RU98113147A - USE OF TRICYCLIC DERIVATIVES OF 1,4-DIHYDRO-1,4-DIOXO-1H-NAPHTHALINE, NEW COMPOUNDS AND THEIR APPLICATION IN THERAPY. - Google Patents
USE OF TRICYCLIC DERIVATIVES OF 1,4-DIHYDRO-1,4-DIOXO-1H-NAPHTHALINE, NEW COMPOUNDS AND THEIR APPLICATION IN THERAPY.Info
- Publication number
- RU98113147A RU98113147A RU98113147/04A RU98113147A RU98113147A RU 98113147 A RU98113147 A RU 98113147A RU 98113147/04 A RU98113147/04 A RU 98113147/04A RU 98113147 A RU98113147 A RU 98113147A RU 98113147 A RU98113147 A RU 98113147A
- Authority
- RU
- Russia
- Prior art keywords
- dihydro
- dioxo
- thiazole
- naphtho
- furyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 9
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 239000000370 acceptor Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000001771 impaired Effects 0.000 claims 2
- 230000002757 inflammatory Effects 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- ZCAPVKVQKGVVEP-UHFFFAOYSA-N 2,3-dibromo-5-fluoronaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(Br)C(=O)C2=C1C=CC=C2F ZCAPVKVQKGVVEP-UHFFFAOYSA-N 0.000 claims 1
- PYQLLNKOBQDNOD-UHFFFAOYSA-N 2,3-dibromo-5-methoxynaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(Br)C(=O)C2=C1C=CC=C2OC PYQLLNKOBQDNOD-UHFFFAOYSA-N 0.000 claims 1
- TZJASHIDYNOMFL-UHFFFAOYSA-N 2,3-dibromo-5-methylnaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(Br)C(=O)C2=C1C=CC=C2C TZJASHIDYNOMFL-UHFFFAOYSA-N 0.000 claims 1
- WCNZRLIEPPOFCH-UHFFFAOYSA-N 2,3-dibromo-6-fluoronaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(Br)C(=O)C2=CC(F)=CC=C21 WCNZRLIEPPOFCH-UHFFFAOYSA-N 0.000 claims 1
- WODGMQAJBGQELR-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C1=NC=CS1 WODGMQAJBGQELR-UHFFFAOYSA-N 0.000 claims 1
- WBYCJQNVYQHORN-UHFFFAOYSA-N 2-(2,4-difluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound FC1=CC(F)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 WBYCJQNVYQHORN-UHFFFAOYSA-N 0.000 claims 1
- HWTVJTHJMSXSOF-UHFFFAOYSA-N 2-(2-chlorophenyl)benzo[f][1,3]benzoxazole-4,9-dione Chemical compound ClC1=CC=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2O1 HWTVJTHJMSXSOF-UHFFFAOYSA-N 0.000 claims 1
- BWXOYLNSHSYDNQ-UHFFFAOYSA-N 2-(2-fluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound FC1=CC=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 BWXOYLNSHSYDNQ-UHFFFAOYSA-N 0.000 claims 1
- UJVALBUTSNZOBZ-UHFFFAOYSA-N 2-(3-bromofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=COC(C=2SC3=C(C(C4=CC=CC=C4C3=O)=O)N=2)=C1Br UJVALBUTSNZOBZ-UHFFFAOYSA-N 0.000 claims 1
- KAWYXBAJUAUINZ-UHFFFAOYSA-N 2-(3-fluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound FC1=CC=CC(C=2SC3=C(C(C4=CC=CC=C4C3=O)=O)N=2)=C1 KAWYXBAJUAUINZ-UHFFFAOYSA-N 0.000 claims 1
- YQJQMUCPWRWSLJ-UHFFFAOYSA-N 2-(4,5-dibromofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(Br)=C(Br)C=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 YQJQMUCPWRWSLJ-UHFFFAOYSA-N 0.000 claims 1
- VYIHPRSTNSUTDF-UHFFFAOYSA-N 2-(4,5-dimethylfuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(C)=C(C)C=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 VYIHPRSTNSUTDF-UHFFFAOYSA-N 0.000 claims 1
- QACAEHLFWZCANV-UHFFFAOYSA-N 2-(4-bromofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound BrC1=COC(C=2SC3=C(C(C4=CC=CC=C4C3=O)=O)N=2)=C1 QACAEHLFWZCANV-UHFFFAOYSA-N 0.000 claims 1
- WSIVCDGLAAOUAM-UHFFFAOYSA-N 2-(4-chlorophenyl)benzo[f][1,3]benzoxazole-4,9-dione Chemical compound C1=CC(Cl)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2O1 WSIVCDGLAAOUAM-UHFFFAOYSA-N 0.000 claims 1
- ZZXJDJRHXRPFCR-UHFFFAOYSA-N 2-(4-fluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=CC(F)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 ZZXJDJRHXRPFCR-UHFFFAOYSA-N 0.000 claims 1
- WEUDJJQFPFEFPO-UHFFFAOYSA-N 2-(4-methoxyphenyl)benzo[f][1,3]benzoxazole-4,9-dione Chemical compound C1=CC(OC)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2O1 WEUDJJQFPFEFPO-UHFFFAOYSA-N 0.000 claims 1
- UOHJTGWIWLKOFH-UHFFFAOYSA-N 2-(5-aminofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(N)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 UOHJTGWIWLKOFH-UHFFFAOYSA-N 0.000 claims 1
- SIMPADCLDHQYQI-UHFFFAOYSA-N 2-(5-bromofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(Br)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 SIMPADCLDHQYQI-UHFFFAOYSA-N 0.000 claims 1
- DIRFZICDHCBSNE-UHFFFAOYSA-N 2-(5-chlorofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(Cl)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 DIRFZICDHCBSNE-UHFFFAOYSA-N 0.000 claims 1
- NHAYOCHSPVTTII-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(C)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 NHAYOCHSPVTTII-UHFFFAOYSA-N 0.000 claims 1
- AWQDKXZMIPOUHG-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 AWQDKXZMIPOUHG-UHFFFAOYSA-N 0.000 claims 1
- PQKOTJDKHSLTLO-UHFFFAOYSA-N 2-(5-phenyl-1,3-oxazol-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C(O1)=NC=C1C1=CC=CC=C1 PQKOTJDKHSLTLO-UHFFFAOYSA-N 0.000 claims 1
- XTTVXBZQXSTPSO-UHFFFAOYSA-N 2-(furan-2-yl)-5-hydroxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C=3C(O)=CC=CC=3C(=O)C=2SC=1C1=CC=CO1 XTTVXBZQXSTPSO-UHFFFAOYSA-N 0.000 claims 1
- QMVLNNDZQQMMHT-UHFFFAOYSA-N 2-(furan-2-yl)-5-methoxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C=3C(OC)=CC=CC=3C(=O)C=2SC=1C1=CC=CO1 QMVLNNDZQQMMHT-UHFFFAOYSA-N 0.000 claims 1
- NJPRVJMBTWGYAB-UHFFFAOYSA-N 2-(furan-2-yl)-6-methoxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(OC)=CC=C3C(=O)C=2SC=1C1=CC=CO1 NJPRVJMBTWGYAB-UHFFFAOYSA-N 0.000 claims 1
- JTZQOZNCHKHLLN-UHFFFAOYSA-N 2-(furan-2-yl)-7-methoxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(OC)=CC=C3C(=O)C=2N=C1C1=CC=CO1 JTZQOZNCHKHLLN-UHFFFAOYSA-N 0.000 claims 1
- WAGSLSVGWQJTKQ-UHFFFAOYSA-N 2-(furan-2-yl)-8-hydroxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(O)=CC=CC=3C(=O)C=2N=C1C1=CC=CO1 WAGSLSVGWQJTKQ-UHFFFAOYSA-N 0.000 claims 1
- UQKJPDYJFTVJOA-UHFFFAOYSA-N 2-(furan-2-yl)-8-methoxybenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(OC)=CC=CC=3C(=O)C=2N=C1C1=CC=CO1 UQKJPDYJFTVJOA-UHFFFAOYSA-N 0.000 claims 1
- HCJYSVXDXDYSED-UHFFFAOYSA-N 2-(furan-3-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C=1C=COC=1 HCJYSVXDXDYSED-UHFFFAOYSA-N 0.000 claims 1
- UHVIJLZSYHZCRS-UHFFFAOYSA-N 2-[5-(hydroxymethyl)furan-2-yl]benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(CO)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 UHVIJLZSYHZCRS-UHFFFAOYSA-N 0.000 claims 1
- CTCDJSQYICTGPT-UHFFFAOYSA-N 2-amino-3-bromo-5-fluoronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(N)=C(Br)C(=O)C2=C1F CTCDJSQYICTGPT-UHFFFAOYSA-N 0.000 claims 1
- LYVAXRGHTGGEBJ-UHFFFAOYSA-N 2-amino-3-bromo-5-methoxynaphthalene-1,4-dione Chemical compound O=C1C(N)=C(Br)C(=O)C2=C1C=CC=C2OC LYVAXRGHTGGEBJ-UHFFFAOYSA-N 0.000 claims 1
- DEIOLVIXEQNANK-UHFFFAOYSA-N 2-amino-3-bromo-5-methylnaphthalene-1,4-dione Chemical compound O=C1C(N)=C(Br)C(=O)C2=C1C=CC=C2C DEIOLVIXEQNANK-UHFFFAOYSA-N 0.000 claims 1
- RIGRHQRUQGLHKC-UHFFFAOYSA-N 2-amino-3-bromo-6-fluoronaphthalene-1,4-dione Chemical compound FC1=CC=C2C(=O)C(N)=C(Br)C(=O)C2=C1 RIGRHQRUQGLHKC-UHFFFAOYSA-N 0.000 claims 1
- BQHURORABWQSBR-UHFFFAOYSA-N 2-amino-3-chloro-6-methylnaphthalene-1,4-dione Chemical compound O=C1C(N)=C(Cl)C(=O)C2=CC(C)=CC=C21 BQHURORABWQSBR-UHFFFAOYSA-N 0.000 claims 1
- WEOBMYUTPYXMRM-UHFFFAOYSA-N 2-pyridin-3-ylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C1=CC=CN=C1 WEOBMYUTPYXMRM-UHFFFAOYSA-N 0.000 claims 1
- PPWXETUTFRZGNR-UHFFFAOYSA-N 2-pyridin-4-ylbenzo[f][1,3]benzothiazole-4,9-dione;sulfuric acid Chemical compound OS(O)(=O)=O.S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C1=CC=NC=C1 PPWXETUTFRZGNR-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZGHCUFXULYADMS-UHFFFAOYSA-N 2-thiophen-2-ylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C1=CC=CS1 ZGHCUFXULYADMS-UHFFFAOYSA-N 0.000 claims 1
- FTDCOVZWOANATD-UHFFFAOYSA-N 2-thiophen-3-ylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC=CC=C3C(=O)C=2N=C1C=1C=CSC=1 FTDCOVZWOANATD-UHFFFAOYSA-N 0.000 claims 1
- FMYCGBHYGJLPJE-UHFFFAOYSA-N 3-amino-2-bromo-5-fluoronaphthalene-1,4-dione Chemical compound C1=CC(F)=C2C(=O)C(N)=C(Br)C(=O)C2=C1 FMYCGBHYGJLPJE-UHFFFAOYSA-N 0.000 claims 1
- CKMGFAPTTIUTOR-UHFFFAOYSA-N 3-amino-2-bromo-5-methoxynaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(N)C(=O)C2=C1C=CC=C2OC CKMGFAPTTIUTOR-UHFFFAOYSA-N 0.000 claims 1
- GAJHIHMKTAOXSX-UHFFFAOYSA-N 3-amino-2-bromo-5-methylnaphthalene-1,4-dione Chemical compound O=C1C(Br)=C(N)C(=O)C2=C1C=CC=C2C GAJHIHMKTAOXSX-UHFFFAOYSA-N 0.000 claims 1
- OLRLFLYEECOSIQ-UHFFFAOYSA-N 3-amino-2-bromo-6-fluoronaphthalene-1,4-dione Chemical compound C1=C(F)C=C2C(=O)C(N)=C(Br)C(=O)C2=C1 OLRLFLYEECOSIQ-UHFFFAOYSA-N 0.000 claims 1
- PTBHGQZZVAILEN-UHFFFAOYSA-N 3-amino-2-chloro-6-methylnaphthalene-1,4-dione Chemical compound O=C1C(Cl)=C(N)C(=O)C2=CC(C)=CC=C21 PTBHGQZZVAILEN-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- XDFMBCOYRSZPPK-UHFFFAOYSA-N 5-fluoro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C=3C(F)=CC=CC=3C(=O)C=2SC=1C1=CC=CO1 XDFMBCOYRSZPPK-UHFFFAOYSA-N 0.000 claims 1
- JUOYZQOSMGRKEA-UHFFFAOYSA-N 5-methoxy-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C=3C(OC)=CC=CC=3C(=O)C=2SC=1C1=CC=CC=C1 JUOYZQOSMGRKEA-UHFFFAOYSA-N 0.000 claims 1
- DBDLTJRCKGCKSK-UHFFFAOYSA-N 5-methoxynaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2OC DBDLTJRCKGCKSK-UHFFFAOYSA-N 0.000 claims 1
- QWNVAIGNJXBNLZ-UHFFFAOYSA-N 5-methyl-2-(4-oxofuran-2-yl)-4H-benzo[f][1,3]benzothiazol-9-one Chemical compound N=1C=2CC=3C(C)=CC=CC=3C(=O)C=2SC=1C1=CC(=O)CO1 QWNVAIGNJXBNLZ-UHFFFAOYSA-N 0.000 claims 1
- ZLDIIMNECGPNHE-UHFFFAOYSA-N 5-methyl-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C=3C(C)=CC=CC=3C(=O)C=2SC=1C1=CC=CC=C1 ZLDIIMNECGPNHE-UHFFFAOYSA-N 0.000 claims 1
- FRGLVKLVMQFUBQ-UHFFFAOYSA-N 6-chloro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(Cl)=CC=C3C(=O)C=2SC=1C1=CC=CO1 FRGLVKLVMQFUBQ-UHFFFAOYSA-N 0.000 claims 1
- SAKVALIVNPPJEB-UHFFFAOYSA-N 6-fluoro-2-(4-fluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=CC(F)=CC=C1C1=NC(C(C2=CC(F)=CC=C2C2=O)=O)=C2S1 SAKVALIVNPPJEB-UHFFFAOYSA-N 0.000 claims 1
- RDCXUSTWGGGHPO-UHFFFAOYSA-N 6-fluoro-2-(4-methylphenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=CC(C)=CC=C1C1=NC(C(C2=CC(F)=CC=C2C2=O)=O)=C2S1 RDCXUSTWGGGHPO-UHFFFAOYSA-N 0.000 claims 1
- GMGCRPBPCLMUIC-UHFFFAOYSA-N 6-fluoro-2-(5-methylfuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(C)=CC=C1C1=NC(C(C2=CC(F)=CC=C2C2=O)=O)=C2S1 GMGCRPBPCLMUIC-UHFFFAOYSA-N 0.000 claims 1
- UTTAXUHMYINTMX-UHFFFAOYSA-N 6-fluoro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(F)=CC=C3C(=O)C=2SC=1C1=CC=CO1 UTTAXUHMYINTMX-UHFFFAOYSA-N 0.000 claims 1
- LSGOCDXRYJHIEQ-UHFFFAOYSA-N 6-fluoro-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(F)=CC=C3C(=O)C=2SC=1C1=CC=CC=C1 LSGOCDXRYJHIEQ-UHFFFAOYSA-N 0.000 claims 1
- ZDLKOTRSOCOFCP-UHFFFAOYSA-N 6-methoxy-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(OC)=CC=C3C(=O)C=2SC=1C1=CC=CC=C1 ZDLKOTRSOCOFCP-UHFFFAOYSA-N 0.000 claims 1
- CRWQOXNARPFUOY-UHFFFAOYSA-N 6-methyl-2-(4-oxofuran-2-yl)-4H-benzo[f][1,3]benzothiazol-9-one Chemical compound N=1C=2CC3=CC(C)=CC=C3C(=O)C=2SC=1C1=CC(=O)CO1 CRWQOXNARPFUOY-UHFFFAOYSA-N 0.000 claims 1
- NQZZQASWBVPEFO-UHFFFAOYSA-N 6-methyl-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound N=1C=2C(=O)C3=CC(C)=CC=C3C(=O)C=2SC=1C1=CC=CC=C1 NQZZQASWBVPEFO-UHFFFAOYSA-N 0.000 claims 1
- OEURFZARVCAAPN-UHFFFAOYSA-N 7-chloro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(Cl)=CC=C3C(=O)C=2N=C1C1=CC=CO1 OEURFZARVCAAPN-UHFFFAOYSA-N 0.000 claims 1
- DSGKYGXTHXHGOP-UHFFFAOYSA-N 7-fluoro-2-(4-fluorophenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=CC(F)=CC=C1C1=NC(C(C2=CC=C(F)C=C2C2=O)=O)=C2S1 DSGKYGXTHXHGOP-UHFFFAOYSA-N 0.000 claims 1
- HNZBUGJHGYBFOS-UHFFFAOYSA-N 7-fluoro-2-(4-methylphenyl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound C1=CC(C)=CC=C1C1=NC(C(C2=CC=C(F)C=C2C2=O)=O)=C2S1 HNZBUGJHGYBFOS-UHFFFAOYSA-N 0.000 claims 1
- YYWKHRFJVRDNCF-UHFFFAOYSA-N 7-fluoro-2-(5-methylfuran-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound O1C(C)=CC=C1C1=NC(C(C2=CC=C(F)C=C2C2=O)=O)=C2S1 YYWKHRFJVRDNCF-UHFFFAOYSA-N 0.000 claims 1
- RICGFIYGULTJDH-UHFFFAOYSA-N 7-fluoro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(F)=CC=C3C(=O)C=2N=C1C1=CC=CO1 RICGFIYGULTJDH-UHFFFAOYSA-N 0.000 claims 1
- IEDQSQUWNPZGKG-UHFFFAOYSA-N 7-fluoro-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(F)=CC=C3C(=O)C=2N=C1C1=CC=CC=C1 IEDQSQUWNPZGKG-UHFFFAOYSA-N 0.000 claims 1
- QAEKLBWGHLEVTE-UHFFFAOYSA-N 7-methoxy-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(OC)=CC=C3C(=O)C=2N=C1C1=CC=CC=C1 QAEKLBWGHLEVTE-UHFFFAOYSA-N 0.000 claims 1
- VBGCFJTVRSMYFJ-UHFFFAOYSA-N 7-methyl-2-(4-oxofuran-2-yl)-4H-benzo[f][1,3]benzothiazol-9-one Chemical compound S1C=2C(=O)C3=CC(C)=CC=C3CC=2N=C1C1=CC(=O)CO1 VBGCFJTVRSMYFJ-UHFFFAOYSA-N 0.000 claims 1
- QLPMNLPHWFASFB-UHFFFAOYSA-N 7-methyl-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C3=CC(C)=CC=C3C(=O)C=2N=C1C1=CC=CC=C1 QLPMNLPHWFASFB-UHFFFAOYSA-N 0.000 claims 1
- MBSQDZBRDUZPEL-UHFFFAOYSA-N 8-fluoro-2-(furan-2-yl)benzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(F)=CC=CC=3C(=O)C=2N=C1C1=CC=CO1 MBSQDZBRDUZPEL-UHFFFAOYSA-N 0.000 claims 1
- UFQQAIJDUDGRKQ-UHFFFAOYSA-N 8-hydroxy-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(O)=CC=CC=3C(=O)C=2N=C1C1=CC=CC=C1 UFQQAIJDUDGRKQ-UHFFFAOYSA-N 0.000 claims 1
- VTVVATVHWHSKRM-UHFFFAOYSA-N 8-methoxy-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(OC)=CC=CC=3C(=O)C=2N=C1C1=CC=CC=C1 VTVVATVHWHSKRM-UHFFFAOYSA-N 0.000 claims 1
- MODVUQQUKVJFTA-UHFFFAOYSA-N 8-methyl-2-(4-oxofuran-2-yl)-4H-benzo[f][1,3]benzothiazol-9-one Chemical compound S1C=2C(=O)C=3C(C)=CC=CC=3CC=2N=C1C1=CC(=O)CO1 MODVUQQUKVJFTA-UHFFFAOYSA-N 0.000 claims 1
- GZMWIVFESHCPOY-UHFFFAOYSA-N 8-methyl-2-phenylbenzo[f][1,3]benzothiazole-4,9-dione Chemical compound S1C=2C(=O)C=3C(C)=CC=CC=3C(=O)C=2N=C1C1=CC=CC=C1 GZMWIVFESHCPOY-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010027599 Migraine Diseases 0.000 claims 1
- 208000008085 Migraine Disorders Diseases 0.000 claims 1
- NUOZWAFGWDBXKM-UHFFFAOYSA-N N-[5-(4,9-dioxobenzo[f][1,3]benzothiazol-2-yl)furan-2-yl]acetamide Chemical compound O1C(NC(=O)C)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 NUOZWAFGWDBXKM-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 206010040070 Septic shock Diseases 0.000 claims 1
- KCRIFPXXOFXKSR-UHFFFAOYSA-N [5-(4,9-dioxobenzo[f][1,3]benzothiazol-2-yl)furan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2S1 KCRIFPXXOFXKSR-UHFFFAOYSA-N 0.000 claims 1
- HJLDPBXWNCCXGM-UHFFFAOYSA-N benzo[f][1,3]benzothiazole Chemical compound C1=CC=C2C=C(SC=N3)C3=CC2=C1 HJLDPBXWNCCXGM-UHFFFAOYSA-N 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 230000000271 cardiovascular Effects 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 201000002282 venous insufficiency Diseases 0.000 claims 1
Claims (9)
где A является либо атомом серы, кислорода, либо радикалом R3N, где R3 является атомом водорода, C1-C5-алкилом, или замещенным или незамещенным ароматическим циклом, или замещенным или незамещенным гетероароматическим циклом, R1 является либо C1-C5-алкилом; либо радикалом R4NH, где R4 является атомом водорода, C1-С5-алкилом, или замещенным или незамещенным ароматическим циклом, или замещенным или незамещенным гетероароматическим циклом, либо ароматическим циклом, замещенным или незамещенным одной или несколькими группами акцепторов или доноров, или гетероароматическим циклом, имеющим один или несколько гетероатомов и замещенным или незамещенным группами акцепторов или доноров; R2 является атомом водорода, галогена, C1-C5-алкилом, атомом кислорода, замещенным или незамещенным C1-C5-алкилом, или радикалом NR5R5', где R5 и R5' являются, независимо друг от друга, атомом водорода, кислорода или одновалентными органическими радикалами C1-C5, для получения лекарственного средства, предназначенного для лечения болезней, связанных с нарушением венозной функции и/или воспалительными отеками.1. The use of tricyclic derivatives and their pharmaceutically acceptable salts, corresponding to the General formula
where A is either a sulfur atom, an oxygen atom, or an R 3 N radical, where R 3 is a hydrogen atom, a C 1 -C 5 alkyl, or a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R 1 is either C 1 -C 5 alkyl; or an R 4 NH radical, where R 4 is a hydrogen atom, a C 1 -C 5 alkyl, or a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, or an aromatic cycle substituted or unsubstituted by one or more groups of acceptors or donors, or a heteroaromatic ring having one or more heteroatoms and substituted or unsubstituted groups of acceptors or donors; R 2 is hydrogen, halogen, C 1 -C 5 -alkyl, oxygen atom, substituted or unsubstituted C 1 -C 5 -alkyl, or a radical NR 5 R 5 'where R 5 and R 5' are, independently of each friend, a hydrogen atom, oxygen or monovalent organic radicals C 1 -C 5 to obtain a medicinal product intended for the treatment of diseases associated with impaired venous function and / or inflammatory edema.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9514683 | 1995-12-12 | ||
FR9514683A FR2742153B1 (en) | 1995-12-12 | 1995-12-12 | USE OF TRICYCLIC DERIVATIVES OF 1,4-DIHYDRO-1,4-DIOXO-1H-NAPHTALENE, NEW COMPOUNDS OBTAINED AND THEIR THERAPEUTIC APPLICATION |
Publications (2)
Publication Number | Publication Date |
---|---|
RU98113147A true RU98113147A (en) | 2000-06-20 |
RU2178791C2 RU2178791C2 (en) | 2002-01-27 |
Family
ID=9485393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU98113147/04A RU2178791C2 (en) | 1995-12-12 | 1996-12-10 | Use of tricyclic derivatives of 1,4-dihydro-1,4-dioxo-1h-naphthalene and its novel compounds, pharmaceutical composition based on thereof and derivatives of substituted naphthalenes as intermediate compounds |
Country Status (26)
Country | Link |
---|---|
US (1) | US6262095B1 (en) |
EP (1) | EP0876356B1 (en) |
JP (1) | JP2000501724A (en) |
KR (1) | KR19990072080A (en) |
AP (1) | AP889A (en) |
AR (1) | AR005054A1 (en) |
AT (1) | ATE207907T1 (en) |
AU (1) | AU716199B2 (en) |
BR (1) | BR9611935A (en) |
CA (1) | CA2240279A1 (en) |
CZ (1) | CZ181198A3 (en) |
DE (1) | DE69616598D1 (en) |
EE (1) | EE9800174A (en) |
FR (1) | FR2742153B1 (en) |
HU (1) | HUP9901247A3 (en) |
ID (1) | ID16081A (en) |
IL (1) | IL124558A0 (en) |
LT (1) | LT4491B (en) |
LV (1) | LV12188B (en) |
NO (1) | NO982696L (en) |
NZ (1) | NZ323967A (en) |
OA (1) | OA10696A (en) |
PL (1) | PL327168A1 (en) |
RU (1) | RU2178791C2 (en) |
TR (1) | TR199801069T2 (en) |
WO (1) | WO1997021684A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8030337B2 (en) | 2006-06-19 | 2011-10-04 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
Families Citing this family (8)
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AU2003999A (en) * | 1997-12-19 | 1999-07-12 | Advanced Research And Technology Institute, Inc. | Modulators of ryanodine receptors comprising 2-(aryl)-4,7-dioxobenzothiazoles and analogues thereof |
EP1347971B1 (en) * | 2000-12-21 | 2006-03-01 | Bristol-Myers Squibb Company | Thiazolyl inhibitors of tec family tyrosine kinases |
US7754463B2 (en) | 2006-06-20 | 2010-07-13 | Dana-Farber Cancer Institute | Inhibitors of USP1 Deubiquitinating Enzyme Complex |
WO2011137320A2 (en) | 2010-04-30 | 2011-11-03 | Dana-Farber Cancer Institute, Inc. | Small molecule inhibitors of usp1 deubiquitinating enzyme activity |
US9040713B2 (en) * | 2010-09-27 | 2015-05-26 | Emory University | Methods of managing blood sugar levels and compositions related thereto |
US9725425B1 (en) | 2014-02-25 | 2017-08-08 | Dana-Farber Cancer Institute, Inc. | Compounds and methods for treating cancer |
RU2545091C1 (en) * | 2014-03-18 | 2015-03-27 | Федеральное государственное бюджетное учреждение "Российский онкологический научный центр имени Н.Н. Блохина" Российской академии медицинских наук (ФГБУ "РОНЦ им. Н.Н. Блохина" РАМН) | 1-R-4,9-DIOXO-1H-NAPTHO[2,3-d][1,2,3]TRIAZOLE-4-OXIM-2-OXIDES AND THEIR DERIVATIVES POSSESSING CYTOTOXIC ACTIVITY |
WO2017106624A1 (en) | 2015-12-18 | 2017-06-22 | The Board Of Regents Of The University Of Texas System | Napthoquinones, pro-drugs, and methods of use thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US3039925A (en) | 1957-04-24 | 1962-06-19 | Bayer Ag | Compositions for the treatment of tuberculosis |
US4746676A (en) | 1984-09-12 | 1988-05-24 | Rorer Pharmaceutical Corporation | Carboxyalkyl dipeptide compounds |
JPH05112533A (en) * | 1991-05-08 | 1993-05-07 | Upjohn Co:The | Imidazobenzoquinoline and agent for preventing and treating hypertension and conjestive heart failure containing same as effective component |
-
1995
- 1995-12-12 FR FR9514683A patent/FR2742153B1/en not_active Expired - Fee Related
-
1996
- 1996-12-10 CZ CZ981811A patent/CZ181198A3/en unknown
- 1996-12-10 RU RU98113147/04A patent/RU2178791C2/en active
- 1996-12-10 NZ NZ323967A patent/NZ323967A/en unknown
- 1996-12-10 AP APAP/P/1998/001275A patent/AP889A/en active
- 1996-12-10 JP JP9521799A patent/JP2000501724A/en active Pending
- 1996-12-10 US US09/043,831 patent/US6262095B1/en not_active Expired - Fee Related
- 1996-12-10 TR TR1998/01069T patent/TR199801069T2/en unknown
- 1996-12-10 IL IL12455896A patent/IL124558A0/en unknown
- 1996-12-10 EE EE9800174A patent/EE9800174A/en unknown
- 1996-12-10 KR KR1019980704387A patent/KR19990072080A/en not_active Application Discontinuation
- 1996-12-10 BR BR9611935A patent/BR9611935A/en unknown
- 1996-12-10 CA CA002240279A patent/CA2240279A1/en not_active Abandoned
- 1996-12-10 AU AU11018/97A patent/AU716199B2/en not_active Ceased
- 1996-12-10 EP EP96941734A patent/EP0876356B1/en not_active Expired - Lifetime
- 1996-12-10 AT AT96941734T patent/ATE207907T1/en not_active IP Right Cessation
- 1996-12-10 PL PL96327168A patent/PL327168A1/en unknown
- 1996-12-10 HU HU9901247A patent/HUP9901247A3/en unknown
- 1996-12-10 WO PCT/FR1996/001973 patent/WO1997021684A1/en not_active Application Discontinuation
- 1996-12-10 DE DE69616598T patent/DE69616598D1/en not_active Expired - Lifetime
- 1996-12-12 ID IDP963710A patent/ID16081A/en unknown
- 1996-12-12 AR ARP960105648A patent/AR005054A1/en unknown
-
1998
- 1998-06-10 LT LT98-085A patent/LT4491B/en not_active IP Right Cessation
- 1998-06-11 NO NO982696A patent/NO982696L/en not_active Application Discontinuation
- 1998-06-12 OA OA9800080A patent/OA10696A/en unknown
- 1998-06-12 LV LVP-98-136A patent/LV12188B/en unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8030337B2 (en) | 2006-06-19 | 2011-10-04 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8236837B2 (en) | 2006-06-19 | 2012-08-07 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8349879B2 (en) | 2006-06-19 | 2013-01-08 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8552037B2 (en) | 2006-06-19 | 2013-10-08 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8895591B2 (en) | 2006-06-19 | 2014-11-25 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
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