US4006243A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Amino-, mercapto- and -oxy-substituted-phenyl and -phenalkyl imidazoles
Assignee: Bayer Pharma AG
•
Filing: 1975-04-11
•
Granted: 1977-02-01
•
Expires: 1995-04-11
Abstract
Abstract Compounds of the formula ##STR1## wherein Z is a direct bond or alkylene of 1 - 3 carbon atoms which is unsubstituted or substituted on the carbon atom alpha to the phenyl group by alkyl or unsubstituted or substituted phenyl, R 2 and R 3 singly are H, alkyl, alkoxy, alkylmercapto, halo, nitro or, collectively, C 4 H 4 , and R 4 is alkenyl, alkinyl, unsubstituted or substituted phenyl or phenylalkyl, or, when Z is substituted methylene, also alkyl, are useful in combating Germatophyte infections, especially Trichophyton rubrum and mentagrophytes, and yeast infections, especially Candida albicans, as well as bacterial and fungal infections.
Inventors
- 👤 Peter Strehlke
- 👤 Hans-Joachim Kessler
- 👤 Ulrich Redmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:11
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P31/00; C07C; C07C205/00; C07C205/27; C07C205/35; C07C205/36; C07C205/37; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 144
Claim 1
Independent Claim
166 words
An imidazole of the formula ##STR6## wherein Z is a direct bond or ##STR7## wherein n is the integer 0, 1 or 2 and R 1 is hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
166 words
An imidazole of the formula ##STR6## wherein Z is a direct bond or ##STR7## wherein n is the integer 0, 1 or 2 and R 1 is hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
6 words
N-(2,4-Dichlorobenzyl)-2-(1-imidazolylmethyl)-aniline, a compound of claim 1.
Claim 4
Dependent Claim
6 words
N-(2,4-Dichlorobenzyl)-4-(1-imidazolylmethyl)-aniline, a compound of claim 1.
Claim 5
Dependent Claim
6 words
N-(2,4-Dichlorobenzyl)-2-(1-imidazolyl)-aniline, a compound of claim 1.
Claim 6
Dependent Claim
8 words
N-(2,4-Dichlorobenzyl)-4-(1-imidazolyl)-aniline, hydrochloride, dihydrate, a compound of claim 1.
Claim 7
Dependent Claim
167 words
An imidazole of the formula ##STR8## wherein Z is a direct bond or ##STR9## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, and the physiologically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
167 words
An imidazole of the formula ##STR8## wherein Z is a direct bond or ##STR9## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, and the physiologically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolylmethyl)-phenyl[-sulfide, hydrochloride, a compound of claim 6.
Claim 10
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-butyl[-phenyl}-sulfide, a compound of claim 6.
Claim 11
Dependent Claim
6 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-sulfide, a compound of claim 6.
Claim 12
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 13
Dependent Claim
6 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-butyl-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 14
Dependent Claim
8 words
4-Chloro-2'-(1-imidazolylmethyl)-diphenyl sulfide, hydrochloride, a compound of claim 6.
Claim 15
Dependent Claim
7 words
Benzyl-[2-(1-imidazolymethyl)-phenyl]-sulfide, hydrochloride, a compound of claim 6.
Claim 16
Dependent Claim
7 words
(4-Chlorobenzyl)-[2-(1-imidazolymethyl)-phenyl]-sulfide, hydrochloride, a compound of claim 6.
Claim 17
Dependent Claim
7 words
(3-Chlorobenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfide, hydrochloride, a compound of claim 6.
Claim 18
Dependent Claim
7 words
(3,4-Dichlorobenzyl)-[2-(1-imidazolylmethyl)-phenyl]-sulfide, hydrochloride, a compound of claim 6.
Claim 19
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[4-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 20
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 21
Dependent Claim
6 words
(3-Chlorobenzyl)-[2-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 22
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-[2-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 23
Dependent Claim
6 words
(3,4-Dichlorophenyl)-[2-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 24
Dependent Claim
6 words
(3,4-Dichloro-γ-methylbenzyl)-[2-(1-imidazolyl)-phenyl]-sulfide, a compound of claim 6.
Claim 25
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{4-[3-(1-imidazolyl)-1-propyl]-phenyl}-sulfide, a compound of claim 6.
Claim 26
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[2-(1-imidazolyl)-ethyl]-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 27
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-propyl]-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 28
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-ethyl-2-(1-imidazolyl)-ethyl]-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 29
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-1-methylpropyl]-4-methoxyphenyl}-sulfide, a compound of claim 6.
Claim 30
Dependent Claim
135 words
An imidazole of the formula ##STR10## wherein R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) alkenyl of 3-6 carbon atoms, (b) alkinyl of 3-6 carbon atoms, (c) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (d) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms, or alkoxy of 1-6 carbon atoms; or (e) alkyl of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 31
Dependent Claim
135 words
An imidazole of the formula ##STR10## wherein R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is (a) alkenyl of 3-6 carbon atoms, (b) alkinyl of 3-6 carbon atoms, (c) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (d) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms, or alkoxy of 1-6 carbon atoms; or (e) alkyl of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 32
Dependent Claim
7 words
Allyl-[2-(1-imidazolyl)-phenyl]-ether, hydrochloride, a compound of claim 28.
Claim 33
Dependent Claim
6 words
[2-(1-Imidazolyl)-phenyl]-(2-propinyl)-ether, a compound of claim 28.
Claim 34
Dependent Claim
6 words
[2-(1-Imidazolyl)-phenyl]-(4-methylbenzyl)-ether, a compound of claim 28.
Claim 35
Dependent Claim
6 words
[2-(1-Imidazolyl)-phenyl]-(4-methoxybenzyl)-ether, a compound of claim 28.
Claim 36
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolyl)-phenyl]-ether, hydrochloride, a compound of claim 28.
Claim 37
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-[4-(1-imidazolyl)-phenyl]-ether, hydrochloride, a compound of claim 28.
Claim 38
Dependent Claim
7 words
[2-(1-Imidazolyl)-phenyl]-2-nitrobenzyl ether, a compound of claim 28.
Claim 39
Dependent Claim
7 words
[2-(1-Imidazolyl)-phenyl]-[3-(trifluoromethyl)-benzyl]-ether, hydrochloride, a compound of claim 28.
Claim 40
Dependent Claim
7 words
(3,4-Dichlorobenzyl)-[2-(1-imidazolyl)-4-methylphenyl]-ether, sulfate, a compound of claim 28.
Claim 41
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolyl)-4-nitrophenyl]-ether, a compound of claim 28.
Claim 42
Dependent Claim
6 words
[4-Chloro-2-(1-imidazolyl)-phenyl]-2,4-dichlorobenzyl)-ether, a compound of claim 28.
Claim 43
Dependent Claim
6 words
[4-Chloro-2-(1-imidazolyl)-phenyl]-(3,4-dichlorobenzyl)-ether, a compound of claim 28.
Claim 44
Dependent Claim
6 words
[5-Chloro-2-(1-imidazolyl)-phenyl]-(3,4-dichlorobenzyl)-ether, a compound of claim 28.
Claim 45
Dependent Claim
6 words
[4-Chloro-2-(1-imidazolyl)-phenyl]-(3,4-dichloro-α-methylbenzyl)-ether, a compound of claim 28.
Claim 46
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-[3,5-dichloro-2-(1-imidazolyl)-phenyl]-ether, a compound of claim 28.
Claim 47
Dependent Claim
8 words
4-(1-Imidazolyl)-diphenyl ether, hydrochloride, a compound of claim 28.
Claim 48
Dependent Claim
131 words
An imidazole of the formula ##STR11## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 49
Dependent Claim
131 words
An imidazole of the formula ##STR11## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 carbon atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; R 4 is phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 50
Dependent Claim
14 words
A compound of claim 45 wherein R 1 is alkyl of 1-6 carbon atoms.
Claim 51
Dependent Claim
9 words
A compound of claim 45 wherein n is 0.
Claim 52
Dependent Claim
7 words
[4-(1-Imidazolylmethyl)-phenyl]-benzyl ether, a compound of claim 45.
Claim 53
Dependent Claim
7 words
[4-(1-Imidazolylmethyl)-phenyl]-(2-nitrobenzyl)-ether, hydrochloride, a compound of claim 45.
Claim 54
Dependent Claim
6 words
[4-(1-Imidazolylmethyl)-phenyl]-(p-tolylmethyl)-ether, a compound of claim 45.
Claim 55
Dependent Claim
6 words
[4-(1-Imidazolylmethyl)-phenyl]-(4-methoxybenzyl)-ether, a compound of claim 45.
Claim 56
Dependent Claim
6 words
(4-Chlorobenzyl)-[4-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 57
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[4-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 58
Dependent Claim
7 words
(2,6-Dichlorobenzyl)-[4-(1-imidazolylmethyl)-phenyl]-ether, hydrochloride, a compound of claim 45.
Claim 59
Dependent Claim
6 words
(4-Bromobenzyl)-[4-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 60
Dependent Claim
7 words
[4-(1-Imidazolylmethyl)-phenyl]-(3-trifluoromethylbenzyl)-ether, hydroperchlorate, a compound of claim 45.
Claim 61
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 62
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[3-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 63
Dependent Claim
7 words
[4-Bromo-2-(1-imidazolylmethyl)-phenyl]-(2,4-dichlorobenzyl)-ether, hydrochloride, a compound of claim 45.
Claim 64
Dependent Claim
6 words
[4-Chloro-2-(1-imidazolylmethyl)-phenyl]-(3,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 65
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-[3,5-dichloro-2-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 66
Dependent Claim
6 words
[4-Chloro-2-(1-imidazolylmethyl)-phenyl]-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 67
Dependent Claim
7 words
[4,6-Dibromo-2-(1-imidazolylmethyl)-phenyl]-(2,4-dichlorobenzyl)-ether, hydrochloride, a compound of claim 45.
Claim 68
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolylmethyl)-4-methylphenyl]-ether, a compound of claim 45.
Claim 69
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-]2-(1-imidazolylmethyl)-4-(1,1,3,3-tetramethylbutyl)-phenyl]-ether, hydrochloride, a compound of claim 45.
Claim 70
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[4-(1-imidazolylmethyl)-2-methoxyphenyl]-ether, a compound of claim 45.
Claim 71
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2-(1-imidazolylmethyl)-4-methylthiophenyl]-ether, a compound of claim 45.
Claim 72
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[3-(1-imidazolylmethyl)-2-naphthyl]-ether, a compound of claim 45.
Claim 73
Dependent Claim
6 words
[4-(1-Imidazolylmethyl)-2-nitrophenyl]-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 74
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{4-[α-(1-imidazolyl)-benzyl]-phenyl}-ether, hydroperchlorate, a compound of claim 45.
Claim 75
Dependent Claim
6 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-propyl]-phenyl}-ether, a compound of claim 45.
Claim 76
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-propyl]-phenyl}-ether, a compound of claim 45.
Claim 77
Dependent Claim
6 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-2-methyl)-propyl]-phenyl}-ether, a compound of claim 45.
Claim 78
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-2-methylpropyl]-phenyl}-ether, a compound of claim 45.
Claim 79
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-pentyl]-phenyl}-ether, a compound of claim 45.
Claim 80
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{4-[α-(1-imidazolyl)-4-methylbenzyl]-phenyl}-ether, a compound of claim 45.
Claim 81
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[2,4-dimethoxy-α-(1-imidazolyl)-benzyl]-5-methoxyphenyl}-ether, a compound of claim 45.
Claim 82
Dependent Claim
6 words
{2-[4-Chloro-α-(1imidazolyl)-benzyl]-5-methoxyphenyl}-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 83
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{4-[α-(1-imidazolyl)-4-nitrobenzyl]-phenyl}-ether, a compound of claim 45.
Claim 84
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{4-[1-(1-imidazolyl)-ethyl]-phenyl}-ether, hydroperchlorate, a compound of claim 45.
Claim 85
Dependent Claim
6 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-ethyl]-phenyl}-ether, a compound of claim 45.
Claim 86
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-ethyl]-phenyl}-ether, a compound of claim 45.
Claim 87
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 88
Dependent Claim
6 words
(3-Chloro-α-methylbenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 89
Dependent Claim
6 words
(3,4-Dichloro-α-methylbenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 90
Dependent Claim
6 words
(3-Chlorobenzyl)-{5-chloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 91
Dependent Claim
6 words
{5-Chloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-(3,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 92
Dependent Claim
6 words
(3-Chlorobenzyl)-{4-chloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 93
Dependent Claim
6 words
{4-Chloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-(3,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 94
Dependent Claim
6 words
{4-Chloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 95
Dependent Claim
6 words
(3-Chlorobenzyl)-{3,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 96
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{3,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 97
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{3,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 98
Dependent Claim
6 words
(3-Chlorobenzyl)-{4,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 99
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{4,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 100
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{4,5-dichloro-2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 101
Dependent Claim
6 words
{4-Chloro-2-[.alpha.-(1-imidazolyl)-benzyl]-phenyl}-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 102
Dependent Claim
7 words
(4-Bromobenzyl)-[4-bromo-2-(1-imidazolylmethyl)-phenyl]-ether, hydrochloride, a compound of claim 45.
Claim 103
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[4-chloro-2-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 104
Dependent Claim
6 words
[5-Bromo-2-(1-imidazolylmethyl)-phenyl]-(2,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 105
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, nitrate, a compound of claim 45.
Claim 106
Dependent Claim
7 words
(3-Chlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 107
Dependent Claim
7 words
(3,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 108
Dependent Claim
7 words
(4-Bromobenzyl)-{2-[1-(1-imidazolyl)-butyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 109
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-heptyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 110
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[1-(1-imidazolyl)-ethyl]-phenyl}-ether, a compound of claim 45.
Claim 111
Dependent Claim
6 words
Benzyl-{4-[1-(1-imidazolyl)-butyl]-phenyl}-ether, a compound of claim 45.
Claim 112
Dependent Claim
7 words
(3,4-Dichlorobenzyl)-[4-(1-imidazolylmethyl)-phenyl]-ether, hydrochloride, a compound of claim 45.
Claim 113
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-[2,6-dichloro-4-(1-imidazolylmethyl)-phenyl]-ether, a compound of claim 45.
Claim 114
Dependent Claim
7 words
(3,4-Dichloro-α-methylbenzyl)-[2-(1-imidazolylmethyl)-phenyl]-ether, hydrochloride, a compound of claim 45.
Claim 115
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{4-[2-(1-imidazolyl)-ethyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 116
Dependent Claim
7 words
(2,4-Dichlorobenzyl)-{2-[2-(1-imidazolyl)-ethyl]-phenyl}-ether, hydrochloride, a compound of claim 45.
Claim 117
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[1-ethyl-2-(1-imidazolyl)-ethyl]-phenyl}-ether, a compound of claim 45.
Claim 118
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[1-ethyl-2-(1-imidazolyl)-ethyl]-phenyl}-ether, a compound of claim 45.
Claim 119
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[2-(1-imidazolyl)-1-propylethyl]-phenyl}-ether, a compound of claim 45.
Claim 120
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[2-(1-imidazolyl)-1-propylethyl]-phenyl}-ether, a compound of claim 45.
Claim 121
Dependent Claim
8 words
(2,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-propyl]-phenyl}-ether, hydrochloride, hydrate, a compound of claim 45.
Claim 122
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-1-methylpropyl]-phenyl}-ether, a compound of claim 45.
Claim 123
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-1-methylpropyl]-phenyl}-ether, a compound of claim 45.
Claim 124
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-1-propylpropyl]-phenyl}-ether, a compound of claim 45.
Claim 125
Dependent Claim
6 words
(3,4-Dichlorobenzyl)-{2-[3-(1-imidazolyl)-1-propylpropyl]-phenyl}-ether, a compound of claim 45.
Claim 126
Dependent Claim
7 words
{5-Bromo-4-[3-(1-imidazolyl)-propyl]-2-methoxyphenyl}-(2,4-dichlorobenzyl)-ether, hydrochloride, a compound of claim 45.
Claim 127
Dependent Claim
6 words
{4-Chloro-2-[3-(1-imidazolyl)-1-phenylpropyl]-phenyl}-(3,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 128
Dependent Claim
6 words
(2,4-Dichlorobenzyl)-{4-[3-(1-imidazolyl)-1-(4-methylphenyl)-propyl]-phenyl}-ether, a compound of claim 45.
Claim 129
Dependent Claim
6 words
{4-[1-(4-Chlorophenyl)-3-(1-imidazolyl)-propyl]-phenyl}-(3,4-dichlorobenzyl)-ether, a compound of claim 45.
Claim 130
Dependent Claim
7 words
{4-[3-(1-Imidazolyl)-1-methylpropyl]-phenyl}-(4-methylbenzyl)-ether, hydrochloride, a compound of claim 45.
Claim 131
Dependent Claim
91 words
An imidazole of the formula ##STR12## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and R 4 is phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 132
Dependent Claim
91 words
An imidazole of the formula ##STR12## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and R 4 is phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 133
Dependent Claim
8 words
2-(1-Imidazolylmethyl)-diphenyl ether, hydrochloride, a compound of claim 127.
Claim 134
Dependent Claim
8 words
4-Chloro-2'-(1-imidazolylmethyl)-diphenyl ether, hydrochloride, a compound of claim 127.
Claim 135
Dependent Claim
78 words
An imidazole of the formula ##STR13## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and R 4 is alkenyl of 3-6 carbon atoms or alkinyl of 3-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 136
Dependent Claim
78 words
An imidazole of the formula ##STR13## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms; R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 carbon atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and R 4 is alkenyl of 3-6 carbon atoms or alkinyl of 3-6 carbon atoms; and the physiologically acceptable acid addition salts thereof.
Claim 137
Dependent Claim
6 words
[4-(1-Imidazolylmethyl)-phenyl]-(2-propinyl)-ether, a compound of claim 130.
Claim 138
Dependent Claim
7 words
[4-(1-Imidazolylmethyl)-phenyl]-(2-propenyl)-ether, hydroperchlorate, a compound of claim 130.
Claim 139
Dependent Claim
2 words
Hexyl-[4-(1-imidazolylmethyl)-phenyl]-ether, hydroperchlorate.
Claim 140
Dependent Claim
2 words
Hexyl-[4-(1-imidazolylmethyl)-phenyl]-ether, hydroperchlorate.
Claim 141
Dependent Claim
480 words
A pharmaceutical composition adapted for the treatment of fungal, bacterial and yeast infections in animals comprising, in admixture with a pharmaceutical carrier, an amount effective to treat such an infection of an imidazole of the formula ##STR14## wherein R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 1-6 atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and I. x is NH, Z is a direct bond or ##STR15## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro groups; and R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluormethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkly of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or Ii. x is S and Z, R 1 and R 4 are as defined in I, above, or Iii. x is O, Z is a direct bond and R 4 is (a) alkenyl of 3-6 carbon atoms, (b) alkinyl of 3-6 carbon atoms, (c) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (d) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or (e) alkyl of 1-6 carbon atoms; or Iv. x is O, Z is ##STR16## wherein n is the integer 0, 1 or 2 and R 1 is phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, and R 4 is phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or V. x is O, Z is ##STR17## wherein R 1 is H or alkyl of 1-6 carbon atoms, and R 4 is phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or Vi. x is O, Z is ##STR18## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms, and R 4 is alkenyl of 3-6 carbon atoms or alkinyl of 3-6 carbon atoms; or a physiologically acceptable salt thereof.
Claim 142
Dependent Claim
480 words
A pharmaceutical composition adapted for the treatment of fungal, bacterial and yeast infections in animals comprising, in admixture with a pharmaceutical carrier, an amount effective to treat such an infection of an imidazole of the formula ##STR14## wherein R 2 and R 3 each are hydrogen atoms, alkyl of 1-10 carbon atoms, alkoxy of 1-6 1-6 atoms, alkylmercapto of 1-6 carbon atoms, halogen atoms or nitro, or collectively are C 4 H 4 ; and I. x is NH, Z is a direct bond or ##STR15## wherein n is the integer 0, 1 or 2 and R 1 is a hydrogen atom, alkyl of 1-6 atoms, phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms and nitro groups; and R 4 is (a) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluormethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (b) phenylalkly of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or Ii. x is S and Z, R 1 and R 4 are as defined in I, above, or Iii. x is O, Z is a direct bond and R 4 is (a) alkenyl of 3-6 carbon atoms, (b) alkinyl of 3-6 carbon atoms, (c) phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, or (d) phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or (e) alkyl of 1-6 carbon atoms; or Iv. x is O, Z is ##STR16## wherein n is the integer 0, 1 or 2 and R 1 is phenyl or phenyl substituted by one to three of halogen atoms, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms, and R 4 is phenylalkyl of 1-4 carbon atoms in the alkyl group wherein phenyl is unsubstituted or substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or V. x is O, Z is ##STR17## wherein R 1 is H or alkyl of 1-6 carbon atoms, and R 4 is phenyl or phenyl substituted by one to three of halogen atoms, nitro, trifluoromethyl, alkyl of 1-6 carbon atoms and alkoxy of 1-6 carbon atoms; or Vi. x is O, Z is ##STR18## wherein R 1 is a hydrogen atom or alkyl of 1-6 carbon atoms, and R 4 is alkenyl of 3-6 carbon atoms or alkinyl of 3-6 carbon atoms; or a physiologically acceptable salt thereof.
Claim 143
Dependent Claim
31 words
A method of treating fungal, bacterial and yeast infections in animals which comprises administering to the infected animal an amount of a composition of claim 134 effective to combat the infection.
Claim 144
Dependent Claim
13 words
A method according to claim 134 wherein the infection is a dermatophyte infection.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1980-02-01 | 1980-08-02 | 1981-02-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-01 | 1984-08-02 | 1985-02-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-01 | 1988-08-02 | 1989-02-01 | $7700.00 | Window Closed / Lapsed |