Title: N-phenoxy(or thio)hydrocarbon 3,4,5-trihydroxypiperidine derivatives, their use in medicine and in animal nutrition

What is claimed is:

1. A 3,4,5-trihydroxypiperidine derivative of the formula ##STR25## in which X denotes a straight-chain or branched saturated or mono-ethylenically unsaturated hydrocarbon radical having 1 to 10 carbon atoms,

Y denotes oxygen or sulphur and R¹, R² and R³ are identical or different and independently of one another denote a hydrogen or halogen atom, an alkyl, monocylic or bi-cyclic carbocyclic aryl or aroxy, alkylthio, nitro, hydroxyl, cyano, amino, alkylamino, dialkylamino, amioalkyl, hydroxy-alkyl, carboxylic or sulphonic acid acylamino, sulfonylamino, carboxylic or sulphonic acid acyloxy, carboxyl, carbalkoxy, alkylcarbonyl or formyl radical or a carboxamide or sulphonamide radical which is unsubstituted or substituted by C₁ -C₇ -alkyl or phenyl, each of said alkyl, alkoxy, alkylthio, alkylamino, aminoalkyl, hydroxyalkyl, carbalkoxy and alkylcarbonyl group having up to 12 carbon atoms; and each of said dialkylamino groups having up to 12 carbon atoms in each alkyl group.

2. A compound according to claim 1 in which X denotes a saturated or mono- ethylenically unsaturate alkyl radical with two to five carbon atoms.

3. A compound according to claim 1 or 2 in which R¹, R² and R³ independently denote a hydrogen atom, a C₁ -C₈ -alkyl or alkoxy group, a halogen atom or a carboxyl, C₁ -C₈ -carbalkoxy, amino, carboxylic or sulphonic acid acylamino, carboxamide, mono-or bi-cyclic carboxylic aryl or amino-C₁ -C₈ -alkyl group.

4. A compund according to claim 1 or 2 in which R¹, R² and R³ independently denote a hydrogen atom, a carboxyl, C₁ -C₈ -alkoxy, amino, carboxamide, carboxylic or sulphonic acid acylamino, mono- or bi-cyclic carboxylic aryl or an amino-C₁ -C₈ -alkyl group.

5. A compound according to claim 1 or 2 in which R¹, R² and R³ independently denote a hydrogen atom, a C₁ -C₈ alkyl or alkoxy group or a halogen atom.

6. A compound according to claim 1 which is N-(5-phenoxypentyl)-1-desoxynojirimycin.

7. A compound according to claim 1 which is N-[4-(4-carbethoxyphenoxy)-buten-2-y1]-1-desoxynojirimycin.

8. A compound according to claim 1 which is N-[4tert.-butylphenylthio)-buten-2-y1]-1-desoxynojirimycin.

9. A compound according to claim 1 which is N-[β-(4-Ethoxycarbonyl-phenoxy)-ethyl]-1-desoxynojirimycin.

10. A compound according to claim 1 which is N-[β-(4-Hydroxycarbonylphenoxy)-ethyl]-1-desoxynojirimycin.

11. A compound according to claim 1 which is N-[4-(4-Phenylphenoxy)-buten-2y1]-1-desoxynojirimycin.

12. A medicament of claim 1 in the form of tablets, pills, dragees, capsules or ampoules.

13. A pharmaceutical composition containing as an active ingredient an amount effective for combating diabetes, hyperlipaemia, adiposity, arteriosclerosis or caries of a compound according to claim 1 in admixture with an inert pharmaceutical carrier.

14. A composition according to claim 13 containing from 0.1 to 99.5% by weight of the said active ingredient.

15. A medicament in dosage unit form containing as an active ingredient an amount effective for combating diabetes, hyperlipaemia, adiposity, arteriosclerosis or caries of a compound according to claim 1 in admixture with an inert pharmaceutical carrier.

16. A method for combating diabetes in warm-blooded animals which comprises administering to said animals an effective anti-diabetic amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

17. A method for combating hyperlipaemia in warm-blooded animals which comprises administering to said animals an effective anti-hyperlipaemia amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

18. A method for combating adiposity in warm-blooded animals which comprises administering to said animals an effective anti-adiposity amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

19. A method for combating arteriosclerosis in warm-blooded animals which comprises administering to said animals an effective anti-arteriosclerosis amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

20. A method for combating caries in warm-blooded animals which comprises administering to said animals an effective anti-caries amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

21. A method according to claim 16 in which the active compound is administered in an amount of 1 to 1×10⁴ saccharase inhibitor units per kg body weight per day.

22. A method according to claims 16 or 21 in which the active compound is administered orally.

23. A method according to claim 17 in which the active compound is administered in an amount of 1 to 1×10⁴ saccharase inhibitor units per kg body weight per day.

24. A method according to claims 17 or 23 in which the active compound is administered orally.

25. A method according to claim 18 in which the active compound is administered in an amount of 1 to 1×10⁴ saccharase inhibitor units per kg body weight per day.

26. A method according to claims 18 or 25 in which the active compound is administered orally.

27. A method according to claim 19 in which the active compound is administered in an amount of 1 to 1×10⁴ saccharase inhibitor units per kg body weight per day.

28. A method according to claims 19 or 27 in which the active compound is administered orally.

29. A method according to claim 20 in which the active compound is administered in an amount of 1 to 1×10⁴ saccharase inhibitor units per kg body weight per day.

30. A method according to claims 20 and 29 in which the active material is administered orally.

31. A medicated feed comprising an active compound in an amount effective for reducing fat deposition according to claim 1 in admixture with nutritious material.


Other info:


Inventors: Junge, Bodo (Wuppertal, DE)
Stoltefuss, Jurgen (Haan, DE)
Muller, Lutz (Wuppertal, DE)
Krause, Hans-peter (Wuppertal, DE)
Sitt, Rudiger (Wuppertal, DE)

Application Number: 06/231695
Filing Date: 1981-02-05
Publication_date: 1983-10-04
Assignee: BAYER AG (DE)

Primary Class(es): 514/319 514/328, 546/220, 546/219, 546/208
Other Classes: A23K1/16; C07D211/46; C07D211/00; A61K31/445; C07D211/40
US Patent Ref:

4182767	January, 1980	Murai et al.	424/267	Antihyperglycemic N-alkyl-3,4,5-trihydroxy-2-piperidine methanol
4260622	April, 1981	Junge et al.	546/219	Animal feedstuffs employing 3,4,5-trihydroxypiperidines
4278683	July, 1981	Stoltefuss	546/219	Saccharase inhibiting 3,4,5-trihydroxypiperidine derivatives

Other Refs:
Primary Examiner: Fan, Jane T.
Assistant Examiner:
Attorney: Sprung, Horn, Kramer & Woods