KR920006336A - 1,3-벤족사진 유도체, 그의 제조방법 및 용도 - Google Patents
1,3-벤족사진 유도체, 그의 제조방법 및 용도 Download PDFInfo
- Publication number
- KR920006336A KR920006336A KR1019910016710A KR910016710A KR920006336A KR 920006336 A KR920006336 A KR 920006336A KR 1019910016710 A KR1019910016710 A KR 1019910016710A KR 910016710 A KR910016710 A KR 910016710A KR 920006336 A KR920006336 A KR 920006336A
- Authority
- KR
- South Korea
- Prior art keywords
- oxide
- dimethyl
- cyano
- optionally substituted
- benzoxazine
- Prior art date
Links
- CGACGSHTSCXSSO-UHFFFAOYSA-N 2h-1,3-benzoxazine Chemical class C1=CC=C2C=NCOC2=C1 CGACGSHTSCXSSO-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- -1 Thiocarbonyloxy group Chemical group 0.000 claims 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 5
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- USSAGPZNNSQHCL-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine-6-carbonitrile Chemical compound N=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] USSAGPZNNSQHCL-UHFFFAOYSA-N 0.000 claims 2
- MSBJDOSDIOINPQ-UHFFFAOYSA-N 6-bromo-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] MSBJDOSDIOINPQ-UHFFFAOYSA-N 0.000 claims 2
- SINHQCMLPQYEPE-UHFFFAOYSA-N 6-bromo-7-fluoro-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC(F)=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] SINHQCMLPQYEPE-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 241001024304 Mino Species 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000006356 alkylene carbonyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims 1
- VOWNTLZDZPKBHZ-UHFFFAOYSA-N 1-[2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazin-6-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2OC(C)(C)N=C1C1=CC=CC=[N+]1[O-] VOWNTLZDZPKBHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims 1
- INWVUPXSQPKTAC-UHFFFAOYSA-N 2,2,7-trimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine-6-carbonitrile Chemical compound C1=2C=C(C#N)C(C)=CC=2OC(C)(C)N=C1C1=CC=CC=[N+]1[O-] INWVUPXSQPKTAC-UHFFFAOYSA-N 0.000 claims 1
- VJMRDBBMYSAICY-UHFFFAOYSA-N 2,2,7-trimethyl-6-nitro-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound C1=2C=C([N+]([O-])=O)C(C)=CC=2OC(C)(C)N=C1C1=CC=CC=[N+]1[O-] VJMRDBBMYSAICY-UHFFFAOYSA-N 0.000 claims 1
- PUCWZWGTIREMBA-UHFFFAOYSA-N 2,2-dimethyl-4-(1-methyl-2-oxopyrrolidin-3-yl)-1,3-benzoxazine-6-carbonitrile Chemical compound O=C1N(C)CCC1C1=NC(C)(C)OC2=CC=C(C#N)C=C12 PUCWZWGTIREMBA-UHFFFAOYSA-N 0.000 claims 1
- FRYSBHGYKHZCAE-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-6-(1,1,2,2,2-pentafluoroethyl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(C(F)(F)C(F)(F)F)C=C2C=1C1=CC=CC=[N+]1[O-] FRYSBHGYKHZCAE-UHFFFAOYSA-N 0.000 claims 1
- BLUGMTNEBJBUBY-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-6-(1,2,2-trifluoroethenyl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(C(F)=C(F)F)C=C2C=1C1=CC=CC=[N+]1[O-] BLUGMTNEBJBUBY-UHFFFAOYSA-N 0.000 claims 1
- JVABRYMGSQEGCI-UHFFFAOYSA-N 2,2-dimethyl-4-pyridin-2-yl-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=CC=C2C=1C1=CC=CC=N1 JVABRYMGSQEGCI-UHFFFAOYSA-N 0.000 claims 1
- KDRZCUHCWMPVJJ-UHFFFAOYSA-N 4-(3-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine-6-carbonitrile Chemical compound N=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=C(Cl)C=CC=[N+]1[O-] KDRZCUHCWMPVJJ-UHFFFAOYSA-N 0.000 claims 1
- HLCLEQJHXATLGE-UHFFFAOYSA-N 4-(3-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-6-(trifluoromethyl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(C(F)(F)F)C=C2C=1C1=C(Cl)C=CC=[N+]1[O-] HLCLEQJHXATLGE-UHFFFAOYSA-N 0.000 claims 1
- DZZFCEHDAYKIQQ-UHFFFAOYSA-N 4-(3-ethoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine-6-carbonitrile Chemical compound CCOC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(C#N)C=C12 DZZFCEHDAYKIQQ-UHFFFAOYSA-N 0.000 claims 1
- ONSHYLCMAFJWTO-UHFFFAOYSA-N 4-(3-methoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine-6-carbonitrile Chemical compound COC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(C#N)C=C12 ONSHYLCMAFJWTO-UHFFFAOYSA-N 0.000 claims 1
- DZEGBNZOQUCKBX-UHFFFAOYSA-N 4-(3-methoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-6-(trifluoromethyl)-1,3-benzoxazine Chemical compound COC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(C(F)(F)F)C=C12 DZEGBNZOQUCKBX-UHFFFAOYSA-N 0.000 claims 1
- FXNJYSMGYBVHTC-UHFFFAOYSA-N 6,7-dibromo-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC(Br)=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] FXNJYSMGYBVHTC-UHFFFAOYSA-N 0.000 claims 1
- XQMJSHWOJKPOPQ-UHFFFAOYSA-N 6,7-dichloro-2,2-dimethyl-4-pyridin-2-yl-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC(Cl)=C(Cl)C=C2C=1C1=CC=CC=N1 XQMJSHWOJKPOPQ-UHFFFAOYSA-N 0.000 claims 1
- ZHSMBZWIDJSZMJ-UHFFFAOYSA-N 6-bromo-2,2,7-trimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound C1=2C=C(Br)C(C)=CC=2OC(C)(C)N=C1C1=CC=CC=[N+]1[O-] ZHSMBZWIDJSZMJ-UHFFFAOYSA-N 0.000 claims 1
- VXMORWXLIPEOEL-UHFFFAOYSA-N 6-bromo-2,2-dimethyl-4-(1-oxidoquinolin-1-ium-2-yl)-1,3-benzoxazine Chemical compound C1=CC=CC2=[N+]([O-])C(C=3C4=CC(Br)=CC=C4OC(N=3)(C)C)=CC=C21 VXMORWXLIPEOEL-UHFFFAOYSA-N 0.000 claims 1
- OGHPASXBBGKWHV-UHFFFAOYSA-N 6-bromo-2,2-dimethyl-4-(3-methyl-1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound CC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(Br)C=C12 OGHPASXBBGKWHV-UHFFFAOYSA-N 0.000 claims 1
- SSDFIHTWYIHLGA-UHFFFAOYSA-N 6-bromo-4-(3-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(Br)C=C2C=1C1=C(Cl)C=CC=[N+]1[O-] SSDFIHTWYIHLGA-UHFFFAOYSA-N 0.000 claims 1
- PFLBPRVQSZPSLB-UHFFFAOYSA-N 6-bromo-4-(3-ethoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine Chemical compound CCOC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(Br)C=C12 PFLBPRVQSZPSLB-UHFFFAOYSA-N 0.000 claims 1
- KHCSDIDXQAWQDH-UHFFFAOYSA-N 6-bromo-4-(3-methoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine Chemical compound COC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC=C(Br)C=C12 KHCSDIDXQAWQDH-UHFFFAOYSA-N 0.000 claims 1
- YUEQBWZPZJXBHY-UHFFFAOYSA-N 6-bromo-7-chloro-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC(Cl)=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] YUEQBWZPZJXBHY-UHFFFAOYSA-N 0.000 claims 1
- MLWOFWWQPNBFSW-UHFFFAOYSA-N 6-bromo-7-chloro-2,2-dimethyl-4-(3-methyl-1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound CC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC(Cl)=C(Br)C=C12 MLWOFWWQPNBFSW-UHFFFAOYSA-N 0.000 claims 1
- MFZZKXIAKOMRCM-UHFFFAOYSA-N 6-bromo-7-chloro-4-(3-ethoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine Chemical compound CCOC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC(Cl)=C(Br)C=C12 MFZZKXIAKOMRCM-UHFFFAOYSA-N 0.000 claims 1
- MBJWROYHAFSALT-UHFFFAOYSA-N 6-bromo-7-chloro-4-(3-methoxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-1,3-benzoxazine Chemical compound COC1=CC=C[N+]([O-])=C1C1=NC(C)(C)OC2=CC(Cl)=C(Br)C=C12 MBJWROYHAFSALT-UHFFFAOYSA-N 0.000 claims 1
- IELJHOSIPYSPDL-UHFFFAOYSA-N 6-chloro-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(Cl)C=C2C=1C1=CC=CC=[N+]1[O-] IELJHOSIPYSPDL-UHFFFAOYSA-N 0.000 claims 1
- OLRSODNTAYIBAU-UHFFFAOYSA-N 6-ethynyl-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound N=1C(C)(C)OC2=CC=C(C#C)C=C2C=1C1=CC=CC=[N+]1[O-] OLRSODNTAYIBAU-UHFFFAOYSA-N 0.000 claims 1
- LLYUCYUABMDRQA-UHFFFAOYSA-N 7-chloro-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine-6-carbonitrile Chemical compound N=1C(C)(C)OC2=CC(Cl)=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] LLYUCYUABMDRQA-UHFFFAOYSA-N 0.000 claims 1
- HFVOUCSDHKGIBX-UHFFFAOYSA-N 7-fluoro-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine-6-carbonitrile Chemical compound N=1C(C)(C)OC2=CC(F)=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] HFVOUCSDHKGIBX-UHFFFAOYSA-N 0.000 claims 1
- NZBAASHAIHSYPP-UHFFFAOYSA-N 7-methoxy-2,2-dimethyl-6-nitro-4-(1-oxidopyridin-1-ium-2-yl)-1,3-benzoxazine Chemical compound C1=2C=C([N+]([O-])=O)C(OC)=CC=2OC(C)(C)N=C1C1=CC=CC=[N+]1[O-] NZBAASHAIHSYPP-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 240000006162 Chenopodium quinoa Species 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 1
- 235000012054 meals Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 하기 일반 구조식 (Ⅰ)의 1,3-벤족사직 유도체 또는 그의 염.(Ⅰ)[상기 식중에서는 임의적으로 치환된 벤젠고리이며; R1은 탄소-탄소 결합을 통하여 1,3-벤족사진 고리의 4-위치에 결합된 카르보시클릭 또는 헤테로시클릭기, 탄화수소 잔기 또는 구조식;(식중에서, R4는 수소원자, C1-4알킬기 또는 C1-4알킬카르보닐기이고; Y는 -S-, -O-, 또는 구조식;(식중에서 R6은 수소원자, C1-4알킬 또는 C1-11아실기이다)의 Z는 =N-CN-=N-NO2또는 =CH-NO2이고;R5는 수소원자 또는 C1-8알킬 기이거나, R4및 R5는 함께 결합하여 C3-6알킬렌기 또는 C3-6알킬렌 카르보닐기를 형성하거나 R5및 R6은 함께 결합하여 C4-5알킬렌기를 형성한다)의 기이고, 카르보시클릭 또는 헤테로시 클릭기 및 탄화수소 잔기는 임의적으로 치환될 수 있고; R2및 R3는 독립적으로 수소원자 또는 임의적으로 치환된 C1-6알킬기이거나, R2및 R3는 함께 결합하여 임의적으로 치환된 C3-6알킬렌기를 형성한다]
- 제1항에 있어서, 하기 일반식 구조식 (Ⅰa)로 나타내어지는 화합물.(Ⅰa)[상기 식중에서, R1, R2및 R3는 제1항에서 정의한 바와 같으며; R' 및 R＂는 독립적으로 수소원자, 히드록실기, 할로겐원자, 니트로기, 시아노기, 임의적으로 치환된 C1-6알킬기, 임의적으로 치환된 C1-6알콕시기, 임의적으로 치환된 C2-6알케닐기, 임의적으로 치환된 에티닐기, 임의적으로 치환된 아릴기, 임의적으로 치환된 헤테로아릴기, 임의적으로 치환된 아미노기,임의적으로 치환된 카르보닐기, 임의적으로 치환된 티오카르보닐기, 임의적으로 치환된 티오카르보닐옥시기, 임의적으로 치환된 아미노알킬기, 임의적으로 치환된 티오카르보닐, 옥시기, 임의적으로 치환된 아미노 알킬기, 임의적으로 치환된 메르캅토기, 임의적으로 치환된 술피닐기 또는 임의적으로 치환된 술포닐기이거나, R' 및 R＂는 함께 결합하여 -CH=CH-CH=CH- ( C1-4알킬, C1-4알콕시, 니트로, 할로겐, CF3, C1-4알콕시카르보닐 및 시아노로 구성된 군으로 부터 선택된 1내지 3개의 치환기로 임의적으로 치환된)=N-O-N=, (CH2)a-(식중에서 a는 3 또는 4이다). -(CH2)b-CO-, -(CH2)b-C(=(NOH)- 또는 -(CH2)b-C(=N-O-알킬)-(식들중에서 b는 2 또는 3이다)을 형성한다]
- 제2항에 있어서, R' 및 R＂가 메틸, 에틸, 아세틸, 프로피오닐, 벤조일 (메틸, 메톡시, 할로겐, 니트로, CF3, 또는 시아노로 임의적으로 치환된다), 메톡시, 에톡시, 메톡시카르보닐, 에톡시카르보닐, 아세톡시, 프로피옥시, 프로폭시카르보닐, 부틸옥시카르보닐, 이소부틸옥시카르보닐, 1-히드록시에틸, 1-히드록시벤질, 메틸술포닐, 에틸술피닐, 벤젠술피닐(메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메틸술포닐, 에틸술피닐, 벤젠술피닐(메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메톡시술피닐, 에톡시술피닐, 메톡시술포닐, 에톡시술포닐, 아세트아미도, 프로피온아미도, 벤조아미도(메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메톡시카르보닐아미도, 에톡시카르보닐아미도,티오아세틸, 티오프로피오닐, 티오벤조일 (메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메톡시티오카르보닐, 에톡시티오카르보닐, 티오노아세톡시, 티오노프로피온옥시, 1-메르캅토에 틸, 1-메르캅토벤질, 메틸술피닐아미노, 에틸술피닐아미노, 벤젠술피닐아미노 (메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메틸술포닐아미노, 에틸술포닐아미노, 벤젠술포닐아미노(메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메톡시술피닐아미노, 에톡시술피닐아미노, 에톡시술피닐아미노,메톡시술포닐아미노, 에톡시술포닐아미노, 1-프로페닐, 스티릴 (메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), 메톡시아미노메틸, 에톡시아미노메틸, 1-(히드록시이미노)에틸, 1-(하드록시이미노), 프로필, 1-히드라지노에틸, 1-히드라지노프로필, 1-프로피닐, CF3, CF3CF2, CF3O, HCF3O, CF2=CF, 니트로, 시아노, 할로겐, 아미노, 포르밀, 로픔아미도, 히드록시아미노메틸, CO2H, CONN2, SH, CF3S, 티오포름 아미도, CSNH2, SO2NH2, 2-옥소프로필, 2-옥소부틸, 3-옥소부필, 3-옥소펜틸, 니트로메틸, 1-니트로에틸, -니트로에틸, 비닐, 니트로비닐, 시아노비닐, 트리플루오로비닐, 에티닐 또는 (CH3)3SIC=C인 화합물.
- 제2항에 있어서, R' 또는 R＂가 메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환되는 푸릴, 티에닐, 피롤릴, 옥사졸릴, 티아졸릴, 아미다졸릴, 옥사디아졸릴, 티아디아졸릴, 피리딜, 피리다지닐, 피리미디닐, 피라지닐 또는 트라이지닐인 화합물.
- 제2항에 있어서, R' 또는 R＂는 함께 결합하여 -CH=CH-CH=CH- (메틸, 메톡시, 할로겐, 니트로, CF3또는 시아노로 임의적으로 치환된다), =N-O-N=, -(CH2)3-, -(CH2)4-, -(CH2)2CO-, -(CH2)3CO-, -(CH2)2C(=NOH)-, -(CH2)2C(=NOCH3)-, -(CH2)3C(=NOH) -또는 (CH2)3C(=NOCH3)-를 형성하는 화합물.
- 제2항에 있어서, R1은 히드록시, C1-6알콕시, C1-6알킬 또는 할로겐으로 임의적으로 치환된 2-피리딜히드록시, C1-6알콕시, C1-6알킬 또는 할로겐으로 임의적으로 치환된 피리딘-N-옥사이드-2-일, 2-퀴놀릴, 퀴놀린-N-옥사이드-2-일 또는 1-메틸-2-옥소-3-피로리디닐인 화합물.
- 제2항에 있어서, R1이 3-메틸-1-(하아노 또는 니트로)-구아니디노, 3,3-디메틸-2-(시아노 또는 니트로)-구아니디노, 3-(t-부틸)-2-(시아노 또는 니트로)-구아니디노, 3-(1,2,2-트리메틸프로필)-2-(시아노 또는 니트로)-구아니디노, 3-이소프로필-2-(시아노 또는 니트로)-구아니디노, 3-시클로프로필 -2-(시아노 또는 니트로)-구아니디오, 3,3-테트라메틸렌-2-(시아노 또는 니트로)-구아니디노,3,3-펜타메틸렌-2-(시아노 또는 니트로)-구아니디노,(1-메틸아미노-2-니트로에테닐)아미노,(1-이소프로필아미노-2-니트로에테닐)아미노, 2-메틸-3-(시아노 또는 니트로)-1-이소티오우레이도, (1-메틸티오-2-니트에테닐)아미노, 2-메틸-3-(시아노 또는 니트로)-1-이소우레이도, 2-에틸-3-(시아노 또는 니트로)-1-이소우레이도, (1-메톡시-2-니트로에테닐)아미노, (1-에톡시-2-니트로에테닐)아미노, 2-시아노미노-이미다졸리딘-1-일, 2-니트로아미노-이미다졸린-1-일, 2-(시아노이미노 또는 니트로이미노)-헥사히드로피리미딘-1-일, 2-니트로에테닐이미다졸리딘-1-일, 2-니트로에테닐-헥사히드로피리미딘-1-일, 2-(시아노이미노 또는 니트로이미노)-티아졸리딘-3-일, 2-니트로에테닐-티아졸리딘-3-일, 2-(시아노이미노 또는 니트로이미노)-옥사졸리딘-3-일, 2-니트로에테닐-옥사졸리딘-3-일, 또는 2-(시아노 또는 니트로)-크레아티닌-3-일인 화합물.
- 제2항에 있어서, R2및 R3가 각각 메틸, 에틸 또는 프로필인 화합물.
- 제2항에 있어서, R2및 R3가 함께 결합하여 시클로프로필, 시클로펜틸 또는 시클로헥실을 형성하는 화합물.
- 제1항에 있어서, 2,2-디메틸-4-(2-피리딜)-2H-1,3-벤족사진, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘N-옥사이드, 2-(2,2-디메틸-6-니이트-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-아세틸-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드,2-(6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-에티닐-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-브로모-2,2,7-트리메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(2,2,7-트리메틸-6-니트로-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드,2-(6-시아노-2,2,7-트리메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-16-시아노-7-메톡시-2,2-디메틸-2H-1,3-벤족사진-4-일), 2-(6-피리딘N-7-메톡시-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(7-메톡시-2,2-디메틸-6-니트로-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-브로모-7-플루오로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-브로모-7-플루오로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-시아노-7-플루오로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(7-플루오로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-트리플루오로메틸-2,2-디메틸--옥사이드-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-트리플루오로메틸-2,2-디메틸-옥사이드-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-펜타플루오로에틸-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-트리플루오로비닐-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6,7-디클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-브로모-7-클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(7-클로로-6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6,7-디브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(2,2-디메틸-2H-나프토[2,3-e][옥사진-4-일)피리딘 N-옥사이드, 2-(6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-에톡시피리딘- N-옥사이드,6-시아노-2,2-디메틸-4-(1-메틸--옥소-3-피롤리디닐)-2H-1,3-벤족사진, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)퀴놀린 N-옥사이드, 2-(6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메톡시피리딘 N-옥사이드, 2-(6-디메틸-2H-1,3-벤족사진-4-일)-3-메틸피리딘 N-옥사이드, 3-클로로-2-(6-시아노-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메톡시피리딘 N-옥사이드, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-에톡시피리딘 N-옥사이드, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메틸피리딘 N-옥사이드, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-클로로피리딘 N-옥사이드, 2-(6-브로모-7-클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메톡시피리딘 N-옥사이드, 2-(6-브로모-7-클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-에토시피리딘 N-옥사이드, 2-(6-브로모-7-클로로-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메틸피리딘 N-옥사이드, 2-(6-트리플루오로메틸-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메톡시피리딘N-옥사이드,2-(6-트리플루오로메-2,2-디메틸-2H-1,3-벤족사진-4-일)-3-메톡시피리딘 N-옥사이드, 또는 클로로-2-(6-트리플루오로메틸-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드인 화합물.
- 제1항에 있어서, 2-(6-브로모-2,2-디메틸-2H-1,3-벤족사진-4-일)피리딘 N-옥사이드인 화합물.
- 하기 일반식 구조식(Ⅱ)의 화합물 또는 그의 염을 하기 일반 구조식(Ⅳ)의 화합물로 반응시키는 것을 특징으로 하는 제1항에 따른 일반 구조식(Ⅰ)의 화합물 그의 염의 제조방법.(Ⅱ)[상기 식중에서, E는 할로겐원자 또는 에스테로화 히드록실기이고 다른 부호는 상기 정의한 바와같다]R1'-M (Ⅳ)[상기 식중에서, R1'는 그의 탄소원자를 통하에 기 M에 결합되는 카르보시클릭 또는 헤테로시클릭기, 탄화수소 잔기 또는 구조식 ;(식중에서, R4는 수소원자, C1-4알킬기 또는 C1-4알킬카르보닐기이고; Y는 -S-, -O-, 또는 구조식(식중에서, R6은 수소원자, C1-4알킬 또는 C1-11아실이다)의 기이고 ;Z는 N-CN, =N-NO2또는 =CH-NO2이고 ; R6는 수소원자 또는 C1-6알킬기이거나 R4및 R5은 함께 결합하여 C3-6알킬렌기 또는 C3-6알킬렌 카르보닐기를 형성하거나, R5및 R6은 함께 결합하여 C4-5알킬렌기를 형성한다).의 기이고, 카르보시클릭기 또는 헤테로시클릭 및 탄화수소 잔기는 임의적으로 치환될 수 있으며, M은 이탈기이다]
- 하기 일반 구조식(Ⅶ)의 화합물을 하기 일반 구조식(Ⅶ) 또는 (Ⅶ')화합물 또는 그의 염과 반응시키는 것을 특징으로 하는 제1항에 따른 일반 구조식(Ⅰ)의 화합물 또는 그의 염의 제조방법.(Ⅶ)[상기식중에서, 각 부호는 상기 정의한 바와 같다]또는[상기 식중에서, R은 메틸 또는 에틸기이며, 다른 부호는 제1항에서 정의한 바와 같다]
- 하기 일반 구조식 (Ⅸ)의 화합물 또는 그의 염을 제13항에 정의된 일반 구조식(Ⅷ) 또는 (Ⅷ')의 화합물 및 암모니아와 반응시키는 것을 특징으로 하는 제1항에 따른 일반구조식(Ⅰ)의 화합물 또는 그의 염의 제조방법.(Ⅸ)[상기 식중에서, 각각의 부호는 제1항에 정의된 바와같다]
- 제1항에 따른 구조식(Ⅰ)의 화합물 또는 그의 염을 함유하는 강압제.
- 유효량의 제1항에 따른 구조식(Ⅰ)의 화합물 또는 그의 염을 임의적으로 제약학적으로 허용가능한 담체, 희석제 또는 부형제와 함께 고혈압 환자에게 투여하는 것을 특징으로 하는 고혈압 치료방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP90-256478 | 1990-09-25 | ||
| JP25647890 | 1990-09-25 | ||
| JP90-417050 | 1990-12-28 | ||
| JP41705090 | 1990-12-28 | ||
| JP91-076742 | 1991-03-15 | ||
| JP7674291 | 1991-03-15 | ||
| JP20423591 | 1991-08-14 | ||
| JP91-204235 | 1991-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920006336A true KR920006336A (ko) | 1992-04-27 |
Family
ID=27465972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910016710A KR920006336A (ko) | 1990-09-25 | 1991-09-25 | 1,3-벤족사진 유도체, 그의 제조방법 및 용도 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5270308A (ko) |
| EP (1) | EP0477789A1 (ko) |
| KR (1) | KR920006336A (ko) |
| CN (1) | CN1060467A (ko) |
| AU (1) | AU640820B2 (ko) |
| CA (1) | CA2052145A1 (ko) |
| CS (1) | CS293291A3 (ko) |
| FI (1) | FI914487A (ko) |
| HU (1) | HUT62003A (ko) |
| IE (1) | IE913186A1 (ko) |
| IL (1) | IL99474A0 (ko) |
| NO (1) | NO913745L (ko) |
| PL (1) | PL291823A1 (ko) |
| PT (1) | PT99030A (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0522606B1 (en) * | 1991-05-10 | 1996-04-03 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| ATE191716T1 (de) * | 1992-08-17 | 2000-04-15 | Chugai Pharmaceutical Co Ltd | Benzopyran und benzoxazin-derivate |
| GB9309716D0 (en) * | 1993-05-12 | 1993-06-23 | Zeneca Ltd | Heterocyclic derivatives |
| JP3814742B2 (ja) * | 1996-10-18 | 2006-08-30 | イハラケミカル工業株式会社 | ４−フルオロサリチル酸類 |
| US6593335B1 (en) * | 1997-12-18 | 2003-07-15 | Abbott Laboratories | Potassium channel openers |
| US6265417B1 (en) * | 1997-12-18 | 2001-07-24 | Abbott Laboratories | Potassium channel openers |
| US6455554B1 (en) | 1999-06-07 | 2002-09-24 | Targacept, Inc. | Oxopyridinyl pharmaceutical compositions and methods for use |
| US6538004B2 (en) * | 2000-03-03 | 2003-03-25 | Abbott Laboratories | Tricyclic dihydropyrazolone and tricyclic dihydroisoxazolone potassium channel openers |
| CA2537746A1 (en) * | 2003-09-04 | 2005-03-17 | Poseidon Pharmaceuticals A/S | Erg channel openers for the treatment of cardiac arrhythmias |
| WO2006002470A1 (en) * | 2004-06-30 | 2006-01-12 | Monash University | Chiral ligands for asymmetric catalysis |
| US8258131B2 (en) * | 2007-08-01 | 2012-09-04 | Mitsubishi Tanabe Pharma Corporation | Fused bicyclic compound |
| US8383706B2 (en) | 2009-06-05 | 2013-02-26 | 3M Innovative Properties Company | Benzoxazine-thiol adducts |
| US8389758B2 (en) | 2009-06-05 | 2013-03-05 | 3M Innovative Properties Company | Benzoxazine-thiol adducts |
| ME02847B (me) | 2009-07-27 | 2018-01-20 | Gilead Sciences Inc | Fuzionisana heterociklična jedinjenja kao modulatori jonskih kanala |
| CA2802288C (en) | 2010-07-02 | 2018-08-21 | Gilead Sciences, Inc. | Triazolopyridinone compounds as ion channel modulators |
| NZ617987A (en) | 2011-05-10 | 2016-02-26 | Gilead Sciences Inc | Fused heterocyclic compounds as sodium channel modulators |
| NO3175985T3 (ko) | 2011-07-01 | 2018-04-28 | ||
| TWI478908B (zh) | 2011-07-01 | 2015-04-01 | Gilead Sciences Inc | 作為離子通道調節劑之稠合雜環化合物 |
| ITMI20122221A1 (it) * | 2012-12-21 | 2014-06-22 | C4T S C A R L | Nuovi composti del 2,3-diidro-4h-1,3-benzossazin-4-one, metodo per prepararli e forma farmaceutica che li comprende |
| CN109336781A (zh) * | 2018-12-12 | 2019-02-15 | 湖南海利常德农药化工有限公司 | 一种水杨腈的纯化方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2321496A1 (de) | 1973-04-27 | 1974-11-14 | Nii Farmakol Akad Med | 2-aminomethyl-4,4-dialkyl-4h-1,3-benzoxazine, deren salze und verfahren zu ihrer herstellung |
| JPS57130979A (en) | 1981-02-09 | 1982-08-13 | Sankyo Co Ltd | 4-amino-1,3-benzoxazine derivative and its preparation |
| ZM7682A1 (en) | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| GB2107706A (en) * | 1981-09-25 | 1983-05-05 | Beecham Group Plc | Benzopyrans |
| US4971982A (en) * | 1987-07-06 | 1990-11-20 | Hoffmann-La Roche Inc. | Benzopyran derivatives |
| US5021432A (en) | 1988-04-26 | 1991-06-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyran compound and its pharmaceutical use |
| DE3840011A1 (de) | 1988-11-26 | 1990-05-31 | Merck Patent Gmbh | Benzoxazinderivate |
| TW224941B (ko) * | 1989-11-08 | 1994-06-11 | Yamanouchi Pharma Co Ltd |
-
1991
- 1991-02-25 CN CN91109186A patent/CN1060467A/zh active Pending
- 1991-09-10 IE IE318691A patent/IE913186A1/en unknown
- 1991-09-13 IL IL99474A patent/IL99474A0/xx unknown
- 1991-09-20 EP EP19910116002 patent/EP0477789A1/en not_active Withdrawn
- 1991-09-24 AU AU84748/91A patent/AU640820B2/en not_active Ceased
- 1991-09-24 FI FI914487A patent/FI914487A/fi not_active Application Discontinuation
- 1991-09-24 CA CA002052145A patent/CA2052145A1/en not_active Abandoned
- 1991-09-24 HU HU913050A patent/HUT62003A/hu unknown
- 1991-09-24 NO NO91913745A patent/NO913745L/no unknown
- 1991-09-24 PT PT99030A patent/PT99030A/pt not_active Application Discontinuation
- 1991-09-25 KR KR1019910016710A patent/KR920006336A/ko not_active Application Discontinuation
- 1991-09-25 CS CS912932A patent/CS293291A3/cs unknown
- 1991-09-25 US US07/764,692 patent/US5270308A/en not_active Expired - Fee Related
- 1991-09-25 PL PL29182391A patent/PL291823A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2052145A1 (en) | 1992-03-26 |
| US5270308A (en) | 1993-12-14 |
| NO913745L (no) | 1992-03-26 |
| IE913186A1 (en) | 1992-02-25 |
| CS293291A3 (en) | 1992-08-12 |
| AU640820B2 (en) | 1993-09-02 |
| EP0477789A1 (en) | 1992-04-01 |
| NO913745D0 (no) | 1991-09-24 |
| CN1060467A (zh) | 1992-04-22 |
| PT99030A (pt) | 1992-09-30 |
| IL99474A0 (en) | 1992-08-18 |
| HUT62003A (en) | 1993-03-29 |
| FI914487A (fi) | 1992-03-26 |
| AU8474891A (en) | 1992-04-02 |
| PL291823A1 (en) | 1992-08-24 |
| FI914487A0 (fi) | 1991-09-24 |
| HU913050D0 (en) | 1992-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920006336A (ko) | 1,3-벤족사진 유도체, 그의 제조방법 및 용도 | |
| KR102001910B1 (ko) | 항암제의 나이트로벤질 유도체 | |
| CA1212946A (en) | Chromans and chromenes | |
| KR950004004B1 (ko) | 신규한 벤조피리도 피페리딘, 피페리딜리덴 및 피페라진 화합물, 조성물, 제조방법 및 이용방법 | |
| KR910011859A (ko) | 질소-함유 스피로사이클 | |
| KR920021514A (ko) | 피리딘 유도체, 이의 제법 및 용도 | |
| MXPA06003340A (es) | Derivados de isoquinolina 1,4-disustituida como inhibidores raf-quinasa utiles para el tratamiento de enfermedades proliferativas. | |
| KR830007628A (ko) | 2,4-디아미노-5(치환된)피리미딘의 제조방법 및 이것의 제약학적 조성물 | |
| KR890005089A (ko) | 콜레스테롤 생합성의6-[[(치환된)피리딘-3-일]알킬]- 및 알켄일] 테트라하이드로-4-하이드록시피란-2-온 억제제 | |
| CA2560489A1 (en) | Pyranone compounds useful to treat retroviral infections | |
| KR910015569A (ko) | 피페리딘화합물, 이의 제법 및 이의 용도 | |
| JPH05170740A (ja) | Ｈｉｖ逆転写酵素のヒドロキシル化阻害剤 | |
| KR880000421A (ko) | 벤조피란 유도체 및 이의 제조방법 | |
| KR960017658A (ko) | 알파₁-아드레날린수용체 길항물질로서의 [3-(4-페닐피페라진-1-일)프로필-아미노, 티오 및 옥시］-피리딘, 피리미딘 및 벤젠 유도체 | |
| KR830005140A (ko) | 피페리딘 유도체의 제조방법 | |
| US5273977A (en) | Substituted tetrahydropyridines and hydroxypiperidines as central nervous system agents | |
| KR910004592A (ko) | 벤조피란 화합물, 그의 제조방법 및 약학 조성물 | |
| US5874446A (en) | Benzopyran derivatives | |
| Gao et al. | Synthesis of daidzin analogues as potential agents for alcohol abuse | |
| CA2064796A1 (en) | Antiatherosclerotic and antithrombotic 2-amino-6-phenyl-4h-pyran-4-ones | |
| JPS5867683A (ja) | 活性化合物、その製法およびそれを含む医薬組成物 | |
| US4115567A (en) | 6-Carboxy-2-(2'-pyrazinyl)-chromones and esters thereof | |
| EP0288077A2 (en) | Synthetic flavonoids as inhibitors of leukotrienes and 5-lipoxygenase | |
| KR900003175A (ko) | 벤조피라놀 유도체 | |
| KR910009708A (ko) | 4-아미디노 크로만 및 4-아미디노 피라노 (3,2-c)피리딘 유도체, 그의 제조방법 및 그를 함유하는 약학 조성물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |