IE41611B1 - Salicylanilide derivatives - Google Patents
Salicylanilide derivativesInfo
- Publication number
- IE41611B1 IE41611B1 IE1892/75A IE189275A IE41611B1 IE 41611 B1 IE41611 B1 IE 41611B1 IE 1892/75 A IE1892/75 A IE 1892/75A IE 189275 A IE189275 A IE 189275A IE 41611 B1 IE41611 B1 IE 41611B1
- Authority
- IE
- Ireland
- Prior art keywords
- radical
- formula
- nitro
- cyano
- methyl
- Prior art date
Links
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 title claims description 48
- -1 phenylazo, phenylthio, phenylsulphinyl Chemical group 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 125000001424 substituent group Chemical group 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 5
- 230000000507 anthelmentic effect Effects 0.000 claims abstract description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000003085 diluting agent Substances 0.000 claims abstract description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- 239000000243 solution Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 26
- 150000003254 radicals Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 241000242711 Fasciola hepatica Species 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229940125782 compound 2 Drugs 0.000 claims description 4
- 208000006275 fascioliasis Diseases 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims description 4
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- RZGWIZIPFZROQZ-UHFFFAOYSA-N 2-methoxy-n-phenylbenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=CC=C1 RZGWIZIPFZROQZ-UHFFFAOYSA-N 0.000 claims description 2
- KIQUWPFGHPCUTD-UHFFFAOYSA-N 3-tert-butyl-5-[(4-cyanophenyl)diazenyl]-2-hydroxy-6-methyl-N-(2-methyl-4-nitrophenyl)benzamide Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NC(=O)C1=C(C)C(N=NC=2C=CC(=CC=2)C#N)=CC(C(C)(C)C)=C1O KIQUWPFGHPCUTD-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical group O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000007764 o/w emulsion Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 150000003931 anilides Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 5
- 150000001448 anilines Chemical class 0.000 abstract description 4
- ZCEGRDRWYWAQRP-UHFFFAOYSA-N 5-bromo-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=C(Br)C=C(C(C)(C)C)C(O)=C1C(O)=O ZCEGRDRWYWAQRP-UHFFFAOYSA-N 0.000 abstract description 3
- GEDOJZVPHKBPGK-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfonyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1C GEDOJZVPHKBPGK-UHFFFAOYSA-N 0.000 abstract description 2
- HIOLDJXHPLHEJJ-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-2-hydroxy-6-methyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1C HIOLDJXHPLHEJJ-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 238000007911 parenteral administration Methods 0.000 abstract description 2
- 238000011200 topical administration Methods 0.000 abstract description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 3
- NCBOVAWEMBIIFK-UHFFFAOYSA-N (4-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=C(SCl)C=C1 NCBOVAWEMBIIFK-UHFFFAOYSA-N 0.000 abstract 1
- CDGTXPQHFRZVDR-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfanyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(SC=2C=CC(=CC=2)[N+]([O-])=O)=C1C CDGTXPQHFRZVDR-UHFFFAOYSA-N 0.000 abstract 1
- WIJXDAGWJCEHCI-UHFFFAOYSA-N 3-acetyl-6-acetyloxy-5-tert-butyl-6-hydroxy-2-methylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C(C)(=O)OC1(C(C(=O)O)C(=C(C=C1C(C)(C)C)C(C)=O)C)O WIJXDAGWJCEHCI-UHFFFAOYSA-N 0.000 abstract 1
- VJGOLFJCUHYYBA-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-(4-nitrophenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)(C)C)=CC(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 VJGOLFJCUHYYBA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 abstract 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- WFBJIYQFYASFQG-UHFFFAOYSA-N methyl 3-tert-butyl-5-cyano-2-hydroxy-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C(C#N)=CC(C(C)(C)C)=C1O WFBJIYQFYASFQG-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
- 229950000975 salicylanilide Drugs 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 5
- JXQCUCDXLSGQNZ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(O)=O JXQCUCDXLSGQNZ-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000004312 hexamethylene tetramine Substances 0.000 description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 4
- 229960004011 methenamine Drugs 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 2
- FNWNGQGTFICQJU-UHFFFAOYSA-N 2-hydroxy-6-methyl-3-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=C(C)C(C(O)=O)=C1O FNWNGQGTFICQJU-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- NTFYOZMLRFFCCO-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfinylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)C1=CC=C([N+]([O-])=O)C=C1 NTFYOZMLRFFCCO-UHFFFAOYSA-N 0.000 description 2
- BNNVEYJVDBVIPT-UHFFFAOYSA-N 3-tert-butyl-5-cyano-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(O)=O BNNVEYJVDBVIPT-UHFFFAOYSA-N 0.000 description 2
- SYUDPYSTWDKFHW-UHFFFAOYSA-N 3-tert-butyl-N-[4-(4-chlorophenyl)sulfonyl-2-(trifluoromethyl)phenyl]-5-cyano-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=C1C(F)(F)F SYUDPYSTWDKFHW-UHFFFAOYSA-N 0.000 description 2
- HOTZLWVITTVZGY-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F HOTZLWVITTVZGY-UHFFFAOYSA-N 0.000 description 2
- INVOPORANVEZKW-UHFFFAOYSA-N 5-acetyl-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC(=O)C1=CC(C(C)(C)C)=C(O)C(C(O)=O)=C1C INVOPORANVEZKW-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BDLNCFCZHNKBGI-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)benzene Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=C([N+]([O-])=O)C=C1 BDLNCFCZHNKBGI-UHFFFAOYSA-N 0.000 description 1
- DYSRXWYRUJCNFI-UHFFFAOYSA-N 2,4-dibromoaniline Chemical compound NC1=CC=C(Br)C=C1Br DYSRXWYRUJCNFI-UHFFFAOYSA-N 0.000 description 1
- MQFDMZNZEHTLND-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzoic acid Chemical compound CC(C)(C)OC1=CC=CC=C1C(O)=O MQFDMZNZEHTLND-UHFFFAOYSA-N 0.000 description 1
- QYUJQZXAVSLNJQ-UHFFFAOYSA-N 2-butoxy-6-methylbenzoic acid Chemical compound CCCCOC1=CC=CC(C)=C1C(O)=O QYUJQZXAVSLNJQ-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- UNNUAPUMHARYTI-UHFFFAOYSA-N 3,5-dichloro-4-phenylsulfanylaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1SC1=CC=CC=C1 UNNUAPUMHARYTI-UHFFFAOYSA-N 0.000 description 1
- BYTPSFUJMHGNTJ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2,4,5-trichlorophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC(Cl)=C(Cl)C=C1Cl BYTPSFUJMHGNTJ-UHFFFAOYSA-N 0.000 description 1
- FTDDOXPBPJVHSS-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=C([N+]([O-])=O)C=C1 FTDDOXPBPJVHSS-UHFFFAOYSA-N 0.000 description 1
- MYBHIAGMFYKNOD-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 MYBHIAGMFYKNOD-UHFFFAOYSA-N 0.000 description 1
- QDIWMPSEHALGOG-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-N-(2-methyl-4-nitrophenyl)benzamide Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1C QDIWMPSEHALGOG-UHFFFAOYSA-N 0.000 description 1
- ZAAMQANODYDRDF-UHFFFAOYSA-N 3-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=CC(C(O)=O)=C1O ZAAMQANODYDRDF-UHFFFAOYSA-N 0.000 description 1
- UYVGPJAVVDFFMQ-UHFFFAOYSA-N 3-tert-butyl-5-cyano-N-(2,4-dichlorophenyl)-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=C(Cl)C=C1Cl UYVGPJAVVDFFMQ-UHFFFAOYSA-N 0.000 description 1
- INGZNYJIZIILLF-UHFFFAOYSA-N 3-tert-butyl-5-cyano-N-(4-cyanophenyl)-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=C(C#N)C=C1 INGZNYJIZIILLF-UHFFFAOYSA-N 0.000 description 1
- UTJIUGLSTGACIV-UHFFFAOYSA-N 3-tert-butyl-5-formyl-2-hydroxy-6-methyl-N-(2-methyl-4-nitrophenyl)benzamide Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NC(=O)C1=C(C)C(C=O)=CC(C(C)(C)C)=C1O UTJIUGLSTGACIV-UHFFFAOYSA-N 0.000 description 1
- IEBSSLZPBITACV-UHFFFAOYSA-N 3-tert-butyl-N-[4-(4-chlorophenyl)sulfinylphenyl]-5-cyano-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=C(S(=O)C=2C=CC(Cl)=CC=2)C=C1 IEBSSLZPBITACV-UHFFFAOYSA-N 0.000 description 1
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- AEPOUVRRVQVORO-UHFFFAOYSA-N ClC1=C(NC(C=2C(O)=C(C=C(C2C)S(=O)C2=CC=C(C=C2)[N+](=O)[O-])C(C)(C)C)=O)C=CC(=C1)[N+](=O)[O-] Chemical compound ClC1=C(NC(C=2C(O)=C(C=C(C2C)S(=O)C2=CC=C(C=C2)[N+](=O)[O-])C(C)(C)C)=O)C=CC(=C1)[N+](=O)[O-] AEPOUVRRVQVORO-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OZFNLIJVZTVHFM-UHFFFAOYSA-N N-[2-bromo-4-(4-cyanophenyl)sulfanylphenyl]-3-tert-butyl-5-cyano-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC(C(=C1)Br)=CC=C1SC1=CC=C(C#N)C=C1 OZFNLIJVZTVHFM-UHFFFAOYSA-N 0.000 description 1
- UREMLJBWZRYLPM-UHFFFAOYSA-N N-[4-(4-bromophenyl)sulfonyl-2-(trifluoromethyl)phenyl]-3-tert-butyl-5-cyano-2-hydroxy-6-methylbenzamide Chemical compound FC(C1=C(NC(C=2C(O)=C(C=C(C2C)C#N)C(C)(C)C)=O)C=CC(=C1)S(=O)(=O)C1=CC=C(C=C1)Br)(F)F UREMLJBWZRYLPM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FSNXZBUDONSLOU-UHFFFAOYSA-N methyl 5-bromo-3-tert-butyl-2-hydroxy-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C(Br)=CC(C(C)(C)C)=C1O FSNXZBUDONSLOU-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- KXSARMHQKUGGEV-UHFFFAOYSA-N n-[4-(4-bromophenyl)sulfanyl-2-(trifluoromethyl)phenyl]-3-tert-butyl-5-cyano-2-hydroxy-6-methylbenzamide Chemical compound CC1=C(C#N)C=C(C(C)(C)C)C(O)=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1SC1=CC=C(Br)C=C1 KXSARMHQKUGGEV-UHFFFAOYSA-N 0.000 description 1
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
- XWLKIJOJBDAUOO-UHFFFAOYSA-N n-phenyl-2-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 XWLKIJOJBDAUOO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB41053/74A GB1493375A (en) | 1974-09-20 | 1974-09-20 | Salicylanilide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41611L IE41611L (en) | 1976-03-20 |
| IE41611B1 true IE41611B1 (en) | 1980-02-13 |
Family
ID=10417887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1892/75A IE41611B1 (en) | 1974-09-20 | 1975-08-28 | Salicylanilide derivatives |
Country Status (13)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4358443A (en) * | 1980-04-14 | 1982-11-09 | The Research Foundation Of State University Of New York | Method and composition for controlling the growth of microorganisms |
| US4287191A (en) * | 1980-04-14 | 1981-09-01 | The Research Foundation Of State University Of New York | Novel salicylanilides and microbiocidal compositions and uses thereof |
| US4939132A (en) * | 1985-04-15 | 1990-07-03 | The Research Foundation Of State University Of New York | Novel 5-alkylsulfonylsalicylanilides and microbiocidal compositions for controlling the growth of microorganisms |
| AU2002952597A0 (en) * | 2002-11-11 | 2002-11-28 | Schering-Plough Pty. Limited | Topical parasiticide formulations and methods of treatment |
| CN1886365A (zh) * | 2003-11-25 | 2006-12-27 | 诺沃挪第克公司 | 新水杨酰苯胺类 |
| JP2007513880A (ja) * | 2003-11-25 | 2007-05-31 | ノボ ノルディスク アクティーゼルスカブ | 新規のサリチルアニリド |
| AR056339A1 (es) * | 2005-05-09 | 2007-10-03 | Astrazeneca Ab | Derivados benzoicos |
| US20100041657A1 (en) * | 2005-05-11 | 2010-02-18 | Novo Nordick A/S | Haloalkylsulfone substituted compounds useful for treating obesity and diabetes |
| CN101180270A (zh) * | 2005-05-23 | 2008-05-14 | 诺和诺德公司 | 新颖的三氟甲氧基-取代的芳基酰基苯胺 |
| AU2008314979A1 (en) * | 2007-10-23 | 2009-04-30 | Institute Of Medicinal Molecular Design, Inc. | Inhibitor of PAI-1 production |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325353A (en) * | 1965-06-07 | 1967-06-13 | Monsanto Co | Gastropodicidally effective 2', 5-dichloro-4'-cyanosalicylanilides |
| US3798258A (en) * | 1970-03-13 | 1974-03-19 | Merck & Co Inc | Salicylanilides |
| US3839443A (en) * | 1971-10-04 | 1974-10-01 | Ferro Corp | Compounds of 2',4'-substituted anilides of substituted nitrosalicylic acid |
-
1974
- 1974-09-20 GB GB41053/74A patent/GB1493375A/en not_active Expired
-
1975
- 1975-08-28 IE IE1892/75A patent/IE41611B1/en unknown
- 1975-09-02 ZA ZA00755575A patent/ZA755575B/xx unknown
- 1975-09-15 US US05/613,559 patent/US4025647A/en not_active Expired - Lifetime
- 1975-09-16 HU HU75IE714A patent/HU173609B/hu unknown
- 1975-09-17 NL NL7510915A patent/NL7510915A/xx not_active Application Discontinuation
- 1975-09-18 DD DD188428A patent/DD125586A5/xx unknown
- 1975-09-19 FR FR7528860A patent/FR2285139A1/fr active Granted
- 1975-09-19 JP JP50113520A patent/JPS51125037A/ja active Pending
- 1975-09-19 BE BE160233A patent/BE833648A/xx unknown
- 1975-09-19 DE DE19752541923 patent/DE2541923A1/de not_active Withdrawn
- 1975-09-19 AR AR260466A patent/AR210585A1/es active
- 1975-09-20 ES ES441138A patent/ES441138A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51125037A (en) | 1976-11-01 |
| FR2285139A1 (fr) | 1976-04-16 |
| HU173609B (hu) | 1979-06-28 |
| AR210585A1 (es) | 1977-08-31 |
| DE2541923A1 (de) | 1976-04-01 |
| ZA755575B (en) | 1976-07-28 |
| GB1493375A (en) | 1977-11-30 |
| FR2285139B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-28 |
| NL7510915A (nl) | 1976-03-23 |
| IE41611L (en) | 1976-03-20 |
| DD125586A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-04 |
| AU8451775A (en) | 1977-03-10 |
| ES441138A1 (es) | 1977-07-01 |
| US4025647A (en) | 1977-05-24 |
| BE833648A (fr) | 1976-03-19 |
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| CH498856A (de) | Verfahren zur Herstellung von neuen Furazanderivaten |