Claims
- 1. 1,3-diphenylpropane derivative represented by the following formula (I): ##STR28## in which - - represents double or single bond,
- R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl,
- R.sub.2 represents C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxyalkyl, or
- R.sub.1 and R.sub.2 together represent a 5 to 6 membered heterocycle which can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom,
- R.sub.3 represents hydrogen or C.sub.1 -C.sub.7 alkyl,
- R.sub.4 represents hydrogen, hydroxy, or oxo, and
- R.sub.5 and R.sub.6 independently of one another represent hydrogen or C.sub.1 -C.sub.5 alkyl.
- 2. The compound of claim 1, wherein R.sub.1 represents hydrogen, methyl or ethyl, R.sub.2 represents methyl, or R.sub.1 and R.sub.2 together represent ##STR29## R.sub.3 represents hydrogen or methyl, R.sub.4 represents hydrogen or hydroxy, and R.sub.5 and R.sub.6 independently of one another represent methyl.
- 3. A process for preparing a compound represented by the following formula (Ia), ##STR30## in which R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl,
- R.sub.2 represents C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxyalkyl, or
- R.sub.1 and R.sub.2 together represent a 5 to 6 membered heterocycle which can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom,
- R.sub.3 represents hydrogen or C.sub.1 -C.sub.7 alkyl,
- R.sub.5 and R.sub.6 independently of one another represent hydrogen or C.sub.1 -C.sub.5 alkyl, comprising the steps of:
- reducing a compound represented by the following formula (IV), ##STR31## in which P.sub.1 represents benzyl, methyl, ethyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl,
- P.sub.2 represents benzyl, methyl or ethyl
- P.sub.3 represents benzyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl, and
- R.sub.2, R.sub.5 and R.sub.6 are as defined above, in a solvent to produce a compound represented by the following formula (V), ##STR32## in which P.sub.1, P.sub.2 and P.sub.3 are defined as above and R.sub.2, R.sub.5 and R.sub.6 are as defined above; and then
- removing the protecting groups in the compound of formula (V).
- 4. The process of claim 3, wherein the reduction is carried out in a solvent selected from a group consisting of diethylether and tetrahydrofuran (THF) in the presence of lithium aluminum hydride(LAH).
- 5. The process of claim 4, wherein the reduction is carried out at temperatures ranging from -30 to 30.degree. C.
- 6. A process for preparing a compound represented by the following formula (Ib), ##STR33## in which R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl,
- R.sub.2 represents C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxyalkyl, or
- R.sub.1 and R.sub.2 together represent a 5 to 6 membered heterocycle which can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom,
- R.sub.3 represents hydrogen or C.sub.1 -C.sub.7 alkyl,
- R.sub.5 and R.sub.6 independently of one another represent hydrogen or C.sub.1 -C.sub.5 alkyl, comprising the steps of:
- hydrogenating the double bond in a compound represented by the following formula (IV), ##STR34## in which P.sub.1 represents benzyl, methyl, ethyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl,
- P.sub.2 represents benzyl, methyl or ethyl
- P.sub.3 represents benzyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl, and
- R.sub.2, R.sub.5 and R.sub.6 are as defined above, in a solvent to produce a compound represented by the following formula (V'), ##STR35## in which P.sub.1, P.sub.2 and P.sub.3 are as defined above and R.sub.2, R.sub.5 and R.sub.6 are as defined above; and then
- removing the protecting groups in the compound of formula (V').
- 7. The process of claim 6, wherein the solvent is ethylacetate.
- 8. The process of claim 6, wherein the protecting group is benzyl.
- 9. The process of claim 8, wherein the solvent is ethylacetate and the hydrogenation is carried out for 10 to 15 hours under normal temperature and pressures ranging from 2 to 4 atms.
- 10. The process of claim 8, wherein the solvent is a mixture of ethylacetate and a lower alcohol and the hydrogenation is carried out for 20 minutes to one hour under temperatures ranging from 35 to 55.degree. C. and normal pressure.
- 11. A process for preparing a compound represented by the following formula (Ic), ##STR36## in which R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl,
- R.sub.2 represents C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxalkyl, or
- R.sub.1 and R.sub.2 together represent a 5 to 6 membered heterocycle which can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom,
- R.sub.3 represents hydrogen or C.sub.1 -C.sub.7 alkyl,
- R.sub.5 and R.sub.6 independently of one another represent hydrogen or C.sub.1 -C.sub.5 alkyl, comprising the steps of:
- dehydrating a compound represented by the following formula (V), ##STR37## in which P.sub.1 represents benzyl, methyl, ethyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl,
- P.sub.2 represents benzyl, methyl or ethyl
- P.sub.3 represents benzyl, tetrahydropyranyl, methoxymethyl, methoxyethoxymethyl or p-methoxybenzyl, and
- R.sub.2, R.sub.5 and R.sub.6 are as defined above, in a solvent to produce a compound represented by the following formula (VI), ##STR38## in which P.sub.1, P.sub.2 and P.sub.3 are as defined above and R.sub.2, R.sub.5 and R.sub.6 are as defined above; and then
- reducing and deprotecting the compound of formula (V) thus produced.
- 12. The process of claim 11, wherein the dehydration is carried out in a solvent selected from a group consisting of benzene, toluene and xylene in the presence of an acid selected from a group consisting of sulfuric acid, phosphoric acid and p-toluenesulfonic acid.
- 13. The process of claim 12, wherein the dehydration is carried out at temperatures ranging from 80 to 100.degree. C.
- 14. The process of claim 6, wherein the protecting group is benzyl and the compound of formula (Ib) is produced by carrying out the hydrogenation and deprotection of the compound of formula (IV) in ethyl acetate or a solvent mixture of ethyl acetate and a lower alcohol.
Priority Claims (1)
Number |
Date |
Country |
Kind |
97/7452 |
Mar 1997 |
KRX |
|
Parent Case Info
This application is the national phase under 35 U.S.C. .sctn.371 of prior PCT International Application No. PCT/KR98/00039 which has an International filing date of Mar. 2, 1998 which designated the United States of America, the entire contents of which are hereby incorporated by reference.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/KR98/00039 |
3/2/1998 |
|
|
11/6/1998 |
11/6/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO98/39279 |
9/11/1998 |
|
|
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