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Claims for Patent: 4,680,291

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Claims for Patent: 4,680,291

Title: Propenylamines, processes for their production and pharmaceutical compositions containing them
Abstract:The present invention provides propenylamines useful as anti-mycotic agents.
Inventor(s): Hamberger; Helmut (Vienna, AT), Stephen; Adrian (Vienna, AT), Stutz; Anton (Maria Enzersdorf, AT), Stutz; Peter (Vienna, AT)
Assignee: Sandoz Ltd. (Basel, CH)
Application Number:06/934,772
Patent Claims: 1. A compound of formula I, ##STR79## wherein (a)

(i) R.sub.1 is a radical of formula IIa, ##STR80## wherein R.sub.7 and R.sub.8, independently, are hydrogen, halogen of atomic number from 9 to 53, trifluoromethyl, hydroxy, nitro, lower alkyl or lower alkoxy,

or a radical of formula IIb, IIc, IId, IIe, ##STR81## wherein R.sub.9 is hydrogen, halogen of atomic number from 9 to 53, hydroxy, lower alkyl or lower alkoxy,

X is oxygen, sulphur, imino, lower alkylimino or a radical of formula --(CH.sub.2).sub.r -- wherein r is 1, 2 or 3,

s is 3, 4 or 5, and

t is 2, 3 or 4, and

R.sub.2 is hydrogen or lower alkyl, or

(ii) R.sub.1 and R.sub.2 together with the carbon atom to which they are bound form a radical of formula IIf or IIg, ##STR82## wherein p is 1, 2 or 3,

R.sub.3 and R.sub.5, independently, are hydrogen or lower alkyl,

R.sub.4 is alkyl (C.sub.1-6), alkenyl (C.sub.3-12), alkynyl (C.sub.3-12) or cycloalkyl (C.sub.3-8)alkyl (C.sub.1-6); and

R.sub.6 is (i) an aromatic, five-membered heterocycle containing one oxygen, sulphur or nitrogen hetero-ring atom and optionally an additional one or two nitrogen hetero-ring atoms and being optionally substituted on a carbon ring atom by halogen of atomic number from 9 to 53, hydroxy, lower alkyl or lower alkoxy, and any nitrogen ring atom present being optionally substituted when possible, by lower alkyl, (ii) a radical of formula IIIa, ##STR83## wherein R.sub.9 is as defined above,

(iii) a radical of formula IIIb,

wherein

R.sub.10 is alkyl (C.sub.1-12), alkenyl (C.sub.3-12), alkynyl (C.sub.3-12) cycloalkyl (C.sub.3-8)alkyl (C.sub.1-6), phenyl-alkyl (C.sub.7-12), phenyl, phenylalkoxy (C.sub.7-16), or aminoalkyl (C.sub.1-12);

(iv) a radical of formula IIIc, IIId or IIIe, ##STR84## wherein R.sub.11, R.sub.12 and R.sub.13, independently, are hydrogen or lower alkyl,

m is a whole number from 0 to 4,

n is a whole number from 0 to 3, and

v is a whole number from 0 to 5,

(v) a radical of formula IIIf, ##STR85## wherein R.sub.14 is lower alkyl, alkoxy (C.sub.1-12)carbonyl, alkenyl (C.sub.3-12), alkynyl (C.sub.3-12), phenylalkyl (C.sub.7-12) or phenyl,

R.sub.15 and R.sub.16, independently, are hydrogen or lower alkyl, and

q is a whole number from 0 to 5, or

(vi) a radical of formula IIIg ##STR86## wherein R.sub.17 and R.sub.18, independently, are hydrogen, halogen of atomic number from 9 to 53, trifluoromethyl, hydroxy, nitro, lower alkyl or lower alkoxy, with the general proviso that R.sub.1 is not a radical of formula IIa when R.sub.6 is a radical of formula IIIg or phenyl or phenylalkyl,

(b)

R.sub.1 is a radical of formula IIa to IIe, as defined above,

R.sub.2, R.sub.5 and R.sub.6 are as defined above, and

R.sub.3 and R.sub.4 together are --(CH.sub.2).sub.u -- wherein u is a whole number from 1 to 8.

or a chemotherapeutically acceptable salt thereof.

2. A pharmaceutical composition which comprises a therapeutically effective amount of a compound of claim 1, in association with a chemotherapeutically acceptable diluent or carrier.

3. A compound of claim 1, having the formula Ig, ##STR87## wherein R.sub.1.sup.I is 1-naphthyl, optionally mono-substituted by lower alkyl or alkoxy,

u is a whole number from 1 to 8,

R.sub.6.sup.II is of formula ##STR88## wherein R.sub.19 is hydrogen, hydroxy, lower alkoxy or lower alkyl,

or of formula

wherein

R.sub.20 is alkyl (C.sub.1-12) or phenylalkyl(C.sub.7-12)

or of formula ##STR89## wherein m, n and v are as defined in claim 1.

4. A compound of claim 1, having the formula Ih, ##STR90## wherein R.sub.1.sup.II is a radical of formula IIa, IIb wherein X is oxygen or sulphur, IIc, IId wherein s is 4, IIe wherein t is 3 or a radical of formula ##STR91## wherein R.sub.9 is as defined in claim 1,

R.sub.2 and R are independently hydrogen or lower alkyl,

u is a whole number from 1 to 8,

R.sub.6.sup.III is as defined in claim 1 for R.sub.6, with the following provisos,

(a) R.sub.10 is other than phenyl or phenylalkoxy, and

(b) when R.sub.1.sup.II is 1-naphthyl optionally mono-substituted by lower alkyl or alkoxy and R.sub.2 and R.sub.5 are each hydrogen, R.sub.6.sup.III is other than

(i) a radical of formula IIIa, IIIb or IIIf,

(ii) a radical of formula IIIc, IIId or IIIe, wherein R.sub.11, R.sub.12 and R.sub.13 are each hydrogen, or

(iii) a radical of formula IIIg wherein one of R.sub.17 and R.sub.18 is hydrogen and the other is hydroxy, lower alkyl or lower alkoxy, or

(iv) an optionally substituted thiophen or furan radical.

5. A compound of claim 1 having the formula Ii, ##STR92## wherein R.sub.1.sup.III is a radical of formula IIa, IIb wherein

X is oxygen or sulphur, IIc, IId wherein a is 4, IIe wherein t is 3, or a radical of formula ##STR93## R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.9 are as defined in claim 1, with the proviso that R.sub.3 and R.sub.4 are other than --(CH.sub.2).sub.u --,

R.sub.6.sup.IV is as defined in claim 1 for R.sub.6 with respect to formula I, with the following provisos

(i) R.sub.10 is other than phenyl or phenylalkoxy and

(ii) when R.sub.1 is a radical of formula IIa, R.sub.6.sup.IV is other than a radical of formula IIIg, or phenyl.

6. A compound of claim 1, which is N-(3-cyclohex-1-en-1-yl-2-trans-propenyl)-N-methyl-N-(1-naphthylmethyl)ami ne.

7. A method of combatting mycoses in or on animals which comprises administering an anti-mycotic amount of a compound of claim 1 to an animal in need of such treatment.

8. The compound according to claim 1 which is 4-[N-methyl-N-(1-naphthylmethyl)]aminocrotonic acid ethyl ester.

9. The compound according to claim 1 which is N-(3-cyclohex-1-en-1-yl-2-cis-propenyl)-N-methyl-N-(1-naphthylmethyl)amine

10. The compound according to claim 1 which is N-(3-cyclohexyl-2-trans-propenyl)-N-methyl-N-(1-naphthylmethyl)amine.

11. The compound according to claim 1 which is N-methyl-N-[3-(5'-methyl-2'-thienyl)-2-trans-propenyl)-N-(1-naphthylmethyl )amine.

12. A compound according to claim 1 of the formula Ie:

in which R.sub.1 and R.sub.6 are as defined in claim 1.

13. The compound of claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is 2-thienyl.

14. The compound according to claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is ##STR94##

15. The compound according to claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is 4-pyridyl.

16. The compound according to claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is --CH.dbd.CH.C.sub.6 H.sub.5.

17. The compound according to claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is Cyclohept-1-en-1-yl.

18. The compound according to claim 12 in which R.sub.1 is 1-naphthyl and R.sub.6 is ##STR95##

19. The compound according to claim 12 in which R.sub.1 is 3-benzo[b]thienyl and R.sub.6 is Cyclohex-1-en-1-yl.

20. A compound according to claim 1 of the formula If: ##STR96## in which R.sub.1, R.sub.6 and u are as defined in claim 1.

21. The compound of claim 20 in which R.sub.1 is 1-naphthyl, R.sub.6 is C.sub.6 H.sub.5 and u is 4.

22. The compound of claim 20 in which R.sub.1 is 1-naphthyl, R.sub.6 is C.sub.6 H.sub.5 and u is 3.

23. The compound of claim 20 in which R.sub.1 is 1-naphthyl, R.sub.6 is C.sub.6 H.sub.5 and u is 5.

24. The compound of claim 20 in which R.sub.1 is 5-tetralinyl R.sub.6 is C.sub.6 H.sub.5 and u is 4.

25. The compound of claim 1 which is N-(3-cyclohex-1-en-1-yl-2-cis-propenyl)-2-(1'-naphthyl)-piperidine.

26. The compound of claim 1 which is N-(1-acenaphthenyl)-N-methyl-N-(3-phenyl-2-trans-propenyl)amine.

27. The compound of claim 1 which is N-(1-acenaphthenyl)N-methyl-N-[3-(5'-methyl-2'-thienyl)-2-trans-propenyl]a mine.

28. The compound of claim 1 which is N-(6,7,8,8a-tetrahydro-1-acenaphthenyl)-N-methyl-N-(3-phenyl-2-transpropen yl)amine.

29. The compound of claim 1 which is N-methyl-N-(2,3-dihydro-1-phenalenyl)-N-(3-phenyl-2-trans-propenyl)amine.

30. A compound according to claim 1 in which R.sub.6 is an aromatic, five membered heterocycle as defined in claim 1.

31. A compound according to claim 1 in which R.sub.6 is a radical of formula IIIa.

32. A compound according to claim 1 in which R.sub.6 is a radical of formula IIIb.

33. A compound according to claim 1 in which R.sub.6 is a radical of the formula IIIc, IIId or IIIe.

34. A compound according to claim 1 in which R.sub.6 is a radical of the formula IIIf.

35. A compound according to claim 3 in which R.sub.14 is alkoxycarbonyl, alkenyl, alkynyl or phenylalkyl.

36. A compound according to claim 1 in which R.sub.3 and R.sub.4 together are --CH.sub.2).sub.u wherein u is a whole number from 1 to 8; R.sub.1 is a radical of Formula IIa to IIe and R.sub.2, R.sub.5 and R.sub.6 are as defined in claim 1.

37. A compound according to claim 1 of the formula: ##STR97## wherein R.sub.1 is a radical of formula IIa, ##STR98## wherein R.sub.7 and R.sub.8, independently, are hydrogen, halogen of atomic number from 9 to 53, trifluoromethyl, hydroxy, nitro, lower alkyl or lower alkoxy, or a radical of formula IIb, IIc, IId, IIe, ##STR99## wherein R.sub.9 is hydrogen, halogen of atomic number from 9 to 53, hydroxy, lower alkyl or lower alkoxy,

X is oxygen, sulphur, imino, lower alkylimino or a radical of formula --(CH.sub.2).sub.r --

wherein r is 1, 2 or 3,

s is 3, 4 or 5, and

t is 2, 3 or 4, and

R.sub.2 is hydrogen or lower alkyl, or

R.sub.3 and R.sub.5, independently, are hydrogen or lower alkyl,

R.sub.4 is alkyl (C.sub.1-6), alkenyl (C.sub.3-12), alkynyl (C.sub.3-12) or cycloalkyl (C.sub.3-8) alkyl(C.sub.1-6); and

R.sub.6 is

(i) an aromatic, five-membered heterocycle containing one oxygen, sulphur or nitrogen hetero-ring atom and optionally an additional one or two nitrogen hetero-ring atoms and being optionally substituted on a carbon ring atom by halogen of atomic number from 9 to 53, hydroxy, lower alkyl or lower alkoxy, and any nitrogen ring atom present being optionally substituted when possible, by lower alkyl,

(ii) a radical of formula IIIa, ##STR100## wherein R.sub.9 is as defined above,

(iii) a radical of formula IIIb,

wherein

R.sub.10 is alkyl (C.sub.1-12), alkenyl(C.sub.3-12), alkynyl (C.sub.3-12) cycloalkyl (C.sub.3-8)alkyl (C.sub.1-6), phenyl-alkyl (C.sub.7-12), phenyl, phenylalkoxy (C.sub.7-16), or aminoalkyl (C.sub.1-12);

(iv) a radical of formula IIIc, IIId or IIIe, ##STR101## wherein R.sub.11, R.sub.12 and R.sub.13, independently, are hydrogen or lower alkyl,

m is a whole number from 0 to 4,

n is a whole number from 0 to 3, and

v is a whole number from 0 to 5, or (v) a radical of formula IIIf, ##STR102## wherein R.sub.14 is lower alkyl, alkoxy (C.sub.1-12)carbonyl, alkenyl (C.sub.3-12), or alkynyl(C.sub.3-12),

R.sub.15 and R.sub.16, independently, are hydrogen or lower alkyl, and

q is a whole number from 0 to 5,

or a chemotherapeutically acceptable salt thereof.

38. A compound according to claim 37 in which R.sub.1 is ##STR103## and R.sub.6 is ##STR104## where m, n, v, R.sub.7, R.sub.8, R.sub.11, R.sub.12 and R.sub.13 are as defined in claim 37.

39. A compound according to claim 37 in which R.sub.1 is ##STR105## and R.sub.6 is ##STR106## and q, R.sub.7, R.sub.8, R.sub.14, R.sub.15 and R.sub.16 are as defined in claim 37.

40. A compound according to claim 37 in which q is 0 or 1.

41. A compound according to claim 1 in which R.sub.1 is ##STR107## and s, t, X and R.sub.9 are as defined in claim 1.

42. A compound according to claim 1 in which R.sub.1 and R.sub.2 together with the carbon atom to which they are bound form a radical of formula IIf or IIg, ##STR108## wherein p is 1, 2 or 3.
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