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Last Updated: April 25, 2024

Claims for Patent: 5,434,171

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Summary for Patent: 5,434,171

Title:	Preparation of 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates and intermediates
Abstract:	This invention relates to a process for preparing certain 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates, intermediates, and congeners. Finally, the invention provides new 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates with formulations and methods for using the compounds.
Inventor(s):	Frank; Scott A. (Lebanon, IN), Prather; Douglas E. (Brownsburg, IN), Ward; Jeffrey A. (Indianapolis, IN), Werner; John A. (Indianapolis, IN)
Assignee:	Eli Lilly and Company (Indianapolis, IN)
Application Number:	08/164,074
Patent Claims:	1. A crystalline compound of the Formula 20 ##STR14## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; Z1.sup.- is selected from the group consisting of hydrochloride, malate, and sesquimalate; wherein when Z1.sup.- is sesquimalate then 3 molecules of malate are associated with 2 molecules of 20; and when Z1.sup.- is hydrochloride then each molecule of 20 is solvated with one molecule of acetone. 2. A crystalline compound of claim 1 wherein Z1.sup.- is hydrochloride. 3. A crystalline compound of claim 1 wherein Z1.sup.- is sesquimalate. 4. A crystalline compound of claim 1 wherein the compound of Formula 1 is (2S, 3R, 4R)[[2-[[4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-ph enylpropyl]amino]acetic acid 2-methylpropyl ester. 5. A crystalline compound of claim 2 wherein the compound is (2S, 3R, 4R)[[2-[[4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-ph enylpropyl]-amino]acetic acid 2-methylpropyl ester hydrochloride acetone monosolvate. 6. A crystalline compound of claim 3 wherein the compound is (2S, 3R, 4R)[[2-[[4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-ph enylpropyl]-amino]acetic acid 2-methylpropyl ester. 7. A crystalline compound of claim 1 wherein the compound is (2S, 3R, 4R)[[2-[[4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-ph enylpropyl]-amino]acetic acid 2-methylpropyl ester malate. 8. A crystalline dihydrate compound of the Formula 5 ##STR15## 9. A compound of claim 8 wherein the crystalline dihydrate compound is at least 97% (2S,3R,4R)dihydrate. 10. A method for binding a peripheral opioid receptor in a patient which comprises administering to said patient an effective amount of a compound of claim 1. 11. A method for binding a peripheral opioid receptor in a patient which comprises administering to said patient an effective amount of a compound of claim 8. 12. A method for treating a condition selected from the group consisting of irritable bowel syndrome, idiopathic constipation, and non-ulcer dyspepsia; comprising administering an effective amount of a compound of claim 1. 13. A method for treating a condition selected from the group consisting of irritable bowel syndrome, idiopathic constipation, and non-ulcer dyspepsia; comprising administering an effective amount of a compound of claim 8. 14. A pharmaceutical formulation comprising an effective amount of a compound of claim 1 in combination with one or more pharmaceutically acceptable excipients. 15. A pharmaceutical formulation comprising an effective amount of a compound of claim 8 in combination with one or more pharmaceutically acceptable excipients. 16. A formulation of claim 15 wherein the formulation is a hard gelatin capsule. 17. A process for preparing a crystalline monohydrate compound of Formula 3 ##STR16## comprising the crystallization of 3 from a solvent comprised of about 50% methanol and about 50% water (by weight).

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