C=CC=CC=2)[C@H](C(=O)NC=2C3=NSN=C3C=CC=2)C1 RXYGUJQQLMATGZ-QHCPKHFHSA-N 0.000 description 1
- INKQTSCFQDVUHH-FQEVSTJZSA-N (2S)-N-(2-amino-2-oxoethyl)-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]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)C=C1C INKQTSCFQDVUHH-FQEVSTJZSA-N 0.000 description 1
- SGBAWIAUWQEIIK-IBGZPJMESA-N (2S)-N-(2-amino-2-oxoethyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]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)C=C1 SGBAWIAUWQEIIK-IBGZPJMESA-N 0.000 description 1
- MEHLSZKFQYGWFR-QBHOUYDASA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-[2-methyl-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)C)=CC=C1C1=CC=CC=C1C MEHLSZKFQYGWFR-QBHOUYDASA-N 0.000 description 1
- AZWIHVUPVASMLM-SKCDSABHSA-N (2S)-N-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-[4-(2-methoxyphenyl)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=C1OC AZWIHVUPVASMLM-SKCDSABHSA-N 0.000 description 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 description 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 description 1
- CAOHEJZTHILVNG-IBGZPJMESA-N (2S)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound S1C(CC)=NN=C1NC(=O)[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC(=NOC)C1 CAOHEJZTHILVNG-IBGZPJMESA-N 0.000 description 1
- ARHHOCQENREXLR-MHZLTWQESA-N (2S)-N-(9-ethylcarbazol-3-yl)-1-(2-methoxyacetyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H](N(C1)C(=O)COC)C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C1=NOCC1=CC=CC=C1 ARHHOCQENREXLR-MHZLTWQESA-N 0.000 description 1
- BPXWHEIHWBISLB-YTTGMZPUSA-N (2S)-N-(9-ethylcarbazol-3-yl)-1-(2-phenoxyacetyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=NOCC=2C=CC=CC=2)CN1C(=O)COC1=CC=CC=C1 BPXWHEIHWBISLB-YTTGMZPUSA-N 0.000 description 1
- SUJFCDVHACALGG-QFIPXVFZSA-N (2S)-N-(9-ethylcarbazol-3-yl)-4-methoxyimino-1-(3-oxobutanoyl)pyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=NOC)CN1C(=O)CC(C)=O SUJFCDVHACALGG-QFIPXVFZSA-N 0.000 description 1
- IIMDCIFOCXPBCD-HKBQPEDESA-N (2S)-N-(9-ethylcarbazol-3-yl)-4-methoxyimino-1-(4-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=NOC)CN1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 IIMDCIFOCXPBCD-HKBQPEDESA-N 0.000 description 1
- DVHQHDQRVIHREG-HKBQPEDESA-N (2S)-N-(9-ethylcarbazol-3-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=NOC)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DVHQHDQRVIHREG-HKBQPEDESA-N 0.000 description 1
- PCZXZFXPPMCQFU-KRWDZBQOSA-N (2S)-N-(9-ethylcarbazol-3-yl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=NOC)CN1 PCZXZFXPPMCQFU-KRWDZBQOSA-N 0.000 description 1
- BBOQKFXVHHFSBR-QHCPKHFHSA-N (2S)-N-[(1-hydroxycyclohexyl)methyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC1(O)CCCCC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BBOQKFXVHHFSBR-QHCPKHFHSA-N 0.000 description 1
- CUSSSJCUURTDOI-QTJGBDASSA-N (2S)-N-[(1R,2R)-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-QTJGBDASSA-N 0.000 description 1
- 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 description 1
- DWRDAJNQOZRUFG-AXWOKOBESA-N (2S)-N-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1(=CC=C(C=C1)C(=O)N1[C@@H](CC(C1)=NOC)C(=O)N[C@@H]1[C@H]2CC[C@@H]([C@@H]1CO)C2)C1=CC=CC=C1 DWRDAJNQOZRUFG-AXWOKOBESA-N 0.000 description 1
- LSVVBIZTJCKSIU-SDHOMARFSA-N (2S)-N-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)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=CN=C1 LSVVBIZTJCKSIU-SDHOMARFSA-N 0.000 description 1
- SLFIHQVLZWKTPP-VABKMULXSA-N (2S)-N-[(1S,2S)-2-hydroxycyclohexyl]-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)O)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 SLFIHQVLZWKTPP-VABKMULXSA-N 0.000 description 1
- ZXIURBNCHAKMSU-KJGFFNNUSA-N (2S)-N-[(1S,2S,3R,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N1[C@@H](CC(C1)=NOC)C(=O)N[C@H]1[C@H]2CC[C@@H]([C@H]1CO)C2)C1=CC=CC=C1 ZXIURBNCHAKMSU-KJGFFNNUSA-N 0.000 description 1
- MLMDRTCOOJIVBB-DQEYMECFSA-N (2S)-N-[(2R)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-phenylbenzoyl)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=CC=C1 MLMDRTCOOJIVBB-DQEYMECFSA-N 0.000 description 1
- NSFKWVSPVRDESZ-DEOSSOPVSA-N (2S)-N-[(3,4-dimethoxyphenyl)methyl]-1-(2,2-diphenylacetyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC=1C=C(OC)C(OC)=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 NSFKWVSPVRDESZ-DEOSSOPVSA-N 0.000 description 1
- HPXCJKUENZYEFU-QHCPKHFHSA-N (2S)-N-[(3,4-dimethoxyphenyl)methyl]-4-[(2-methylpropan-2-yl)oxyimino]-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(=NOC(C)(C)C)C1 HPXCJKUENZYEFU-QHCPKHFHSA-N 0.000 description 1
- CNDHWEULBBZNAO-XADRRFQNSA-N (2S)-N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=C(O)C(O)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 CNDHWEULBBZNAO-XADRRFQNSA-N 0.000 description 1
- JWTWAXNSXMTQKC-VWLOTQADSA-N (2S)-N-[2-(diethylamino)ethyl]-1-(2,2-diphenylacetyl)-4-[(2-methylpropan-2-yl)oxyimino]pyrrolidine-2-carboxamide Chemical compound CCN(CC)CCNC(=O)[C@@H]1CC(=NOC(C)(C)C)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JWTWAXNSXMTQKC-VWLOTQADSA-N 0.000 description 1
- CCRFUWAUZKKPFS-PMERELPUSA-N (2S)-N-[2-(diethylamino)ethyl]-1-(2,2-diphenylacetyl)-4-[(4-methoxyphenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCCN(CC)CC)C(=NOCC=2C=CC(OC)=CC=2)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 CCRFUWAUZKKPFS-PMERELPUSA-N 0.000 description 1
- CUNIQSZZZOAODZ-DEOSSOPVSA-N (2S)-N-[2-(diethylamino)ethyl]-1-(2,2-diphenylacetyl)-4-ethoxyiminopyrrolidine-2-carboxamide Chemical compound C1C(=NOCC)C[C@@H](C(=O)NCCN(CC)CC)N1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 CUNIQSZZZOAODZ-DEOSSOPVSA-N 0.000 description 1
- FTZAJESCTKEMEN-QHCPKHFHSA-N (2S)-N-[2-(diethylamino)ethyl]-1-(2,2-diphenylacetyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CCN(CC)CCNC(=O)[C@@H]1CC(=NOC)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 FTZAJESCTKEMEN-QHCPKHFHSA-N 0.000 description 1
- FFBHRLLETLOWDQ-LJAQVGFWSA-N (2S)-N-[2-(diethylamino)ethyl]-1-(4-phenoxybenzoyl)-4-phenylmethoxyiminopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCCN(CC)CC)C(=NOCC=2C=CC=CC=2)CN1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 FFBHRLLETLOWDQ-LJAQVGFWSA-N 0.000 description 1
- CNMSPPBOGPVWRA-QHCPKHFHSA-N (2S)-N-[2-(diethylamino)ethyl]-1-[4-(dimethylamino)butanoyl]-4-[(4-methoxyphenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound C1N(C(=O)CCCN(C)C)[C@H](C(=O)NCCN(CC)CC)CC1=NOCC1=CC=C(OC)C=C1 CNMSPPBOGPVWRA-QHCPKHFHSA-N 0.000 description 1
- UTHVBLSVSRXWIW-LBPRGKRZSA-N (2S)-N-[2-(diethylamino)ethyl]-4-ethoxyiminopyrrolidine-2-carboxamide Chemical compound CCON=C1CN[C@H](C(=O)NCCN(CC)CC)C1 UTHVBLSVSRXWIW-LBPRGKRZSA-N 0.000 description 1
- DACPYHYSSWSYOY-SKCDSABHSA-N (2S)-N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-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)[N+]([O-])=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DACPYHYSSWSYOY-SKCDSABHSA-N 0.000 description 1
- PIKZDPDQPMBMLA-UXMRNZNESA-N (2S)-N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-4-methoxyimino-1-(4-pyridin-2-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC(=CC=1)[N+]([O-])=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=N1 PIKZDPDQPMBMLA-UXMRNZNESA-N 0.000 description 1
- RZCZWWTYJSRSMO-UXMRNZNESA-N (2S)-N-[2-hydroxy-2-(4-nitrophenyl)ethyl]-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)C=1C=CC(=CC=1)[N+]([O-])=O)C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 RZCZWWTYJSRSMO-UXMRNZNESA-N 0.000 description 1
- LQUHLBGYEWYSKW-JVHFYALYSA-N (2S)-N-[2-hydroxy-3-(4-methoxyphenoxy)propyl]-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)COC=1C=CC(OC)=CC=1)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LQUHLBGYEWYSKW-JVHFYALYSA-N 0.000 description 1
- ZYFLZAVECOZWOO-PEFOLFAWSA-N (2S)-N-[2-hydroxy-3-(4-methoxyphenoxy)propyl]-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC(O)COC=1C=CC(OC)=CC=1)C(=O)C(C(=C1)C)=CC=C1C1=CC=CC=C1C ZYFLZAVECOZWOO-PEFOLFAWSA-N 0.000 description 1
- CYLVWUSYYMEUHT-NRFANRHFSA-N (2S)-N-benzyl-1-(2-methoxyacetyl)-4-[(4-methoxyphenyl)methoxyimino]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1CC(CN1C(=O)COC)=NOCC=1C=CC(OC)=CC=1)NCC1=CC=CC=C1 CYLVWUSYYMEUHT-NRFANRHFSA-N 0.000 description 1
- DYAFJTJRXUZGBM-VWLOTQADSA-N (2S)-N-benzyl-4-(chloromethylidene)-N-methyl-1-(4-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CC(C1)=CCl)C(=O)C=1C=CC(OC=2C=CC=CC=2)=CC=1)N(C)CC1=CC=CC=C1 DYAFJTJRXUZGBM-VWLOTQADSA-N 0.000 description 1
- LPFDRTHJHYALQN-IBGZPJMESA-N (2S)-N-cyclopropyl-4-[(2-methylpropan-2-yl)oxyimino]-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NC2CC2)CC(=NOC(C)(C)C)C1 LPFDRTHJHYALQN-IBGZPJMESA-N 0.000 description 1
- ZBHNZCHYRJPIPV-FQEVSTJZSA-N (2S)-N-tert-butyl-4-(chloromethylidene)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound CC(C)(C)NC(=O)[C@@H]1CC(=CCl)CN1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 ZBHNZCHYRJPIPV-FQEVSTJZSA-N 0.000 description 1
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- CKYGSXRXTIKGAJ-SSDOTTSWSA-N (2r)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-oxopyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=O)C[C@@H]1C(O)=O CKYGSXRXTIKGAJ-SSDOTTSWSA-N 0.000 description 1
- AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
- QAAGVYFXQLUTJE-MHZLTWQESA-N (2s)-1-(2,2-diphenylacetyl)-n-(naphthalen-1-ylmethyl)-4-oxopyrrolidine-2-carboxamide Chemical compound C([C@H]1C(NCC=2C3=CC=CC=C3C=CC=2)=O)C(=O)CN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 QAAGVYFXQLUTJE-MHZLTWQESA-N 0.000 description 1
- QMQPZLMVZSUYIS-SANMLTNESA-N (2s)-1-[2-(4-chlorophenoxy)acetyl]-n-(9-ethylcarbazol-3-yl)-4-methylidenepyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=C)CN1C(=O)COC1=CC=C(Cl)C=C1 QMQPZLMVZSUYIS-SANMLTNESA-N 0.000 description 1
- FTJROHHWZYUFNE-DEOSSOPVSA-N (2s)-1-[4-(dimethylamino)butanoyl]-n-(9-ethylcarbazol-3-yl)-4-methylidenepyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=C)CN1C(=O)CCCN(C)C FTJROHHWZYUFNE-DEOSSOPVSA-N 0.000 description 1
- QSMVKDATVLAVEJ-INIZCTEOSA-N (2s)-1-acetyl-4-methylidene-n-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound CC(=O)N1CC(=C)C[C@H]1C(=O)NC1=CC=C(N=CC=C2)C2=C1 QSMVKDATVLAVEJ-INIZCTEOSA-N 0.000 description 1
- KIOMHYSYRBBDAQ-VWLOTQADSA-N (2s)-1-benzoyl-n-(9-ethylcarbazol-3-yl)-4-methylidenepyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=C)CN1C(=O)C1=CC=CC=C1 KIOMHYSYRBBDAQ-VWLOTQADSA-N 0.000 description 1
- SWIZYWRXWBPKGL-QHCPKHFHSA-N (2s)-1-n-(3-methoxyphenyl)-4-methylidene-2-n-(naphthalen-1-ylmethyl)pyrrolidine-1,2-dicarboxamide Chemical compound COC1=CC=CC(NC(=O)N2[C@@H](CC(=C)C2)C(=O)NCC=2C3=CC=CC=C3C=CC=2)=C1 SWIZYWRXWBPKGL-QHCPKHFHSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- KJCBVQZCQZYQMB-AWEZNQCLSA-N (2s)-2-(3-hydroxyazetidine-1-carbonyl)-n-(3-methoxyphenyl)-4-oxopyrrolidine-1-carboxamide Chemical compound COC1=CC=CC(NC(=O)N2[C@@H](CC(=O)C2)C(=O)N2CC(O)C2)=C1 KJCBVQZCQZYQMB-AWEZNQCLSA-N 0.000 description 1
- SZILGJCJFXNDMP-AWEZNQCLSA-N (2s)-2-(3-hydroxyazetidine-1-carbonyl)-n-(3-methylphenyl)-4-oxopyrrolidine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2[C@@H](CC(=O)C2)C(=O)N2CC(O)C2)=C1 SZILGJCJFXNDMP-AWEZNQCLSA-N 0.000 description 1
- NJXPSKGEDSTYJA-NSHDSACASA-N (2s)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-oxopyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=O)C[C@@]1(C)C(O)=O NJXPSKGEDSTYJA-NSHDSACASA-N 0.000 description 1
- GBNJVERFGBGDEF-HNNXBMFYSA-N (2s)-2-n-(2,1,3-benzothiadiazol-4-yl)-1-n-(3,5-dichlorophenyl)-4-oxopyrrolidine-1,2-dicarboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=O)N2[C@@H](CC(=O)C2)C(=O)NC=2C3=NSN=C3C=CC=2)=C1 GBNJVERFGBGDEF-HNNXBMFYSA-N 0.000 description 1
- KBJZBNNDNBXLTP-SANMLTNESA-N (2s)-2-n-(9-ethylcarbazol-3-yl)-1-n-(3-methoxyphenyl)-4-methylidenepyrrolidine-1,2-dicarboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=C)CN1C(=O)NC1=CC=CC(OC)=C1 KBJZBNNDNBXLTP-SANMLTNESA-N 0.000 description 1
- AFHJLZABFWLYLW-VWLOTQADSA-N (2s)-2-n-(9-ethylcarbazol-3-yl)-4-methylidene-1-n-phenylpyrrolidine-1,2-dicarboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=C)CN1C(=O)NC1=CC=CC=C1 AFHJLZABFWLYLW-VWLOTQADSA-N 0.000 description 1
- PJEIRALOTOYWCH-KRWDZBQOSA-N (2s)-2-n-(furan-2-ylmethyl)-1-n-(3-methoxyphenyl)-4-methylidenepyrrolidine-1,2-dicarboxamide Chemical compound COC1=CC=CC(NC(=O)N2[C@@H](CC(=C)C2)C(=O)NCC=2OC=CC=2)=C1 PJEIRALOTOYWCH-KRWDZBQOSA-N 0.000 description 1
- JTTHBZRINFPXPL-DEOSSOPVSA-N (2s)-4-(cyanomethylidene)-n-(9-ethylcarbazol-3-yl)-1-(3-oxobutyl)pyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=CC#N)CN1CCC(C)=O JTTHBZRINFPXPL-DEOSSOPVSA-N 0.000 description 1
- DYPLPCBLTZCURC-QHCPKHFHSA-N (2s)-4-methylidene-1-(2-oxo-6-pentylpyran-3-carbonyl)-n-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound O=C1OC(CCCCC)=CC=C1C(=O)N1[C@H](C(=O)NC=2C=C3C=CC=NC3=CC=2)CC(=C)C1 DYPLPCBLTZCURC-QHCPKHFHSA-N 0.000 description 1
- URZPNNAVZHAZSL-NRFANRHFSA-N (2s)-4-oxo-1-(2-phenoxyacetyl)-n-(2-pyrrol-1-ylphenyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(=O)C1)C(=O)NC=1C(=CC=CC=1)N1C=CC=C1)C(=O)COC1=CC=CC=C1 URZPNNAVZHAZSL-NRFANRHFSA-N 0.000 description 1
- UVVAAWFKQPDFIG-JTQLQIEISA-N (2s)-n-(1,3-benzodioxol-5-ylmethyl)-4-oxopyrrolidine-2-carboxamide Chemical compound C=1C=C2OCOC2=CC=1CNC(=O)[C@@H]1CC(=O)CN1 UVVAAWFKQPDFIG-JTQLQIEISA-N 0.000 description 1
- HMZWEYKUEBPZAE-SKCDSABHSA-N (2s)-n-(2-hydroxy-2-phenylethyl)-4-methylidene-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCC(O)C=2C=CC=CC=2)C(=C)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 HMZWEYKUEBPZAE-SKCDSABHSA-N 0.000 description 1
- PMXSNTFXCBSHSG-NRFANRHFSA-N (2s)-n-(3-amino-3-oxopropyl)-4-methoxyimino-1-[2-methyl-4-(2-methylphenyl)benzoyl]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)C=C1C PMXSNTFXCBSHSG-NRFANRHFSA-N 0.000 description 1
- OGZJYBXEMWMRKA-HKBQPEDESA-N (2s)-n-(9-ethylcarbazol-3-yl)-4-methylidene-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NC=2C=C3C4=CC=CC=C4N(C3=CC=2)CC)C(=C)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OGZJYBXEMWMRKA-HKBQPEDESA-N 0.000 description 1
- GBMBYWGODHEYLR-KRWDZBQOSA-N (2s)-n-(9-ethylcarbazol-3-yl)-4-methylidenepyrrolidine-2-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)[C@@H]1CC(=C)CN1 GBMBYWGODHEYLR-KRWDZBQOSA-N 0.000 description 1
- YSHMVDFCUFLDJU-ZTCOLXNVSA-N (2s)-n-[(1r,2r)-2-(hydroxymethyl)cyclohexyl]-4-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]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=C1OC YSHMVDFCUFLDJU-ZTCOLXNVSA-N 0.000 description 1
- JHGWDCHZOYWRIM-LOSJGSFVSA-N (2s)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(3-phenoxybenzoyl)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=1)=CC=CC=1OC1=CC=CC=C1 JHGWDCHZOYWRIM-LOSJGSFVSA-N 0.000 description 1
- IBXGJPAYWMFXSF-IZZNHLLZSA-N (2s)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]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=CC=C1C IBXGJPAYWMFXSF-IZZNHLLZSA-N 0.000 description 1
- HBGRWFKUQRRAFW-DEOSSOPVSA-N (2s)-n-[(3,4-dimethoxyphenyl)methyl]-4-methylidene-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=O)[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC(=C)C1 HBGRWFKUQRRAFW-DEOSSOPVSA-N 0.000 description 1
- IBXGJPAYWMFXSF-OLFRMSBUSA-N (2s,4e)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C\C(C1)=N/OC)C(=O)NC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C IBXGJPAYWMFXSF-OLFRMSBUSA-N 0.000 description 1
- BENKAPCDIOILGV-RQJHMYQMSA-N (2s,4r)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(O)=O BENKAPCDIOILGV-RQJHMYQMSA-N 0.000 description 1
- DLSSSJJOCVWFHE-VHMJCRPXSA-N (2s,4z)-4-(chloromethylidene)-n-(2-hydroxy-2-phenylethyl)-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C([C@H]1C(=O)NCC(O)C=2C=CC=CC=2)\C(=C\Cl)CN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DLSSSJJOCVWFHE-VHMJCRPXSA-N 0.000 description 1
- CVSZCMVTGQLJBZ-IPTVOOGLSA-N (2s,4z)-4-ethoxyimino-n-(9-ethylcarbazol-3-yl)-1-(2-phenoxyacetyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C/C(C1)=N/OCC)C(=O)NC=1C=C2C3=CC=CC=C3N(CC)C2=CC=1)C(=O)COC1=CC=CC=C1 CVSZCMVTGQLJBZ-IPTVOOGLSA-N 0.000 description 1
- MLMDRTCOOJIVBB-BLLANOOHSA-N (2s,4z)-n-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C/C(C1)=N/OC)C(=O)NCC(O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MLMDRTCOOJIVBB-BLLANOOHSA-N 0.000 description 1
- MLMDRTCOOJIVBB-WBHJWWQVSA-N (2s,4z)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C/C(C1)=N/OC)C(=O)NC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MLMDRTCOOJIVBB-WBHJWWQVSA-N 0.000 description 1
- IBXGJPAYWMFXSF-UEEONYLUSA-N (2s,4z)-n-[(2s)-2-hydroxy-2-phenylethyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](C/C(C1)=N/OC)C(=O)NC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C IBXGJPAYWMFXSF-UEEONYLUSA-N 0.000 description 1
- GWOQSKPMGSGJSZ-KEKNWZKVSA-N (3-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CC(CCC1)O)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1 GWOQSKPMGSGJSZ-KEKNWZKVSA-N 0.000 description 1
- LCKYVNKBDKZNLW-LBAQZLPGSA-N (3-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CC(CCC1)O)C(C1=CC=C(C=C1)C=1C=NC=CC=1)=O LCKYVNKBDKZNLW-LBAQZLPGSA-N 0.000 description 1
- LAYBTWYSLAJUBP-LBAQZLPGSA-N (3-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CC(CCC1)O)C(C1=CC=C(C=C1)C1=CC=NC=C1)=O LAYBTWYSLAJUBP-LBAQZLPGSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- LGIGYOAMFFZLTQ-QHCPKHFHSA-N (4-hydroxypiperidin-1-yl)-[(2s)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidin-2-yl]methanone Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N1CCC(O)CC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C LGIGYOAMFFZLTQ-QHCPKHFHSA-N 0.000 description 1
- HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
- HNGJTIMDNFIMFO-NSHDSACASA-N (5S)-5-(1H-benzimidazol-2-yl)-N-methoxypyrrolidin-3-imine Chemical compound C1C(=NOC)CN[C@@H]1C1=NC2=CC=CC=C2N1 HNGJTIMDNFIMFO-NSHDSACASA-N 0.000 description 1
- IJXJGQCXFSSHNL-QMMMGPOBSA-N (R)-(-)-2-Phenylglycinol Chemical compound OC[C@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-QMMMGPOBSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SFLSHLFXELFNJZ-MRVPVSSYSA-N (S)-noradrenaline Chemical compound NC[C@@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-MRVPVSSYSA-N 0.000 description 1
- QHGUCRYDKWKLMG-MRVPVSSYSA-N (S)-octopamine Chemical compound NC[C@@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-MRVPVSSYSA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- DZOWZBGCZPHHLM-MRVPVSSYSA-N (s)-2-amino-1-(4-nitrophenyl)ethanol Chemical compound NC[C@@H](O)C1=CC=C([N+]([O-])=O)C=C1 DZOWZBGCZPHHLM-MRVPVSSYSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
- AGECZFKPNRSRDG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)piperidine Chemical class C1CC2=CC=CC=C2C1N1CCCCC1 AGECZFKPNRSRDG-UHFFFAOYSA-N 0.000 description 1
- YFHYGCSUMSRZKX-UHFFFAOYSA-N 1-(2-methoxyethyl)pyrrolidine-2-carboxamide Chemical compound COCCN1CCCC1C(N)=O YFHYGCSUMSRZKX-UHFFFAOYSA-N 0.000 description 1
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 1
- IBQMAPSJLHRQPE-UHFFFAOYSA-N 1-(4-(trifluoromethyl)phenyl)piperazine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCNCC1 IBQMAPSJLHRQPE-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- SMDRTEWZGPUDTL-VIFPVBQESA-N 1-O-tert-butyl 2-O-methyl (2S)-4-(chloromethylidene)pyrrolidine-1,2-dicarboxylate Chemical compound COC(=O)[C@@H]1CC(=CCl)CN1C(=O)OC(C)(C)C SMDRTEWZGPUDTL-VIFPVBQESA-N 0.000 description 1
- XQKKHGKWYQBEPH-JTQLQIEISA-N 1-O-tert-butyl 2-O-methyl (2S)-4-(cyanomethylidene)pyrrolidine-1,2-dicarboxylate Chemical compound COC(=O)[C@@H]1CC(=CC#N)CN1C(=O)OC(C)(C)C XQKKHGKWYQBEPH-JTQLQIEISA-N 0.000 description 1
- XDRVPAFZDUSKHO-HNNXBMFYSA-N 1-O-tert-butyl 2-O-methyl (2S)-4-benzylidenepyrrolidine-1,2-dicarboxylate Chemical compound C1N(C(=O)OC(C)(C)C)[C@H](C(=O)OC)CC1=CC1=CC=CC=C1 XDRVPAFZDUSKHO-HNNXBMFYSA-N 0.000 description 1
- KGOQGMGOXVPTIK-LJAQVGFWSA-N 1-[(2S)-4-[(4-methoxyphenyl)methoxyimino]-2-(piperidine-1-carbonyl)pyrrolidin-1-yl]-2,2-diphenylethanone Chemical compound COC1=CC=C(CON=C2CN([C@@H](C2)C(=O)N2CCCCC2)C(C(C2=CC=CC=C2)C2=CC=CC=C2)=O)C=C1 KGOQGMGOXVPTIK-LJAQVGFWSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- FYJFFGBZTCYXIL-IBGZPJMESA-N 1-[4-[(2S)-1-acetyl-4-[(3,4-dichlorophenyl)methoxyimino]pyrrolidine-2-carbonyl]piperazin-1-yl]ethanone Chemical compound ClC=1C=C(CON=C2CN([C@@H](C2)C(=O)N2CCN(CC2)C(C)=O)C(C)=O)C=CC=1Cl FYJFFGBZTCYXIL-IBGZPJMESA-N 0.000 description 1
- BFAQNLRAFSBFGU-UHFFFAOYSA-N 1-amino-1-phenylethanol Chemical compound CC(N)(O)C1=CC=CC=C1 BFAQNLRAFSBFGU-UHFFFAOYSA-N 0.000 description 1
- OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical compound CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 description 1
- UZUMQQZPGOFJBQ-UHFFFAOYSA-N 1-aminopropane-1,2-diol Chemical compound CC(O)C(N)O UZUMQQZPGOFJBQ-UHFFFAOYSA-N 0.000 description 1
- DOGCTUGYGZGSFX-UHFFFAOYSA-N 1-aminopropane-1,3-diol Chemical compound NC(O)CCO DOGCTUGYGZGSFX-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- UZQLBACCROFUKQ-UHFFFAOYSA-N 1-methyl-2-(3-methylphenyl)benzene Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C)=C1 UZQLBACCROFUKQ-UHFFFAOYSA-N 0.000 description 1
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical compound CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-M 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)[O-])C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-M 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
- IKODIMKOCSGKHQ-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1Cl IKODIMKOCSGKHQ-UHFFFAOYSA-N 0.000 description 1
- DRVSVCHLQBNMOS-UHFFFAOYSA-N 2-(2-hydroxy-2-phenylethyl)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound OC(CC1(N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C)C(=O)N)C1=CC=CC=C1 DRVSVCHLQBNMOS-UHFFFAOYSA-N 0.000 description 1
- HRZKQGVTZKXXOY-UHFFFAOYSA-N 2-(3-methylphenyl)pyrrolidine-1,2-dicarboxamide Chemical compound CC1=CC=CC(C2(N(CCC2)C(N)=O)C(N)=O)=C1 HRZKQGVTZKXXOY-UHFFFAOYSA-N 0.000 description 1
- VKRCXDRLQDIOKP-UHFFFAOYSA-N 2-(9-ethylcarbazol-3-yl)-1-N-phenylpyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C1(C(N)=O)CCCN1C(=O)NC1=CC=CC=C1 VKRCXDRLQDIOKP-UHFFFAOYSA-N 0.000 description 1
- MGTPDKRKXIGFFQ-UHFFFAOYSA-N 2-(9-ethylcarbazol-3-yl)-4-methylidenepyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C1(C(N)=O)CC(=C)CN1C(N)=O MGTPDKRKXIGFFQ-UHFFFAOYSA-N 0.000 description 1
- VGXKOUVHTCYTNS-UHFFFAOYSA-N 2-(9-ethylcarbazol-3-yl)pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C1(C(N)=O)CCCN1C(N)=O VGXKOUVHTCYTNS-UHFFFAOYSA-N 0.000 description 1
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- OIPQAKWXFVVEGV-UHFFFAOYSA-N 2-[5-(1h-benzimidazol-2-yl)-1-(4-phenoxybenzoyl)pyrrolidin-3-ylidene]acetonitrile Chemical compound C1C(=CC#N)CC(C=2NC3=CC=CC=C3N=2)N1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 OIPQAKWXFVVEGV-UHFFFAOYSA-N 0.000 description 1
- MPQAQDVYMJKJNL-UHFFFAOYSA-N 2-[5-(1h-benzimidazol-2-yl)-1-(4-phenylbenzoyl)pyrrolidin-3-ylidene]acetonitrile Chemical compound C1C(=CC#N)CC(C=2NC3=CC=CC=C3N=2)N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 MPQAQDVYMJKJNL-UHFFFAOYSA-N 0.000 description 1
- RMCBVIIDJGEJGK-NRFANRHFSA-N 2-[[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carbonyl]amino]ethyl acetate Chemical compound C(C)(=O)OCCNC(=O)[C@H]1N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1 RMCBVIIDJGEJGK-NRFANRHFSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 1
- PZSISEFPCYMBDL-UHFFFAOYSA-N 2-bromo-3-methylpyridine Chemical compound CC1=CC=CN=C1Br PZSISEFPCYMBDL-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
- ZRVFFIXOCFUHDA-UHFFFAOYSA-N 2-ethoxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(OCC)=CC=C21 ZRVFFIXOCFUHDA-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- VNLPFGAPKAMFHU-UHFFFAOYSA-N 2-methyl-1,4-diphenylbenzene Chemical compound CC1=CC(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 VNLPFGAPKAMFHU-UHFFFAOYSA-N 0.000 description 1
- CAHIDRFUQUEUTR-UHFFFAOYSA-N 2-methyl-4-phenylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C=CC=CC=2)=C1 CAHIDRFUQUEUTR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- PFXXTYUSZRFQHC-UHFFFAOYSA-N 2-methylhept-5-enamide Chemical compound CC=CCCC(C)C(N)=O PFXXTYUSZRFQHC-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- NYCDSJNKGZMFSX-UHFFFAOYSA-N 2-oxo-6-pentylpyran-3-carboxylic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C(=O)O1 NYCDSJNKGZMFSX-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- BMGKQFRMINVVPP-UHFFFAOYSA-N 2-phenoxybenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1 BMGKQFRMINVVPP-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- JOJLUWNGHIPESK-UHFFFAOYSA-N 2-quinolin-6-ylpyrrolidine-1,2-dicarboxamide Chemical compound NC(=O)N1CCCC1(C(N)=O)C1=CC=C(N=CC=C2)C2=C1 JOJLUWNGHIPESK-UHFFFAOYSA-N 0.000 description 1
- AKTBLLITNRMZEJ-UHFFFAOYSA-N 2H-pyran-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=COC1 AKTBLLITNRMZEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- LRCXRAABFLIVAI-QMMMGPOBSA-N 3-[(1r)-2-amino-1-hydroxyethyl]phenol Chemical compound NC[C@H](O)C1=CC=CC(O)=C1 LRCXRAABFLIVAI-QMMMGPOBSA-N 0.000 description 1
- XXYMESKLCDKHKY-PMERELPUSA-N 3-[(2S)-2-[4-(3,4-dichlorophenyl)piperazine-1-carbonyl]-4-phenylmethoxyiminopyrrolidine-1-carbonyl]-6-pentylpyran-2-one Chemical compound C(C1=CC=CC=C1)ON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)C1=CC(=C(C=C1)Cl)Cl)C(=O)C=1C(OC(=CC=1)CCCCC)=O XXYMESKLCDKHKY-PMERELPUSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- FQMNGDVIZAQQLT-UHFFFAOYSA-N 3-iminopyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1NCCC1=N FQMNGDVIZAQQLT-UHFFFAOYSA-N 0.000 description 1
- ITLWSYAJGXPQSO-UHFFFAOYSA-N 3-methyl-4-phenylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 ITLWSYAJGXPQSO-UHFFFAOYSA-N 0.000 description 1
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 description 1
- XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 description 1
- GBCYLZKFDBVTNN-UHFFFAOYSA-N 3-piperidin-1-yl-2h-1,2-benzoxazine Chemical class C1CCCCN1C1=CC2=CC=CC=C2ON1 GBCYLZKFDBVTNN-UHFFFAOYSA-N 0.000 description 1
- OTZSTWZWLJLAAB-UHFFFAOYSA-N 4-(1-oxidopyridin-1-ium-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=[N+]1[O-] OTZSTWZWLJLAAB-UHFFFAOYSA-N 0.000 description 1
- DGHGRAZWNAQANC-UHFFFAOYSA-N 4-(2,4-difluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1F DGHGRAZWNAQANC-UHFFFAOYSA-N 0.000 description 1
- AOTYKBXXCYCXRZ-UHFFFAOYSA-N 4-(2-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1Cl AOTYKBXXCYCXRZ-UHFFFAOYSA-N 0.000 description 1
- NVYOOVLWXDVFAA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C(Cl)=C1 NVYOOVLWXDVFAA-UHFFFAOYSA-N 0.000 description 1
- SJIVTXJWSYIMDG-UHFFFAOYSA-N 4-(3-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1 SJIVTXJWSYIMDG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OAMJQKDGQYAQKD-UHFFFAOYSA-N 4-(3-methoxyphenyl)benzoic acid Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C(O)=O)=C1 OAMJQKDGQYAQKD-UHFFFAOYSA-N 0.000 description 1
- FIMRRWLTRBEAOM-UHFFFAOYSA-N 4-(4-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 FIMRRWLTRBEAOM-UHFFFAOYSA-N 0.000 description 1
- FDPKGXQCDURRBM-UHFFFAOYSA-N 4-(4-methoxyphenyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 FDPKGXQCDURRBM-UHFFFAOYSA-N 0.000 description 1
- RZOCCLOTCXINRG-UHFFFAOYSA-N 4-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 RZOCCLOTCXINRG-UHFFFAOYSA-N 0.000 description 1
- LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 description 1
- ZSSWTOFPKWLLQV-HNNXBMFYSA-N 4-(dimethylamino)-1-[(2S)-4-methoxyimino-2-(piperidine-1-carbonyl)pyrrolidin-1-yl]butan-1-one Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCCCC1)C(CCCN(C)C)=O ZSSWTOFPKWLLQV-HNNXBMFYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- WQKDEUGMDSTMAK-UHFFFAOYSA-N 4-[2-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C(F)(F)F WQKDEUGMDSTMAK-UHFFFAOYSA-N 0.000 description 1
- LFMPHDUPXVEMAB-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 LFMPHDUPXVEMAB-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 1
- RAFOEQLLARZUAM-UHFFFAOYSA-N 4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CON=C1CNC(C(N)=O)C1 RAFOEQLLARZUAM-UHFFFAOYSA-N 0.000 description 1
- CCBKADQVSXLSDN-UHFFFAOYSA-N 4-pyrimidin-5-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=CN=C1 CCBKADQVSXLSDN-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- UNQYAAAWKOOBFQ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C=2C(=O)N(CCCO)C(=O)N(C)C=2N=C1OC1=CC=C(Cl)C(OC(F)(F)F)=C1 UNQYAAAWKOOBFQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QZNZQHBVXQCBPS-UHFFFAOYSA-N C(=O)=C1C(NCC1=NOC)C(=O)N Chemical compound C(=O)=C1C(NCC1=NOC)C(=O)N QZNZQHBVXQCBPS-UHFFFAOYSA-N 0.000 description 1
- YBEQVEBUALANIR-VWLOTQADSA-N C1=C(OC)C(OC)=CC=C1CNC(=O)[C@H](C1)N(C(=O)COC=2C=CC(Cl)=CC=2)CC1=CC1=CC=CC=C1 Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=O)[C@H](C1)N(C(=O)COC=2C=CC(Cl)=CC=2)CC1=CC1=CC=CC=C1 YBEQVEBUALANIR-VWLOTQADSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- SITGOFJJJSDQOL-UHFFFAOYSA-N ClC(=O)C(=O)c1ccc(cc1)-c1ccccc1 Chemical compound ClC(=O)C(=O)c1ccc(cc1)-c1ccccc1 SITGOFJJJSDQOL-UHFFFAOYSA-N 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000007698 E/Z-isomerization reaction Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- SGLQCPNIRBRZII-UHFFFAOYSA-N N=1SN=C2C1C=CC=C2C2(N(CC(C2)=NOCC2=CC=CC=C2)C(=O)NC2=CC=CC=C2)C(=O)N Chemical compound N=1SN=C2C1C=CC=C2C2(N(CC(C2)=NOCC2=CC=CC=C2)C(=O)NC2=CC=CC=C2)C(=O)N SGLQCPNIRBRZII-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 101710103206 Oxytocin receptor Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 101000986756 Rattus norvegicus Oxytocin receptor Proteins 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010046797 Uterine ischaemia Diseases 0.000 description 1
- 102000004136 Vasopressin Receptors Human genes 0.000 description 1
- 108090000643 Vasopressin Receptors Proteins 0.000 description 1
- 108010046516 Wheat Germ Agglutinins Proteins 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- QGMMKSUHQMVLRO-VGRMVHKJSA-N [(1r,2s,3r,4s)-3-amino-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1C[C@@]2([H])[C@H](CO)[C@H](N)[C@]1([H])C2 QGMMKSUHQMVLRO-VGRMVHKJSA-N 0.000 description 1
- GCWPGEWXYDEQAY-RNFRBKRXSA-N [(1s,2r)-2-aminocyclohexyl]methanol Chemical compound N[C@@H]1CCCC[C@@H]1CO GCWPGEWXYDEQAY-RNFRBKRXSA-N 0.000 description 1
- LMLIZYRZINNREE-QHCPKHFHSA-N [(2S)-1-[4-(3,4-dichlorophenyl)benzoyl]-4-methoxyiminopyrrolidin-2-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)CCO)C(=O)C1=CC=C(C=C1)C1=CC(=C(C=C1)Cl)Cl LMLIZYRZINNREE-QHCPKHFHSA-N 0.000 description 1
- QBXSMAPFDIXJKJ-NDEPHWFRSA-N [(2S)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidin-2-yl]-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)C1=CC=C(C=C1)C(F)(F)F)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C QBXSMAPFDIXJKJ-NDEPHWFRSA-N 0.000 description 1
- RDJRQYYKAIQIFM-MHZLTWQESA-N [4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-[(2S)-1-benzoyl-4-[(3,4-dichlorophenyl)methoxyimino]pyrrolidin-2-yl]methanone Chemical compound ClC=1C=C(CON=C2CN([C@@H](C2)C(=O)N2CCN(CC2)CC2=CC3=C(OCO3)C=C2)C(C2=CC=CC=C2)=O)C=CC=1Cl RDJRQYYKAIQIFM-MHZLTWQESA-N 0.000 description 1
- PZRPBPMLSSNFOM-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=C(B(O)O)C=C1 PZRPBPMLSSNFOM-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- VWXRQYYUEIYXCZ-OBIMUBPZSA-N atosiban Chemical compound C1=CC(OCC)=CC=C1C[C@@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)CSSCCC(=O)N1 VWXRQYYUEIYXCZ-OBIMUBPZSA-N 0.000 description 1
- 229960002403 atosiban Drugs 0.000 description 1
- 108700007535 atosiban Proteins 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000011128 cardiac conduction Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- YMNRWRKDEPEIAQ-UHFFFAOYSA-M chloromethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCl)C1=CC=CC=C1 YMNRWRKDEPEIAQ-UHFFFAOYSA-M 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009989 contractile response Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- UTVVREMVDJTZAC-UHFFFAOYSA-N furan-2-amine Chemical compound NC1=CC=CO1 UTVVREMVDJTZAC-UHFFFAOYSA-N 0.000 description 1
- 150000002244 furazanes Chemical class 0.000 description 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- IWCAQTQMDRGMPI-UHFFFAOYSA-N hexane-3,4-diamine Chemical compound CCC(N)C(N)CC IWCAQTQMDRGMPI-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RAWNCEVMALXUIW-UHFFFAOYSA-N n-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound C=1C=C2N=CC=CC2=CC=1NC(=O)C1CCCN1 RAWNCEVMALXUIW-UHFFFAOYSA-N 0.000 description 1
- AEMBWNDIEFEPTH-UHFFFAOYSA-N n-tert-butyl-n-ethylnitrous amide Chemical compound CCN(N=O)C(C)(C)C AEMBWNDIEFEPTH-UHFFFAOYSA-N 0.000 description 1
- VACPZDQXUAOTFR-UHFFFAOYSA-N n-tert-butylbutan-1-amine Chemical compound CCCCNC(C)(C)C VACPZDQXUAOTFR-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N noradrenaline Chemical compound NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- VYCHJEXJHFTAQI-UHFFFAOYSA-N o-prop-2-enylhydroxylamine;hydrate;hydrochloride Chemical compound O.Cl.NOCC=C VYCHJEXJHFTAQI-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 239000012026 peptide coupling reagents Substances 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 108091005465 peptide hormone receptors Proteins 0.000 description 1
- 102000014187 peptide receptors Human genes 0.000 description 1
- 230000009984 peri-natal effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 231100000857 poor renal function Toxicity 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- JVHTULHHEREUQQ-IBGZPJMESA-N tert-butyl 3-[[(2S)-1-acetyl-4-benzylidenepyrrolidine-2-carbonyl]amino]azetidine-1-carboxylate Chemical compound C(C)(=O)N1[C@@H](CC(C1)=CC1=CC=CC=C1)C(=O)NC1CN(C1)C(=O)OC(C)(C)C JVHTULHHEREUQQ-IBGZPJMESA-N 0.000 description 1
- BRHRQXCINXUHBG-NRFANRHFSA-N tert-butyl 3-[[(2S)-4-ethoxyimino-1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carbonyl]amino]azetidine-1-carboxylate Chemical compound C(C)ON=C1C[C@H](N(C1)C(=O)C=1C(OC(=CC=1)CCCCC)=O)C(=O)NC1CN(C1)C(=O)OC(C)(C)C BRHRQXCINXUHBG-NRFANRHFSA-N 0.000 description 1
- AQGQBBHXLMABCH-UHFFFAOYSA-N tert-butyl 3-[[4-methylidene-1-(pentylcarbamoyl)pyrrolidine-2-carbonyl]amino]azetidine-1-carboxylate Chemical compound CCCCCNC(=O)N1CC(=C)CC1C(=O)NC1CN(C(=O)OC(C)(C)C)C1 AQGQBBHXLMABCH-UHFFFAOYSA-N 0.000 description 1
- IYRULVWLVRRRIS-UHFFFAOYSA-N tert-butyl 3-amino-2-hydroxypropanoate Chemical compound CC(C)(C)OC(=O)C(O)CN IYRULVWLVRRRIS-UHFFFAOYSA-N 0.000 description 1
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000001349 uterorelaxant effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- 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
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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
- C07D403/02—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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/02—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
- 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
- C07D405/14—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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pregnancy & Childbirth (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 |
Family
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 (sh) |
EP (1) | EP1268419B1 (sh) |
JP (2) | JP2003528854A (sh) |
KR (1) | KR100714585B1 (sh) |
CN (1) | CN1296354C (sh) |
AR (1) | AR029499A1 (sh) |
AT (1) | ATE330940T1 (sh) |
AU (2) | AU5620901A (sh) |
BG (1) | BG107132A (sh) |
BR (1) | BR0109900A (sh) |
CA (1) | CA2401242A1 (sh) |
CY (1) | CY1105519T1 (sh) |
CZ (1) | CZ20023243A3 (sh) |
DE (1) | DE60120940T2 (sh) |
DK (1) | DK1268419T3 (sh) |
EA (1) | EA006424B1 (sh) |
EE (1) | EE200200555A (sh) |
ES (1) | ES2261404T3 (sh) |
HK (1) | HK1054031B (sh) |
HR (1) | HRP20020705A2 (sh) |
HU (1) | HUP0300994A2 (sh) |
IL (1) | IL151912A0 (sh) |
MX (1) | MXPA02009382A (sh) |
NO (1) | NO323969B1 (sh) |
NZ (1) | NZ521060A (sh) |
PL (1) | PL358001A1 (sh) |
PT (1) | PT1268419E (sh) |
SI (1) | SI1268419T1 (sh) |
SK (1) | SK13832002A3 (sh) |
UA (1) | UA74362C2 (sh) |
WO (1) | WO2001072705A1 (sh) |
YU (1) | YU73502A (sh) |
ZA (1) | ZA200206799B (sh) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1268418B1 (en) * | 2000-03-27 | 2006-06-14 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active pyrrolidine derivatives as bax inhibitors |
SK15552003A3 (sk) * | 2001-06-18 | 2004-05-04 | Applied Research Systems Ars Holding N. V. | Oxadiazolové a tiadiazolové deriváty pyrolidínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie |
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 |
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 |
US7820702B2 (en) | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
KR20060124775A (ko) * | 2004-02-26 | 2006-12-05 | 어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이. | 피롤리딘 옥심의 제조방법 |
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 |
WO2013042782A1 (ja) | 2011-09-22 | 2013-03-28 | 武田薬品工業株式会社 | 縮合複素環化合物 |
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 |
CA2953722C (en) | 2014-07-02 | 2022-09-13 | ObsEva SA | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime, and methods of using the same |
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 |
CA2210138A1 (en) | 1995-01-24 | 1996-08-01 | Peter D. Williams | Tocolytic oxytocin receptor antagonists |
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 |
US6235755B1 (en) * | 1998-08-07 | 2001-05-22 | Applied Research Systems Ars Holding N.A. | FSH mimetics for the treatment of infertility |
SK10742001A3 (sk) * | 1999-01-27 | 2002-08-06 | Ortho-Mcneil Pharmaceutical, Inc. | Peptidylové heterocyklické ketóny použiteľné ako inhibítory tryptázy |
EP1158996A4 (en) * | 1999-02-18 | 2005-01-12 | Kaken Pharma Co Ltd | NEW AMID DERIVATIVES AS GROWTH HORMONE SECRETION CONVEYORS |
IL145429A0 (en) * | 1999-03-15 | 2002-06-30 | Axys Pharm Inc | N-cyanomethyl amides, processes for the preparation thereof and pharmaceutical compositions containing the same |
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 |
EP1268418B1 (en) * | 2000-03-27 | 2006-06-14 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active pyrrolidine derivatives as bax inhibitors |
-
2001
- 2001-03-20 AU AU5620901A patent/AU5620901A/xx active Pending
- 2001-03-20 UA UA2002097675A patent/UA74362C2/uk unknown
- 2001-03-20 IL IL15191201A patent/IL151912A0/xx unknown
- 2001-03-20 HU HU0300994A patent/HUP0300994A2/hu unknown
- 2001-03-20 CA CA002401242A patent/CA2401242A1/en not_active Abandoned
- 2001-03-20 PL PL01358001A patent/PL358001A1/xx not_active Application Discontinuation
- 2001-03-20 CZ CZ20023243A patent/CZ20023243A3/cs unknown
- 2001-03-20 EP EP01929439A patent/EP1268419B1/en not_active Expired - Lifetime
- 2001-03-20 WO PCT/EP2001/003171 patent/WO2001072705A1/en not_active Application Discontinuation
- 2001-03-20 CN CNB018071767A patent/CN1296354C/zh not_active Expired - Fee Related
- 2001-03-20 BR BR0109900-0A patent/BR0109900A/pt not_active IP Right Cessation
- 2001-03-20 SI SI200130566T patent/SI1268419T1/sl unknown
- 2001-03-20 EA EA200201026A patent/EA006424B1/ru unknown
- 2001-03-20 US US10/239,912 patent/US7211601B2/en not_active Expired - Fee Related
- 2001-03-20 MX MXPA02009382A patent/MXPA02009382A/es active IP Right Grant
- 2001-03-20 PT PT01929439T patent/PT1268419E/pt unknown
- 2001-03-20 AU AU2001256209A patent/AU2001256209B2/en not_active Ceased
- 2001-03-20 KR KR1020027012744A patent/KR100714585B1/ko not_active IP Right Cessation
- 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 AT AT01929439T patent/ATE330940T1/de not_active IP Right Cessation
- 2001-03-20 ES ES01929439T patent/ES2261404T3/es not_active Expired - Lifetime
- 2001-03-20 NZ NZ521060A patent/NZ521060A/en unknown
- 2001-03-20 EE EEP200200555A patent/EE200200555A/xx unknown
- 2001-03-20 YU YU73502A patent/YU73502A/sh unknown
- 2001-03-20 DK DK01929439T patent/DK1268419T3/da active
- 2001-03-20 JP JP2001570618A patent/JP2003528854A/ja not_active Withdrawn
- 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
-
2012
- 2012-05-09 JP JP2012107898A patent/JP5580364B2/ja not_active Expired - Fee Related
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SK13832002A3 (sk) | Pyrolidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie | |
JP4853965B2 (ja) | アダマンタン誘導体およびアザビシクロオクタン誘導体およびアザビシクロノナン誘導体、ならびにこれらの調製方法およびdpp−iv阻害剤としてのこれらの使用 | |
EP1812405A1 (de) | Neue bradykinin-b1-antagonisten, verfahren zu deren herstellung sowie deren verwendung als arzneimittel | |
JP4075064B2 (ja) | 4,4−ジフルオロ−1,2,3,4−テトラヒドロ−5h−1−ベンゾアゼピン誘導体又はその塩 | |
JP2013545740A (ja) | バニロイド受容体リガンドとしての置換された複素芳香族カルボキサミド誘導体および尿素誘導体 | |
KR20030026979A (ko) | 디시아노피리딘 유도체를 포함하는 의약 | |
CA2548849A1 (en) | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease | |
AU2001256209A1 (en) | Pharmaceutically active pyrrolidine derivatives | |
JP4511184B2 (ja) | オキシトシン・アンタゴニストとしてのトリアゾール類 | |
JP4426284B2 (ja) | ピロリジン・オキサジアゾール−及びチアジアゾール誘導体 | |
ES2392978T3 (es) | Agentes del receptor H3 de histamina, preparación y usos terapéuticos | |
JP4851085B2 (ja) | オキシトシン拮抗物質としてのピロリジン誘導体 | |
JP4350948B2 (ja) | オキシトシン調節活性を有するピロリジンエステル誘導体 | |
JP2006117568A (ja) | チオフェン環を有する新規アミド誘導体及びその医薬としての用途 | |
JP4773335B2 (ja) | 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 | |
NZ786241A (en) | 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists | |
MXPA01005034A (en) | Pyrrolidine derivatives-ccr-3 receptor antagonists |