BRPI0509353B1 - processo para a produção de um composto de 5-hidróxi-4-tiometilpirazol - Google Patents
processo para a produção de um composto de 5-hidróxi-4-tiometilpirazol Download PDFInfo
- Publication number
- BRPI0509353B1 BRPI0509353B1 BRPI0509353A BRPI0509353A BRPI0509353B1 BR PI0509353 B1 BRPI0509353 B1 BR PI0509353B1 BR PI0509353 A BRPI0509353 A BR PI0509353A BR PI0509353 A BRPI0509353 A BR PI0509353A BR PI0509353 B1 BRPI0509353 B1 BR PI0509353B1
- Authority
- BR
- Brazil
- Prior art keywords
- group
- hydroxy
- compound
- represented
- thiomethylpyrazole
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 65
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 77
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052751 metal Chemical group 0.000 claims description 13
- 239000002184 metal Chemical group 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000008030 elimination Effects 0.000 claims description 8
- 238000003379 elimination reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 230000002000 scavenging effect Effects 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- -1 pyrazole compound Chemical class 0.000 abstract description 98
- 239000003054 catalyst Substances 0.000 abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 abstract description 5
- 150000003624 transition metals Chemical class 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 3
- ASCNUIWVIZJLFA-UHFFFAOYSA-N 4-(hydroxysulfanylmethyl)-1H-pyrazole Chemical compound OSCC=1C=NNC1 ASCNUIWVIZJLFA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000013078 crystal Substances 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- 238000003756 stirring Methods 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 239000013058 crude material Substances 0.000 description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 8
- WQRHIGNAKDJJKN-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound CN1NC(C(F)(F)F)=CC1=O WQRHIGNAKDJJKN-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 description 7
- 159000000009 barium salts Chemical class 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910003002 lithium salt Inorganic materials 0.000 description 7
- 159000000002 lithium salts Chemical class 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 6
- 159000000003 magnesium salts Chemical class 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000011345 viscous material Substances 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 5
- PSQCMVQGPMFFCX-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound N1C(C(F)(F)F)=CC(=O)N1C1=CC=CC=C1 PSQCMVQGPMFFCX-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- VCQMKGOPYFTGTJ-UHFFFAOYSA-N 3-oxo-2-phenyl-1h-pyrazole-5-carbonitrile Chemical compound O=C1C=C(C#N)NN1C1=CC=CC=C1 VCQMKGOPYFTGTJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RVOZMSKEULVWIX-UHFFFAOYSA-N C1=C(O)N(C)N=C1C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 Chemical compound C1=C(O)N(C)N=C1C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 RVOZMSKEULVWIX-UHFFFAOYSA-N 0.000 description 3
- FGHRRXTXDNWRGJ-UHFFFAOYSA-N C1=C(O)N(C)N=C1C1=CC=C(Cl)C=C1Cl Chemical compound C1=C(O)N(C)N=C1C1=CC=C(Cl)C=C1Cl FGHRRXTXDNWRGJ-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- YMCWJQIZJIKFHO-UHFFFAOYSA-N 3-chloro-5,5-dimethyl-4h-1,2-oxazole Chemical compound CC1(C)CC(Cl)=NO1 YMCWJQIZJIKFHO-UHFFFAOYSA-N 0.000 description 2
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 2
- VYPKNQCJDTUNQM-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2-dihydropyrazol-3-one;hydrochloride Chemical compound Cl.OC1=CC(C(F)(F)F)=NN1 VYPKNQCJDTUNQM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZJMVRJKNSCYPGP-UHFFFAOYSA-N C1=CC(C)=CC=C1S(=O)(=O)CC1=C(O)N(C)N=C1C(F)(F)F Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC1=C(O)N(C)N=C1C(F)(F)F ZJMVRJKNSCYPGP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CFLCNYNIHRZAHT-UHFFFAOYSA-N N1=C(C(=O)OCC)C=C(O)N1C1=CC=CC=C1C Chemical compound N1=C(C(=O)OCC)C=C(O)N1C1=CC=CC=C1C CFLCNYNIHRZAHT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
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- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004102963A JP4621939B2 (ja) | 2004-03-31 | 2004-03-31 | ５−ヒドロキシ−４−チオメチルピラゾール化合物の製造方法 |
| PCT/JP2005/006806 WO2005095352A1 (ja) | 2004-03-31 | 2005-03-31 | ５－ヒドロキシ－４－チオメチルピラゾール化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BRPI0509353A BRPI0509353A (pt) | 2007-09-11 |
| BRPI0509353A8 BRPI0509353A8 (pt) | 2017-09-19 |
| BRPI0509353B1 true BRPI0509353B1 (pt) | 2019-01-02 |
Family
ID=35063690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0509353A BRPI0509353B1 (pt) | 2004-03-31 | 2005-03-31 | processo para a produção de um composto de 5-hidróxi-4-tiometilpirazol |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7488831B2 (https=) |
| EP (1) | EP1767528B1 (https=) |
| JP (1) | JP4621939B2 (https=) |
| KR (1) | KR101205731B1 (https=) |
| CN (1) | CN1938278B (https=) |
| AU (1) | AU2005228017B2 (https=) |
| BR (1) | BRPI0509353B1 (https=) |
| CA (1) | CA2560936C (https=) |
| CR (1) | CR8640A (https=) |
| ES (1) | ES2508765T3 (https=) |
| IL (1) | IL178233A (https=) |
| IN (1) | IN2006DE05581A (https=) |
| MX (1) | MX280092B (https=) |
| NZ (1) | NZ550143A (https=) |
| PL (1) | PL1767528T3 (https=) |
| RU (1) | RU2386619C2 (https=) |
| TW (1) | TWI357899B (https=) |
| UA (1) | UA83910C2 (https=) |
| WO (1) | WO2005095352A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2333977T3 (es) | 2004-10-05 | 2010-03-03 | Syngenta Limited | Derivados de isoxazolina y su uso como herbicidas. |
| MX274842B (es) * | 2004-12-20 | 2010-03-30 | Ihara Chemical Ind Co | Procedimiento para la produccion de sales de (4,5-dihidroisoxazol- 3-il)tiocarboxamidina. |
| JP2007031342A (ja) * | 2005-07-27 | 2007-02-08 | Ihara Chem Ind Co Ltd | ５−ヒドロキシ−１−アルキルピラゾール誘導体の製造方法 |
| CA2642308C (en) * | 2006-02-14 | 2013-12-17 | Ihara Chemical Industry Co., Ltd. | Process for production of 5-alkoxy-4-hydroxymethylpyrazole compound |
| TWI443090B (zh) * | 2007-05-25 | 2014-07-01 | Abbvie Deutschland | 作為代謝性麩胺酸受體２（ｍｇｌｕ２ 受體）之正向調節劑之雜環化合物 |
| GB0916267D0 (en) | 2009-09-16 | 2009-10-28 | Syngenta Ltd | Herbicidal compounds |
| US20120238760A1 (en) | 2009-11-26 | 2012-09-20 | Basf Se | Method for Producing 5,5-Disubstituted 2-Isoxazolines |
| ES2466322T3 (es) * | 2009-11-26 | 2014-06-10 | Basf Se | Procedimiento para la preparación de sales de 4,5-dihidroisoxazol-3-tiocarboxamidina 5,5-disustituida |
| DK2571854T3 (en) * | 2010-05-20 | 2015-02-09 | Bayer Ip Gmbh | PROCESS FOR THE PREPARATION OF 1-alkyl-3-difluoromethyl-5-hydroxypyrazoles |
| CA2843415C (en) | 2011-07-29 | 2019-12-31 | University Of Saskatchewan | Polymer-based resonator antennas |
| CN103387541B (zh) * | 2012-05-10 | 2016-02-10 | 中国中化股份有限公司 | 一种取代吡唑醚类化合物的制备方法 |
| JP6400247B1 (ja) | 2015-11-16 | 2018-10-03 | ロンザ・リミテッド | １−メチル−３−（トリフルオロメチル）−１ｈ−ピラゾール−５−オールの調製方法 |
| TW201835036A (zh) | 2017-02-27 | 2018-10-01 | 瑞士商隆薩有限公司 | 製備1-甲基-3-(三氟甲基)-1h-吡唑-5-醇的方法 |
| JP6664036B2 (ja) | 2017-12-27 | 2020-03-13 | クミアイ化学工業株式会社 | チオカルボキサミジン塩化合物の製造方法 |
| CN112135814B (zh) * | 2018-05-31 | 2021-09-28 | 组合化学工业株式会社 | 含氟吡唑衍生物的制造方法及其中间体 |
| EP4003964B1 (en) | 2019-07-30 | 2024-09-18 | Adama Agan Ltd. | Process and intermediates for the preparation of pyroxasulfone |
| KR102523028B1 (ko) | 2019-10-31 | 2023-04-17 | 구미아이 가가쿠 고교 가부시키가이샤 | 제초제 및 그 중간체의 제조방법 |
| IL296145A (en) | 2020-03-05 | 2022-11-01 | Adama Agan Ltd | A process for the preparation of pyroxasulfone and intermediates obtained in this process |
| CN111574511A (zh) * | 2020-06-28 | 2020-08-25 | 安徽久易农业股份有限公司 | 一种砜吡草唑的合成方法及其应用 |
| EP4177252A3 (en) | 2020-07-10 | 2023-08-09 | Adama Agan Ltd. | Process and intermediates for the preparation of pyroxasulfone, fenoxasulfone and various sulfone analogs of 5,5-dimethyl-4h-1,2-oxazole |
| CN112110912B (zh) * | 2020-07-31 | 2022-07-05 | 绍兴贝斯美化工股份有限公司 | 一种合成硫醚类中间体的方法 |
| WO2023074828A1 (ja) | 2021-10-29 | 2023-05-04 | クミアイ化学工業株式会社 | ジスルフィド化合物、ポリスルフィド化合物及びその用途 |
| AR127776A1 (es) | 2021-11-28 | 2024-02-28 | Adama Agan Ltd | Composiciones de concentrado en suspensión de alta carga |
| CN114716428B (zh) * | 2022-05-06 | 2024-02-06 | 山东潍坊润丰化工股份有限公司 | 制备砜吡草唑中间体的方法 |
| CN115850178B (zh) * | 2022-12-28 | 2025-04-04 | 宁夏格瑞精细化工有限公司 | 一种1-甲基-3-(三氟甲基)-1h-吡唑-5-醇的制备方法 |
| CN117417333B (zh) * | 2023-10-07 | 2026-02-17 | 安徽久易农业股份有限公司 | 一种砜吡草唑的合成工艺 |
| CN120590326B (zh) * | 2025-06-05 | 2025-12-23 | 济南万兴达化工有限公司 | 一种1-甲基-3-（三氟甲基）-1h-吡唑-5-醇的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918085A (en) * | 1989-03-02 | 1990-04-17 | Rhone-Poulenc Ag Company | Pesticidal 3-cyano-5-alkoxy-1-arylpyrazoles, compositions and use |
| AR035912A1 (es) * | 2000-03-02 | 2004-07-28 | Aventis Cropscience Sa | Compuestos de 4-tiometilpirazol, composicion plaguicida, metodo para el control de plagas en un lugar, semillas tratadas o recubiertas,uso de estos compuestos o composiciones para el control de plagas, uso de estos compuestos para preparar un medicamento veterinario, y,proceso para la preparacion de |
| JP4465133B2 (ja) * | 2001-02-08 | 2010-05-19 | クミアイ化学工業株式会社 | イソオキサゾリン誘導体及びこれを有効成分とする除草剤 |
| WO2003000686A1 (en) * | 2001-06-21 | 2003-01-03 | Kumiai Chemical Industry Co., Ltd. | Isoxazoline derivatives and herbicides |
| AU2003252447B2 (en) * | 2002-08-01 | 2008-06-05 | Kumiai Chemical Industry Co., Ltd. | Pyrazole derivatives and process for the production thereof |
| UA78071C2 (en) * | 2002-08-07 | 2007-02-15 | Kumiai Chemical Industry Co | Herbicidal composition |
-
2004
- 2004-03-31 JP JP2004102963A patent/JP4621939B2/ja not_active Expired - Lifetime
-
2005
- 2005-03-31 CA CA2560936A patent/CA2560936C/en not_active Expired - Lifetime
- 2005-03-31 UA UAA200611331A patent/UA83910C2/ru unknown
- 2005-03-31 AU AU2005228017A patent/AU2005228017B2/en not_active Expired
- 2005-03-31 MX MXPA06011130 patent/MX280092B/es active IP Right Grant
- 2005-03-31 TW TW094110223A patent/TWI357899B/zh not_active IP Right Cessation
- 2005-03-31 ES ES05728918.3T patent/ES2508765T3/es not_active Expired - Lifetime
- 2005-03-31 KR KR1020067019480A patent/KR101205731B1/ko not_active Expired - Lifetime
- 2005-03-31 US US10/594,710 patent/US7488831B2/en not_active Expired - Lifetime
- 2005-03-31 EP EP05728918.3A patent/EP1767528B1/en not_active Expired - Lifetime
- 2005-03-31 WO PCT/JP2005/006806 patent/WO2005095352A1/ja not_active Ceased
- 2005-03-31 RU RU2006138241/04A patent/RU2386619C2/ru active
- 2005-03-31 CN CN2005800106359A patent/CN1938278B/zh not_active Expired - Lifetime
- 2005-03-31 PL PL05728918T patent/PL1767528T3/pl unknown
- 2005-03-31 NZ NZ550143A patent/NZ550143A/en not_active IP Right Cessation
- 2005-03-31 BR BRPI0509353A patent/BRPI0509353B1/pt active IP Right Grant
-
2006
- 2006-09-20 CR CR8640A patent/CR8640A/es unknown
- 2006-09-21 IL IL178233A patent/IL178233A/en active IP Right Grant
- 2006-09-25 IN IN5581DE2006 patent/IN2006DE05581A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1767528A1 (en) | 2007-03-28 |
| EP1767528B1 (en) | 2014-09-17 |
| ES2508765T3 (es) | 2014-10-16 |
| JP4621939B2 (ja) | 2011-02-02 |
| CA2560936C (en) | 2013-01-08 |
| MXPA06011130A (es) | 2007-01-25 |
| TW200536832A (en) | 2005-11-16 |
| US20070185334A1 (en) | 2007-08-09 |
| CR8640A (es) | 2007-08-28 |
| BRPI0509353A (pt) | 2007-09-11 |
| IL178233A (en) | 2014-02-27 |
| AU2005228017A1 (en) | 2005-10-13 |
| RU2386619C2 (ru) | 2010-04-20 |
| CN1938278B (zh) | 2012-12-12 |
| NZ550143A (en) | 2010-04-30 |
| UA83910C2 (ru) | 2008-08-26 |
| PL1767528T3 (pl) | 2015-03-31 |
| CN1938278A (zh) | 2007-03-28 |
| KR20070003964A (ko) | 2007-01-05 |
| IN2006DE05581A (https=) | 2007-08-31 |
| AU2005228017B2 (en) | 2010-09-30 |
| RU2006138241A (ru) | 2008-05-10 |
| CA2560936A1 (en) | 2005-10-13 |
| IL178233A0 (en) | 2006-12-31 |
| KR101205731B1 (ko) | 2012-11-28 |
| BRPI0509353A8 (pt) | 2017-09-19 |
| EP1767528A4 (en) | 2010-04-21 |
| WO2005095352A1 (ja) | 2005-10-13 |
| US7488831B2 (en) | 2009-02-10 |
| TWI357899B (en) | 2012-02-11 |
| MX280092B (es) | 2010-10-18 |
| JP2005289824A (ja) | 2005-10-20 |
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| Date | Code | Title | Description |
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| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] | ||
| B25A | Requested transfer of rights approved |
Owner name: KUMIAI CHEMICAL INDUSTRY CO., LTD. (JP) |
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| B07G | Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
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