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US 2002/0177595 A1Published application
Novel compounds useful as neuro-protective agents
AssigneeEli Lilly and Company
InventorsJill Ann Panetta, John Kevin Shadle, Lawrence Joseph Heinz, Michael LeRoy Phillips, John Robert Rizzo, Benjamin Alan Anderson, John Allan Rieck III, David Lee Varie
Life of this patent
Estimating the term…
Abstract
This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.
Claims21
A compound of the formula (III)
- 50
- Wherein:
- Ar is phenyl, pyridyl, tetrahydronaphthyl, benzofuranyl or chrornanyl substituted with zero to two substituents selected from the group consisting of —(C1-C6)alkyl, hydroxy and halo;
- and
- substituted with either:
- (i) one or two substituents selected from the group consisting of —O(CH2)tR6,
- 51
- And —(C1-C6 alkyl)R6;
- or
- (ii) two substituents which when taken together with the carbon atoms to which they are attached form a pyridyl or tetrahydropyridyl ring;
- provided that when substituent pattern (i) is present, the phenyl or pyridyl group of Ar may additionally be substituted with two substituents which when taken together with the carbon atoms to which they are attached form a phenyl ring;
- where R6 is —NR7R8, morpholin-1-yl, imidazol-1-yl, 4,5-dihydro-1H-imidazol-2-yl, thiomorpholin-1-yl, piperazin-1-yl or piperazin-1-yl substituted with —(C1-C4)alkyl or
- 52
- And R7 and R8 are each individually hydrogen, —(C1-C6)alkyl, —(CH2)pOH,
- 53
- —(CH2)p-piperidyl, —(CH2)pS(C1-C6)alkyl, —(CH2)pO(C1-C6)alkyl
- 54
- Where R9 is (C1-C6)alkyl;
- ---- represents a double or single bond;
- X is —O— or —S—;
- Y is —CR5′R5—, —O— or —S—, where R5′ is H and R5 is —H or —OH or R5 and R5′ taken together are ═O;
- Z is —CH2— or —N—;
- R is H or —(C1-C6)alkyl;
- R1 and R2 are each individually —(C1-C6)alkyl, —(C1-C6)alkoxy or phenyl;
- R3 is H or —(C1-C6)alkyl or R3 and R4 taken together form a phenyl group with the ring to which they are attached;
- R4 is hydrogen or —OH, or when Y is —CHR5, R4 and R5 are each individually H or when taken together form a bond;
- m is an integer from 0 to 2, both inclusive;
- q is 0 or 1;
- n is an integer from 0 to 4 both inclusive;
- p is an integer from 1 to 6 both inclusive;
- and
- t is an integer from 1 to 4 both inclusive;
- or a pharmaceutically acceptable salt, hydrate or optical isomer thereof.
30 more elements
A compound of the formula (II)
- 55
- Wherein:
- Ar is phenyl, pyridyl, or tetrahydronaphthyl substituted with zero to two substituents selected from the group consisting of —(C1-C6)alkyl, hydroxy and halo;
- and
- substituted with either:
- (i) one or two substituents selected from the group consisting of —O(CH2)tR6,
- 56
- And —(C1-C6 alkyl)R6;
- or
- (ii) two substituents which when taken together with the carbon atoms to which they are attached form a pyridyl or tetrahydropyridyl ring;
- provided that when substituent pattern (i) is present, the phenyl or pyridyl group of Ar nay additionally be substituted with two substituents which when taken together with the carbon atoms to which they are attached form a phenyl ring;
- where R6 is —NR7R8, morpholin-1-yl, imidazol-1-yl, 4,5-dihydro-1H-imidazol-2-yl, thiomorpholin-1-yl, piperazin-1-yl or piperazin-1-yl substituted with —(C1-C4)alkyl or
- 57
- And R7 and R8 are each individually hydrogen, —(C1-C6)alkyl, —(CH2)pOH, —(CH2)p-piperidyl, —(CH2)pS(C1-C6)alkyl or
- 58
- ---- represents a double or single bond;
- X is —O— or —S—;
- Y is —CHR5—, —O— or —S—;
- Z is —CH— or —N—;
- R is H or —(C1-C6)alkyl;
- R1 and R2 are each individually —(C1-C6)alkyl or —(C1-C6)alkoxy;
- R3 is H or —(C1-C6)alkyl, or R3 and R4 taken together form a phenyl group with the ring to which they are attached;
- R4 is hydrogen, or when Y is —CHR5, R4 and R5 are each individually H or when taken together form a bond;
- m is an integer from 0 to 2, both inclusive;
- a is 0 or 1;
- n is an integer from 0 to 4 both inclusive;
- p is an integer from 1 to 6 both inclusive;
- and
- t is an integer from 1 to 4 both inclusive;
- or a pharmaceutically acceptable salt, hydrate or optical isomer thereof.
27 more elements
A compound of the formula (I)
- 59
- Wherein
- Ar is phenyl or pyridyl substituted with zero to two substituents selected from the group consisting of —(C1-C6)alkyl, hydroxy and halo;
- and
- substituted with either:
- (i) one or two substituents selected from the group consisting of
- 60
- And —(C1-C6)alkyl R6;
- or
- (ii) two substituents which when taken together with the carbon atoms to which they are attached form a pyridyl or tetrahydropyridyl ring;
- provided that when substituent pattern (i) is present, the phenyl or pyridyl group of Ar may additionally be substituted with two substituents which when taken together with the carbon atoms to which they are attached form a phenyl ring;
- where R6 is —NR7R8, morpholin-1-yl, imidazol-1-yl, 4,5-dihydro-1H-imidazol-2-yl, thiomorpholin-1-yl, piperazin-1-yl or piperazin-1-yl substituted with —(C1-C4)alkyl or
- 61
- And R7 and R8 are each individually hydrogen, —C1-C6 alkyl, —(CH2)pOH or —(CH2)p-piperidyl;
- X is —O— or —S—;
- Y is —CHR5—, —O— or —S—;
- R is H or —(C1-C6)alkyl;
- R1 and R2 are each individually —(C1-C6)alkyl;
- R3 is H or —(C1-C6)alkyl;
- R4 is hydrogen, or when Y is —CHR5, R4 and R5 are each individually H or when taken together form a bond;
- m is 0 or 1;
- n is an integer from 0 to 4 both inclusive;
- and
- p is an integer from 1 to 6 both inclusive;
- or a pharmaceutically acceptable salt, hydrate or optical isomer thereof.
22 more elements
Dependencies are inferred from the claim text.