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US 2007/0185108 A1Published application
Process of obtaining taxosteroids and precursors thereof
AssigneeUniversidade De Santiago De Compostela
InventorsJuan Granja Guillan, Luis Castedo Exposito, Rebeca Garcia Fandino
Life of this patent
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Abstract
The present invention relates to a process of obtaining taxosteroids and precursors thereof from the hydrindane bicyclic ring system. The compounds have a tetracyclic system which combines the structural characteristics of taxanes, such as the bicyclo[5.3.1]undecane system (cycles A and B), fused to a six-membered ring (C), and of steroids, such as the CD bicycle, the A ring and the side chain (Sc). The process of preparing the compounds and their application as compositions with pharmacological properties of interest are described.
Claims10
Compounds of formula (1), characterized by:
- wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 can be a hydrogen atom, an acyloxy, alkyloxy, aryloxy, alkylthio, arylthio or alkyl group with C1-C10 chains, in which the radical can be linear or branched alkyl with 1-10 carbon atoms, alkenyl with 2 to 10 carbon atoms, alkynyl with 3 to 10 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms or bicycloalkyl with 7 to 10 carbon atoms;
- these radicals possibly being substituted by one or several identical or different substituents chosen from halogen atoms and hydroxy, alkoxy radicals containing 1 to 4 carbon atoms, piperidinyl, morpholinyl, piperazinyl-1 (possibly substituted at −4 by an alkyl radical with 1 to 4 carbon atoms or by a phenylalkyl radical, the alkyl part of which contains 1 to 4 carbon atoms), cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms, phenyl, cyano, nitro, carboxy or alkoxycarbonyl, the alkyl part of which contains 1 to 4 carbon atoms, or a phenyl radical, possibly substituted by one or several identical or different radicals, chosen from alkyl radicals with 1 to 4 carbon atoms or alkoxy radicals containing 1 to 4 carbon atoms, a saturated or unsaturated nitrogenous heterocyclic radical containing 5 or 6 members, possibly substituted by one or several alkyl radicals with 1 to 4 carbon atoms, understanding that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can possibly be substituted by one or several alkyl radicals with 1 to 4 carbon atoms;
- and
- Sc is the characteristic side chain of steroids or a linear or branched alkyl radical with 1-12 carbon atoms, alkenyl with 2 to 12 carbon atoms, alkynyl with 3 to 12 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms or bicycloalkyl with 7 to 10 carbon atoms;
- these radicals possibly being substituted by one or several identical or different substituents chosen from halogen atoms and hydroxy, alkoxy radicals containing 1 to 4 carbon atoms, piperidinyl, morpholinyl, piperazinyl-1 (possibly substituted at −4 by an alkyl radical with 1 to 4 carbon atoms or by a phenylalkyl radical, the alkyl part of which contains 1 to 4 carbon atoms), cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms, phenyl, cyano, nitro, carboxy or alkoxycarbonyl, the alkyl part of which contains 1 to 4 carbon atoms, or a phenyl radical, possibly substituted by one or several identical or different radicals, chosen from alkyl radicals with 1 to 4 carbon atoms, or alkoxy radicals containing 1 to 4 carbon atoms, a saturated or unsaturated nitrogenous heterocyclic radical with 5 or 6 members, possibly substituted by one or several alkyl radicals with 1 to 4 carbon atoms, understanding that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can possibly be substituted by one or several alkyl radicals containing 1 to 4 carbon atoms;
- and
- Sk is an amino acid chain analogous to that of to taxanes, in which P represents a phenyl group or an alkoxy radical with alkyl chains with 1 to 10 carbon atoms, alkenyl and alkynyl chains with 3 to 10 carbon atoms, cycloalkyl and cycloalkenyl chains with 4 to 7 carbon atoms in the ring, a phenyl or a heterocyclic compound, and Ar is an aromatic compound.
4 more elements
Compounds of formula (2) characterized by:
- wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 can be a hydrogen atom, an acyloxy, alkyloxy, aryloxy, alkylthio, arylthio or alkyl group with C1-C10 chains, in which the radical can be linear or branched alkyl with 1-10 carbon atoms, alkenyl with 2 to 10 carbon atoms, alkynyl with 3 to 10 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms or bicycloalkyl with 7 to 10 carbon atoms;
- these radicals possibly being substituted by one or several identical or different substituents chosen from halogen atoms and hydroxy, alkoxy radicals containing 1 to 4 carbon atoms, piperidinyl, morpholinyl, piperazinyl-1 (possibly substituted at −4 by an alkyl radical with 1 to 4 carbon atoms or by a phenylalkyl radical, the alkyl part of which contains 1 to 4 carbon atoms), cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms, phenyl, cyano, nitro, carboxy or alkoxycarbonyl, the alkyl part of which contains 1 to 4 carbon atoms, or a phenyl radical, possibly substituted by one or several identical or different radicals, chosen from alkyl radicals with 1 to 4 carbon atoms or alkoxy radicals containing 1 to 4 carbon atoms, a saturated or unsaturated nitrogenous heterocyclic radical containing 5 or 6 members, possibly substituted by one or several alkyl radicals with 1 to 4 carbon atoms, understanding that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can possibly be substituted by one or several alky radicals with 1 to 4 carbon atoms;
- and
- Sc is the characteristic side chain of steroids or a linear or branched alkyl radical with 1-12 carbon atoms, alkenyl with 2 to 12 carbon atoms, alkynyl with 3 to 12 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms or bicycloalkyl with 7 to 10 carbon atoms;
- these radicals possibly being substituted by one or several identical or different substituents chosen from halogen atoms and hydroxy, alkoxy radicals containing 1 to 4 carbon atoms, piperidinyl, morpholinyl, piperazinyl-1 (possibly substituted at −4 by an alkyl radical with 1 to 4 carbon atoms or by a phenylalkyl radical, the alkyl part of which contains 1 to 4 carbon atoms), cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl with 4 to 6 carbon atoms, phenyl, cyano, nitro, carboxy or alkoxycarbonyl, the alkyl part of which contains 1 to 4 carbon atoms, or a phenyl radical, possibly substituted by one or several identical or different radicals, chosen from alkyl radicals with 1 to 4 carbon atoms, or alkoxy radicals containing 1 to 4 carbon atoms, a saturated or unsaturated nitrogenous heterocyclic radical with 5 or 6 members, possibly substituted by one or several alkyl radicals with 1 to 4 carbon atoms, understanding that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals can possibly be substituted by one or several alky radicals containing 1 to 4 carbon atoms;
- and
- Sk is an amino acid chain analogous to that of to taxanes, in which P represents a phenyl group or an alkoxy radical with alkyl chains with 1 to 10 carbon atoms, alkenyl and alkynyl chains with 3 to 10 carbon atoms, cycloalkyl and cycloalkenyl chains with 4 to 7 carbon atoms in the ring, a phenyl or a heterocyclic compound, and Ar is an aromatic compound.
4 more elements
Dependencies are inferred from the claim text.