Claims
- 1. A method for the preparation of a compound of the formula VII: ##STR40## where X is a halogen atom;
- R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group; and
- R.sup.3 is hydrogen, an alkyl group or an aryl group,
- or a pharmaceutically acceptable salt thereof,
- comprising the step of reacting a compound of the formula V: ##STR41## where X and R.sup.3 are as defined in the formula VII, or a pharmaceutically acceptable salt thereof, with a compound of the formula VIa, VIb or VIc: ##STR42## where R.sup.1 and R.sup.2 are as defined in the formula VII;
- R.sup.1b and R.sup.2b are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atoms to which they are attached, form a 1,2-cycloalkenyl group; and
- R.sup.5 and R.sup.6 are each independently an alkyl group, in the presence of an acidic condensation agent,
- wherein alkyl employed herein alone or as part of another group has from 1 to 21 carbons;
- cycloalkyl employed herein alone or as part of another group has from 3 to 21 carbons;
- aryl employed herein alone or as part of another group has from 6 to 12 carbons;
- cycloalkenyl employed herein alone or as part of another group has from 3 to 21 carbons.
- 2. The method of claim 1, wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration Va is employed: ##STR43## and wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration VIIa is prepared: ##STR44##
- 3. A compound of the formula VII: ##STR45## where X is a halogen atom;
- R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group; and
- R.sup.3 is hydrogen, an alkyl group, or an aryl group,
- or a pharmaceutically acceptable salt thereof,
- wherein alkyl employed herein alone or as part of another group has from 1 to 21 carbons;
- cycloalkyl employed herein alone or as part of another group has from 3 to 21 carbons;
- aryl employed herein alone or as part of another group has from 6 to 12 carbons.
- 4. The compound as defined in claim 3, wherein said compound or pharmaceutically acceptable salt thereof has the stereoisomeric configuration VIIa: ##STR46##
- 5. A method for the preparation of a compound of the formula VIII: ##STR47## where R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group;
- R.sup.3 is hydrogen, an alkyl group or an aryl group; and
- R.sup.7 is an alkyl group or an aryl group;
- or a pharmaceutically acceptable salt thereof, comprising the step of displacing the group X of a compound of the formula VII: ##STR48## where x is a halogen atom; and
- R.sup.1, R.sup.2 and R.sup.3 are as defined in the formula VIII,
- or a pharmaceutically acceptable salt thereof, with an acyloxy group of the formula --O--C(O)--R.sup.7, by use of a displacement agent,
- wherein alkyl employed herein alone or as part of another group has from 1 to 21 carbons;
- cycloalkyl employed herein alone or as part of another group has from 3 to 21 carbons;
- aryl employed herein alone or as part of another group has from 6 to 12 carbons.
- 6. The method of claim 5, wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration VIIa is employed: ##STR49## and wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration VIIa is prepared: ##STR50##
- 7. The method of claim 5, wherein a compound of the formula IX: ##STR51## where M is a metal or an ammonium group; and R.sup.7 is as defined for the formula VIII, is employed as said displacement agent.
- 8. A compound of the formula VIII: ##STR52## where R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group;
- R.sup.3 is hydrogen, an alkyl group or an aryl group; and
- R.sup.7 is an alkyl group,
- of a pharmaceutically acceptable salt thereof,
- wherein alkyl employed herein alone or as part of another group has from 1 to 21 carbons;
- cycloalkyl employed herein alone or as part of another group has from 3 to 21 carbons;
- aryl employed herein alone or as part of another group has from 6 to 12 carbons.
- 9. The compound as defined in claim 8, wherein said compound or pharmaceutically acceptable salt thereof has the stereoisomeric configuration VIIIa: ##STR53##
- 10. A method for the preparation of a compound of the formula I: ##STR54## where R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group; and
- R.sup.3 is hydrogen, an alkyl group, or an aryl group;
- or a pharmaceutically acceptable salt thereof: ##STR55## where R.sup.1, R.sup.2 and R.sup.3 are as defined in the formula I, and
- (i) R.sup.7 is an alkyl group; or
- (ii) said hydrolysis is conducted employing a mild base and/or a mildly basic medium and R.sup.7 is an alkyl group or an aryl group,
- wherein alkyl employed herein alone or as part of another group has from 1 to 21 carbons;
- cycloalkyl employed herein alone or as part of another group has from 3 to 21 carbons;
- aryl employed herein alone or as part of another group has from 6 to 12 carbons.
- 11. The method of claim 10, wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration VIIIa is employed: ##STR56## and wherein a compound or pharmaceutically acceptable salt thereof having the stereoisomeric configuration Ia is prepared: ##STR57##
Parent Case Info
This is a division of application Ser. No. 08/135,604, filed Oct. 8, 1993, U.S. Pat. No. 5,457,227 which is a division of application Ser. No. 07/585,907, filed Mar. 27, 1992, U.S. Pat. No. 5,278,313.
US Referenced Citations (12)
Foreign Referenced Citations (3)
Number |
Date |
Country |
2662688 |
Jun 1989 |
AUX |
0319847 |
Jun 1989 |
EPX |
0374922 |
Jun 1990 |
EPX |
Non-Patent Literature Citations (4)
Entry |
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Divisions (2)
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Number |
Date |
Country |
Parent |
135604 |
Oct 1993 |
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Parent |
858907 |
Mar 1992 |
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