3-Phenyl-Pyrazole Derivatives as Modulators of the 5-Ht2A Serotonin Receptor Useful for the Treatment of Disorders Related Thereto
First Claim
Patent Images
1. A compound of Formula (Ia):
-
or a pharmaceutically acceptable salt, hydrate or solvate thereof;
wherein;
V is O, S, S(═
O), S(═
O)2 or NR10;
W is C1-4 alkylene optionally substituted with 1 to 8 substituents selected independently from the group consisting of C1-3 alkyl, C1-4 alkoxy, carboxy, cyano, C1-3 haloalkyl, halogen and oxo;
or W is absent;
X is C(═
O), C(═
S) or absent;
Y is O, NR11 or absent;
Z is C1-4 alkylene, or C3-6 cycloalkylene, each optionally substituted with 1 to 8 substituents selected independently from the group consisting of C1-3 alkyl, C1-4 alkoxy, carboxy, cyano, C1-3 haloalkyl, halogen, hydroxyl, and oxo;
or Z is absent;
R1 is selected from the group consisting of H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl and C3-7 cycloalkyl;
R2 is selected from the group consisting of H, C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, hydroxyl, thiol, nitro and sulfonamide;
R3 is selected from the group consisting of H, C2-6 alkenyl, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, halogen, heteroaryl and phenyl; and
wherein each of said C2-6 alkenyl, C1-6 alkyl, C2-6 alkynyl, C1-6 alkylsulfonamide, C3-7 cycloalkyl, heteroaryl and phenyl groups are optionally substituted with 1 to 5 substituents selected independently from the group consisting of C1-5 acyl, C1-5 acyloxy, C2-6 alkenyl, C1-4 alkoxy, C1-8 alkyl, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C2-6 alkynyl, C1-4 alkylsulfonamide, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C1-4 alkylthio, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, C2-6 dialkylcarboxamide, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, C1-4 haloalkylsulfinyl, C1-4 haloalkylsulfonyl, C1-4 haloalkylthio, hydroxyl, nitro and sulfonamide;
R4 is heterobicyclic, heterocyclic, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-12 acyloxy, C2-6 alkenyl, C1-4 alkoxy, C1-6 alkoxycarbonylamino, C1-6 alkyl, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C2-6 alkynyl, C1-4 alkylsulfonamide, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C1-4 alkylthio, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, C3-7 cycloalkylcarbonyl, C2-6 dialkylcarboxamide, formyl, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, C1-4 haloalkylsulfinyl, C1-4 haloalkylsulfonyl, C1-4 haloalkylthio, heteroaryl, hydroxyl, nitro, phenyl and sulfonamide;
wherein said C1-5 acyl, C1-5 acyloxy, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, amino, carbo-C1-6-alkoxy, and heteroaryl are each optionally substituted with substituents selected independently from the group consisting of C1-6 alkyl, C1-5 acyl, C1-4 alkoxy, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C1-4 alkylsulfonyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, hydroxyl, and phenyl;
R5, R6, and R7 are each selected independently from the group consisting of H, C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, C1-6 alkylimino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, heterocyclic, hydroxyl, thiol, nitro, phenoxy and phenyl;
R8 is C1-8 alkyl, C2-6 alkenyl, aryl, C3-7 cycloalkyl, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, C1-6 alkylimino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, heterocyclic, hydroxyl, thiol, nitro, phenoxy and phenyl, or two adjacent substituents together with said aryl or said heteroaryl form a C5-7 cycloalkyl optionally comprising 1 to 2 oxygen atoms and optionally substituted with F, Cl or Br; and
wherein said C2-6 alkenyl, C1-6 alkyl, C2-6 alkynyl, C1-6 alkylamino, C1-6 alkylimino, C2-8 dialkylamino, heterocyclic, and phenyl are each optionally substituted with 1 to 5 substituents selected independently from the group consisting of C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, hydroxyl, thiol and nitro; and
R9, R10, and R11 are each independently H or C1-8 alkyl;
provided that said compound is other than N-[4-oxiranylmethoxy-3-(2H-pyrazol-3-yl)-phenyl]-acetamide.
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Abstract
The present invention relates to certain 3-phenyl-pyrazole derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the 5-HT2A serotonin receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of platelet aggregation, coronary artery disease, myocardial infarction, transient ischemic attack, angina, stroke, atrial fibrillation, reducing the risk of blood clot formation, asthma or symptoms thereof, agitation or a symptom, behavioral disorders, drug induced psychosis, excitative psychosis, Gilles de la Tourette'"'"'s syndrome, manic disorder, organic or NOS psychosis, psychotic disorder, psychosis, acute schizophrenia, chronic schizophrenia, NOS schizophrenia and related disorders, and sleep disorders, sleep disorders, diabetic-related disorders, progressive multifocal leukoencephalopathy and the like. The present invention also relates to the methods for the treatment of 5-HT2A serotonin receptor mediated disorders in combination with other pharmaceutical agents administered separately or together.
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Citations
66 Claims
-
1. A compound of Formula (Ia):
-
or a pharmaceutically acceptable salt, hydrate or solvate thereof;
wherein;
V is O, S, S(═
O), S(═
O)2 or NR10;
W is C1-4 alkylene optionally substituted with 1 to 8 substituents selected independently from the group consisting of C1-3 alkyl, C1-4 alkoxy, carboxy, cyano, C1-3 haloalkyl, halogen and oxo;
or W is absent;
X is C(═
O), C(═
S) or absent;
Y is O, NR11 or absent;
Z is C1-4 alkylene, or C3-6 cycloalkylene, each optionally substituted with 1 to 8 substituents selected independently from the group consisting of C1-3 alkyl, C1-4 alkoxy, carboxy, cyano, C1-3 haloalkyl, halogen, hydroxyl, and oxo;
or Z is absent;
R1 is selected from the group consisting of H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl and C3-7 cycloalkyl;
R2 is selected from the group consisting of H, C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, hydroxyl, thiol, nitro and sulfonamide;
R3 is selected from the group consisting of H, C2-6 alkenyl, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, halogen, heteroaryl and phenyl; and
wherein each of said C2-6 alkenyl, C1-6 alkyl, C2-6 alkynyl, C1-6 alkylsulfonamide, C3-7 cycloalkyl, heteroaryl and phenyl groups are optionally substituted with 1 to 5 substituents selected independently from the group consisting of C1-5 acyl, C1-5 acyloxy, C2-6 alkenyl, C1-4 alkoxy, C1-8 alkyl, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C2-6 alkynyl, C1-4 alkylsulfonamide, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C1-4 alkylthio, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, C2-6 dialkylcarboxamide, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, C1-4 haloalkylsulfinyl, C1-4 haloalkylsulfonyl, C1-4 haloalkylthio, hydroxyl, nitro and sulfonamide;
R4 is heterobicyclic, heterocyclic, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-12 acyloxy, C2-6 alkenyl, C1-4 alkoxy, C1-6 alkoxycarbonylamino, C1-6 alkyl, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C2-6 alkynyl, C1-4 alkylsulfonamide, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C1-4 alkylthio, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, C3-7 cycloalkylcarbonyl, C2-6 dialkylcarboxamide, formyl, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, C1-4 haloalkylsulfinyl, C1-4 haloalkylsulfonyl, C1-4 haloalkylthio, heteroaryl, hydroxyl, nitro, phenyl and sulfonamide;
wherein said C1-5 acyl, C1-5 acyloxy, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, amino, carbo-C1-6-alkoxy, and heteroaryl are each optionally substituted with substituents selected independently from the group consisting of C1-6 alkyl, C1-5 acyl, C1-4 alkoxy, C1-6 alkylamino, C2-8 dialkylamino, C1-4 alkylcarboxamide, C1-4 alkylsulfonyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-6 cycloalkyl, halogen, C1-4 haloalkoxy, C1-4 haloalkyl, hydroxyl, and phenyl;
R5, R6, and R7 are each selected independently from the group consisting of H, C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, C1-6 alkylimino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, heterocyclic, hydroxyl, thiol, nitro, phenoxy and phenyl;
R8 is C1-8 alkyl, C2-6 alkenyl, aryl, C3-7 cycloalkyl, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, C1-6 alkylimino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, C2-8 dialkylsulfonamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, heterocyclic, hydroxyl, thiol, nitro, phenoxy and phenyl, or two adjacent substituents together with said aryl or said heteroaryl form a C5-7 cycloalkyl optionally comprising 1 to 2 oxygen atoms and optionally substituted with F, Cl or Br; and
wherein said C2-6 alkenyl, C1-6 alkyl, C2-6 alkynyl, C1-6 alkylamino, C1-6 alkylimino, C2-8 dialkylamino, heterocyclic, and phenyl are each optionally substituted with 1 to 5 substituents selected independently from the group consisting of C1-6 acyl, C1-6 acyloxy, C2-6 alkenyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylcarboxamide, C2-6 alkynyl, C1-6 alkylsulfonamide, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylthio, C1-6 alkylureyl, amino, C1-6 alkylamino, C2-8 dialkylamino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, C2-8 dialkylcarboxamide, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C1-6 haloalkylthio, hydroxyl, thiol and nitro; and
R9, R10, and R11 are each independently H or C1-8 alkyl;
provided that said compound is other than N-[4-oxiranylmethoxy-3-(2H-pyrazol-3-yl)-phenyl]-acetamide. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 66)
-
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3. The compound according to claim 1, wherein V is O.
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4. The compound according to claim 1 wherein W is —
- CH2—
, —
CH2CH2—
, —
CH2C(═
O)—
, —
CH2CH2CH2—
, —
C(CH3)2C(═
O)—
, —
CH2CH(CH3)—
, —
CH(CH3)CH2—
, —
C(CH3)2CH2—
, or —
CH2C(CH3)2—
.
- CH2—
-
5. The compound according to claim 1, wherein W is absent.
-
6. The compound according to claim 1, wherein X is C(═
- O).
-
7. The compound according to claim 1, wherein X is absent.
-
8. The compound according to claim 1, wherein Y is NH, O or absent.
-
9. The compound according to claim 1, wherein Z is absent, —
- CH2—
, —
CH(OH)—
, —
CF2—
, —
C(CH3)2—
, 1,1-cyclopropyl, —
CH2CH2—
, —
CH2CH2CH2—
, —
CH(CH3)—
, or —
C(═
O)—
.
- CH2—
-
10. The compound according to claim 1, wherein R1 is —
- CH3.
-
11. The compound according to claim 1, wherein R2 is H.
-
12. The compound according to claim 1, wherein R3 is H, F, Cl or Br.
-
13. The compound according to claim 1, wherein R4 is heterobicyclic, heterocyclic, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-12 acyloxy, C1-6 alkoxycarbonylamino, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, C1-4 alkylsulfonamide, C1-4 alkylsulfonyl, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, C2-6 dialkylcarboxamide, formyl, halogen, C1-4 haloalkyl, heteroaryl, hydroxyl and phenyl;
- wherein said C1-5 acyl, C1-5 acyloxy, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, amino, carbo-C1-6-alkoxy and heteroaryl are each optionally substituted with substituents selected independently from the group consisting of C1-6 alkyl, carbo-C1-6-alkoxy, carboxy, and phenyl.
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14. The compound according to claim 1, wherein R4 is selected from the group consisting of pyrrolidin-1-yl, pyrrolidin-2-yl, piperidin-1-yl, piperidin-4-yl, piperidin-3-yl, morpholin-4-yl, piperazin-1-yl, pyridin-3-yl, pyridin-2-yl, pyridin-4-yl, azetidin-1-yl, thiomorpholin-4-yl, morpholin-2-yl, 2,5-diaza-bicyclo[2.2.1]hept-2-yl, [1,4]oxazepan-4-yl, 1,1-dioxo-1λ
-
6-thiomorpholin-4-yl, piperidin-2-yl, azepan-1-yl, pyrrolidin-3-yl, 3-oxo-piperazin-1-yl, 7-aza-bicyclo[2.2.1]hept-7-yl, and imidazol-1-yl each optionally substituted with substituents selected independently from the group consisting of CH3, C(═
O)O-t-butyl, C(═
O)OH, C(═
O)OEt, NHC(═
O)O-t-butyl, OH, C(═
O)NHCH2C(═
O)OCH3, NHC(═
O)CH2C(═
O)OCH3, C(═
O)NHCH2C(═
O)OH, NHC(═
O)CH2C(═
O)OH, C(═
O)OCH3, OC(═
O)CH2CH2C(═
O)OCH3, OC(═
O)CH2CH2CH2CH2CH3, CH2C(═
O)OCH2CH3, OCH3, CH2C(═
O)OH, OC(═
O)CH2CH2C(═
O)OCH3, CH2CH2C(═
O)OCH3, C(═
O)CH3, and C(═
O)OCH2-phenyl, C(═
O)CH2CH2C(═
O)OCH3, C(═
O)CH2CH2C(═
O)OH, F, phenyl, CH2C(═
O)OCH3, S(═
O)2CH3, OCH2-phenyl, CH2-phenyl, C(═
O)NH2, CHO, —
NH2, NHC(═
O)CH3, C(═
O)N(CH3)2, NHS(═
O)2CH3, —
CF3, 3-methyl-[1,2,4]oxadiazol-5-yl, and CH(CH3)2.
-
6-thiomorpholin-4-yl, piperidin-2-yl, azepan-1-yl, pyrrolidin-3-yl, 3-oxo-piperazin-1-yl, 7-aza-bicyclo[2.2.1]hept-7-yl, and imidazol-1-yl each optionally substituted with substituents selected independently from the group consisting of CH3, C(═
-
15. The compound according to claim 1, wherein R5, R6 and R7 are all H.
-
16. The compound according to claim 1, wherein R8 is C1-8 alkyl, C2-6 alkenyl, aryl, C3-7 cycloalkyl, or heteroaryl each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-6 alkoxy, C1-6 alkyl, cyano, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, and hydroxyl, or two adjacent substituents together with said aryl or said heteroaryl form a C5-7 cycloalkyl optionally comprising 1 to 2 oxygen atoms and optionally substituted with F.
-
17. The compound according to claim 1, wherein R8 is selected from the group consisting of methyl, iso-propyl, iso-butyl, n-propyl, n-butyl, 2-methyl-propenyl, phenyl, naphthalen-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, pyridin-2-yl, pyridin-3-yl, 1H-benzoimidazol-2-yl, benzooxazol-2-yl, benzothiazol-2-yl, thiophen-2-yl, furan-2-yl, benzothiophen-2-yl, thiazol-2-yl, isoxazol-3-yl, and pyridin-4-yl each optionally substituted with substituents selected independently from the group consisting of C(═
- O)CH3, OCH3, CH3, F, Cl, Br, CF3, hydroxyl, OCF3, and CN, or two adjacent substituents together with said phenyl form a C5 cycloalkyl comprising 2 oxygen atoms and optionally substituted with F.
-
18. The compound according to claim 1, wherein R8 is selected from the group consisting of 4-chloro-phenyl, 2,4-difluoro-phenyl, 4-fluoro-phenyl, 3-chloro-phenyl, 2,2-difluoro-benzo[1,3]dioxol-5-yl, 4-hydroxy-phenyl, 4-chloro-2-hydroxy-phenyl, phenyl, 3-fluoro-phenyl, 2-fluoro-phenyl, 2-chloro-phenyl, 4-bromo-phenyl, 4-methoxy-phenyl, 4-trifluoromethyl-phenyl, 3,5-bis-trifluoromethyl-phenyl, 2-fluoro-5-methyl-phenyl, 3-methoxy-phenyl, 3-acetyl-phenyl, 4-methyl-phenyl, 3-trifluoromethyl-phenyl, 3,5-difluoro-phenyl, 2,4-dichloro-phenyl, 4-chloro-2-trifluoromethyl-phenyl, 3,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, naphthalen-1-yl, 4-trifluoromethoxy-phenyl, 3-cyano-phenyl, 2-trifluoromethoxy-phenyl, 4-chloro-2-fluoro-phenyl, 2,3-difluoro-phenyl, 2,4,5-trifluoro-phenyl, 2,3,4-trifluoro-phenyl, 3,4-dichloro-phenyl, 4-fluoro-3-trifluoromethyl-phenyl, 5-fluoro-2-trifluoromethyl-phenyl, 2-trifluoromethyl-phenyl, 3-methyl-phenyl, 2-fluoro-4-trifluoromethyl-phenyl, 4-chloro-3-fluoro-phenyl, 3-fluoro-4-methyl-phenyl, 4-fluoro-3-methyl-phenyl, 3-fluoro-4-trifluoromethyl-phenyl, 3-chloro-4-fluoro-phenyl, 2,6-dichloro-phenyl, 4-cyano-phenyl, 2,5-dichloro-phenyl, and benzo[1,3]dioxol-5-yl.
-
19. The compound according to claim 1, wherein R8 is selected from the group consisting of methyl, iso-propyl, iso-butyl, n-propyl, n-butyl, 2-methyl-propenyl, 3-methyl-butyl, cyclopropyl, cyclobutyl, and cyclopentyl.
-
20. The compound according to claim 1, wherein R8 is selected from the group consisting of pyridin-3-yl, 6-trifluoromethyl-pyridin-3-yl, 3-hydroxy-pyridin-2-yl, 6-methyl-pyridin-3-yl, 6-hydroxy-pyridin-3-yl, 1H-benzoimidazol-2-yl, benzooxazol-2-yl, benzothiazol-2-yl, thiophen-2-yl, furan-2-yl, 5-chloro-thiophen-2-yl, benzothiophen-2-yl, thiazol-2-yl, 5-methyl-isoxazol-3-yl, and pyridin-4-yl.
-
21. The compound according to claim 1, wherein R9 is H.
-
22. The compound according to claim 1, wherein R11 is H.
-
23. The compound according to claim 1 having Formula (Ik):
or a pharmaceutically acceptable salt, hydrate or solvate thereof;
wherein;
W is —
CH2—
, —
CH2CH2—
, —
CH2C(═
O)—
, —
CH2CH2CH2—
, —
C(CH3)2C(═
O)—
, —
CH2CH(CH3)—
, —
CH(CH3)CH2—
, —
C(CH3)2CH2—
, or —
CH2C(CH3)2—
;
or W is absent;
X is C(═
O) or absent;
Y is NH, O or absent;
Z is absent, —
CH2—
, —
CH(OH)—
, —
CF2—
, —
C(CH3)2—
, 1,1-cyclopropyl, —
CH2CH2—
, —
CH2CH2CH2—
, —
CH(CH3)—
, or —
C(═
O)—
;
R1 is C1-6 alkyl;
R3 is H or halogen;
R4 is heterobicyclic, heterocyclic, or heteroaryl, each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-12 acyloxy, C1-4 alkoxy, C1-6 alkoxycarbonylamino, C1-6 alkyl, C1-4 alkylcarboxamide, C1-4 alkylsulfonamide, C1-4 alkylsulfonyl, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, C2-6 dialkylcarboxamide, formyl, halogen, C1-4 haloalkyl, heteroaryl, hydroxyl and phenyl;
wherein said C1-5 acyl, C1-5 acyloxy, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, amino, carbo-C1-6-alkoxy and heteroaryl are each optionally substituted with substituents selected independently from the group consisting of C1-6 alkyl, carbo-C1-6-alkoxy, carboxy, and phenyl; and
R8 is C1-8 alkyl, C2-6 alkenyl, aryl, C3-7 cycloalkyl, or heteroaryl, each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-6 alkoxy, C1-6 alkyl, C1-6 alkylsulfonyl, amino, C1-6 alkylamino, C2-8 dialkylamino, C1-6 alkylimino, carbo-C1-6-alkoxy, carboxamide, carboxy, cyano, C3-7 cycloalkyl, halogen, C1-6 haloalkoxy, C1-6 haloalkyl, heterocyclic, hydroxyl, nitro, and phenyl, or two adjacent substituents together with said aryl or said heteroaryl form a C5-7 cycloalkyl optionally comprising 1 to 2 oxygen atoms and optionally substituted with F.
-
24. The compound according to claim 1 having Formula (Ik):
or a pharmaceutically acceptable salt, hydrate or solvate thereof;
wherein;
W is —
CH2—
, —
CH2CH2—
, —
CH2C(═
O)—
, —
CH2CH2CH2—
, —
C(CH3)2C(═
O)—
, —
CH2CH(CH3)—
, —
CH(CH3)CH2—
, —
C(CH3)2CH2—
, or —
CH2C(CH3)2—
;
or W is absent;
X is C(═
O) or absent;
Y is NH, O or absent;
Z is absent, —
CH2—
, —
CH(OH)—
, —
CF2—
, —
C(CH3)2—
, 1,1-cyclopropyl, —
CH2CH2—
, —
CH2CH2CH2—
, —
CH(CH3)—
, or —
C(═
O)—
;
R1 is C1-6 alkyl;
R3 is H or halogen;
R4 is heterobicyclic, heterocyclic, or heteroaryl, each optionally substituted with substituents selected independently from the group consisting of C1-6 acyl, C1-12 acyloxy, C1-4 alkoxy, C1-6 alkoxycarbonylamino, C1-6 alkyl, C1-4 alkylcarboxamide, C1-4 alkylsulfonamide, C1-4 alkylsulfonyl, C1-4 alkylureyl, amino, carbo-C1-6-alkoxy, carboxamide, carboxy, C2-6 dialkylcarboxamide, formyl, halogen, C1-4 haloalkyl, heteroaryl, hydroxyl and phenyl;
wherein said C1-5 acyl, C1-5 acyloxy, C1-4 alkoxy, C1-6 alkyl, C1-4 alkylcarboxamide, amino, carbo-C1-6-alkoxy and heteroaryl are each optionally substituted with substituents selected independently from the group consisting of C1-6 alkyl, carbo-C1-6-alkoxy, carboxy, and phenyl; and
R8 is selected from the group consisting of 4-chloro-phenyl, 2,4-difluoro-phenyl, 4-fluoro-phenyl, 3-chloro-phenyl, 2,2-difluoro-benzo[1,3]dioxol-5-yl, 4-hydroxy-phenyl, 4-chloro-2-hydroxy-phenyl, phenyl, 3-fluoro-phenyl, 2-fluoro-phenyl, 2-chloro-phenyl, 4-bromo-phenyl, 4-methoxy-phenyl, 4-trifluoromethyl-phenyl, 3,5-bis-trifluoromethyl-phenyl, 2-fluoro-5-methyl-phenyl, 3-methoxy-phenyl, 3-acetyl-phenyl, 4-methyl-phenyl, 3-trifluoromethyl-phenyl, 3,5-difluoro-phenyl, 2,4-dichloro-phenyl, 4-chloro-2-trifluoromethyl-phenyl, 3,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, naphthalen-1-yl, 4-trifluoromethoxy-phenyl, 3-cyano-phenyl, 2-trifluoromethoxy-phenyl, 4-chloro-2-fluoro-phenyl, 2,3-difluoro-phenyl, 2,4,5-trifluoro-phenyl, 2,3,4-trifluoro-phenyl, 3,4-dichloro-phenyl, 4-fluoro-3-trifluoromethyl-phenyl, 5-fluoro-2-trifluoromethyl-phenyl, 2-trifluoromethyl-phenyl, 3-methyl-phenyl, 2-fluoro-4-trifluoromethyl-phenyl, 4-chloro-3-fluoro-phenyl, 3-fluoro-4-methyl-phenyl, 4-fluoro-3-methyl-phenyl, 3-fluoro-4-trifluoromethyl-phenyl, 3-chloro-4-fluoro-phenyl, 2,6-dichloro-phenyl, 4-cyano-phenyl, 2,5-dichloro-phenyl, and benzo[1,3]dioxol-5-yl.
-
25. The compound according to claim 1 having Formula (Io):
or a pharmaceutically acceptable salt, hydrate or solvate thereof;
wherein;
W is —
CH2—
, —
CH2CH2—
or —
CH2C(═
O)—
;
R1 is C1-6 alkyl;
R3 is H or halogen;
R4 is pyrrolidin-1-yl, pyrrolidin-2-yl, piperidin-1-yl, piperidin-4-yl, piperidin-3-yl, morpholin-4-yl, piperazin-1-yl, pyridin-3-yl, pyridin-2-yl or pyridin-4-yl, each optionally substituted with substituents selected independently from the group consisting of CH3, C(═
O)O-t-butyl, C(═
O)OH, C(═
O)OEt, NHC(═
O)O-t-butyl, OH, C(═
O)NHCH2C(═
O)OCH3, NHC(═
O)CH2C(═
O)OCH3, C(═
O)NHCH2C(═
O)OH, NHC(═
O)CH2C(═
O)OH, C(═
O)OCH3, OC(═
O)CH2CH2C(═
O)OCH3, OC(═
O)CH2CH2CH2CH2CH3, CH2C(═
O)OCH2CH3, OCH3, CH2C(═
O)OH, OC(═
O)CH2CH2C(═
O)OCH3, CH2CH2C(═
O)OCH3, C(═
O)CH3, and C(═
O)OCH2-phenyl; and
R8 is selected from the group consisting of 1H-benzoimidazol-2-yl, benzooxazol-2-yl and benzothiazol-2-yl.
-
26. The compound according to claim 1, wherein the compound is selected from the group consisting of:
-
1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-(4-chloro-phenyl)-urea (Compound
1);
N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-(2-morpholinoethoxy)phenyl)cyclopropanecarboxamide (Compound
271);
N-{3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-[2-(4-methoxy-piperidin-1-yl)-ethoxy]-phenyl}-3-fluoro-benzamide (Compound
637);
N-[3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-fluoro-4-methyl-benzamide (Compound
559);
1-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-(2-morpholinoethoxy)phenyl)-3-(3-chlorophenyl)urea (Compound
231);
1-(4-Chloro-benzyl)-3-[3-(2-methyl-2H-pyrazol-3-yl)-4-(3-morpholin-4-yl-propoxy)-phenyl]-urea (Compound
666);
3-Chloro-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzamide (Compound
512);
3-Fluoro-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzamide (Compound
487);
1-{3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-[2-(3-hydroxy-azetidin-1-yl)-ethoxy]-phenyl}-3-(4-chloro-phenyl)-urea (Compound
298);
1-[4-[2-(7-Aza-bicyclo[2.2.1]hept-7-yl)-ethoxy]-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-(3-trifluoromethyl-benzyl)-urea (Compound
710);
1-[4-[2-(7-Aza-bicyclo[2.2.1]hept-7-yl)-ethoxy]-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-(2,4-difluoro-benzyl)-urea (Compound
734);
4-Fluoro-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-benzamide (Compound
281);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzamide (Compound
282);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide (Compound
435);
N-[4-[2-(3,3-Difluoro-pyrrolidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-4-fluoro-3-methyl-benzamide (Compound
546);
4-Fluoro-3-methyl-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(1-methyl-pyrrolidin-2-ylmethoxy)-phenyl]-benzamide (Compound
547);
N-{3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-[2-(2-methyl-pyrrolidin-1-yl)-ethoxy]-phenyl}-3,4-difluoro-benzamide (Compound
579);
N-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(1-methyl-pyrrolidin-3-yloxy)-phenyl]-3,4-difluoro-benzamide (Compound
585);
N-[4-[2-(3-Hydroxy-pyrrolidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-4-trifluoromethyl-benzamide (Compound
586);
3-Fluoro-N-[4-[2-(4-formyl-piperazin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-benzamide (Compound
752);
N-[4-[2-(4-Acetyl-piperazin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-methoxy-benzamide (Compound
755);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-phenyl-acetamide) (Compound
762);
2-(3-Fluoro-phenyl)-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide (Compound
766);
2-(3-Chloro-phenyl)-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide (Compound
767);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-(3-trifluoromethyl-phenyl)-acetamide (Compound
768);
2-(3-Methoxy-phenyl)-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide (Compound
769);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-m-tolyl-acetamide (Compound
770);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-p-tolyl-acetamide (Compound
771);
2-Benzo[1,3]dioxol-5-yl-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide (Compound
772);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide (Compound
794);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-thiophen-2-yl-acetamide (Compound
795);
1-[4-(2-Azetidin-1-yl-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-(2,4-difluoro-phenyl)-urea (Compound
86);
1-{3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)4-[2-(3-methoxy-azetidin-1-yl)-ethoxy]-phenyl}-3-(4-chloro-phenyl)-urea (Compound
267);
N-{3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-[2-(3-methoxy-azetidin-1-yl)-ethoxy]-phenyl}-3-methyl-butyramide (Compound
326);
Benzooxazol-2-yl-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-amine (Compound
199);
5-Chloro-thiophene-2-carboxylic acid [3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-amide (Compound
333);
3,4-Difluoro-N-[4-[2-(2-methyl-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-benzamide (Compound
459);
N-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(1-methyl-piperidin-4-yloxy)-phenyl]-4-fluoro-3-methyl-benzamide (Compound
745);
1-(2-Fluoro-phenyl)-3-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-urea (Compound
65);
N-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-fluoro-benzamide (Compound
455);
Cyclopentanecarboxylic acid [3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-amide (Compound
310);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzamide (Compound
343);
N-{3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-[2-(3-fluoro-pyrrolidin-1-yl)-ethoxy]-phenyl}-3-fluoro-benzamide (Compound
475);
3-Chloro-4-fluoro-N-[4-[2-(4-fluoro-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-benzamide (Compound
538);
N-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(piperidin-3-yloxy)-phenyl]-4-fluoro-benzamide (Compound
396);
N-[4-[2-(4-Acetyl-piperazin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-fluoro-benzamide (Compound
660);
N-[4-[2-(4,4-Difluoro-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-fluoro-benzamide (Compound
778);
3-Fluoro-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-benzamide (Compound
729);
3-Methoxy-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-benzamide (Compound
733);
1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-(2,4-difluoro-phenyl)-urea (Compound
5);
1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-pyridin-4-yl-ethoxy)-phenyl]-3-(4-chloro-phenyl)-urea (Compound
145);
1-(2,4-Difluoro-phenyl)-3-[4-(2-imidazol-1-yl-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea (Compound
219);
[4-(2-Azepan-1-yl-ethoxy)-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-phenyl]-carbamic acid isopropyl ester (Compound
352);
N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide (Compound
568);
N-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-3-fluoro-4-trifluoromethyl-benzamide (Compound
606);
[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-thiomorpholin-4-yl-ethoxy)-phenyl]-carbamic acid isopropyl ester (Compound
214);
[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-carbamic acid isopropyl ester (Compound
215); and
N-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide (Compound
527);
or a pharmaceutically acceptable salt, hydrate or solvate thereof.
-
-
27. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.
-
28. A method for treating a 5-HT2A mediated disorder in an individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
29. The method according to claim 28, wherein said 5-HT2A mediated disorder is selected from the group consisting of coronary artery disease, myocardial infarction, transient ischemic attack, angina, stroke, and atrial fibrillation.
-
30. A method for treating a condition associated with platelet aggregation in an individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
31. A method for reducing the risk of blood clot formation in an angioplasty or coronary bypass surgery individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
32. A method for reducing the risk of blood clot formation in an individual suffering from atrial fibrillation, comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
33. A method for treating a sleep disorder in an individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
34. The method according to claim 33, wherein said sleep disorder is a dyssomnia.
-
35. The method according to claim 33, wherein said sleep disorder is a parasomnia.
-
36. A method for treating a diabetic-related disorder in an individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
37. A method for treating progressive multifocal leukoencephalopathy in an individual comprising administering to said individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
38. A method for treating hypertension in an individual comprising administering to the individual in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutical composition according to claim 27.
-
66. A process for preparing a composition comprising admixing a compound according to claim 1 and a pharmaceutically acceptable carrier.
-
39-65. -65. (canceled)
Specification
-
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Current AssigneeArena Pharmaceuticals Incorporated (Pfizer Inc.)
-
Original AssigneeArena Pharmaceuticals Incorporated (Pfizer Inc.)
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InventorsJones, Robert, Feichtinger, Konrad, Teegarden, Bradley, Casper, Martin, Xiong, Yifeng, Strah-Pleynet, Sonja, Jayakumar, Honnappa, Lehmann, Juerg, Dosa, Peter, Karoline Choi, Jin, Unett, David
-
Application NumberUS11/597,306Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/210.200CPC Class CodesA61K 31/5377 not condensed and containin...A61P 11/06 AntiasthmaticsA61P 25/00 Drugs for disorders of the ...A61P 25/18 Antipsychotics, i.e. neurol...A61P 25/20 Hypnotics; SedativesA61P 25/28 for treating neurodegenerat...A61P 29/00 Non-central analgesic, anti...A61P 3/00 Drugs for disorders of the ...A61P 3/10 for hyperglycaemia, e.g. an...A61P 43/00 Drugs for specific purposes...A61P 7/02 Antithrombotic agents; Anti...A61P 9/00 Drugs for disorders of the ...A61P 9/10 for treating ischaemic or a...A61P 9/12 AntihypertensivesC07D 231/12 with only hydrogen atoms, h...C07D 231/16 Halogen atoms or nitro radi...C07D 401/12 linked by a chain containin...C07D 403/12 linked by a chain containin...C07D 405/12 linked by a chain containin...C07D 409/12 linked by a chain containin...View All
