Patent ID: 6313247
Filing Date: 2001-11-06
Classification: C07D,Y10T

Abstract:
Compounds of the general formula (I): ##STR118##with the 9,11-substituted-10,11-dihydro-cinchonan skeleton (9,11-Subst.-DHC skeleton) and the stereoisomers resulting from the different configurations at positions 8 and 9 of the DHC skeleton, whereinY is thio group ( thioether; S), the sulfinyl group (sulfoxide; SO) introducing a new chiral center or a sulfonyl group (sulfone; SO.sub.2);R.sub.1 is an optionally substituted aliphatic, linear or branched, non-chiral or chiral C.sub.1 -C.sub.18 residue selected from the group consisting of n-propyl, n-decyl, n-dodecyl, n-octadecyl, isopropyl, tert.-butyl, .beta.-chloro-tert.-butyl, .beta.,.beta.'-dichloro-tert.-butyl, 2-hydroxy-1,2-diphenylethyl, 2-amino-1,2-diphenylethyl, (1S)- or (1R)-1-carboxy-3-methylbutyl or the methyl esters thereof, 3-trialkoxysilylpropyl, 3-trichlorosilylpropyl, 10-trialkoxysilyldecyl, 10-trichlorosilyldecyl, 3-(3-trialkoxysilylpropyl)thiopropyl, 3-(3-tri-alkoxysilylpropyl)sulfinylpropyl, 3-(3-trichlorosilylpropyl)thiopropyl, propylthiopropyl and 3-(3-trichlorosilylpropyl)sulfinylpropyl;allyl;phenylamino or 3,5-dinitrobenzoylaminoan optionally substituted non-chiral or chiral alicyclic or heteroalicyclic residue selected from the group consisting of 1-adamantyl, 1-hydroxy-2-indanyl, cyclohexyl, 2-aminocyclohexyl, cyclohexenyl, 3-quinuclidinyl, cis or trans 2- or 4-carboxycyclohexyl or the methyl ester thereof, cis or trans 2- or 4-carboxycyclohexenyl or the methyl esters thereof and 3-cholesteryl;an optionally substituted aromatic or heteroaromatic residue selected from the group consisting of 3,5-dinitrophenyl, 3,4-dichlorophenyl, 3,5-bis-(trifluoromethyl)phenyl, 4-methylphenyl, 3,5-dimethylphenyl, 3,4,5-trimethoxyphenyl, 2,6-diisopropylphenyl, 1- or 2-naphthyl, 6-methoxy-4-chinolinyl, 2- or 3- or 4-carboxyphenyl and the methyl esters thereof;an optionally substituted non-chiral or chiral arylalkyl residue selected from the group consisting of benzyl, di-phenylmethyl, triphenylmethyl, (R)- or (S)-.alpha.-methyl-benzyl, (R)- and (S)-1-(4-nitrophenyl)ethyl;trialkylsilyl;any one of the groups 3-tri-alkoxysilylpropyl, 3-trichlorosilylpropyl, 10-trialkoxysilyldecyl, 10-trichlorosilyldecyl, 3-(3-trialkoxysilyl-propyl)thiopropyl, 3-(3-trialkoxysilylpropyl)sulfinfylpropyl, 3-(3-trichlorosilylpropyl)thiopropyl, 3-(3-trichlorosilylpropyl)sulfinylpropyl or propylthiopropyl is optionally immobilized onto silica;2-((meth)acryloyloxy)ethyl or (meth)acryloyl so that the 9,11-Subst.-DHC skeleton of formula (I) via R.sub.1 may be polymerized or copolymerized with a comonomer selected from vinyl modified silica, (meth)acryl modified silica, 3-trialkoxysilylpropyl(meth)-acrylate, styrene, any (meth)acrylate, vinyl functionialized polysiloxane and any other olefin;or a spacer selected from the group consisting of 1,4-tetramethylene, 1,6-hexamethylene, trans or cis 1,4- or 1,2-cyclohexylene, 1,2- or 1,3- or 1,4-phenylene, toluene-2,6-diyl, 3,3'-dimethoxy-biphenyl-4,4'-diyl (dianisidinediyl), 1,1'-binaphthyl-2,2'-diyl, 1,2-diphenylethan-1,2-diyl, phthalazin-1,4-diyl, adamantine-1,7-diyl, cyclohexan-1,3,5-triyl, benzene-1,3,5-triyl and adamantane-1,3,5,7-tetrayl connecting two, three or four 9,11-Subst.-DHC skeletons of formula (i) but missing R.sub.1.R.sub.2 is hydrogen, hydroxy or a C.sub.1 -C.sub.15 alkoxy or alicyclicoxy group; is hydrogen;R.sub.3 is hydrogen,an optionally substituted aliphatic linear or branched, chiral or non-chiral aliphatic C.sub.1 -C.sub.18 or alicyclic residue selected from the group consisting of 2-hydroxyethyl, 2-alkoxyethyl, 2-(alkylcarbonyloxy)ethyl, 2-(alkylcarbamoyl-oxy)ethyl, 2-(N-alkyl substituted alkylcarbamoyloxy)ethyl, 2-(N-substituted amino)ethyl, 2-aminoethyl, octyl, dodecyl, octadecyl and cholesteryl;2-((meth)acryloyloxy)ethyl or optionally N-alkyl 2-((meth)-acrylamido) ethyl so that the 9,11-Subst.-DHC skeleton of formula (I) via R.sub.3 may be polymerized or copolymerized with other polymerizable comonomers;3-trialkoxysilylpropyl, 3-trichlorosilylpropyl or propyl which are immobilized onto silica;R.sub.4 is missing thus signifying the free base, hydrogen in the case of ammonium salts, or methyl, allyl, arylmethyl or benzyl, in the case of quaternized salts.