CA1101430A - Derivatives of 4-amino 5-alkylsulphonyl ortho- anisamides, methods of preparing them - Google Patents
Derivatives of 4-amino 5-alkylsulphonyl ortho- anisamides, methods of preparing themInfo
- Publication number
- CA1101430A CA1101430A CA319,969A CA319969A CA1101430A CA 1101430 A CA1101430 A CA 1101430A CA 319969 A CA319969 A CA 319969A CA 1101430 A CA1101430 A CA 1101430A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methoxy
- benzamide
- methyl
- ethyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 175
- 239000000126 substance Substances 0.000 claims description 25
- 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 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 229940095064 tartrate Drugs 0.000 claims description 11
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 claims description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 150000003141 primary amines Chemical class 0.000 claims 2
- UMFPWTPHSKBHSR-UHFFFAOYSA-N 2-methoxy-5-propylsulfonylbenzoic acid Chemical compound CCCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 UMFPWTPHSKBHSR-UHFFFAOYSA-N 0.000 claims 1
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 claims 1
- 239000003420 antiserotonin agent Substances 0.000 abstract description 11
- 230000000794 anti-serotonin Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 230000003354 anti-apomorphinic effect Effects 0.000 abstract description 3
- 229940054066 benzamide antipsychotics Drugs 0.000 abstract description 3
- 150000003936 benzamides Chemical class 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 229940086542 triethylamine Drugs 0.000 description 11
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 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
- 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
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- 208000019695 Migraine disease Diseases 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 208000014181 Bronchial disease 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
- 238000006243 chemical reaction Methods 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
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- 230000002903 catalepsic effect Effects 0.000 description 5
- -1 methoxymethyl ester Chemical class 0.000 description 5
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- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 230000036269 ulceration Effects 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 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
- 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 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 206010012218 Delirium Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 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 3
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- 238000010255 intramuscular injection Methods 0.000 description 3
- 239000007927 intramuscular injection Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 206010019233 Headaches Diseases 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
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- 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 2
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- 206010007776 catatonia Diseases 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000000875 corresponding effect Effects 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
- 230000007812 deficiency Effects 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- 235000013681 dietary sucrose Nutrition 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000000926 neurological 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940127240 opiate 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002582 psychostimulating effect Effects 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
- 230000001624 sedative effect Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 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 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| FR78/01632 | 1978-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101430A true CA1101430A (en) | 1981-05-19 |
Family
ID=9203689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,969A Expired CA1101430A (en) | 1978-01-20 | 1979-01-19 | Derivatives of 4-amino 5-alkylsulphonyl ortho- anisamides, methods of preparing them |
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 |
| ZA818221B (en) * | 1980-12-12 | 1982-10-27 | Beecham Group Plc | Pharmaceutical compounds |
| 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 |
| US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| US5227388A (en) * | 1989-12-26 | 1993-07-13 | 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 |
| CA2450073C (en) | 2001-07-25 | 2017-08-29 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| CA2525366A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Therapeutic combinations of atypical antipsychotics with gaba modulators, anticonvulsants or benzodiazapines |
| FR2857263B1 (fr) * | 2003-07-09 | 2005-09-09 | Sanofi Synthelabo | Nouvelle composition pharmaceutique solide comprenant de l'amisulpride |
| WO2005107808A2 (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 |
| EP2671508B1 (en) | 2005-04-28 | 2020-09-16 | Proteus Digital Health, Inc. | Pharma-informatics system |
| 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 |
| ES2919563T3 (es) | 2009-02-20 | 2022-07-27 | Enhanx Biopharm Inc | Sistema de administración de medicamentos a base de glutatión |
| KR20180114970A (ko) | 2009-05-06 | 2018-10-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| 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 |
| GB201004020D0 (en) | 2010-03-11 | 2010-04-21 | Acacia Pharma Ltd | New therapeutic use |
| AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
| EP2582665A1 (en) | 2010-06-17 | 2013-04-24 | Lupin Limited | An improved process for preparation of amisulpride |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| 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 |
| 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 |
| 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 |
| US10259786B2 (en) | 2016-11-28 | 2019-04-16 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
| US11377421B2 (en) | 2016-11-28 | 2022-07-05 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
| 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 |
| CN112236138B (zh) | 2017-12-05 | 2024-05-31 | 赛诺维信制药公司 | 晶体形式及其制备方法 |
| AU2018379992B2 (en) | 2017-12-05 | 2022-07-21 | Sunovion Pharmaceuticals Inc. | Nonracemic mixtures and uses thereof |
| 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 |
| CA3142355A1 (en) | 2019-06-04 | 2020-12-10 | Sunovion Pharmaceuticals Inc. | Modified release formulations and uses thereof |
| 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 (enExample) * | 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 BG BG043588A patent/BG31497A3/xx unknown
- 1979-01-10 AR AR275115A patent/AR221354A1/es active
- 1979-01-11 ES ES476755A patent/ES476755A1/es not_active Expired
- 1979-01-11 YU YU50/79A patent/YU42172B/xx unknown
- 1979-01-11 IN IN21/CAL/79A patent/IN150226B/en unknown
- 1979-01-11 IL IL56411A patent/IL56411A/xx unknown
- 1979-01-12 PT PT69068A patent/PT69068A/pt unknown
- 1979-01-13 DE DE2901181A patent/DE2901181C2/de not_active Expired
- 1979-01-15 CH CH37379A patent/CH637927A5/fr active Protection Beyond IP Right Term
- 1979-01-15 AU AU43373/79A patent/AU528561B2/en not_active Expired
- 1979-01-15 GR GR58090A patent/GR64431B/el unknown
- 1979-01-15 LU LU80786A patent/LU80786A1/xx unknown
- 1979-01-15 NZ NZ189378A patent/NZ189378A/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/fr unknown
- 1979-01-17 CY CY1201A patent/CY1201A/en unknown
- 1979-01-17 EG EG29/79A patent/EG14045A/xx active
- 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 US US06/004,397 patent/US4294828A/en not_active Expired - Lifetime
- 1979-01-18 DK DK020979A patent/DK158346C/da not_active IP Right Cessation
- 1979-01-18 ZM ZM5/79A patent/ZM579A1/xx unknown
- 1979-01-18 NO NO790180A patent/NO151320C/no unknown
- 1979-01-18 IT IT47706/79A patent/IT1164655B/it active Protection Beyond IP Right Term
- 1979-01-19 PL PL1979212899A patent/PL116532B1/pl unknown
- 1979-01-19 AT AT0039879A patent/AT377977B/de not_active IP Right Cessation
- 1979-01-19 PL PL1979224894A patent/PL118151B1/pl unknown
- 1979-01-19 MX MX797669U patent/MX5793E/es unknown
- 1979-01-19 ZA ZA79219A patent/ZA79219B/xx unknown
- 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 MX MX7911208U patent/MX7623E/es unknown
- 1979-01-19 SU SU792714652A patent/SU820659A3/ru active
- 1979-01-19 JP JP54005483A patent/JPS6049192B2/ja not_active Expired
- 1979-01-19 HU HU79SO1241A patent/HU179793B/hu unknown
- 1979-01-19 CA CA319,969A patent/CA1101430A/en not_active Expired
- 1979-01-19 FI FI790182A patent/FI71126C/fi not_active IP Right Cessation
- 1979-01-19 CS CS79443A patent/CS226181B2/cs 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
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