US4278683A
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Saccharase inhibiting 3,4,5-trihydroxypiperidine derivatives
Assignee: Bayer AG
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Filing: 1979-08-30
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Granted: 1981-07-14
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Expires: 1999-08-30
Abstract
Abstract The invention relates to 3,4,5-trihydroxypiperidines, processes for their producion, compositions containing them and methods for the use of said 3,4,5-trihydroxypiperidines and compositions containing them. The compounds and compositions of the invention are useful, inter alia, for their saccharase inhibiting activity in warm-blooded animals as well as their ability to improve feed utilization in warm-blooded and cold-blooded animals.
Inventors
- 👤 Jurgen Stoltefuss
- 👤 Lutz Muller
- 👤 Walter Puls
- 👤 Rudiger Sitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:28
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/92; C07D211/98; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/132; A23K50/00; A23K50/30; A61; A61P; A61P1/00; A61P3/00; A61P3/06; A61P3/08; A61P3/10; A61P31/00; A61P31/04; A61P43/00; A61P9/00; A61P9/10; A61P9/12; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/60; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/576; C07F9/59
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
340 words
A 3,4,5-trihydroxypiperidine derivative of the formula ##STR99## or a pharmaceutically acceptable salt thereof, in which R 1 denotes a hydrogen atom, an amino group, an alkyl radical with 1 to 30 carbon atoms, an alkenyl or alkinyl radical with 2 to 18 carbon atoms, said alkyl, alkenyl or alkinyl radicals substituted by hydroxy, C 1 -C 4 -alkoxy, C 1 -C 7 -alkanoyloxy, phenylcarbonyloxy, trifluoromethyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, mercapto, C 1 -C 4 -alkylmercapto, halogen, C 1 -C 4 -alkylcarbonyl, carboxyl, nitro or cyano, phenyl or naphthyl; cycloalkyl, cycloalkenyl or cycloalkadienyl having 3 to 10 carbon atoms; or mono- or bi-cyclic carbocyclic aryl having 6 or 10 carbon atoms and R 2 denotes a --CH 2 NR 3 R 4 , --CH 2 --NR 3 --CO--R 4 , --CH 2 --NR 3 --CONR 4 R 5 , --CH 2 --NR 3 --SO 2 R 4 , --CH 2 --NR 3 --SO 2 --NR 4 R 5 , --CH 2 --NR 3 --CS--R 4 , --CH 2 --NR 3 --CS--NR 4 R 5 , --COOH, --CONH 2 , --COOR 3 , --CO--NR 3 R 4 , --CH 2 --OR 3 , --CH 2 --NH--COOR 4 or --CH 2 --NH--COSR 4 group in which R 3 denotes hydrogen or, independently of R 4 , one of the meanings given for R 4 , and R 4 and R 5 independently denote hydrogen; C 1 -C 30 -alkyl; C 2 -C 18 -alkenyl; C 3 -C 10 -cycloalkyl; C 3 -C 10 -cycloalkenyl; C 3 --C 10 -cycloalkadienyl; C 1 -C 30 -alkyl or C 2 -C 18 -alkenyl substituted by hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -carbalkoxy, carboxy or cyano; a mono- or bi-cyclic carbocyclic aryl radical with 6 or 10 carbon atoms; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, nitro, trifluoromethyl or --CH═CH 2 COOC 2 H 5 ; or benzyl which is unsubstituted or substituted by methyl, methoxy, chlorine or nitro.
Claim 2
Dependent Claim
340 words
A 3,4,5-trihydroxypiperidine derivative of the formula ##STR99## or a pharmaceutically acceptable salt thereof, in which R 1 denotes a hydrogen atom, an amino group, an alkyl radical with 1 to 30 carbon atoms, an alkenyl or alkinyl radical with 2 to 18 carbon atoms, said alkyl, alkenyl or alkinyl radicals substituted by hydroxy, C 1 -C 4 -alkoxy, C 1 -C 7 -alkanoyloxy, phenylcarbonyloxy, trifluoromethyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, mercapto, C 1 -C 4 -alkylmercapto, halogen, C 1 -C 4 -alkylcarbonyl, carboxyl, nitro or cyano, phenyl or naphthyl; cycloalkyl, cycloalkenyl or cycloalkadienyl having 3 to 10 carbon atoms; or mono- or bi-cyclic carbocyclic aryl having 6 or 10 carbon atoms and R 2 denotes a --CH 2 NR 3 R 4 , --CH 2 --NR 3 --CO--R 4 , --CH 2 --NR 3 --CONR 4 R 5 , --CH 2 --NR 3 --SO 2 R 4 , --CH 2 --NR 3 --SO 2 --NR 4 R 5 , --CH 2 --NR 3 --CS--R 4 , --CH 2 --NR 3 --CS--NR 4 R 5 , --COOH, --CONH 2 , --COOR 3 , --CO--NR 3 R 4 , --CH 2 --OR 3 , --CH 2 --NH--COOR 4 or --CH 2 --NH--COSR 4 group in which R 3 denotes hydrogen or, independently of R 4 , one of the meanings given for R 4 , and R 4 and R 5 independently denote hydrogen; C 1 -C 30 -alkyl; C 2 -C 18 -alkenyl; C 3 -C 10 -cycloalkyl; C 3 -C 10 -cycloalkenyl; C 3 --C 10 -cycloalkadienyl; C 1 -C 30 -alkyl or C 2 -C 18 -alkenyl substituted by hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -carbalkoxy, carboxy or cyano; a mono- or bi-cyclic carbocyclic aryl radical with 6 or 10 carbon atoms; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, nitro, trifluoromethyl or --CH═CH 2 COOC 2 H 5 ; or benzyl which is unsubstituted or substituted by methyl, methoxy, chlorine or nitro.
Claim 3
Dependent Claim
72 words
A compound according to claim 1, in which R 1 , R 3 , R 4 and R 5 independently of one another denote a hydrogen atom, an alkyl radical with 1 to 30 carbon atoms, an alkenyl radical or alkinyl radical with 2 to 18 carbon atoms, cycloalkyl, cycloalkenyl or cycloalkadienyl with 3 to 10 carbon atoms, or a mono- or bi-cyclic carbocyclic aryl radical with 6 or 10 carbon atoms.
Claim 4
Dependent Claim
72 words
A compound according to claim 2, in which R 1 , R 3 , R 4 and R 5 independently of one another denote a hydrogen atom an alkyl radical with 1 to 18 carbon atoms, an alkenyl radical or alkinyl radical with 3 to 10 carbon atoms, cycloalkyl, cycloalkenyl or cycloalkadienyl with 3 to 10 carbon atoms, or a mono- or bi-cyclic carbocyclic aryl radical with 6 to 10 carbon atoms:
Claim 5
Dependent Claim
163 words
A compound according to claim 1, of the formula ##STR100## or a pharmaceutically acceptable salt thereof, in which R 6 denotes a hydrogen atom or a C 1 to C 12 alkyl or phenyl-C 1 to C 4 alkyl group. R 7 denotes --CH 2 --NHR 8 , --CH 2 --NHCOR 9 , --CH 2 --NH--SO 2 NR 8 R 9 , --CH 2 --NH--CONHR 8 , --CH 2 --NH--SO 2 R 9 , --CH 2 --NH--CSNHR 8 , --CONH 2 , --CO--NR 8 R 9 , --COOR 8 or --CH 2 OH, R 8 denotes a hydrogen atom or, independently of R 9 , has any of those meanings given for R 9 , and R 9 denotes a C 1 to C 20 alkyl, allyl or C 5 or C 6 cycloalkyl radical, a phenyl radical which is optionally substituted by methyl, methoxy, chlorine or nitro, a benzyl radical which is optionally substituted by methyl, methoxy, chlorine or a nitro radical.
Claim 6
Dependent Claim
53 words
A compound according to claim 4, in which R 7 has the same meaning as in claim 4 except that, in the case of radicals --CH 2 --NH--CONHR 8 and --CH 2 --NH--CSNHR 8 , R 8 only denotes independently of R 9 , any of those radicals given for R 9 .
Claim 7
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR101##
Claim 8
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR102##
Claim 9
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR103##
Claim 10
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR104##
Claim 11
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR105##
Claim 12
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR106##
Claim 13
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR107##
Claim 14
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR108##
Claim 15
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR109##
Claim 16
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR110##
Claim 17
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR111##
Claim 18
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR112##
Claim 19
Dependent Claim
37 words
A pharmaceutical composition containing as an active ingredient an amount effective for combatting diabetes, hyperlipaemia, adiposity or arteriosclerosis of a compound according to claim 1 in admixture with a pharmaceutically acceptable solid, liquid or liquefied gaseous diluent.
Claim 20
Dependent Claim
17 words
A pharmaceutical composition of claim 18 in the form of a sterile or physiologically isotonic aqueous solution.
Claim 21
Dependent Claim
18 words
A composition according to claim 18 containing from 0.1 to 99.5% by weight of the said active ingredient.
Claim 22
Dependent Claim
30 words
A medicament in dosage unit form comprising an amount effective for combating diabetes, hyperlipaemia, adiposity or arteriosclerosis of a compound according to claim 1 together with an inert pharmaceutical carrier.
Claim 23
Dependent Claim
16 words
A medicament of claim 21 in the form of tablets, pills, dragees, capsules, ampoules or suppositories.
Claim 24
Dependent Claim
46 words
A method of combating arteriosclerosis, adiosity, diabetes and/or hyperlipaemia in warm-blooded animals which comprises administering to the animals an effective amount of an active compound according to claim 1 either alone or in admixture with a pharmaceutically acceptable diluent or in the form of a medicament.
Claim 25
Dependent Claim
27 words
A method according to claim 23 in which the active compound is administered in an amount of 0.1 to 100 mg per kg body weight per day.
Claim 26
Dependent Claim
14 words
A method according to claim 24 in which the active compound is administered orally.
Claim 27
Dependent Claim
34 words
A medicated fodder comprising an amount effective for influencing the lean meat/fat ratio in favor of the proportion of lean meat of an active compound as claimed in claim 1 and a nutritious material.
Claim 28
Dependent Claim
17 words
A medicated fodder according to claim 26 containing 0.02 to 20% by weight of the active compound.
References Cited (Backward Citations)
US4182767A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-13 | 1985-01-12 | 1985-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-13 | 1989-01-12 | 1989-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-13 | 1993-01-12 | 1993-07-14 | $7700.00 | Window Closed / Lapsed |