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US 2011/0313032 A1Published application
Competitive inhibitors of type ii dehydroquinase enzyme
AssigneeUniversidade De Santiago De Compostela
InventorsCóncepcion González Bello, Verónica Filipa Vieira Prazeres, Sonia Paz Gómez, Cristina Sánchez Sixto, Lorena Tizón Valverde
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Abstract
The present invention is directed to a compound of formula (I), its diastereoisomers, its enantiomers or its pharmaceutically acceptable salts or solvates, formula (I), to procedures of obtaining the same, to intermediates thereof, and use as competitive inhibitors of the third enzyme of the shikimic acid pathway, the type II dehydroquinase.
Claims17
A compound of formula I, its diastereoisomers, its enantiomers or its pharmaceutically acceptable salts or solvates
- wherein,
- A represents a single or double bond;
- X is selected from the group consisting of —(C═O)ORa and —(C═O)NRbRc, wherein each of Ra, Rb and Rc is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heterocyclylalkyl;
- or Rb and Rc together form a 5 or 6 membered heterocyclyc ring together with the nitrogen atom to which they are attached;
- each P1, P2 and P3 is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted arylalkyl and —(C═O)Ra, wherein Ra is as defined above;
- and
- wherein
- if A is a double bond,
- then R2 is selected from the group consisting of —ORa, —SRa and —NRbRc, wherein Ra, Rb and Rc are as defined above;
- and R1 is hydrogen or R1a, wherein R1a is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heterocyclylalkyl, with the proviso that:
- when X is COOMe and P1, R1, P3 and P2 are H, then R2 is not methoxy,
- when X is COOMe, P1, P2 and P3 are SiMe3, and R1 is H, then R2 is not OH, and
- when X is COOH and P1, R1, P3 and P2 are H, then R2 is not OH;
- or
- R1 and R2 together form a 5-membered ring;
- and
- if A is a single bond,
- then R2 is ═O, ═S or ═NRb, wherein Rb is as defined above;
- and R1 is R1a, wherein R1a is as defined above.
16 more elements
A compound of formula I, its diastereoisomers, its enantiomers or its pharmaceutically acceptable salts or solvates
- wherein,
- A represents a single or double bond;
- X is selected from the group consisting of —(C═O)ORa and —(C═O)NRbRc, wherein each of Ra, Rb and Rc is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heterocyclylalkyl;
- or Rb and Rc together form a 5 or 6 membered heterocyclyc ring together with the nitrogen atom to which they are attached;
- each P1, P2 and P3 is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted arylalkyl and —(C═O)Ra, wherein Ra is as defined above;
- and wherein
- if A is a double bond,
- then R2 is selected from the group consisting of —ORa′, —SRa and —NRbRc, wherein Rb and Rc are as defined above;
- Ra′ is selected from the group consisting of substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heterocyclylalkyl;
- and R1 is hydrogen or R1a, wherein R1a is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heterocyclylalkyl, or
- R1 and R2 together form a 5-membered ring;
- and
- if A is a single bond,
- then R2 is ═O, ═S or ═NRb, wherein Rb is as defined above;
- and R1 is R1a, wherein Rla is a defined above.
12 more elements
Dependencies are inferred from the claim text.