Cyclosporin compounds, their preparation and the pharmaceutical compositions which contain them

A compound selected from:

• -[(R)-2-aminoethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-methylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-ethylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-i-propylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-t-butylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-phenylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-benzylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-methyl-N-ethylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-( N-methyl-N-allylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-methyl-N-phenylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N-methyl-N-benzylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N,N-di-i-propylamino)ethylthio-Sar]3-cyclosporin A;
• -[(R)-2-(N,N-diallylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-aminopropylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-ethylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-i-propylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-t-butylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-phenylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-benzylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-ethylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-i-propylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-t-butylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-allylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-phenylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N-methyl-N-benzylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N,N-dimethylamino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N,N-diethylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N,N-di-i-propylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N,N-diallylamino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(1-piperidyl)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-aminobutylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-ethylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-i-propylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-t-butylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-phenylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-benzylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-ethylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-i-propylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-t-butylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-allylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-phenylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N-methyl-N-benzylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N,N-dimethylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N,N-diethylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N,N-di-i-propylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(N,N-diallylamino)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-4-(1-piperidyl)butylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-amino-2-methylpropylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N,N-dimethylamino)-2-methylpropylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(N,N-diethylamino)-2-methylpropylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(1-piperidyl)-2-methylpropylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-amino-3-methylbutylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N,N-dimethylamino)-3-methylbutylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(N,N-diethylamino)-3-methylbutylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(1-piperidyl)-3-methylbutylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(1-morpholino)ethylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-2-(1-azetidino)ethylthio-Sar].sup.3 -cyclosporin A;
• -{(R)-2-[1-(methylpiperazino)]ethylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-2-[1-(4-phenylpiperazino)]ethylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-2-[1-(4-benzylpiperazino)]ethylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-2-[1-(4-methyl-1,2,3,6-tetrahydropyridyl)]ethylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-2-[1-(4-phenyl-1,2,3,6-tetrahydropyridyl)]ethylthio-Sar}.sup.3 -cyclosporin A;
• -[(R)-3-(1-morpholino)propylthio-Sar].sup.3 -cyclosporin A;
• -[(R)-3-(1-(azetidino)propylthio-Sar].sup.3 -cyclosporin A;
• -{(R)-3-[1-(4-methylpiperazino)]propylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-3-[1-(4-phenylpiperazino)]propylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-3-[1-(4-benzylpiperazino)]propylthio-Sar}.sup.3 -cyclosporin A;
• -{(R)-3-[1-(4-methyl-1,2,3,6-tetrahydropyridyl)]propylthio-Sar}.sup.3 -cyclosporin A;
• and
• -{(R)-3-[1-(4-methyl-1,2,3,6-tetrahydropyridyl)]propylthio-Sar}.sup.3 -cyclosporin A;
• therefor their pharmaceutically acceptable salts.

A cyclosporin compound of formula (I) ##STR6## in which:

• Alk represents a C.sub.2-6 straight chain or branched alkylene radical or a C.sub.3-6 cycloalkylene radical, and
• R represents
• a carboxyl radical,
• an alkyloxycarbonyl radical,
• an 13 NR.sub.1 R.sub.2 radical in which R.sub.1 and R.sub.2, which are identical or different, represent a hydrogen atom or an alkyl, C.sub.3-6 cycloalkyl or optionally substituted phenyl radical, wherein said phenyl radical may be substituted by a halogen atom, or an alkyloxy, alkyloxycarbonyl, amino, alkylamino or dialkylamino radical, or represent a benzyl or heterocyclyl radical, wherein the heterocyclyl radical is saturated or unsaturated and contains 5 or 6 ring members and from 1 to 3 heteroatoms;
• or in which R.sub.1 and R.sub.2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated heterocycle containing 5 to 6 ring members, wherein said saturated or unsaturated heterocycle may optionally contain a further heteroatom selected from nitrogen, oxygen and sulphur atoms, and wherein said saturated or unsaturated heterocycle is optionally substituted by an alkyl radical, or
• a radical of the formula (I'):
• ##STR7## in which R.sub.1 and R.sub.2 are as defined above, R.sub.3 represents a hydrogen atom or an alkyl radical, and
• n is an integer from 2 to 4,
• wherein the alkyl portions or radicals defined above are straight chain or branched and contain from 1 to 4 carbon atoms;
• or a pharmaceutically acceptable salt thereof.