CA1236833A - 2h-[1]benzoxepino[5,4-b]1,4-oxazine derivatives - Google Patents
2h-[1]benzoxepino[5,4-b]1,4-oxazine derivativesInfo
- Publication number
- CA1236833A CA1236833A CA000447245A CA447245A CA1236833A CA 1236833 A CA1236833 A CA 1236833A CA 000447245 A CA000447245 A CA 000447245A CA 447245 A CA447245 A CA 447245A CA 1236833 A CA1236833 A CA 1236833A
- Authority
- CA
- Canada
- Prior art keywords
- oxazine
- hydrogen
- benzoxepino
- hexahydro
- methoxy
- 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
- IHKALFITVBQHPG-UHFFFAOYSA-N 2h-[1]benzoxepino[5,4-b][1,4]oxazine Chemical class C1=COC2=CC=CC=C2C2=C1N=CCO2 IHKALFITVBQHPG-UHFFFAOYSA-N 0.000 title claims abstract 4
- -1 trans-(4a Chemical class 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 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 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 11
- 235000013350 formula milk Nutrition 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 6
- YRMMRFYPKHSIDT-PSASIEDQSA-N (4r,5r)-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol Chemical compound O[C@H]1[C@H](N)CCOC2=CC=CC=C21 YRMMRFYPKHSIDT-PSASIEDQSA-N 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 36
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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- YRMMRFYPKHSIDT-UHFFFAOYSA-N 4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol Chemical class OC1C(N)CCOC2=CC=CC=C21 YRMMRFYPKHSIDT-UHFFFAOYSA-N 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 description 3
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- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
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- TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical class CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 description 2
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- ADUJEROBDBLDMY-MWLCHTKSSA-N (4r,5r)-4-amino-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepin-5-ol Chemical compound O1CC[C@@H](N)[C@H](O)C2=CC(OC)=CC=C21 ADUJEROBDBLDMY-MWLCHTKSSA-N 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46640783A | 1983-02-15 | 1983-02-15 | |
| US466,407 | 1983-02-15 | ||
| US56275983A | 1983-12-21 | 1983-12-21 | |
| US562,759 | 1983-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236833A true CA1236833A (en) | 1988-05-17 |
Family
ID=27041648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000447245A Expired CA1236833A (en) | 1983-02-15 | 1984-02-13 | 2h-[1]benzoxepino[5,4-b]1,4-oxazine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0116373B1 (en, 2012) |
| KR (1) | KR900005471B1 (en, 2012) |
| AU (1) | AU561700B2 (en, 2012) |
| CA (1) | CA1236833A (en, 2012) |
| DE (1) | DE3463142D1 (en, 2012) |
| DK (1) | DK158986C (en, 2012) |
| ES (1) | ES529720A0 (en, 2012) |
| GR (1) | GR81510B (en, 2012) |
| IE (1) | IE56788B1 (en, 2012) |
| IL (1) | IL70941A (en, 2012) |
| NO (1) | NO167571C (en, 2012) |
| NZ (1) | NZ207110A (en, 2012) |
| PH (1) | PH22343A (en, 2012) |
| PT (1) | PT78109B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE939614C (de) * | 1949-02-26 | 1956-02-23 | Ernst Rodenhaeuser | Kolbendichtung fuer Kolbenfuellhalter |
| NZ207111A (en) * | 1983-02-15 | 1986-07-11 | Merrell Dow Pharma | (4a,11b)-3,4,4a,5,6,11b-hexahydro-2h-(1)benzoxepino(5,4-b)-1,4 oxazine derivatives and pharmaceutical compositions |
| US4766212A (en) * | 1983-02-15 | 1988-08-23 | Merrell Dow Pharmaceuticals Inc. | 2H-[1]benzoxepino[5,4-b]-1,4-oxazine derivatives |
| FR2698873B1 (fr) * | 1992-12-07 | 1995-02-24 | Lipha | Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant. |
| WO2011146821A2 (en) | 2010-05-21 | 2011-11-24 | Research Triangle Institute | 1 - phenylmorpholine derivatives as hydroxybupropion analogues for treating drug dependence |
| ES2687095T3 (es) | 2010-05-21 | 2018-10-23 | Research Triangle Institute | Fenilimorfolinas y análogos de las mismas |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593760A1 (de) * | 1967-02-01 | 1972-06-08 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer Benz-epinderivate |
-
1984
- 1984-02-10 PH PH30228A patent/PH22343A/en unknown
- 1984-02-10 NZ NZ207110A patent/NZ207110A/en unknown
- 1984-02-13 CA CA000447245A patent/CA1236833A/en not_active Expired
- 1984-02-13 GR GR73786A patent/GR81510B/el unknown
- 1984-02-13 IL IL70941A patent/IL70941A/xx not_active IP Right Cessation
- 1984-02-13 AU AU24542/84A patent/AU561700B2/en not_active Ceased
- 1984-02-14 DE DE8484101520T patent/DE3463142D1/de not_active Expired
- 1984-02-14 KR KR1019840000692A patent/KR900005471B1/ko not_active Expired
- 1984-02-14 IE IE334/84A patent/IE56788B1/en not_active IP Right Cessation
- 1984-02-14 DK DK066284A patent/DK158986C/da active
- 1984-02-14 ES ES529720A patent/ES529720A0/es active Granted
- 1984-02-14 NO NO840534A patent/NO167571C/no unknown
- 1984-02-14 EP EP84101520A patent/EP0116373B1/en not_active Expired
- 1984-02-15 PT PT78109A patent/PT78109B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO840534L (no) | 1984-08-16 |
| ES8600301A1 (es) | 1985-10-01 |
| IE56788B1 (en) | 1991-12-18 |
| DK66284A (da) | 1984-08-16 |
| AU2454284A (en) | 1984-08-23 |
| PH22343A (en) | 1988-08-12 |
| PT78109B (en) | 1986-05-20 |
| IL70941A0 (en) | 1984-05-31 |
| DK158986B (da) | 1990-08-13 |
| NO167571C (no) | 1991-11-20 |
| IL70941A (en) | 1987-12-31 |
| EP0116373B1 (en) | 1987-04-15 |
| AU561700B2 (en) | 1987-05-14 |
| GR81510B (en, 2012) | 1984-12-11 |
| DE3463142D1 (de) | 1987-05-21 |
| PT78109A (en) | 1984-03-01 |
| NO167571B (no) | 1991-08-12 |
| KR840007729A (ko) | 1984-12-10 |
| KR900005471B1 (ko) | 1990-07-30 |
| ES529720A0 (es) | 1985-10-01 |
| DK66284D0 (da) | 1984-02-14 |
| IE840334L (en) | 1984-08-15 |
| DK158986C (da) | 1991-01-07 |
| NZ207110A (en) | 1986-05-09 |
| EP0116373A1 (en) | 1984-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20050517 |