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 properties

Info

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
Application number
CH921275A
Inventor
Takehiro Amano
Teruya Seki
Michitada Sasajima
Original Assignee
Taisho Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Publication of CH610582A5 publication Critical patent/CH610582A5/en

Links

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.
CH921275A 1974-07-16 1975-07-15 Process for the preparation of a stilbene derivative having analgesic and anti-inflammatory properties CH610582A5 (en)

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)

* Cited by examiner, † Cited by third party
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

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