GB1465661A - Stilbene derivatives - Google Patents
Stilbene derivativesInfo
- Publication number
- GB1465661A GB1465661A GB2539075A GB2539075A GB1465661A GB 1465661 A GB1465661 A GB 1465661A GB 2539075 A GB2539075 A GB 2539075A GB 2539075 A GB2539075 A GB 2539075A GB 1465661 A GB1465661 A GB 1465661A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- prepared
- alkyl
- viii
- hydrolysis
- 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 238000006458 Meerwein arylation reaction Methods 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- NHWBURSWXLANJN-UHFFFAOYSA-N 2-[3-(2-phenylethenyl)phenyl]acetic acid Chemical class OC(=O)CC1=CC=CC(C=CC=2C=CC=CC=2)=C1 NHWBURSWXLANJN-UHFFFAOYSA-N 0.000 abstract 1
- FVPDFMQEJQMDQG-UHFFFAOYSA-N 2-[3-(2-phenylethenyl)phenyl]propanedioic acid Chemical compound C(=CC1=CC=CC=C1)C=1C=C(C=CC1)C(C(=O)O)C(=O)O FVPDFMQEJQMDQG-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- -1 alkyl 3-stilbeneacetate Chemical compound 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 238000007098 aminolysis reaction Methods 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 238000007333 cyanation reaction Methods 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
1465661 Stilbene derivatives TAISHO PHARMACEUTICAL CO Ltd 13 June 1975 [16 July 1974] 25390/75 Heading C2C Novel compounds I in which each of R 1 and R 2 is H, C 1-5 alkyl, C 1-5 alkoxy, halogen or C 1-5 haloalkyl and each of R 3 and R 4 is H or C 1-5 alkyl, and salts thereof, are prepared by hydrolysis of a compound II or III in which B is amino, preferably, cyclic amino, or hydrolysis and decarboxylation of a compound IV in which R 3 is C 1-5 alkyl and A is alkyl, followed, if desired, by esterification of the free acid or an anhydride or halide derivative thereof. The esters in which R 3 is C 1-5 alkyl may also be prepared by alkylation of 3-stilbeneacetic acid esters. The salts are prepared in known manner. Compounds II are prepared by cyanation of compounds V which are themselves prepared by halogenation of compounds VI or VII Compounds II may also be prepared by a Meerwein arylation followed by an optional alkylation step. Compounds VII are prepared by reduction of compounds VIII. Compounds VI and VIII are prepared by means of a Meerwein arylation process. Compounds III are prepared from compounds VIII by a Willgerodt reaction. Compounds IV are prepared by reacting an appropriate alkyl 3-stilbeneacetate with a dialkylcarbonate and alkylating the resulting dialkyl 3-styrylphenylmalonate. Pharmaceutical compositions having analgesic and anti-inflammatory activity comprise one of the above novel compounds together with a pharmaceutical carrier.
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 |
|---|---|
| GB1465661A true GB1465661A (en) | 1977-02-23 |
Family
ID=13742501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2539075A Expired GB1465661A (en) | 1974-07-16 | 1975-06-13 | Stilbene derivatives |
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) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4684744A (en) * | 1984-03-27 | 1987-08-04 | Ciga-Geiby Corporation | Stilbene derivatives |
| EP0150166B1 (en) * | 1984-01-19 | 1988-07-20 | Pharmacia Ab | Novel arylacitic acid derivatives |
| WO2001042231A2 (en) * | 1999-12-06 | 2001-06-14 | Welichem Biotech Inc. | Polyhydroxystilbenes and stilbene oxides as antisoriatic agents and protein kinase inhibitors |
| EP1216980A1 (en) * | 1999-10-01 | 2002-06-26 | Eisai Co., Ltd. | Carboxylic acid derivatives and drugs containing the same |
| WO2003043625A1 (en) * | 2001-11-20 | 2003-05-30 | Dompe S.P.A. | 2-aryl-propionic acids and pharmaceutical compositions containing them |
| 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 |
| US10426743B2 (en) | 2015-05-21 | 2019-10-01 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US10647649B2 (en) | 2017-11-10 | 2020-05-12 | 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 |
| US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
Families Citing this family (3)
| 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 |
-
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
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0150166B1 (en) * | 1984-01-19 | 1988-07-20 | Pharmacia Ab | Novel arylacitic acid derivatives |
| US4684744A (en) * | 1984-03-27 | 1987-08-04 | Ciga-Geiby Corporation | Stilbene derivatives |
| EP1216980A1 (en) * | 1999-10-01 | 2002-06-26 | Eisai Co., Ltd. | Carboxylic acid derivatives and drugs containing the same |
| EP1216980A4 (en) * | 1999-10-01 | 2010-12-08 | Eisai R&D Man Co Ltd | Carboxylic acid derivatives and drugs containing the same |
| WO2001042231A2 (en) * | 1999-12-06 | 2001-06-14 | Welichem Biotech Inc. | Polyhydroxystilbenes and stilbene oxides as antisoriatic agents and protein kinase inhibitors |
| WO2001042231A3 (en) * | 1999-12-06 | 2001-11-01 | Welichem Biotech Inc | Polyhydroxystilbenes and stilbene oxides as antisoriatic agents and protein kinase inhibitors |
| 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 |
| WO2003043625A1 (en) * | 2001-11-20 | 2003-05-30 | Dompe S.P.A. | 2-aryl-propionic acids and pharmaceutical compositions containing them |
| AU2002352052B2 (en) * | 2001-11-20 | 2008-09-04 | Dompe' Farmaceutici S.P.A. | 2-Aryl-propionic acids and pharmaceutical compositions containing them |
| US8063242B2 (en) | 2001-11-20 | 2011-11-22 | Dompe Pha.R.Ma S.P.A. | 2-aryl-propionic acids and pharmaceutical compositions containing them |
| US10426743B2 (en) | 2015-05-21 | 2019-10-01 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US11458108B2 (en) | 2015-05-21 | 2022-10-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US11612573B2 (en) | 2015-05-21 | 2023-03-28 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US11622945B2 (en) | 2015-05-21 | 2023-04-11 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
| US10647649B2 (en) | 2017-11-10 | 2020-05-12 | Dermavant Sciences GmbH | Process for preparing tapinarof |
| US10961175B2 (en) | 2017-11-10 | 2021-03-30 | Dermavant Sciences GmbH | Process for preparing tapinarof |
| US11597692B2 (en) | 2017-11-10 | 2023-03-07 | 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 |
| US11590088B2 (en) | 2018-11-13 | 2023-02-28 | Dermavant Sciences GmbH | Use of Tapinarof for the treatment of chronic plaque psoriasis |
| US11938099B2 (en) | 2018-11-13 | 2024-03-26 | Dermavant Sciences GmbH | Use of tapinarof for the treatment of atopic dermatitis |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2531456A1 (en) | 1976-02-05 |
| CH610582A5 (en) | 1979-04-30 |
| 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 |
| 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 |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |