ES2549603T3 - Derivados de fenol - Google Patents
Derivados de fenol Download PDFInfo
- Publication number
- ES2549603T3 ES2549603T3 ES10820564.2T ES10820564T ES2549603T3 ES 2549603 T3 ES2549603 T3 ES 2549603T3 ES 10820564 T ES10820564 T ES 10820564T ES 2549603 T3 ES2549603 T3 ES 2549603T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- mixture
- added
- benzothiazole
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 150000002989 phenols Chemical class 0.000 title abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 3
- -1 isopropylsulfanyl group Chemical group 0.000 abstract description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000002904 solvent Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- KKCAIWCKTFFCLT-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-methylsulfonylbenzonitrile Chemical compound N#CC1=C(O)C(S(=O)(=O)C)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 KKCAIWCKTFFCLT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 2
- ONAAASFKZAGAOC-UHFFFAOYSA-N 2-hydroxy-5-(1-oxo-2h-1,3-benzothiazole-3-carbonyl)-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(O)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)C1 ONAAASFKZAGAOC-UHFFFAOYSA-N 0.000 description 2
- UKIXFVDVIJMPOV-UHFFFAOYSA-N 2-methoxy-5-(1-oxo-2h-1,3-benzothiazole-3-carbonyl)-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(OC)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)C1 UKIXFVDVIJMPOV-UHFFFAOYSA-N 0.000 description 2
- MZBLSJKXXKWQEV-UHFFFAOYSA-N 2h-1,3-benzothiazol-3-yl-(3-chloro-5-iodo-4-methoxyphenyl)methanone Chemical compound C1=C(I)C(OC)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2SC1 MZBLSJKXXKWQEV-UHFFFAOYSA-N 0.000 description 2
- ZPDSIFBJCUZZGA-UHFFFAOYSA-N 3-chloro-5-iodo-4-methoxybenzoyl chloride Chemical compound COC1=C(Cl)C=C(C(Cl)=O)C=C1I ZPDSIFBJCUZZGA-UHFFFAOYSA-N 0.000 description 2
- DDGNGWBLULODLW-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-methoxy-3-methylsulfanylbenzonitrile Chemical compound C1=C(C#N)C(OC)=C(SC)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 DDGNGWBLULODLW-UHFFFAOYSA-N 0.000 description 2
- KSRNSGQVBKZINL-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-methoxy-3-methylsulfonylbenzonitrile Chemical compound C1=C(S(C)(=O)=O)C(OC)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 KSRNSGQVBKZINL-UHFFFAOYSA-N 0.000 description 2
- BRRWXKAWWWNKGN-UHFFFAOYSA-N 5-(2h-1,3-benzothiazole-3-carbonyl)-2-methoxy-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(OC)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2SC1 BRRWXKAWWWNKGN-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- YMGQPFUVBBSGQQ-UHFFFAOYSA-N methyl 3-chloro-4-hydroxy-5-iodobenzoate Chemical compound COC(=O)C1=CC(Cl)=C(O)C(I)=C1 YMGQPFUVBBSGQQ-UHFFFAOYSA-N 0.000 description 2
- GQPXYNMBPLSNQT-UHFFFAOYSA-N methyl 3-chloro-5-cyano-4-hydroxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(O)C(C#N)=C1 GQPXYNMBPLSNQT-UHFFFAOYSA-N 0.000 description 2
- SHHLWRDTDVUNTO-UHFFFAOYSA-N methyl 3-chloro-5-iodo-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C(I)=C1 SHHLWRDTDVUNTO-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- LDRNXZDCONMUSZ-UHFFFAOYSA-N (3,5-difluoro-4-methoxyphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(F)C(OC)=C(F)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 LDRNXZDCONMUSZ-UHFFFAOYSA-N 0.000 description 1
- WTDNIIPBZKOONK-UHFFFAOYSA-N (3-chloro-4-hydroxy-5-methylsulfanylphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound ClC1=C(O)C(SC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 WTDNIIPBZKOONK-UHFFFAOYSA-N 0.000 description 1
- RGKBVFNEYWPEKB-UHFFFAOYSA-N (3-chloro-5-iodo-4-methoxyphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(I)C(OC)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 RGKBVFNEYWPEKB-UHFFFAOYSA-N 0.000 description 1
- WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- QHUSRJSYQNJEFQ-UHFFFAOYSA-N 3-chloro-5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxybenzonitrile Chemical compound C1=C(C#N)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 QHUSRJSYQNJEFQ-UHFFFAOYSA-N 0.000 description 1
- BFCXETQQBNMRHL-UHFFFAOYSA-N 3-chloro-5-iodo-4-methoxybenzoic acid Chemical compound COC1=C(Cl)C=C(C(O)=O)C=C1I BFCXETQQBNMRHL-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MTHRZZFLSQRKKO-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(O)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 MTHRZZFLSQRKKO-UHFFFAOYSA-N 0.000 description 1
- SBCRKZJEEDTVFK-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-methylsulfanylbenzonitrile Chemical compound N#CC1=C(O)C(SC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 SBCRKZJEEDTVFK-UHFFFAOYSA-N 0.000 description 1
- ZIQZOFGOOVJLLL-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-methylsulfinylbenzonitrile Chemical compound N#CC1=C(O)C(S(=O)C)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 ZIQZOFGOOVJLLL-UHFFFAOYSA-N 0.000 description 1
- FLUWNGKLTHJDDR-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-methoxy-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(OC)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 FLUWNGKLTHJDDR-UHFFFAOYSA-N 0.000 description 1
- ZMYHQWPKHSCITJ-UHFFFAOYSA-N 5-(2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(O)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2SC1 ZMYHQWPKHSCITJ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- RZXBSMVVNURIFG-UHFFFAOYSA-N [3-chloro-4-hydroxy-5-(trifluoromethyl)phenyl]-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(C(F)(F)F)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 RZXBSMVVNURIFG-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- ZSBIMTDWIGWJPW-UHFFFAOYSA-N methyl 3-chloro-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Cl)=C1 ZSBIMTDWIGWJPW-UHFFFAOYSA-N 0.000 description 1
- CCRJCQCBZLEJRF-UHFFFAOYSA-N methyl 3-chloro-5-cyano-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C(C#N)=C1 CCRJCQCBZLEJRF-UHFFFAOYSA-N 0.000 description 1
- WIXKYCQCCJXQPN-UHFFFAOYSA-N methyl 4-hydroxy-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(O)C(C(F)(F)F)=C1 WIXKYCQCCJXQPN-UHFFFAOYSA-N 0.000 description 1
- 229960005206 pyrazinamide Drugs 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000003424 uricosuric effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D277/62—Benzothiazoles
-
- 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
- A61K31/41—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
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- 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
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
- A61P9/12—Antihypertensives
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- 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
-
- 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
- C07D417/10—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 linked by a carbon chain containing aromatic rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| JP5851802B2 (ja) | 2011-03-30 | 2016-02-03 | 富士重工業株式会社 | 炭素繊維強化樹脂複合材用ドリル |
| WO2015191034A1 (en) * | 2014-06-09 | 2015-12-17 | Baylor College Of Medicine | Small molecule xanthine oxidase inhibitors and methods of use |
| WO2017038799A1 (ja) * | 2015-09-04 | 2017-03-09 | サントリーホールディングス株式会社 | ウレアーゼ活性阻害剤 |
| CA2998034C (en) * | 2015-09-10 | 2021-05-04 | Dongfang Shi | A group of compounds used for the treatment or prevention of hyperuricemia or gout |
| CN105675557B (zh) * | 2016-01-07 | 2019-01-25 | 济南大学 | 基于苯炔荧光试剂检测硫脲含量的新方法 |
| KR102610573B1 (ko) | 2016-07-18 | 2023-12-05 | 아쓰로시 테라퓨틱스, 인크. | 통풍 또는 고뇨산혈증과 관련된 증상의 치료 또는 예방을 위한 화합물, 조성물 및 방법 |
| SG11201909747WA (en) * | 2017-04-28 | 2019-11-28 | Fuji Yakuhin Co Ltd | Crystal form and salt of 3-(3,5-dichloro-4-hydroxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole |
| CN109928890B (zh) * | 2017-12-15 | 2021-11-09 | 重庆常捷医药有限公司 | 一种托伐普坦中间体2-甲基-4-n-(2-甲基苯甲酰)苯甲酸的制备方法 |
| BR112021010708A2 (pt) | 2018-12-06 | 2021-08-24 | Arthrosi Therapeutics, Inc. | Formas cristalinas de um composto para tratar ou prevenir gota ou hiperuricemia |
| AU2019392750B2 (en) | 2018-12-06 | 2025-07-10 | Arthrosi Therapeutics, Inc. | Methods for treating or preventing gout or hyperuricemia |
| CA3159300A1 (en) * | 2019-12-09 | 2021-06-17 | Tadashi Inoue | Solid pharmaceutical preparation |
| CN111662247A (zh) * | 2020-07-17 | 2020-09-15 | 苏州明锐医药科技有限公司 | 一种多替诺德的合成方法 |
| CN111675675A (zh) * | 2020-07-17 | 2020-09-18 | 苏州明锐医药科技有限公司 | 多替诺德的制备方法 |
| CN112430221B (zh) * | 2020-11-20 | 2023-06-23 | 成都诺和晟泰生物科技有限公司 | 用于预防、治疗或减轻高尿酸血症或痛风的化合物及其应用 |
| WO2022169974A1 (en) | 2021-02-05 | 2022-08-11 | Nexys Therapeutics, Inc. | Inhibitors of urat1 and pharmaceutical uses thereof |
| CN114903879B (zh) * | 2022-06-23 | 2023-10-31 | 东北大学 | 3-烃基苯酚衍生物在制备预防或治疗高脂血症及相关代谢性疾病产品中的用途 |
| CN115160314B (zh) * | 2022-07-28 | 2023-12-05 | 南方医科大学 | 杂环芳酰胺类化合物及其制备方法和应用 |
| WO2025085662A1 (en) | 2023-10-17 | 2025-04-24 | Vanderbilt University | Compounds for tocolytic use |
| CN118580197A (zh) * | 2023-11-16 | 2024-09-03 | 广东东阳光药业股份有限公司 | 一种多替诺雷制备方法及其应用 |
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| US3720683A (en) * | 1970-09-02 | 1973-03-13 | Squibb & Sons Inc | 2-phenyl-3-acylbenzothiazolines and their oxides |
| WO2005121112A1 (ja) | 2004-06-10 | 2005-12-22 | Torii Pharmaceutical Co., Ltd. | ６－ヒドロキシベンズブロマロン又はその塩からなる医薬組成物 |
| JP3988832B2 (ja) | 2004-11-29 | 2007-10-10 | 日本たばこ産業株式会社 | 窒素含有縮合環化合物及びその用途 |
| AR051780A1 (es) * | 2004-11-29 | 2007-02-07 | Japan Tobacco Inc | Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos |
| EP1985297A1 (en) * | 2006-01-27 | 2008-10-29 | Japan Tobacco, Inc. | Carboxylic acid compound and use thereof |
| US20080305169A1 (en) * | 2006-05-26 | 2008-12-11 | Japan Tobacco Inc. | Pharmaceutical Compositions Comprising Nitrogen-Containing Fused Ring Coumpounds |
| US20080064871A1 (en) * | 2006-05-26 | 2008-03-13 | Japan Tobacco Inc. | Production Method of Nitrogen-Containing Fused Ring Compounds |
| WO2008062740A1 (fr) * | 2006-11-20 | 2008-05-29 | Japan Tobacco Inc. | Composé azoté à anneaux fusionnés et son utilisation |
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