NO313325B1 - Nitrometyltiobenzenderivater, fremgangsmåter for fremstilling derav, farmasöytisk preparat og anvendelse av forbindelsene tilfremstilling av et medisinsk produkt - Google Patents
Nitrometyltiobenzenderivater, fremgangsmåter for fremstilling derav, farmasöytisk preparat og anvendelse av forbindelsene tilfremstilling av et medisinsk produkt Download PDFInfo
- Publication number
- NO313325B1 NO313325B1 NO19993082A NO993082A NO313325B1 NO 313325 B1 NO313325 B1 NO 313325B1 NO 19993082 A NO19993082 A NO 19993082A NO 993082 A NO993082 A NO 993082A NO 313325 B1 NO313325 B1 NO 313325B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- dimethyl
- nitromethyl
- sulfonyl
- mmol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 72
- 238000000034 method Methods 0.000 title claims description 66
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 7
- 229940127554 medical product Drugs 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- GJGUOMBYPKDBSS-UHFFFAOYSA-N nitromethylsulfanylbenzene Chemical class [O-][N+](=O)CSC1=CC=CC=C1 GJGUOMBYPKDBSS-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 208
- -1 trifluoromethoxy, methylsulfonyl Chemical group 0.000 claims description 68
- 239000000243 solution Substances 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- FIMPGOJEDMNMHL-UHFFFAOYSA-N 3,5-dimethyl-4-(nitromethylsulfonyl)aniline Chemical compound CC1=CC(N)=CC(C)=C1S(=O)(=O)C[N+]([O-])=O FIMPGOJEDMNMHL-UHFFFAOYSA-N 0.000 claims description 39
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000005504 styryl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 102000016912 Aldehyde Reductase Human genes 0.000 claims description 5
- 108010053754 Aldehyde reductase Proteins 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- PZYGYFBOCPONPP-UHFFFAOYSA-N (4-acetamido-2,6-dimethylphenyl) thiocyanate Chemical compound CC(=O)NC1=CC(C)=C(SC#N)C(C)=C1 PZYGYFBOCPONPP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000013270 controlled release Methods 0.000 claims description 3
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- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- IRLWRLLWESICPB-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-2-fluorobenzenesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)C=2C(=CC=CC=2)F)=C1 IRLWRLLWESICPB-UHFFFAOYSA-N 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
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- 208000002177 Cataract Diseases 0.000 claims description 2
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- SHRORAORPQUSNY-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-1-phenylmethanesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)CC=2C=CC=CC=2)=C1 SHRORAORPQUSNY-UHFFFAOYSA-N 0.000 claims description 2
- BVQZQVBKCAYFSL-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-2,3-difluorobenzenesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)C=2C(=C(F)C=CC=2)F)=C1 BVQZQVBKCAYFSL-UHFFFAOYSA-N 0.000 claims description 2
- UVXAOQFREITLLV-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-4-fluorobenzenesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)C=2C=CC(F)=CC=2)=C1 UVXAOQFREITLLV-UHFFFAOYSA-N 0.000 claims description 2
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- 239000007800 oxidant agent Substances 0.000 claims description 2
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
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- XHRNWLQQVSYTDD-UHFFFAOYSA-N [Na].C[N+]([O-])=O Chemical compound [Na].C[N+]([O-])=O XHRNWLQQVSYTDD-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- OFYKMIGWZMESCD-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-3-fluorobenzenesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)C=2C=C(F)C=CC=2)=C1 OFYKMIGWZMESCD-UHFFFAOYSA-N 0.000 claims 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
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- 238000001816 cooling Methods 0.000 description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
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- ZMJILEMBCVCKSR-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-4-methylsulfonylbenzenesulfonamide Chemical compound CC1=C(S(=O)(=O)C[N+]([O-])=O)C(C)=CC(NS(=O)(=O)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 ZMJILEMBCVCKSR-UHFFFAOYSA-N 0.000 description 1
- ZAISHMPLTWBHCF-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]methanesulfonamide Chemical compound CC1=CC(NS(C)(=O)=O)=CC(C)=C1S(=O)(=O)C[N+]([O-])=O ZAISHMPLTWBHCF-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- ADKLJTCVZHUANG-UHFFFAOYSA-N nitromethylsulfonylbenzene Chemical class [O-][N+](=O)CS(=O)(=O)C1=CC=CC=C1 ADKLJTCVZHUANG-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RZJLHJFNHJKOAZ-UHFFFAOYSA-N sodium;methylidene(dioxido)azanium Chemical compound [Na+].[O-][N+]([O-])=C RZJLHJFNHJKOAZ-UHFFFAOYSA-N 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 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
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9615887A FR2757509B1 (fr) | 1996-12-23 | 1996-12-23 | Nouveaux derives de sulfonamides et sulfonylurees, leurs preparations et medicaments les contenant |
| PCT/EP1997/006981 WO1998028265A1 (fr) | 1996-12-23 | 1997-12-12 | Derives du nitromethylthiobenzene comme inhibiteurs de l'aldose reductase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993082D0 NO993082D0 (no) | 1999-06-22 |
| NO993082L NO993082L (no) | 1999-08-20 |
| NO313325B1 true NO313325B1 (no) | 2002-09-16 |
Family
ID=9499031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993082A NO313325B1 (no) | 1996-12-23 | 1999-06-22 | Nitrometyltiobenzenderivater, fremgangsmåter for fremstilling derav, farmasöytisk preparat og anvendelse av forbindelsene tilfremstilling av et medisinsk produkt |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6509499B1 (es) |
| EP (1) | EP0946503B1 (es) |
| JP (1) | JP2001507001A (es) |
| KR (1) | KR20000069678A (es) |
| CN (1) | CN1112356C (es) |
| AT (1) | ATE215069T1 (es) |
| AU (1) | AU728562B2 (es) |
| BR (1) | BR9714069A (es) |
| CA (1) | CA2275665A1 (es) |
| CZ (1) | CZ227799A3 (es) |
| DE (1) | DE69711429T2 (es) |
| DK (1) | DK0946503T3 (es) |
| ES (1) | ES2172829T3 (es) |
| FR (1) | FR2757509B1 (es) |
| HU (1) | HUP0002054A3 (es) |
| ID (1) | ID22073A (es) |
| NO (1) | NO313325B1 (es) |
| PL (1) | PL334188A1 (es) |
| PT (1) | PT946503E (es) |
| RU (1) | RU2184110C2 (es) |
| SK (1) | SK282820B6 (es) |
| TR (1) | TR199901442T2 (es) |
| UA (1) | UA56205C2 (es) |
| WO (1) | WO1998028265A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2884820B1 (fr) * | 2005-04-25 | 2007-07-27 | Merck Sante Soc Par Actions Si | Nouveaux inhibiteurs specifiques de la caspase-10 |
| US8158667B2 (en) | 2006-08-21 | 2012-04-17 | Kador Peter F | Topical treatment of cataracts in dogs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8718619D0 (en) * | 1987-08-06 | 1987-09-09 | Ici Plc | Pharmaceutical compositions |
| IE63463B1 (en) | 1989-02-06 | 1995-04-19 | Zeneca Ltd | Phenylsulphone derivatives |
| GB9016984D0 (en) | 1990-08-02 | 1990-09-19 | Ici Plc | Aniline derivatives |
| US5250570A (en) | 1990-08-02 | 1993-10-05 | Imperial Chemical Industries Plc | Amidobenzene derivatives, compositions and use |
| GB9016980D0 (en) * | 1990-08-02 | 1990-09-19 | Ici Plc | Amidobenzenes |
| GB9016978D0 (en) | 1990-08-02 | 1990-09-19 | Ici Plc | Acetamide derivatives |
-
1996
- 1996-12-23 FR FR9615887A patent/FR2757509B1/fr not_active Expired - Fee Related
-
1997
- 1997-12-12 CA CA002275665A patent/CA2275665A1/en not_active Abandoned
- 1997-12-12 RU RU99115476/04A patent/RU2184110C2/ru not_active IP Right Cessation
- 1997-12-12 PL PL97334188A patent/PL334188A1/xx unknown
- 1997-12-12 CN CN97180948A patent/CN1112356C/zh not_active Expired - Fee Related
- 1997-12-12 CZ CZ992277A patent/CZ227799A3/cs unknown
- 1997-12-12 DE DE69711429T patent/DE69711429T2/de not_active Expired - Fee Related
- 1997-12-12 ES ES97953797T patent/ES2172829T3/es not_active Expired - Lifetime
- 1997-12-12 WO PCT/EP1997/006981 patent/WO1998028265A1/fr not_active Application Discontinuation
- 1997-12-12 JP JP52831998A patent/JP2001507001A/ja active Pending
- 1997-12-12 EP EP97953797A patent/EP0946503B1/fr not_active Expired - Lifetime
- 1997-12-12 SK SK833-99A patent/SK282820B6/sk unknown
- 1997-12-12 UA UA99074125A patent/UA56205C2/uk unknown
- 1997-12-12 AU AU57571/98A patent/AU728562B2/en not_active Ceased
- 1997-12-12 US US09/331,662 patent/US6509499B1/en not_active Expired - Fee Related
- 1997-12-12 BR BR9714069-4A patent/BR9714069A/pt not_active IP Right Cessation
- 1997-12-12 KR KR1019997005722A patent/KR20000069678A/ko not_active Application Discontinuation
- 1997-12-12 AT AT97953797T patent/ATE215069T1/de not_active IP Right Cessation
- 1997-12-12 ID IDW990564A patent/ID22073A/id unknown
- 1997-12-12 DK DK97953797T patent/DK0946503T3/da active
- 1997-12-12 TR TR1999/01442T patent/TR199901442T2/xx unknown
- 1997-12-12 PT PT97953797T patent/PT946503E/pt unknown
- 1997-12-12 HU HU0002054A patent/HUP0002054A3/hu unknown
-
1999
- 1999-06-22 NO NO19993082A patent/NO313325B1/no not_active IP Right Cessation
-
2002
- 2002-11-12 US US10/291,677 patent/US20030203966A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FR2757509A1 (fr) | 1998-06-26 |
| CA2275665A1 (en) | 1998-07-02 |
| JP2001507001A (ja) | 2001-05-29 |
| EP0946503B1 (fr) | 2002-03-27 |
| US20030203966A1 (en) | 2003-10-30 |
| NO993082L (no) | 1999-08-20 |
| PT946503E (pt) | 2002-09-30 |
| CN1112356C (zh) | 2003-06-25 |
| ID22073A (id) | 1999-09-02 |
| CN1241997A (zh) | 2000-01-19 |
| FR2757509B1 (fr) | 1999-03-26 |
| NO993082D0 (no) | 1999-06-22 |
| RU2184110C2 (ru) | 2002-06-27 |
| EP0946503A1 (fr) | 1999-10-06 |
| ES2172829T3 (es) | 2002-10-01 |
| DE69711429D1 (en) | 2002-05-02 |
| CZ227799A3 (cs) | 1999-11-17 |
| SK282820B6 (sk) | 2002-12-03 |
| BR9714069A (pt) | 2000-05-09 |
| SK83399A3 (en) | 1999-12-10 |
| AU728562B2 (en) | 2001-01-11 |
| KR20000069678A (ko) | 2000-11-25 |
| TR199901442T2 (xx) | 1999-09-21 |
| DK0946503T3 (da) | 2002-06-10 |
| HUP0002054A2 (hu) | 2000-11-28 |
| HUP0002054A3 (en) | 2002-09-30 |
| AU5757198A (en) | 1998-07-17 |
| PL334188A1 (en) | 2000-02-14 |
| US6509499B1 (en) | 2003-01-21 |
| UA56205C2 (uk) | 2003-05-15 |
| ATE215069T1 (de) | 2002-04-15 |
| DE69711429T2 (de) | 2002-10-31 |
| WO1998028265A1 (fr) | 1998-07-02 |
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