US 5,516,783 AGranted

4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonamide derivatives as antagonist of PAF

AssigneeBritish Biotech Pharmaceuticals Limited

InventorsMark Whittaker, Stephen A. Bowles, Andrew Miller

Life of this patent

Estimating the term…

Abstract

The present invention is directed to compounds of general formula I as well their pharmaceutically and veterinarily acceptable acid addition salts or hydrates thereof. The present invention is further directed to pharmaceutical and veterinary compositions containing the compounds of general formula I. The present compounds of general formula I are antagonist of platelet activating factor (PAF). Accordingly, the present invention is also directed to methods for preventing, treating or ameliorating in human or mammalian animals, various diseases or physiological conditions mediated by PAF.

Claims14

Dependent claims

A compound of general formula I:

##STR58## wherein:
R.sup.1 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkyrryl, --COC.sub.1 -C.sub.6 alkyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(COC.sub.1 -C.sub.6 alkyl) phenyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl)phenyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl or a group --D wherein D represents a group:
##STR59## wherein n is an integer from 0 to 3, and each of R.sup.3 and R.sup.4 is independently hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, halogen, --CN, --CO.sub.2 H, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --CONH.sub.2, --CONHC.sub.1 -C.sub.6 alkyl, --CONH(C.sub.1 -C.sub.6 alkyl).sub.2, --CHO, --CH.sub.2 OH, --CF.sub.3, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, --SO.sub.2 C.sub.1 -C.sub.6 alkyl, --NH.sub.2 or --NHCOMe;
R.sup.2 represents hydrogen, halogen, --C.sub.1 -C.sub.6 alkyl optionally substituted by one or more halogen atoms, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --C.sub.1 -C.sub.6 alkyl)N(C.sub.1 -C.sub.6 alkyl).sub.2, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)C.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)C.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.4 -C.sub.8 cycloalkenyl, a side chain of a naturally occurring amino acid, a group --D as defined above or a --(C.sub.1 -C.sub.6 alkyl)OD group wherein D is as defined above;
B represents
a) a --(CH.sub.2).sub.m X group wherein m is an integer from 0 to 2 and the group X represents a 5- or 6-membered heterocyclic ring, which heterocyclic ring may be optionally fused to a benzene ring or to a further 5-, 6- or 7-membered heterocyclic ring containing one or more nitrogen atoms wherein the latter heterocyclic ring may also contain an oxygen or sulfur atom, and wherein any of the rings may be optionally substituted with one or more substituents selected from the group consisting of hydrogen, halogen, --C.sub.1 -C.sub.4 perfluoroalkyl, hydroxyl, carbonyl, thiocarbonyl, carboxyl, --CONH.sub.2, a group --D wherein D is as defined above, --R.sup.5, --OR.sup.5, --SR.sup.5, --SOR.sup.5, --SO.sub.2 R.sup.5, --NHR.sup.5, --NR.sup.5 R.sup.5, --CO.sub.2 R.sup.5 and --CONHR.sup.5 wherein R.sup.5 is --C.sub.1 -C.sub.18 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --C.sub.3 -C.sub.8 cycloalkyl or --C.sub.4 -C.sub.8 cycloalkenyl each of which is optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxyl, amino, carboxyl, --C.sub.1 -C.sub.4 perfluoroalkyl, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, tetrazol-5-yl, a group --D wherein D is as defined above and a heteroaryl or heteroarylmethyl group;
b) a group Y, wherein Y is --CH.sub.2 OH, --CH.sub.2 OC(.dbd.O)R.sup.6, --CH.sub.2 OC(.dbd.O)C(.dbd.O)OR.sup.6, --CH.sub.2 OSO.sub.2 R.sup.6, --CH.sub.2 OP(.dbd.O)OR.sup.6 OR.sup.6, --NHC(C.dbd.O)OR.sup.6, --CH.sub.2 OC(.dbd.O)NHR.sup.6, --CH.sub.2 CO.sub.2 R.sup.6 or --CH.sub.2 OC(.dbd.O)CH.sub.2 SR.sup.6 group wherein R.sup.6 is, --C.sub.1 -C.sub.18 alkyl, --C.sub.2 -C.sub.20 alkenyl, --C.sub.2 -C.sub.18 alkynyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, a group D as defined above or a group --(CH.sub.2).sub.m X as defined above;
c) a --CH.sub.2 OC(.dbd.O)CHR.sup.2 Y group wherein R.sup.2 and Y are as defined above.

5 more elements

A compound selected from the group consisting of:

N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-le ucinol,
N-4-(1H-2-Methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-D-le ucinol,
N-Ethyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leu cinol,
N-Allyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leu cinol,
N-Propyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-le ucinol,
N-Benzyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-le ucinol,
N-4-Methoxybenzyl-N-4-(1H-2-methyl imidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-is oleucinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-ph enylalaninol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-va linol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-tr yptophanol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-me thioninol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-O-me thyl-L-tyrosinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-no rleucinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-ph enylglycinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-t- butylglycinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-D,L- ethylglycinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-D,L- allylglycinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-cy clopropylalaninol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-cy clopentylalaninol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-cy clohexylalaninol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-D-leucinol,
O-Ethanoyl-N-ethyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulp honyl-L-leucinol,
O-Ethanoyl-N-allyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulp honyl-L-leucinol,
O-Ethanoyl-N-propyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Ethanoyl-N-benzyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Ethanoyl-N-4-methoxybenzyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl) phenylsulphonyl-L-leucinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-isoleucinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-phenylalininol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-valinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-tryptophanol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-methioninol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-O'-methyl-L-tyrosinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-norleucinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-phenylglycinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-t-butylglycinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-D,L-ethylglycinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-D,L-allylglycinol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-cyclopropylalininol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-cyclopentylalininol,
O-Ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-cyclohexylalininol,
O-Octadecanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)pheny lsulphonyl-L-leucinol,
O-Propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsu lphonyl-L-leucinol,
O-2-Furoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Ethyloxaloyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)pheny lsulphonyl-L-leucinol,
O-Benzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulp honyl-L-leucinol,
O-2-Acetoxybenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)p henylsulphonyl-L-leucinol,
O-Propanoyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-L -leucinol,
O-Propanoyl-N-ethyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Propanoyl-N-allyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Propanoyl-N-methoxybenzyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)p henylsulphonyl-L-leucinol,
O-Propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsu lphonyl-L-isoleucinol,
O-Propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsu lphonyl-L-cyclopentylalininol,
O-Butanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Pentanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsu lphonyl-L-leucinol,
O-Hexanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Octanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Decanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-Dodecanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenyls ulphonyl-L-leucinol,
O-Tetradecanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phen ylsulphonyl-L-leucinol,
O-Hexadecanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)pheny lsulphonyl-L-leucinol,
O-2-Thiophenecarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethy l)phenylsulphonyl-L-leucinol,
O-2-Tetrahydrofuroyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl )phenylsulphonyl-L-leucinol,
O-2-Pyridinecarbonyl-N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl )phenylsulphonyl-L-leucinol,
O-3-Pyridinecarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl )phenylsulphonyl-L-leucinol,
O-4-Pyridinecarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl )phenylsulphonyl-L-leucinol,
O-3-Quinolinecarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethy l)phenylsulphonyl-L-leucinol,
O-2-Trifluoromethylbenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinyl methyl)phenylsulphonyl-L-leucinol,
O-2-Bromobenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phe nylsulphonyl-L-leucinol,
O-3-Chlorobenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)ph enylsulphonyl-L-leucinol,
O-4-Methoxybenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)p henylsulphonyl-L-leucinol,
O-4-Fluorobenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)ph enylsulphonyl-L-leucinol,
O-3,4-Dimethoxybenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmeth yl)phenylsulphonyl-L-leucinol,
O-3-Chloro-4-methoxybenzoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridiny lmethyl)phenylsulphonyl-L-leucinol,
O-2,2-Dimethylpropanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmet hyl)phenylsulphonyl-L-leucinol,
O-2-(3,4-Dimethoxyphenylmercapto)ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[ 4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-Retinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-2-(4-Methoxyphenyl)ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridi nylmethyl)phenylsulphonyl-L-leucinol,
O-2-(3,4-Dimethoxyphenyl)ethanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5c]pyr idinylmethyl)phenylsulphonyl-L-leucinol,
O-3-(4-Methoxyphenyl)propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyrid inylmethyl)phenylsulphonyl-L-leucinol,
O-3-(3,4-Dimethoxyphenyl)propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]p yridinylmethyl)phenylsulphonyl-L-leucinol,
O-3-(3-Chloro-4-methoxyphenyl)propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4, 5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-3-(Pyridin-3-yl)propanoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridiny lmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-L-leucinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c ]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-(N',N'-Dibenzyl)-L-leucinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyrid inylmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)glycinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5c]pyr idinylmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-D-leucinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c ]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-L-phenylalininoyl-N-methyl-N-4-(1H-2-methylimidazo [4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-(N',N'-dibenzyl)glycinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridiny lmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-L-norleucinoyl-N-methyl-N-4-(1H-2-methylimidazo[4, 5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Butoxycarbonyl)-L-leucinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5c]pyr idinylmethyl)phenylsulphonyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-L-valinoyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c] pyridinylmethyl)phenylsulphoriyl-L-leucinol,
O-(N'-Benzyloxycarbonyl)-L-phenylglycinoyl-N-methyl-N-4-(1H-2-methylimidazo [4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-Diethoxyphosphoryl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl )phenylsulphonyl-L-leucinol,
O-Dimethoxyphosphoryl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethy l)phenylsulphonyl-L-leucinol,
O-Diphenoxyphosphoryl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c ]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-Diisopropoxyphosphoryl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylme thyl)phenylsulphonyl-L-leucinol,
O-Methylsulphonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)ph enylsulphonyl-L-leucinol,
O-Ethylsulphonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phe nylsulphonyl-L-leucinol,
O-Propylsulphonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)ph enylsulphonyl-L-leucinol,
O-Phenylsulphonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)ph enylsulphonyl-L-leucinol,
O-4-Methylphenylsulphonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylm ethyl)phenylsulphonyl-L-leucinol,
O-Benzylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmeth yl)phenylsulphonyl)-L-leucinol,
O-4-Ethoxycarbonylpiperazinecarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c ]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-5-Ethyl-1,3,4-thiadiazol-2-ylaminocarbonyl-N-methyl-N-4-(1H-2-methylimida zo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-Pyridin-2-ylmethylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5c]pyr idinylmethyl)phenylsulphonyl-L-leucinol,
O-Octadecylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylm ethyl)phenylsulphonyl-L-leucinol,
O-Methylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmeth yl)phenylsulphonyl-L-leucinol,
O-Ethylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethy l)phenylsulphonyl-L-leucinol,
O-n-Propylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylme thyl)phenylsulphonyl-L-leucinol,
O-i-Propylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylme thyl)phenylsulphonyl-L-leucinol,
O-n-Pentylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylme thyl)phenylsulphonyl-L-leucinol,
O-n-Hexylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmet hyl)phenylsulphonyl-L-leucinol,
O-n-Octylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmet hyl)phenylsulphonyl-L-leucinol,
O-n-Decylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmet hyl)phenylsulphonyl-L-leucinol,
O-n-Dodecylamino carbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsul phonyl-L-leucinol,
O-n-Tetradecylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridin ylmethyl)phenylsulphonyl-L-leucinol,
O-n-Hexadecylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridiny lmethyl)phenylsulphonyl-L-leucinol,
O-t-Butylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmet hyl)phenylsulphonyl-L-leucinol,
O-Pyridin-2-ylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridin ylmethyl)phenylsulphonyl-L-leucinol,
O-Pyridin-4-ylmethylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]py ridinylmethyl)phenylsulphonyl-L-leucinol,
O-Pyridin-3-ylmethylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5c]pyr idinylmethyl)phenylsulphonyl-L-leucinol,
O-4-Methoxyphenylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]pyrid inylmethyl)phenylsulphonyl-L-leucinol,
O-3,4-Dimethoxybenzylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4,5-c]p yridinylmethyl)phenylsulphonyl-L-leucinol,
O-2-(4-Methoxyphenyl)ethylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidazo[4, 5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-2-(3,4-Dimethoxyphenyl)ethylaminocarbonyl-N-methyl-N-4-(1H-2-methylimidaz o[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-3-(3,4-Dimethoxyphenyl)propylaminocarbonyl-N-methyl-N-4-(1H-2-methylimida zo[4,5-c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
O-3-(Pyridin-3-yl)propylaminocarbonyl-(N-methyl-N-4-(1H-2-methylimidazo[4,5 -c]pyridinylmethyl)phenylsulphonyl-L-leucinol,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-2-th ienylmethylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-tetr ahydrofurfurylamine,
N-4-(1H-2-Methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-2-(N'-methylp yrrol-2-yl)ethylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(4- fluorophenyl)-1-(2-thienyl)methylamine,
N-4-(1H-2-Methyl imidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(2-thienyl)propylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(2- furyl)-3-methylbutylamine,
N-4-(1H-2-Methylbenzimidazolylmethyl)phenylsulphonyl-1-(2-benzothiazolyl)-3 -methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(2- thienyl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(p yridin-3-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(N '-methyl-2-pyrrolyl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(py razin-2-yl)-3-methylbutylainine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(6 -methylpyrazin-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(6 -ethylpyrazin-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(6 -ethyl-1,2-pyridazin-3-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(2 -ethyl-1,3-pyrimidin-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(1 ,3-dithian-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(2 -thienyl)pentylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(4 -fluorophenyl)-1-(2-furyl)methylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-2(4- methoxyphenyl)-1-(2-furyl)ethylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(p yridin-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(2 -methoxypyridin-3-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(p yridin-3-ylmethyl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(2 -benzo[b]thienyl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(3 -methylisoxazol-5-ylmethyl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylbenzimidazolylmethyl)phenylsulphonyl-1-(3-methyl-1 ,2,4-oxadiazol-5-yl )-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(3 -ethyl-1,2,4-oxadiazol-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1-(3 -octadecyl-1,2,4-oxadiazol-5-yl )-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(3- propyl-1,2,4-oxadiazol-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(3- n-butyl-1,2,4-oxadiazol-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(3- phenyl-1,2,4-oxadiazol-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(3- benzyl-1,2,4-oxadiazol-5-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(5- methyl-1,3,4-oxadiazol-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(5- ethyl-1,3,4-oxadiazol-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(5- propyl-1,3,4-oxadiazol-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-1(5- phenyl-1,3,4-oxadiazol-2-yl)-3-methylbutylamine,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-.bet a.-alanine ethyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3-am ino-5-methylhexanoic acid ethyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3-am ino-5-methylhexanoic acid isopropyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3-am ino-5-methylhexanoic acid n-butyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3-am ino-5-methylhexanoic acid benzyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3ami no4-phenylbutanote acid ethyl ester,
N-Methyl-N-4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonyl-3-am ino-4-(4-methoxyphenyl)butanoic acid ethyl ester,
and a salt of a compound thereof.

170 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound of general formula I:

##STR58## wherein:
R.sup.1 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkyrryl, --COC.sub.1 -C.sub.6 alkyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(COC.sub.1 -C.sub.6 alkyl) phenyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl)phenyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl or a group --D wherein D represents a group:
##STR59## wherein n is an integer from 0 to 3, and each of R.sup.3 and R.sup.4 is independently hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, halogen, --CN, --CO.sub.2 H, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --CONH.sub.2, --CONHC.sub.1 -C.sub.6 alkyl, --CONH(C.sub.1 -C.sub.6 alkyl).sub.2, --CHO, --CH.sub.2 OH, --CF.sub.3, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, --SO.sub.2 C.sub.1 -C.sub.6 alkyl, --NH.sub.2 or --NHCOMe;
R.sup.2 represents hydrogen, halogen, --C.sub.1 -C.sub.6 alkyl optionally substituted by one or more halogen atoms, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --C.sub.1 -C.sub.6 alkyl)N(C.sub.1 -C.sub.6 alkyl).sub.2, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)C.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)C.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.4 -C.sub.8 cycloalkenyl, a side chain of a naturally occurring amino acid, a group --D as defined above or a --(C.sub.1 -C.sub.6 alkyl)OD group wherein D is as defined above;
B represents
a) a --(CH.sub.2).sub.m X group wherein m is an integer from 0 to 2 and the group X represents a 5- or 6-membered heterocyclic ring, which heterocyclic ring may be optionally fused to a benzene ring or to a further 5-, 6- or 7-membered heterocyclic ring containing one or more nitrogen atoms wherein the latter heterocyclic ring may also contain an oxygen or sulfur atom, and wherein any of the rings may be optionally substituted with one or more substituents selected from the group consisting of hydrogen, halogen, --C.sub.1 -C.sub.4 perfluoroalkyl, hydroxyl, carbonyl, thiocarbonyl, carboxyl, --CONH.sub.2, a group --D wherein D is as defined above, --R.sup.5, --OR.sup.5, --SR.sup.5, --SOR.sup.5, --SO.sub.2 R.sup.5, --NHR.sup.5, --NR.sup.5 R.sup.5, --CO.sub.2 R.sup.5 and --CONHR.sup.5 wherein R.sup.5 is --C.sub.1 -C.sub.18 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --C.sub.3 -C.sub.8 cycloalkyl or --C.sub.4 -C.sub.8 cycloalkenyl each of which is optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxyl, amino, carboxyl, --C.sub.1 -C.sub.4 perfluoroalkyl, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, tetrazol-5-yl, a group --D wherein D is as defined above and a heteroaryl or heteroarylmethyl group;
b) a group Y, wherein Y is --CH.sub.2 OH, --CH.sub.2 OC(.dbd.O)R.sup.6, --CH.sub.2 OC(.dbd.O)C(.dbd.O)OR.sup.6, --CH.sub.2 OSO.sub.2 R.sup.6, --CH.sub.2 OP(.dbd.O)OR.sup.6 OR.sup.6, --NHC(C.dbd.O)OR.sup.6, --CH.sub.2 OC(.dbd.O)NHR.sup.6, --CH.sub.2 CO.sub.2 R.sup.6 or --CH.sub.2 OC(.dbd.O)CH.sub.2 SR.sup.6 group wherein R.sup.6 is, --C.sub.1 -C.sub.18 alkyl, --C.sub.2 -C.sub.20 alkenyl, --C.sub.2 -C.sub.18 alkynyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, a group D as defined above or a group --(CH.sub.2).sub.m X as defined above;
c) a --CH.sub.2 OC(.dbd.O)CHR.sup.2 Y group wherein R.sup.2 and Y are as defined above.

5 more elements