US4639436A — Antidiabetic 3,4,5-trihydroxypiperidines

Claim 1

Independent Claim 901 words

A compound of the formula ##STR264## in which R 1 is C 5 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl, phenyl (a), C 1 -C 2 and C 7 -C 30 alkyl substituted by phenyl (b) or substituted C 1 -C 4 -alkyl said C 5 -C 30 alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH-bridge or naphthyl said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 carbalkoxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said substituted C 1 -C 4 alkyl being substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 - C 4 alkylcarbonyl, carboxyl nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH--bridge or naphthyl, said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said naphthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl R 2 is ##STR265## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine or nitro, R 3 is --H, --CH 3 , --CH 2 OH, --CH 2 --NH 2 , NHR'--CH 2 --, NR'R"--CH 2 --, R'CONH--CH 2 , R'CO--NR"CH 2 --, R'O--CH 2 , R'COOCH 2 --, R'SO 2 NHCH 2 --, R'SO 2 --NR"CH 2 --, R'NH--CO--NH--CH 2 --, R'NHCS--NH--CH 2 , R'O--CO--NH--CH 2 --, wherein R' and R" are the same or different and each has the meaning hydrogen or C 1 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl or phenyl (a), said alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl, nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH--bridge, naphthyl or phenyl (b) said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 -carbaloxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C.sub. 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said napthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl.

Claim 2

Dependent Claim 901 words

A compound of the formula ##STR264## in which R 1 is C 5 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl, phenyl (a), C 1 -C 2 and C 7 -C 30 alkyl substituted by phenyl (b) or substituted C 1 -C 4 -alkyl said C 5 -C 30 alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH-bridge or naphthyl said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 carbalkoxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said substituted C 1 -C 4 alkyl being substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 - C 4 alkylcarbonyl, carboxyl nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH--bridge or naphthyl, said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said naphthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl R 2 is ##STR265## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine or nitro, R 3 is --H, --CH 3 , --CH 2 OH, --CH 2 --NH 2 , NHR'--CH 2 --, NR'R"--CH 2 --, R'CONH--CH 2 , R'CO--NR"CH 2 --, R'O--CH 2 , R'COOCH 2 --, R'SO 2 NHCH 2 --, R'SO 2 --NR"CH 2 --, R'NH--CO--NH--CH 2 --, R'NHCS--NH--CH 2 , R'O--CO--NH--CH 2 --, wherein R' and R" are the same or different and each has the meaning hydrogen or C 1 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl or phenyl (a), said alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono- C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl, nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH--bridge, naphthyl or phenyl (b) said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 -carbaloxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C.sub. 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said napthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl.

Claim 3

Dependent Claim 25 words

A compound of the formula ##STR266## wherein R 2 is ##STR267## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine, or nitro.

Claim 4

Dependent Claim 25 words

A compound of the formula ##STR266## wherein R 2 is ##STR267## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine, or nitro.

Claim 5

Dependent Claim 445 words

A compound of the formula ##STR268## wherein R 2 is ##STR269## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine or nitro and R 3 is CH 2 --NH 2 , --CH 2 --NHR', --CH 2 --NR'R"--, --CH 2 --NHCOR', --CH 2 --NR"--COR', --CH 2 OR', --CH 2 --OCOR', --CH 2 --NHSO 2 R', --CH 2 --NR"--SO 2 R', --CH 2 --NHCONH 2 , --CH 2 --NHCONHR', --CH 2 --NHCSNH 2 , --CH 2 --NHCSNHR', --CH 2 --NH--COOR' wherein R' and R" are the same or different and each is C 1 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl or phenyl (a), said alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono-C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl, nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH-bridge, naphthyl or phenyl (b) said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 -carbalkoxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said naphthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl.

Claim 6

Dependent Claim 445 words

A compound of the formula ##STR268## wherein R 2 is ##STR269## wherein phenyl is unsubstituted or substituted by methyl, ethyl, methoxy, chlorine, bromine or nitro and R 3 is CH 2 --NH 2 , --CH 2 --NHR', --CH 2 --NR'R"--, --CH 2 --NHCOR', --CH 2 --NR"--COR', --CH 2 OR', --CH 2 --OCOR', --CH 2 --NHSO 2 R', --CH 2 --NR"--SO 2 R', --CH 2 --NHCONH 2 , --CH 2 --NHCONHR', --CH 2 --NHCSNH 2 , --CH 2 --NHCSNHR', --CH 2 --NH--COOR' wherein R' and R" are the same or different and each is C 1 -C 30 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -cycloalkinyl or phenyl (a), said alkyl, cycloalkyl, cycloalkenyl and cycloalkinyl being unsubstituted or substituted by hydroxy, C 1 -C 4 -alkoxy, acyloxy, amino, mono-C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, acylamino, mercapto, C 1 -C 4 alkylthio, halogen, C 1 -C 4 alkylcarbonyl, carboxyl, nitro, cyano, formyl, sulfo, a heterocyclic radical derived from a hexose or pentose, attached to the alkyl moiety directly via a ring atom or via an --O--, --S-- or --NH-bridge, naphthyl or phenyl (b) said acyl being derived from an aliphatic carboxylic acid having from 1 to 7 C-atoms, a phenyl carboxylic acid, unsubstituted or substituted by carboxy, hydroxy, halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, nitro or amino, or a 5- or 6-membered aromatic heterocyclic carboxylic acid containing from 1 to 3 hetero-atoms each of which is N, O or S, unsubstituted or substituted by C 1 to C 4 alkyl, chlorine, bromine or amino; said phenyl (a) being unsubstituted or substituted by C 1 to C 10 alkyl, C 1 to C 10 chloroalkyl, C 1 to C 10 nitroalkyl, C 1 to C 10 cyanoalkyl, C 1 to C 10 alkenyl, hydroxyl, C 1 to C 4 alkoxy, amino, mono-C 1 to C 4 alkylamino, di-C 1 -C 4 alkylamino, mercapto, C 1 -C 4 alkylthio, carboxyl, C 1 -C 4 -carbalkoxy, sulfo, C 1 -C 4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, di-C 1 -C 4 alkylaminosulfonyl, nitro, cyano, formyl, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkylcarbonyl, benzoyl, benzylcarbonyl or phenylethylcarbonyl; said naphthyl and phenyl (b) being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, nitro, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl, halogen, C 1 -C 4 alkylthio, mercapto, C 1 -C 4 alkylsulfonyl, sulfo, aminosulfonyl or C 1 -C 4 alkylaminosulfonyl.

Claim 7

Dependent Claim 61 words

A compound of the formula ##STR270## wherein R 1 is C 1 -C 2 and C 7 -C 30 alkyl substituted by phenyl, said phenyl being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl or halogen.

Claim 8

Dependent Claim 61 words

A compound of the formula ##STR270## wherein R 1 is C 1 -C 2 and C 7 -C 30 alkyl substituted by phenyl, said phenyl being unsubstituted or substituted by hydroxyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 6 alkyl or halogen.

Claim 9

Dependent Claim 17 words

A compound according to claim 1, in which R 2 is --H, --SO 3 H or --CN.

Claim 10

Dependent Claim 12 words

A compound according to claim 5 in which R 2 is --H.

Claim 11

Dependent Claim 34 words

A compound according to claim 1, in which R 3 is --H, --CH 2 OH, --CH 3 , --CH 2 NH 2 , --CH 2 --NH or CH 2 --O--(C 1 -C 6 -alkyl).

Claim 12

Dependent Claim 14 words

A compound according to claim 1 in which R 3 is --CH 2 OH.

Claim 13

Dependent Claim 19 words

A compound according to claim 1 in which R 2 is hydrogen and R 3 is --CH 2 OH.

Claim 14

Dependent Claim 19 words

A compound of claim 1 wherein R 1 is C 1 -C 4 alkyl substituted by hydroxy or mercapto.

Claim 15

Dependent Claim 31 words

A compound according to claim 1 which is N-methyl-1-norjirimycin, n-ethyl-1-nojirimycin, N-n-butyl-1-nojirimycin, N-benzyl-1-nojirimycin, N-allyl-1-nojirimycin, N-(β-methoxy-ethyl)-1-nojirimycin, N-n-pentyl-1-desoxynojirimycin, N-n-hexyl-1-desoxynojirimycin, N-benzyl-1-desoxynojirimycin, N-allyl-1-desoxy-nojirimycin, N-(β-methoxy-ethyl)-1-desoxynojirimycin, N-methyl-1-desoxynojirimycin-1-sulphonic acid, N-octyl-1-desoxynojirimycin, N-nonyl-1-desoxy-nojirimycin, 1-tosylaminomethyl-1-desoxy nojirimycin, N-methyl-1-tosylaminomethyl-1-desoxynojirimycin, N-nonyl-1-acetylaminomethyl-1-desoxynojirimycin, N-methyl-benzoylaminomethyl-1-desoxynojirimycin, N-propargyl-1-desoxynojirimycin or N-(2-methylmercaptoethyl)-1-desoxy-nojirimycin.

Claim 16

Dependent Claim 8 words

A compound of claim 1 which is N-(n-Heptyl)-1-desoxynojirimycin.

Claim 17

Dependent Claim 8 words

A compound of claim 1 which is N-Benzyl-1-desoxynojirimycin.

Claim 18

Dependent Claim 8 words

A compound of claim 1 which is N-(β-Hydroxyethyl)-1-desoxynojirimycin.

Claim 19

Dependent Claim 8 words

A compound of claim 1 which is N-(5'hydroxy-n-pentyl)-1-desoxynojirimycin.

Claim 20

Dependent Claim 8 words

A compound of claim 1 which is N-(β-Hydroxypropyl)-1-(desoxynojirimycin).

Claim 21

Dependent Claim 12 words

A compound according to claim 1 which has the steric formula ##STR271##

Claim 22

Dependent Claim 69 words

A pharmaceutical composition for the treatment of diabetes, hyperlipaemia or adiposity containing as an active ingredient an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of a compound according to claim 1 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.

Claim 23

Dependent Claim 37 words

A pharmaceutical composition for the treatment of diabetes, hyperlipaemia or adiposity containing as an active ingredient an effective amount of a compound according to claim 1 in the form of a sterile or physiologically isotonic aqueous solution.

Claim 24

Dependent Claim 20 words

A composition according to claim 18 or 19 containing from 0.5 to 95% by weight of the said active ingredient.

Claim 25

Dependent Claim 38 words

A medicament in dosage unit form for the treatment of diabetes, hyperlipaemia or adiposity comprising an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of a compound according to claim 1 and an inert pharmaceutical carrier.

Claim 26

Dependent Claim 16 words

A medicament of claim 21 in the form of tablets, pills, dragees, capsules, ampoules, or suppositories.

Claim 27

Dependent Claim 69 words

A pharmaceutical composition for the treatment of diabetes, hyperlipaemia or adiposity containing as an active ingredient an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of a compound according to claim 17 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.

Claim 28

Dependent Claim 45 words

A pharmaceutical composition for the treatment of diabetes, hyperlipaemia or adiposity containing as an active ingredient an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of a compound according to claim 17 in the form of a sterile or physiologically isotonic aqueous solution.

Claim 29

Dependent Claim 30 words

A medicament in dosage unit form comprising an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of a compound according to claim 17 and an inert pharmaceutical carrier.

Claim 30

Dependent Claim 16 words

A medicament of claim 25 in the form of tablets, pills, dragees, capsules, ampoules, or suppositories.

Claim 31

Dependent Claim 52 words

A method of combating adiposity, diabetes and/or hyperlipaemia in warm-blooded animals which comprises administering to the said animal an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

Claim 32

Dependent Claim 28 words

A method according to claim 27 in which the active compound is administered in an amount of 0.01 mg to 100 mg per kg body weight per day.

Claim 33

Dependent Claim 13 words

A method according to claim 28 in which the animal is a ruminant.

Claim 34

Dependent Claim 14 words

A method according to claim 27 in which the active compound is administered orally.

Claim 35

Dependent Claim 51 words

A method of combating adiposity, diabetes and/or hyperlipaemia in warm-blooded animals which comprises administering to the animals an effective amount for the treatment of diabetes, hyperlipaemia or adiposity of an active compound according to claim 17 either alone or in admixture with a diluent or in the form of a medicament.

Claim 36

Dependent Claim 15 words

A compound of the formula: ##STR272## wherein R 1 is C 2 -C 18 alkenyl.

Claim 37

Dependent Claim 15 words

A compound of the formula: ##STR272## wherein R 1 is C 2 -C 18 alkenyl.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1990-01-26	1990-07-28	1991-01-27	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1994-01-26	1994-07-28	1995-01-27	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1998-01-26	1998-07-28	1999-01-27	$7700.00	Window Closed / Lapsed

Antidiabetic 3,4,5-trihydroxypiperidines

Abstract

Inventors

Bibliographic Details

Claims Analysis

References Cited (Backward Citations)

USPTO Annuity & Maintenance Windows

Assigned Categories & Tags

Assign Category Tag