GB1538775A - Preparation of 6,11-dihydro-11-oxodibenz(b,e)-oxepin-alkanoic acids - Google Patents
Preparation of 6,11-dihydro-11-oxodibenz(b,e)-oxepin-alkanoic acidsInfo
- Publication number
- GB1538775A GB1538775A GB1181/76A GB118176A GB1538775A GB 1538775 A GB1538775 A GB 1538775A GB 1181/76 A GB1181/76 A GB 1181/76A GB 118176 A GB118176 A GB 118176A GB 1538775 A GB1538775 A GB 1538775A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- oxodibenz
- dihydro
- compounds
- oxepin
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- -1 dicarbonyl halides Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 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
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
6,11-Dihydro-11-oxodibenz[b,e]oxepinealkanoic acids of the formula I are prepared from dicarbonyl halides of the formula II which are converted into oxepinealkanoyl halides which are then hydrolysed to compounds of the formula I. The symbols in the formulae have the meaning stated in Claim 1. The reaction is carried out either with a Lewis acid in the presence of solvents at 0 DEG C to room temperature or in the presence of iron chloride without solvent at temperatures from 100 to 150 DEG C. The compounds of the formula II can be prepared by treating the corresponding dicarboxylic acid with a mixture of thionyl chloride and iron chloride at room temperature to the boiling point of the reaction mixture. The compounds of the formula I have anti-inflammatory and analgesic effects. <IMAGE>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54096375A | 1975-01-14 | 1975-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1538775A true GB1538775A (en) | 1979-01-24 |
Family
ID=24157637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1181/76A Expired GB1538775A (en) | 1975-01-14 | 1976-01-13 | Preparation of 6,11-dihydro-11-oxodibenz(b,e)-oxepin-alkanoic acids |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5195085A (en) |
| AT (1) | AT362376B (en) |
| BE (1) | BE837561A (en) |
| CA (1) | CA1081240A (en) |
| CH (1) | CH627464A5 (en) |
| CS (2) | CS190509B2 (en) |
| DK (1) | DK12376A (en) |
| ES (1) | ES444144A1 (en) |
| FI (1) | FI760052A7 (en) |
| FR (1) | FR2297852A1 (en) |
| GB (1) | GB1538775A (en) |
| HU (1) | HU175610B (en) |
| IE (1) | IE41999B1 (en) |
| IT (1) | IT1054782B (en) |
| LU (1) | LU74174A1 (en) |
| MX (1) | MX3745E (en) |
| NL (1) | NL7600204A (en) |
| NO (2) | NO149387C (en) |
| PT (1) | PT64691B (en) |
| SE (1) | SE422796B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037254A1 (en) * | 1980-03-31 | 1981-10-07 | Dainippon Pharmaceutical Co., Ltd. | Acetic acid derivatives, process for the preparation thereof and composition containing the same |
| US4515946A (en) * | 1981-12-23 | 1985-05-07 | Hoechst-Roussel Pharmaceuticals Inc. | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives |
| US4526891A (en) * | 1983-03-10 | 1985-07-02 | Hoechst Roussel Pharmaceuticals Inc. | Substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins |
| US4576960A (en) * | 1981-12-23 | 1986-03-18 | Hoechst Roussel Pharmaceuticals Incorporated | 6,11-Dihydro-11-oxo-dibenz[b,e]oxepin derivatives |
| WO2003082802A1 (en) * | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1279682B (en) * | 1961-08-12 | 1968-10-10 | Boehringer & Soehne Gmbh | Process for the preparation of 6, 11-dihydro-dibenzo- [b, e] -oxepin- or -thiepin-11-one |
| DE1294970B (en) * | 1961-09-28 | 1969-05-14 | Boehringer & Soehne Gmbh | Process for the preparation of substituted 6, 11-dihydrodibenzo [b, e] -oxepin- or -thiepin-11-ones |
| FR1449569A (en) * | 1961-10-07 | 1966-05-06 | Boehringer & Soehne Gmbh | Process for the preparation of basic derivatives of dibenzo-oxepin and dibenzo-thiepin, their salts and their quaternary ammonium compounds |
| YU204274A (en) * | 1973-07-24 | 1982-06-30 | Hoechst Ag | Process for preparing new dibenzoxepin derivatives |
-
1976
- 1976-01-08 ES ES444144A patent/ES444144A1/en not_active Expired
- 1976-01-09 NL NL7600204A patent/NL7600204A/en not_active Application Discontinuation
- 1976-01-12 FI FI760052A patent/FI760052A7/fi not_active Application Discontinuation
- 1976-01-12 IT IT19179/76A patent/IT1054782B/en active
- 1976-01-13 CS CS76222A patent/CS190509B2/en unknown
- 1976-01-13 CS CS777409A patent/CS190550B2/en unknown
- 1976-01-13 CH CH33876A patent/CH627464A5/en not_active IP Right Cessation
- 1976-01-13 LU LU74174A patent/LU74174A1/xx unknown
- 1976-01-13 AT AT17476A patent/AT362376B/en not_active IP Right Cessation
- 1976-01-13 GB GB1181/76A patent/GB1538775A/en not_active Expired
- 1976-01-13 DK DK12376*#A patent/DK12376A/en not_active Application Discontinuation
- 1976-01-13 HU HU76HO1871A patent/HU175610B/en unknown
- 1976-01-13 IE IE54/76A patent/IE41999B1/en unknown
- 1976-01-13 PT PT64691A patent/PT64691B/en unknown
- 1976-01-13 NO NO760101A patent/NO149387C/en unknown
- 1976-01-13 CA CA243,400A patent/CA1081240A/en not_active Expired
- 1976-01-14 JP JP51003719A patent/JPS5195085A/en active Pending
- 1976-01-14 SE SE7600321A patent/SE422796B/en unknown
- 1976-01-14 FR FR7600784A patent/FR2297852A1/en active Granted
- 1976-01-14 MX MX762392U patent/MX3745E/en unknown
- 1976-01-14 BE BE163509A patent/BE837561A/en not_active IP Right Cessation
-
1981
- 1981-04-24 NO NO811390A patent/NO150157C/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037254A1 (en) * | 1980-03-31 | 1981-10-07 | Dainippon Pharmaceutical Co., Ltd. | Acetic acid derivatives, process for the preparation thereof and composition containing the same |
| US4515946A (en) * | 1981-12-23 | 1985-05-07 | Hoechst-Roussel Pharmaceuticals Inc. | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives |
| US4576960A (en) * | 1981-12-23 | 1986-03-18 | Hoechst Roussel Pharmaceuticals Incorporated | 6,11-Dihydro-11-oxo-dibenz[b,e]oxepin derivatives |
| US4526891A (en) * | 1983-03-10 | 1985-07-02 | Hoechst Roussel Pharmaceuticals Inc. | Substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins |
| WO2003082802A1 (en) * | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
| US7560586B2 (en) | 2002-03-27 | 2009-07-14 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CS190550B2 (en) | 1979-05-31 |
| DK12376A (en) | 1976-07-15 |
| LU74174A1 (en) | 1976-12-31 |
| IE41999L (en) | 1976-07-14 |
| NO149387C (en) | 1984-04-11 |
| AT362376B (en) | 1981-05-11 |
| JPS5195085A (en) | 1976-08-20 |
| FI760052A7 (en) | 1976-07-15 |
| NO150157C (en) | 1984-08-29 |
| PT64691A (en) | 1976-05-01 |
| SE7600321L (en) | 1976-07-15 |
| FR2297852A1 (en) | 1976-08-13 |
| CS190509B2 (en) | 1979-05-31 |
| ATA17476A (en) | 1980-10-15 |
| NO149387B (en) | 1984-01-02 |
| MX3745E (en) | 1981-06-11 |
| BE837561A (en) | 1976-07-14 |
| NO150157B (en) | 1984-05-21 |
| NO760101L (en) | 1976-07-15 |
| FR2297852B1 (en) | 1979-08-31 |
| CH627464A5 (en) | 1982-01-15 |
| IT1054782B (en) | 1981-11-30 |
| IE41999B1 (en) | 1980-05-07 |
| CA1081240A (en) | 1980-07-08 |
| PT64691B (en) | 1977-08-09 |
| ES444144A1 (en) | 1977-08-16 |
| NL7600204A (en) | 1976-07-16 |
| NO811390L (en) | 1976-07-15 |
| HU175610B (en) | 1980-09-28 |
| SE422796B (en) | 1982-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |