SK80899A3 - Sulphonamide derivatives, process for their preparation, and their use as medicaments - Google Patents
Sulphonamide derivatives, process for their preparation, and their use as medicaments Download PDFInfo
- Publication number
- SK80899A3 SK80899A3 SK808-99A SK80899A SK80899A3 SK 80899 A3 SK80899 A3 SK 80899A3 SK 80899 A SK80899 A SK 80899A SK 80899 A3 SK80899 A3 SK 80899A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methoxy
- phenyl
- methylpiperazin
- benzenesulfonamide
- chloro
- Prior art date
Links
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 16
- 239000003814 drug Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 101
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 51
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000001408 amides Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 229940124530 sulfonamide Drugs 0.000 claims description 18
- JLTUANWNGKWRQO-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonyl chloride Chemical group C1=C(Cl)C=C2C(C)=C(S(Cl)(=O)=O)SC2=C1 JLTUANWNGKWRQO-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- ZFZRYSSNJATGEN-UHFFFAOYSA-N 2,3-dichloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZFZRYSSNJATGEN-UHFFFAOYSA-N 0.000 claims description 6
- PBIXGKIJQUGWAZ-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-ylaniline Chemical compound COC1=CC=C(N)C=C1N1CCNCC1 PBIXGKIJQUGWAZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- GXWGRQOMOLFZDN-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonic acid Chemical compound C1=C(Cl)C=C2C(C)=C(S(O)(=O)=O)SC2=C1 GXWGRQOMOLFZDN-UHFFFAOYSA-N 0.000 claims description 5
- LVFWTBJPVUYJFU-UHFFFAOYSA-N 5-iodo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(I)=CC=C1C LVFWTBJPVUYJFU-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- LILAGPSTPBGPKR-UHFFFAOYSA-N 2,5-dichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)thiophene-3-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl LILAGPSTPBGPKR-UHFFFAOYSA-N 0.000 claims description 4
- GZBPVVJNBJRWDU-UHFFFAOYSA-N 2,5-dimethoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=C(C(OC)=CC=2)N2CCN(C)CC2)=C1 GZBPVVJNBJRWDU-UHFFFAOYSA-N 0.000 claims description 4
- VMSDCTMEXGQPAB-UHFFFAOYSA-N 2-chloro-4-fluoro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl VMSDCTMEXGQPAB-UHFFFAOYSA-N 0.000 claims description 4
- OVRVKGKPURKVHI-UHFFFAOYSA-N 2-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1Cl OVRVKGKPURKVHI-UHFFFAOYSA-N 0.000 claims description 4
- LBGJGZQLAGBTQV-UHFFFAOYSA-N 3,4-dichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 LBGJGZQLAGBTQV-UHFFFAOYSA-N 0.000 claims description 4
- MIYNDVOEMLLEQH-UHFFFAOYSA-N 3,4-dichloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MIYNDVOEMLLEQH-UHFFFAOYSA-N 0.000 claims description 4
- UDJMZYLDIFOZMO-UHFFFAOYSA-N 3,5-dichloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 UDJMZYLDIFOZMO-UHFFFAOYSA-N 0.000 claims description 4
- TXBZLOLLOHEAOS-UHFFFAOYSA-N 3,5-dichloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 TXBZLOLLOHEAOS-UHFFFAOYSA-N 0.000 claims description 4
- FGKOHVCNMZHHPT-UHFFFAOYSA-N 3-bromo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Br)=C1 FGKOHVCNMZHHPT-UHFFFAOYSA-N 0.000 claims description 4
- FPCXZHNKUCICKB-UHFFFAOYSA-N 3-bromo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Br)=C1 FPCXZHNKUCICKB-UHFFFAOYSA-N 0.000 claims description 4
- RUWCPIWOUKKUHW-UHFFFAOYSA-N 3-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C(Cl)=C1 RUWCPIWOUKKUHW-UHFFFAOYSA-N 0.000 claims description 4
- CNIJKPUBLUZAPL-UHFFFAOYSA-N 3-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C CNIJKPUBLUZAPL-UHFFFAOYSA-N 0.000 claims description 4
- ZPMXLMGYUMUHFY-UHFFFAOYSA-N 3-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 ZPMXLMGYUMUHFY-UHFFFAOYSA-N 0.000 claims description 4
- JVMYDAKCSRHLEK-UHFFFAOYSA-N 3-iodo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C(I)=C1 JVMYDAKCSRHLEK-UHFFFAOYSA-N 0.000 claims description 4
- SCIAZBXOVPXAAS-UHFFFAOYSA-N 3-iodo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(I)=C1 SCIAZBXOVPXAAS-UHFFFAOYSA-N 0.000 claims description 4
- OZYPUQNRUYTZDI-UHFFFAOYSA-N 4-bromo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 OZYPUQNRUYTZDI-UHFFFAOYSA-N 0.000 claims description 4
- KDWOPRGKLIGEMV-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3-nitrobenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 KDWOPRGKLIGEMV-UHFFFAOYSA-N 0.000 claims description 4
- FRASUHRYTBHUSF-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 FRASUHRYTBHUSF-UHFFFAOYSA-N 0.000 claims description 4
- XXNCVBPTKUKJQA-UHFFFAOYSA-N 4-ethyl-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 XXNCVBPTKUKJQA-UHFFFAOYSA-N 0.000 claims description 4
- IHSKRXGUPGHJRL-UHFFFAOYSA-N 4-fluoro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 IHSKRXGUPGHJRL-UHFFFAOYSA-N 0.000 claims description 4
- BDHMSYNBSBZCAF-UHFFFAOYSA-N 4-iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(I)C=C1 BDHMSYNBSBZCAF-UHFFFAOYSA-N 0.000 claims description 4
- MWNFFPVWBIUIPM-UHFFFAOYSA-N 4-iodo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(I)C=C1 MWNFFPVWBIUIPM-UHFFFAOYSA-N 0.000 claims description 4
- GRTSLVZCKXCJSA-UHFFFAOYSA-N 4-methoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(OC)C(N2CCN(C)CC2)=C1 GRTSLVZCKXCJSA-UHFFFAOYSA-N 0.000 claims description 4
- HUJQYGNBKNUWRN-UHFFFAOYSA-N 5-(dimethylamino)-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)C=C1N1CCN(C)CC1 HUJQYGNBKNUWRN-UHFFFAOYSA-N 0.000 claims description 4
- FKHDVURVQRRQMC-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1OC FKHDVURVQRRQMC-UHFFFAOYSA-N 0.000 claims description 4
- SEVUMFHPPTVQFK-UHFFFAOYSA-N 5-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)-2-methyl-1-benzothiophene-3-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC(Cl)=CC=C3SC=2C)C=C1N1CCNCC1 SEVUMFHPPTVQFK-UHFFFAOYSA-N 0.000 claims description 4
- OPAGNFGYYZRBMY-UHFFFAOYSA-N 5-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC(Cl)=C3C=CC=2)C=C1N1CCNCC1 OPAGNFGYYZRBMY-UHFFFAOYSA-N 0.000 claims description 4
- RGYOLLJNULUYJC-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]thiophene-2-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)S1 RGYOLLJNULUYJC-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- JFMMPPFFKNAFCU-UHFFFAOYSA-N n-(4-methoxy-3-piperazin-1-ylphenyl)-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C=1C(C)=NOC=1C JFMMPPFFKNAFCU-UHFFFAOYSA-N 0.000 claims description 4
- SPWDRGXBRZSIHU-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2,1,3-benzothiadiazole-4-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=NSN=C3C=CC=2)C=C1N1CCN(C)CC1 SPWDRGXBRZSIHU-UHFFFAOYSA-N 0.000 claims description 4
- CGHDYVWGLJASRY-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2-methyl-5-nitrobenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C CGHDYVWGLJASRY-UHFFFAOYSA-N 0.000 claims description 4
- NFDULIOCPNFQTF-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C=1C(C)=NOC=1C NFDULIOCPNFQTF-UHFFFAOYSA-N 0.000 claims description 4
- OWOHQAJEJVZGKC-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 OWOHQAJEJVZGKC-UHFFFAOYSA-N 0.000 claims description 4
- UWMHQNBQRWMRIX-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1 UWMHQNBQRWMRIX-UHFFFAOYSA-N 0.000 claims description 4
- WEEWKDWGTHHXGC-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-1-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C=C1N1CCN(C)CC1 WEEWKDWGTHHXGC-UHFFFAOYSA-N 0.000 claims description 4
- UREUVCXONTWIPA-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphthalene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C=C1N1CCN(C)CC1 UREUVCXONTWIPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- GTYQRUMJFLZBJP-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-5-methoxy-4-(4-methylpiperazin-1-yl)-2,3-dihydroindole;hydrochloride Chemical compound Cl.COC1=CC=C2N(S(=O)(=O)C3=C(C4=CC(Cl)=CC=C4S3)C)CCC2=C1N1CCN(C)CC1 GTYQRUMJFLZBJP-UHFFFAOYSA-N 0.000 claims description 3
- PAVQGEMIVJDBJU-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-5-methoxy-6-(4-methylpiperazin-1-yl)-2,3-dihydroindole Chemical compound COC1=CC=2CCN(S(=O)(=O)C3=C(C4=CC(Cl)=CC=C4S3)C)C=2C=C1N1CCN(C)CC1 PAVQGEMIVJDBJU-UHFFFAOYSA-N 0.000 claims description 3
- SJMBDQZKEQESDI-UHFFFAOYSA-N 2-bromo-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC=C1Br SJMBDQZKEQESDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- XWZKCRAOVMNSDF-UHFFFAOYSA-N 3,4-difluoro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1 XWZKCRAOVMNSDF-UHFFFAOYSA-N 0.000 claims description 3
- MVUZJBJKISRFBE-UHFFFAOYSA-N 3-[4-(cyclopropylmethyl)piperazin-1-yl]-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1N1CCN(CC2CC2)CC1 MVUZJBJKISRFBE-UHFFFAOYSA-N 0.000 claims description 3
- VIOUGUUYIYJHFB-UHFFFAOYSA-N 3-chloro-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 VIOUGUUYIYJHFB-UHFFFAOYSA-N 0.000 claims description 3
- FOJBAYHRQHCRAZ-UHFFFAOYSA-N 3-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C(Cl)=C1 FOJBAYHRQHCRAZ-UHFFFAOYSA-N 0.000 claims description 3
- NHCPWIQLVKLJSJ-UHFFFAOYSA-N 4-bromo-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 NHCPWIQLVKLJSJ-UHFFFAOYSA-N 0.000 claims description 3
- UTVBHODAPYYDFB-UHFFFAOYSA-N 4-chloro-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-2,5-dimethylbenzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC(C)=C(Cl)C=C1C UTVBHODAPYYDFB-UHFFFAOYSA-N 0.000 claims description 3
- NGRRREPRVBZRID-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)aniline Chemical compound COC1=CC=C(N)C=C1N1CCN(C)CC1 NGRRREPRVBZRID-UHFFFAOYSA-N 0.000 claims description 3
- VYYJRKSNFZQLMV-UHFFFAOYSA-N 4-tert-butyl-n-(4-methoxy-3-piperazin-1-ylphenyl)benzenesulfonamide Chemical compound C1=C(N2CCNCC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 VYYJRKSNFZQLMV-UHFFFAOYSA-N 0.000 claims description 3
- GBROYFRPPQZBSM-UHFFFAOYSA-N 4-tert-butyl-n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1=C(N2CCN(C)CC2)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GBROYFRPPQZBSM-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
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- 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 description 1
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- 101100325861 Arabidopsis thaliana BEE1 gene Proteins 0.000 description 1
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- RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 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
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- VCOJPHPOVDIRJK-LURJTMIESA-N [(2s)-1-methylpyrrolidin-2-yl]methanol Chemical compound CN1CCC[C@H]1CO VCOJPHPOVDIRJK-LURJTMIESA-N 0.000 description 1
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YNLFEVAOQLXINF-UHFFFAOYSA-N methylsulfanylmethane;tribromoborane Chemical compound CSC.BrB(Br)Br YNLFEVAOQLXINF-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FGBDZGNJGHTZCH-UHFFFAOYSA-N n-[3-(4-benzylpiperazin-1-yl)-4-methoxyphenyl]-5-chloro-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound COC1=CC=C(NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)C=C1N(CC1)CCN1CC1=CC=CC=C1 FGBDZGNJGHTZCH-UHFFFAOYSA-N 0.000 description 1
- FTXRUQGGZYFPBQ-UHFFFAOYSA-N n-[7-(4-methylpiperazin-1-yl)-2,3-dihydro-1-benzofuran-5-yl]naphthalene-2-sulfonamide Chemical compound C1CN(C)CCN1C1=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=CC2=C1OCC2 FTXRUQGGZYFPBQ-UHFFFAOYSA-N 0.000 description 1
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- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019237 ponceau SX Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 235000019234 riboflavin-5-sodium phosphate Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical class Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004173 sunset yellow FCF Substances 0.000 description 1
- 235000012751 sunset yellow FCF Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
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- 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
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9626377.7A GB9626377D0 (en) | 1996-12-19 | 1996-12-19 | Novel compounds |
| GBGB9700901.3A GB9700901D0 (en) | 1997-01-17 | 1997-01-17 | Novel compounds |
| GBGB9722757.3A GB9722757D0 (en) | 1997-10-27 | 1997-10-27 | Novel compounds |
| PCT/EP1997/007159 WO1998027081A1 (en) | 1996-12-19 | 1997-12-15 | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK80899A3 true SK80899A3 (en) | 2000-02-14 |
Family
ID=27268644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK808-99A SK80899A3 (en) | 1996-12-19 | 1997-12-15 | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
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