Patent CA1208561A successfully refreshed from Google Patents.
CA1208561A
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Pharmaceutical compositions containing benzoylurea compounds
Assignee: Duphar International Research BV
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Filing: 1984-01-19
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Granted: 1986-07-29
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Expires: 2004-01-19
Abstract
Abstract ABSTRACT OF THE DISCLOSURE Pharmaceutical compositions including as an active ingredient a benzoylurea of formula (I): I R11 represents hydrogen, or 1 or 2 substituents chosen from halogen, and alkyl and haloalkyl having 1-4 carbon atoms; R12 represents hydrogen or halogen; R13 represents hydrogen or 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and tri-fluoromethyl; R14 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms; a cycloalkyl group having 3-6 carbon atoms provided that (i) when X is O, R14 is absent; and (ii) when n is zero and R14 is hydrogen, R13 is also hydrogen; R15 represents either a phenyl group, a substituted phenyl group having 1-3 substituents selected from halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms, or R15 represents a bi-or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group sub-stituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms; X represents N, CH, or O and n represents O or 1, provided that (a) when X is N or CH, R11 is halogen in the 2-position, R12 represents hydrogen or halogen in the 6-position R15 represents a phenyl group, or a substituted phenyl group having 1-3 substituents chosen from halogen and alkyl, alkoxy, haloalkyl, or haloalkoxy having 1-4 carbon atoms. (b) when X is 0, then n is zero, R12 is hydrogen, and R15 represents a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group substituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms. These compositions find use in the treatment of cancer.
Inventors
- 👤 Marius S. Brouwer
- 👤 Arnoldus C. Grosscurt
- 👤 Roelof Van Hes
Bibliographic Details
Application Number
—
Jurisdiction
CA
Data Source
google_patents
Last Synchronized
2026-11-09 04:49
CPC Classifications
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Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
271 words
A pharmaceutical composition including as an active ingredient I R11 represents hydrogen, or 1 or 2 substituents chosen from halogen, and alkyl and haloalkyl having 1-4 carbon atoms; R12 represents hydrogen or halogen; R13 represents hydrogen or 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and tri-fluoromethyl; R14 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms; a cycloalkyl group having 3-6 carbon atoms provided that (i) when X is O, R14 is absent; and (ii) when n is zero and R14 is hydrogen, R13 is also hydrogen; R15 represents either a phenyl group, a substituted phenyl group having 1-3 substituents selected from halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms, or R15 represents a bi-or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group sub-stituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms; x represents N, CH, or O and n represents O or 1, provided that (a) when X is N or CH, R11 is halogen in the 2-position, R12 represents hydrogen or halogen in the 6-position R15 represents a phenyl group, or a substituted phenyl group having 1-3 substituents chosen from halogen and alkyl, alkoxy, haloalkyl, or haloalkoxy having 1-4 carbon atoms. (b) when X is 0, then n is zero, R12 is hydrogen, and R15 represents a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group substituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms, together with a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
271 words
A pharmaceutical composition including as an active ingredient I R11 represents hydrogen, or 1 or 2 substituents chosen from halogen, and alkyl and haloalkyl having 1-4 carbon atoms; R12 represents hydrogen or halogen; R13 represents hydrogen or 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and tri-fluoromethyl; R14 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms; a cycloalkyl group having 3-6 carbon atoms provided that (i) when X is O, R14 is absent; and (ii) when n is zero and R14 is hydrogen, R13 is also hydrogen; R15 represents either a phenyl group, a substituted phenyl group having 1-3 substituents selected from halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms, or R15 represents a bi-or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group sub-stituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms; x represents N, CH, or O and n represents O or 1, provided that (a) when X is N or CH, R11 is halogen in the 2-position, R12 represents hydrogen or halogen in the 6-position R15 represents a phenyl group, or a substituted phenyl group having 1-3 substituents chosen from halogen and alkyl, alkoxy, haloalkyl, or haloalkoxy having 1-4 carbon atoms. (b) when X is 0, then n is zero, R12 is hydrogen, and R15 represents a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms, a cyclohexyl group, or a cyclohexyl group substituted with 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms, together with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
114 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula II II wherein R21 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of halogen and alkyl and haloalkyl having 1-4 carbon atoms, R22 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and trifluoromethyl, and R23 is a hydrogen atom or represents 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms, or wherein R23 together with the cyclohexyl ring to which it is attached forms a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms, together with a pharmaceutically acceptable carrier.
Claim 4
Dependent Claim
114 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula II II wherein R21 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of halogen and alkyl and haloalkyl having 1-4 carbon atoms, R22 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and trifluoromethyl, and R23 is a hydrogen atom or represents 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms, or wherein R23 together with the cyclohexyl ring to which it is attached forms a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms, together with a pharmaceutically acceptable carrier.
Claim 5
Dependent Claim
27 words
A pharmaceutical composition according to claim 2 wherein the group R23 together with the cyclohexyl ring comprises a menthyl group, a 2-bornyl group, or a 2-adamantyl group.
Claim 6
Dependent Claim
144 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula III III III wherein R31 is a halogen atom, R32 is a hydrogen atom or a halogen atom, R33 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and trifluoromethyl, R34 is a hydrogen atom or represents 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms, X is N or CH, n is O or 1, and R35 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms, or a cycloalkyl group having 3-6 carbon atoms, with the proviso, that, if n is O and R35 is a hydrogen atom, R33 is a hydrogen atom, together with a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
144 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula III III III wherein R31 is a halogen atom, R32 is a hydrogen atom or a halogen atom, R33 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl, and trifluoromethyl, R34 is a hydrogen atom or represents 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms, X is N or CH, n is O or 1, and R35 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms, or a cycloalkyl group having 3-6 carbon atoms, with the proviso, that, if n is O and R35 is a hydrogen atom, R33 is a hydrogen atom, together with a pharmaceutically acceptable carrier.
Claim 8
Dependent Claim
109 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula IV IV wherein R1 and R2 are both fluorine atoms, or wherein R1 is a chlorine atom and R2 is a hydrogen atom, R3 and n have the above meanings for R33 and n R4 represents 1 or 2 substituents which are selected from the group consisting of halogen, and alkyl, haloalkyl and haloalkoxy having 1-4 carbon atoms, and R5 is a hydrogen atom or an alkyl group having 2-5 carbon atoms, with the proviso, that, if n is O and R5 is a hydrogen atom, R3 is a hydrogen atom, together with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
109 words
A pharmaceutical composition including as an active ingredient a benzoylurea of formula IV IV wherein R1 and R2 are both fluorine atoms, or wherein R1 is a chlorine atom and R2 is a hydrogen atom, R3 and n have the above meanings for R33 and n R4 represents 1 or 2 substituents which are selected from the group consisting of halogen, and alkyl, haloalkyl and haloalkoxy having 1-4 carbon atoms, and R5 is a hydrogen atom or an alkyl group having 2-5 carbon atoms, with the proviso, that, if n is O and R5 is a hydrogen atom, R3 is a hydrogen atom, together with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
87 words
A pharmaceutical composition including as the active ingredient a benzoylurea of formula V V in which: R6 is an alkyl or alkenyl group having 1-4 carbon atoms; R7 is hydrogen or an alkyl or alkenyl group having 1-4 carbon atoms, or R6, R7 and the cyclohexyl ring form a 2-bornyl or 2-adamantyl group; R8 is hydrogen, or 1 or 2 substituents selected from chlorine, methyl and trifluoromethyl; R9 is halogen or a methyl group; and R10 is hydrogen or a halogen, together with a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
87 words
A pharmaceutical composition including as the active ingredient a benzoylurea of formula V V in which: R6 is an alkyl or alkenyl group having 1-4 carbon atoms; R7 is hydrogen or an alkyl or alkenyl group having 1-4 carbon atoms, or R6, R7 and the cyclohexyl ring form a 2-bornyl or 2-adamantyl group; R8 is hydrogen, or 1 or 2 substituents selected from chlorine, methyl and trifluoromethyl; R9 is halogen or a methyl group; and R10 is hydrogen or a halogen, together with a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
18 words
A pharmaceutical composition according to claim 6 wherein R6, R7 and the cyclohexyl ring comprise a menthyl group.
Claim 13
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2,6-difluorobenzoyl)-N'-(4-dl-menthyloxy-phenyl)urea together with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2,6-difluorobenzoyl)-N'-(4-dl-menthyloxy-phenyl)urea together with a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2-chlorobenzoyl)-N'-(4-dl-menthyloxyphenyl)urea together with a pharma-ceutically acceptable carrier.
Claim 16
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2-chlorobenzoyl)-N'-(4-dl-menthyloxyphenyl)urea together with a pharma-ceutically acceptable carrier.
Claim 17
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2,6-difluorobenzoyl)-N'-[4-{N-(4-chlorophenyl)-N-ethylamino}phenyl]urea together with a pharmaceutically acceptable carrier.
Claim 18
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2,6-difluorobenzoyl)-N'-[4-{N-(4-chlorophenyl)-N-ethylamino}phenyl]urea together with a pharmaceutically acceptable carrier.
Claim 19
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2-chlorobenzoyl)-N'-[4-{N'-(4-chlorophenyl)-N'-isopropylureido}phenyl]urea together with a pharmaceutically acceptable carrier.
Claim 20
Dependent Claim
15 words
A pharmaceutical composition including as the active ingredient N-(2-chlorobenzoyl)-N'-[4-{N'-(4-chlorophenyl)-N'-isopropylureido}phenyl]urea together with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
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