CH610582A5 - Process for the preparation of a stilbene derivative having analgesic and anti-inflammatory properties - Google Patents
Process for the preparation of a stilbene derivative having analgesic and anti-inflammatory propertiesInfo
- Publication number
- CH610582A5 CH610582A5 CH921275A CH921275A CH610582A5 CH 610582 A5 CH610582 A5 CH 610582A5 CH 921275 A CH921275 A CH 921275A CH 921275 A CH921275 A CH 921275A CH 610582 A5 CH610582 A5 CH 610582A5
- Authority
- CH
- Switzerland
- Prior art keywords
- analgesic
- preparation
- ibuprofen
- inflammatory properties
- approximately
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract 3
- 230000000202 analgesic effect Effects 0.000 title abstract 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229960001680 ibuprofen Drugs 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241000699670 Mus sp. Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Stilbene derivatives having the formula <IMAGE> where R1 and R2 are independently hydrogen or a lower alkyl, lower alkoxy, halo or haloalkyl group and R3 is hydrogen or a lower alkyl group, are prepared by hydrolysis of a compound represented by the general formula <IMAGE> where M is -HC(R3)CN, -CH2C(S)B where B is the amino group or -HC(R3)COOA where A is an alkyl group, in water, an organic solvent or their mixture, in the presence of an acid or an alkali. The compounds thus prepared have excellent analgesic and anti-inflammatory activity and their toxicity is extremely low. In particular, 2-(3-stilbene)propionic acid is approximately 1.5 times more effective than ibuprofen, as regards the anti-inflammatory and analgesic activity and its oral LD50 value in mice is 2152 mg/kg, that is to say approximately two times more than in the case of ibuprofen.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP49081299A JPS5111748A (en) | 1974-07-16 | 1974-07-16 | Suchirubenjudotaino seizoho |
Publications (1)
Publication Number | Publication Date |
---|---|
CH610582A5 true CH610582A5 (en) | 1979-04-30 |
Family
ID=13742501
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH921275A CH610582A5 (en) | 1974-07-16 | 1975-07-15 | Process for the preparation of a stilbene derivative having analgesic and anti-inflammatory properties |
Country Status (12)
Country | Link |
---|---|
JP (1) | JPS5111748A (en) |
AR (1) | AR205387A1 (en) |
AU (1) | AU470771B2 (en) |
CA (1) | CA1053257A (en) |
CH (1) | CH610582A5 (en) |
DE (1) | DE2531456A1 (en) |
ES (1) | ES439430A1 (en) |
FR (1) | FR2278332A1 (en) |
GB (1) | GB1465661A (en) |
NL (1) | NL7507803A (en) |
PH (1) | PH11312A (en) |
SE (1) | SE409452B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2832213A1 (en) * | 1978-07-21 | 1980-01-31 | Bayer Ag | STILEN DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS INSECTICIDES |
DE2944428C2 (en) * | 1979-11-03 | 1984-08-30 | Trützschler GmbH & Co KG, 4050 Mönchengladbach | Device for production control and sliver regulation of a card |
FR2492815A1 (en) * | 1980-10-23 | 1982-04-30 | Sori Soc Rech Ind | NEW CINNAMOYL-CINNAMIC ACID DERIVATIVE, PREPARATION METHOD AND THERAPEUTIC APPLICATION THEREOF |
SE8400239D0 (en) * | 1984-01-19 | 1984-01-19 | Pharmacia Ab | NEW ARYLETIC ACID DERIVATIVES |
CH659814A5 (en) * | 1984-03-27 | 1987-02-27 | Ciba Geigy Ag | STYLE DERIVATIVES. |
TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
US7321050B2 (en) | 1999-12-06 | 2008-01-22 | Welichem Biotech Inc. | Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxy stilbenes and novel stilbene derivatives and analogues |
CN1319959C (en) * | 1999-12-06 | 2007-06-06 | 天济药业(深圳)有限公司 | Polyhydroxystilbenes and stibene oxides as antisoriatic agents and protein kinase inhibitors |
ITMI20012434A1 (en) * | 2001-11-20 | 2003-05-20 | Dompe Spa | 2-ARYL-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
AU2016263161B2 (en) | 2015-05-21 | 2019-02-28 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
MX2020004785A (en) | 2017-11-10 | 2020-08-13 | Dermavant Sciences GmbH | Process for preparing tapinarof. |
US11497718B2 (en) | 2018-11-13 | 2022-11-15 | Dermavant Sciences GmbH | Use of tapinarof for the treatment of atopic dermatitis |
-
1974
- 1974-07-16 JP JP49081299A patent/JPS5111748A/en active Granted
-
1975
- 1975-01-01 AR AR259394A patent/AR205387A1/en active
- 1975-06-13 GB GB2539075A patent/GB1465661A/en not_active Expired
- 1975-06-17 AU AU82152/75A patent/AU470771B2/en not_active Expired
- 1975-06-26 PH PH17515A patent/PH11312A/en unknown
- 1975-07-01 NL NL7507803A patent/NL7507803A/en not_active Application Discontinuation
- 1975-07-14 DE DE19752531456 patent/DE2531456A1/en not_active Withdrawn
- 1975-07-15 CH CH921275A patent/CH610582A5/en not_active IP Right Cessation
- 1975-07-15 SE SE7508074A patent/SE409452B/en unknown
- 1975-07-15 CA CA231,559A patent/CA1053257A/en not_active Expired
- 1975-07-15 ES ES439430A patent/ES439430A1/en not_active Expired
- 1975-07-15 FR FR7522113A patent/FR2278332A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
DE2531456A1 (en) | 1976-02-05 |
AR205387A1 (en) | 1976-04-30 |
SE7508074L (en) | 1976-01-19 |
ES439430A1 (en) | 1977-02-01 |
AU470771B2 (en) | 1976-03-25 |
NL7507803A (en) | 1976-01-20 |
GB1465661A (en) | 1977-02-23 |
FR2278332B1 (en) | 1980-05-16 |
CA1053257A (en) | 1979-04-24 |
PH11312A (en) | 1977-11-02 |
AU8215275A (en) | 1976-03-25 |
JPS5111748A (en) | 1976-01-30 |
FR2278332A1 (en) | 1976-02-13 |
SE409452B (en) | 1979-08-20 |
JPS5227B2 (en) | 1977-01-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |