EP0385630A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
1H-imidazo(4,5-c)Quinolin-4-amines as antivirals
Assignee: Riker Laboratories Inc
•
Filing: 1990-02-19
•
Granted: —
•
Expires: 2010-02-19
Abstract
Abstract Novel 1H-imidazo[4,5-c]quinolin-4-amines of formula are disclosed. The compounds function as antiviral agents and they are potential synthetic intermediates in the preparation of known antiviral agents and labeled known antiviral agents. Processes for the preparation of the compounds, methods for their antiviral use, and methods of inducing interferon biosynthesis, are also described.
Inventors
- 👤 John F. C/O Riker Laboratories Inc. Gerster
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 18:54
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P31/00; A61P31/12; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D215/42
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
186 words
A compound of the formula: wherein R₂ is selected from the group consisting of hydrogen, straight chain or branched chain alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of straight chain or branched chain alkyl of one to about four carbon atoms, straight chain or branched chain alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of straight chain or branched chain alkoxy of one to about four carbon atoms, halogen, and straight chain or branched chain alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
186 words
A compound of the formula: wherein R₂ is selected from the group consisting of hydrogen, straight chain or branched chain alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of straight chain or branched chain alkyl of one to about four carbon atoms, straight chain or branched chain alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of straight chain or branched chain alkoxy of one to about four carbon atoms, halogen, and straight chain or branched chain alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein R₂ is hydrogen.
Claim 4
Dependent Claim
10 words
A compound according to claim 1, wherein n is zero.
Claim 5
Dependent Claim
23 words
A compound according to claim 1, selected from the group consisting of 1H-imidazo[4,5-c]quinolin-4-amine and 2-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine, and a pharmaceutically acceptable acid-addition salt of either.
Claim 6
Dependent Claim
165 words
A compound of the formula: wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2-hydroxypropyl; R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 7
Dependent Claim
165 words
A compound of the formula: wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2-hydroxypropyl; R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 8
Dependent Claim
164 words
A compound of the formula: wherein R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; R₄ is selected from the group consisting of -C1 and -OH; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 9
Dependent Claim
164 words
A compound of the formula: wherein R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; R₄ is selected from the group consisting of -C1 and -OH; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 10
Dependent Claim
165 words
A compound of the formula wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2-hydroxypropyl; R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 11
Dependent Claim
165 words
A compound of the formula wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2-hydroxypropyl; R₂ is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 12
Dependent Claim
77 words
A compound. of the formula wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2 hydroxypropyl; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 13
Dependent Claim
77 words
A compound. of the formula wherein R₁ is selected from the group consisting of 1,1-dimethyethyl, 1,1-dimethyl-2-hydroxyethyl, and 1,1-dimethyl-2 hydroxypropyl; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 14
Dependent Claim
75 words
A compound of the formula: wherein R₁ is selected from the group consisting of 1,1-dimethyl-2-hydroxyethyl and 1,1-dimethyl-2-hydroxypropyl; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 15
Dependent Claim
75 words
A compound of the formula: wherein R₁ is selected from the group consisting of 1,1-dimethyl-2-hydroxyethyl and 1,1-dimethyl-2-hydroxypropyl; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen, and alkyl of one to about four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms.
Claim 16
Dependent Claim
33 words
An antiviral pharmaceutical composition comprising compound according to claim 1 and a pharmaceutically acceptable vehicle, the compound being present in an amount effective to inhibit and/or prevent the progress of a viral infection.
Claim 17
Dependent Claim
31 words
A method of treating a mammal infected with a virus, comprising administering to the mammal a compound according to claim 1 in an amount effective to inhibit and/or prevent the infection.
Claim 18
Dependent Claim
25 words
A method according to Claim 11, wherein the virus is selected from the group consisting of Type I Herpes simplex and Type II Herpes simplex.
Claim 19
Dependent Claim
28 words
A method of inducing interferon biosynthesis in a human, comprising administering to the human a compound according to Claim 1 in an amount sufficient to induce interferon biosynthesis.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.