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Details for Patent: 4,816,484

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Details for Patent: 4,816,484

Title: Hypoglycemic agent
Abstract:A compound of D-phenylalanine derivative for hypoglycemic use, represented by the general formula ##STR1## R.sup.1 is selected from hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 12 carbon atoms, aralkyl of 6 to 12 carbon atoms, ##STR2## --CH.sub.2 CO.sub.2 R.sup.3, --CH(CH.sub.3)--OCO--R.sup.3, and --CH.sub.2 --OCO--C(CH.sub.3).sub.3 ; R.sup.2 is selected from groups comprising aryl of 6 to 12 carbon atoms, a hetero six-membered ring, a hetero five-membered ring, cycloalkyl, or cycloalkenyl, any of which groups may have one or more substituents; and R.sup.3 is selected from hydrogen and alkyl of 1 to 5 carbon atoms; the salts thereof, and precursors which can be converted thereto in the human or animal body. Some of the compounds are novel per se.
Inventor(s): Toyoshima; Shigeshi (Funabashi, JP), Seto; Yoshiko (Funabashi, JP), Shinkai; Hisashi (Kawasaki, JP), Toi; Koji (Kanagawa, JP), Kumashiro; Izumi (Yokohama, JP)
Assignee: Ajinomoto Co., Inc. (Tokyo, JP)
Filing Date:Jan 21, 1988
Application Number:07/146,719
Claims:1. A D-phenylalanine derivative of the formula

or a salt thereof or a precursor which can be converted into said D-phenylalanine derivative in vivo, wherein:

R.sup.1 is hydrogen or C.sub.1-5 alkyl,

R.sup.3 is hydrogen or C.sub.1-5 alkyl; and

R.sup.4 is cyclohexane substituted at the 4- or 5-position by methyl, ethyl, ispropyl, tert-butyl, ethene, or isopropene or cyclohexane substituted at the 4- or 5-position by methyl, ethyl, isopropyl, tert-butyl, ethene, or isopropene.

2. The D-phenylalanine derivative of claim 1, wherein R.sup.4 is said substituted cyclohexane.

3. The D-phenylalanine derivative of claim 1, wherein R.sup.4 is said substituted cyclohexane.

4. The D-phenylalanine derivative of claim 1, wherein the said derivative is N-(4-isopropylcyclohexylcarbonyl)-D-phenylalanine.

5. The D-phenylalanine derivative of claim 1, wherein the said derivative is N-(4-isopropylcyclohexylcarbonyl)-D-phenylalanine; N-[(S)-perilloyl]-D-phenylalanine; N-(4-methylcyclohexylcarbonyl)-D-phenylalanine; N-(4-ethylcyclohexylcarbonyl)-D-phhenylalanine; or N-(4-t-butylcyclohexylcarbonyl)-D-phenylalanine.

6. The D-phenylalanine derivataive of claim 1, wherein the said derivative is N-[(s)-perilloyl]-D-phenylalanine; N-(trans-4-methylcyclohexylcarbonyl)-D-phenylalanine; N-(trans-4-ethylcyclohexylcarbonyl)-D-phenylalanine; N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine; or N-(trans-4-t-butylcyclohexylcarbonyl)-D-phenylalanine.

7. The D-phenylalanine derivative of claim 1, wherein R.sup.1 is hydrogen and R.sup.3 is hydrogen.

8. The D-phenylalanine derivative of claim 1, wherein R.sup.4 is perilloyl.

9. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexane is substituted at the 4-position.

10. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexane is substituted at the 5-position.

11. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexene is substituted at the 4-position.

12. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexene is substituted at the 5-positon.

13. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexane or said substituted cyclohexene is substituted with methyl, ethyl, isopropyl or tert-butyl.

14. The D-phenylalanine derivative of claim 1, wherein said substituted cyclohexane or said substituted cyclohexene is substituted by ethene, or isopropene.

15. A pharmaceutical composition, comprising a D-phenylalanine derivative of claim 1 and a pharmaceutical excipient.
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