US4085222A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pharmaceutical compositions containing 1,3-dioxanes
Assignee: Allen and Hanburys Ltd
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Filing: 1974-11-12
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Granted: 1978-04-18
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Expires: 1994-11-12
Abstract
Abstract Compounds of the general formula I: ##STR1## in which R 1 represents cycloalkyl, aralkyl, heterocyclic aryl, or substituted phenyl, in which the substituents on the phenyl group are one or more of the following groups, that is halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro, dialkylamino or methylenedioxy; R 2 represents a hydrogen atom, or together with the group R 1 and the adjacent carbon atom represents a cycloalkyl group with 3 to 7 carbon atoms inclusive; R 3 represents a group R 5 CO--, or R 5 CH(OH)-- in which R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters of such compounds; and where the compounds contain basic centers, non-toxic phrmaceutically acceptable salts with organic or inorganic acids. Pharmaceutical compositions comprising the specified compounds and other related compounds. Processes for the production of the compounds. The compounds have utility as analgetics.
Inventors
- 👤 Deryck Rhodes
- 👤 Roger Frank Newton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 03:28
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/08; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/75; C07C49/00; C07C49/04; C07C49/17; C07D319/06
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
178 words
Compounds of the formula ##STR21## in which R 1 represents cycloalkyl, aralkyl, or substituted phenyl, in which the substituents on the phenyl group are one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro, or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive; R 3 represents a group R 5 CO--, or R 5 CH(OH)-- in which R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic salts.
Claim 2
Dependent Claim
178 words
Compounds of the formula ##STR21## in which R 1 represents cycloalkyl, aralkyl, or substituted phenyl, in which the substituents on the phenyl group are one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro, or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive; R 3 represents a group R 5 CO--, or R 5 CH(OH)-- in which R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic salts.
Claim 3
Dependent Claim
34 words
Compounds as claimed in claim 1 in which R 1 represents cyclohexyl or a substituted phenyl group in which the substituent is para to the bond between the phenyl nucleus and the dioxan moiety.
Claim 4
Dependent Claim
18 words
Compounds as claimed in claim 1 in which R 3 is an α-hydroxyethyl group or an acetyl group.
Claim 5
Dependent Claim
33 words
Compounds as claimed in claim 1 in which R 4 represents a methyl group or R 4 and R 5 are linked together to produce a six-membered spirocyclic system with the dioxan ring.
Claim 6
Dependent Claim
53 words
Compounds as claimed in claim 1 of the structure: ##STR22## in which R 1 represents a phenyl group substituted by an alkyl (C 1 -C 4 ) group, a hydroxy group, an alkoxy (C 1 -C 4 ) group or a dimethylamino group and R 3 represents --COCH 3 or --CHOHCH 3 .
Claim 7
Dependent Claim
39 words
Compounds as claimed in claim 5 in which R 1 represents p-CH 3 O.C 6 H 4 --, p-(CH 3 ) 2 N.C 6 H 4 --, p-CH 3 C 6 H 4 or p-HOC 6 H 4 --.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-hydroxyphenyl)-α,5-dimethyl-1,3-dioxan-5-methanol.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-methoxyphenyl)α,5-dimethyl-1,3-dioxan-5-methanol.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 2-(p-methylphenyl)α,5-dimethyl-1,3-dioxan-5-methanol.
Claim 11
Dependent Claim
176 words
Compounds of the formula I: ##STR23## in which R 1 represents substituted phenyl, in which the substituents on the phenyl group are one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive, R 3 represents a group R 5 CO-- or R 5 CH(OH)-- in which R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic salts.
Claim 12
Dependent Claim
176 words
Compounds of the formula I: ##STR23## in which R 1 represents substituted phenyl, in which the substituents on the phenyl group are one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive, R 3 represents a group R 5 CO-- or R 5 CH(OH)-- in which R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic salts.
Claim 13
Dependent Claim
9 words
The compound of claim 10 which is [2-(p-methylphenyl)-5-methyl-1,3-dioxan-5-yl]methyl ketone.
Claim 14
Dependent Claim
9 words
The compound of claim 10 which is [2-(p-hydroxyphenyl)-5-methyl-1,3-dioxan-5-yl]methyl ketone.
Claim 15
Dependent Claim
9 words
The compound of claim 10 which is [2-(p-methoxyphenyl)-5-methyl-1,3-dioxan-5-yl]methyl ketone.
Claim 16
Dependent Claim
9 words
The compound of claim 10 which is [2-(p-dimethylaminophenyl)-5-methyl-1,3-dioxan-5-yl]methyl ketone.
Claim 17
Dependent Claim
223 words
A pharmaceutical composition comprising as active ingredient one or more compounds of the formula: ##STR24## in which R 1 represents a straight or branched (C 1 -C 6 ) alkyl group, a cycloalkyl group, an aralkyl (C 1 -C 4 ) group, or phenyl group, which phenyl group may optionally be substituted by one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive; R 3 represents a group HOCH 2 --, R 5 CO-- or R 5 CH(OH)--, where R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic acids; in a pain relieving effective amount in association with a pharmaceutical carrier or diluent.
Claim 18
Dependent Claim
223 words
A pharmaceutical composition comprising as active ingredient one or more compounds of the formula: ##STR24## in which R 1 represents a straight or branched (C 1 -C 6 ) alkyl group, a cycloalkyl group, an aralkyl (C 1 -C 4 ) group, or phenyl group, which phenyl group may optionally be substituted by one or more of the following groups, halogen, hydroxy, alkoxy (C 1 -C 4 ), alkyl (C 1 -C 4 ), nitro or dialkylamino; R 2 represents a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl group with 3 to 7 carbon atoms inclusive; R 3 represents a group HOCH 2 --, R 5 CO-- or R 5 CH(OH)--, where R 5 is methyl or ethyl; R 4 is an alkyl group (C 1 -C 6 ) or a phenyl group; and in which where R 4 is alkyl, R 3 and R 4 may be linked together to produce a 5-, 6- or 7-membered hydrocarbyl spirocyclic system with the adjacent carbon atom of the dioxan ring; and where the compounds contain hydroxyl groups, esters with alkanoic acids of such compounds; and where the compounds contain basic centres, non-toxic pharmaceutically acceptable salts with organic or inorganic acids; in a pain relieving effective amount in association with a pharmaceutical carrier or diluent.
Claim 19
Dependent Claim
42 words
A composition as claimed in claim 15 in which R 1 is an alkyl group or an unsubstituted phenyl group and R 3 represents R 5 CO-- or R 5 CH(OH)-- in which R 5 has the meaning given in claim 15.
Claim 20
Dependent Claim
17 words
A composition as claimed in claim 16 in which R 1 is methyl, tertiary butyl or phenyl.
Claim 21
Dependent Claim
22 words
A composition as claimed in claim 17 in which the groups R 1 -R 5 have the meanings given in claim 1.
Claim 22
Dependent Claim
37 words
A composition as claimed in claim 15 in which the group R 1 represents cyclohexyl or a substituted phenyl group in which the substituent is para to the bond between the phenyl nucleus and the dioxan moiety.
Claim 23
Dependent Claim
20 words
A composition as claimed in claim 15, in which the active ingredient is a compound as claimed in claim 5.
Claim 24
Dependent Claim
14 words
A composition as claimed in claim 15, in a form suitable for oral administration.
Claim 25
Dependent Claim
16 words
A composition as claimed in claim 21 in the form of a tablet, capsule or suspension.
Claim 26
Dependent Claim
27 words
A composition as claimed in claim 22 in dosage unit form each dosage unit containing the whole or part of a per diem dose of 500-4000 mgs.
Claim 27
Dependent Claim
20 words
A composition as claimed in claim 23 each dosage unit containing from 50 mg to 1 g of active ingredient.
Claim 28
Dependent Claim
19 words
A composition as claimed in claim 24 each dosage unit containing from 100 to 500 mg of active ingredient.
Claim 29
Dependent Claim
25 words
A method of relieving pain which comprises administering a pain-relieving effective amount to a patient suffering from pain a compound as defined in claim 15.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-17 | 1981-10-17 | 1982-04-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-17 | 1985-10-17 | 1986-04-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-17 | 1989-10-17 | 1990-04-18 | $7700.00 | Window Closed / Lapsed |