CH627162A5 - - Google Patents
Download PDFInfo
- Publication number
- CH627162A5 CH627162A5 CH867977A CH867977A CH627162A5 CH 627162 A5 CH627162 A5 CH 627162A5 CH 867977 A CH867977 A CH 867977A CH 867977 A CH867977 A CH 867977A CH 627162 A5 CH627162 A5 CH 627162A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- allyl
- formula
- dimethoxy
- och
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 17
- 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 12
- 239000002253 acid Substances 0.000 claims description 9
- -1 benzamide quaternary ammonium salt Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- YEVQOPOKMKTXMD-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(O)=O)=C1OC YEVQOPOKMKTXMD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 2
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical class C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- 150000007928 imidazolide derivatives Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000011282 treatment Methods 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 206010060800 Hot flush Diseases 0.000 description 20
- OFCFLGYUMQEVGO-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(N)=O)=C1OC OFCFLGYUMQEVGO-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 208000035475 disorder Diseases 0.000 description 13
- 208000033830 Hot Flashes Diseases 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 231100000957 no side effect Toxicity 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 206010022998 Irritability Diseases 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- 230000009245 menopause Effects 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 4
- 208000019695 Migraine disease Diseases 0.000 description 4
- 230000002903 catalepsic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 210000004243 sweat Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000003251 Pruritus Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- LLPQAUJOSNFUSU-UHFFFAOYSA-N methyl 2,3-dimethoxy-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=CC(OC)=C1OC LLPQAUJOSNFUSU-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229960003387 progesterone Drugs 0.000 description 3
- 239000000186 progesterone Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 206010003439 Artificial menopause Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000009802 hysterectomy Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 201000010260 leiomyoma Diseases 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TZOCBFJIISELCS-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(Cl)=O)=C1OC TZOCBFJIISELCS-UHFFFAOYSA-N 0.000 description 1
- MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-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
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 208000001287 Galactorrhea Diseases 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010027295 Menometrorrhagia Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000029082 Pelvic Inflammatory Disease Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010049677 Salpingo-oophoritis Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 206010041349 Somnolence 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
- 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 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 210000000481 breast Anatomy 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
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 208000027744 congestion Diseases 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000027046 diestrus Effects 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000003687 estradiol congener Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 206010016766 flatulence Diseases 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QRNDDJXJUHBGSG-UHFFFAOYSA-N methoxyethyne Chemical compound COC#C QRNDDJXJUHBGSG-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-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
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 208000013464 vaginal disease Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 208000016254 weariness Diseases 0.000 description 1
- 239000008096 xylene 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7622180A FR2358892A1 (fr) | 1976-07-19 | 1976-07-19 | N(1'-allyl 2'-pyrrolidylmethyl)2,3-dimethoxy 5-sulfamoyl benzamide, ses derives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627162A5 true CH627162A5 (en, 2012) | 1981-12-31 |
Family
ID=9175947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH867977A CH627162A5 (en, 2012) | 1976-07-19 | 1977-07-13 |
Country Status (38)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438650A1 (fr) * | 1978-10-11 | 1980-05-09 | Ile De France | N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, leurs methodes de preparation et leur application dans le traitement des troubles du bas appareil urinaire |
| JPS5639431A (en) * | 1979-09-06 | 1981-04-15 | Susumu Yagyu | Colorimeter having two-light pass length and two-wave length |
| FR2478093A1 (fr) * | 1980-03-12 | 1981-09-18 | Ile De France | Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) |
| 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 |
| FR2584605B1 (fr) * | 1985-07-15 | 1988-06-17 | Ile De France | Application du n-(1-allyl-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide dans le traitement de la maladie de parkinson |
| US7645750B2 (en) * | 2006-12-13 | 2010-01-12 | Yung Shin Pharmaceutical Ind. Co., Ltd. | Method of treating symptoms of hormonal variations |
| US8420624B2 (en) * | 2007-12-04 | 2013-04-16 | Yung Shin Pharm. Ind. Co., Ltd. | Methods for treating or preventing symptoms of hormonal variations |
| CN105481733A (zh) * | 2015-12-30 | 2016-04-13 | 苏州诚和医药化学有限公司 | 一种一步法合成2-甲氧基-5-氨磺酰基苯甲酸甲酯的方法 |
-
1976
- 1976-07-19 FR FR7622180A patent/FR2358892A1/fr active Granted
-
1977
- 1977-05-24 CY CY1036A patent/CY1036A/xx unknown
- 1977-05-24 GB GB21883/77A patent/GB1539319A/en not_active Expired
- 1977-06-30 BE BE1008238A patent/BE856289A/xx not_active IP Right Cessation
- 1977-07-05 MC MC771249A patent/MC1153A1/xx unknown
- 1977-07-05 OA OA56219A patent/OA05704A/xx unknown
- 1977-07-08 PH PH19975A patent/PH12838A/en unknown
- 1977-07-08 ZM ZM54/77A patent/ZM5477A1/xx unknown
- 1977-07-11 AR AR268387A patent/AR214330A1/es active
- 1977-07-11 EG EG413/77A patent/EG12911A/xx active
- 1977-07-11 ES ES460621A patent/ES460621A1/es not_active Expired
- 1977-07-12 GR GR53944A patent/GR60836B/el unknown
- 1977-07-13 CH CH867977A patent/CH627162A5/fr not_active IP Right Cessation
- 1977-07-13 YU YU1739/77A patent/YU40677B/xx unknown
- 1977-07-13 NZ NZ184634A patent/NZ184634A/xx unknown
- 1977-07-14 AU AU27026/77A patent/AU509291B2/en not_active Expired
- 1977-07-14 SE SE7708176A patent/SE425243B/xx not_active IP Right Cessation
- 1977-07-15 HU HU77SO1193A patent/HU174981B/hu unknown
- 1977-07-15 DD DD7700200091A patent/DD132492A5/xx not_active IP Right Cessation
- 1977-07-15 IE IE1482/77A patent/IE46171B1/en not_active IP Right Cessation
- 1977-07-15 MX MX775905U patent/MX4711E/es unknown
- 1977-07-15 NO NO772530A patent/NO146598C/no unknown
- 1977-07-15 PT PT66819A patent/PT66819B/pt unknown
- 1977-07-15 AT AT0511677A patent/AT365570B/de not_active IP Right Cessation
- 1977-07-15 LU LU77782A patent/LU77782A1/xx unknown
- 1977-07-15 DD DD77207969A patent/DD137670A5/xx not_active IP Right Cessation
- 1977-07-15 JP JP8552977A patent/JPS5338631A/ja active Granted
- 1977-07-18 IL IL52547A patent/IL52547A/xx unknown
- 1977-07-18 DK DK326377A patent/DK156646C/da not_active IP Right Cessation
- 1977-07-18 PL PL1977199723A patent/PL104244B1/pl unknown
- 1977-07-18 NL NLAANVRAGE7707982,A patent/NL174347C/xx not_active IP Right Cessation
- 1977-07-18 FI FI772214A patent/FI67213C/fi not_active IP Right Cessation
- 1977-07-19 RO RO7791091A patent/RO71691A/ro unknown
- 1977-07-19 SU SU772504152A patent/SU695556A3/ru active
- 1977-07-19 CS CS774811A patent/CS219885B2/cs unknown
- 1977-08-23 IN IN1318/CAL/77A patent/IN146993B/en unknown
-
1978
- 1978-05-12 ZA ZA00774256A patent/ZA774256B/xx unknown
-
1980
- 1980-04-03 HK HK178/80A patent/HK17880A/xx unknown
-
1983
- 1983-10-13 US US06/540,918 patent/US4499019A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH628344A5 (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. | |
| EP0040573B1 (fr) | Dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique substitués en 2, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires nouveaux obtenus | |
| CH639369A5 (fr) | Benzamides heterocycliques substitues et leurs procedes de preparation. | |
| CA1097647A (fr) | Procede de preparation de nouvelles imidazoquinoleines et de leurs sels | |
| CH627162A5 (en, 2012) | ||
| CH649994A5 (fr) | Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant. | |
| CA1131230A (fr) | Procede de preparation de nouveaux derives de 1,3-dihydro3-/1-/2-(2,3-dihydro 1,4-benzodioxin-2-yl) 2-hydroxy-ethyl/piperidin-4-yl/2h-indol-2-one | |
| EP0024960B1 (fr) | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux | |
| LU81565A1 (fr) | Nouvelles imidazoquinoxalines et leurs sels,leur procede de preparation,leur application a titre de medicaments et les compositions pharmaceutiques les renfermant | |
| FR1877M (en, 2012) | ||
| CA1139763A (fr) | Procede d'obtention de nouveaux aryltrifluoroethanols | |
| CA1128946A (fr) | Procede de preparation de derives du piperidyl-indole | |
| CH631157A5 (fr) | Derives d'acide benzoique, leur procede de preparation et leur application therapeutique. | |
| FR2625502A1 (fr) | Nouveaux derives du 3-piperidine carbaldehyde oxime, leur procede de preparation et leur application comme medicaments | |
| CA1298301C (fr) | Benzamides, leur procede d'obtention et leurs applications therapeutiques | |
| LU84429A1 (fr) | A titre de medicaments,certains derives de l'acide 4-phenyl 4-oxo 2-butenoique et compositions les renfermant | |
| KR840002063B1 (ko) | N-(1-알릴-2-피롤리디닐-메틸)2-메톡시-4-아미노-5-메틸설파모일 벤즈아미드의 제조방법 | |
| EP0384843A2 (fr) | Dérivés de la 1-arylsulfonyl 2-pipéridinone, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| CA1098524A (fr) | Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique | |
| EP0335758A2 (fr) | Dérivés de la 1-arylsulfonyl 2-pyrrolidinone, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant | |
| CA1060020A (fr) | Procede de preparation de nouveaux derives de la dibenzo/b,c/ thiepine et leurs sels | |
| EP0176444A1 (fr) | Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant | |
| CH641775A5 (fr) | N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, son procede de preparation et composition le renferment. | |
| CH667873A5 (fr) | Derive de n-imidazolidinylmethyl benzamide. | |
| US4172145A (en) | Benzo(b)furylacetic acid derivatives to reduce inflammation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |