CS216246B2 - Method of making the substituted 2,3-alkylen-bis-+l oxy+pbenzamides - Google Patents
Method of making the substituted 2,3-alkylen-bis-+l oxy+pbenzamides Download PDFInfo
- Publication number
- CS216246B2 CS216246B2 CS775179A CS517977A CS216246B2 CS 216246 B2 CS216246 B2 CS 216246B2 CS 775179 A CS775179 A CS 775179A CS 517977 A CS517977 A CS 517977A CS 216246 B2 CS216246 B2 CS 216246B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzodioxane
- alkyl
- added
- carboxylic acid
- filtered
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cycloalkenylalkyl Chemical group 0.000 claims abstract description 91
- 239000002253 acid Substances 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000002081 enamines Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 claims 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 230000002903 catalepsic effect Effects 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- VCLSWKVAHAJSFL-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=CC=C2C(=O)O VCLSWKVAHAJSFL-UHFFFAOYSA-N 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
- 230000003474 anti-emetic effect Effects 0.000 abstract description 3
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 230000000949 anxiolytic effect Effects 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 2
- 125000003441 thioacyl group Chemical group 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 abstract 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 152
- 239000000203 mixture Substances 0.000 description 129
- 239000000243 solution Substances 0.000 description 121
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 96
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
- 239000002244 precipitate Substances 0.000 description 52
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 239000013078 crystal Substances 0.000 description 46
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 26
- 238000002844 melting Methods 0.000 description 23
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000003610 charcoal Substances 0.000 description 17
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 229920002472 Starch Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000008107 starch Substances 0.000 description 10
- 235000019698 starch Nutrition 0.000 description 10
- NCSFGFOXYGSSSH-UHFFFAOYSA-N 7-chlorosulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(Cl)(=O)=O)C=C2C(=O)O NCSFGFOXYGSSSH-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 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 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 229920000609 methyl cellulose Polymers 0.000 description 8
- 239000001923 methylcellulose Substances 0.000 description 8
- 235000010981 methylcellulose Nutrition 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 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 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 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 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 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 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 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PWJRPWPPVFPUQD-UHFFFAOYSA-N 5-methoxy-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2OC PWJRPWPPVFPUQD-UHFFFAOYSA-N 0.000 description 4
- 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 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 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 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 description 4
- 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 description 4
- 231100000957 no side effect Toxicity 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 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 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 description 3
- 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 description 3
- 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 description 3
- QFTQYWNNATXJGG-UHFFFAOYSA-N 6-chlorosulfonyl-5-methoxy-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C=C(S(Cl)(=O)=O)C(OC)=C21 QFTQYWNNATXJGG-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
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- C07D487/04—Ortho-condensed systems
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Endocrinology (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216246B2 true CS216246B2 (en) | 1982-10-29 |
Family
ID=9176558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS775179A CS216246B2 (en) | 1976-08-04 | 1977-08-04 | Method of making the substituted 2,3-alkylen-bis-+l oxy+pbenzamides |
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/xx unknown
- 1977-07-29 PT PT6686577A patent/PT66865B/pt unknown
- 1977-07-29 GR GR54066A patent/GR61351B/el unknown
- 1977-07-29 BG BG037047A patent/BG36496A3/xx unknown
- 1977-07-29 IN IN1165/CAL/77A patent/IN145473B/en unknown
- 1977-07-29 DE DE19772760414 patent/DE2760414C2/de not_active Expired - Fee Related
- 1977-07-29 ES ES461175A patent/ES461175A1/es not_active Expired
- 1977-08-01 YU YU188277A patent/YU40005B/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 OA OA56243A patent/OA05728A/xx unknown
- 1977-08-02 AT AT569677A patent/AT358034B/de not_active IP Right Cessation
- 1977-08-02 IE IE2409/80A patent/IE45647B1/en not_active IP Right Cessation
- 1977-08-02 EG EG45577A patent/EG12716A/xx active
- 1977-08-02 IE IE1600/77A patent/IE45646B1/en not_active IP Right Cessation
- 1977-08-02 RO RO9124577A patent/RO72963A/ro unknown
- 1977-08-02 LU LU77897A patent/LU77897A1/xx unknown
- 1977-08-03 HU HUSO001195 patent/HU179064B/hu not_active IP Right Cessation
- 1977-08-03 IL IL52644A patent/IL52644A0/xx not_active IP Right Cessation
- 1977-08-03 NZ NZ18481677A patent/NZ184816A/xx unknown
- 1977-08-03 NL NL7708616A patent/NL172063C/xx not_active IP Right Cessation
- 1977-08-03 ZA ZA00774701A patent/ZA774701B/xx unknown
- 1977-08-03 DD DD20042077A patent/DD133237A5/xx not_active IP Right Cessation
- 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 MW MW2077A patent/MW2077A1/xx unknown
- 1977-08-03 DK DK346977A patent/DK152366C/da not_active IP Right Cessation
- 1977-08-03 CH CH956277A patent/CH629198A5/fr not_active IP Right Cessation
- 1977-08-03 CA CA283,994A patent/CA1114371A/en not_active Expired
- 1977-08-04 PL PL1977200066A patent/PL111071B1/pl not_active IP Right Cessation
- 1977-08-04 SU SU772507701A patent/SU716523A3/ru active
- 1977-08-04 PH PH20078A patent/PH22114A/en unknown
- 1977-08-04 CS CS775179A patent/CS216246B2/cs unknown
- 1977-08-04 FI FI772362A patent/FI63938C/fi not_active IP Right Cessation
- 1977-08-04 ZM ZM6077A patent/ZM6077A1/xx unknown
- 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 HK403/82A patent/HK40382A/xx unknown
- 1982-09-16 HK HK404/82A patent/HK40482A/xx unknown
- 1982-11-17 SE SE8206546A patent/SE453390B/sv not_active IP Right Cessation
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