Patent US3177720A successfully refreshed from Google Patents.
Patent EP0043292A2 successfully refreshed from Google Patents.
EP0043292A2
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Prostaglandins
Assignee: BTG International Ltd
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Filing: 1981-07-01
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Granted: —
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Expires: 2001-07-01
Abstract
Abstract Novel compounds have a formula (I) wherein represents a bicyclo (2,2,1) hept-2Z-ene, bicyclo (2,2,1) heptane, 7-oxabicyclo (2,2,1) hept-2Z-ene, 7-oxabicyclo (2,2,1) heptane, bicyclo (2,2,2) oct-2Z-ene or bicyclo (2,2,2) octane substituted at the 5-position by the group R 1 and at the 6-position by the group C(R 2 )=NR, a 6,6-dimethyl-bicyclo (3,1,1) heptane substituted at the 5- position by the group R' and at the 6-position by the group C(R 2 )=NR or at the 5-position by the group C(R 2 )=NR and at the 6-position by the group R 1 , a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R 1 and at the 5-position by the group C(R 2 )=NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R 1 and at the 2-position by the group C(R 2 )=NR, R 1 is a 6-carboxyhex-2-enyl group or a modification thereof as defined herein, R 2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group -OR 3 , -OR 4 , -A-R 3 or -N=R 5 in which A is -NH-, -NH.CO-, -NH.CO.CH 2 N(R 6 )-, -NH.SO 2 -, -NH.CO.NH or -NH.CS.NH- and wherein R 3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, R 4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom by an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R 5 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R 6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group -OR 3 , -NH.COR 3 or-NH.CO.NHR3 then excludes bicyclo (2,2,1) hept-2Z-enes and bicyclo (2,2,1) heptanes. The compounds are of value for use in phar. maceutical compositions particularly in the context of the inhibition of thromboxane activity.
Inventors
- 👤 Robert Leslie Jones
- 👤 Norman Happer Wilson
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 07:09
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A61; A61P; A61P11/00; A61P11/08; A61P29/00; A61P37/00; A61P37/08; A61P43/00; A61P7/00; A61P7/02; A61P9/00; A61P9/08; C07C; C07C251/00; C07C251/72; C07C403/00; C07C403/20; C07C405/00; C07C405/0008; C07C405/0041; C07C405/005; C07C405/0058; C07C405/0066; C07C405/0075; C07C405/0091; C07C45/00; C07C45/27; C07C45/30; C07C45/305; C07C45/44; C07C47/00; C07C47/20; C07C47/225; C07C47/38; C07C47/47; C07C57/00; C07C57/26; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
256 words
A compound of formula (I) wherein represents one of the divalent cyclic groups the letters a and b indicating in each case the points of attachment of the substituents R 1 and C(R 2 )=NR , respectively, R 1 is a 6-carboxyhex-2-enyl group or a modification thereof as defined herein, R is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group -OR 3 , -OR 4 , -A-R 3 or N=R 5 in which A is -NH-, -NH.CO-, -NH.CO.CH 2 N(R 6 )-, -NH.SO 2 -, -NH.CO.NH- or -NH.CS.NH- and wherein R 3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an an oxygen or sulphur atom by an aromatic group, R 4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom by an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R 6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group -OR 3 , -NH.COR 3 or NH.CO.NHR 3 then excludes the divalent cyclic groups and pharmaceutically acceptable bioprecursors of such compounds of formula (I).
Claim 2
Dependent Claim
256 words
A compound of formula (I) wherein represents one of the divalent cyclic groups the letters a and b indicating in each case the points of attachment of the substituents R 1 and C(R 2 )=NR , respectively, R 1 is a 6-carboxyhex-2-enyl group or a modification thereof as defined herein, R is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group -OR 3 , -OR 4 , -A-R 3 or N=R 5 in which A is -NH-, -NH.CO-, -NH.CO.CH 2 N(R 6 )-, -NH.SO 2 -, -NH.CO.NH- or -NH.CS.NH- and wherein R 3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an an oxygen or sulphur atom by an aromatic group, R 4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom by an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R 6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group -OR 3 , -NH.COR 3 or NH.CO.NHR 3 then excludes the divalent cyclic groups and pharmaceutically acceptable bioprecursors of such compounds of formula (I).
Claim 3
Dependent Claim
28 words
A compound according to Claim 1, in which the divalent cyclic group is other than a 6,6-dimethyl-bicyclo [3,1,1] heptane ring system having the group R at the 3-position.
Claim 4
Dependent Claim
18 words
A compound according to Claim 1 or 2, in which the divalent cyclic group is a bridged group.
Claim 5
Dependent Claim
24 words
A compound according to Claim 1 which contains a bicyclo [2,2,1] heptane, bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,2] octane or bicyclo [2,2,2] oct-2Z-ene ring system.
Claim 6
Dependent Claim
21 words
A compound according to Claim 1 which contains a 6,6-dimethyl-bicyclo [3,1,1] heptane ring system having the group R at the 3-position.
Claim 7
Dependent Claim
26 words
A compound according to any of Claims 1 to 5 in which R is a 6-carboxyhex-2Z-enyl group or a derivative thereof formed at the carboxy group.
Claim 8
Dependent Claim
26 words
A compound according to any of Claims 1 to 5, in which R is a 6-carboxyhexyl group or a derivative thereof formed at the carboxy group.
Claim 9
Dependent Claim
22 words
A compound according to any of Claims 1 to 7, in which R is a group terminating in a free carboxy group.
Claim 10
Dependent Claim
24 words
A compound according to any of Claims 1 to 7, in which R is a group terminating in a carboxy group in derivative form.
Claim 11
Dependent Claim
22 words
A compound according to Claim 9, in which the derivative is an amide, an ester or a salt of the carboxy group.
Claim 12
Dependent Claim
20 words
A compound according to any of the preceding claims, in which R 2 is hydrogen or an aliphatic hydrocarbon group.
Claim 13
Dependent Claim
23 words
A compound according to Claim 11, in which R 2 is hydrogen or an aliphatic hydrocarbon group of 1 to 3 carbon atoms.
Claim 14
Dependent Claim
12 words
A compound according to Claim 12, in which R 2 is methyl.
Claim 15
Dependent Claim
31 words
A compound according to any of the preceding claims, in which R is a group -OR 3 , -NH.COR , -NH.SO 2 R 3 , NH.CO.NHR 3 or NH.CS.NHR 3 .
Claim 16
Dependent Claim
19 words
A compound according to Claim 14, in which R is a group NH.COR 3 or -NH.CS. NHR 3 .
Claim 17
Dependent Claim
37 words
A compound according to any of the preceding claims, in which R 3 and R are limited to aromatic groups or aliphatic hydrocarbon groups substituted directly or through an oxygen or sulphur atom by an aromatic group.
Claim 18
Dependent Claim
47 words
A compound according to Claim 16, which contains a group R or R 5 which is an unsubstituted or substituted phenyl or pyridyl group or an aliphatic hydrocarbon group substituted either directly or through an oxygen or sulphur atom by one or more of such aromatic groups.
Claim 19
Dependent Claim
40 words
A compound according to Claim 17, in which R is a group -OR 3 with R 3 being an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by a phenyl group or a substituted phenyl group.
Claim 20
Dependent Claim
70 words
A compound according to Claim 17 or 18, in which the aliphatic hydrocarbon group is of 1 to 3 carbon atoms when substituted directly and of 2 or 3 carbon atoms when substituted through an oxygen or sulphur atom. 20. A compound according to Claim 16, 17, 18 or 19 in which the group R 3 or R is an aliphatic hydrocarbon group substituted by at least two aromatic groups.
Claim 21
Dependent Claim
40 words
A compound according to Claim 17, in which R is a group -NH.COR 3 , -NH.SO 2 R 3 , -NH.CO.NHR 3 or -NH.CS.NHR 3 with R 3 being a phenyl group, a substituted phenyl group or a pyridyl group.
Claim 22
Dependent Claim
32 words
A compound according to Claim 17, in which R is a group -NH.CO.NHR 3 or -NH.CS.NHR 3 with R 3 being a phenyl group, a substituted phenyl group or a pyridyl group.
Claim 23
Dependent Claim
41 words
A compound according to any of Claims 17 to 22, in which R is or contains a phenyl group or a phenyl group substituted by one or more groups which are selected from alkoxy, halogen, halogen- substituted alkyl and alkyl groups.
Claim 24
Dependent Claim
37 words
A compound according to Claim 23, in which R 3 is or contains a phenyl group or a phenyl group substituted by one or more groups which are selected from methoxy, fluoro, chloro, bromo, trifluoromethyl and methyl.
Claim 25
Dependent Claim
92 words
A compound according to Claim 17, 18 or 19, or Claim 20, 23 or 24 as dependent on Claim 17, 18 or 19, in which the substituting phenyl group is itself substituted by substituents at one or more of the ortho and para positions when R 3 is an aliphatic hydrocarbon group directly substituted by the substituted phenyl group, and by substituents at one or more of the ortho and meta positions when R 3 ..is an aliphatic hydrocarbon group substituted by the substituted phenyl group through an oxygen or sulphur atom.
Claim 26
Dependent Claim
40 words
A compound according to Claim 21 or 22 or Claim 23 or 24 as dependent on Claim 21 or 22, in which R 3 is a substituted phenyl group having.substitution at one or more of the meta and para positions.
Claim 27
Dependent Claim
45 words
A compound according to Claim 1, in which the compound of formula (I) is a bicyclo [2,2,1] heptane, bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,2] octane or bicyclo [2,2,2] oct-2Z-ene substituted at the 5-position by a 6-carboxyhex-2Z-enyl group and at the 6-position by a l'-[N-(phenylthiocarbamoyl)-hydrazono] ethyl group.
Claim 28
Dependent Claim
39 words
A compound according to Claim 1, in which the compound of formula (I) is a bicycle [2,2,2] octane or bicyclo [2,2,2] oct-2Z-ene substituted at the 5-position by a 6-carboxyhex-2Z-enyl group and at the 6-position by a l'-[N-(phenylcarbamoyl)-hydrazono] ethyl group.
Claim 29
Dependent Claim
41 words
A compound according to Claim 1, in which the compound of formula (I) is a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by a 1'-[N-(phenylthiocarbamoyl)-hydrazono] ethyl group or a 1'-[N-(phenylcarbamoyl)-hydrazono] ethyl group and at the 3- position by a 6-carboxyhex-2'Z-enyl group.
Claim 30
Dependent Claim
28 words
A compound. according to any of Claims 1 to 6 and 8 to 29, in which the configuration about any double bond in the group R is cis.
Claim 31
Dependent Claim
23 words
A compound according to any of the preceding claims, in which groups R 1 and C(R 2 )=NR are in a trans relationship.
Claim 32
Dependent Claim
63 words
A compound according to any of the preceding claims, in which the divalent cyclic group has the 5-endo, 6-exo configuration when it is a bicyclo [2,2,1] heptane, bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene or bicyclo [2,2,2] oct-2Z-ene, the 2α, 3β, 6α configuration when it is a 6,6-dimethyl-bicyclo [3,1,1] heptane and the la, 2a, 3β configuration when it is a 1-hydroxycyclopentane.
Claim 33
Dependent Claim
4 words
5-endo(6'-Carboxyhex-2'Z-enyl)-6-exo- {1'-[N-(phenylthiocarbamoyl)-hydrazono]-ethyl}-bicyclo [2,2,1] heptane.
Claim 34
Dependent Claim
4 words
5-endo(6'-Carboxyhex-2'Z-enyl)-6-exo- {1'-[N-(phenylthiocarbamoyl)-hydrazono]-ethyl}-bicyclo [2,2,1] heptane.
Claim 35
Dependent Claim
15 words
A compound according to Claim 1 as described in any of Examples 1 to 17.
Claim 36
Dependent Claim
71 words
A process for the preparation of a compound (I) according to Claim 1 which comprises reacting a compound of formula (II) with a reagent RNH 2 , Y being either R 1 as defined in Claim 1 or a precursor for R and the other symbols being as defined in Claim 1, and where appropriate converting the group Y in the resultant product into the group R of the compound (I).
Claim 37
Dependent Claim
46 words
A process according to Claim 35, which Y is a group terminating in a free carboxy group when R is a group terminating in a carboxy group in derivative form, and vice-versa, and Y is converted to R 1 as the final step of the process.
Claim 38
Dependent Claim
116 words
A compound suitable for use in the preparation of a compound according to Claim 1 having the formula wherein R 1 and R 2 are as defined in claim 1, (but with the letters a and b indicating in each case the points of attachment of the substituents R and and excluding the bicyclo [2,2,1] heptane and bicyclo [2,2,1] hept-2Z-ene ring systems), Y is either R or a precursor therefor, and either V and W together are a carbonyl group or when R is other than hydrogen, V is hydrogen and W is a hydroxy group, with the proviso that when R is hydrogen then the divalent cyclic group may not be a 7-oxa-bicyclo [2,2,1] heptane.
Claim 39
Dependent Claim
29 words
A compound according to Claim 37, in which R is a 6-carboxyhex-2Z-enyl group or a 6-carboxyhexyl group or a derivative of such groups formed at the carboxy group thereof.
Claim 40
Dependent Claim
16 words
A compound according to Claim 37 or 38, in which the group is a formyl group.
Claim 41
Dependent Claim
32 words
A compound according to Claim 37 or 38, in which the group is a group C(R 2 )=0 with R 2 being an aliphatic hydrocarbon group of 1 to 3 carbon atoms.
Claim 42
Dependent Claim
15 words
A compound according to Claim 37 as described in any of Examples 4 to 11.
Claim 43
Dependent Claim
28 words
A pharmaceutical composition comprising a compound according to any of Claims 1 to 34 as an active ingredient thereof in combination with a physiologically acceptable diluent or carrier.
Claim 44
Dependent Claim
16 words
A method of treatment which comprises administering to a patient a compound according to Claim 1.
References Cited (Backward Citations)
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