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US 9,926,264 B2Granted
Phenylcarbamate derivatives as formyl peptide receptor modulators
AssigneeAllergan, Inc.
InventorsRichard L. Beard, Tien T. Duong, Michael E. Garst
Life of this patent
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Abstract
The present invention relates to N-phenyl carbamate derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of the N-formyl peptide 2 receptor.
Claims10
A compound of Formula I:
- wherein:
- R1 is optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, halogen, NR11R12, fluorinated C1-8 alkyl, perfluorinated C1-8 alkyl, —S(O)mR13, —C(O)R14 or —OR15;
- R2 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, halogen, NR11R12, fluorinated C1-8 alkyl, perfluorinated C1-8 alkyl, —S(O)mR13, —C(O)R14 or —OR15;
- R3 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, halogen, NR11R12, fluorinated C1-8 alkyl, perfluorinated C1-8 alkyl, —S(O)mR13, —C(O)R14 or —OR15;
- R4 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, halogen, NR11R12, fluorinated C1-8 alkyl, perfluorinated C1-8 alkyl, —S(O)mR13—C(O)R14 or —OR15;
- R5 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, halogen, NR11R12, fluorinated C1-8 alkyl, perfluorinated C1-8 alkyl, —S(O)mR13, —C(O)R14 or —OR15;
- R6 is H, optionally substituted C1-8 alkyl, optionally substituted heterocycle, (CH2)pCOOH, —(CH2)p—NH2, —(CH2)p—OH, —(CH2)p—SH, —(CH2)p—CONH2, —(CH2)p—CONH2, —CH(OH)CH3, —(CH2)pSCH3, —(CH2)pNH—C(═NH)(NH2) or —CH2C6-10aryl, wherein said —C6-10aryl is optionally substituted;
- R6a is H or optionally substituted C1-8 alkyl;
- R7 is H or optionally substituted C1-8 alkyl;
- R8 is H;
- R9 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl or optionally substituted C3-8 cycloalkenyl;
- R10 is —(CH2)nOR16, —(CH2)—S(O)2OH, —(CH2)nC(O)R17, —(CH2)nOS(O)2OH, (CH2)nNR18R19, —(CH2)—P(O)(OC1-6 alkyl)2, —(CH2)nP(O)(OC1-6 alkyl)OH, —(CH2)n—P(O)(OH)2 or optionally substituted heterocycle;
- R11 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl or optionally substituted C3-8 cycloalkenyl;
- R12 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl or optionally substituted C3-8 cycloalkenyl;
- R13 is H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, OH or optionally substituted C3-8 cycloalkenyl;
- R14 is optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl or —OR15;
- R15 is H or optionally substituted C1-8 alkyl;
- R16 is H, —C(O)(C1-8 alkyl) or optionally substituted C1-8 alkyl;
- R17 is OH, —OC1-8 alkyl or C1-8 alkyl;
- R18 is selected from the group consisting of H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkenyl, —C(O)R17 and —S(O)2N(C1-8 alkyl)2;
- R19 is selected from the group consisting of H, optionally substituted C1-8 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C6-10 aryl, or optionally substituted C3-8 cycloalkenyl, —C(O)R17 and —S(O)2N(C1-8 alkyl)2;
- with a proviso when R10 is —(CH)nC(O)R17 and R17 is C1-8 alkyl, then R9 is H;
- p is 1, 2 or 3;
- n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
- and
- m is 0, 1 or 2;
- wherein
- each C1-8 alkyl substituent is independently selected from the group consisting of halogen, hydroxyl, —OC1-8alkyl, C3-8cycloalkyl, amino, heterocycle, C6-10aryl, carboxylic acid, phosphonic acid, sulphonic acid, phosphoric acid, nitro, amide, sulfonamide, sulfonamide and carboxylate ester;
- each C3-8 cycloalkyl substituent is independently selected from the group consisting of halogen, hydroxyl, sulfonyl C1-8 alkyl, sulfoxide C1-8 alkyl, sulfonamide, nitro, —OC1-8 alkyl, —SC1-8 alkyl groups, —C1-8 alkyl, ketone, alkylamino, amino, C6-10 aryl and C3-8 cycloalkyl;
- each heterocycle substituent is independently selected from the group consisting of halogen, hydroxyl, —OC1-8 alkyl, sulfonyl C1-8 alkyl, sulfoxide C1-8 alkyl, nitro, —SC1-8 alkyl, —C1-8 alkyl, ketone, alkylamino, amino, C6-10 aryl and C3-8 cycloalkyl;
- each C6-10 aryl substituent is independently selected from the group consisting of halogen, hydroxyl, sulfonyl C1-8 alkyl, sulfoxide C1-8 alkyl, sulfonamide, carboxylic acid, C1-8 alkyl carboxylate (ester), amide, nitro, —OC1-6 alkyl, —SC1-8 alkyl, —C1-8 alkyl, ketone, alkylamino, amino and C3-8 cycloalkyl;
- and
- each C3-8 cycloalkenyl substituent is independently selected from the group consisting of halogen, hydroxyl, sulfonyl C1-8 alkyl, sulfoxide C1-8 alkyl, nitro, —OC1-6 alkyl, —SC1-6 alkyl, —C1-6 alkyl, ketone, alkylamino, amino, C6-10 aryl and C3-8 cycloalkyl;
- or an enantiomer, diastereomer or tautomer thereof;
- or a pharmaceutically acceptable salt of any of the foregoing.
32 more elements
Dependencies are inferred from the claim text.