JPH0223550B2 - - Google Patents
Info
- Publication number
- JPH0223550B2 JPH0223550B2 JP55070176A JP7017680A JPH0223550B2 JP H0223550 B2 JPH0223550 B2 JP H0223550B2 JP 55070176 A JP55070176 A JP 55070176A JP 7017680 A JP7017680 A JP 7017680A JP H0223550 B2 JPH0223550 B2 JP H0223550B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- lower alkyl
- group
- hydrogen atom
- alkyl 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- -1 lipid peroxide Chemical class 0.000 abstract description 2
- 150000002632 lipids Chemical class 0.000 abstract description 2
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- RVSGRNKUJJUAPV-UHFFFAOYSA-N benzo[d][1,2]benzoxazepine Chemical class O1N=CC2=CC=CC=C2C2=CC=CC=C12 RVSGRNKUJJUAPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 210000000056 organ Anatomy 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKMRNPBEBOXDCJ-UHFFFAOYSA-N ethyl 10-methoxy-5,6-dihydrobenzo[b][1,4]benzoxazepine-3-carboxylate Chemical compound C1NC2=CC(C(=O)OCC)=CC=C2OC2=C1C=CC=C2OC ZKMRNPBEBOXDCJ-UHFFFAOYSA-N 0.000 description 1
- VULNECPXHBGRLF-UHFFFAOYSA-N ethyl 3-acetamido-4-(3-methoxyphenoxy)benzoate Chemical compound CC(=O)NC1=CC(C(=O)OCC)=CC=C1OC1=CC=CC(OC)=C1 VULNECPXHBGRLF-UHFFFAOYSA-N 0.000 description 1
- SESCUIFCAAXPML-UHFFFAOYSA-N ethyl 9-methoxy-6-methylbenzo[b][1,4]benzoxazepine-3-carboxylate;hydrochloride Chemical compound Cl.CC1=NC2=CC(C(=O)OCC)=CC=C2OC2=CC(OC)=CC=C21 SESCUIFCAAXPML-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7017680A JPS56166180A (en) | 1980-05-28 | 1980-05-28 | Dibenzoxazepine derivative and its preparation |
| IL62894A IL62894A (en) | 1980-05-28 | 1981-05-18 | Dibenzoxazepine derivatives,process for preparing the same and pharmaceutical compositions comprising the same |
| ZA00813385A ZA813385B (en) | 1980-05-28 | 1981-05-20 | Dibenzoxazepine derivative,process for preparing the same,and pharmaceutical composition comprising the same |
| KR1019810001793A KR850000212B1 (ko) | 1980-05-28 | 1981-05-23 | 디벤조옥사제핀 유도체의 제법 |
| AT81104100T ATE6645T1 (de) | 1980-05-28 | 1981-05-27 | Dibenzoxazepin-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| EP81104100A EP0040860B1 (en) | 1980-05-28 | 1981-05-27 | Dibenzoxazepine derivative, process for preparing the same and pharmaceutical composition comprising the same |
| CA000378457A CA1162189A (en) | 1980-05-28 | 1981-05-27 | Dibenzoxazepine derivative, process for preparing the same, and pharmaceutical composition comprising the same |
| HU811589A HU183456B (en) | 1980-05-28 | 1981-05-27 | Process for preparing dibenzoxazepines and pharmaceutical compositions containing thereof |
| DE8181104100T DE3162614D1 (en) | 1980-05-28 | 1981-05-27 | Dibenzoxazepine derivative, process for preparing the same and pharmaceutical composition comprising the same |
| MX187533A MX157054A (es) | 1980-05-28 | 1981-05-28 | Procedimiento para preparar derivados de disenzoxazepina |
| US06/354,651 US4435391A (en) | 1980-05-28 | 1982-03-04 | Dibenzoxazepine derivative, and pharmaceutical composition comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7017680A JPS56166180A (en) | 1980-05-28 | 1980-05-28 | Dibenzoxazepine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56166180A JPS56166180A (en) | 1981-12-21 |
| JPH0223550B2 true JPH0223550B2 (en]) | 1990-05-24 |
Family
ID=13423954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7017680A Granted JPS56166180A (en) | 1980-05-28 | 1980-05-28 | Dibenzoxazepine derivative and its preparation |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4435391A (en]) |
| EP (1) | EP0040860B1 (en]) |
| JP (1) | JPS56166180A (en]) |
| KR (1) | KR850000212B1 (en]) |
| AT (1) | ATE6645T1 (en]) |
| CA (1) | CA1162189A (en]) |
| DE (1) | DE3162614D1 (en]) |
| HU (1) | HU183456B (en]) |
| IL (1) | IL62894A (en]) |
| MX (1) | MX157054A (en]) |
| ZA (1) | ZA813385B (en]) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0240721A3 (en) * | 1986-03-12 | 1991-01-02 | Chugai Seiyaku Kabushiki Kaisha | Therapeutic agent for the treatment of peripheral circulatory disorders |
| DK0805155T3 (da) * | 1994-09-28 | 2002-07-08 | Nippon Suisan Kaisha Ltd | Hidtil ukendt tricyklisk, kondenseret heterocyklisk antioxidantforbindelse |
| WO1996033983A1 (fr) * | 1995-04-25 | 1996-10-31 | Daiichi Radioisotope Laboratories, Ltd. | Derives n-oxyde de dibenzoxazepine et medicament les contenant en tant que principe actif |
| JP4582366B2 (ja) * | 1998-11-30 | 2010-11-17 | 東レ・ファインケミカル株式会社 | ピロリジン誘導体の製造法 |
| US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| KR20070100894A (ko) * | 2005-01-19 | 2007-10-12 | 브리스톨-마이어스 스큅 컴퍼니 | 혈전색전성 장애 치료용 ｐ2ｙ1 수용체 억제제로서의2-페녹시-ｎ-(1,3,4-티아디졸-2-일)피리딘-3-아민 유도체및 관련 화합물 |
| DE602006021306D1 (en]) * | 2005-06-27 | 2011-05-26 | Bristol Myers Squibb Co | |
| ES2360818T3 (es) * | 2005-06-27 | 2011-06-09 | Bristol-Myers Squibb Company | Miméticos de urea lineal antagonistas del receptor p2y, útiles en el tratamiento de afecciones trombóticas. |
| WO2007002634A1 (en) * | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| ATE485269T1 (de) * | 2005-06-27 | 2010-11-15 | Bristol Myers Squibb Co | C-verknüpfte zyklische antagonisten des p2y1- rezeptors mit eignung bei der behandlung thrombotischer leiden |
| WO2007047737A1 (en) * | 2005-10-17 | 2007-04-26 | Acadia Pharmaceuticals Inc. | Cb-1 modulating compounds and their use |
| US20080090805A1 (en) * | 2005-10-17 | 2008-04-17 | Acadia Pharmaceuticals Inc. | Cb-1 modulating compounds and their use |
| US7960569B2 (en) * | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| CN101889000B (zh) * | 2007-12-05 | 2012-11-28 | 詹森药业有限公司 | 二苯并氮杂*和二苯并氧氮杂*trpa1激动剂 |
| WO2019173761A1 (en) * | 2018-03-09 | 2019-09-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | C-abl tyrosine kinase inhibitory compound embodiments and methods of making and using the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH473141A (de) | 1965-12-30 | 1969-05-31 | Wander Ag Dr A | Verfahren zur Herstellung 11-aminoalkylierter Dibenz(b,f)-1,4-oxazepine und Dibenzo(b,f)-1,4-thiazepine |
| US3646009A (en) | 1967-03-15 | 1972-02-29 | Boehringer & Soehne Gmbh | Anti-diabetically active sulfonyl-semicarbazides |
| US3458516A (en) | 1968-02-16 | 1969-07-29 | American Cyanamid Co | 11-(piperazinyl)dibenz(b,f)(1,4)oxazepines and analogous thiazepines |
| DE2014223A1 (de) | 1969-03-28 | 1970-10-01 | Sumitomo Chemical Company Ltd., Osaka (Japan) | Benzoxazepin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JPS5576869A (en) * | 1978-12-06 | 1980-06-10 | Chugai Pharmaceut Co Ltd | Dibenzoxazepine derivative and its preparation |
-
1980
- 1980-05-28 JP JP7017680A patent/JPS56166180A/ja active Granted
-
1981
- 1981-05-18 IL IL62894A patent/IL62894A/xx unknown
- 1981-05-20 ZA ZA00813385A patent/ZA813385B/xx unknown
- 1981-05-23 KR KR1019810001793A patent/KR850000212B1/ko not_active Expired
- 1981-05-27 CA CA000378457A patent/CA1162189A/en not_active Expired
- 1981-05-27 EP EP81104100A patent/EP0040860B1/en not_active Expired
- 1981-05-27 HU HU811589A patent/HU183456B/hu not_active IP Right Cessation
- 1981-05-27 AT AT81104100T patent/ATE6645T1/de not_active IP Right Cessation
- 1981-05-27 DE DE8181104100T patent/DE3162614D1/de not_active Expired
- 1981-05-28 MX MX187533A patent/MX157054A/es unknown
-
1982
- 1982-03-04 US US06/354,651 patent/US4435391A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0040860B1 (en) | 1984-03-14 |
| IL62894A0 (en) | 1981-07-31 |
| CA1162189A (en) | 1984-02-14 |
| JPS56166180A (en) | 1981-12-21 |
| KR830006249A (ko) | 1983-09-20 |
| US4435391A (en) | 1984-03-06 |
| IL62894A (en) | 1984-10-31 |
| MX157054A (es) | 1988-10-24 |
| ZA813385B (en) | 1982-06-30 |
| HU183456B (en) | 1984-05-28 |
| DE3162614D1 (en) | 1984-04-19 |
| KR850000212B1 (ko) | 1985-03-06 |
| EP0040860A1 (en) | 1981-12-02 |
| ATE6645T1 (de) | 1984-03-15 |
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