Aromatic compounds

Claim 2

1) A compound of the formula (I): or a salt, ester or amide thereof; wherein R 1 is a C 1-7 bivalent aliphatic hydrocarbon group or a single bond; R 2 and R 3 are the same or different and are each hydrogen, C 1-4 alkyl or taken together with the nitrogen comprise a nitrogen-containing heterocyclic ring having four to six ring members; R 4 is hydrogen, halogen, hydroxy, cyano, C 1-4 acyloxy, C 1-4 alkoxy or C 1-4 alkyl optionally substituted by one to three halogen atoms; X is -N= or -CH=; and A and B each represent hydrogen atoms or -CA-CB represents -C=C-.

Claim 3

2) A compound according to claim 1 of the formula (II) or a salt, ester or amide thereof, wherein R 1 to R 41 X, A and B are as defined in relation to claim 1.

Claim 4

3) A compound according to either claim 1 or claim 2 wherein R 1 is a group (CH 2 ) n where n is an integer 0 to 7, or a group (CH 2 ) a CH=CH(CH 2 ) b wherein a and b are independently 0 to 5 and the sum of a and b does not exceeed 5.

Claim 5

4) A compound according to any of claims 1 to 3 of the formula (IIIa) or (IIIb) or a salt, ester or amide thereof, wherein R 1 is (CH 2 ) n , where n is an integer 1 to 7, or (CH 2 ) a CH:CH-(CH 2 ) b , where a and b are independently 0 to 5 and the sum of a and b does not exceed 5; R 2 and R 3 are the same or different and are hydrogen, lower alkyl (1 to 4 carbons) or taken together with the nitrogen comprise a nitrogen containing heterocyclic ring (of four to six ring members) such as pyrrolidino, piperidino or morpholino; and R 4A is hydrogen, halogen such as Br or Cl, lower alkyl (1 to 4 carbons) or lower alkoxy (1 to 4 carbons).

Claim 6

5) A compound according to any of claims 1 to 4, wherein R 1 is (CH 2 ) 2 or CH=CH, NR 2 R 3 is a pyrrolidino group or a dimethylamino group and R 4 is methyl, trifluoromethyl, methoxy, bromo or chloro.

Claim 7

6) A compound according to any one of claims 1 to 5 of the formula (IV): or a salt, ester or amide thereof; wherein R 1 to R 4 are as hereinbefore defined.

Claim 8

7) A compound according to claim 6 wherein R 1 is a single bond, CH=CH or CH 2 CH 2 ; NR 2 R 3 is pyrrolidino and R 4 is methyl or trifluoromethyl.

Claim 9

8) A compound according to any one of claims 1 to 7 wherein CA-CB represents a double bond and the group CH 2 NR 2 R 3 is trans to the X-containing ring.

Claim 10

9) A compound according to any one of claims 1 to 5 of the formula (V): or a salt, ester or amide thereof, wherein R 1 to R 4 are as hereinbefore defined.

Claim 11

10) A compound according to claim 9 wherein R 1 is a single bond, CH=CH or CH 2 CH 2 , N R Z R 3 is dimethylamino and R 4 is chlorine or bromine.

Claim 12

11) A compound according to claim 1 selected from: (E)-3-(6-(3-pyrrolidino-1-(4-tolyl)prop-1E-enyl)-2-pyridyl)acrylic acid 3-(6-(3-pyrrolidino-1-(4-tolyl)prop-lE-enyl)-2-pyridyl)propionic acid (E)-3-(6-(3-dimethylamino-l-(4-tolyl)prop-lE-enyl)-2-pyridyl)acrylic acid (E)-3-(6-(3-pyrrolidino-1-(4-trifluoromethylphenyl)prop-1E-enyl)-2-pyridyl)acrylic acid (E)-3-(6-(3-pyrrolidino-1-(4-methoxyphenyl)prop-1E-enyl)-2-pyridyl)acrylic acid (E)-3-(6-(1-phenyl-3-pyrrolidinoprop-1-E-enyl)-2-pyridyl)acrylic acid (E)-3-(6-(1-(4-chlorophenyl)-3-pyrrolidinoprop-1E-enyl)-2-pyridyl)acrylic acid 6-(3-pyrroUdino-1-(4-tolyl)prop-1E-enyl)-pyridine-2-carboxylic acid (E)-3-(3-pyrrolidino-l-(4-tolyl)prop-l-enyl)benzoic acid (E)-3-(3-pyrrolidino-l-(4-tolyl)prop-1-enyl)cinnamic acid (E)-3-((E)-3-pyrrolidino-1-(4-methoxyphenyl)prop-1-enyl))cinnamic acid (E)-3-((E)-3-dimethylamino-l-(4-tolyl)prop-l-enyl))cinnamic acid (E)-3-(3-(3-pyrrolidino-1-(4-tolyl)prop-1-enyl)phenyl)propionic acid or a salt, ester or amide thereof.

Claim 13

12) A method for the preparation of a compound of the formula (I), as defined in relation to claim 1 which comprises: a) The reaction of a compound of the formula (VI) or an ester thereof with an amine HNR 2 R 3 wherein X, A, B and R 1 to R 4 are as hereinbefore defined and L is a leaving group; b) When it is required to prepare a compound of the formula (I) wherein R 1 is (CH 2 ) 0 and A and B are hydrogen, the reaction of a compound of the formula (VII) wherein R 2 , R 3 , R 4 , X, A 4 and B are as hereinbefore defined and R 5 is a halogen atom, with a C 1-6 alkyl lithium compound followed by treatment with carbon dioxide; c) When it is required to prepare a compound of the formula (I) wherein R 1 is (CH 2 ) a CH=CH(CH 2 ) b and a is 0, the reaction of a compound of the formula (VIII): wherein R 2 , R 3 , R 4 , A and B are as hereinbefore defined, with a Wittig reagent suitable for attaching the side chain CH=CH(CH 2 ) b COR 6 , wherein COR 6 is an acid, ester or amide group as hereinbefore defined, followed by deprotection of the carboxy group if desired; d) When it is required to prepare a compound of the formula (I) wherein CA-CB represents a double bond: i) The reaction of an ester, amide or carboxylic acid salt of a compound of the formula (IX): with a Wittig reagent suitable for attaching the side chain =CHCH 2 NR 2 R 3 wherein X and R 1 to R 4 are as hereinbefore defined, followed by deprotection of the carboxy group if desired; ii) The elimination of R OH from a compound of the formula (X): or an ester or amide thereof, wherein X, R 1 to R 4 are as hereinbefore defined and R 7 is hydrogen or C 1-4 acyl; iii) The reaction of a compound of the formula (XI): with an amine HNR 2 R 3 , wherein X, R 1 to R 4 are as hereinbefore defined and R 8 is a C 1-4 acyloxy group. e) and thereafter, optionally converting one compound of the formula (I) to another compound of the formula (I) by methods well known to those skilled in the art.

Claim 14

13) A pharmaceutical formulation which comprises a compound of the formula (I) together with one or more pharmaceutically acceptable carries thereof and, optionally, any other therapeutic ingredients.

Claim 15

13) A pharmaceutical formulation which comprises a compound of the formula (I) together with one or more pharmaceutically acceptable carries thereof and, optionally, any other therapeutic ingredients.

Claim 16

14) A compound of the formula (0, as defined according to any one of claims 1 to 11, for use in medicine.

Claim 17

15) Novel chemical intermediates of the formula (VI) to (XXIII) as hereinbefore defined.

Claim 18

15) Novel chemical intermediates of the formula (VI) to (XXIII) as hereinbefore defined.