Patent US4328233A successfully refreshed from Google Patents.
US4328233A
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α-Glucosidase inhibiting 2-hydroxymethyl-3,4,5-trihydroxy-piperidines
Assignee: Bayer AG
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Filing: 1979-10-29
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Granted: 1982-05-04
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Expires: 1999-10-29
Abstract
Abstract The invention relates to 2-hydroxymethyl-3,4,5-trihydroxy-6-substituted-piperidines and methods for their preparation. The invention also includes compositions containing said 2-hydroxymethyl-3,4,5-trihydroxy-6-substituted-piperidines and the use of said compounds and compositions for influencing carbohydrate metabolism and fat metabolism and for use in animal nutrition as feed additives.
Inventors
- 👤 Horst Boshagen
- 👤 Rudiger Sitt
- 👤 Ernst Truscheit
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:56
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/132; A23K50/00; A23K50/30; A61; A61P; A61P3/00; A61P3/06; A61P3/08; A61P3/10; A61P43/00
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
162 words
A compound of the formula ##STR3## in which R denotes C 1 to C 30 alkyl, C 2 to C 18 alkenyl or C 2 to C 18 alkinyl optionally substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 -alkoxy or nitro; C 3 to C 12 cycloalkyl, C 3 to C 12 cycloalkenyl, C 3 to C 12 cycloalkadienyl, C 3 to C 12 bicycloalkyl, C 3 to C 12 bicycloalkenyl, C 3 to C 12 bicycloalkadienyl, C 3 to C 12 tricycloalkyl, C 3 to C 12 tricycloalkenyl or C 3 to C 12 tricycloalkadienyl; or phenyl or naphthyl being unsubstituted or having 1 to 5 substituents selected from halogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylmercapto, C 1 -C 4 -alkylsulphonyl, nitro, cyano, di-C 1 to C 12 alkylamino, di-C 1 to C 12 alkylaminosulphonyl or di-C 1 to C 12 dialkylaminocarbonyl.
Claim 2
Dependent Claim
162 words
A compound of the formula ##STR3## in which R denotes C 1 to C 30 alkyl, C 2 to C 18 alkenyl or C 2 to C 18 alkinyl optionally substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 -alkoxy or nitro; C 3 to C 12 cycloalkyl, C 3 to C 12 cycloalkenyl, C 3 to C 12 cycloalkadienyl, C 3 to C 12 bicycloalkyl, C 3 to C 12 bicycloalkenyl, C 3 to C 12 bicycloalkadienyl, C 3 to C 12 tricycloalkyl, C 3 to C 12 tricycloalkenyl or C 3 to C 12 tricycloalkadienyl; or phenyl or naphthyl being unsubstituted or having 1 to 5 substituents selected from halogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylmercapto, C 1 -C 4 -alkylsulphonyl, nitro, cyano, di-C 1 to C 12 alkylamino, di-C 1 to C 12 alkylaminosulphonyl or di-C 1 to C 12 dialkylaminocarbonyl.
Claim 3
Dependent Claim
71 words
A compound according to claim 1 in which R denotes a C 1 to C 18 alkyl radical optionally substituted by 1 to 5 halogen atoms, a C 3 to C 10 alkenyl, C 3 to C 10 alkinyl, or C 3 to C 7 cycloalkyl radical or a phenyl radical which is optionally substituted by halogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy or nitro.
Claim 4
Dependent Claim
79 words
A compound of claim 1 wherein R represents C 1 -C 18 alkyl, C 2 -C 18 alkenyl or C 2 -C 18 alkinyl which is unsubstituted or substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 -alkoxy or nitro; phenyl or naphthyl which is unsubstituted or substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 alkyl, halogeno C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, nitro or cyano.
Claim 5
Dependent Claim
23 words
The compound of claim 3 wherein R denotes C 1 -C 18 alkyl, C 3 -C 10 alkenyl, C 3 -C 10 alkinyl.
Claim 6
Dependent Claim
21 words
The compound of claim 3 wherein R denotes a member selected from methyl, ethyl, propyl, butyl, pentyl, heptyl, octyl or phenyl.
Claim 7
Dependent Claim
30 words
The compound of claim 1 wherein the said alkyl, alkenyl or alkinyl radical is substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 -alkoxy or nitro.
Claim 8
Dependent Claim
41 words
The compound of claim 1 wherein the said phenyl or naphthyl or is substituted by 1 to 5 radicals selected from halogen, C 1 -C 4 alkyl, halogeno C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, nitro or cyano.
Claim 9
Dependent Claim
9 words
A compound according to claim 1 which is 2-hydroxymethyl-3,4,5-trihydroxy-6-propylpiperidine.
Claim 10
Dependent Claim
9 words
A compound according to claim 1 which is 2-hydroxymethyl-3,4,5-trihydroxy-6n-butyl-piperidine.
Claim 11
Dependent Claim
9 words
A compound according to claim 1 which is 2-hydroxymethyl-3,4,5-trihydroxy-6-n-pentyl-piperidine.
Claim 12
Dependent Claim
9 words
A compound according to claim 1 which is 2-hydroxymethyl-3,4,5-trihydroxy-6-n-octyl-piperidine.
Claim 13
Dependent Claim
9 words
A compound according to claim 1 which is 2-hydroxymethyl-3,4,5-trihydroxy-6-n-heptyl-piperidine.
Claim 14
Dependent Claim
49 words
A pharmaceutical composition containing as an active ingredient an amount effective for α-glucosidase inhibition, of a compound according to claim 1 in admixture with a solid or liquefied gaseous diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.
Claim 15
Dependent Claim
17 words
A pharmaceutical composition of claim 13 in the form of a sterile or physiologically isotonic aqueous solution.
Claim 16
Dependent Claim
20 words
A composition according to claim 13 or 14 containing from 0.1 to 99.5% by weight of the said active ingredient.
Claim 17
Dependent Claim
26 words
A medicament in dosage unit form comprising an amount effective for α-glucosidase inhibition, of a compound according to claim 1 together with an inert pharmaceutical carrier.
Claim 18
Dependent Claim
14 words
A medicament of claim 16 in the form of tablets, pills, dragees, or capsules.
Claim 19
Dependent Claim
46 words
A method of combating adiposity, diabetes and/or hyperlipaemia in warm-blooded animals which comprises administering to said animals an amount effective for α-glucosidase inhibition, of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.
Claim 20
Dependent Claim
14 words
A method according to claim 18 in which the active compound is administered orally.
Claim 21
Dependent Claim
29 words
A medicated fodder comprising a compound as claimed in claim 1 in an amount effective for reducing deposition of fat and saving feed protein together with an animal feedstuff.
Claim 22
Dependent Claim
12 words
A medicated fodder of claim 20 in the form of a premix.
Claim 23
Dependent Claim
57 words
A method of avoiding undesired deposition of fat and for achieving an increased deposition of lean meat, and for better feed utilization in warm-blooded animals which compises administering to said animals an effective amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.
References Cited (Backward Citations)
US4065562A
Cited
US4182767A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-05-03 | 1985-11-02 | 1986-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-05-03 | 1989-11-02 | 1990-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-05-03 | 1993-11-02 | 1994-05-04 | $7700.00 | Window Closed / Lapsed |