FI71126C - Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider - Google Patents
Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider Download PDFInfo
- Publication number
- FI71126C FI71126C FI790182A FI790182A FI71126C FI 71126 C FI71126 C FI 71126C FI 790182 A FI790182 A FI 790182A FI 790182 A FI790182 A FI 790182A FI 71126 C FI71126 C FI 71126C
- Authority
- FI
- Finland
- Prior art keywords
- methoxy
- amino
- acid
- formula
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- -1 ALLYL-2-PYRROLIDINYLMETHYL Chemical class 0.000 title claims description 12
- BQLQKKOXETVOFA-UHFFFAOYSA-N O=[S-](=O)C1=CC=CC=C1 Chemical compound O=[S-](=O)C1=CC=CC=C1 BQLQKKOXETVOFA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- QOWLKTWQYURQLI-UHFFFAOYSA-N 4-amino-2-methoxy-5-sulfanylbenzoic acid Chemical compound COC1=CC(N)=C(S)C=C1C(O)=O QOWLKTWQYURQLI-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 55
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 12
- OJVNCXHGGYYOPH-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC(C(O)=O)=C(OC)C=C1N OJVNCXHGGYYOPH-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 230000000794 anti-serotonin Effects 0.000 description 8
- 239000003420 antiserotonin agent Substances 0.000 description 8
- 208000019695 Migraine disease Diseases 0.000 description 7
- 206010027599 migraine Diseases 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- BAXPWPBNRAGVGF-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxy-n-[(1-methylpyrrolidin-2-yl)methyl]benzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NCC2N(CCC2)C)=C1OC BAXPWPBNRAGVGF-UHFFFAOYSA-N 0.000 description 6
- 208000009079 Bronchial Spasm Diseases 0.000 description 6
- 208000014181 Bronchial disease Diseases 0.000 description 6
- 206010006482 Bronchospasm Diseases 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000002903 catalepsic effect Effects 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229940095064 tartrate Drugs 0.000 description 6
- 241000700198 Cavia Species 0.000 description 5
- 208000007107 Stomach Ulcer Diseases 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 4
- PGTLUUCBHDLKKY-UHFFFAOYSA-N 4-amino-2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC(N)=C(S(C)(=O)=O)C=C1C(O)=O PGTLUUCBHDLKKY-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 3
- JEZWENIMQLYTHI-UHFFFAOYSA-N 4-amino-2-methoxy-5-methylbenzenecarbothioic s-acid Chemical compound COC1=CC(N)=C(C)C=C1C(O)=S JEZWENIMQLYTHI-UHFFFAOYSA-N 0.000 description 3
- HHGKDYZRJZHFTB-UHFFFAOYSA-N 4-amino-2-methoxy-5-propylsulfonylbenzoic acid Chemical compound CCCS(=O)(=O)C1=CC(C(O)=O)=C(OC)C=C1N HHGKDYZRJZHFTB-UHFFFAOYSA-N 0.000 description 3
- XWQQMEILWYTOFI-UHFFFAOYSA-N 4-amino-2-methoxy-N-[(1-methylpyrrolidin-2-yl)methyl]-5-propan-2-ylsulfonylbenzamide Chemical compound CN1C(CCC1)CNC(C1=C(C=C(C(=C1)S(=O)(=O)C(C)C)N)OC)=O XWQQMEILWYTOFI-UHFFFAOYSA-N 0.000 description 3
- VNUDKOUMRVOMAU-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxy-N-[(1-propylpyrrolidin-2-yl)methyl]benzamide Chemical compound C(CC)N1C(CCC1)CNC(C1=C(C=C(C(=C1)S(=O)(=O)CC)N)OC)=O VNUDKOUMRVOMAU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 230000003474 anti-emetic effect Effects 0.000 description 3
- 239000002111 antiemetic agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 201000005917 gastric ulcer Diseases 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960004940 sulpiride Drugs 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BSAJVYWMTCSLTM-UHFFFAOYSA-N 4-amino-2-methoxy-5-propan-2-ylsulfonylbenzoic acid Chemical compound COC1=C(C(=O)O)C=C(C(=C1)N)S(=O)(=O)C(C)C BSAJVYWMTCSLTM-UHFFFAOYSA-N 0.000 description 2
- WREAFQNIZXRSPF-UHFFFAOYSA-N 4-amino-2-methoxy-5-propylbenzenecarbothioic s-acid Chemical compound CCCC1=CC(C(S)=O)=C(OC)C=C1N WREAFQNIZXRSPF-UHFFFAOYSA-N 0.000 description 2
- BVCKAIGDWABZIE-UHFFFAOYSA-N 4-amino-5-ethylsulfanyl-2-methoxybenzoic acid Chemical compound CCSC1=CC(C(O)=O)=C(OC)C=C1N BVCKAIGDWABZIE-UHFFFAOYSA-N 0.000 description 2
- PFXOJRCOFMOPTK-UHFFFAOYSA-N 4-amino-n-(2,5-dichloropentyl)-5-ethylsulfonyl-2-methoxybenzamide Chemical compound CCS(=O)(=O)C1=CC(C(=O)NCC(Cl)CCCCl)=C(OC)C=C1N PFXOJRCOFMOPTK-UHFFFAOYSA-N 0.000 description 2
- SZQIUFIQZCNHHN-UHFFFAOYSA-N 4-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(C)(=O)=O)=C(N)C=C1OC SZQIUFIQZCNHHN-UHFFFAOYSA-N 0.000 description 2
- OHXAATSCRKQXOX-UHFFFAOYSA-N 4-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-propylsulfonylbenzamide Chemical compound C1=C(N)C(S(=O)(=O)CCC)=CC(C(=O)NCC2N(CCC2)CC)=C1OC OHXAATSCRKQXOX-UHFFFAOYSA-N 0.000 description 2
- TZPHEDZMFSJFOE-UHFFFAOYSA-N 4-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC TZPHEDZMFSJFOE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HWSDJPGEAJMITN-UHFFFAOYSA-N CC(C)C1=CC(=C(C=C1N)OC)C(=O)S Chemical compound CC(C)C1=CC(=C(C=C1N)OC)C(=O)S HWSDJPGEAJMITN-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003354 anti-apomorphinic effect Effects 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 229940054066 benzamide antipsychotics Drugs 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- 210000000621 bronchi Anatomy 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 2
- 229960004943 ergotamine Drugs 0.000 description 2
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- TZFATUOLQKYADA-UHFFFAOYSA-N (1-propylpyrrolidin-2-yl)methanamine Chemical compound CCCN1CCCC1CN TZFATUOLQKYADA-UHFFFAOYSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical class ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- ATGSLQBVSZNJMT-UHFFFAOYSA-N 2,5-dichloropentan-1-amine;hydrochloride Chemical compound Cl.NCC(Cl)CCCCl ATGSLQBVSZNJMT-UHFFFAOYSA-N 0.000 description 1
- RGIPZYBGETZBFO-UHFFFAOYSA-N 2-propylsulfonylbenzamide Chemical compound CCCS(=O)(=O)C1=CC=CC=C1C(N)=O RGIPZYBGETZBFO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- QEVBNUFEGDVWRM-UHFFFAOYSA-N 4-amino-2-methoxy-5-methylsulfonylbenzamide Chemical compound COC1=C(C(=O)N)C=C(C(=C1)N)S(=O)(=O)C QEVBNUFEGDVWRM-UHFFFAOYSA-N 0.000 description 1
- IMNSNKQPRAMHHM-UHFFFAOYSA-N 4-amino-2-methoxy-n-[(1-methylpyrrolidin-2-yl)methyl]-5-methylsulfonylbenzamide Chemical compound COC1=CC(N)=C(S(C)(=O)=O)C=C1C(=O)NCC1N(C)CCC1 IMNSNKQPRAMHHM-UHFFFAOYSA-N 0.000 description 1
- AOYPYBTXGAQQBP-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxy-N-(1-pyrrolidin-2-ylpropyl)benzamide Chemical compound C1CCNC1C(CC)NC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC AOYPYBTXGAQQBP-UHFFFAOYSA-N 0.000 description 1
- PPVCNUUILQZGSD-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid;hydrate Chemical compound O.CCS(=O)(=O)C1=CC(C(O)=O)=C(OC)C=C1N PPVCNUUILQZGSD-UHFFFAOYSA-N 0.000 description 1
- SIBDHPSAYKTBHI-UHFFFAOYSA-N CCCOC1=CC(=CC(=C1CN2CCCC2)C(=O)N)S(=O)(=O)N Chemical compound CCCOC1=CC(=CC(=C1CN2CCCC2)C(=O)N)S(=O)(=O)N SIBDHPSAYKTBHI-UHFFFAOYSA-N 0.000 description 1
- LCMQPLQHKBJJHJ-UHFFFAOYSA-N CCN1C(CN(C(C(C(OC)=C2)=CC(S(CC)(=O)=O)=C2N)=O)O)CCC1 Chemical compound CCN1C(CN(C(C(C(OC)=C2)=CC(S(CC)(=O)=O)=C2N)=O)O)CCC1 LCMQPLQHKBJJHJ-UHFFFAOYSA-N 0.000 description 1
- FYGVSXFAZSYNTE-UHFFFAOYSA-N CCNC(=O)C1C=C(C(=CC1(CN2CCCC2)OC)N)S(=O)(=O)CC Chemical compound CCNC(=O)C1C=C(C(=CC1(CN2CCCC2)OC)N)S(=O)(=O)CC FYGVSXFAZSYNTE-UHFFFAOYSA-N 0.000 description 1
- KDQMXSAWHDSKTJ-UHFFFAOYSA-N CCS(C(C(N)=C1)=CC(C(N(CC2N(C)CCC2)O)=O)=C1OC)(=O)=O Chemical compound CCS(C(C(N)=C1)=CC(C(N(CC2N(C)CCC2)O)=O)=C1OC)(=O)=O KDQMXSAWHDSKTJ-UHFFFAOYSA-N 0.000 description 1
- FUGKHCDOOQOSTM-UHFFFAOYSA-N CNC(C1C(C=C(C(=C1)S(=O)(=O)CC)N)(OC)CN1CCCC1)=O Chemical compound CNC(C1C(C=C(C(=C1)S(=O)(=O)CC)N)(OC)CN1CCCC1)=O FUGKHCDOOQOSTM-UHFFFAOYSA-N 0.000 description 1
- QXNOBMLEVVCSDD-UHFFFAOYSA-N COC1=C(C(=S)O)C=C(C(=C1)N)CC.C(C)N1C(CCC1)CNC(C1=C(C=C(C(=C1)S(=O)(=O)CC)N)OC)=O Chemical compound COC1=C(C(=S)O)C=C(C(=C1)N)CC.C(C)N1C(CCC1)CNC(C1=C(C=C(C(=C1)S(=O)(=O)CC)N)OC)=O QXNOBMLEVVCSDD-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- JWSIZPAOIFLWKM-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[3-(dimethylamino)-4-hydroxypyrrolidin-1-yl]methanone Chemical compound CN(C)C1CN(CC1O)C(=O)c1cccc(Oc2cc(CN)cc(n2)C(F)(F)F)c1 JWSIZPAOIFLWKM-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- BNPSSFBOAGDEEL-UHFFFAOYSA-N albuterol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 BNPSSFBOAGDEEL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000002460 anti-migrenic effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI861130A FI73412C (fi) | 1978-01-20 | 1986-03-18 | 2-metoxi-4-amino-5-alkyltio- (eller alkylsulfonyl)benzoesyraderivat. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801632 | 1978-01-20 | ||
| FR7801632A FR2415099A1 (fr) | 1978-01-20 | 1978-01-20 | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI790182A7 FI790182A7 (fi) | 1979-07-21 |
| FI71126B FI71126B (fi) | 1986-08-14 |
| FI71126C true FI71126C (fi) | 1986-11-24 |
Family
ID=9203689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI790182A FI71126C (fi) | 1978-01-20 | 1979-01-19 | Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider |
Country Status (42)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| NZ199080A (en) * | 1980-12-12 | 1984-07-31 | Beecham Group Ltd | 2-alkoxy-4-amino-5-alkylsulphonyl-n-(3beta-(8-hydrocarbyl-8-azabicyclo (3,2,1)octyl))benzamides |
| FR2550447B1 (fr) * | 1983-08-10 | 1986-01-17 | Ile De France | Application du n-(ally-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide comme antiagregant plaquettaire |
| FR2574795B1 (fr) * | 1984-12-18 | 1987-11-20 | Ile De France | Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide |
| FR2584401B1 (fr) * | 1985-07-04 | 1987-11-20 | Ile De France | Nouveau benzamide, son procede de preparation et son application dans le domaine therapeutique |
| US5227388A (en) * | 1989-12-26 | 1993-07-13 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
| FR2699533A1 (fr) * | 1992-12-21 | 1994-06-24 | Mouhtaram Mohamed | Dérivés de N-((1,4-dialkyl-6-arylpipérazine-2-yl)méthyl)benzamides. (Isomères cis et trans) Propriétés pharmacologiques et applications. |
| FR2753376B1 (fr) * | 1996-09-18 | 1998-10-16 | Synthelabo | Compositions pharmaceutiques comprenant de l'amisulpride et leurs applications therapeutiques |
| FR2762213B1 (fr) * | 1997-04-18 | 1999-05-14 | Synthelabo | Composition pharmaceutique a retention gastrique |
| US6169094B1 (en) * | 1998-07-14 | 2001-01-02 | Sanofi-Synthelabo | Compositions of (S) (-)-amisulpride |
| DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| CN1791430A (zh) * | 2003-05-16 | 2006-06-21 | 辉瑞产品公司 | 非典型抗精神病药物和gaba调节剂、抗惊厥药物或苯并二氮杂䓬类的治疗性组合 |
| FR2857263B1 (fr) * | 2003-07-09 | 2005-09-09 | Sanofi Synthelabo | Nouvelle composition pharmaceutique solide comprenant de l'amisulpride |
| CA2565996A1 (en) * | 2004-05-11 | 2005-11-17 | Pfizer Products Inc. | Combination of atypical antipsychotics and 5-ht1b receptor antagonists |
| CN101198323A (zh) * | 2005-04-22 | 2008-06-11 | 惠氏公司 | 用于治疗或预防精神障碍的治疗组合 |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| US7825156B2 (en) * | 2007-02-02 | 2010-11-02 | Copharms | Method of treating bipolar depression with a benzamide derivative |
| JP2011526881A (ja) * | 2008-06-25 | 2011-10-20 | ファイザー・インク | ジアリール化合物およびそれらの使用 |
| US20100105755A1 (en) * | 2008-09-12 | 2010-04-29 | Auspex Pharmaceuticals, Inc. | Substituted benzamide modulators of dopamine receptor |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
| CN101898991B (zh) * | 2009-05-31 | 2013-09-25 | 江苏天士力帝益药业有限公司 | 一种(s)(-)-氨磺必利d-(-)-酒石酸盐的合成方法 |
| CN101628886B (zh) * | 2009-08-25 | 2012-12-12 | 北京紫萌同达科技有限公司 | 一种2-甲氧基-4-氨基-5-乙砜基苯甲酸的合成方法 |
| AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| GB201004020D0 (en) | 2010-03-11 | 2010-04-21 | Acacia Pharma Ltd | New therapeutic use |
| BR112012031959A2 (pt) | 2010-06-17 | 2015-09-22 | Lupin Ltd | um processo aperfeiçoado para preparação de amisulpride |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| CN103319384A (zh) * | 2013-06-18 | 2013-09-25 | 苏州诚和医药化学有限公司 | 制备2-甲氧基-4-氨基-5-乙砜基苯甲酸的方法 |
| CN103304453A (zh) * | 2013-06-18 | 2013-09-18 | 苏州诚和医药化学有限公司 | 两步法合成2-甲氧基-4-氨基-5-乙砜基苯甲酸 |
| CN103450058B (zh) * | 2013-09-18 | 2015-10-14 | 广安凯特医药化工有限公司 | 一种氨磺必利酸的制备方法 |
| CN104725292B (zh) * | 2015-03-23 | 2017-07-25 | 湖北荆江源制药股份有限公司 | 一种(s)(‑)‑氨磺必利的制备方法 |
| GB201618425D0 (en) * | 2016-11-01 | 2016-12-14 | Acacia Pharma Ltd | method |
| US11377421B2 (en) | 2016-11-28 | 2022-07-05 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
| MA46901A (fr) | 2016-11-28 | 2019-10-02 | Lb Pharmaceuticals Inc | Agents psychotropes et leurs utilisations |
| CN106995397B (zh) * | 2016-12-12 | 2020-01-14 | 河北医科大学 | R-氨磺必利药用盐、制备方法、晶型及其用途 |
| GB201702250D0 (en) | 2017-02-10 | 2017-03-29 | Acacia Pharma Ltd | Method |
| CA3088356A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Crystal forms and production methods thereof |
| CN118593482A (zh) | 2017-12-05 | 2024-09-06 | 赛诺维信制药公司 | 非外消旋混合物及其用途 |
| CN110790693A (zh) * | 2018-08-02 | 2020-02-14 | 北京万全德众医药生物技术有限公司 | 一种(s)(-)-氨磺必利的制备方法 |
| JP2022535893A (ja) | 2019-06-04 | 2022-08-10 | サノビオン ファーマシューティカルズ インク | 放出調節製剤およびその使用 |
| USD1047552S1 (en) * | 2021-04-23 | 2024-10-22 | Krueger International, Inc. | Furniture leg with frame |
| CN116003304A (zh) * | 2023-02-08 | 2023-04-25 | 浙江皓华制药有限公司 | 一种氨磺必利的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| FR2244760B1 (OSRAM) * | 1973-09-25 | 1980-06-27 | Ile De France | |
| FR2299862B1 (en) * | 1975-02-07 | 1978-07-21 | Soc Et Scient Et Ind | Substd. N-(1-benzylpyrrolidinyl-2-alkyl)benzamides - used as antiemetics, anti-ulcer agents and CNS active |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
| IE42210B1 (en) * | 1974-12-18 | 1980-06-18 | Synthelabo | 2-methoxy-benzamide derivatives |
-
1978
- 1978-01-20 FR FR7801632A patent/FR2415099A1/fr active Granted
- 1978-12-07 BE BE1009179A patent/BE872585A/xx not_active IP Right Cessation
-
1979
- 1979-01-10 BG BG042018A patent/BG31496A3/xx unknown
- 1979-01-10 AR AR275115A patent/AR221354A1/es active
- 1979-01-10 BG BG043588A patent/BG31497A3/xx unknown
- 1979-01-11 YU YU50/79A patent/YU42172B/xx unknown
- 1979-01-11 IL IL56411A patent/IL56411A/xx unknown
- 1979-01-11 ES ES476755A patent/ES476755A1/es not_active Expired
- 1979-01-11 IN IN21/CAL/79A patent/IN150226B/en unknown
- 1979-01-12 PT PT69068A patent/PT69068A/pt unknown
- 1979-01-13 DE DE2901181A patent/DE2901181C2/de not_active Expired
- 1979-01-15 AU AU43373/79A patent/AU528561B2/en not_active Expired
- 1979-01-15 CH CH37379A patent/CH637927A5/fr active Protection Beyond IP Right Term
- 1979-01-15 GR GR58090A patent/GR64431B/el unknown
- 1979-01-15 NZ NZ189378A patent/NZ189378A/xx unknown
- 1979-01-15 LU LU80786A patent/LU80786A1/xx unknown
- 1979-01-16 RO RO7996297A patent/RO76393A/ro unknown
- 1979-01-16 SE SE7900380A patent/SE448874B/sv not_active IP Right Cessation
- 1979-01-16 RO RO79103170A patent/RO80311A/ro unknown
- 1979-01-16 MC MC791357A patent/MC1232A1/xx unknown
- 1979-01-17 EG EG29/79A patent/EG14045A/xx active
- 1979-01-17 CY CY1201A patent/CY1201A/en unknown
- 1979-01-17 GB GB8118999A patent/GB2083458B/en not_active Expired
- 1979-01-17 GB GB791690A patent/GB2012765B/en not_active Expired
- 1979-01-18 ZM ZM5/79A patent/ZM579A1/xx unknown
- 1979-01-18 DK DK020979A patent/DK158346C/da not_active IP Right Cessation
- 1979-01-18 US US06/004,397 patent/US4294828A/en not_active Expired - Lifetime
- 1979-01-18 IT IT47706/79A patent/IT1164655B/it active Protection Beyond IP Right Term
- 1979-01-18 NO NO790180A patent/NO151320C/no unknown
- 1979-01-19 CS CS79443A patent/CS226181B2/cs unknown
- 1979-01-19 PL PL1979224894A patent/PL118151B1/pl unknown
- 1979-01-19 MX MX797669U patent/MX5793E/es unknown
- 1979-01-19 MX MX7911208U patent/MX7623E/es unknown
- 1979-01-19 CA CA319,969A patent/CA1101430A/en not_active Expired
- 1979-01-19 SU SU792714652A patent/SU820659A3/ru active
- 1979-01-19 AT AT0039879A patent/AT377977B/de not_active IP Right Cessation
- 1979-01-19 PL PL1979212899A patent/PL116532B1/pl unknown
- 1979-01-19 FI FI790182A patent/FI71126C/fi not_active IP Right Cessation
- 1979-01-19 OA OA56717A patent/OA06156A/xx unknown
- 1979-01-19 NL NL7900457A patent/NL191707C/xx not_active IP Right Cessation
- 1979-01-19 HU HU79SO1241A patent/HU179793B/hu unknown
- 1979-01-19 JP JP54005483A patent/JPS6049192B2/ja not_active Expired
- 1979-01-19 ZA ZA79219A patent/ZA79219B/xx unknown
- 1979-01-22 DD DD79210583A patent/DD141520A5/de unknown
- 1979-01-30 IE IE92/79A patent/IE47798B1/en active Protection Beyond IP Right Term
- 1979-02-16 ES ES477782A patent/ES477782A1/es not_active Expired
- 1979-08-16 AR AR277738A patent/AR220574A1/es active
- 1979-11-06 PH PH23252A patent/PH15725A/en unknown
-
1980
- 1980-08-20 PH PH24465A patent/PH22287A/en unknown
-
1981
- 1981-10-09 US US06/310,336 patent/US4401822A/en not_active Expired - Lifetime
-
1983
- 1983-02-04 YU YU254/83A patent/YU41278B/xx unknown
-
1984
- 1984-02-16 HK HK121/84A patent/HK12184A/xx not_active IP Right Cessation
-
1986
- 1986-09-09 SE SE8603773A patent/SE460968B/sv not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI71126C (fi) | Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider | |
| CA1238906A (en) | Benzofuran- and benzopyran-carboxamide derivatives | |
| IE840655L (en) | 1,3-thiazolidine derivatives | |
| HU220066B (hu) | Imidazo[1,2-a]piridinek alkoxi-alkil-karbamátjai, alkalmazásuk, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| EP0874849B1 (en) | 2,7-substituted octahydro-pyrrolo 1,2-a]pyrazine derivatives | |
| US4123530A (en) | N-cyclohexyl-piperazino acetamides and propionamides | |
| JP2002523499A (ja) | ピラジン化合物 | |
| EP0104614B1 (en) | Phenylpiperazine derivatives and process for producing the same | |
| KR20020019902A (ko) | 피페라진 고리 함유 화합물의 신규한 합성법 및 결정화법 | |
| US5084456A (en) | Oxazolopyridine compounds | |
| FI73677B (fi) | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3-metylflavon-8-karboxylsyraestrar. | |
| US3530137A (en) | Certain alkyl and aryl ethers and thioethers of tropine and derivatives thereof | |
| KR100382998B1 (ko) | 6-메톡시-1h-벤조트리아졸-5-카르복사미드유도체,그제조방법및그것을함유하는의약조성물 | |
| PL144860B1 (en) | Method of obtaining novel derivatives of iminothiasolidyne | |
| US4143143A (en) | Substituted imidazo[5,1-a]isoquinolines | |
| US4438121A (en) | Isoquinoline amidoxime derivatives | |
| JPS5849548B2 (ja) | ピリミジン化合物誘導体の製造法 | |
| PT617027E (pt) | Novos compostos de n-benzil-piperazina processo para a sua preparacao e as composicoes farmaceuticas que os contem | |
| DE69223422T2 (de) | Benzothiadiazinderivate | |
| KR910006987B1 (ko) | 아미노에틸 이미다졸의 제조방법 | |
| PT94928A (pt) | Processo para a preparacao de novos derivados de oxazolo-piridinas | |
| KR820001020B1 (ko) | 4-아미노 5-알킬설포닐 오르토-아니스 아미드 유도체의 제조방법 | |
| EP0081200A1 (en) | p-Oxooxazolidinylbenzene sulfonamides as antibacterial agents | |
| JPH07258251A (ja) | チザニジンの製造方法 | |
| JPS5951542B2 (ja) | ５−フエニル−チアゾリジン−４−オン誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: SOCIETE D'ETUDES SCIENTIFIQUES ET |