Patent US4118487A successfully refreshed from Google Patents.
US4118487A
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Substituted azol-1-ylmethanes
Assignee: Bayer AG
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Filing: 1975-12-05
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Granted: 1978-10-03
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Expires: 1995-12-05
Abstract
Abstract Azol-1-ylmethanes substituted on the methane carbon atom by (a) phenyl or lower alkyl and (b) by a biphenyl-4-yl, 4-phenoxyphenyl, 4-phenylthiophenyl, 4-phenylsulfinylphenyl or 4-phenylsulfonylphenyl group are antimycotic and antibacterial agents. The compounds, of which (biphenyl-4-yl)phenyl-imidazol-1-ylmethane is a typical example, are prepared from the correspondingly substituted carbinol through treatment with thionyl-bis-azole or from the correspondingly substituted methyl halide with the azole or a derivative thereof.
Inventors
- 👤 Erik Regel
- 👤 Wilfried Draber
- 👤 Karl Heinz Buchel
- 👤 Manfred Plempel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:37
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P31/00; A61P31/04; A61P31/10; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/143; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 56
Claim 1
Independent Claim
70 words
A compound selected from the group consisting of an imidazole of the formula: ##STR24## and the pharmaceutically acceptable nontoxic salts thereof, wherein R 1 is hydrogen, halo, lower alkyl; lower alkoxy, halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl, phenyl or phenyl substituted with one or two substituents independently selected from the group consisting of lower alkyl, halo and halo(lower alkyl); and n is 1, 2 or 3.
Claim 2
Dependent Claim
70 words
A compound selected from the group consisting of an imidazole of the formula: ##STR24## and the pharmaceutically acceptable nontoxic salts thereof, wherein R 1 is hydrogen, halo, lower alkyl; lower alkoxy, halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl, phenyl or phenyl substituted with one or two substituents independently selected from the group consisting of lower alkyl, halo and halo(lower alkyl); and n is 1, 2 or 3.
Claim 3
Dependent Claim
17 words
A compound according to claim 1 wherein R 1 is hydrogen; chloro; bromo; lower alkyl; or benzyl.
Claim 4
Dependent Claim
33 words
A compound according to claim 1 wherein R 2 is lower alkyl; phenyl; or phenyl substituted with one or two substituents selected from the group consisting of chloro, bromo, lower alkyl or trifluoromethyl.
Claim 5
Dependent Claim
24 words
A compound according to claim 1 wherein R 1 is hydrogen or chloro; n is 1; R 2 is phenyl, chlorophenyl or (lower alkyl)phenyl.
Claim 6
Dependent Claim
15 words
A compound according to claim 1 wherein said substituted azol-1-ylmethane is of the formula ##STR25##
Claim 7
Dependent Claim
15 words
A compound according to claim 1 wherein said substituted azol-1-ylmethane is of the formula ##STR26##
Claim 8
Dependent Claim
21 words
A compound according to claim 1 wherein R 1 is hydrogen or chloro; and R 2 is phenyl, chlorophenyl or(lower alkyl)phenyl.
Claim 9
Dependent Claim
37 words
A compound according to claim 1 which is a pharmaceutically acceptable, nontoxic salt selected from the group consisting of the hydrochloride, the hydrobromide, phosphate, nitrate, sulfate, acetate, maleate, succinate, fumarate, tartrate, citrate, salicylate, sorbate, lactate and 1,5-naphthalenedisulfonate.
Claim 10
Dependent Claim
41 words
A compound according to claim 1 which is a pharmaceutically acceptable, nontoxic salt of a compound of the formula ##STR27## wherein said salt is selected from the group consisting of the hydrochloride, phosphate, nitrate, sulfate, acetate, lactate, salicylate and 1,5-naphthalene disulfonate.
Claim 11
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is hydrogen; n is 1; and R 2 is 3-methylphenyl.
Claim 12
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 4-chloro; n is 1; and R 2 is 3-chlorophenyl.
Claim 13
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 4-chloro; n is 1; and R 2 is 2-chlorophenyl.
Claim 14
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is hydrogen; n is 1; and R 2 is tert.-butyl.
Claim 15
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 4-chloro; n is 1; and R 2 is n-propyl.
Claim 16
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is hydrogen; n is 1; and R 2 is 3-trifluoromethylphenyl.
Claim 17
Dependent Claim
35 words
A compound according to claim 1 wherein R 1 is chloro; n is 3, said three chloro atoms being in the 2-, 4- and 6-positions of the depicted phenyl ring; and R 2 is phenyl.
Claim 18
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 3-ethyl; n is 1; and R 2 is phenyl.
Claim 19
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is 2-benzyl; n is 1; and R 2 is 2-chlorophenyl.
Claim 20
Dependent Claim
19 words
The compound according to claim 1 wherein R 1 is hydrogen; n is 1; and R 2 is 2,5-dichlorophenyl.
Claim 21
Dependent Claim
110 words
A pharmaceutical composition useful for treating mycoses and bacterial infections in humans and animals which comprises an antimycotically effective amount or an antibacterially effective amount of a compound selected from the group consisting of an imidazole of the formula: ##STR28## and the pharmaceutically acceptable, nontoxic salts thereof, wherein R 1 is hydrogen; halo; lower alkyl; lower alkoxy; halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl; phenyl; or phenyl substituted by one or two substituents independently selected from the group consisting of lower alkyl, halo, and halo(lower alkyl); and n has a value of from 1 to 3, in combination with a pharmaceutically acceptable, nontoxic, inert diluent or carrier.
Claim 22
Dependent Claim
110 words
A pharmaceutical composition useful for treating mycoses and bacterial infections in humans and animals which comprises an antimycotically effective amount or an antibacterially effective amount of a compound selected from the group consisting of an imidazole of the formula: ##STR28## and the pharmaceutically acceptable, nontoxic salts thereof, wherein R 1 is hydrogen; halo; lower alkyl; lower alkoxy; halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl; phenyl; or phenyl substituted by one or two substituents independently selected from the group consisting of lower alkyl, halo, and halo(lower alkyl); and n has a value of from 1 to 3, in combination with a pharmaceutically acceptable, nontoxic, inert diluent or carrier.
Claim 23
Dependent Claim
17 words
A composition according to claim 20 wherein R 1 is hydrogen; chloro; bromo; lower alkyl; or benzyl.
Claim 24
Dependent Claim
33 words
A composition according to claim 20 wherein R 2 is lower alkyl; phenyl; or phenyl substituted with one or two substitutents selected from the group consisting of chloro, bromo, lower alkyl or trifluoromethyl.
Claim 25
Dependent Claim
14 words
A composition according to claim 20 wherein the compound is of the formula ##STR29##
Claim 26
Dependent Claim
14 words
A composition according to claim 20 wherein the compound is of the formula ##STR30##
Claim 27
Dependent Claim
39 words
A composition according to claim 20 wherein the compound is a pharmaceutically acceptable, nontoxic salt selected from the group consisting of the hydrochloride, the hydrobromide, phosphate, nitrate, sulfate, acetate, maleate, succinate, fumarate, tartrate, citrate, salicylate, sorbate, lactate and 1,5-naphthalenedisulfonate.
Claim 28
Dependent Claim
43 words
A composition according to claim 20 wherein the compound is a pharmaceutically acceptable, nontoxic salt of the imidazole of the formula ##STR31## wherein said salt is selected from the group consisting of the hydrochloride, phosphate, nitrate, sulfate, acetate, lactate, salicylate and 1,5-naphthalene disulfonate.
Claim 29
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is hydrogen; n is 1; and R 2 is 3-methylphenyl.
Claim 30
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is 4-chloro; n is 1; and R 2 is 3-chlorophenyl.
Claim 31
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is 4-chloro; n is 1 and R 2 is 2-chlorophenyl.
Claim 32
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is hydrogen; n is 1; and R 2 is tert.-butyl.
Claim 33
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is 4-chloro; n is 1; and R 2 is n-propyl.
Claim 34
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is hydrogen; n is 1; and R 2 is 3-trifluoromethylphenyl.
Claim 35
Dependent Claim
35 words
A composition according to claim 20 wherein R 1 is chloro; n is 3, said three chloro atoms being in the 2-, 4- and 6-positions of the depicted phenyl ring; and R 2 is phenyl.
Claim 36
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is 3-ethyl; n is 1; and R 2 is phenyl.
Claim 37
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is 2-benzyl; n is 1; and R 2 is 2-chlorophenyl.
Claim 38
Dependent Claim
19 words
A composition according to claim 20 wherein R 1 is hydrogen; n is 1; and R 2 is 2,5-dichlorophenyl.
Claim 39
Independent Claim
125 words
A method of treating mycoses and bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an effective amount of a pharmaceutical composition which comprises an antimycotically effective amount or an antibacterially effective amount of a compound selected from the group consisting of an imidazole of the formula: ##STR32## and the pharmaceutically acceptable, nontoxic salts thereof, wherein R 1 is hydrogen; halo; lower alkyl; lower alkoxy; halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl; phenyl; or phenyl substituted by one or two substituents independently selected from the group consisting of lower alkyl, halo, and halo(lower alkyl); n has a value of from 1 to 3, in combination with a pharmaceutically acceptable, nontoxic, inert diluent or carrier.
Claim 40
Independent Claim
125 words
A method of treating mycoses and bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an effective amount of a pharmaceutical composition which comprises an antimycotically effective amount or an antibacterially effective amount of a compound selected from the group consisting of an imidazole of the formula: ##STR32## and the pharmaceutically acceptable, nontoxic salts thereof, wherein R 1 is hydrogen; halo; lower alkyl; lower alkoxy; halo(lower alkyl); or phenyl(lower alkyl); R 2 is lower alkyl; phenyl; or phenyl substituted by one or two substituents independently selected from the group consisting of lower alkyl, halo, and halo(lower alkyl); n has a value of from 1 to 3, in combination with a pharmaceutically acceptable, nontoxic, inert diluent or carrier.
Claim 41
Dependent Claim
17 words
A method according to claim 37 wherein R 1 is hydrogen; chloro; bromo; lower alkyl; or benzyl.
Claim 42
Dependent Claim
33 words
A method according to claim 37 wherein R 2 is lower alkyl; phenyl; or phenyl substituted witn one or two substituents selected from the group consisting of chloro, bromo, lower alkyl or trifluoromethyl.
Claim 43
Dependent Claim
14 words
A method according to claim 37 wherein the compound is of the formula ##STR33##
Claim 44
Dependent Claim
14 words
A method according to claim 37 wherein the compound is of the formula ##STR34##
Claim 45
Dependent Claim
39 words
A method according to claim 37 wherein the compound is a pharmaceutically acceptable, non-toxic salt selected from the group consisting of the hydrochloride, the hydrobromide, phosphate, nitrate, sulfate, acetate, maleate, succinate, fumarate, tartrate, citrate, salicylate, sorbate, lactate and 1,5-naphthalenedisulfonate.
Claim 46
Dependent Claim
43 words
A method according to claim 37 wherein the compound is a pharmaceutically acceptable, nontoxic salt of the imidazole of the formula ##STR35## wherein said salt is selected from the group consisting of the hydrochloride, phosphate, nitrate, sulfate, acetate, lactate, salicylate and 1,5-naphthalene disulfonate.
Claim 47
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is hydrogen; n is 1; and R 2 is 3-methylphenyl.
Claim 48
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is 4-chloro; n is 1; and R 2 is 3-chlorophenyl.
Claim 49
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is 4-chloro; n is 1; and R 2 is 2-chlorophenyl.
Claim 50
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is hydrogen; n is 1; and R 2 is tert.-butyl.
Claim 51
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is 4-chloro; n is 1; and R 2 is n-propyl.
Claim 52
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is hydrogen; n is 1; and R 2 is 3-trifluoromethylphenyl.
Claim 53
Dependent Claim
35 words
A method according to claim 37 wherein R 1 is chloro; n is 3, said three chloro atoms being in the 2-, 4- and 6-positions of the depicted phenyl ring; and R 2 is phenyl.
Claim 54
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is 3-ethyl; n is 1; and R 2 is phenyl.
Claim 55
Dependent Claim
19 words
A method according to claim 37 wherein R 1 is 2-benzyl; n is 1; and R 2 is 2-chlorophenyl.
Claim 56
Dependent Claim
18 words
A method according to claim 37 wherein R 1 is hydrogen; n is 1; and R 2 2,5-dichlorophenyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-02 | 1982-04-03 | 1982-10-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-02 | 1986-04-03 | 1986-10-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-02 | 1990-04-03 | 1990-10-03 | $7700.00 | Window Closed / Lapsed |