IE43705B1 - Benzofuranone derivative - Google Patents
Benzofuranone derivativeInfo
- Publication number
- IE43705B1 IE43705B1 IE2465/80A IE246580A IE43705B1 IE 43705 B1 IE43705 B1 IE 43705B1 IE 2465/80 A IE2465/80 A IE 2465/80A IE 246580 A IE246580 A IE 246580A IE 43705 B1 IE43705 B1 IE 43705B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- stated
- benzofuranone derivative
- accordance
- Prior art date
Links
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
The preseht invention relates to a benzofuranone derivatives in particular the compound of formula I, which is 5-ch1oro-6-cyclohexyl-2,3-dihydrobenzo-furan-2-one.
Further, in accordance with the invention, the compound of formula I may be obtained by a process comprising lactonizing a compound of formula II, - 2 4370» The lactonization of the compound of formula II in accordance with the process of the invention is effected in accordance with conventional methods, as described in the Example.
The compound of formula II may be obtained in accordance with known methods.
The compound of formula I exhibits pharmacological activity. In particular, the compound exhibits oedema and inflammation inhibiting activity, as indicated in standard tests, for example in the carrageen oedema test, in the Adjuvans arthritis test and the granuloma cyst test in the rat and in the UV erythma test in the guinea-pig.
In standard tests, the compound of formula I exhibits further effects, such as an anti-pyretic effect, an analgesic effect, or an inhibition of PG synthetase or of collagen-induced blood platelet aggregation.
The compound is therefore indicated for use as an inhibitor of oedemas and inflammations. An indicated daily does is from 60 to 300 mg, conveniently administered in divided doses 2 to 4 times a day in unit dosage form containing from 15 to 150 mg of the compound, or in sustained release form.
The present invention also provides a pharmaceutical composition comprising a compound of formula I, in association with a pharmaceutical carrier or diluent. Such compositions may be in the form of, for example, a solution or a tablet.
The compound may be prepared as in the following Example in which all temperatures are indicated in degrees Celcius.
The compound of formula II is described and claimed in our British Patent Specification No. 1,546,703.
EXAMPLE.
-Chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one g of 3'-chloro-4'-cyclohexyl-6'-hydroxyphenylacetic acid are dissolved in toluene with heating, 50 mg of p-tol uenesul phonic acid are added, and the mixture is boiled in a water separator for 3 hours. The oil obtained - 3 4370S after evaporation is purified on a 100-fold quantity of silica gel Merck (Registered Trade Mark). The desired product is eluted with chloroform and recrystallized from methylene.chloride/petroleum ether. The crystals have an M.P. of 100-102°.
Claims (5)
1. A process for the production of a compound of formula I,
2. A process for the production of the compound of formula I, as stated in Claim 1, substantially as hereinbefore described with reference to the Example.
3. The compound of formula I, as stated in Claim 1, whenever produced by a process according to Claim 1 or 2.
4. The compound of Claim 1, as stated in Claim 1.
5. A pharmaceutical composition comprising the compound according to Claim 3 or 4, in association with a pharmaceutically acceptable diluent or carrier.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312975A CH614707A5 (en) | 1975-03-12 | 1975-03-12 | Process for the preparation of novel dihydrobenzofuranone derivatives |
| CH967875 | 1975-07-24 | ||
| IE501/76A IE43704B1 (en) | 1975-03-12 | 1976-03-10 | Benzofuranone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43705L IE43705L (en) | 1976-09-12 |
| IE43705B1 true IE43705B1 (en) | 1981-05-06 |
Family
ID=27174148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2465/80A IE43705B1 (en) | 1975-03-12 | 1976-03-10 | Benzofuranone derivative |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IE43705B1 (en) |
-
1976
- 1976-03-10 IE IE2465/80A patent/IE43705B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE43705L (en) | 1976-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2951082A (en) | Substituted thiaxanthenes | |
| AU584153B2 (en) | Naphthalene derivatives and processes of preparation thereof | |
| EP0047536B1 (en) | Substituted propylamines | |
| GB1511463A (en) | 1-acylamino methyl-1,2,3,4-tetrahydroisoquinolines | |
| ES8504682A1 (en) | New nitro aliphatic compounds, process for preparation thereof and use thereof. | |
| IL33846A (en) | Derivatives of 1-thiachromone and 4-thionchromone,their preparation and pharmaceutical compositions containing them | |
| US4092430A (en) | Antiphlogistic phenylacetohydroxamic acid compositions | |
| IE43705B1 (en) | Benzofuranone derivative | |
| EP0564648B1 (en) | Aconitine compound and analgesic/antiinflammatory agent | |
| US3833610A (en) | 3,5-dioxo-2,3,5,6-tetrahydro-(4h)-pyrane and thiopyrane-4-carboxanilides | |
| US2954400A (en) | alpha-indanoxybutyric acid derivatives | |
| US3781415A (en) | Product,process and composition | |
| JPS60104084A (en) | 4h-benzo(4,5)cyclohepta(1,2-b)thiophene derivative | |
| US3712946A (en) | Certain oxy-substituted benzo quinolizinium compounds and their use | |
| US3322778A (en) | Novel ether derivatives of benzmorphans | |
| US3181994A (en) | Analgesic biphenyl acetic acid derivatives | |
| US3826839A (en) | Anti-arthritic compositions comprising ester derivatives of pulvinic acid and methods of producing anti-arthritic activity | |
| IE33870B1 (en) | Benzobenzofuranooxepine compounds and process for preparing the same | |
| SU1072809A3 (en) | Process for preparing thiadiazoletetrahydroisoquinonoline or its pharmaceutically acceptable acid addition salts | |
| US3269909A (en) | Analgesic methods and compositions of benzoic acid derivatives | |
| GB2202532A (en) | 4-benzylthiophene(or furan)-2-sulfonamides as antiglaucoma agents | |
| US3862936A (en) | Mannich derivatives of 4,4{40 -dihydroxy-3,3{40 dinitrobenzophenone | |
| US3821408A (en) | Compositions of sulfonium ylides and method of use | |
| US3534050A (en) | 4-oxazolidones having cyclic fluoroalkylene substituents in the 2- and 5-positions | |
| IE43704B1 (en) | Benzofuranone compounds |