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US 7,119,229 B2Granted
Alkaloid derivative and a pharmaceutical composition containing the same
AssigneesChemtech Research Incorporation, Kt&G Corporation
InventorsWan Joo Kim, Kyoung Soo Kim, Myung Hwa Kim, Jong Yek Park, Jung Min Jang, Jae Won Choi, Dong Hoo Kim
Life of this patent
Estimating the term…
Abstract
Colchicine derivatives represented by the formula (I) with a halogen or nitric ester group, or pharmaceutically acceptable salts thereof, are described. Pharmaceutical compositions containing the same as effective components are also described. The colchicine derivatives were found to have anticancer, anti-proliferous and immunosuppressive function. Methods for preparing the colchicines derivatives are also provided.
Claims6
Colchicine derivative of the following formula (I) and pharmaceutically acceptable salts thereof:
- wherein:
- when R1 is N(R6)-A, N(A)2 or X2-A,
- R2 is X3R7,
- R3 and R4 are independently hydrogen or a methyl group,
- R5 is hydrogen, or a methyl group,
- wherein R6 and R7 are independently hydrogen or a lower alkyl group,
- X, X1, and X3 are independently O or S, and X2 is S;
- when R2 is X2C(X1)-A or X2-A,
- R1 is N(R6)COCH3, N(R6)COCF3, or NHC(O)OR8,
- R3 and R4 are independently hydrogen or a methyl group,
- R5 is hydrogen or a methyl group,
- wherein R6 is hydrogen or a lower alkyl group,
- R8 is a lower alkyl, alkenyl, or substituted or unsubstituted aryl, and
- X, X1 and X2 are independently O or S;
- when R3 and R4 are independently C(X1)-A or -A,
- R1 is N(R6)COCH3, N(R6)COCF3, or NHC(O)OR8,
- R2 is X3R7,
- R5 is hydrogen or a methyl group,
- wherein R6 and R7 are independently hydrogen or a lower alkyl group,
- R8 is a lower alkyl, alkenyl, or substituted or unsubstituted aryl, and
- X, X1and X3 are independently O or S;
- wherein A is represented by the formula (a), (b), (c), (d), (e), (f), (g), (h), (i) or (j):
- wherein Y1 is a C3 to C10 straight chain or branched alkyl or a substituted C5 to C7 cycloalkyl group;
- Hal is halogen;
- R9 is hydrogen or a lower alkyl group;
- n1 is an integer from 1 to 6;
- n2 and n3 are independently an integer from 1 to 5;
- n4 is an integer from 0 to 3;
- and
- n5 is an integer from 1 to 6.
27 more elements
A compound selected from the group consisting of:
- 4-chloro-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-chloromethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-chloromethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-iodo-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)butylamide;
- 4-nitrooxy-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-iodomethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-nitrooxymethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-iodomethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-nitrooxymethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-chloro-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-chloromethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-chloromethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-iodo-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-nitrooxy-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-iodomethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-nitrooxymethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-iodomethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-nitrooxymethyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene7-yl)-benzamide;
- 4-chloro-N-methyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-butylamide;
- 4-nitrooxymethyl-N-methyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 3-nitrooxymethyl-N-methyl-N-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)-benzamide;
- 4-chloro-N-methyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)butylamide;
- 4-chloromethyl-N-methyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)benzamide;
- N-methyl-4-nitrooxy-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)butylamide;
- N-methyl-4-nitrooxymethyl-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptarene-7-yl)benzamide;
- or pharmaceutically acceptable salts thereof.
23 more elements
Dependencies are inferred from the claim text.