EP0054974A1
Expired / Lapsed
EP
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Imidazolylpropanol compounds and their acid addition salts, and production and use thereof
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1981-12-23
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Granted: —
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Expires: 2001-12-23
Abstract
Abstract An imidazolyl propanol compound of the formula wherein Ph is a phenyl group or a phenyl group substituted with halogen, and A is -S-R' (wherein R 1 is a C 1 -C 15 alkyl group, a phenyl group, a phenyl group substituted with at least one of C 1 -C 8 alkyl. C 1 -C 8 alkoxy and halogen, a benzyl group or a pyridyl group), -O-R 2 (wherein R 2 is a hydrogen atom, a C 1 -C 15 alkyl group, a C 1 -C 8 alkyl group substituted with at least one of phenylthio and C 1 -C 8 alkylthio, a C 3 -C 8 alkenyl group, a C 7 -C 8 aralkyl group, a C 7 -C 8 aralkyl group substituted with halogen, a phenyl group or a phenyl group substituted with at least one of halogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, acetylpiperazino and C 1 -C 8 alkylthio), or (wherein R 3 and R 4 are each a hydrogen atom, a C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, a benzyl group, a benzyl group substituted with halogen, a C 1 -C 8 alkyl group substituted with at least one of hydroxyl, morpholino and C 1 -C 8 alkoxy, a C 3 -C 6 alkynyl group, a furfuryl group or a tetrahydrofurfuryl group, or when taken together with the adjacent nitrogen atom, they represent a morhpholino group, a piperazino group, an N-(C 1 -C 8 )alkylpiperazino group, an N-phenylpiperazino group, an N-benzylpiperazino group, a pyrrolidino group or a piperidino group), and its acid addition salts, which are useful as'antifungal agents.
Inventors
- 👤 Ikutaro Saji
- 👤 Katsumi Tamoto
- 👤 Shunji Aono
- 👤 Katsuaki Ichise
- 👤 Takao Okuda
- 👤 Hideo Agui
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 11:05
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; A; A01; A01N; A01N43/00; A01N43/48; A01N43/50; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
273 words
An imidazolylpropanol compound of the formula: wherein Ph is a phenyl group or a phenyl group substituted with halogen; and A is -S-R 1 (wherein R 1 is a C 1 -C 15 alkyl group, a phenyl group, a phenyl group substituted with at least one of C 1 -C 8 alkyl, C 1 -C 8 alkoxy and halogen, a benzyl group or a pyridyl group), - 0 - R 2 (wherein R 2 is a hydrogen atom, a C 1 -C 15 alkyl group, a C 1 -C 8 alkyl group substituted with at least one of phenylthio and C 1 -C 8 alkylthio, a C 3 -C 8 alkenyl group, a C 7 -C 8 aralkyl group, a C 7 -C 8 aralkyl group substituted with halogen, a phenyl group or a phenyl group substituted with at least one of halogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, acetylpiperazino and C 1 -C 8 alkylthio), or (wherein R 3 and R 4 are each a hydrogen atom, a C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, a benzyl group, a benzyl group substituted with halogen, a C 1 -C 8 alkyl group substituted with at least one of hydroxyl, morpholino and C 1 -C 8 alkoxy, a C 3 -C 6 alkynyl group, a furfuryl group or a tetrahydrofurfuryl group, or when taken together with the adjacent nitrogen atom, they represent a morpholino group, a piperazino group, an N-(C 1 -C 8 )alkylpiperazino group, an N-phenylpiperazino group, an N-benzyl piperazino group, a pyrrolidino group or a piperidino group), and its acid addition salts.
Claim 2
Dependent Claim
273 words
An imidazolylpropanol compound of the formula: wherein Ph is a phenyl group or a phenyl group substituted with halogen; and A is -S-R 1 (wherein R 1 is a C 1 -C 15 alkyl group, a phenyl group, a phenyl group substituted with at least one of C 1 -C 8 alkyl, C 1 -C 8 alkoxy and halogen, a benzyl group or a pyridyl group), - 0 - R 2 (wherein R 2 is a hydrogen atom, a C 1 -C 15 alkyl group, a C 1 -C 8 alkyl group substituted with at least one of phenylthio and C 1 -C 8 alkylthio, a C 3 -C 8 alkenyl group, a C 7 -C 8 aralkyl group, a C 7 -C 8 aralkyl group substituted with halogen, a phenyl group or a phenyl group substituted with at least one of halogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, acetylpiperazino and C 1 -C 8 alkylthio), or (wherein R 3 and R 4 are each a hydrogen atom, a C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, a benzyl group, a benzyl group substituted with halogen, a C 1 -C 8 alkyl group substituted with at least one of hydroxyl, morpholino and C 1 -C 8 alkoxy, a C 3 -C 6 alkynyl group, a furfuryl group or a tetrahydrofurfuryl group, or when taken together with the adjacent nitrogen atom, they represent a morpholino group, a piperazino group, an N-(C 1 -C 8 )alkylpiperazino group, an N-phenylpiperazino group, an N-benzyl piperazino group, a pyrrolidino group or a piperidino group), and its acid addition salts.
Claim 3
Dependent Claim
12 words
The compound according to claim 1, wherein A is -S-R 1 .
Claim 4
Dependent Claim
12 words
The compound according to claim 1, wherein A is -O-R 2 .
Claim 5
Dependent Claim
9 words
The compound according to claim 1, wherein A is
Claim 6
Dependent Claim
25 words
The compound according to claim 2, wherein Ph is a phenyl group substituted with halogen and A is a C 1 -C 15 alkylthio group.
Claim 7
Dependent Claim
24 words
The compound according to claim 3, wherein Ph is a phenyl group substituted with halogen and A is a phenoxy group substituted with halogen.
Claim 8
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a phenylthio group.
Claim 9
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a 3-methylphenylthio group.
Claim 10
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a 4-methoxyphenylthio group.
Claim 11
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a 4-fluorophenylthio group.
Claim 12
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a benzylthio group.
Claim 13
Dependent Claim
18 words
The compound according to claim 5, wherein Ph is a 2,4-dichlorophenyl group and A is an n-butylthio group.
Claim 14
Dependent Claim
18 words
The compound according to claim 2, wherein Ph is a 2,4-dichlorophenyl group and A is a 4-pyridylthio group.
Claim 15
Dependent Claim
18 words
The compound according to claim 3, wherein Ph is a 2,4-dichlorophenyl group and A is an n-butoxy group.
Claim 16
Dependent Claim
18 words
The compound according to claim 3, wherein Ph is a 2,4-dichlorophenyl group and A is an isoamyloxy group.
Claim 17
Dependent Claim
18 words
The compound according to claim 3, wherein Ph is a 2,4-dichlorophenyl group and A is a 2-phenylethyloxy group.
Claim 18
Dependent Claim
18 words
The compound according to claim 6, wherein Ph is a 2,4-dichlorophenyl group and A is a 3-fluorophenoxy group.
Claim 19
Dependent Claim
18 words
The compound according to claim 3, wherein Ph is a 2,4-dichlorophenyl group and A is a 3-methylphenoxy group.
Claim 20
Dependent Claim
18 words
The compound according to claim 6, wherein Ph is a 2,4-dichlorophenyl group and A is a 2,3-dichlorophenoxy group.
Claim 21
Dependent Claim
18 words
The compound according to claim 4, wherein Ph is a 2,4-dichlorophenyl group and A is an n-hexylamino group.
Claim 22
Dependent Claim
18 words
The compound according to claim 4, wherein Ph is a 2,4-dichlorophenyl group and A is a benzylamino group.
Claim 23
Dependent Claim
18 words
The compound according to claim 4, wherein Ph is a 2,4-dichlorophenyl group and A is a 2-hydroxyethylamino group.
Claim 24
Dependent Claim
18 words
The compound according to claim 4, wherein Ph is a 2,4-dichlorophenyl group and A is an N-methylpiperazino group.
Claim 25
Dependent Claim
18 words
The compound according to claim 4, wherein Ph is a 2,4-dichlorophenyl group and A is an N-phenylpiperazino group.
Claim 26
Dependent Claim
106 words
A process for preparing imidazolylpropanol (I) compounds of the formula/as set forth in claim 1 and their acid addition salts, which comprises reacting either a) an epoxide compound of the formula in claim 1 wherein Ph is as defined with a reagent of either one of the formulas: wherein M is an alkali metal atom and R l , R 2 , R 3 and R 4 are each as defined in claim 1, or b) an epoxide compound of the formula in claim 1 wherein Ph and A are each as defined with an imidazole compound of the formula: wherein X is potassium or sodium.
Claim 27
Dependent Claim
38 words
An antifungal composition which comprises an antifungally effective amount of at least one of the imidazolylpropanol compounds and their acid addition salts according to claim 1, as an active ingredient and at least one inert carrier or diluent.
Claim 28
Dependent Claim
22 words
Use of at least one of the imidazolylpropanol compounds and their acid addition salts according to claim 1 as an antifungal agent.
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