LT4491B - 1,4-dihidro-1,4-diokso-1h-naftaleno triciklinių darinių panaudojimas, naujų junginių gavimas ir jų taikymas vaistų gamyboje - Google Patents
1,4-dihidro-1,4-diokso-1h-naftaleno triciklinių darinių panaudojimas, naujų junginių gavimas ir jų taikymas vaistų gamyboje Download PDFInfo
- Publication number
- LT4491B LT4491B LT98-085A LT98085A LT4491B LT 4491 B LT4491 B LT 4491B LT 98085 A LT98085 A LT 98085A LT 4491 B LT4491 B LT 4491B
- Authority
- LT
- Lithuania
- Prior art keywords
- dihydro
- dioxo
- thiazole
- naphtho
- novel compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 122
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 201000010099 disease Diseases 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 22
- -1 compound 4,9-dihydro-4,9-dioxo-2- (4-pyridyl) -naphtho [2,3-d] thiazole sulfate Chemical class 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 12
- 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 description 8
- 230000004872 arterial blood pressure Effects 0.000 claims description 8
- 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 description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 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 description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 201000002282 venous insufficiency Diseases 0.000 claims description 5
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- 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 description 4
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- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 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 description 3
- 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 description 3
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- 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 description 3
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- 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 description 3
- 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 description 3
- 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 description 3
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- 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 description 3
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- 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 description 3
- 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 description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 206010046996 Varicose vein Diseases 0.000 claims description 3
- 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 description 3
- 230000008859 change Effects 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 208000027185 varicose disease Diseases 0.000 claims description 3
- SPTHAPOLVDKHEU-UHFFFAOYSA-N 2,3-dimethylbenzo[f]benzimidazole-4,9-dione;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(=O)C(N=C(N3C)C)=C3C(=O)C2=C1 SPTHAPOLVDKHEU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- XUFYAZPAMNFIPW-UHFFFAOYSA-N 2-(2-fluorophenyl)-1h-benzo[f]benzimidazole-4,9-dione Chemical compound FC1=CC=CC=C1C1=NC(C(C2=CC=CC=C2C2=O)=O)=C2N1 XUFYAZPAMNFIPW-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
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- 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 description 2
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Classifications
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/30—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by two rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9514683A FR2742153B1 (fr) | 1995-12-12 | 1995-12-12 | Utilisation de derives tricycliques du 1,4-dihydro-1,4- dioxo-1h-naphtalene, nouveaux composes obtenus et leur application en therapeutique |
Publications (2)
Publication Number | Publication Date |
---|---|
LT98085A LT98085A (en) | 1998-11-25 |
LT4491B true LT4491B (lt) | 1999-04-26 |
Family
ID=9485393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LT98-085A LT4491B (lt) | 1995-12-12 | 1998-06-10 | 1,4-dihidro-1,4-diokso-1h-naftaleno triciklinių darinių panaudojimas, naujų junginių gavimas ir jų taikymas vaistų gamyboje |
Country Status (26)
Country | Link |
---|---|
US (1) | US6262095B1 (cs) |
EP (1) | EP0876356B1 (cs) |
JP (1) | JP2000501724A (cs) |
KR (1) | KR19990072080A (cs) |
AP (1) | AP889A (cs) |
AR (1) | AR005054A1 (cs) |
AT (1) | ATE207907T1 (cs) |
AU (1) | AU716199B2 (cs) |
BR (1) | BR9611935A (cs) |
CA (1) | CA2240279A1 (cs) |
CZ (1) | CZ181198A3 (cs) |
DE (1) | DE69616598D1 (cs) |
EE (1) | EE9800174A (cs) |
FR (1) | FR2742153B1 (cs) |
HU (1) | HUP9901247A3 (cs) |
ID (1) | ID16081A (cs) |
IL (1) | IL124558A0 (cs) |
LT (1) | LT4491B (cs) |
LV (1) | LV12188B (cs) |
NO (1) | NO982696L (cs) |
NZ (1) | NZ323967A (cs) |
OA (1) | OA10696A (cs) |
PL (1) | PL327168A1 (cs) |
RU (1) | RU2178791C2 (cs) |
TR (1) | TR199801069T2 (cs) |
WO (1) | WO1997021684A1 (cs) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
AU3113902A (en) * | 2000-12-21 | 2002-07-01 | Bristol Myers Squibb Co | Thiazolyl inhibitors of tec family tyrosine kinases |
AR061478A1 (es) | 2006-06-19 | 2008-08-27 | Takeda Pharmaceutical | Compuesto triciclico y composicion farmaceutica |
US7754463B2 (en) | 2006-06-20 | 2010-07-13 | Dana-Farber Cancer Institute | Inhibitors of USP1 Deubiquitinating Enzyme Complex |
US9518032B2 (en) | 2010-04-30 | 2016-12-13 | Dana-Farber Cancer Institute, Inc. | Small molecule inhibitors of USP1 deubiquitinating enzyme activity |
WO2012047628A2 (en) * | 2010-09-27 | 2012-04-12 | 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 (ru) * | 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-ДИОКСО-1H-НАФТО[2,3-d][1,2,3]ТРИАЗОЛ-4-ОКСИМ-2-ОКСИДЫ И ИХ ПРОИЗВОДНЫЕ, ОБЛАДАЮЩИЕ ЦИТОТОКСИЧЕСКОЙ АКТИВНОСТЬЮ |
US10829427B2 (en) | 2015-12-18 | 2020-11-10 | The Board Of Regents Of The University Of Texas System | Naphthoquinones, pro-drugs, and methods of use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3039925A (en) | 1957-04-24 | 1962-06-19 | Bayer Ag | Compositions for the treatment of tuberculosis |
JPS61251657A (ja) | 1984-09-12 | 1986-11-08 | ユ−エスヴイ− フア−マシユ−テイカル コ−ポレ−シヨン | 抗高血圧性誘導体類 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05112533A (ja) * | 1991-05-08 | 1993-05-07 | Upjohn Co:The | イミダゾベンゾキノン類およびこれを有効成分とする高血圧・鬱血性心不全の予防・治療剤 |
WO1994003439A1 (en) * | 1992-07-29 | 1994-02-17 | Agouron Pharmaceuticals, Inc. | Antiproliferative tricyclic compounds |
-
1995
- 1995-12-12 FR FR9514683A patent/FR2742153B1/fr not_active Expired - Fee Related
-
1996
- 1996-12-10 EE EE9800174A patent/EE9800174A/xx unknown
- 1996-12-10 IL IL12455896A patent/IL124558A0/xx unknown
- 1996-12-10 DE DE69616598T patent/DE69616598D1/de not_active Expired - Lifetime
- 1996-12-10 JP JP9521799A patent/JP2000501724A/ja active Pending
- 1996-12-10 WO PCT/FR1996/001973 patent/WO1997021684A1/fr not_active Application Discontinuation
- 1996-12-10 TR TR1998/01069T patent/TR199801069T2/xx unknown
- 1996-12-10 US US09/043,831 patent/US6262095B1/en not_active Expired - Fee Related
- 1996-12-10 CZ CZ981811A patent/CZ181198A3/cs unknown
- 1996-12-10 KR KR1019980704387A patent/KR19990072080A/ko not_active Ceased
- 1996-12-10 PL PL96327168A patent/PL327168A1/xx unknown
- 1996-12-10 HU HU9901247A patent/HUP9901247A3/hu unknown
- 1996-12-10 EP EP96941734A patent/EP0876356B1/fr not_active Expired - Lifetime
- 1996-12-10 NZ NZ323967A patent/NZ323967A/en unknown
- 1996-12-10 RU RU98113147/04A patent/RU2178791C2/ru active
- 1996-12-10 AP APAP/P/1998/001275A patent/AP889A/en active
- 1996-12-10 CA CA002240279A patent/CA2240279A1/fr not_active Abandoned
- 1996-12-10 AU AU11018/97A patent/AU716199B2/en not_active Ceased
- 1996-12-10 AT AT96941734T patent/ATE207907T1/de not_active IP Right Cessation
- 1996-12-10 BR BR9611935A patent/BR9611935A/pt unknown
- 1996-12-12 AR ARP960105648A patent/AR005054A1/es unknown
- 1996-12-12 ID IDP963710A patent/ID16081A/id unknown
-
1998
- 1998-06-10 LT LT98-085A patent/LT4491B/lt not_active IP Right Cessation
- 1998-06-11 NO NO982696A patent/NO982696L/no not_active Application Discontinuation
- 1998-06-12 LV LVP-98-136A patent/LV12188B/en unknown
- 1998-06-12 OA OA9800080A patent/OA10696A/fr unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3039925A (en) | 1957-04-24 | 1962-06-19 | Bayer Ag | Compositions for the treatment of tuberculosis |
JPS61251657A (ja) | 1984-09-12 | 1986-11-08 | ユ−エスヴイ− フア−マシユ−テイカル コ−ポレ−シヨン | 抗高血圧性誘導体類 |
Non-Patent Citations (2)
Title |
---|
F. I. CARROLL ANDJ. T. BLACKWELL: "Synthesis of 1H-naphth[2,3-d]imidazole-4,9-diones by acid catalyzed cyclization of 2-Acylamino-3-amino-1,4-naphthoquinone", JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, pages 909 - 916 |
JOHN R. E. HOOVER, ALLAN R. DAY: "Preparation of Some Imidazole Derivatives of 1,4-Naphthoquinone", J. AM. CHEM. SOC., 1954, pages 4148 - 4152, XP002030731, DOI: doi:10.1021/ja01645a028 |
Also Published As
Publication number | Publication date |
---|---|
EE9800174A (et) | 1998-12-15 |
FR2742153A1 (fr) | 1997-06-13 |
TR199801069T2 (xx) | 1998-08-21 |
KR19990072080A (ko) | 1999-09-27 |
EP0876356B1 (fr) | 2001-10-31 |
ATE207907T1 (de) | 2001-11-15 |
HUP9901247A2 (hu) | 1999-08-30 |
OA10696A (fr) | 2002-11-26 |
BR9611935A (pt) | 1999-05-18 |
CA2240279A1 (fr) | 1997-06-19 |
RU2178791C2 (ru) | 2002-01-27 |
LV12188B (en) | 1999-07-20 |
AU1101897A (en) | 1997-07-03 |
NO982696D0 (no) | 1998-06-11 |
IL124558A0 (en) | 1998-12-06 |
AP889A (en) | 2000-11-17 |
EP0876356A1 (fr) | 1998-11-11 |
FR2742153B1 (fr) | 1998-02-13 |
LV12188A (lv) | 1998-12-20 |
JP2000501724A (ja) | 2000-02-15 |
AU716199B2 (en) | 2000-02-24 |
AR005054A1 (es) | 1999-04-07 |
DE69616598D1 (de) | 2001-12-06 |
US6262095B1 (en) | 2001-07-17 |
NO982696L (no) | 1998-08-11 |
WO1997021684A1 (fr) | 1997-06-19 |
PL327168A1 (en) | 1998-11-23 |
NZ323967A (en) | 2000-06-23 |
LT98085A (en) | 1998-11-25 |
HUP9901247A3 (en) | 2000-08-28 |
AP9801275A0 (en) | 1998-06-30 |
ID16081A (id) | 1997-09-04 |
CZ181198A3 (cs) | 1998-09-16 |
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