CS226181B2 - Method of preparing 4-amino-5-alkylsulphonylorthoanisamide derivatives - Google Patents
Method of preparing 4-amino-5-alkylsulphonylorthoanisamide derivatives Download PDFInfo
- Publication number
- CS226181B2 CS226181B2 CS79443A CS44379A CS226181B2 CS 226181 B2 CS226181 B2 CS 226181B2 CS 79443 A CS79443 A CS 79443A CS 44379 A CS44379 A CS 44379A CS 226181 B2 CS226181 B2 CS 226181B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- acid
- ethyl
- methoxy
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 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 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 19
- 230000000794 anti-serotonin Effects 0.000 abstract description 5
- 239000003420 antiserotonin agent Substances 0.000 abstract description 5
- 230000003354 anti-apomorphinic effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 ethyl ethyl Chemical group 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 208000019695 Migraine disease Diseases 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
- 208000009079 Bronchial Spasm Diseases 0.000 description 7
- 206010027599 migraine Diseases 0.000 description 7
- 206010006482 Bronchospasm Diseases 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 230000002903 catalepsic effect Effects 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 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
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-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
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- 206010010904 Convulsion Diseases 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
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 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
- 229960004046 apomorphine Drugs 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 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 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
- 241000282472 Canis lupus familiaris Species 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940054066 benzamide antipsychotics Drugs 0.000 description 2
- 150000003936 benzamides Chemical class 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
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination 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
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- 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
- KWMLJOLKUYYJFJ-GASJEMHNSA-N (2xi)-D-gluco-heptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C(O)=O KWMLJOLKUYYJFJ-GASJEMHNSA-N 0.000 description 1
- DPZHKLJPVMYFCU-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=C(CC#N)N=C1 DPZHKLJPVMYFCU-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
- 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 1
- 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 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
- 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 1
- 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 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000003698 Heroin Dependence Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 208000036753 Schizophrenia, disorganised type Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 208000025865 Ulcer Diseases 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
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 230000003457 anti-vomiting effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000006996 mental state Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000000926 neurological effect Effects 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
- 229940127240 opiate Drugs 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000000746 purification Methods 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
- 210000000582 semen Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229950009301 stearylsulfamide Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 239000008215 water for injection Substances 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 |
|---|---|---|---|
| CS825654A CS226200B2 (cs) | 1979-01-19 | 1982-07-26 | Způsob výroby derivátů 4-amino-5-alkylsulfonylorthoanisamidů |
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226181B2 true CS226181B2 (en) | 1984-03-19 |
Family
ID=9203689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79443A CS226181B2 (en) | 1978-01-20 | 1979-01-19 | Method of preparing 4-amino-5-alkylsulphonylorthoanisamide derivatives |
Country Status (42)
| Country | Link |
|---|---|
| US (2) | US4294828A (ro) |
| JP (1) | JPS6049192B2 (ro) |
| AR (2) | AR221354A1 (ro) |
| AT (1) | AT377977B (ro) |
| AU (1) | AU528561B2 (ro) |
| BE (1) | BE872585A (ro) |
| BG (2) | BG31497A3 (ro) |
| CA (1) | CA1101430A (ro) |
| CH (1) | CH637927A5 (ro) |
| CS (1) | CS226181B2 (ro) |
| CY (1) | CY1201A (ro) |
| DD (1) | DD141520A5 (ro) |
| DE (1) | DE2901181C2 (ro) |
| DK (1) | DK158346C (ro) |
| EG (1) | EG14045A (ro) |
| ES (2) | ES476755A1 (ro) |
| FI (1) | FI71126C (ro) |
| FR (1) | FR2415099A1 (ro) |
| GB (2) | GB2083458B (ro) |
| GR (1) | GR64431B (ro) |
| HK (1) | HK12184A (ro) |
| HU (1) | HU179793B (ro) |
| IE (1) | IE47798B1 (ro) |
| IL (1) | IL56411A (ro) |
| IN (1) | IN150226B (ro) |
| IT (1) | IT1164655B (ro) |
| LU (1) | LU80786A1 (ro) |
| MC (1) | MC1232A1 (ro) |
| MX (2) | MX5793E (ro) |
| NL (1) | NL191707C (ro) |
| NO (1) | NO151320C (ro) |
| NZ (1) | NZ189378A (ro) |
| OA (1) | OA06156A (ro) |
| PH (2) | PH15725A (ro) |
| PL (2) | PL116532B1 (ro) |
| PT (1) | PT69068A (ro) |
| RO (2) | RO80311A (ro) |
| SE (2) | SE448874B (ro) |
| SU (1) | SU820659A3 (ro) |
| YU (2) | YU42172B (ro) |
| ZA (1) | ZA79219B (ro) |
| ZM (1) | ZM579A1 (ro) |
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 |
| EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| KR20060011873A (ko) * | 2003-05-16 | 2006-02-03 | 화이자 프로덕츠 인코포레이티드 | 비정형 항정신약과 ｇａｂａ 조절제, 항경련성 약물 또는 벤조다이아제핀의 치료 혼합물 |
| FR2857263B1 (fr) * | 2003-07-09 | 2005-09-09 | Sanofi Synthelabo | Nouvelle composition pharmaceutique solide comprenant de l'amisulpride |
| JP2007537232A (ja) * | 2004-05-11 | 2007-12-20 | ファイザー・プロダクツ・インク | 非定型抗精神病薬と５−ｈｔ１ｂ受容体拮抗薬の組合せ |
| AU2006239900A1 (en) * | 2005-04-22 | 2006-11-02 | Wyeth | Therapeutic combinations for the treatment or prevention of psychotic disorders |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| KR20090071598A (ko) | 2006-09-18 | 2009-07-01 | 랩터 파마슈티컬 인코포레이티드 | 수용체 결합 단백질(ｒａｐ)-접합체 투여에 의한 간 질환의 치료 |
| US7825156B2 (en) * | 2007-02-02 | 2010-11-02 | Copharms | Method of treating bipolar depression with a benzamide derivative |
| CA2727573A1 (en) * | 2008-06-25 | 2009-12-30 | Pfizer Inc. | Diaryl compounds and uses thereof |
| US20100105755A1 (en) * | 2008-09-12 | 2010-04-29 | Auspex Pharmaceuticals, Inc. | Substituted benzamide modulators of dopamine receptor |
| WO2010095940A2 (en) | 2009-02-20 | 2010-08-26 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
| TWI556839B (zh) | 2009-05-06 | 2016-11-11 | 研究室護膚股份有限公司 | 包含活性劑－磷酸鈣粒子複合物之皮膚遞送組成物及其使用方法 |
| 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 |
| 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 |
| JP6968899B2 (ja) * | 2016-11-28 | 2021-11-17 | エルビー・ファーマシューティカルズ・インコーポレイテッド | 向精神薬およびその使用 |
| 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 |
| JP7268026B2 (ja) | 2017-12-05 | 2023-05-02 | サノビオン ファーマシューティカルズ インク | 非ラセミ混合物およびその使用 |
| MX2020005517A (es) | 2017-12-05 | 2020-11-09 | Sunovion Pharmaceuticals Inc | Formas cristalinas y metodos de produccion de las mismas. |
| 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 |
| US11160758B2 (en) | 2019-06-04 | 2021-11-02 | 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 (ro) * | 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 |
| SE412908B (sv) * | 1974-12-18 | 1980-03-24 | Synthelabo | Forfarande for framstellning av terapeutiskt aktiva 2-metoxibensamider innehallande en pyrrolidin- eller en piperidinrest |
-
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 AR AR275115A patent/AR221354A1/es active
- 1979-01-10 BG BG043588A patent/BG31497A3/xx unknown
- 1979-01-10 BG BG042018A patent/BG31496A3/xx unknown
- 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 LU LU80786A patent/LU80786A1/xx unknown
- 1979-01-15 AU AU43373/79A patent/AU528561B2/en not_active Expired
- 1979-01-15 GR GR58090A patent/GR64431B/el unknown
- 1979-01-15 NZ NZ189378A patent/NZ189378A/xx unknown
- 1979-01-15 CH CH37379A patent/CH637927A5/fr active Protection Beyond IP Right Term
- 1979-01-16 MC MC791357A patent/MC1232A1/fr 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 RO RO7996297A patent/RO76393A/ro unknown
- 1979-01-17 GB GB8118999A patent/GB2083458B/en not_active Expired
- 1979-01-17 CY CY1201A patent/CY1201A/en unknown
- 1979-01-17 GB GB791690A patent/GB2012765B/en not_active Expired
- 1979-01-17 EG EG29/79A patent/EG14045A/xx active
- 1979-01-18 NO NO790180A patent/NO151320C/no unknown
- 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 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
- 1979-01-19 AT AT0039879A patent/AT377977B/de 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 OA OA56717A patent/OA06156A/xx unknown
- 1979-01-19 CS CS79443A patent/CS226181B2/cs unknown
- 1979-01-19 NL NL7900457A patent/NL191707C/xx not_active IP Right Cessation
- 1979-01-19 MX MX797669U patent/MX5793E/es unknown
- 1979-01-19 FI FI790182A patent/FI71126C/fi not_active IP Right Cessation
- 1979-01-19 CA CA319,969A patent/CA1101430A/en not_active Expired
- 1979-01-19 ZA ZA79219A patent/ZA79219B/xx unknown
- 1979-01-19 PL PL1979212899A patent/PL116532B1/pl unknown
- 1979-01-19 SU SU792714652A patent/SU820659A3/ru active
- 1979-01-19 PL PL1979224894A patent/PL118151B1/pl unknown
- 1979-01-19 MX MX7911208U patent/MX7623E/es 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 |
|---|---|---|
| CS226181B2 (en) | Method of preparing 4-amino-5-alkylsulphonylorthoanisamide derivatives | |
| SU1060112A3 (ru) | Способ получени производных 1,8-нафтиридин-3-карбоновой кислоты или их солей | |
| US4806556A (en) | Gut-selective opiates | |
| FI91401B (fi) | Menetelmä terapeuttisesti aktiivisten substituoitujen 9-aminotetrahydroakriinien ja niille läheisten yhdisteiden valmistamiseksi | |
| EP0208210B1 (en) | Pyridonecarboxylic acid derivatives and process for their preparation | |
| SK280822B6 (sk) | Imidazopyridíny, spôsob ich prípravy, farmaceutické prostriedky s ich obsahom a ich použitie | |
| PL192864B1 (pl) | Pochodna pirazyny i środek farmaceutyczny | |
| CZ285799B6 (cs) | Indolové deriváty, způsob jejich výroby, jejich použití pro výrobu farmaceutických prostředků a farmaceutické prostředky s jejich obsahem | |
| SK285165B6 (sk) | Tetrahydropyridoétery, farmaceutický prostriedok s ich obsahom a ich použitie | |
| EP0040401B1 (en) | Triazoloquinoxalin-4-ones and such oxaline-4-thiones | |
| HU220066B (hu) | Imidazo[1,2-a]piridinek alkoxi-alkil-karbamátjai, alkalmazásuk, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| JPS63295589A (ja) | 生理活性物質ｋ−２５２の誘導体 | |
| EP0892796A1 (en) | Isatin derivatives as acetylcholinesterase inhibitors and analgesics | |
| EP0326106B1 (en) | Alkylene diamines | |
| EP1003735A1 (en) | Quinolizine carboxylic acid derivatives | |
| CA1116629A (en) | Troponyl-oxamic acid derivatives and process therefor | |
| EP0383318A2 (en) | Aralkylamine compounds | |
| CN116529252B (zh) | 用于持续释放治疗剂的前药及其用途 | |
| SK281980B6 (sk) | Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie | |
| KR930003611B1 (ko) | 퀴놀론 카복실산 유도체의 제조방법 | |
| EP0550016A1 (en) | Novel quinolone carboxylic acid derivatives and processes for preparing same | |
| US3953461A (en) | Amino derivatives of thiazolo[5,4-b]pyridine-6-carboxylic acids and esters | |
| US4734414A (en) | Anti-inflammatory and anti-arthritic pyrazolo-[1,5-a]-1,3,5-triazine derivatives, compositions, and method of use therefor | |
| EP0221541A2 (en) | Quinolonecarboxylic acid derivatives and their preparation | |
| JPS63166876A (ja) | ピリドンカルボン酸誘導体 |