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Last Updated: March 28, 2024

Claims for Patent: 7,169,928


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Summary for Patent: 7,169,928
Title:Non-imidazole alkylamines as histamine H.sub.3-receptor ligands and their therapeutic applications
Abstract: Use of a compound of formula (A), wherein: ##STR00001## W is a residue which imparts antagonistic and/or agonistic activity at histamine H.sub.3-receptors when attached to an imidazole ring in 4(5) position; R.sup.1 and R.sup.2 may be identical or different and represent each independently a lower alkyl or cycloalkyl, or taken together with the nitrogen atom to which they are attached, a saturated nitrogen-containing ring (i) as defined, a non-aromatic unsaturated nitrogen-containing ring (ii) as defined, a morpholino group, or a N-substituted piperazino group as defined for preparing medicaments acting as antagonists and/or agonists at the H.sub.3-receptors of histamine.
Inventor(s): Schwartz; Jean-Charles (Paris, FR), Arrang; Jean-Michel (Dourdan, FR), Garbarg; Monique (Paris, FR), Lecomte; Jeanne-Marie (Paris, FR), Ligneau; Xavier (Paris, FR), Schunack; Walter G. (Berlin, DE), Stark; Holger (Berlin, DE), Ganellin; Charon Robin (Welwyn, GB), Leurquin; Fabien (London, GB), Elz; Sigurd (Berlin, DE)
Assignee: Societe Civile Bioproject (Paris, FR)
Application Number:10/856,838
Patent Claims: 1. A compound of formula (IIa) ##STR00328## wherein: R.sup.1 and R.sup.2 form together with the nitrogen to which they are attached a saturated nitrogen-containing ring ##STR00329## with m ranging from 2 to 8 and R.sup.a-b being independently a hydrogen atom or a lower alkyl, and (i') the chain A.sup.II selected from an unbranched alkyl group --(CH.sub.2).sub.nII--where n.sub.II is 3; (ii') the group X'' is --O--; (iii') the chain B.sup.II is an unbranched alkyl comprising 3 carbon atoms; and (iv') the group Y.sup.II represents a phenyl group, unsubstituted or mono- or polysubstituted with one or more identical or different substituents selected from halogen atoms, OCF.sub.3, CHO, CF.sub.3, SO.sub.2N(alkyl).sub.2 NO.sub.2, S(aryl), SCH.sub.2(phenyl), an unbranched or branched alkene, an unbranched or branched alkyne optionally substituted with a trialkylsilyl radical, --O(alkyl), --O(aryl), --CH.sub.2CN, a ketone, an aldehyde, a sulphone, an acetal, an alcohol, a lower alkyl, --CH.dbd.CH--CHO, --C(alkyl).dbd.N--OH, --C(alkyl).dbd.N--O(alkyl) and derivatives, --CH.dbd.NOH, --CH.dbd.NO(alkyl), --C(alkyl).dbd.NH--NH--CONH.sub.2, an O-phenyl or --OCH.sub.2(phenyl) group, --C(cycloalkyl).dbd.NOH, --C(cycloalkyl).dbd.N--O(alkyl); or its pharmaceutically acceptable salts, hydrates, or hydrated salts, or their optical isomers, racemates, diastereoisomers or enantiomers.

2. The compound according to claim 1, wherein --R.sup.1R.sup.2 is a saturated nitrogen-containing ring: ##STR00330## R.sup.a and m being as defined in claim 1.

3. The compound according to claim 2, wherein m is 4 or 5.

4. The compound according to claim 3, wherein --NR.sup.1R.sup.2 is selected from the group consisting in piperidyl, pyrrolidinyl.

5. The compound according to claim 2, wherein R.sup.a is a hydrogen atom.

6. The compound according to claim 2, wherein the nitrogen-containing ring i) is one of mono- and di-substituted.

7. The compound according to claim 6, wherein the nitrogen-containing ring i) is mono-substituted with an alkyl group.

8. The compound according to claim 6, wherein the nitrogen-containing ring is mono-substituted with a methyl group.

9. The compound according to claim 6, wherein the substituent(s) is(are) in beta-position with respect to the nitrogen atom.

10. The compound according to claim 1, wherein Y.sup.II represents a phenyl group at least mono-substituted with a keto-substituent.

11. The compound according to claim 1, wherein Y.sup.II is a phenyl group at least mono-substituted with a halogen atom, --CHO, a ketone, an aldehyde, --CH.dbd.CH--CHO, --C(alkyl).dbd.N--OH, --C(alkyl).dbd.N--O(alkyl) and other keto derivatives, --CH.dbd.N--OH, --CH.dbd.NO(alkyl) and other aldehyde derivatives, --C(cycloalkyl).dbd.NOH, --C(cycloalkyl).dbd.N--O(alkyl).

12. The compound according to claim 1, wherein the compound is selected from: 3-Phenylpropyl 3-piperidinopropyl ether 3-(4-Ghlorophenyl)propyl 3-piperidinopropyl ether 3-Phenylpropyl 3-(4-methylpiperidino)propyl ether 3-Phenylpropyl 3-(3,5-cis-dimethylpiperidino)propyl ether 3-Phenylpropyl 3-(3,5-trans-dimethylpiperidino)propyl ether 3-Phenylpropyl 3-(3-methylpiperidino)propyl ether 3-Phenylpropyl 3-pyrrolidinopropyl ether 3-(4-Chlorophenyl)propyl 3-(4-methylpiperidino)propyl ether 3-(4-Chlorophenyl) propyl 3-(3,5-cis-dimethyl piperidino)propyl ether 3-(4-Chlorophenyl) propyl 3-(3,5-trans-dimethyl piperidino)propyl ether or its pharmaceutically acceptable salts, hydrates, or hydrated salts, or their optical isomers, racemates, diastereoisomers or enantiomers.

13. The compound according to claim 1, wherein the compound is 3-(4-chlorophenyl)propyl-3-piperidinopropylether, or its pharmaceutically acceptable salts, hydrates, or hydrated salts, or its optical isomers, racemates, diastereoisomers or enantiomers.

14. The compound according to claim 1, in the form of a pharmaceutical salt chosen from the group consisting in hydrochloride, hydrobromide, hydrogen maleate or hydrogen oxalate.

15. A pharmaceutical composition comprising a compound of formula (Ila) as defined in claim 1 with a pharmaceutically acceptable vehicle or excipient.

16. A pharmaceutical composition according to claim 15 comprising 3-(4-chlorophenyl)propyl-3-piperidinopropylether or its pharmaceutically acceptable salts, hydrates, or hydrated salts, racemates, diastereoisomers or enantiomers with a pharmaceutically acceptable vehicle or excipient.

17. The compound according to claim 10 wherein the keto-substituent includes a linear or branched chain aliphatic ketone comprising from 1 to 8 carbon atoms and optionally bearing a hydroxyl group, a cycloalkylketone, an arylalkylketone or arylalkenylketone in which the aryl group is optionally substituted, or a heteroaryl ketone.

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