CA2317536A1 - Derives aminosulphonylbenzamides utilises comme inhibiteurs de l'activite des canaux calcium neuronaux - Google Patents
Derives aminosulphonylbenzamides utilises comme inhibiteurs de l'activite des canaux calcium neuronaux Download PDFInfo
- Publication number
- CA2317536A1 CA2317536A1 CA002317536A CA2317536A CA2317536A1 CA 2317536 A1 CA2317536 A1 CA 2317536A1 CA 002317536 A CA002317536 A CA 002317536A CA 2317536 A CA2317536 A CA 2317536A CA 2317536 A1 CA2317536 A1 CA 2317536A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cycloalkyl
- benzamide
- optionally substituted
- substituted phenyl
- 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.)
- Abandoned
Links
- 108090000312 Calcium Channels Proteins 0.000 title description 7
- 102000003922 Calcium Channels Human genes 0.000 title description 7
- 230000000694 effects Effects 0.000 title description 4
- 230000001537 neural effect Effects 0.000 title description 3
- MXBLZLWZAHUKLU-UHFFFAOYSA-N 2-sulfamoylbenzamide Chemical class NC(=O)C1=CC=CC=C1S(N)(=O)=O MXBLZLWZAHUKLU-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 15
- -1 ethoxy, hydroxy Chemical group 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 229940032147 starch Drugs 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 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 5
- 239000002775 capsule Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- DKUCEJPVQLWIEU-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(2-methylpropyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(=O)NCC(C)C)C=C1 DKUCEJPVQLWIEU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940080313 sodium starch Drugs 0.000 description 4
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- DGBGDPLUHZTVRK-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(2-phenylethyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCCC1=CC=CC=C1 DGBGDPLUHZTVRK-UHFFFAOYSA-N 0.000 description 2
- XTXFOEDETNAJPF-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(3-methoxypropyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(=O)NCCCOC)C=C1 XTXFOEDETNAJPF-UHFFFAOYSA-N 0.000 description 2
- CJCGXTRNWLLSBD-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(4-phenylbutyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCCCCC1=CC=CC=C1 CJCGXTRNWLLSBD-UHFFFAOYSA-N 0.000 description 2
- PTCSSXYPZOFISK-UHFFFAOYSA-N 4-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 PTCSSXYPZOFISK-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- SNSNLYSCMWMQKR-UHFFFAOYSA-N N-cyclohexyl-4-(dipropylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NC1CCCCC1 SNSNLYSCMWMQKR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RKVGNQZTRREOLW-UHFFFAOYSA-N n,n-dibenzyl-4-(dipropylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 RKVGNQZTRREOLW-UHFFFAOYSA-N 0.000 description 2
- VYLYNQOMRQAPRU-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-(dipropylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCC1CCCCC1 VYLYNQOMRQAPRU-UHFFFAOYSA-N 0.000 description 2
- NZGZAIACRAIROG-UHFFFAOYSA-N n-butyl-4-(dipropylsulfamoyl)benzamide Chemical compound CCCCNC(=O)C1=CC=C(S(=O)(=O)N(CCC)CCC)C=C1 NZGZAIACRAIROG-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002217 thermospray mass spectrum Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QLGCEPOKCBTPKF-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-(3,3-dimethylpiperidin-1-yl)sulfonyl-n-(3-methylbutyl)-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzamide Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC(S(=O)(=O)N2CC(C)(C)CCC2)=CC=1C(=O)N(CCC(C)C)CCC1CCCN1C QLGCEPOKCBTPKF-BTJKTKAUSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical class 0.000 description 1
- JJUDNORYWPPBJQ-UHFFFAOYSA-N 3-(dipropylsulfamoyl)-n-[(4-fluorophenyl)methyl]benzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC(F)=CC=2)=C1 JJUDNORYWPPBJQ-UHFFFAOYSA-N 0.000 description 1
- LEIVRKLEPFCHRE-UHFFFAOYSA-N 3-(dipropylsulfamoyl)-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC(OC)=CC=2)=C1 LEIVRKLEPFCHRE-UHFFFAOYSA-N 0.000 description 1
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 1
- IXAXZGIVNXKGDZ-UHFFFAOYSA-N 4-(3-ethylpiperidin-1-yl)sulfonyl-N-(3-methylbutyl)-N-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CCC1CCCN(C1)S(=O)(=O)c1ccc(cc1)C(=O)N(CCC(C)C)CCN1CCCC1 IXAXZGIVNXKGDZ-UHFFFAOYSA-N 0.000 description 1
- AYFHAJOALAFRMH-UHFFFAOYSA-N 4-(dibutylsulfamoyl)-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound C1=CC(S(=O)(=O)N(CCCC)CCCC)=CC=C1C(=O)NCC1=CC=C(OC)C=C1 AYFHAJOALAFRMH-UHFFFAOYSA-N 0.000 description 1
- LBZUDJLOULQTMN-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(3-methylbutyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(=O)NCCC(C)C)C=C1 LBZUDJLOULQTMN-UHFFFAOYSA-N 0.000 description 1
- WVYAPIHPHRAGGW-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-(3-phenylpropyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCCCC1=CC=CC=C1 WVYAPIHPHRAGGW-UHFFFAOYSA-N 0.000 description 1
- XMUASFRLKLXOQM-UHFFFAOYSA-N 4-(dipropylsulfamoyl)-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCC1=CC=C(OC)C=C1 XMUASFRLKLXOQM-UHFFFAOYSA-N 0.000 description 1
- LCQXGFTXKWEWQC-UHFFFAOYSA-N 4-(dipropylsulfamoyl)benzoyl chloride Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 LCQXGFTXKWEWQC-UHFFFAOYSA-N 0.000 description 1
- NSQNDIVTMCBIAS-UHFFFAOYSA-N 4-[butyl(phenyl)sulfamoyl]-n-[(4-fluorophenyl)methyl]benzamide Chemical compound C=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCCC)C1=CC=CC=C1 NSQNDIVTMCBIAS-UHFFFAOYSA-N 0.000 description 1
- JTAVMRXIPJWYSO-UHFFFAOYSA-N 4-[butyl(phenyl)sulfamoyl]-n-hexylbenzamide Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1S(=O)(=O)N(CCCC)C1=CC=CC=C1 JTAVMRXIPJWYSO-UHFFFAOYSA-N 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- XNTLKCMKAGFJTN-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.CN(CCN(C(C1=CC(=CC=C1)S(=O)(=O)N1CC(CCC1)(C)C)=O)CC1=CC=C(C=C1)F)C Chemical compound C(C=C/C(=O)O)(=O)O.CN(CCN(C(C1=CC(=CC=C1)S(=O)(=O)N1CC(CCC1)(C)C)=O)CC1=CC=C(C=C1)F)C XNTLKCMKAGFJTN-UHFFFAOYSA-N 0.000 description 1
- NSRJBLIXJYWQEL-UHFFFAOYSA-N C(CC)N(S(=O)(=O)C1=CC=C(C(=O)NCC2=CC(=CC=C2)Cl)C=C1)CCC Chemical compound C(CC)N(S(=O)(=O)C1=CC=C(C(=O)NCC2=CC(=CC=C2)Cl)C=C1)CCC NSRJBLIXJYWQEL-UHFFFAOYSA-N 0.000 description 1
- MCZLHPMJRKPLFI-UHFFFAOYSA-N C(CC)N(S(=O)(=O)C1=CC=C(C(=O)NCCCCCC)C=C1)CCC Chemical compound C(CC)N(S(=O)(=O)C1=CC=C(C(=O)NCCCCCC)C=C1)CCC MCZLHPMJRKPLFI-UHFFFAOYSA-N 0.000 description 1
- ZARWAZSBVQKEHT-UHFFFAOYSA-N CCCCCNC(=O)c1ccc(cc1)S(=O)(=O)N(CCC)CCC Chemical compound CCCCCNC(=O)c1ccc(cc1)S(=O)(=O)N(CCC)CCC ZARWAZSBVQKEHT-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 208000001408 Carbon monoxide poisoning Diseases 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XBUNQZHYWYNBNA-UHFFFAOYSA-N Cl.CC(C)CCN(CCN1CCCC1)C(=O)c1cccc(c1)S(=O)(=O)N1CCCC(C)(C)C1 Chemical compound Cl.CC(C)CCN(CCN1CCCC1)C(=O)c1cccc(c1)S(=O)(=O)N1CCCC(C)(C)C1 XBUNQZHYWYNBNA-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 206010028424 Myasthenic syndrome Diseases 0.000 description 1
- LMVIMQXUEQTVAP-UHFFFAOYSA-N N-[(4-chlorophenyl)methyl]-4-(dipropylsulfamoyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(=O)NCc1ccc(Cl)cc1 LMVIMQXUEQTVAP-UHFFFAOYSA-N 0.000 description 1
- RSIIYNGQQMPLNT-UHFFFAOYSA-N N-[2-(2-chlorophenyl)ethyl]-4-(dipropylsulfamoyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(=O)NCCc1ccccc1Cl RSIIYNGQQMPLNT-UHFFFAOYSA-N 0.000 description 1
- LUBKYMQMXLFJFV-UHFFFAOYSA-N N-[2-(4-methoxyphenyl)ethyl]-3-(3-methylpiperidin-1-yl)sulfonyl-N-(2-piperidin-1-ylethyl)benzamide Chemical compound N1(CCCCC1)CCN(C(C1=CC(=CC=C1)S(=O)(=O)N1CC(CCC1)C)=O)CCC1=CC=C(C=C1)OC LUBKYMQMXLFJFV-UHFFFAOYSA-N 0.000 description 1
- BDNPADUWOGKTFP-UHFFFAOYSA-N N-cyclopentyl-4-(dipropylsulfamoyl)benzamide Chemical compound CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(=O)NC1CCCC1 BDNPADUWOGKTFP-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000020339 Spinal injury Diseases 0.000 description 1
- 208000006011 Stroke 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
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 208000029039 cyanide poisoning Diseases 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 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
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QDXDTEBWRNKSEC-UHFFFAOYSA-N n-(cyclohexylmethyl)-3-(3,3-dimethylpiperidin-1-yl)sulfonyl-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound C1C(C)(C)CCCN1S(=O)(=O)C1=CC=CC(C(=O)N(CCCN2CCCC2)CC2CCCCC2)=C1 QDXDTEBWRNKSEC-UHFFFAOYSA-N 0.000 description 1
- TZZKBRWPXGPLSM-UHFFFAOYSA-N n-(cyclohexylmethyl)-n-[2-(dimethylamino)ethyl]-3-(3,3-dimethylpiperidin-1-yl)sulfonylbenzamide Chemical compound C=1C=CC(S(=O)(=O)N2CC(C)(C)CCC2)=CC=1C(=O)N(CCN(C)C)CC1CCCCC1 TZZKBRWPXGPLSM-UHFFFAOYSA-N 0.000 description 1
- AIBKTKSUGRSTSF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[phenyl(propyl)sulfamoyl]benzamide Chemical compound C=1C=CC(C(=O)NCC=2C=CC(F)=CC=2)=CC=1S(=O)(=O)N(CCC)C1=CC=CC=C1 AIBKTKSUGRSTSF-UHFFFAOYSA-N 0.000 description 1
- KCFRJCDJAZHUEH-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-[phenyl(propyl)sulfamoyl]benzamide Chemical compound C=1C=C(C(=O)NCC=2C=CC(OC)=CC=2)C=CC=1S(=O)(=O)N(CCC)C1=CC=CC=C1 KCFRJCDJAZHUEH-UHFFFAOYSA-N 0.000 description 1
- VFRZRVNHBUIVIW-UHFFFAOYSA-N n-benzyl-4-(dipropylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C(=O)NCC1=CC=CC=C1 VFRZRVNHBUIVIW-UHFFFAOYSA-N 0.000 description 1
- VETGYUMUFWSSDQ-UHFFFAOYSA-N n-hexyl-4-[phenyl(propyl)sulfamoyl]benzamide Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1S(=O)(=O)N(CCC)C1=CC=CC=C1 VETGYUMUFWSSDQ-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention se rapporte à un composé pharmaceutique représenté par la formule (I) dans laquelle le groupe aminosulfonyle est attaché en position 3 ou 4 et où R?1¿ est hydrogène, alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿10?, cycloalkyle C¿3?-C¿10?-alkyle C¿1?-C¿4? ou phényle-alkyle C¿1?-C¿4?, R?2¿ est alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿10?, cycloalkyle C¿3?-C¿10?-alkyle C¿1?-C¿4? ou phényle-alkyle C¿1?-C¿4? ou (CH¿2?)¿2?NR?5¿R?6¿ où R?5¿ et R?6¿ sont chacun hydrogène ou alkyle C¿1?-C¿6?, et R?3¿ et R?4¿ sont chacun alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿10?, cycloalkyle C¿3?-C¿10?-alkyle C¿1?-C¿4?, alcényle C¿3?-C¿6?, phényle éventuellement substitué ou phényle-alkyle C¿1?-C¿4? éventuellement substitué, ou bien R?1¿ et R?2¿, ou R?3¿ et R?4¿, ou R?5¿ et R?6¿ forment conjointement à l'atome d'azote auquel ils sont attachés, un groupe carbocyclique contenant 4 à 7 atomes de carbone éventuellement substitués par un à trois groupes méthyle ou éthyle et contenant éventuellement un atome d'oxygène ou un autre atome d'azote, ledit groupe carbocyclique étant éventuellement fusionné à un groupe phényle éventuellement substitué. L'invention se rapporte également à un sel de ce composé.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9800750.3 | 1998-01-14 | ||
| GBGB9800750.3A GB9800750D0 (en) | 1998-01-14 | 1998-01-14 | Pharmaceutical compound |
| PCT/GB1999/000099 WO1999036398A1 (fr) | 1998-01-14 | 1999-01-13 | Derives aminosulphonylbenzamides utilises comme inhibiteurs de l'activite des canaux calcium neuronaux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2317536A1 true CA2317536A1 (fr) | 1999-07-22 |
Family
ID=10825269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002317536A Abandoned CA2317536A1 (fr) | 1998-01-14 | 1999-01-13 | Derives aminosulphonylbenzamides utilises comme inhibiteurs de l'activite des canaux calcium neuronaux |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1047670A1 (fr) |
| JP (1) | JP2002509135A (fr) |
| AU (1) | AU2172899A (fr) |
| CA (1) | CA2317536A1 (fr) |
| GB (1) | GB9800750D0 (fr) |
| WO (1) | WO1999036398A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2812198B1 (fr) * | 2000-07-28 | 2008-07-18 | Sod Conseils Rech Applic | DERIVES D'AMIDINES INHIBITEURS DE PHOSPHATASES cdc25 |
| CA2461603A1 (fr) * | 2001-09-24 | 2003-04-03 | Elan Pharmaceuticals, Inc. | Amines substituees pour le traitement de la maladie d'alzheimer |
| TW200302717A (en) * | 2002-02-06 | 2003-08-16 | Schering Corp | Novel gamma secretase inhibitors |
| EP1581472A2 (fr) | 2002-12-20 | 2005-10-05 | MIGENIX Corp. | Ligands d'adenine nucleotide translocase (ant) et compositions et methodes associees |
| AU2006254809B2 (en) * | 2005-06-09 | 2012-03-15 | Vertex Pharmaceuticals Incorporated | Indane derivatives as modulators of ion channels |
| JP5361857B2 (ja) * | 2007-03-23 | 2013-12-04 | ファイザー・リミテッド | イオンチャネルの阻害剤 |
| GB201007791D0 (en) * | 2010-05-10 | 2010-06-23 | Glaxo Group Ltd | Novel compounds |
| GB201007789D0 (en) * | 2010-05-10 | 2010-06-23 | Glaxo Group Ltd | Novel Compound |
| US9399619B2 (en) | 2011-07-01 | 2016-07-26 | Baruch S. Blumberg Institute | Sulfamoylbenzamide derivatives as antiviral agents against HBV infection |
| WO2019139869A1 (fr) | 2018-01-10 | 2019-07-18 | Cura Therapeutics Llc | Compositions pharmaceutiques comprenant des phénylsulfonamides, et leurs applications thérapeutiques |
| AU2020310190A1 (en) * | 2019-07-11 | 2022-02-24 | Cura Therapeutics, Llc | Phenyl compounds and pharmaceutical compositions thereof, and their therapeutic applications |
| EP4172149A4 (fr) | 2020-06-29 | 2024-09-04 | Bacainn Biotherapeutics, Ltd. | Composés de probénécide pour le traitement d'une maladie pulmonaire à médiation par inflammasomes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE147375T1 (de) * | 1992-09-22 | 1997-01-15 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, sowie ihre verwendung als antiarrhythmika |
-
1998
- 1998-01-14 GB GBGB9800750.3A patent/GB9800750D0/en not_active Ceased
-
1999
- 1999-01-13 JP JP2000540115A patent/JP2002509135A/ja active Pending
- 1999-01-13 WO PCT/GB1999/000099 patent/WO1999036398A1/fr not_active Ceased
- 1999-01-13 AU AU21728/99A patent/AU2172899A/en not_active Abandoned
- 1999-01-13 CA CA002317536A patent/CA2317536A1/fr not_active Abandoned
- 1999-01-13 EP EP99901722A patent/EP1047670A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999036398A1 (fr) | 1999-07-22 |
| EP1047670A1 (fr) | 2000-11-02 |
| GB9800750D0 (en) | 1998-03-11 |
| AU2172899A (en) | 1999-08-02 |
| JP2002509135A (ja) | 2002-03-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0158775B1 (fr) | Sulfonamidobenzamides substitués, agents anti-arythmiques et leurs compositions | |
| US6143769A (en) | Phenylacetic acid benzylamides | |
| CA1235122A (fr) | Derives de substitution de trans-1,2- diaminocyclohexanamide | |
| CA2606262C (fr) | Nouveaux ligands recepteurs histaminiques h3 et leurs applications therapeutiques | |
| SK82298A3 (en) | Novel compounds with analgesic effect | |
| WO1997029097A1 (fr) | Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht¿7? | |
| CA2317536A1 (fr) | Derives aminosulphonylbenzamides utilises comme inhibiteurs de l'activite des canaux calcium neuronaux | |
| CN101605767A (zh) | 制备哌嗪基苯甲酰胺衍生物和二氮杂环庚烷基苯甲酰胺衍生物的方法 | |
| US5302720A (en) | Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents | |
| WO2004013100A2 (fr) | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique | |
| HU221315B1 (en) | Alkyl-substituted piperazine derivatives, pharmaceutical compositions containing them, and process for producing them | |
| WO1995029152A1 (fr) | Derives de benzamide utilises comme antagonistes de la vasopressine | |
| EP0290377B1 (fr) | [1H-Imidazolyl-1]-4 benzamides substitués en tant qu'agents antiarythmiques | |
| HU208111B (en) | Process for producing phenol derivatives and pharmaceutical compositions comprising such compounds | |
| KR20010070997A (ko) | 비페닐 유도체 | |
| GB2352240A (en) | Novel sulphonamides useful in treating CNS disorders | |
| EP0324791B1 (fr) | Aryl-n-aminoalkyl-4-(sulfonamido)benzamides, agents antiarhytmiques et leurs compositions | |
| CA2244940A1 (fr) | Nouvelles piperidines derivees de la 1-/(piperazin-1-yl-)aryl(oxy/amino)carbonyl/-4-aryl-piperidine comme antagonistes selectifs des recepteurs 5-ht-1d.beta | |
| FR2740134A1 (fr) | Derives d'amines cycliques d'aryl-piperazines, leur preparation et les compositions pharmaceutiques les contenant | |
| US20080261949A1 (en) | Cyclohexyl(alkyl)propanolamines, preparation method and pharmaceutical compositions containing same | |
| WO1998031669A1 (fr) | Nouvelles arylpiperazines derivees de piperidine comme medicaments antidepresseurs | |
| KR20040007672A (ko) | 신규한 페닐알킬디아민 및 아미드 유사체 | |
| JP3845452B2 (ja) | α１―交感神経受容体拮抗薬 | |
| NO338104B1 (no) | Tetrahydroisoquinolin-sulfonamid-derivater, farmasøytiske preparater inneholdende slike og anvendelse derav som terapeutisk middel | |
| US5202351A (en) | 1-phenylalkyl-3-phenylurea derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |