Claims
- 1. A novel genipin compound represented by the following formula (I)a : in whichR1 represents lower alkyl; R2 represents lower alkyl, pyridylcarbonyl, benzyl or benzoyl; R3 represents formyl, hydroxymethyl, azidomethyl, 1-hydroxyethyl, acetyl, methyl, hydroxy, pyridylcarbonyl, cyclopropyl, aminomethyl substituted or unsubstituted by (1,3-benzodioxolan-5-yl)carbonyl or 3,4,5-trimethoxybenzoyl, 1,3-benzodioxolan-5-yl, ureidomethyl substituted or unsubstituted by 3,4,5-trimethoxyphenyl or 2-chloro-6-methyl-3-pyridyl, thiomethyl substituted or unsubstituted by acetyl or 2-acetylamino2-ethoxycarbonyethyl, oxymethyl substituted or unsubstituted by benzoyl, pyridylcarbonyl or 3,4,5-trimethoxybenzoyl; provided that R3 is not methyl formyl, hydroxymethyl, acetyl, methylaminomethyl, acetylthiomethyl, benzoyloxymethyl or pyridylcarbonyloxymethyl when R1 is methyl, and its pharaceutically acceptable salts, or stereoisomers.
- 2. A novel genipin compound represented by the following formula (I)b: in whichR4 represents lower alkoxy, benzyloxy, benzoyloxy, phenylthio, C1˜C12 alkanyloxy substituted or unsubstituted by t-butyl, phenyl, phenoxy, pyridyl or thienyl; R5 represents methoxycarbonyl, formyl, hydroxyiminomethyl, methoxyimino-methyl, hydroxymethyl, phenylthiomethyl or acetylthiomethyl; provided that R5 is not methoxycarbonyl when R4 is acetyloxy; and its pharmaceutically acceptable salts, or stereoisomers.
- 3. A novel genipin compound represented by the following formula (I)c : R6 represents hydrogen atom, lower alkyl or alkalimetal; R7 represents lower alkyl or benzyl; R8 represents hydrogen atom or lower alkyl; R9 represents hydroxy, lower alkoxy, benzyloxy, nicotinoyloxy, isonicotinoyloxy, 2-pyridylmethoxy or hydroxycarbonylmethoxy; provided that R9 is not hydroxy or methoxy when R6 is methyl and R8 is hydrogen atom; and its pharmaceutically acceptable salts, or stereoisomers.
- 4. A novel genipin compound represented by the following formula (I)d; in whichR10 represents lower alkyl; R11 represents lower alkyl or benzyl; R12 represents lower alkyl, pyridyl substituted or unsubstituted by halogen, pyridylamino substituted or unsubstituted by lower alkyl or halogen, 1,3-benzodioxolanyl; R13 and R14 each independently represent a hydrogen atom or join together to form isopropylidene; and its pharmaceutically acceptable salts, or stereoisomers.
- 5. The compound of claim 1, wherein R1 represents methyl, R2 represents benzyl or methyl and R3 represents 1-hydroxyethyl, aminomethyl, 3,4,5-trimethoxy-benzoylaminomethyl, N-hydroxy-N-methylaminomethyl or 3,4,5-trimethoxy-phenylureidomethyl.
- 6. The compound of claim 2, wherein R4 represents acetyloxy when R5 is acetylthiomethyl, formyl, hydroxyiminomethyl or methoxyiminomethyl; R4 represents acetylthio when R5 is methoxycarbonyl, acetylthiomethyl, formyl or methoxyiminomethyl; R4 represents t-butylacetyloxy when R5 is methoxycarbonyl, acetylthiomethyl or formyl; R4 represents isonicotinclyoxy when R5 is methoxycarbonyl or acetylthiomethyl; R4 represents benzyloxy, phenylthio, pivaloyloxy, lauroyloxy, phenylacetyloxy, hydrosynamoyloxy, phenoxyacetyloxy, thiophenacetyloxy or benzoyloxy when R5 is methoxycarbonyl.
- 7. The compound of claim 3, wherein R6 represents hydrogen atom, methyl, isopropyl or sodium, R7 represents methyl or benzyl, R8 represents hydrogen atom or methyl, and R9 represents hydroxy, methoxy, t-butyl, benzyloxy, nicotinoyloxy, isonicotinoyloxy, 2-pyridylmethoxy or hydroxycarbonylmethoxy.
- 8. The compound of claim 4, wherein R10 represents methyl, R11 represents methyl or benzyl, R12 represents 3-pyridyl, 2-chloro-6-methyl-3-pyridyl, 3-pyridylamino, 2-chloro-3-pyridylamino, 2-chloro-6-methyl-3-pyridylamino, 5,6-dichloro-3-pyridyl-amino or 1,3-benzodioxolan-5-yl and R13 and R14 each independently represent a hydrogen atom or join together to form isopropylidene.
- 9. A pharmaceutical composition comprising the compound disclosed in any one of the preceding claims 1 to 8 as an active ingredient together with a pharmaceutically acceptable inert carrier.
- 10. The pharmaceutical composition of claim 9, wherein the inert carrier is one or more selected from a group consisting of lactose, starch, mannitol and cottonseed oil.
- 11. A method of treating hepatitis B liver disease, the method comprising:administering a pharmacologically effective amount of a pharmaceutical composition as recited in claim 9 to a patient in need thereof.
Priority Claims (3)
| Number |
Date |
Country |
Kind |
| 97-58131 |
Nov 1997 |
KR |
|
| 97-66389 |
Dec 1997 |
KR |
|
| 97-67407 |
Dec 1997 |
KR |
|
Parent Case Info
This application is the national phase under 35 U.S.C. § 371 of PCT International Application No. PCT/KR98/00273 which has an International filing date of Sep. 4, 1998, which designated the United States of America.
PCT Information
| Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
| PCT/KR98/00273 |
|
WO |
00 |
5/5/2000 |
5/5/2000 |
| Publishing Document |
Publishing Date |
Country |
Kind |
| WO99/23090 |
5/14/1999 |
WO |
A |
Foreign Referenced Citations (3)
| Number |
Date |
Country |
| A1 4323567 |
Jan 1994 |
DE |
| 066682 |
Mar 1991 |
JP |
| A1 9817663 |
Apr 1998 |
WO |
Non-Patent Literature Citations (1)
| Entry |
| Bentley et al., Chem. Abstracts Citation of J. Chem. Soc. C, vol. 21, pp. 2234-2240, 1967. |
Patent Grant
6262083
