CA2542514A1

CA2542514A1 - Composes de pyrimidine utiles pour le traitement des inflammations

Composes de pyrimidine utiles pour le traitement des inflammations Download PDF

Info

Publication number: CA2542514A1
Authority: CA; Canada
Prior art keywords: group; alkyl; amino; methyl; heteroaryl
Prior art date: 2003-10-23
Legal status : Abandoned

Application number

CA002542514A

Other languages

English (en)

Inventor

Michael Clare

Timothy J. Hagen

Stephen C. Houdek

Patrick J. Lennon

Richard M. Weier

Xiangdong Xu

Current Assignee

Pharmacia LLC

Original Assignee

Individual

Priority date

2003-10-23

Filing date

2004-10-11

Publication date

2005-05-06

2004-10-11 Application filed by Individual filed Critical Individual

2005-05-06 Publication of CA2542514A1 publication Critical patent/CA2542514A1/fr

Status Abandoned legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims description 25
206010061218 Inflammation Diseases 0.000 title claims description 14
230000004054 inflammatory process Effects 0.000 title claims description 13
150000003230 pyrimidines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 80
-1 cyano, hydroxyl Chemical group 0.000 claims description 2069
125000001072 heteroaryl group Chemical group 0.000 claims description 180
125000000217 alkyl group Chemical group 0.000 claims description 153
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 146
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 146
125000003118 aryl group Chemical group 0.000 claims description 127
125000004103 aminoalkyl group Chemical group 0.000 claims description 96
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 96
125000001188 haloalkyl group Chemical group 0.000 claims description 92
125000001145 hydrido group Chemical group *[H] 0.000 claims description 84
125000001424 substituent group Chemical group 0.000 claims description 78
125000002541 furyl group Chemical group 0.000 claims description 76
125000001041 indolyl group Chemical group 0.000 claims description 76
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 76
125000000842 isoxazolyl group Chemical group 0.000 claims description 76
125000002971 oxazolyl group Chemical group 0.000 claims description 76
125000003226 pyrazolyl group Chemical group 0.000 claims description 76
125000004076 pyridyl group Chemical group 0.000 claims description 76
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 76
125000001544 thienyl group Chemical group 0.000 claims description 76
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 75
125000002883 imidazolyl group Chemical group 0.000 claims description 75
125000000168 pyrrolyl group Chemical group 0.000 claims description 75
125000003710 aryl alkyl group Chemical group 0.000 claims description 70
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 69
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 62
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 62
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 62
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 60
125000003342 alkenyl group Chemical group 0.000 claims description 59
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 58
125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 58
125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 58
125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 58
125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 58
125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 58
125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 58
125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 58
125000002632 imidazolidinyl group Chemical group 0.000 claims description 58
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 58
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 58
125000003965 isoxazolidinyl group Chemical group 0.000 claims description 58
125000000160 oxazolidinyl group Chemical group 0.000 claims description 58
125000003386 piperidinyl group Chemical group 0.000 claims description 58
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 58
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 58
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
125000005843 halogen group Chemical group 0.000 claims description 50
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 48
239000004305 biphenyl Chemical group 0.000 claims description 48
235000010290 biphenyl Nutrition 0.000 claims description 48
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 48
125000001624 naphthyl group Chemical group 0.000 claims description 48
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 46
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 46
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 46
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 46
125000003545 alkoxy group Chemical group 0.000 claims description 43
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 40
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 40
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 40
125000004475 heteroaralkyl group Chemical group 0.000 claims description 40
125000002252 acyl group Chemical group 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000000304 alkynyl group Chemical group 0.000 claims description 36
125000004438 haloalkoxy group Chemical group 0.000 claims description 35
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 32
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 30
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 30
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 30
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 30
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 29
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
RLSPDWOUWUFUJW-UHFFFAOYSA-N [azido-nitro-(2-phenoxyphenyl)methoxy] thiocyanate Chemical group O(C1=CC=CC=C1)C1=C(C(OSC#N)(N=[N+]=[N-])[N+](=O)[O-])C=CC=C1 RLSPDWOUWUFUJW-UHFFFAOYSA-N 0.000 claims description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 28
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 28
150000002540 isothiocyanates Chemical group 0.000 claims description 28
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 28
125000006235 propyl amino ethyl group Chemical group [H]N(C([H])([H])C([H])([H])*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 25
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 24
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
125000005842 heteroatom Chemical group 0.000 claims description 24
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 23
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 21
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 20
125000006319 alkynyl amino group Chemical group 0.000 claims description 20
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 20
125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 20
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 20
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 20
125000005981 pentynyl group Chemical group 0.000 claims description 20
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 20
125000004423 acyloxy group Chemical group 0.000 claims description 18
125000006323 alkenyl amino group Chemical group 0.000 claims description 18
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
125000004001 thioalkyl group Chemical group 0.000 claims description 18
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 16
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 16
125000006226 butoxyethyl group Chemical group 0.000 claims description 16
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 16
125000006301 indolyl methyl group Chemical group 0.000 claims description 16
125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 16
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 16
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
150000003254 radicals Chemical group 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
125000006251 butylcarbonyl group Chemical group 0.000 claims description 12
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 12
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 12
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 12
125000004871 hexylcarbonyl group Chemical group C(CCCCC)C(=O)* 0.000 claims description 12
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 claims description 12
125000004673 propylcarbonyl group Chemical group 0.000 claims description 12
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 12
125000006513 pyridinyl methyl group Chemical group 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004442 acylamino group Chemical group 0.000 claims description 10
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000004862 thiobutyl group Chemical group 0.000 claims description 8
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 8
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 8
125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
208000035475 disorder Diseases 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
208000002193 Pain Diseases 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
206010003246 arthritis Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
QYNRQBHRUULQPT-UHFFFAOYSA-N 4-amino-2-(2,6-dihydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1c(O)cccc1O QYNRQBHRUULQPT-UHFFFAOYSA-N 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
208000036119 Frailty Diseases 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
206010003549 asthenia Diseases 0.000 claims description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 28
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 22
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 15
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 12
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 8
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 6
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 5
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
UBEGZTZJMWAWIW-UHFFFAOYSA-N 4-amino-2-(2,5-dihydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1cc(O)ccc1O UBEGZTZJMWAWIW-UHFFFAOYSA-N 0.000 claims 2
APNSKVZNFKCFKR-UHFFFAOYSA-N 4-amino-2-(2-fluoro-6-hydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1c(O)cccc1F APNSKVZNFKCFKR-UHFFFAOYSA-N 0.000 claims 2
SRATZOYXQZGLEO-UHFFFAOYSA-N 4-amino-2-(2-hydroxy-6-methoxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.COc1cccc(O)c1-c1nc(N)c(C#N)c(n1)C1CCCNC1 SRATZOYXQZGLEO-UHFFFAOYSA-N 0.000 claims 2
SWXKUGDMMNTTLE-UHFFFAOYSA-N 4-amino-2-(2-hydroxy-6-propylphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile Chemical compound CCCc1cccc(O)c1-c1nc(N)c(C#N)c(n1)C1CCCNC1 SWXKUGDMMNTTLE-UHFFFAOYSA-N 0.000 claims 2
VFPXYBXIXQGDPY-UHFFFAOYSA-N 4-amino-2-(2-hydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1ccccc1O VFPXYBXIXQGDPY-UHFFFAOYSA-N 0.000 claims 2
JMYOTFJMKLKKNV-UHFFFAOYSA-N 4-amino-2-(3,5-dichloro-2,6-dihydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1c(O)c(Cl)cc(Cl)c1O JMYOTFJMKLKKNV-UHFFFAOYSA-N 0.000 claims 2
OEWITCKTZSRMGX-UHFFFAOYSA-N 4-amino-2-(5-bromo-2-hydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile Chemical compound Nc1nc(nc(C2CCCNC2)c1C#N)-c1cc(Br)ccc1O OEWITCKTZSRMGX-UHFFFAOYSA-N 0.000 claims 2
GNSZAYWAIPNJEY-UHFFFAOYSA-N 4-amino-2-(5-chloro-2-hydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile Chemical compound Nc1nc(nc(C2CCCNC2)c1C#N)-c1cc(Cl)ccc1O GNSZAYWAIPNJEY-UHFFFAOYSA-N 0.000 claims 2
WCYOMRHNOWQUTM-UHFFFAOYSA-N 4-amino-2-(5-chloro-2-hydroxyphenyl)-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1cc(Cl)ccc1O WCYOMRHNOWQUTM-UHFFFAOYSA-N 0.000 claims 2
AVRJYELKTHYSST-UHFFFAOYSA-N 4-amino-2-[2-hydroxy-5-(trifluoromethyl)phenyl]-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1cc(ccc1O)C(F)(F)F AVRJYELKTHYSST-UHFFFAOYSA-N 0.000 claims 2
KVMUWAGBZKXSIL-UHFFFAOYSA-N 4-amino-2-[2-hydroxy-6-(3-methylbutyl)phenyl]-6-piperidin-3-ylpyrimidine-5-carbonitrile Chemical compound CC(C)CCc1cccc(O)c1-c1nc(N)c(C#N)c(n1)C1CCCNC1 KVMUWAGBZKXSIL-UHFFFAOYSA-N 0.000 claims 2
CCBBYZHOEQLVIY-UHFFFAOYSA-N 4-amino-2-[2-hydroxy-4-(trifluoromethyl)phenyl]-6-piperidin-3-ylpyrimidine-5-carbonitrile hydrochloride Chemical compound Cl.Nc1nc(nc(C2CCCNC2)c1C#N)-c1ccc(cc1O)C(F)(F)F CCBBYZHOEQLVIY-UHFFFAOYSA-N 0.000 claims 1
NSCDUKLTOIHOMU-UHFFFAOYSA-N 4-amino-2-[2-hydroxy-6-(2-methylpropyl)phenyl]-6-piperidin-3-ylpyrimidine-5-carbonitrile Chemical compound CC(C)Cc1cccc(O)c1-c1nc(N)c(C#N)c(n1)C1CCCNC1 NSCDUKLTOIHOMU-UHFFFAOYSA-N 0.000 claims 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 description 81
125000004464 hydroxyphenyl group Chemical group 0.000 description 18
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 13
230000001225 therapeutic effect Effects 0.000 description 11
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 7
229940111134 coxibs Drugs 0.000 description 7
230000001315 anti-hyperlipaemic effect Effects 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
230000000694 effects Effects 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 5
108091000080 Phosphotransferase Proteins 0.000 description 5
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 5
108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 5
239000003524 antilipemic agent Substances 0.000 description 5
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