Pharmaceutically active ceramide-related compounds
First Claim
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1. A compound having the formula R1 --Y1 --CHZ1 --CH(NY2 Y3)--CH2 --Z2, wherein:
- R1 is a straight-chained alkyl, alkenyl or alkynyl group having from 8 to 19 carbon atoms in the aliphatic chain;
Y1 is --CH═
CH--, --C.tbd.C-- or --CH(OH)CH(OH)--;
Z1 is OH or a phosphorylcholine attachment-inhibiting group selected from the group consisting of --X1, --OX1, --X2 X3 and --OX2 X3 ;
Y2 is H, a phenyl group, an alkyl-substituted phenyl group having from 1 to about 6 carbons in the alkyl chain, or an alkyl chain having from 1 to 6 carbons;
Y3 is H or a group having the formula --C(O)R2 or --S(O)2 R2 ;
R2 is a straight-chained alkyl group selected from the group consisting of (CH2)3 CH3, (CH2)5 CH3, (CH2)7 CH3 and --(CH2)9 CH3, an alkenyl having from 1 to 23 carbon atoms in the chain or an alkynyl group having from 1 to 23 carbon atoms in the chain;
Z2 is a phosphorylcholine attachment-inhibiting group selected from the group consisting of --X1, --OX1, --X2 X3 and --OX2 X3 ;
X1 is selected from the group consisting of C(O)H, CO2 H, CH3 (C(CH3)3)2, Si(C(CH3)3)3, Si(PO4)2 C(CH3)3, a phenyl group, an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain, an alkyl chain having from 1 to 6 carbons, an amino group, a fluorine, a chlorine, and a group having the formula C(R3 R4)OH;
X2 is selected from the group consisting of CH2 --, C(CH3)2 --, Si(PO4)2 --, Si(CH3)2 --, SiCH3 PO4 --, C(O)-- and S(O)2 --;
X3 is selected from the group consisting of --C(O)H, --CO2 H, --CH3, --C(CH3)3, --Si(CH3)3, --SiCH3 (C(CH3)3)2, --Si(PO)4)2 C(CH3)3, a phenyl group, an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain, an alkyl chain having from 1 to 6 carbons, an amino moiety, a chlorine, a fluorine, or a group having the formula C(R3 R4)OH, wherein each of R3 and R4 is independently an alkyl chain having from 1 to 6 carbons, a phenyl group or an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain;
and wherein when Z2 is an amino group, R2 is an aliphatic chain having from 1 to 9 or from 19 to 23 carbon atoms in the aliphatic chain.
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Abstract
This invention provides a compound having the formula R1 --Y1 --CHZ1 --CH(NY2 Y3)--CH2 --Z2, wherein: R1 is a straight-chained alkyl, alkenyl or alkynyl group having from 8 to 19 carbon atoms in the aliphatic chain; Y1 is --CH═CH--, --C.tbd.C-- or --CH(OH)CH(OH)--; Z1 is OH or a conversion-inhibiting group; Z2 is a conversion-inhibiting group; Y2 is H, a phenyl group, an alkyl-substituted phenyl group having from 1 to about 6 carbons in the alkyl chain, or an alkyl chain having from 1 to 6 carbons; Y3 is H or a group having the formula --C(O)R2 or --S(O)2 R2 ; R2 is a straight-chained alkyl, alkenyl or alkynyl group having from 1 to 23 carbon atoms in the chain; and when Z2 is an amino, R2 is an aliphatic chain having from 1 to 9 or from 19 to 23 carbon atoms in the aliphatic chain.
70 Citations
15 Claims
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1. A compound having the formula R1 --Y1 --CHZ1 --CH(NY2 Y3)--CH2 --Z2, wherein:
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R1 is a straight-chained alkyl, alkenyl or alkynyl group having from 8 to 19 carbon atoms in the aliphatic chain; Y1 is --CH═
CH--, --C.tbd.C-- or --CH(OH)CH(OH)--;Z1 is OH or a phosphorylcholine attachment-inhibiting group selected from the group consisting of --X1, --OX1, --X2 X3 and --OX2 X3 ; Y2 is H, a phenyl group, an alkyl-substituted phenyl group having from 1 to about 6 carbons in the alkyl chain, or an alkyl chain having from 1 to 6 carbons; Y3 is H or a group having the formula --C(O)R2 or --S(O)2 R2 ; R2 is a straight-chained alkyl group selected from the group consisting of (CH2)3 CH3, (CH2)5 CH3, (CH2)7 CH3 and --(CH2)9 CH3, an alkenyl having from 1 to 23 carbon atoms in the chain or an alkynyl group having from 1 to 23 carbon atoms in the chain; Z2 is a phosphorylcholine attachment-inhibiting group selected from the group consisting of --X1, --OX1, --X2 X3 and --OX2 X3 ; X1 is selected from the group consisting of C(O)H, CO2 H, CH3 (C(CH3)3)2, Si(C(CH3)3)3, Si(PO4)2 C(CH3)3, a phenyl group, an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain, an alkyl chain having from 1 to 6 carbons, an amino group, a fluorine, a chlorine, and a group having the formula C(R3 R4)OH; X2 is selected from the group consisting of CH2 --, C(CH3)2 --, Si(PO4)2 --, Si(CH3)2 --, SiCH3 PO4 --, C(O)-- and S(O)2 --; X3 is selected from the group consisting of --C(O)H, --CO2 H, --CH3, --C(CH3)3, --Si(CH3)3, --SiCH3 (C(CH3)3)2, --Si(PO)4)2 C(CH3)3, a phenyl group, an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain, an alkyl chain having from 1 to 6 carbons, an amino moiety, a chlorine, a fluorine, or a group having the formula C(R3 R4)OH, wherein each of R3 and R4 is independently an alkyl chain having from 1 to 6 carbons, a phenyl group or an alkyl-substituted phenyl group having from 1 to 6 carbons in the alkyl chain; and wherein when Z2 is an amino group, R2 is an aliphatic chain having from 1 to 9 or from 19 to 23 carbon atoms in the aliphatic chain. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
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Specification
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Current AssigneeTransave Inc. (Insmed Incorporated)
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Original AssigneeThe Liposome Co., Inc. (Perrigo Company PLC)
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InventorsWei, Yong, Ahmad, Imran, Janoff, Andrew S., Mayhew, Eric
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Primary Examiner(s)Kishore, Gollamudi S.
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Application NumberUS08/383,291Time in Patent Office838 DaysField of Search564/197, 564/198, 564/196, 564/97, 564/199, 564/200, 564/84, 564/88, 564/95, 564/169, 556/404, 556/405, 562/455, 562/567US Class Current556/404CPC Class CodesA61K 9/1271 Non-conventional liposomes,...A61P 35/00 Antineoplastic agentsC07F 7/1804 Compounds having Si-O-C lin...Y10T 428/2984 Microcapsule with fluid cor...
