Back to results
US 9,067,934 B2Granted
Bicyclic pyridinones
AssigneePfizer Inc.
InventorsMartin Youngjin Pettersson, Douglas Scott Johnson, Chakrapani Subramanyam, Christopher John O'Donnell, Christopher William am Ende, Benjamin Adam Fish, Michael Eric Green, Patrick Bradley Mullins, Cory Michael Stiff, Tuan Phong Tran, Thayalan Navaratnam
Life of this patent
Estimating the term…
Abstract
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined herein. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
Claims14
A compound having the structure of Formula I:
- wherein:
- X is a 5- to 14-membered heteroaryl containing 1-3 heteroatoms;
- R1 is hydrogen, halogen, C1-6alkyl;
- wherein said alkyl may be optionally and independently substituted with one to three of fluoro, cyano, —CF3, hydroxy, or C1-6alkoxy;
- R2a and R2b for each occurrence are each independently hydrogen, fluoro, cyano, —CF3, or C1-6alkyl;
- wherein said alkyl, may be optionally and independently substituted with cyano, C1-3alkyl or one to three fluoro;
- or R2a and R2b together with the carbon to which they are bonded form a 3- to 5-membered cycloalkyl optionally substituted with one to three R8;
- R3 is ) —(C(R11)2)t-(5- to 14-membered heteroaryl);
- wherein said heteroaryl moiety may be optionally independently substituted with one to five R10;
- R4a and R4b are each independently hydrogen, —CF3, or C1-6alkyl, wherein said alkyl is optionally substituted with one to three —CF3, cyano or fluoro;
- R5a and R5b for each occurrence are each independently hydrogen, —CF3, or C1-6alkyl, wherein said alkyl is optionally substituted with one to three —CF3, cyano or fluoro;
- R6, R7 and R8 are each independently hydrogen, —CF3, cyano, halogen, C1-6alkyl or —OR9;
- provided that R6 and R7 cannot both be —OH;
- R9 is hydrogen or, C1-6alkyl;
- wherein said alkyl may be optionally and independently substituted with cyano, or one to three fluoro;
- each R10 is independently hydrogen, halogen, cyano, —CF3, C1-6alkyl —(C(R11)2)m—OR12, —C(O)R13, —SF5 or —Si(CH3)3;
- wherein said alkyl, moieties may be optionally and independently substituted with one to three R14;
- each R11 is independently hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-4cycloalkyl, fluoro, —CF3, —CHF2 or —OR12;
- wherein said alkyl, alkenyl, alkynyl or cycloalkyl moieties may be optionally independently substituted with one to three fluoro or cyano;
- each R12 is independently hydrogen, C1-6alkyl, or —CF3;
- wherein said alkyl, may be optionally independently substituted with one to three R16;
- each R13 is independently C1-6alkyl;
- wherein said alkyl may be optionally independently substituted with one to three R16;
- each R14 is independently hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, halogen, cyano, —CF3, —CHF2, —OR9 or —OCF3;
- R16 is independently hydrogen, —CF3, cyano, halogen, C1-6alkyl or —OR9;
- wherein said alkyl moiety may be optionally substituted with one to three R17;
- R17 is independently hydrogen, hydroxyl, —CF3, cyano, fluoro, C2-6alkenyl or C2-6alkynyl;
- wherein said alkenyl or alkynyl moiety may be optionally substituted with one to three hydrogen, fluoro or C1-6alkyl;
- and
- each t or, m, is an integer independently selected from 0, 1, 2, 3 and 4;
- z is an integer selected from 1 and 2;
- y is an integer selected from 1, 2, 3 and 4;
- or a pharmaceutically acceptable salt thereof.
30 more elements
A compound selected from the group consisting of:
- 2-(2-{[4-fluoro-2-(trifluoromethyl)-1,3-benzothiazol-7-yl]oxy}ethyl)-7-(4-methyl-1H-imidazol-1-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione;
- 7-(4-methyl-1H-imidazol-1-yl)-2-(2-{[2-(trifluoromethyl)-1,3-benzothiazol-7-yl]oxy}ethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione;
- 2-{2-[(2,2-difluoro-2,3-dihydro-1H-inden-4-yl)oxy]ethyl}-7-(4-methyl-1H-imidazol-1-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione;
- 2-{2-[(2,2-difluoro-1,3-benzodioxol-4-yl)oxy]ethyl}-7-(4-methyl-1H-imidazol-1-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione;
- or a pharmaceutically acceptable salt of any of the above.
2 more elements
Dependencies are inferred from the claim text.