JPH0149350B2 - - Google Patents
Info
- Publication number
- JPH0149350B2 JPH0149350B2 JP59198398A JP19839884A JPH0149350B2 JP H0149350 B2 JPH0149350 B2 JP H0149350B2 JP 59198398 A JP59198398 A JP 59198398A JP 19839884 A JP19839884 A JP 19839884A JP H0149350 B2 JPH0149350 B2 JP H0149350B2
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- dihydro
- chloro
- benzodiazepin
- butyryloxy
- 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
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002249 anxiolytic agent Substances 0.000 claims description 3
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- SLPUGTRSHPWDLZ-UHFFFAOYSA-N 5-phenyl-1,4-benzodiazepin-2-one Chemical compound C=12C=CC=CC2=NC(=O)C=NC=1C1=CC=CC=C1 SLPUGTRSHPWDLZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 230000004799 sedative–hypnotic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- -1 N-substituted amino Chemical group 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- UZTFMUBKZQVKLK-UHFFFAOYSA-N 4-acetamidobutanoic acid Chemical compound CC(=O)NCCCC(O)=O UZTFMUBKZQVKLK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940124277 aminobutyric acid Drugs 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- RFCIQRONWHKMIR-UHFFFAOYSA-N 1h-1,4-benzodiazepin-3-ol Chemical class C1=NC(O)=CNC2=CC=CC=C21 RFCIQRONWHKMIR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VJIGUJHYJPPYRG-UHFFFAOYSA-N 3,7-dichloro-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(Cl)N=C1C1=CC=CC=C1Cl VJIGUJHYJPPYRG-UHFFFAOYSA-N 0.000 description 1
- HIDJWBGOQFTDLU-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)(C)OC(=O)NCCCC(O)=O HIDJWBGOQFTDLU-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 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
- 230000006742 locomotor activity Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19839884A JPS6178773A (ja) | 1984-09-21 | 1984-09-21 | Ｃ―３置換１，４―ベンゾジアゼピンおよび医薬組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19839884A JPS6178773A (ja) | 1984-09-21 | 1984-09-21 | Ｃ―３置換１，４―ベンゾジアゼピンおよび医薬組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6178773A JPS6178773A (ja) | 1986-04-22 |
| JPH0149350B2 true JPH0149350B2 (fr) | 1989-10-24 |
Family
ID=16390465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19839884A Granted JPS6178773A (ja) | 1984-09-21 | 1984-09-21 | Ｃ―３置換１，４―ベンゾジアゼピンおよび医薬組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6178773A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03116209A (ja) * | 1989-09-29 | 1991-05-17 | Nissan Motor Co Ltd | 足踏み式パーキングブレーキ装置 |
| WO1992011246A1 (fr) * | 1990-12-25 | 1992-07-09 | Yamanouchi Pharmaceutical Co., Ltd. | Nouveau derive de benzodiazepine |
| JP4898596B2 (ja) * | 2006-08-29 | 2012-03-14 | カヤバ工業株式会社 | 空圧緩衝器 |
-
1984
- 1984-09-21 JP JP19839884A patent/JPS6178773A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6178773A (ja) | 1986-04-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5536832A (en) | N-acyl-2,3-benzodiazepine derivatives pharmaceutical compositions containing them and process for preparing same | |
| EP0340064B1 (fr) | Benzodiazépines, leur procédé et intermédiaires de préparation et leurs applications en thérapeutique | |
| EP0253711B1 (fr) | Nouveaux dérivés du 1H,3H-Pyrrolo [1,2-c] thiazole, leur préparation et les Compositions pharmaceutiques qui les contiennent | |
| US4427590A (en) | Triazolobenzodiazepine derivatives | |
| HU190651B (en) | Process for producing amino-prostaglandine analogues containing 7-oxabicycloheptane ring | |
| EP0446141A1 (fr) | Nouveaux dérivés d'imidazo [1,2-C] quinazoline leur procédé de préparation et les compositions pharmaceutiques les renfermant | |
| EP0008249B1 (fr) | Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique | |
| EP0122889B1 (fr) | 1,4-Benzodiazépines substituées en C-3 et leur utilisation pharmaceutique | |
| HU206117B (en) | Process for producing pyranobenzoxadiazole derivatives and pharmaceutical compositions comprising such compounds | |
| FR2611718A1 (fr) | Analogues d'amino prostaglandines 7-oxabicycloheptane substitues, a action therapeutique | |
| JPH0149350B2 (fr) | ||
| Bose et al. | HojiH zyxwvuts | |
| EP0045251B1 (fr) | Nouveaux dérivés de la thiazolo (3,2-a) pyrimidine, leur préparation et les médicaments qui les contiennent | |
| US4861793A (en) | D-nor-7-ergoline derivatives having anti-Parkinson and antipsychosis activity and pharmaceutical compositions containing them | |
| EP0323325B1 (fr) | Dérivés tricycliques agonistes des récepteurs cholinergiques, procédé pour leur préparation et médicaments en contenant | |
| JP2886586B2 (ja) | 新規グアニジノ安息香酸誘導体及びその酸付加塩 | |
| FR2508457A1 (fr) | Pyrrolo(2,1-b)quinazolines et pyrido(2,1-b)quinazolines substituees, leur preparation et leurs utilisations therapeutiques | |
| JPS6026114B2 (ja) | ベンゾジアゼピン誘導体の製造方法 | |
| US3329701A (en) | Cyanobenzophenones | |
| US4429129A (en) | 1α-Ethyl-1β-(2'-alkoxy carbonyl-2'-hydroxyiminoethyl)-10-methoxy 1,2,3,4,6,7,12,12β-octahydroindolo(2,3A)quinolizines | |
| US4229450A (en) | Carbamates of homolysergols (8β-hydrohyethylergolines) and compositions thereof | |
| JPH0480027B2 (fr) | ||
| BE839365R (fr) | Derives de diazepine | |
| US3499027A (en) | Intermediates for preparing certain 1,4-benzodiazepin-2-(1h)-ones | |
| JPS58194886A (ja) | ナフチリジン誘導体及びその製法 |