JPS6176491A - 新規なイソオキサゾロキノリン誘導体、製造のための方法および中間体、薬剤としての用途並びに薬剤含有組成物 - Google Patents
新規なイソオキサゾロキノリン誘導体、製造のための方法および中間体、薬剤としての用途並びに薬剤含有組成物Info
- Publication number
- JPS6176491A JPS6176491A JP60136225A JP13622585A JPS6176491A JP S6176491 A JPS6176491 A JP S6176491A JP 60136225 A JP60136225 A JP 60136225A JP 13622585 A JP13622585 A JP 13622585A JP S6176491 A JPS6176491 A JP S6176491A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- derivative
- carbon atoms
- phenyl
- group
- 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.)
- Pending
Links
- 239000003814 drug Substances 0.000 title claims description 13
- 229940079593 drug Drugs 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title description 17
- 238000004519 manufacturing process Methods 0.000 title description 6
- DBHMZXRSMFKHLA-UHFFFAOYSA-N [1,2]oxazolo[3,4-h]quinoline Chemical class C1=CN=C2C3=CON=C3C=CC2=C1 DBHMZXRSMFKHLA-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- IXQREGLIGLUSKL-UHFFFAOYSA-N 1H-[1,2]oxazolo[3,4-h]quinolin-2-one Chemical class C1=CC2=NOC=C2C2=C1C=CC(=O)N2 IXQREGLIGLUSKL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011737 fluorine Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims description 4
- UBFZRACRSUKOKO-UHFFFAOYSA-N 2-phenyl-[1,2]oxazolo[4,5-c]quinolin-3-one Chemical compound O1C(C2=CC=CC=C2N=C2)=C2C(=O)N1C1=CC=CC=C1 UBFZRACRSUKOKO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IPXYGRNOWPRDPJ-UHFFFAOYSA-N 8-methoxy-2-phenyl-[1,2]oxazolo[4,5-c]quinolin-3-one Chemical compound C12=CC(OC)=CC=C2N=CC(C2=O)=C1ON2C1=CC=CC=C1 IPXYGRNOWPRDPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- TXVJTYRZUCZKJM-UHFFFAOYSA-N 8-fluoro-2-phenyl-[1,2]oxazolo[4,5-c]quinolin-3-one Chemical compound C12=CC(F)=CC=C2N=CC(C2=O)=C1ON2C1=CC=CC=C1 TXVJTYRZUCZKJM-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 abstract description 7
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- IHNINSVQYKIZIC-UHFFFAOYSA-N 2h-quinolin-3-one Chemical compound C1=CC=CC2=CC(=O)CN=C21 IHNINSVQYKIZIC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
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- 239000004020 conductor Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229960003529 diazepam Drugs 0.000 description 2
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- RRCKMNOMCSGFEU-UHFFFAOYSA-N 2-phenyl-8-(trifluoromethyl)-[1,2]oxazolo[4,5-c]quinolin-3-one Chemical compound C12=CC(C(F)(F)F)=CC=C2N=CC(C2=O)=C1ON2C1=CC=CC=C1 RRCKMNOMCSGFEU-UHFFFAOYSA-N 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- CDPXSMNKRFLXHU-UHFFFAOYSA-N 6-chloro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=C2C(=O)C(C(=O)O)=CNC2=C1 CDPXSMNKRFLXHU-UHFFFAOYSA-N 0.000 description 1
- UYNFMSZMMDOGIW-UHFFFAOYSA-N 6-chloro-n-hydroxy-4-oxo-n-phenyl-1h-quinoline-3-carboxamide Chemical group C=1N=C2C=CC(Cl)=CC2=C(O)C=1C(=O)N(O)C1=CC=CC=C1 UYNFMSZMMDOGIW-UHFFFAOYSA-N 0.000 description 1
- RESVKOSPFKHQBK-UHFFFAOYSA-N 6-ethyl-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound N1C=C(C(O)=O)C(=O)C2=CC(CC)=CC=C21 RESVKOSPFKHQBK-UHFFFAOYSA-N 0.000 description 1
- AIKLXQUJEISZIH-UHFFFAOYSA-N 6-ethyl-n-hydroxy-4-oxo-n-phenyl-1h-quinoline-3-carboxamide Chemical compound OC=1C2=CC(CC)=CC=C2N=CC=1C(=O)N(O)C1=CC=CC=C1 AIKLXQUJEISZIH-UHFFFAOYSA-N 0.000 description 1
- KCEJQAATYWQMMQ-UHFFFAOYSA-N 6-fluoro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=C1 KCEJQAATYWQMMQ-UHFFFAOYSA-N 0.000 description 1
- QINDQBOCFNCPKR-UHFFFAOYSA-N 8-ethyl-2-phenyl-[1,2]oxazolo[4,5-c]quinolin-3-one Chemical compound C12=CC(CC)=CC=C2N=CC(C2=O)=C1ON2C1=CC=CC=C1 QINDQBOCFNCPKR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000012012 Paullinia yoco Nutrition 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 231100000871 behavioral problem Toxicity 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- NLMBADNQYMQLLQ-UHFFFAOYSA-N n-(4-chlorophenyl)-n-hydroxy-4-oxo-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C=CC=CC2=C(O)C=1C(=O)N(O)C1=CC=C(Cl)C=C1 NLMBADNQYMQLLQ-UHFFFAOYSA-N 0.000 description 1
- ZCSGPUFLTGSMAT-UHFFFAOYSA-N n-hydroxy-4-oxo-n-phenyl-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C=CC=CC2=C(O)C=1C(=O)N(O)C1=CC=CC=C1 ZCSGPUFLTGSMAT-UHFFFAOYSA-N 0.000 description 1
- SRBFJKAIHWNKBR-UHFFFAOYSA-N n-hydroxy-7-methoxy-4-oxo-n-phenyl-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(OC)=CC=C2C(O)=C1C(=O)N(O)C1=CC=CC=C1 SRBFJKAIHWNKBR-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
- Color Television Systems (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8409961A FR2566407B1 (fr) | 1984-06-25 | 1984-06-25 | Nouveaux derives de l'isoxazoloquinoleine, procede de preparation, application a titre de medicaments, et compositions les renfermant |
| FR8409961 | 1984-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6176491A true JPS6176491A (ja) | 1986-04-18 |
Family
ID=9305387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60136225A Pending JPS6176491A (ja) | 1984-06-25 | 1985-06-24 | 新規なイソオキサゾロキノリン誘導体、製造のための方法および中間体、薬剤としての用途並びに薬剤含有組成物 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0168309B1 (en, 2012) |
| JP (1) | JPS6176491A (en, 2012) |
| KR (1) | KR860000296A (en, 2012) |
| AT (1) | ATE32899T1 (en, 2012) |
| CA (1) | CA1225993A (en, 2012) |
| DE (1) | DE3561818D1 (en, 2012) |
| DK (1) | DK284085A (en, 2012) |
| ES (1) | ES8604599A1 (en, 2012) |
| FI (1) | FI79322C (en, 2012) |
| FR (1) | FR2566407B1 (en, 2012) |
| GR (1) | GR851530B (en, 2012) |
| HU (1) | HU192234B (en, 2012) |
| IL (1) | IL75562A (en, 2012) |
| MA (1) | MA20461A1 (en, 2012) |
| NZ (1) | NZ212532A (en, 2012) |
| OA (1) | OA08045A (en, 2012) |
| PT (1) | PT80690B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920117A (en) * | 1989-06-09 | 1990-04-24 | Hoechst-Roussel Pharmaceuticals Inc. | 4,5,5a,6-tetrahydro-3H-isoxazolo(5,4,3-kl)acridines, pharmaceutical compositions and use |
| US5182290A (en) * | 1991-08-27 | 1993-01-26 | Neurogen Corporation | Certain oxazoloquinolinones; a new class of GABA brain receptor ligands |
| CA2258822A1 (en) * | 1996-06-20 | 1997-12-24 | Sean Kerwin | Compounds and methods for providing pharmacologically active preparations and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2537140B1 (fr) * | 1982-12-07 | 1986-07-18 | Roussel Uclaf | Nouveaux derives de la 4-hydroxy-3-quinoleine carboxamide, leur sels, procede de preparation, application a titre de medicaments, et compositions les renfermant |
-
1984
- 1984-06-25 FR FR8409961A patent/FR2566407B1/fr not_active Expired
-
1985
- 1985-06-05 FI FI852249A patent/FI79322C/fi not_active IP Right Cessation
- 1985-06-19 IL IL75562A patent/IL75562A/xx unknown
- 1985-06-20 AT AT85401234T patent/ATE32899T1/de active
- 1985-06-20 DE DE8585401234T patent/DE3561818D1/de not_active Expired
- 1985-06-20 EP EP85401234A patent/EP0168309B1/fr not_active Expired
- 1985-06-21 CA CA000484819A patent/CA1225993A/fr not_active Expired
- 1985-06-24 PT PT80690A patent/PT80690B/pt not_active IP Right Cessation
- 1985-06-24 DK DK284085A patent/DK284085A/da not_active Application Discontinuation
- 1985-06-24 MA MA20688A patent/MA20461A1/fr unknown
- 1985-06-24 JP JP60136225A patent/JPS6176491A/ja active Pending
- 1985-06-24 ES ES544488A patent/ES8604599A1/es not_active Expired
- 1985-06-24 NZ NZ212532A patent/NZ212532A/xx unknown
- 1985-06-24 HU HU852472A patent/HU192234B/hu not_active IP Right Cessation
- 1985-06-24 GR GR851530A patent/GR851530B/el unknown
- 1985-06-25 OA OA58619A patent/OA08045A/xx unknown
- 1985-06-25 KR KR1019850004504A patent/KR860000296A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0168309B1 (fr) | 1988-03-09 |
| GR851530B (en, 2012) | 1985-11-25 |
| PT80690B (fr) | 1987-03-31 |
| HUT38948A (en) | 1986-07-28 |
| EP0168309A1 (fr) | 1986-01-15 |
| ES8604599A1 (es) | 1986-02-01 |
| FR2566407A1 (fr) | 1985-12-27 |
| DE3561818D1 (en) | 1988-04-14 |
| DK284085A (da) | 1985-12-26 |
| KR860000296A (ko) | 1986-01-27 |
| FI79322B (fi) | 1989-08-31 |
| ATE32899T1 (de) | 1988-03-15 |
| NZ212532A (en) | 1988-08-30 |
| MA20461A1 (fr) | 1985-12-31 |
| IL75562A0 (en) | 1985-10-31 |
| HU192234B (en) | 1987-05-28 |
| FI79322C (fi) | 1989-12-11 |
| ES544488A0 (es) | 1986-02-01 |
| CA1225993A (fr) | 1987-08-25 |
| FI852249L (fi) | 1985-12-26 |
| PT80690A (fr) | 1985-07-01 |
| FI852249A0 (fi) | 1985-06-05 |
| IL75562A (en) | 1988-07-31 |
| OA08045A (fr) | 1987-01-31 |
| DK284085D0 (da) | 1985-06-24 |
| FR2566407B1 (fr) | 1986-09-26 |
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