Patent EP0315071B1 successfully refreshed from Google Patents.
EP0315071B1
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Benzocyclohepten derivatives, their preparation and utilisation for pharmaceutics
Assignee: F Hoffmann La Roche AG
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Filing: 1988-10-28
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Granted: 1994-07-20
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Expires: 2008-10-28
Abstract
Abstract Compounds of the general formula <IMAGE> in which R<1> denotes hydroxyl, lower alkoxy, amino, mono- or di-lower alkylamino; R<2> denotes hydrogen, alkyl, alkoxy or halogen; R<3>, R<4>, R<5>, R<6>, R<1><1> and R<1><2> independently of one another denote hydrogen or lower alkyl; R<3> and R<5> together denote a methylene or hydroxymethylene group; R<7>, R<8>, R<9> and R<1><0> denote hydrogen or lower alkyl; or R<1><1> and R<1><2> together denote an oxo group or spirocyclo-lower alkyl; or R<1><1> denotes hydrogen and R<1><2> denotes hydroxyl or acetoxy; and one of the radicals R<1><3> and R<1><4> denotes hydrogen and the other denotes lower alkyl or trifluoromethyl, and physiologically tolerable salts of carboxylic acids of the formula I can be used as medicines, in particular for the treatment of neoplasias, acne and psoriasis. The novel compounds can be prepared by synthesis of the C(R<1><3>)=C(R<1><4>) double bond according to Wittig from an appropriate bicyclic and an appropriate monocyclic component and, if appropriate, subsequent modification of functional groups.
Inventors
- 👤 Michael Dr. Klaus
- 👤 Peter Dr. Mohr
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 17:47
CPC Classifications
C; C07; C07C; C07C65/00; C07C65/01; C07C65/19; C07C69/00; C07C69/612; C07C69/618; A; A61; A61P; A61P17/00; A61P29/00; A61P3/00; A61P3/06; A61P35/00; A61P37/00; A61P37/08; C07C33/00; C07C33/05; C07C33/16; C07C45/00; C07C45/45; C07C45/46; C07C45/51; C07C45/511; C07C45/513; C07C45/61; C07C45/67; C07C45/68; C07C47/00; C07C47/38; C07C47/457; C07C49/00; C07C49/587; C07C49/657; C07C49/665; C07C49/67; C07C49/687; C07C49/697; C07C49/76; C07C49/782; C07C49/792; C07C63/00; C07C63/66; C07C63/68; C07C63/74; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/32
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
104 words
Compounds of the general formula wherein R¹ signifies hydroxy, lower-alkoxy, amino mono- or dilower-alkylamino; R² signifies hydrogen alkyl, alkoxy or halogen; R³, R⁴, R⁵, R⁶, R¹¹ and R¹² each independently signify hydrogen or lower-alkyl; R³ and R⁵ together signify a methylene or hydroxymethylene group; R⁷, R⁸ R⁹ and R¹⁰ signify hydrogen or lower-alkyl; or R¹¹ and R¹² together signify an oxo group or spiro-cyclo-lower alkyl; or R¹¹ signifies hydrogen and R¹² signifies hydroxy or acetoxy; and one of the residues R¹³ and R¹⁴ signifies hydrogen and the other signifies lower-alkyl or trifluoromethyl, as well as physiologically compatible salts of carboxylic acids of formula I.
Claim 2
Dependent Claim
98 words
Compounds in accordance with claim 1, in which R¹ signifies hydroxy, lower-alkoxy, amino, mono- or di-lower-alkylamino; R² signifies hydrogen, alkyl, alkoxy or halogen; R³, R⁴, R⁵, R⁶, R¹¹ and R¹² each independently signify hydrogen or lower-alkyl; R³ and R⁵ together signify a methylene group; R⁷, R⁸, R⁹ and R¹⁰ signify hydrogen or lower-alkyl; R¹¹ and R¹² together signify an oxo group or R¹¹ signifies hydrogen and R¹² signifies hydroxy; and one of the residues R¹³ and R¹⁴ signifies hydrogen and the other signifies lower-alkyl or trifluoromethyl, as well as physiologically compatible salts of carboxylic acids of formula I.
Claim 3
Dependent Claim
15 words
Compounds in accordance with claim 1 or 2, in which R¹ is hydroxy or lower-alkoxy.
Claim 4
Dependent Claim
11 words
Compounds in accordance with claims 1-3, in which R² is hydrogen.
Claim 5
Dependent Claim
23 words
Compounds in accordance with claims 1-4, in which R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹² are hydrogen or lower-alkyl.
Claim 6
Dependent Claim
17 words
Compounds in accordance with claims 1-4, in which at least one of the residues R³-R¹² is lower-alkyl.
Claim 7
Dependent Claim
16 words
Compounds in accordance with claims 1-4, in which R¹¹ and R¹² together represent an oxo group.
Claim 8
Dependent Claim
15 words
Compounds in accordance with claims 1-4, in which R¹¹ signifies hydrogen and R¹² signifies hydroxy.
Claim 9
Dependent Claim
16 words
Compounds in accordance with claims 1-4, in which R³ and R⁵ together represent a methylene group.
Claim 10
Dependent Claim
2 words
Ethyl p-[(E)-2-(6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate.
Claim 11
Dependent Claim
44 words
The compounds ethyl p-[(E)-2-(6,7,8,9-tetrahydro-9,9-dimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5,5-dimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5,9,9-trimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5,5,9-trimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5,5,9,9-tetramethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-7,7,9-trimethyl-5H benzocyclohepten-2-yl)propenyl]benzoate; methyl p-[(E)-2-(6,7,8,9-tetrahydro-7,7,9,9-tetramethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(7-ethyl-6,7,8,9-tetrahydro-7-methyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; p-[(E)-2-(6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; P-[(E)-2-(6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; p-[(E)-2-(6,7,8,9-tetrahydro-5,5,9,9-tetramethyl-5H-benzocycohepten-2-yl)propenyl]benzoic acid; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-7-methyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; p-[(E)-2-(6,7,8,9-tetrahydro-6,6,8,8-tetramethyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; methyl p-[(E)-(6,7,8,9-tetrahydro-3,7,7-trimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-9-methyl-5H-benzocyclohepten-2-yl)propenyl]benzoate; p-[(E)-2-(6,7,8,9-tetrahydro-7,7,9,9-tetramethyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; p-[(Z)-(6,7,8,9-tetrahydro-7,7-dimethyl-3-octyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; p-[(Z)-2-(3-bromo-6,7-8,9-tetrahydro-7,7-dimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; p-[(Z)-2-(6,7,8,9-tetrahydro-3,7,7-trimethyl-5H-benzocyclohepten-2-yl)propenyl]benzoic acid and ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)propenyl]benzoate.
Claim 12
Dependent Claim
7 words
The compounds ethyl p-[(E)-2-[5,6,8,9-tetrahydrospiro[7H-benzocyclohepten-7,1'-cyclopropane]-2-yl]propenyl]benzoate and ethyl p-[(E)-2-[5,6,8,9-tetrahydrospiro[7H-benzocyclohepten-7,1'-cyclopentane]-2-yl]propenyl]benzoate.
Claim 13
Dependent Claim
7 words
The compounds ethyl p-[(E)-2-(6,7,8,9-tetrahydro-7-oxo-5H-benzocyclohepten-2-yl)propenyl]benzoate and ethyl p-[(E)-2-(6,7,8,9-tetrahydro-6,6,8,8-tetramethyl-7-oxo-5H-benzocyclohepten-2-yl)propenyl]benzoate.
Claim 14
Dependent Claim
11 words
The compounds ethyl p-[(E)-2-(6,7,8,9-tetrahydro-10-acetoxy-5,9-dimethyl-5,9-methano-5H-benzocyclohepten-2-yl)propenyl]-benzoate; p-[(E)-2-(6,7,8,9-tetrahydro-10-hydroxy-5,9-dimethyl-5,9-methano-5H-benzocyclohepten-2-yl)propenyl]benzoic acid; ethyl p-[(E)-2-(6,7,8,9-tetrahydro-5,9-dimethyl-5.9-methano-5H-benzocyclohepten-2-yl)propenyl]benzoate and p-[(E)-2-(6,7,8,9-tetrahydro-5,9-dimethyl-5,9-methano-5H-benzocyclohepten-2-yl)propenyl]benzoic acid.
Claim 15
Dependent Claim
10 words
Compounds in accordance with claims 1-14 for use as medicaments.
Claim 16
Dependent Claim
142 words
A process for the manufacture of compounds of general formula I, characterized by reacting a compound of the general formula with a compound of the general formula wherein A represents a residue -CH(R¹³)P⁺(Q)₃Y⁻ and B represents a residue -CO(R¹⁴)-; or A represents a residue -CO(R¹³)- and B represents a residue -CH₂- -PO(OAlk)₂; Q represents aryl, Y⁻ represents the anion of an organic or inorganic acid, Alk represents a lower alkyl group and R¹-R¹⁴ have the significance given above and wherein a hydroxy or oxo group present as R¹¹ or R¹¹ and R¹² is present in protected form, cleaving off from the condensation product a hydroxy or oxo protecting group which may be present and, if desired, saponifying an ester group -COR¹ of the thus-obtained compound of formula I or converting it into a carboxamino group or a N-mono- or dialkylated carboxamino group.
Claim 17
Dependent Claim
14 words
Pharmaceutical preparations, containing a compound in accordance with claim 1 and usual carrier substances.
Claim 18
Dependent Claim
22 words
Compounds in accordance with claims 1-14 for use as active substances in pharmaceutical preparations having anti-seborrhoic, anti-keratinizing, anti-neoplastic, anti-allergic and anti-inflammatory activity.
References Cited (Backward Citations)
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