EP0077551A2
Expired / Lapsed
EP
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1.4-Naphthoquinones, methods for their preparation, pharmaceutical and veterinary formulations thereof
Assignee: Wellcome Foundation Ltd
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Filing: 1982-10-15
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Granted: —
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Expires: 2002-10-15
Abstract
Abstract 1,4-Naphthoquinones of formula (I), methods for their preparation, pharmaceutical and veterinary formulations thereof and the use thereof in human and animal therapy are disclosed. Particularly preferred compounds of formula (I) are 2-(4'-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone and 2-hydroxy-3-(4'-t-pentylcyclohexyl)-1,4-naphthoquinone. The compounds are of value as antiprotozoal agents, in particular antimalarial and anticoccidial agents.
Inventors
- 👤 Alan Thomas Hudson
- 👤 Anthony Winchester Randall
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 17:48
CPC Classifications
C; C07; C07C; C07C61/00; C07C61/16; C07C61/22; A; A61; A61K; A61K31/00; A61K31/12; A61P; A61P17/00; A61P27/00; A61P27/02; A61P29/00; A61P33/00; A61P33/02; A61P43/00; C07C46/00; C07C50/00; C07C50/24; C07C50/26; C07C50/32; C07C51/00; C07C51/08; C07C51/347; C07C51/353; C07C51/36; C07C51/42; C07C51/487; C07C53/00; C07C53/132; C07C53/134; C07C61/08; C07C61/15; Y; Y02; Y02A; Y02A50/00; Y02A50/30
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
21 words
A compound of the formula (I) wherein R is a C 1 -C 10 alkyl group, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
21 words
A compound of the formula (I) wherein R is a C 1 -C 10 alkyl group, and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
15 words
A compound as claimed in claim 1 wherein R is a straight chain alkyl group.
Claim 4
Dependent Claim
21 words
A compound as claimed in claim 1 or claim 2 where R is a straight chain C l -4 alkyl group.
Claim 5
Dependent Claim
16 words
A compound as claimed in any one of claims 1 to 3 wherein R is methyl.
Claim 6
Dependent Claim
16 words
A compound as claimed in any one of claims 1 to 3 wherein R is ethyl.
Claim 7
Dependent Claim
19 words
A compound as claimed in any one of claims 1 to 5 in the form of a cis/trans mixture.
Claim 8
Dependent Claim
14 words
A compound as claimed in claim 6 wherein the isomer ratio is approximately 1:1.
Claim 9
Dependent Claim
22 words
A compound as claimed in any one of claims 1 to 5 essentially in the form of the pure trans isomer. 1
Claim 10
Dependent Claim
21 words
A compound as claimed in any one of claims 1 to 5 essentially in the form of the pure cis isomer.
Claim 11
Dependent Claim
27 words
A compound of formula (I) as defined in any one of claims 1 to 9 for use in treatment of the human or animal body by therapy.
Claim 12
Dependent Claim
18 words
A compound as claimed in claim 10 for use in the treatment or prophylaxis of a protozoal infection.
Claim 13
Dependent Claim
16 words
A pharmaceutical formulation comprising a compound of formula (I) together with a pharmaceutically acceptable carrier therefor.
Claim 14
Dependent Claim
16 words
A pharmaceutical formulation comprising a compound of formula (I) together with a pharmaceutically acceptable carrier therefor.
Claim 15
Dependent Claim
16 words
A veterinary formulation comprising a compound of formula (I) together with a veterinarily acceptable carrier therefor.
Claim 16
Dependent Claim
16 words
A veterinary formulation comprising a compound of formula (I) together with a veterinarily acceptable carrier therefor.
Claim 17
Dependent Claim
113 words
A method for the preparation of a compound of formula (I) as defined in claim 1 which method comprises:- (a) hydrolysis of a compound of formula (II) wherein X is halogen and R is as defined in formula (I), (b) Hooker Oxidation of a compound of formula (III) wherein R is as defined in formula (I); (c) reacting a compound of formula (IV) wherein Y is halogeno, hydroxy, acetoxy or alkoxy with a cyclohexyl donor containing the moiety where R is as defined in formula (I) and, where desired, converting the group Y to a hydroxy group; (d) conversion of a compound of formula (V) wherein R is as defined in formula (I).
Claim 18
Dependent Claim
33 words
A method for the preparation of the trans isomer of a compound of formula (I) as defined in claim 1 which method comprises epimerisation of the corresponding cis isomer with concentrated sulphuric acid.
Claim 19
Dependent Claim
31 words
A compound of the formula (VIII) wherein R is as defined in any one of claims 1 to 9 and Y is a halogeno, acetoxy, benzoloxy or C 1-4 alkoxy group.
Claim 20
Dependent Claim
17 words
A compound of formula (I) as defined in claim 1 in combination with a second therapeutic agent.
Claim 21
Dependent Claim
18 words
A combination as claimed in claim 17 wherein the second therapeutic agent is an antimalarial or antiococcidial agent.
Claim 22
Dependent Claim
25 words
A pharmaceutical or veterinary formulation comprising a combination as defined in claim 17 or claim 18 together with a pharmaceutically or veterinarily acceptable carrier therefor.
References Cited (Backward Citations)
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