CA1114371A - Substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and preparation process - Google Patents
Substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and preparation processInfo
- Publication number
- CA1114371A CA1114371A CA283,994A CA283994A CA1114371A CA 1114371 A CA1114371 A CA 1114371A CA 283994 A CA283994 A CA 283994A CA 1114371 A CA1114371 A CA 1114371A
- Authority
- CA
- Canada
- Prior art keywords
- benzodioxane
- carboxamide
- methyl
- ethyl
- pyrrolidylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title claims abstract description 6
- 150000003936 benzamides Chemical class 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims description 125
- -1 nitro, amino Chemical group 0.000 claims description 65
- 239000000126 substance Substances 0.000 claims description 60
- 239000002253 acid Substances 0.000 claims description 36
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 18
- RKSFKFSIQAQPHQ-UHFFFAOYSA-N 7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=C(S(=O)(=O)NC)C=C2C(Cl)=O RKSFKFSIQAQPHQ-UHFFFAOYSA-N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 15
- AJEDNQSLTXJFJG-UHFFFAOYSA-N 7-ethylsulfonyl-2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=C(S(=O)(=O)CC)C=C2C(Cl)=O AJEDNQSLTXJFJG-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 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
- IEWVBBWTJOHHCY-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=CC=C2C(=O)Cl IEWVBBWTJOHHCY-UHFFFAOYSA-N 0.000 claims description 11
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- KHDSNFILCIVZDT-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)NC)=CC2=C1OCCO2 KHDSNFILCIVZDT-UHFFFAOYSA-N 0.000 claims description 9
- YRXDDQLZROFCKK-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-7-ethylsulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC2=C1OCCO2 YRXDDQLZROFCKK-UHFFFAOYSA-N 0.000 claims description 9
- POVZSJGKGZYZPS-UHFFFAOYSA-N n-[(1-methylpyrrolidin-2-yl)methyl]-7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(S(=O)(=O)NC)=CC=2OCCOC=2C=1C(=O)NCC1CCCN1C POVZSJGKGZYZPS-UHFFFAOYSA-N 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- SXAKAOFKGIOPHK-UHFFFAOYSA-N methyl 7-sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxylate Chemical compound O1CCOC2=C1C=C(S(N)(=O)=O)C=C2C(=O)OC SXAKAOFKGIOPHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- UAMRSLPXDICKQF-UHFFFAOYSA-N methyl 7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylate Chemical compound O1CCOC2=C1C=C(S(=O)(=O)NC)C=C2C(=O)OC UAMRSLPXDICKQF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 5
- LKYLYFSTNNVQNS-UHFFFAOYSA-N 5-amino-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2N LKYLYFSTNNVQNS-UHFFFAOYSA-N 0.000 claims description 5
- SJKOZUVHRPRMRJ-UHFFFAOYSA-N 6,7-dibromo-5-nitro-2,3-dihydro-1,4-benzodioxine-8-carbonyl chloride Chemical compound O1CCOC2=C1C(C(Cl)=O)=C(Br)C(Br)=C2[N+](=O)[O-] SJKOZUVHRPRMRJ-UHFFFAOYSA-N 0.000 claims description 5
- CJPGSUPNJOCTCY-UHFFFAOYSA-N 7-(diethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N(CC)CC)C=C2C(O)=O CJPGSUPNJOCTCY-UHFFFAOYSA-N 0.000 claims description 5
- XOPARDXSIMENIK-UHFFFAOYSA-N 7-(dimethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N(C)C)C=C2C(Cl)=O XOPARDXSIMENIK-UHFFFAOYSA-N 0.000 claims description 5
- JTKAQKREMDVCLQ-UHFFFAOYSA-N 7-(dimethylsulfamoyl)-n-[(1-methylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(S(=O)(=O)N(C)C)=CC=2OCCOC=2C=1C(=O)NCC1CCCN1C JTKAQKREMDVCLQ-UHFFFAOYSA-N 0.000 claims description 5
- NQEQVGJQJCYZNI-UHFFFAOYSA-N 7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)NC)C=C2C(O)=O NQEQVGJQJCYZNI-UHFFFAOYSA-N 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- OEYAFMGVIFWPQI-UHFFFAOYSA-N (1-benzylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1CC1=CC=CC=C1 OEYAFMGVIFWPQI-UHFFFAOYSA-N 0.000 claims description 4
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 claims description 4
- JPNWVWMCTXTDPW-UHFFFAOYSA-N 5-(4-pyrimidin-2-ylpiperazine-1-carbonyl)-2,3-dihydro-1,4-benzodioxine-7-sulfonamide Chemical compound C=1C(S(=O)(=O)N)=CC=2OCCOC=2C=1C(=O)N(CC1)CCN1C1=NC=CC=N1 JPNWVWMCTXTDPW-UHFFFAOYSA-N 0.000 claims description 4
- YIHVNRIFOBREPB-UHFFFAOYSA-N 5-acetamido-n-[(1-ethylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(NC(C)=O)C2=C1OCCO2 YIHVNRIFOBREPB-UHFFFAOYSA-N 0.000 claims description 4
- HNNTWBLCSCZYDM-UHFFFAOYSA-N 5-acetamido-n-[2-(diethylamino)ethyl]-6-nitro-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound O1CCOC2=C1C(NC(C)=O)=C([N+]([O-])=O)C=C2C(=O)NCCN(CC)CC HNNTWBLCSCZYDM-UHFFFAOYSA-N 0.000 claims description 4
- RHTLNBSAROMJMO-UHFFFAOYSA-N 5-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(Cl)=CC=C2C(=O)O RHTLNBSAROMJMO-UHFFFAOYSA-N 0.000 claims description 4
- OZXUXFWPQYLHFR-UHFFFAOYSA-N 6,7-diacetamido-n-(1-piperidin-1-ylpropyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CC(=O)NC=1C(NC(C)=O)=CC=2OCCOC=2C=1C(=O)NC(CC)N1CCCCC1 OZXUXFWPQYLHFR-UHFFFAOYSA-N 0.000 claims description 4
- HWNSSYIJNHERQA-UHFFFAOYSA-N 7-(1-adamantylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound C1C(C2)CC(C3)CC2CC13NS(=O)(=O)C(C=C1C(=O)O)=CC2=C1OCCO2 HWNSSYIJNHERQA-UHFFFAOYSA-N 0.000 claims description 4
- FSRYNXDRMYDGKD-UHFFFAOYSA-N 7-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(N)C=C2C(O)=O FSRYNXDRMYDGKD-UHFFFAOYSA-N 0.000 claims description 4
- QJHQTACTTZYGFR-UHFFFAOYSA-N 7-chloro-n-(2-piperidin-1-ylethyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(Cl)=CC=2OCCOC=2C=1C(=O)NCCN1CCCCC1 QJHQTACTTZYGFR-UHFFFAOYSA-N 0.000 claims description 4
- AVKRNLXCZBBZMD-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C([N+]([O-])=O)C=C2C(=O)O AVKRNLXCZBBZMD-UHFFFAOYSA-N 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- NVNRWKTVXWAHHF-UHFFFAOYSA-N methyl 5-methoxy-6-sulfamoyl-2,3-dihydro-1,4-benzodioxine-8-carboxylate Chemical compound O1CCOC2=C1C(OC)=C(S(N)(=O)=O)C=C2C(=O)OC NVNRWKTVXWAHHF-UHFFFAOYSA-N 0.000 claims description 4
- PNQWQELYAPSYBA-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-methoxy-6-sulfamoyl-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=C(OC)C2=C1OCCO2 PNQWQELYAPSYBA-UHFFFAOYSA-N 0.000 claims description 4
- LVYXPIJZDUZGKR-UHFFFAOYSA-N n-[(1-methylpyrrolidin-2-yl)methyl]-7-sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC2=C1OCCO2 LVYXPIJZDUZGKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- LYCFLVALOZTFDX-UHFFFAOYSA-N 5-acetamido-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2NC(=O)C LYCFLVALOZTFDX-UHFFFAOYSA-N 0.000 claims description 3
- OZGDSSXESIMADL-UHFFFAOYSA-N 5-acetamido-6-nitro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C=C([N+]([O-])=O)C(NC(=O)C)=C21 OZGDSSXESIMADL-UHFFFAOYSA-N 0.000 claims description 3
- WRIYOBWMCQYZLV-UHFFFAOYSA-N 5-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(N)C2=C1OCCO2 WRIYOBWMCQYZLV-UHFFFAOYSA-N 0.000 claims description 3
- OGNCCYFVXJBQEB-UHFFFAOYSA-N 6-chloro-n-pyrimidin-2-yl-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound ClC1=CC=C2OCCOC2=C1C(=O)NC1=NC=CC=N1 OGNCCYFVXJBQEB-UHFFFAOYSA-N 0.000 claims description 3
- AYXQAJKNYRJXCB-UHFFFAOYSA-N 7-(cyclohexylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound C=1C=2OCCOC=2C(C(=O)O)=CC=1S(=O)(=O)NC1CCCCC1 AYXQAJKNYRJXCB-UHFFFAOYSA-N 0.000 claims description 3
- ZRISRDUHJZSFSK-UHFFFAOYSA-N 7-(dimethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N(C)C)C=C2C(O)=O ZRISRDUHJZSFSK-UHFFFAOYSA-N 0.000 claims description 3
- ZHWMIKHMSOYRBC-UHFFFAOYSA-N 7-ethylsulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)CC)C=C2C(O)=O ZHWMIKHMSOYRBC-UHFFFAOYSA-N 0.000 claims description 3
- YHFLGEVINDZKFY-UHFFFAOYSA-N 7-ethylsulfonyl-n-[(1-methylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(S(=O)(=O)CC)=CC=2OCCOC=2C=1C(=O)NCC1CCCN1C YHFLGEVINDZKFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
- LKMDWVDSCXELOH-UHFFFAOYSA-N n-(1-adamantyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound O1CCOC2=C1C=CC=C2C(=O)NC1(C2)CC(C3)CC2CC3C1 LKMDWVDSCXELOH-UHFFFAOYSA-N 0.000 claims description 3
- GGKZGVHEYSZFIQ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(S(=O)(=O)NC)=CC=2OCCOC=2C=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 GGKZGVHEYSZFIQ-UHFFFAOYSA-N 0.000 claims description 3
- PZPDMRKVAIFTQT-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=CC2=C1OCCO2 PZPDMRKVAIFTQT-UHFFFAOYSA-N 0.000 claims description 3
- JYHVHIHNOSYGLA-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-methoxy-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(OC)C2=C1OCCO2 JYHVHIHNOSYGLA-UHFFFAOYSA-N 0.000 claims description 3
- LLANSHIYQPLIKH-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-7-sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC2=C1OCCO2 LLANSHIYQPLIKH-UHFFFAOYSA-N 0.000 claims description 3
- GKMVVJAITWKYHH-UHFFFAOYSA-N n-benzyl-7-(diethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C=1C(S(=O)(=O)N(CC)CC)=CC=2OCCOC=2C=1C(=O)NCC1=CC=CC=C1 GKMVVJAITWKYHH-UHFFFAOYSA-N 0.000 claims description 3
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims description 2
- DPEPZAJVZHRORQ-UHFFFAOYSA-N 1-cyclohexylpyrrolidin-3-amine Chemical compound C1C(N)CCN1C1CCCCC1 DPEPZAJVZHRORQ-UHFFFAOYSA-N 0.000 claims description 2
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 2
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 claims description 2
- OVTLDIYSXDREAM-UHFFFAOYSA-N 6,7-diacetamido-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(NC(=O)C)C(NC(C)=O)=C2C(O)=O OVTLDIYSXDREAM-UHFFFAOYSA-N 0.000 claims description 2
- OTMSVFIZWOGKOP-UHFFFAOYSA-N 6-chloro-2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=CC(Cl)=C2C(=O)Cl OTMSVFIZWOGKOP-UHFFFAOYSA-N 0.000 claims description 2
- AUIYGHHLPMMOGF-UHFFFAOYSA-N 7-(dimethylsulfamoyl)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)N(C)C)=CC2=C1OCCO2 AUIYGHHLPMMOGF-UHFFFAOYSA-N 0.000 claims description 2
- XLYXGMVNKJTUJZ-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxine-5-carbonyl chloride Chemical compound O1CCOC2=C1C=C([N+](=O)[O-])C=C2C(Cl)=O XLYXGMVNKJTUJZ-UHFFFAOYSA-N 0.000 claims description 2
- GPKDBCCYRICYKP-UHFFFAOYSA-N 7-sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N)C=C2C(O)=O GPKDBCCYRICYKP-UHFFFAOYSA-N 0.000 claims description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003805 amantadine Drugs 0.000 claims description 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 6
- ZOYXRGVJLFDPAS-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-(6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(OCCO2)C2=CC=C1[N+]([O-])=O ZOYXRGVJLFDPAS-UHFFFAOYSA-N 0.000 claims 2
- ZMANHTSNZIEHET-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-(7-nitro-2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC([N+]([O-])=O)=CC2=C1OCCO2 ZMANHTSNZIEHET-UHFFFAOYSA-N 0.000 claims 2
- BZASZJVJYDPKEC-UHFFFAOYSA-N (5-chloro-2,3-dihydro-1,4-benzodioxin-8-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(Cl)C2=C1OCCO2 BZASZJVJYDPKEC-UHFFFAOYSA-N 0.000 claims 2
- JZVGXFZJMLFILI-UHFFFAOYSA-N (6,7-dibromo-5-nitro-2,3-dihydro-1,4-benzodioxin-8-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(Br)C(Br)=C([N+]([O-])=O)C2=C1OCCO2 JZVGXFZJMLFILI-UHFFFAOYSA-N 0.000 claims 2
- OMOYDBJZBJJKGS-UHFFFAOYSA-N (6,7-dinitro-2,3-dihydro-1,4-benzodioxin-5-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(OCCO2)C2=CC([N+]([O-])=O)=C1[N+]([O-])=O OMOYDBJZBJJKGS-UHFFFAOYSA-N 0.000 claims 2
- NVAQDYFOTVEVRG-UHFFFAOYSA-N (7-amino-2,3-dihydro-1,4-benzodioxin-5-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC(N)=CC2=C1OCCO2 NVAQDYFOTVEVRG-UHFFFAOYSA-N 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- HAQXDCQBSQSHSQ-UHFFFAOYSA-N 6,7-dibromo-n-[(1-ethylpyrrolidin-2-yl)methyl]-5-nitro-2,3-dihydro-1,4-benzodioxine-8-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=C(Br)C(Br)=C([N+]([O-])=O)C2=C1OCCO2 HAQXDCQBSQSHSQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000000844 transformation Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7623835A FR2360305A1 (fr) | 1976-08-04 | 1976-08-04 | Nouveaux 2,3-alkylene bis (oxy)benzamides substitues, leurs derives et leurs procedes de preparation |
| FR7623835 | 1976-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1114371A true CA1114371A (en) | 1981-12-15 |
Family
ID=9176558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,994A Expired CA1114371A (en) | 1976-08-04 | 1977-08-03 | Substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and preparation process |
Country Status (37)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027098D0 (en) * | 1990-12-13 | 1991-02-06 | Beecham Group Plc | Pharmaceuticals |
| US10083697B2 (en) | 2015-05-27 | 2018-09-25 | Google Llc | Local persisting of data for selectively offline capable voice action in a voice-enabled electronic device |
| JP6452575B2 (ja) * | 2015-08-19 | 2019-01-16 | 株式会社トクヤマ | ミルタザピンの製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1473829A (fr) * | 1964-06-09 | 1967-03-24 | Ile De France | Nu-(tertiaire-aminoalkyl)-méthylène dioxybenzamides et leur préparation |
-
1977
- 1977-07-11 MC MC771250A patent/MC1154A1/fr unknown
- 1977-07-29 ES ES461175A patent/ES461175A1/es not_active Expired
- 1977-07-29 PT PT6686577A patent/PT66865B/pt unknown
- 1977-07-29 IN IN1165/CAL/77A patent/IN145473B/en unknown
- 1977-07-29 GR GR54066A patent/GR61351B/el unknown
- 1977-07-29 BG BG037047A patent/BG36496A3/xx unknown
- 1977-07-29 DE DE19772760414 patent/DE2760414C2/de not_active Expired - Fee Related
- 1977-08-01 OA OA56243A patent/OA05728A/xx unknown
- 1977-08-01 BE BE1008313A patent/BE857350A/xx not_active IP Right Cessation
- 1977-08-01 AU AU27507/77A patent/AU516033B2/en not_active Expired
- 1977-08-01 YU YU188277A patent/YU40005B/xx unknown
- 1977-08-02 LU LU77897A patent/LU77897A1/xx unknown
- 1977-08-02 IE IE2409/80A patent/IE45647B1/en not_active IP Right Cessation
- 1977-08-02 AT AT569677A patent/AT358034B/de not_active IP Right Cessation
- 1977-08-02 EG EG45577A patent/EG12716A/xx active
- 1977-08-02 RO RO9124577A patent/RO72963A/ro unknown
- 1977-08-02 IE IE1600/77A patent/IE45646B1/en not_active IP Right Cessation
- 1977-08-03 DK DK346977A patent/DK152366C/da not_active IP Right Cessation
- 1977-08-03 NZ NZ18481677A patent/NZ184816A/xx unknown
- 1977-08-03 CA CA283,994A patent/CA1114371A/en not_active Expired
- 1977-08-03 IL IL52644A patent/IL52644A0/xx not_active IP Right Cessation
- 1977-08-03 ZA ZA00774701A patent/ZA774701B/xx unknown
- 1977-08-03 MW MW2077A patent/MW2077A1/xx unknown
- 1977-08-03 NO NO772739A patent/NO152133C/no unknown
- 1977-08-03 SE SE7708849A patent/SE440776B/xx not_active IP Right Cessation
- 1977-08-03 NL NL7708616A patent/NL172063C/xx not_active IP Right Cessation
- 1977-08-03 HU HUSO001195 patent/HU179064B/hu not_active IP Right Cessation
- 1977-08-03 DD DD20042077A patent/DD133237A5/xx not_active IP Right Cessation
- 1977-08-03 CH CH956277A patent/CH629198A5/fr not_active IP Right Cessation
- 1977-08-04 PH PH20078A patent/PH22114A/en unknown
- 1977-08-04 CS CS775179A patent/CS216246B2/cs unknown
- 1977-08-04 PL PL1977200066A patent/PL111071B1/pl not_active IP Right Cessation
- 1977-08-04 FI FI772362A patent/FI63938C/fi not_active IP Right Cessation
- 1977-08-04 ZM ZM6077A patent/ZM6077A1/xx unknown
- 1977-08-04 SU SU772507701A patent/SU716523A3/ru active
- 1977-08-08 AR AR26867377A patent/AR219709A1/es active
-
1981
- 1981-03-25 PH PH25426-AA patent/PH18629A/en unknown
- 1981-08-07 PH PH26025A patent/PH17710A/en unknown
-
1982
- 1982-03-19 JP JP4547682A patent/JPS57167914A/ja active Granted
- 1982-06-25 IL IL66138A patent/IL66138A0/xx not_active IP Right Cessation
- 1982-09-16 HK HK404/82A patent/HK40482A/xx unknown
- 1982-09-16 HK HK403/82A patent/HK40382A/xx unknown
- 1982-11-17 SE SE8206546A patent/SE453390B/sv not_active IP Right Cessation
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| MKEX | Expiry |