JPS5913767A - 新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法 - Google Patents

新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法

Info

Publication number: JPS5913767A
Authority: JP; Japan
Prior art keywords: phenyl; formula; hexahydro; penzodiazonine; group
Prior art date: 1982-07-15
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.): Granted

Application number

JP12223182A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0357897B2 (da

Inventor

Masatoshi Ban

伴　正敏

Kenji Miura

健志三浦

Yutaka Baba

豊馬場

Noriyuki Iwata

岩田　憲之

Mikio Hori

堀　幹夫

Hajime Fujimura

一藤村

Eiichi Suenaga

末永　栄一

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanwa Kagaku Kenkyusho Co Ltd

Original Assignee

Sanwa Kagaku Kenkyusho Co Ltd

Priority date (The priority date 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 date listed.)

1982-07-15

Filing date

1982-07-15

Publication date

1984-01-24

1982-07-15 Application filed by Sanwa Kagaku Kenkyusho Co Ltd filed Critical Sanwa Kagaku Kenkyusho Co Ltd

1982-07-15 Priority to JP12223182A priority Critical patent/JPS5913767A/ja

1984-01-24 Publication of JPS5913767A publication Critical patent/JPS5913767A/ja

1991-09-03 Publication of JPH0357897B2 publication Critical patent/JPH0357897B2/ja

Status Granted legal-status Critical Current

Links

DGNXEVQSRKALRS-UHFFFAOYSA-N 1-phenyl-2h-2,6-benzodiazonine Chemical class C1=CC=CC=C1C1=C2C=CC=CC2=CN=CC=CN1 DGNXEVQSRKALRS-UHFFFAOYSA-N 0.000 title abstract 2
239000012458 free base Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims abstract 6
238000004519 manufacturing process Methods 0.000 claims description 23
238000007796 conventional method Methods 0.000 claims description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
239000000047 product Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims 3
125000004429 atom Chemical group 0.000 claims 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 2
239000012022 methylating agents‎ Substances 0.000 claims 2
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
238000011458 pharmacological treatment Methods 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
230000003533 narcotic effect Effects 0.000 abstract description 6
230000000202 analgesic effect Effects 0.000 abstract description 5
-1 p-fluorobenzoylpropyl Chemical group 0.000 abstract description 5
238000000034 method Methods 0.000 abstract description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000005259 measurement Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000004364 calculation method Methods 0.000 description 15
239000013078 crystal Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000007832 Na2SO4 Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
239000002585 base Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
UVZGOOXAARJPHD-UHFFFAOYSA-N butan-2-one;methanol Chemical compound OC.CCC(C)=O UVZGOOXAARJPHD-UHFFFAOYSA-N 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
239000000730 antalgic agent Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229940035676 analgesics Drugs 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FXFDJSQOCVDXBX-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane Chemical compound C1=CC(F)=CC=C1C1(CCCCl)OCCO1 FXFDJSQOCVDXBX-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
102220501443 Cytosolic iron-sulfur assembly component 3_C27N_mutation Human genes 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000000112 Myalgia Diseases 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical class S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
208000013465 muscle pain Diseases 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000012549 training Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP12223182A 1982-07-15 1982-07-15 新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法 Granted JPS5913767A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP12223182A JPS5913767A (ja)	1982-07-15	1982-07-15	新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12223182A JPS5913767A (ja)	1982-07-15	1982-07-15	新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法

Publications (2)

Publication Number	Publication Date
JPS5913767A true JPS5913767A (ja)	1984-01-24
JPH0357897B2 JPH0357897B2 (da)	1991-09-03

Family

ID=14830812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP12223182A Granted JPS5913767A (ja)	1982-07-15	1982-07-15	新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法

Country Status (1)

Country	Link
JP (1)	JPS5913767A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61158872A (ja) *	1984-12-28	1986-07-18	ハリマセラミック株式会社	キヤスタブル耐火物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3549620A (en) *	1966-06-30	1970-12-22	Sandoz Ag	Substituted hexahydro-1-phenyl-1h-2,6-benzodiazonines

1982
- 1982-07-15 JP JP12223182A patent/JPS5913767A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3549620A (en) *	1966-06-30	1970-12-22	Sandoz Ag	Substituted hexahydro-1-phenyl-1h-2,6-benzodiazonines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61158872A (ja) *	1984-12-28	1986-07-18	ハリマセラミック株式会社	キヤスタブル耐火物

Also Published As

Publication number	Publication date
JPH0357897B2 (da)	1991-09-03

Publication	Publication Date	Title
DE69612003T2 (de)	2001-06-21	Substituierte benzolaktamverbindungen als substanz-p-antagonisten
DE2105743A1 (en)	1972-08-31	2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents
US4272540A (en)	1981-06-09	14-Methoxymorphinan-6-one compounds and therapeutic methods of treating pain and drug dependence with them
DE2305092A1 (de)	1973-08-16	Alpha-aminomethylbenzylalkoholderivate
DE69820989T2 (de)	2004-12-09	Tricyclische benz[e]isoindole und benz[h]isochinoline
DE102004063227A1 (de)	2006-07-06	Tricylische Aminoalkohole, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
CH507240A (de)	1971-05-15	Verfahren zur Herstellung von aromatischen Äthern
JPS5913767A (ja)	1984-01-24	新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法
DE1793837C2 (de)	1978-11-09	N-(Carbalkoxy-acetyl)-diphenylamine
JP3037991B2 (ja)	2000-05-08	新規なアコニチン系化合物および鎮痛・抗炎症剤
DE1695416A1 (de)	1971-04-15	Benzomorphan-derivate und Verfahren zu deren Herstellung
JPS59219276A (ja)	1984-12-10	薬理学上の活性を有する新規なホルミルオキシクロマン類、それらの製法及びそれらを含む製薬組成物
EP0064685A1 (de)	1982-11-17	Dibenzo(de,g)chinolin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
IL27871A (en)	1971-05-26	History of benzomorphan and their preparation
DE2040510A1 (de)	1972-02-17	Neue Azepin-Derivate
CH628041A5 (de)	1982-02-15	Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde.
DD144409A1 (de)	1980-10-15	Verfahren zur herstellung von 5-alkyl-2-eckige klammer auf4-acyloxy-phenyl eckige klammer zu-pyrimidinen
DD283389A5 (de)	1990-10-10	Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen
US4192876A (en)	1980-03-11	4-Hydroxy-3-nitro-quinoline-2(1H)-ones
CA1046514A (en)	1979-01-16	Dihydroapovincaminic acid amines
DE69715223T2 (de)	2003-04-30	Heteroaryloxyethylaminen als 5-ht1a rezeptor liganden
DE3104785A1 (de)	1982-02-25	Basische ether der 4-hydroxy-benzophenone, die als (beta)-blocker wirksam sind, und verfahren zu ihrer herstellung
CN1429819A (zh)	2003-07-16	一种制备抗抑郁药物米氮平的方法
GB2186574A (en)	1987-08-19	Tetracyclic quinazolinones
DE2806879A1 (de)	1979-08-23	4-hydroxy-2-chinolinon-3-carbonsaeure- esterderivate

JPS5913767A - 新規の１−フエニル−２，６−ベンゾジアゾニン誘導体及びその製法 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=14830812

Family Applications (1)

Country Status (1)

Cited By (1)

Citations (1)

Patent Citations (1)

Cited By (1)

Also Published As

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