EP0412387B1
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Diarylacetylenes, their process and use
Assignee: BASF SE
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Filing: 1990-07-30
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Granted: 1993-11-24
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Expires: 2010-07-30
Abstract
Abstract Diarylacetylenes of the formula I <IMAGE> I where R1 is hydrogen or C1-C4-alkyl, R2 and R3 are each hydrogen or, when R1 is hydrogen, together form a -C(CH3)2-B-C(CH3)2- group (where B is -CH2Ch2- or -CH(CH3)-) or -OC(Ch3) (Z)CH2CH2- group (where Z is C1-C2-alkyl) or R2 is C1-C3-alkoxy and R3 is C1-C10-alkyl or, when R2 is hydrogen, R1 and R3 are each alkyl as defined above, R4 is C1-C6-alkyl and n is 0, 1 or 2, are prepared as described and used as active compounds in drugs and cosmetics.
Inventors
- 👤 Bernd Dr. Dipl.-Chem. Janssen
- 👤 Hans-Heiner Dr. Dipl.-Chem. Wuest
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 12:58
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/63; C07C309/72; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/46; A61P; A61P17/00; A61P35/00; A61P37/00; A61Q; A61Q19/00; A61Q19/004; C07C317/00; C07C317/14; C07C321/00; C07C321/24; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/10
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
82 words
A diarylacetylene of the formula I where R¹ is hydrogen or C₁-C₄-alkyl, R² and R³ are each hydrogen or, when R¹ is hydrogen, together form a -C(CH₃)₂-B-C(CH₃)₂- group (where B is -CH₂CH₂- or -CH(CH₃)-) or a -C(CH₃) (Z)CH₂CH₂O- group (where Z is C₁-C₂-alkyl) or R² is C₁-C₃-alkoxy and R³ is C₁-C₁₀-alkyl which can be straight-chain, branched or (poly)cyclic, or, when R² is hydrogen, R¹ and R³ are each alkyl as defined above, R⁴ is C₁-C₆-alkyl and n is 0, 1 or 2.
Claim 2
Dependent Claim
21 words
A diarylacetylene of the formula I as claimed in claim 1, where R² and R³ together form a -C (CH₃)₂-B-C(CH₃)₂- group.
Claim 3
Dependent Claim
18 words
A diarylacetylene of the formula I as claimed in claim 1, where R¹ and R³ are each C₁-C₄-alkyl.
Claim 4
Dependent Claim
15 words
A diarylacetylene of the formula I as claimed in claim 2, where n is 2.
Claim 5
Dependent Claim
19 words
A diarylacetylene of the formula I as claimed in claim 1, where R³ is adamantyl and R² is C₁-C₃-alkoxy.
Claim 6
Dependent Claim
234 words
A process for the preparation of a diarylacetylene of the formula I as claimed in any of claims 1 to 5, which comprises a) halogenating a stilbene of the formula II where R¹ to R⁴ and n have the meanings specified in claim 1, and subsequently eliminating 2 moles of hydrogen halide, or b) reacting an α-chlorobenzylphosphonate of the formula III where R¹ to R³ have the abovementioned meanings, and R⁵ is C₁-C₃-alkyl, with an aldehyde of the formula IV where R⁴ and n have the meanings specified in claim 1, or c) reacting an α-chlorobenzylphosphonate of the formula V where R⁴, R⁵ and n have the abovementioned meanings, with an aldehyde of the formula VI where R¹ to R³ have the abovementioned meanings, or d) reacting a monoarylacetylene of the formula VII where R¹ to R³ have the abovementioned meanings, with an aryl halide of the formula VIII where R⁴ and n have the abovementioned meanings, and Hal is chlorine, bromine or iodine, in the presence of a catalyst and of a base, or e) reacting an aryl halide of the formula IX where R¹ to R³ and Hal have the abovementioned meanings, with a monoarylacetylene of the formula X where R⁴ has the abovementioned meanings, in the presence of a catalyst and of a base, and converting the resulting compound where appropriate by standard methods into another compound of the formula I.
Claim 7
Dependent Claim
43 words
A drug for topical use or cosmetic preparation which contains as active compound from 0.001 to 1% by weight of a diarylacetylene of the formula I as claimed in any of claims 1 to 5, in addition to conventional pharmaceutical or cosmetic auxiliaries.
Claim 8
Dependent Claim
40 words
A drug for systemic use which contains as active compound per single dose from 0.1 to 250 mg of a diarylacetylene of the formula I as claimed in any of claims 1 to 5, in addition to conventional pharmaceutical auxiliaries.
Claim 9
Dependent Claim
28 words
A drug as claimed in claim 7 for the treatment of acne or psoriasis or other dermatological disorders associated with pathological cornification and of eczema, warts and vitiligo.
Claim 10
Dependent Claim
21 words
A drug as claimed in claim 7 for the treatment of skin damage which is iatrogenic or caused by UV light.
References Cited (Backward Citations)
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