DE2031227A1 - Neue substituierte Sahcylsauren und Verfahren zu ihrer Herstellung - Google Patents
Neue substituierte Sahcylsauren und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2031227A1 DE2031227A1 DE19702031227 DE2031227A DE2031227A1 DE 2031227 A1 DE2031227 A1 DE 2031227A1 DE 19702031227 DE19702031227 DE 19702031227 DE 2031227 A DE2031227 A DE 2031227A DE 2031227 A1 DE2031227 A1 DE 2031227A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkyl
- acid
- alkyl
- amino
- alkylamino
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 hydroxy, amino Chemical group 0.000 claims description 111
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 229960004889 salicylic acid Drugs 0.000 claims description 27
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003870 salicylic acids Chemical class 0.000 claims description 7
- 150000001448 anilines Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 4
- ZHBQARHZUMHTRK-UHFFFAOYSA-N n-(2-methoxyphenyl)benzamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC=CC=C1 ZHBQARHZUMHTRK-UHFFFAOYSA-N 0.000 claims description 4
- RVIOLHZEGBIJDK-UHFFFAOYSA-N 2-(benzylamino)oxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1ONCC1=CC=CC=C1 RVIOLHZEGBIJDK-UHFFFAOYSA-N 0.000 claims description 3
- AGUNHXLLDZAFJT-UHFFFAOYSA-N 2-benzamidooxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1ONC(=O)C1=CC=CC=C1 AGUNHXLLDZAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000003935 benzaldehydes Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- UYKVWAQEMQDRGG-UHFFFAOYSA-N n-(2-hydroxyphenyl)benzamide Chemical compound OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 UYKVWAQEMQDRGG-UHFFFAOYSA-N 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- HYXQCNIDWFATGE-UHFFFAOYSA-N 3-phenylmorpholin-4-amine Chemical class NN1C(COCC1)C1=CC=CC=C1 HYXQCNIDWFATGE-UHFFFAOYSA-N 0.000 claims 1
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229960001860 salicylate Drugs 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 206010061218 Inflammation Diseases 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 3
- 229960004963 mesalazine Drugs 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VYMHOFMHLOUATI-UHFFFAOYSA-N 2-(benzylideneamino)-4-methoxybenzoic acid Chemical class C(C1=CC=CC=C1)=NC1=C(C(=O)O)C=CC(=C1)OC VYMHOFMHLOUATI-UHFFFAOYSA-N 0.000 description 2
- SMUHKNDBAXIQON-UHFFFAOYSA-N 2-(benzylideneamino)oxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1ON=CC1=CC=CC=C1 SMUHKNDBAXIQON-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- ZPBMOTGPFVLBMN-UHFFFAOYSA-N 3-(methoxymethyl)benzoic acid Chemical compound COCC1=CC=CC(C(O)=O)=C1 ZPBMOTGPFVLBMN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940071248 anisate Drugs 0.000 description 2
- 230000001567 anti-fibrinolytic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 238000006480 benzoylation reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KBOPZPXVLCULAV-UHFFFAOYSA-M mesalaminate(1-) Chemical compound NC1=CC=C(O)C(C([O-])=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-M 0.000 description 2
- YUHSMQQNPRLEEJ-UHFFFAOYSA-N methyl 3-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CBr)=C1 YUHSMQQNPRLEEJ-UHFFFAOYSA-N 0.000 description 2
- MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical class COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- OXCREIAATRYJNU-UHFFFAOYSA-N n-benzyl-2-methoxyaniline Chemical class COC1=CC=CC=C1NCC1=CC=CC=C1 OXCREIAATRYJNU-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229960000581 salicylamide Drugs 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- LUJNPFWZXIGIPS-UHFFFAOYSA-N (2,5-dimethylphenyl)methanamine Chemical compound CC1=CC=C(C)C(CN)=C1 LUJNPFWZXIGIPS-UHFFFAOYSA-N 0.000 description 1
- KYZSFZRRZVYDDA-UHFFFAOYSA-N 1,5-dimethylcyclohexa-2,4-dien-1-amine Chemical compound CC1(N)CC(=CC=C1)C KYZSFZRRZVYDDA-UHFFFAOYSA-N 0.000 description 1
- DHOOGSFDAOJIOU-UHFFFAOYSA-N 1-methoxy-2-(nitromethyl)benzene Chemical compound COC1=CC=CC=C1C[N+]([O-])=O DHOOGSFDAOJIOU-UHFFFAOYSA-N 0.000 description 1
- XHONYVFDZSPELQ-UHFFFAOYSA-N 1-methoxy-3-(trifluoromethyl)benzene Chemical compound COC1=CC=CC(C(F)(F)F)=C1 XHONYVFDZSPELQ-UHFFFAOYSA-N 0.000 description 1
- LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 1
- YAENNUHPRIEHDG-UHFFFAOYSA-N 2-(benzylamino)-4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C(NCC=2C=CC=CC=2)=C1 YAENNUHPRIEHDG-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
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- 239000011697 sodium iodate Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- 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
- 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
- C07C65/21—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 ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83662369A | 1969-06-25 | 1969-06-25 | |
| US3032270A | 1970-04-20 | 1970-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2031227A1 true DE2031227A1 (de) | 1971-01-07 |
Family
ID=26705913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702031227 Pending DE2031227A1 (de) | 1969-06-25 | 1970-06-24 | Neue substituierte Sahcylsauren und Verfahren zu ihrer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4920197B1 (enrdf_load_stackoverflow) |
| CH (1) | CH536278A (enrdf_load_stackoverflow) |
| DE (1) | DE2031227A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2053015A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1268465A (enrdf_load_stackoverflow) |
| NL (1) | NL7008623A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986003199A1 (en) * | 1984-11-29 | 1986-06-05 | Italfarmaco S.P.A. | Amino-salicylic acid derivatives and pharmaceutical compositions |
| WO1986005485A1 (en) * | 1985-03-14 | 1986-09-25 | Smith Kline Dauelsberg Gmbh | Amides of non-steroidal anti-inflammatory carboxylic acids |
| WO2001079153A1 (en) * | 2000-04-19 | 2001-10-25 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US6573402B1 (en) | 2000-04-20 | 2003-06-03 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US7189878B2 (en) | 2002-06-19 | 2007-03-13 | Neurotech Co., Ltd. | Tetrafluorobenzyl derivatives and pharmaceutical composition for preventing and treating acute and chronic neurodegenerative diseases in central nervous system containing the same |
| US8455470B2 (en) | 2006-04-13 | 2013-06-04 | Neurotech Pharmaceuticals Co., Ltd | Pharmaceutical composition for treating or preventing degenerative and inflammatory diseases |
| US8686185B2 (en) | 2007-11-12 | 2014-04-01 | Neurotech Pharmaceuticals Co., Ltd. | Manufacturing method of 2-hydroxy-5-phenylalkylaminobenzoic acid derivatives and their salts |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5283169U (enrdf_load_stackoverflow) * | 1975-12-18 | 1977-06-21 | ||
| FR2405241A1 (fr) * | 1977-10-06 | 1979-05-04 | Rorer Inc William H | Benzylideneaniline et ses derives, utilises pour le traitement d'inflammation chez les animaux a sang chaud |
| IT1244873B (it) * | 1990-09-12 | 1994-09-12 | Depha Team Srl | Derivati dell'acido 5-aminosalicilico (5-asa) per la terapia delle infiammazioni croniche intestinali |
| KR100668111B1 (ko) | 2005-07-28 | 2007-01-12 | (주)에스에이치제약 | 강력한 항산화 효과를 가짐으로써 급성 및 퇴행성 뇌신경계질환의 예방 및 치료에 이용 가능한 신규물질인아미노살리실산 유도체와 그 염의 제조방법 |
| KR100639551B1 (ko) | 2005-07-28 | 2006-10-30 | (주)에스에이치제약 | 5-(치환된 페닐알킬)아미노살리실산 화합물의 제조 방법 |
| JP7437073B2 (ja) * | 2019-07-08 | 2024-02-22 | ジーエヌティー ファーマ カンパニー， リミテッド | ５－ベンジルアミノサリチル酸誘導体を含む化粧品組成物及びその局所使用方法 |
-
1970
- 1970-06-12 NL NL7008623A patent/NL7008623A/xx unknown
- 1970-06-18 GB GB2966870A patent/GB1268465A/en not_active Expired
- 1970-06-22 JP JP5358270A patent/JPS4920197B1/ja active Pending
- 1970-06-23 CH CH950370A patent/CH536278A/de not_active IP Right Cessation
- 1970-06-24 DE DE19702031227 patent/DE2031227A1/de active Pending
- 1970-06-24 FR FR7023328A patent/FR2053015A1/fr not_active Withdrawn
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986003199A1 (en) * | 1984-11-29 | 1986-06-05 | Italfarmaco S.P.A. | Amino-salicylic acid derivatives and pharmaceutical compositions |
| WO1986005485A1 (en) * | 1985-03-14 | 1986-09-25 | Smith Kline Dauelsberg Gmbh | Amides of non-steroidal anti-inflammatory carboxylic acids |
| US4783487A (en) * | 1985-03-14 | 1988-11-08 | Smith Kline Dauelsberg Gmbh | N-(1-carboxy-2-hydroxy-5-phenyl)-2-(6-methoxy-2-naphthyl)propionamide and anti-inflammatory use thereof |
| JPH0755921B2 (ja) * | 1985-03-14 | 1995-06-14 | スミス・クライン・ダウエルスベルク・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | アミド類 |
| WO2001079153A1 (en) * | 2000-04-19 | 2001-10-25 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US8211877B2 (en) | 2000-04-20 | 2012-07-03 | Neurotech Pharmaceuticals Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US6964982B2 (en) | 2000-04-20 | 2005-11-15 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US7750045B2 (en) | 2000-04-20 | 2010-07-06 | Neurotech Pharmaceuticals Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US6573402B1 (en) | 2000-04-20 | 2003-06-03 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US8211878B2 (en) | 2000-04-20 | 2012-07-03 | Neurotech Pharmaceuticals Co., Ltd. | Method for reducing neuronal death in nervous system injuries resulting from amyotrophic lateral sclerosis |
| US7189878B2 (en) | 2002-06-19 | 2007-03-13 | Neurotech Co., Ltd. | Tetrafluorobenzyl derivatives and pharmaceutical composition for preventing and treating acute and chronic neurodegenerative diseases in central nervous system containing the same |
| US7319160B2 (en) | 2002-06-19 | 2008-01-15 | Amkor Pharma, Inc. | Tetrafluorobenzyl derivatives and pharmaceutical composition for preventing and treating acute and chronic neurodegenerative diseases in central nervous system containing the same |
| US7371896B2 (en) | 2002-06-19 | 2008-05-13 | Amkor Pharma, Inc. | Tetrafluorobenzyl derivatives and pharmaceutical composition for preventing and treating acute and chronic neurodegenerative diseases in central nervous system containing the same |
| US7511074B2 (en) | 2002-06-19 | 2009-03-31 | Amkor Pharma, Inc. | Tetrafluorobenzyl derivatives and pharmaceutical composition for preventing and treating acute and chronic neurodegenerative diseases in central nervous system containing the same |
| US8455470B2 (en) | 2006-04-13 | 2013-06-04 | Neurotech Pharmaceuticals Co., Ltd | Pharmaceutical composition for treating or preventing degenerative and inflammatory diseases |
| US8598383B2 (en) | 2006-04-13 | 2013-12-03 | Neurotech Pharmaceuticals Co., Ltd. | Pharmaceutical composition for treating or preventing degenerative and inflammatory diseases |
| US8686185B2 (en) | 2007-11-12 | 2014-04-01 | Neurotech Pharmaceuticals Co., Ltd. | Manufacturing method of 2-hydroxy-5-phenylalkylaminobenzoic acid derivatives and their salts |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2053015A1 (enrdf_load_stackoverflow) | 1971-04-16 |
| JPS4920197B1 (enrdf_load_stackoverflow) | 1974-05-23 |
| NL7008623A (enrdf_load_stackoverflow) | 1970-12-29 |
| GB1268465A (en) | 1972-03-29 |
| CH536278A (de) | 1973-04-30 |
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