JPS63190869A - 新規アルカンスルホンアニリド誘導体、その製造法およびそれを含有する医薬組成物 - Google Patents
新規アルカンスルホンアニリド誘導体、その製造法およびそれを含有する医薬組成物Info
- Publication number
- JPS63190869A JPS63190869A JP62335647A JP33564787A JPS63190869A JP S63190869 A JPS63190869 A JP S63190869A JP 62335647 A JP62335647 A JP 62335647A JP 33564787 A JP33564787 A JP 33564787A JP S63190869 A JPS63190869 A JP S63190869A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen
- salts
- difluorophenoxy
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 90
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 191
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- -1 carboxy, mercapto Chemical class 0.000 claims abstract description 84
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
- 125000002252 acyl group Chemical group 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 9
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 7
- DIIYLGZNZGPXRR-UHFFFAOYSA-N n-[4-acetyl-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 DIIYLGZNZGPXRR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- NPUFTSHCCYEUKN-UHFFFAOYSA-N n-[4-cyano-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C#N)C=C1OC1=CC=C(F)C=C1F NPUFTSHCCYEUKN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000006103 sulfonylation Effects 0.000 abstract 1
- 238000005694 sulfonylation reaction Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 166
- 239000000203 mixture Substances 0.000 description 133
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 57
- 239000002585 base Substances 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- 239000003921 oil Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 238000003756 stirring Methods 0.000 description 31
- 238000010438 heat treatment Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 239000000843 powder Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000002411 adverse Effects 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 14
- 235000008504 concentrate Nutrition 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- JMDTYTPKUYOLPX-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(OC=2C(=CC(F)=CC=2)F)=C1 JMDTYTPKUYOLPX-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- QOQXTZQLLZYNEJ-UHFFFAOYSA-N 1-[4-amino-3-(2,4-difluorophenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(N)C(OC=2C(=CC(F)=CC=2)F)=C1 QOQXTZQLLZYNEJ-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 3
- JXVYZLOOAZFTSQ-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1OC1=CC=C(F)C=C1F JXVYZLOOAZFTSQ-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- QXRFTNZBPHQQAR-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-formylphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C=O)C=C1OC1=CC=C(F)C=C1F QXRFTNZBPHQQAR-UHFFFAOYSA-N 0.000 description 3
- MIHRVCSSMAGKNH-UHFFFAOYSA-M n-ethylcarbamodithioate Chemical compound CCNC([S-])=S MIHRVCSSMAGKNH-UHFFFAOYSA-M 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VGVXDPRCTIRHOO-UHFFFAOYSA-N 1-(4-amino-3-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C(Cl)=C1 VGVXDPRCTIRHOO-UHFFFAOYSA-N 0.000 description 2
- NWYQDOFWQGYMTB-UHFFFAOYSA-N 1-(4-amino-3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C(OC=2C=CC=CC=2)=C1 NWYQDOFWQGYMTB-UHFFFAOYSA-N 0.000 description 2
- VICWBLNIZFWGJL-UHFFFAOYSA-N 1-[3-(2,4-difluorophenoxy)-4-nitrophenyl]ethanone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C(OC=2C(=CC(F)=CC=2)F)=C1 VICWBLNIZFWGJL-UHFFFAOYSA-N 0.000 description 2
- PXVLPDMOGXAKMG-UHFFFAOYSA-N 1-[3-(3-chlorophenoxy)-4-nitrophenyl]ethanone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C(OC=2C=C(Cl)C=CC=2)=C1 PXVLPDMOGXAKMG-UHFFFAOYSA-N 0.000 description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- FSWXOANXOQPCFF-UHFFFAOYSA-N 4'-aminopropiophenone Chemical compound CCC(=O)C1=CC=C(N)C=C1 FSWXOANXOQPCFF-UHFFFAOYSA-N 0.000 description 2
- CJGGBLRETOBFHC-UHFFFAOYSA-N 4-amino-3-(2,4-difluorophenoxy)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(N)C(OC=2C(=CC(F)=CC=2)F)=C1 CJGGBLRETOBFHC-UHFFFAOYSA-N 0.000 description 2
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- 159000000002 lithium salts Chemical class 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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- 125000006362 methylene amino carbonyl group Chemical group [H]N(C([*:2])=O)C([H])([H])[*:1] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
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- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- UFKRTEWFEYWIHD-UHFFFAOYSA-N n-(4-cyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1 UFKRTEWFEYWIHD-UHFFFAOYSA-N 0.000 description 1
- YABUKBRATHJUGT-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(1-hydroxyethyl)phenyl]methanesulfonamide Chemical compound CC(O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 YABUKBRATHJUGT-UHFFFAOYSA-N 0.000 description 1
- JRLXMBKEDZDXRS-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(2-methylsulfonylacetyl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 JRLXMBKEDZDXRS-UHFFFAOYSA-N 0.000 description 1
- PTKZAIBUWGBWEF-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(2-pyridin-1-ium-1-ylacetyl)phenyl]methanesulfonamide;chloride Chemical compound [Cl-].CS(=O)(=O)NC1=CC=C(C(=O)C[N+]=2C=CC=CC=2)C=C1OC1=CC=C(F)C=C1F PTKZAIBUWGBWEF-UHFFFAOYSA-N 0.000 description 1
- VDXAFRXZGNEPCA-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(2h-tetrazol-5-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C2=NNN=N2)C=C1OC1=CC=C(F)C=C1F VDXAFRXZGNEPCA-UHFFFAOYSA-N 0.000 description 1
- XPFRPCORKIRVFO-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(3-ethylsulfanyl-1,2,4-oxadiazol-5-yl)phenyl]methanesulfonamide Chemical compound CCSC1=NOC(C=2C=C(OC=3C(=CC(F)=CC=3)F)C(NS(C)(=O)=O)=CC=2)=N1 XPFRPCORKIRVFO-UHFFFAOYSA-N 0.000 description 1
- PQPPVAKNNHLUPW-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(4-methylpiperazine-1-carbonyl)phenyl]methanesulfonamide Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 PQPPVAKNNHLUPW-UHFFFAOYSA-N 0.000 description 1
- XIXPOUNLBLNIQV-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(hydroxyiminomethyl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C=NO)C=C1OC1=CC=C(F)C=C1F XIXPOUNLBLNIQV-UHFFFAOYSA-N 0.000 description 1
- SJZGMEYKGNKNNS-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(methoxyiminomethyl)phenyl]methanesulfonamide Chemical compound CON=CC1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 SJZGMEYKGNKNNS-UHFFFAOYSA-N 0.000 description 1
- UMOGHASMUZWBER-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-(n-ethoxy-c-methylcarbonimidoyl)phenyl]methanesulfonamide Chemical compound CCON=C(C)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 UMOGHASMUZWBER-UHFFFAOYSA-N 0.000 description 1
- SGMLMAGBEBKEMM-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-methylsulfanylphenyl]methanesulfonamide Chemical compound CSC1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 SGMLMAGBEBKEMM-UHFFFAOYSA-N 0.000 description 1
- FVHIRUNXUUXKFO-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-methylsulfinylphenyl]methanesulfonamide Chemical compound CS(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 FVHIRUNXUUXKFO-UHFFFAOYSA-N 0.000 description 1
- ALWGRWXCJPZGMT-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-methylsulfonylphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(S(C)(=O)=O)C=C1OC1=CC=C(F)C=C1F ALWGRWXCJPZGMT-UHFFFAOYSA-N 0.000 description 1
- FVJPDAVUWRIUNE-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-4-propanoylphenyl]methanesulfonamide Chemical compound CCC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 FVJPDAVUWRIUNE-UHFFFAOYSA-N 0.000 description 1
- IWBGXAFLMPWGQD-UHFFFAOYSA-N n-[4-(2-amino-1,3-thiazol-4-yl)-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C=2N=C(N)SC=2)C=C1OC1=CC=C(F)C=C1F IWBGXAFLMPWGQD-UHFFFAOYSA-N 0.000 description 1
- FIANIRUHTJXHON-UHFFFAOYSA-N n-[4-(4-aminophenyl)sulfanyl-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=C(OC=2C(=CC(F)=CC=2)F)C(NS(=O)(=O)C)=CC=C1SC1=CC=C(N)C=C1 FIANIRUHTJXHON-UHFFFAOYSA-N 0.000 description 1
- GSFYKNIHIHHGCM-UHFFFAOYSA-N n-[4-[3-(2,4-difluorophenoxy)-4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(OC=3C(=CC(F)=CC=3)F)C(NS(C)(=O)=O)=CC=2)=C1 GSFYKNIHIHHGCM-UHFFFAOYSA-N 0.000 description 1
- WKCWRSLGNZGMID-UHFFFAOYSA-N n-[4-acetyl-2-(2,3-dichlorophenoxy)phenyl]methanesulfonamide;sodium Chemical compound [Na].CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=C(Cl)C=CC=2)Cl)=C1 WKCWRSLGNZGMID-UHFFFAOYSA-N 0.000 description 1
- YACLNRLSYFYKBR-UHFFFAOYSA-N n-[4-acetyl-2-(2,4-dichlorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(Cl)=CC=2)Cl)=C1 YACLNRLSYFYKBR-UHFFFAOYSA-N 0.000 description 1
- ICOSTQUKAUIKNG-UHFFFAOYSA-N n-[4-acetyl-2-(2,4-difluorophenoxy)-5-methylphenyl]methanesulfonamide Chemical compound C1=C(C)C(C(=O)C)=CC(OC=2C(=CC(F)=CC=2)F)=C1NS(C)(=O)=O ICOSTQUKAUIKNG-UHFFFAOYSA-N 0.000 description 1
- KNSDPHAPJVPIJA-UHFFFAOYSA-N n-[4-acetyl-2-(2,5-dichlorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=C(Cl)C=2)Cl)=C1 KNSDPHAPJVPIJA-UHFFFAOYSA-N 0.000 description 1
- URNKLAYOPPHOAF-UHFFFAOYSA-N n-[4-acetyl-2-(2,6-dichlorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=CC=2Cl)Cl)=C1 URNKLAYOPPHOAF-UHFFFAOYSA-N 0.000 description 1
- NPSGBFYQEJJWCY-UHFFFAOYSA-N n-[4-acetyl-2-(2-bromophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=CC=2)Br)=C1 NPSGBFYQEJJWCY-UHFFFAOYSA-N 0.000 description 1
- KURAHRFVFSSNSH-UHFFFAOYSA-N n-[4-acetyl-2-(2-chloro-4-fluorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)Cl)=C1 KURAHRFVFSSNSH-UHFFFAOYSA-N 0.000 description 1
- KXIUFKOSMDRMQZ-UHFFFAOYSA-N n-[4-acetyl-2-(2-chlorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=CC=2)Cl)=C1 KXIUFKOSMDRMQZ-UHFFFAOYSA-N 0.000 description 1
- URQKRSOUXCLDGZ-UHFFFAOYSA-N n-[4-acetyl-2-(2-fluorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=CC=2)F)=C1 URQKRSOUXCLDGZ-UHFFFAOYSA-N 0.000 description 1
- LZGRDPFGYSRKCE-UHFFFAOYSA-N n-[4-acetyl-2-(2-methoxyphenoxy)phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1OC1=CC(C(C)=O)=CC=C1NS(C)(=O)=O LZGRDPFGYSRKCE-UHFFFAOYSA-N 0.000 description 1
- NNXRNGYWQJUILQ-UHFFFAOYSA-N n-[4-acetyl-2-(2-methylsulfonylphenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC=CC=2)S(C)(=O)=O)=C1 NNXRNGYWQJUILQ-UHFFFAOYSA-N 0.000 description 1
- WJXHFYLQDVXXKV-UHFFFAOYSA-N n-[4-acetyl-2-(4-fluorophenoxy)phenyl]methanesulfonamide Chemical compound CC(=O)C1=CC=C(NS(C)(=O)=O)C(OC=2C=CC(F)=CC=2)=C1 WJXHFYLQDVXXKV-UHFFFAOYSA-N 0.000 description 1
- GCJZTCGDFATLAH-UHFFFAOYSA-N n-[4-acetyl-2-chloro-6-(2,4-difluorophenoxy)phenyl]methanesulfonamide;sodium Chemical compound [Na].CC(=O)C1=CC(Cl)=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 GCJZTCGDFATLAH-UHFFFAOYSA-N 0.000 description 1
- IAXOHHMHNZMWOR-UHFFFAOYSA-N n-[4-amino-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(N)C=C1OC1=CC=C(F)C=C1F IAXOHHMHNZMWOR-UHFFFAOYSA-N 0.000 description 1
- LREDYAJOSZTDMA-UHFFFAOYSA-N n-[4-benzoyl-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide;sodium Chemical compound [Na].CS(=O)(=O)NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1OC1=CC=C(F)C=C1F LREDYAJOSZTDMA-UHFFFAOYSA-N 0.000 description 1
- WRZSZKQVYBJXPD-UHFFFAOYSA-N n-[4-cyano-2-(2,4-dichlorophenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C#N)C=C1OC1=CC=C(Cl)C=C1Cl WRZSZKQVYBJXPD-UHFFFAOYSA-N 0.000 description 1
- NQTYMYLQHFQEAN-UHFFFAOYSA-N n-[5-chloro-4-cyano-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(Cl)=C(C#N)C=C1OC1=CC=C(F)C=C1F NQTYMYLQHFQEAN-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- TVWAXDOYLOWHJF-UHFFFAOYSA-N potassium;lithium Chemical compound [Li].[K+] TVWAXDOYLOWHJF-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- TXKRWVMEUQBFSO-UHFFFAOYSA-N sulfuric acid;trihydrate Chemical compound O.O.O.OS(O)(=O)=O TXKRWVMEUQBFSO-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- SRZAHZOSCNQZHM-UHFFFAOYSA-N tert-butyl 2-[1-[3-(2,4-difluorophenoxy)-4-(methanesulfonamido)phenyl]ethylideneamino]oxyacetate Chemical compound CC(C)(C)OC(=O)CON=C(C)C1=CC=C(NS(C)(=O)=O)C(OC=2C(=CC(F)=CC=2)F)=C1 SRZAHZOSCNQZHM-UHFFFAOYSA-N 0.000 description 1
- MXJGKTHZWIGRJG-UHFFFAOYSA-N tert-butyl 2-aminooxyacetate Chemical compound CC(C)(C)OC(=O)CON MXJGKTHZWIGRJG-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000009736 wetting Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8631083 | 1986-12-31 | ||
| GB868631083A GB8631083D0 (en) | 1986-12-31 | 1986-12-31 | 2'-phenoxyalkanesulfonanilide derivatives |
| GB8712647 | 1987-05-29 | ||
| GB8724903 | 1987-10-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63190869A true JPS63190869A (ja) | 1988-08-08 |
| JPH0519543B2 JPH0519543B2 (de) | 1993-03-17 |
Family
ID=10609710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62335647A Granted JPS63190869A (ja) | 1986-12-31 | 1987-12-28 | 新規アルカンスルホンアニリド誘導体、その製造法およびそれを含有する医薬組成物 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS63190869A (de) |
| GB (1) | GB8631083D0 (de) |
| RU (1) | RU1799378C (de) |
| ZA (1) | ZA879706B (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02138168A (ja) * | 1988-11-18 | 1990-05-28 | Hisamitsu Pharmaceut Co Inc | スルホンアニリド誘導体 |
| WO1993025520A1 (en) * | 1992-06-12 | 1993-12-23 | Taisho Pharmaceutical Co., Ltd. | 5-amino-2-phenoxysulfonanilide compound |
| JP2010508238A (ja) * | 2006-04-10 | 2010-03-18 | シェーリング−プラウ・リミテッド | Ｎ−フェニル−１，１，１−トリフルオロメタンスルホンアミドヒドラゾン誘導体化合物および寄生生物の制御におけるそれらの使用 |
-
1986
- 1986-12-31 GB GB868631083A patent/GB8631083D0/en active Pending
-
1987
- 1987-12-28 ZA ZA879706A patent/ZA879706B/xx unknown
- 1987-12-28 JP JP62335647A patent/JPS63190869A/ja active Granted
- 1987-12-30 RU SU874203921A patent/RU1799378C/ru active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02138168A (ja) * | 1988-11-18 | 1990-05-28 | Hisamitsu Pharmaceut Co Inc | スルホンアニリド誘導体 |
| WO1993025520A1 (en) * | 1992-06-12 | 1993-12-23 | Taisho Pharmaceutical Co., Ltd. | 5-amino-2-phenoxysulfonanilide compound |
| US5449826A (en) * | 1992-06-12 | 1995-09-12 | Taisho Pharmaceutical Co., Ltd. | 5-amino-2-phenoxysulfonanilide compound |
| JP2010508238A (ja) * | 2006-04-10 | 2010-03-18 | シェーリング−プラウ・リミテッド | Ｎ−フェニル−１，１，１−トリフルオロメタンスルホンアミドヒドラゾン誘導体化合物および寄生生物の制御におけるそれらの使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| RU1799378C (ru) | 1993-02-28 |
| JPH0519543B2 (de) | 1993-03-17 |
| GB8631083D0 (en) | 1987-02-04 |
| ZA879706B (en) | 1988-06-21 |
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