CA1117110A - Carbostyril derivatives and process for preparation thereof - Google Patents
Carbostyril derivatives and process for preparation thereofInfo
- Publication number
- CA1117110A CA1117110A CA000324227A CA324227A CA1117110A CA 1117110 A CA1117110 A CA 1117110A CA 000324227 A CA000324227 A CA 000324227A CA 324227 A CA324227 A CA 324227A CA 1117110 A CA1117110 A CA 1117110A
- Authority
- CA
- Canada
- Prior art keywords
- group
- propoxy
- dihydrocarbostyril
- compound
- carbon atoms
- 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
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims abstract description 138
- 238000000034 method Methods 0.000 title claims description 90
- 238000002360 preparation method Methods 0.000 title description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 90
- -1 3,4,5-trimethoxybenzoyloxy group Chemical group 0.000 claims abstract description 85
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 53
- 125000005843 halogen group Chemical group 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 13
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 473
- 238000006243 chemical reaction Methods 0.000 claims description 109
- 239000000126 substance Substances 0.000 claims description 22
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- ONEYFZXGNFNRJH-UHFFFAOYSA-N 1-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCNCC1 ONEYFZXGNFNRJH-UHFFFAOYSA-N 0.000 claims description 2
- ADTACPFYJCJJLE-UHFFFAOYSA-N 1-benzyl-5-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CC=3C=CC=CC=3)C(=O)CCC2=C1OCCCN(CC1)CCN1C1=CC=CC=C1 ADTACPFYJCJJLE-UHFFFAOYSA-N 0.000 claims description 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims description 2
- FYLSBGSTHGTSMF-UHFFFAOYSA-N 5-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCN(CC1)CCN1C1=CC=CC=C1 FYLSBGSTHGTSMF-UHFFFAOYSA-N 0.000 claims description 2
- KOWNZCLKAYVANJ-UHFFFAOYSA-N 6-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCN(CC1)CCN1C1=CC=CC=C1 KOWNZCLKAYVANJ-UHFFFAOYSA-N 0.000 claims description 2
- NQHPIZWMYLMHAL-UHFFFAOYSA-N 7-(3-aminopropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(OCCCN)=CC=C21 NQHPIZWMYLMHAL-UHFFFAOYSA-N 0.000 claims description 2
- FYLWSKQQLBEWMU-UHFFFAOYSA-N 7-(3-chloro-2-hydroxypropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(OCC(CCl)O)=CC=C21 FYLWSKQQLBEWMU-UHFFFAOYSA-N 0.000 claims description 2
- RRBYJBJQLCHSIT-UHFFFAOYSA-N 7-[3-(4-benzylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCN1CC1=CC=CC=C1 RRBYJBJQLCHSIT-UHFFFAOYSA-N 0.000 claims description 2
- SPULWLDIJURFIR-UHFFFAOYSA-N 7-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C1=C2NC(=O)C=CC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 SPULWLDIJURFIR-UHFFFAOYSA-N 0.000 claims description 2
- GTTWBLBQRGTZTI-UHFFFAOYSA-N 7-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 GTTWBLBQRGTZTI-UHFFFAOYSA-N 0.000 claims description 2
- UHLXVWIMGXDONK-UHFFFAOYSA-N 7-[3-[4-(2-ethoxyphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound CCOC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 UHLXVWIMGXDONK-UHFFFAOYSA-N 0.000 claims description 2
- SKHLKHODMJVMFM-UHFFFAOYSA-N 7-[3-[4-(2-fluorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound FC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 SKHLKHODMJVMFM-UHFFFAOYSA-N 0.000 claims description 2
- HEZSJVTZKUSOIZ-UHFFFAOYSA-N 8-bromo-5-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C(Br)=CC=C2OCCCCl HEZSJVTZKUSOIZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- AQRDPQOVPUDAQO-UHFFFAOYSA-N n-(2-bromoethyl)aniline Chemical compound BrCCNC1=CC=CC=C1 AQRDPQOVPUDAQO-UHFFFAOYSA-N 0.000 claims description 2
- NQCVIXJSFZMILF-UHFFFAOYSA-N 7-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(OCCCCl)=CC=C21 NQCVIXJSFZMILF-UHFFFAOYSA-N 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 claims 1
- FBQIUSDQWOLCNY-UHFFFAOYSA-N 1-(2-ethoxyphenyl)piperazine Chemical compound CCOC1=CC=CC=C1N1CCNCC1 FBQIUSDQWOLCNY-UHFFFAOYSA-N 0.000 claims 1
- IVTZRJKKXSKXKO-UHFFFAOYSA-N 1-(2-fluorophenyl)piperazine Chemical compound FC1=CC=CC=C1N1CCNCC1 IVTZRJKKXSKXKO-UHFFFAOYSA-N 0.000 claims 1
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 claims 1
- VZOFCATXWWIFHP-UHFFFAOYSA-N 1-benzyl-5-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1CN(C=2C=CC=CC=2)CCN1CC(O)COC(C=1CCC2=O)=CC=CC=1N2CC1=CC=CC=C1 VZOFCATXWWIFHP-UHFFFAOYSA-N 0.000 claims 1
- MDJOKTXXPXPSFJ-UHFFFAOYSA-N 1-methyl-7-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1=C2N(C)C(=O)CCC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 MDJOKTXXPXPSFJ-UHFFFAOYSA-N 0.000 claims 1
- JHWVAWUKMRXHCM-UHFFFAOYSA-N 5-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCCl JHWVAWUKMRXHCM-UHFFFAOYSA-N 0.000 claims 1
- DFQTUHQFWNUAKJ-UHFFFAOYSA-N 6-(3-chloropropoxy)-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=CC(OCCCCl)=CC=C21 DFQTUHQFWNUAKJ-UHFFFAOYSA-N 0.000 claims 1
- FNQUGGIQFZPDRL-UHFFFAOYSA-N 7-(3-chloropropoxy)-1-methyl-3,4-dihydroquinolin-2-one Chemical compound C1=C(OCCCCl)C=C2N(C)C(=O)CCC2=C1 FNQUGGIQFZPDRL-UHFFFAOYSA-N 0.000 claims 1
- XYDYSBCHGVQENV-UHFFFAOYSA-N 7-(3-chloropropoxy)-1h-quinolin-2-one Chemical compound C1=CC(=O)NC2=CC(OCCCCl)=CC=C21 XYDYSBCHGVQENV-UHFFFAOYSA-N 0.000 claims 1
- SRMLSNBGMDJSJH-UHFFFAOYSA-N 7-(4-chlorobutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(OCCCCCl)=CC=C21 SRMLSNBGMDJSJH-UHFFFAOYSA-N 0.000 claims 1
- IVZCTUCBSMZQJP-UHFFFAOYSA-N 7-[3-[4-(2-chlorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound ClC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 IVZCTUCBSMZQJP-UHFFFAOYSA-N 0.000 claims 1
- AYOYRQBAZIBAOY-UHFFFAOYSA-N 7-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-1h-quinolin-2-one Chemical compound COC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)C=CC3=CC=2)CC1 AYOYRQBAZIBAOY-UHFFFAOYSA-N 0.000 claims 1
- XRXBZJLXUCSIKS-UHFFFAOYSA-N 7-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound COC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 XRXBZJLXUCSIKS-UHFFFAOYSA-N 0.000 claims 1
- ZKAYRIOGIKAXJC-UHFFFAOYSA-N 7-[3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound ClC1=CC=CC(N2CCN(CCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1 ZKAYRIOGIKAXJC-UHFFFAOYSA-N 0.000 claims 1
- MLUSPPKOSUCWLV-UHFFFAOYSA-N 7-[3-[4-(4-methylphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(C)=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 MLUSPPKOSUCWLV-UHFFFAOYSA-N 0.000 claims 1
- USIMZAIRLDAIQJ-UHFFFAOYSA-N 7-[4-(4-phenylpiperazin-1-yl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCCN(CC1)CCN1C1=CC=CC=C1 USIMZAIRLDAIQJ-UHFFFAOYSA-N 0.000 claims 1
- MNNDUPMFGLCHOD-UHFFFAOYSA-N 8-bromo-5-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C1=2C=CC(=O)NC=2C(Br)=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 MNNDUPMFGLCHOD-UHFFFAOYSA-N 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 abstract description 19
- 230000001387 anti-histamine Effects 0.000 abstract description 18
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 366
- 239000013078 crystal Substances 0.000 description 362
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 304
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 194
- 125000004193 piperazinyl group Chemical group 0.000 description 179
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 136
- 235000019441 ethanol Nutrition 0.000 description 108
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
- 235000013350 formula milk Nutrition 0.000 description 103
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
- 229960001701 chloroform Drugs 0.000 description 68
- 238000002844 melting Methods 0.000 description 68
- 230000008018 melting Effects 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 49
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- 238000004821 distillation Methods 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 238000001914 filtration Methods 0.000 description 25
- 229960004592 isopropanol Drugs 0.000 description 25
- 238000010992 reflux Methods 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 19
- 239000000460 chlorine Chemical group 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
- BCURJLKUQHLLSZ-UHFFFAOYSA-N ethanol;1h-quinolin-2-one Chemical compound CCO.C1=CC=C2NC(=O)C=CC2=C1 BCURJLKUQHLLSZ-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 241000699670 Mus sp. Species 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 15
- 229940086542 triethylamine Drugs 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 150000007514 bases Chemical class 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 230000002140 halogenating effect Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 229960000443 hydrochloric acid Drugs 0.000 description 12
- 239000012442 inert solvent Substances 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 235000011167 hydrochloric acid Nutrition 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 9
- 229960001340 histamine Drugs 0.000 description 9
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229920000084 Gum arabic Polymers 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- WKWAVURMIFLVLL-UHFFFAOYSA-N methanol;dihydrochloride Chemical compound Cl.Cl.OC WKWAVURMIFLVLL-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
- 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
- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3778378A JPS54130587A (en) | 1978-03-30 | 1978-03-30 | Carbostyryl derivative |
| JP37783/78 | 1978-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117110A true CA1117110A (en) | 1982-01-26 |
Family
ID=12507080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000324227A Expired CA1117110A (en) | 1978-03-30 | 1979-03-27 | Carbostyril derivatives and process for preparation thereof |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4734416A (enExample) |
| JP (1) | JPS54130587A (enExample) |
| AT (1) | AT376432B (enExample) |
| AU (1) | AU515531B2 (enExample) |
| BE (1) | BE875174A (enExample) |
| CA (1) | CA1117110A (enExample) |
| CH (2) | CH641455A5 (enExample) |
| DE (2) | DE2953723C2 (enExample) |
| DK (1) | DK158225C (enExample) |
| ES (4) | ES479134A1 (enExample) |
| FI (1) | FI70704C (enExample) |
| FR (1) | FR2421174A1 (enExample) |
| GB (1) | GB2017701B (enExample) |
| IT (1) | IT1119284B (enExample) |
| MX (1) | MX5862E (enExample) |
| NL (1) | NL183189C (enExample) |
| NO (1) | NO151321C (enExample) |
| PT (1) | PT69422A (enExample) |
| SE (1) | SE434945B (enExample) |
| SU (2) | SU1140687A3 (enExample) |
| ZA (1) | ZA791516B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9089567B2 (en) | 2001-01-29 | 2015-07-28 | Otsuka Pharmaceutical Co., Ltd. | Method of treating cognitive impairments and schizophrenias |
| US9359302B2 (en) | 2001-09-25 | 2016-06-07 | Otsuka Pharmaceutical Co., Ltd. | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2827566A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Mannheim Gmbh | 1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung |
| DE3034237A1 (de) * | 1979-09-18 | 1981-04-16 | Otsuka Pharmaceutical Co. Ltd., Tokyo | Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel |
| PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| JPS57193461A (en) * | 1981-05-22 | 1982-11-27 | Otsuka Pharmaceut Co Ltd | Benzazepine derivative |
| CN85108214A (zh) * | 1984-11-22 | 1986-08-20 | 赫彻斯特股份公司 | 新的取代的苯基哌嗪衍生物及其药物的制造方法 |
| JPS6129331A (ja) * | 1985-03-13 | 1986-02-10 | アラ−ガン・ハンフリ− | 検眼装置 |
| DK588486A (da) * | 1985-12-09 | 1987-06-10 | Otsuka Pharma Co Ltd | Anvendelse af en forbindelse til behandling af hypoxi |
| DK167187A (da) * | 1986-04-02 | 1987-10-03 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, fremgangsmaade til fremstilling af saadanne forbindelser og laegemiddel indeholdende disse |
| KR940000785B1 (ko) * | 1986-04-02 | 1994-01-31 | 오오쓰까세이야꾸 가부시끼가이샤 | 카르보스티릴 유도체 및 그의 염의 제조 방법 |
| EP0255134B1 (en) * | 1986-07-31 | 1993-03-03 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof, process for preparing them, and cardiotonic composition containing same |
| JPH0696555B2 (ja) * | 1986-07-31 | 1994-11-30 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| US4803203A (en) * | 1986-11-05 | 1989-02-07 | Warner-Lambert Company | Phenyl and heterocyclic piperazinyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| JPS63141967A (ja) * | 1986-11-21 | 1988-06-14 | エイ・エッチ・ロビンス・カンパニー・インコーポレーテッド | 抗アレルギー薬として有用な１−アリールオキシー４−［（４−アリール）−１−ピペラジニル］−２−ブタノール |
| FR2637591B1 (fr) * | 1988-10-11 | 1992-10-23 | Synthelabo | Derives de quinoleinone, leur preparation et leur application en therapeutique |
| JP2608788B2 (ja) * | 1988-10-31 | 1997-05-14 | 大塚製薬 株式会社 | 精神分裂病治療剤 |
| US5006528A (en) * | 1988-10-31 | 1991-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| JP2900130B2 (ja) * | 1995-03-16 | 1999-06-02 | 大塚製薬株式会社 | カルボスチリル誘導体及び該誘導体を含有する精神分裂病治療剤 |
| AR032641A1 (es) * | 2001-01-29 | 2003-11-19 | Otsuka Pharma Co Ltd | Agonista de subtipo de receptor 5-ht 1a. |
| MY129350A (en) * | 2001-04-25 | 2007-03-30 | Bristol Myers Squibb Co | Aripiprazole oral solution |
| PE20030445A1 (es) * | 2001-09-25 | 2003-07-26 | Otsuka Pharma Co Ltd | Sustancia medicinal de aripiprazol de baja higroscopicidad y proceso para la preparacion de la misma |
| US8703772B2 (en) | 2001-09-25 | 2014-04-22 | Otsuka Pharmaceutical Co., Ltd. | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
| AU2003291757A1 (en) * | 2002-11-08 | 2004-06-03 | Bristol-Myers Squibb Company | Formulations of low solubility bioactive agents and processes for making the same |
| SI1480953T2 (sl) * | 2003-01-09 | 2010-12-31 | Otsuka Pharma Co Ltd | Postopek za pripravo aripiprazola |
| WO2004064752A2 (en) * | 2003-01-22 | 2004-08-05 | Alkermes Controlled Therapeutics, Inc. | Method of preparing sustained release microparticles |
| AU2004265243A1 (en) * | 2003-06-20 | 2005-02-24 | Arena Pharmaceuticals, Inc. | N-phenyl-piperazine derivatives and methods of prophylaxis or treatment of 5HT2c receptor associated diseases |
| US6987111B2 (en) | 2003-08-06 | 2006-01-17 | Alkermes Controlled Therapeutics, Ii | Aripiprazole, olanzapine and haloperidol pamoate salts |
| US20050032781A1 (en) * | 2003-08-06 | 2005-02-10 | Elliot Ehrich | Methods for administering active agents to CYP 2D6 sensitive patients |
| ES2315721T5 (es) | 2003-10-23 | 2012-08-24 | Otsuka Pharmaceutical Co., Ltd. | Formulación de aripiprazol inyectable estéril de liberación controlada y procedimiento |
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| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
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| CA801037A (en) * | 1968-12-10 | Regnier Gilbert | Procede de preparation de nouveaux derives du piperazino-phenylethanol | |
| GB1021522A (en) * | 1963-05-10 | 1966-03-02 | Ici Ltd | 2-quinolone derivatives |
| GB1075156A (en) * | 1963-08-27 | 1967-07-12 | Luso Farmaco Inst | Substituted piperazines |
| NL131192C (enExample) * | 1965-06-16 | |||
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
| US3706749A (en) * | 1967-03-30 | 1972-12-19 | Mcneilab Inc | N-acyl carbostyrils |
| US3703522A (en) * | 1967-03-30 | 1972-11-21 | Mcneilab Inc | Carbostyril derivatives |
| US3511841A (en) * | 1967-05-29 | 1970-05-12 | Sterling Drug Inc | 1-((4-,5-,6-,and 7-azaindolyl)-lower-alkyl)- 4-substituted-piperazines |
| US3635976A (en) * | 1967-12-20 | 1972-01-18 | Pennwalt Corp | 1 - heterocyclic alkyl-1 2 3 4-tetrahydroquinazolinones and analgesic intermediates thereof |
| CH534687A (de) * | 1968-07-05 | 1973-03-15 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins |
| DE1795362A1 (de) * | 1968-09-19 | 1972-01-05 | Boehringer Mannheim Gmbh | Basische AEther und Verfahren zur Herstellung derselben |
| DE2123923A1 (de) * | 1971-05-14 | 1972-11-23 | Boehringer Mannheim Gmbh, 6800 Mannheim | 4-eckige Klammer auf omega- (Flavon-7yl-oxy) -alkyl eckige Klammer zu -pigerazin-Derivate und Verfahren zu ihrer Herstellung |
| BE884459Q (fr) * | 1971-05-14 | 1981-01-26 | Boehringer Mannheim Gmbh | Derives de la 4-(omega-(coumarine-7-yl-oxy)-alkyl)-piperazine et procede de preparation |
| DE2335432A1 (de) * | 1973-07-12 | 1975-01-30 | Boehringer Mannheim Gmbh | 3,4-dihydro-2h-naphthalinon-(1)5-oxy-propyl-piperazin-derivate und verfahren zu ihrer herstellung |
| JPS517672B2 (enExample) * | 1972-04-13 | 1976-03-10 | ||
| US3910924A (en) * | 1972-04-13 | 1975-10-07 | Otsuka Pharma Co Ltd | 3,4-Dihydrocarbostyril derivatives and a process for preparing the same |
| US4256890A (en) * | 1972-09-14 | 1981-03-17 | Otsukapharmaceutical Co., Ltd. | 3,4-Dihydrocarbostyril derivatives and process for producing the same |
| NL7314812A (enExample) * | 1972-11-02 | 1974-05-06 | ||
| DE2334009A1 (de) * | 1973-07-04 | 1975-01-23 | Boehringer Mannheim Gmbh | Purin-derivate sowie verfahren zu ihrer herstellung |
| US4083853A (en) * | 1973-09-08 | 1978-04-11 | Eisai Co., Ltd. | 1,3-Benzodioxol derivatives |
| US3981864A (en) * | 1973-09-08 | 1976-09-21 | Eisai Co., Ltd. | 1,3-Benzodioxol derivatives |
| US4026895A (en) * | 1973-09-08 | 1977-05-31 | Eisai Co., Ltd. | 1,3-Benzodioxol derivatives |
| GB1451900A (en) * | 1973-10-30 | 1976-10-06 | Sandoz Ltd | Quinolin-2-1h-ones |
| JPS5089376A (enExample) * | 1973-12-19 | 1975-07-17 | ||
| US4032528A (en) * | 1974-03-25 | 1977-06-28 | Sandoz, Inc. | 1,4-substituted-quinolin-2(1h)-ones as cns agents |
| US3983121A (en) * | 1974-07-01 | 1976-09-28 | Council Of Scientific And Industrial Research | 1-Substituted 4-(β-2-quinolylethyl)piperazines and 1,2,3,4-tetrahydroquinolyl-ethyl analogues thereof |
| US3940397A (en) * | 1974-11-13 | 1976-02-24 | E. R. Squibb & Sons, Inc. | 2-[(Substituted-piperazinyl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones |
| DE2631317A1 (de) * | 1975-07-23 | 1977-02-17 | Sandoz Ag | Organische verbindungen, ihre verwendung und herstellung |
| US3994900A (en) * | 1976-01-23 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 6-(Or 8)-[[(substituted amino)alkyl]oxy(or thio)]-3,4-dihydro-4-phenyl-2(1H)-quinolinones |
| ES456325A1 (es) * | 1976-02-27 | 1978-05-01 | Sandoz Ag | Un procedimiento para la preparacion de nuevos derivados delacido 4-hidroxi-2-quinolinon-3-carboxilico. |
| US4210753A (en) * | 1976-03-17 | 1980-07-01 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds |
| CH619453A5 (enExample) * | 1976-03-17 | 1980-09-30 | Otsuka Pharma Co Ltd | |
| DE2719562C2 (de) * | 1976-05-08 | 1986-05-07 | Otsuka Pharmaceutical Co. Ltd., Tokio/Tokyo | 3, 4-Dihydrocarbostyrilderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| US4110449A (en) * | 1977-05-23 | 1978-08-29 | E. R. Squibb & Sons, Inc. | 2-substituted benzisothiazol-3-ones |
| US4166116A (en) * | 1977-11-11 | 1979-08-28 | Canadian Patents And Development Limited | Pharmaceutical compositions containing piperazinyl acylhydroxamic acid derivatives to treat inflammation or anaphylactic allergy conditions |
| DE2960178D1 (en) * | 1978-06-06 | 1981-04-09 | Hoechst Ag | New substituted phenylpiperazine derivatives, pharmaceutical compositions containing them and process for their preparation |
| DE2827566A1 (de) | 1978-06-23 | 1980-01-10 | Boehringer Mannheim Gmbh | 1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung |
-
1978
- 1978-03-30 JP JP3778378A patent/JPS54130587A/ja active Granted
-
1979
- 1979-03-27 DE DE2953723A patent/DE2953723C2/de not_active Expired
- 1979-03-27 DE DE2912105A patent/DE2912105C2/de not_active Expired
- 1979-03-27 CA CA000324227A patent/CA1117110A/en not_active Expired
- 1979-03-28 FI FI791034A patent/FI70704C/fi not_active IP Right Cessation
- 1979-03-28 AU AU45480/79A patent/AU515531B2/en not_active Expired
- 1979-03-28 US US06/024,602 patent/US4734416A/en not_active Expired - Lifetime
- 1979-03-29 FR FR7907863A patent/FR2421174A1/fr active Granted
- 1979-03-29 CH CH295379A patent/CH641455A5/de not_active IP Right Cessation
- 1979-03-29 DK DK128679A patent/DK158225C/da not_active IP Right Cessation
- 1979-03-29 SE SE7902794A patent/SE434945B/sv not_active IP Right Cessation
- 1979-03-29 AT AT0235179A patent/AT376432B/de not_active IP Right Cessation
- 1979-03-29 SU SU792745704A patent/SU1140687A3/ru active
- 1979-03-29 NO NO791049A patent/NO151321C/no unknown
- 1979-03-29 BE BE0/194281A patent/BE875174A/xx not_active IP Right Cessation
- 1979-03-30 ES ES479134A patent/ES479134A1/es not_active Expired
- 1979-03-30 IT IT67674/79A patent/IT1119284B/it active
- 1979-03-30 MX MX797848U patent/MX5862E/es unknown
- 1979-03-30 GB GB7911155A patent/GB2017701B/en not_active Expired
- 1979-03-30 PT PT69422A patent/PT69422A/pt unknown
- 1979-03-30 NL NLAANVRAGE7902514,A patent/NL183189C/xx not_active IP Right Cessation
- 1979-03-30 ZA ZA791516A patent/ZA791516B/xx unknown
- 1979-12-17 ES ES486990A patent/ES486990A1/es not_active Expired
- 1979-12-17 ES ES486992A patent/ES486992A1/es not_active Expired
- 1979-12-17 ES ES486991A patent/ES486991A1/es not_active Expired
-
1981
- 1981-09-08 SU SU813328599A patent/SU1232144A3/ru active
-
1982
- 1982-03-26 CH CH190082A patent/CH641350A5/de not_active IP Right Cessation
-
1987
- 1987-03-12 US US07/025,193 patent/US4824840A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9089567B2 (en) | 2001-01-29 | 2015-07-28 | Otsuka Pharmaceutical Co., Ltd. | Method of treating cognitive impairments and schizophrenias |
| US9387207B2 (en) | 2001-01-29 | 2016-07-12 | Otsuka Pharmaceutical Co., Ltd. | 5-HT1A receptor subtype agonist |
| US9359302B2 (en) | 2001-09-25 | 2016-06-07 | Otsuka Pharmaceutical Co., Ltd. | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
| US10150735B2 (en) | 2001-09-25 | 2018-12-11 | Otsuka Pharmaceutical Co., Ltd. | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
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