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US 6,274,768 B1Granted
Acridin derivatives
AssigneeGruenenthal GmbH
InventorsClaudia Katharina Puetz, Wolfgang Werner Alfred Strassburger, Oswald Zimmer, Werner Guenter Englberger
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Abstract
This invention relates to intermediates in the preparation of acridin derivatives of general formula or pharmaceutically acceptable salts thereof, and to a method of producing them.
Claims20
A compound corresponding to a formula selected from the group consisting of:
- wherein
- R14 and R15 may be the same or different and are each independently selected from the group consisting of C1-6-alkyl, aryl and C3-7-cycloalkyl;
- and
- R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, or a pharmaceutically acceptable salt thereof.
1 more element
A method of preparing a compound corresponding to the formula IVa
- wherein
- R14 and R15 may be the same or different and are each independently selected from the group consisting of C2-6-alkyl, aryl and C3-7-cycloalkyl;
- and
- R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl,
- said method comprising:
- reacting 3,3-dimethyl-1,5-dioxa-spiro[5.5]-undecan-8-one corresponding to the formula:
- with an immonium salt corresponding to the formula V:
- wherein R14 and R15 have the meanings given above, to obtain a Mannich base corresponding to the formula VII:
- wherein R14 and R15 have the meanings given above,
- thereafter reacting the Mannich base of formula VII with an organometallic compound corresponding to formula VI:
- wherein
- Z represents MgCl, MgBr MgI or lithium, and
- R22 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl,
- to obtain a compound corresponding to formula III:
- wherein
- R14 and R15 have the meanings given above, and
- R20 has the meaning given above for R21, and
- then reacting the compound corresponding to formula III with an acid to obtain the compound corresponding to formula IVa.
15 more elements
A cyclohexenone compound corresponding to the formula:
- wherein
- R14 and R15 may be the same or different and are each independently selected from the group consisting of C2-6-alkyl, aryl and C3-7-cycloalkyl;
- and
- R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, said compound being produced by the process of treating a dioxa-spiro compound containing a tertiary OH group corresponding to formula III
- wherein
- R14 and R15 have the meanings given above;
- and
- R20 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl,
- with an acid under conditions to effect elimination of the tertiary OH group with formation of a double bond and conversion of the dioxa-spiro linkage to a keto group.
6 more elements
Dependencies are inferred from the claim text.