CA2643066A1 - Pyrazoles - Google Patents

Pyrazoles Download PDF

Info

Publication number: CA2643066A1
Authority: CA; Canada
Prior art keywords: pyrazol; pyrimidin; chloro; cycloheteroalkyl; alkyl
Prior art date: 2006-03-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002643066A

Other languages

English (en)

Inventor

Michael John Bennett

Sujin Cho-Schultz

Judith Gail Deal

Stephen Joseph King

Tami Jo Marrone

Cynthia Louise Palmer

William Henry Romines, Iii

Eugene Yuanjin Rui

Scott Channing Sutton

Luke Raymond Zehnder

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-03-16

Filing date

2007-03-05

Publication date

2007-09-20

2007-03-05 Application filed by Individual filed Critical Individual

2007-09-20 Publication of CA2643066A1 publication Critical patent/CA2643066A1/fr

Status Abandoned legal-status Critical Current

Links

150000003217 pyrazoles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 282
150000003839 salts Chemical class 0.000 claims abstract description 60
239000012453 solvate Substances 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims description 135
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 131
125000000217 alkyl group Chemical group 0.000 claims description 95
125000000753 cycloalkyl group Chemical group 0.000 claims description 70
125000003118 aryl group Chemical group 0.000 claims description 60
125000001072 heteroaryl group Chemical group 0.000 claims description 50
125000003342 alkenyl group Chemical group 0.000 claims description 49
125000000304 alkynyl group Chemical group 0.000 claims description 48
230000002159 abnormal effect Effects 0.000 claims description 28
230000010261 cell growth Effects 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
241000124008 Mammalia Species 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 18
239000008194 pharmaceutical composition Substances 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
102000004190 Enzymes Human genes 0.000 claims description 12
108090000790 Enzymes Proteins 0.000 claims description 12
230000002401 inhibitory effect Effects 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
YQXGDHXOMSGGQH-NSHDSACASA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 YQXGDHXOMSGGQH-NSHDSACASA-N 0.000 claims description 5
ZLIDDUTZCPVGNS-UHFFFAOYSA-N 3-chloro-5-[4-[2-(2-methylpropylamino)pyrimidin-4-yl]-1-piperidin-4-ylpyrazol-3-yl]phenol Chemical compound CC(C)CNC1=NC=CC(C=2C(=NN(C=2)C2CCNCC2)C=2C=C(Cl)C=C(O)C=2)=N1 ZLIDDUTZCPVGNS-UHFFFAOYSA-N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
AQEWOFAXNIOSSX-UHFFFAOYSA-N 3-[4-(2-anilinopyrimidin-4-yl)-1-methylpyrazol-3-yl]-5-chlorophenol Chemical compound N=1N(C)C=C(C=2N=C(NC=3C=CC=CC=3)N=CC=2)C=1C1=CC(O)=CC(Cl)=C1 AQEWOFAXNIOSSX-UHFFFAOYSA-N 0.000 claims description 4
HAMFJFQUVMALFI-UHFFFAOYSA-N 3-chloro-5-[4-[2-[(2-hydroxy-2-methylpropyl)amino]pyrimidin-4-yl]-1-(1-methylpiperidin-4-yl)pyrazol-3-yl]phenol Chemical compound C1CN(C)CCC1N1N=C(C=2C=C(Cl)C=C(O)C=2)C(C=2N=C(NCC(C)(C)O)N=CC=2)=C1 HAMFJFQUVMALFI-UHFFFAOYSA-N 0.000 claims description 4
ATSWJIUDTSEHJK-UHFFFAOYSA-N 2-[3-(3-chloro-4-fluoro-5-hydroxyphenyl)-4-[2-(2-hydroxyethylamino)pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OCCNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C(F)=C(O)C=2)=N1 ATSWJIUDTSEHJK-UHFFFAOYSA-N 0.000 claims description 3
SACNZPAIRMXQJM-UHFFFAOYSA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-(1-hydroxypropan-2-ylamino)pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OCC(C)NC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 SACNZPAIRMXQJM-UHFFFAOYSA-N 0.000 claims description 3
AIXCDRASCBHHJL-UHFFFAOYSA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-(oxolan-3-ylamino)pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OC1=CC(Cl)=CC(C=2C(=CN(CC#N)N=2)C=2N=C(NC3COCC3)N=CC=2)=C1 AIXCDRASCBHHJL-UHFFFAOYSA-N 0.000 claims description 3
SACNZPAIRMXQJM-LLVKDONJSA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OC[C@@H](C)NC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 SACNZPAIRMXQJM-LLVKDONJSA-N 0.000 claims description 3
SACNZPAIRMXQJM-NSHDSACASA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-[[(2s)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OC[C@H](C)NC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 SACNZPAIRMXQJM-NSHDSACASA-N 0.000 claims description 3
DWQTXXYKISMEDK-ZDUSSCGKSA-N 2-[3-(3-hydroxy-5-methylphenyl)-4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 DWQTXXYKISMEDK-ZDUSSCGKSA-N 0.000 claims description 3
UFXRKOISIAFFNT-UHFFFAOYSA-N 2-[3-(4-fluoro-3-hydroxy-5-methylphenyl)-4-[2-(methylamino)pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C(F)=C(C)C=2)=N1 UFXRKOISIAFFNT-UHFFFAOYSA-N 0.000 claims description 3
ZSNIWZXHXQKDEB-UHFFFAOYSA-N 2-[4-(2-aminopyrimidin-4-yl)-3-(3-chloro-5-hydroxyphenyl)pyrazol-1-yl]acetonitrile Chemical compound NC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 ZSNIWZXHXQKDEB-UHFFFAOYSA-N 0.000 claims description 3
QIZRVGPQRIIAJH-UHFFFAOYSA-N 3-chloro-5-[1-(1-methylpiperidin-4-yl)-4-[2-(2-methylpropylamino)pyrimidin-4-yl]pyrazol-3-yl]phenol Chemical compound CC(C)CNC1=NC=CC(C=2C(=NN(C=2)C2CCN(C)CC2)C=2C=C(Cl)C=C(O)C=2)=N1 QIZRVGPQRIIAJH-UHFFFAOYSA-N 0.000 claims description 3
SBHPPHLJUSGZCI-UHFFFAOYSA-N 3-chloro-5-[1-methyl-4-[2-(2-methylpropylamino)pyrimidin-4-yl]pyrazol-3-yl]phenol Chemical compound CC(C)CNC1=NC=CC(C=2C(=NN(C)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 SBHPPHLJUSGZCI-UHFFFAOYSA-N 0.000 claims description 3
CRIRNSDYCSBYRH-UHFFFAOYSA-N 3-methyl-5-[1-(1-methylazetidin-3-yl)-4-[2-(2-pyrazin-2-ylethylamino)pyrimidin-4-yl]pyrazol-3-yl]phenol Chemical compound C1N(C)CC1N1N=C(C=2C=C(O)C=C(C)C=2)C(C=2N=C(NCCC=3N=CC=NC=3)N=CC=2)=C1 CRIRNSDYCSBYRH-UHFFFAOYSA-N 0.000 claims description 3
RNAABPBRFRQBJF-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-4-[2-(oxolan-3-ylmethylamino)pyrimidin-4-yl]pyrazol-3-yl]-2,3-dimethylphenol Chemical compound OC1=C(C)C(C)=CC(C=2C(=CN(CCO)N=2)C=2N=C(NCC3COCC3)N=CC=2)=C1 RNAABPBRFRQBJF-UHFFFAOYSA-N 0.000 claims description 3
DFTLXLKENXFEJB-SFHVURJKSA-N [(2s)-1-[[4-[1-(cyanomethyl)-3-(3-hydroxy-5-methylphenyl)pyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl] 2,6-dimethoxybenzoate Chemical compound COC1=CC=CC(OC)=C1C(=O)O[C@@H](C)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 DFTLXLKENXFEJB-SFHVURJKSA-N 0.000 claims description 3
230000002255 enzymatic effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
GHKTUWQMPARWQM-UHFFFAOYSA-N 2,3-dimethyl-5-[1-(1-methylazetidin-3-yl)-4-[2-(propan-2-ylamino)pyrimidin-4-yl]pyrazol-3-yl]phenol Chemical compound CC(C)NC1=NC=CC(C=2C(=NN(C=2)C2CN(C)C2)C=2C=C(O)C(C)=C(C)C=2)=N1 GHKTUWQMPARWQM-UHFFFAOYSA-N 0.000 claims description 2
SWKWJWLBAJDORP-UHFFFAOYSA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-[2-(1h-imidazol-5-yl)ethylamino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound OC1=CC(Cl)=CC(C=2C(=CN(CC#N)N=2)C=2N=C(NCCC=3NC=NC=3)N=CC=2)=C1 SWKWJWLBAJDORP-UHFFFAOYSA-N 0.000 claims description 2
YQXGDHXOMSGGQH-LLVKDONJSA-N 2-[3-(3-chloro-5-hydroxyphenyl)-4-[2-[[(2r)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound C[C@@H](O)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(Cl)C=C(O)C=2)=N1 YQXGDHXOMSGGQH-LLVKDONJSA-N 0.000 claims description 2
ZTMWTXLQNWCMGA-NSHDSACASA-N 2-[3-(3-fluoro-5-hydroxyphenyl)-4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(F)C=C(O)C=2)=N1 ZTMWTXLQNWCMGA-NSHDSACASA-N 0.000 claims description 2
VYRHVPUPLCYMAB-ZDUSSCGKSA-N 2-[3-(3-hydroxy-4,5-dimethylphenyl)-4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]acetonitrile Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C(C)=C(C)C=2)=N1 VYRHVPUPLCYMAB-ZDUSSCGKSA-N 0.000 claims description 2
KMIFLCWYMBGLPD-UHFFFAOYSA-N 2-[3-(3-hydroxy-5-methylphenyl)-4-[2-(methylamino)pyrimidin-4-yl]pyrazol-1-yl]-n-methylacetamide Chemical compound N=1N(CC(=O)NC)C=C(C=2N=C(NC)N=CC=2)C=1C1=CC(C)=CC(O)=C1 KMIFLCWYMBGLPD-UHFFFAOYSA-N 0.000 claims description 2
JZMFYLPERDCCQR-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)pyrimidin-4-yl]-3-(3-hydroxy-5-methylphenyl)pyrazol-1-yl]acetonitrile Chemical compound CN(C)C1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 JZMFYLPERDCCQR-UHFFFAOYSA-N 0.000 claims description 2
AVKXRQRMYRNTQN-UHFFFAOYSA-N 3-[3-(3-hydroxy-5-methylphenyl)-4-[2-(oxolan-3-ylamino)pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound CC1=CC(O)=CC(C=2C(=CN(CCC#N)N=2)C=2N=C(NC3COCC3)N=CC=2)=C1 AVKXRQRMYRNTQN-UHFFFAOYSA-N 0.000 claims description 2
CMPCGTMFOBMOLF-AWEZNQCLSA-N 3-[3-(3-hydroxy-5-methylphenyl)-4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CCC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 CMPCGTMFOBMOLF-AWEZNQCLSA-N 0.000 claims description 2
HGDCZIDSRCULBR-UHFFFAOYSA-N 3-[4-[2-(2-hydroxyethylamino)pyrimidin-4-yl]-3-(3-hydroxy-5-methylphenyl)pyrazol-1-yl]propanenitrile Chemical compound CC1=CC(O)=CC(C=2C(=CN(CCC#N)N=2)C=2N=C(NCCO)N=CC=2)=C1 HGDCZIDSRCULBR-UHFFFAOYSA-N 0.000 claims description 2
RBJVRTWYYCSXBS-AWEZNQCLSA-N 3-[4-[2-[[(2s)-2-hydroxypropyl]amino]pyrimidin-4-yl]-1-[(5-methyl-1,2-oxazol-3-yl)methyl]pyrazol-3-yl]-5-methylphenol Chemical compound C[C@H](O)CNC1=NC=CC(C=2C(=NN(CC3=NOC(C)=C3)C=2)C=2C=C(O)C=C(C)C=2)=N1 RBJVRTWYYCSXBS-AWEZNQCLSA-N 0.000 claims description 2
UMVUYBKFIMXTFT-UHFFFAOYSA-N 3-chloro-5-(1-propan-2-yl-4-pyrimidin-4-ylpyrazol-3-yl)phenol Chemical compound N=1N(C(C)C)C=C(C=2N=CN=CC=2)C=1C1=CC(O)=CC(Cl)=C1 UMVUYBKFIMXTFT-UHFFFAOYSA-N 0.000 claims description 2
ZIXWBBGDQYIENE-UHFFFAOYSA-N 3-methyl-5-[1-(1-methylazetidin-3-yl)-4-[2-(2-methylpropylamino)pyrimidin-4-yl]pyrazol-3-yl]phenol Chemical compound CC(C)CNC1=NC=CC(C=2C(=NN(C=2)C2CN(C)C2)C=2C=C(O)C=C(C)C=2)=N1 ZIXWBBGDQYIENE-UHFFFAOYSA-N 0.000 claims description 2
BBLLEUAYHZXSRA-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-4-[2-[2-(1-methylpyrrolidin-2-yl)ethylamino]pyrimidin-4-yl]pyrazol-3-yl]-2,3-dimethylphenol Chemical compound CN1CCCC1CCNC1=NC=CC(C=2C(=NN(CCO)C=2)C=2C=C(O)C(C)=C(C)C=2)=N1 BBLLEUAYHZXSRA-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
DJLFDPQKLAVSHL-UHFFFAOYSA-N 2-[4-[2-[2-hydroxyethyl(methyl)amino]pyrimidin-4-yl]-3-(3-hydroxy-5-methylphenyl)pyrazol-1-yl]acetonitrile Chemical compound OCCN(C)C1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 DJLFDPQKLAVSHL-UHFFFAOYSA-N 0.000 claims 1
RXHMEYGGRDTZQL-UHFFFAOYSA-N 3-[1-(cyanomethyl)-4-[2-(2-hydroxyethylamino)pyrimidin-4-yl]pyrazol-3-yl]-5-hydroxybenzonitrile Chemical compound OCCNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(C=C(O)C=2)C#N)=N1 RXHMEYGGRDTZQL-UHFFFAOYSA-N 0.000 claims 1
LASRDKLTSMEGOO-AWEZNQCLSA-N [(2s)-1-[[4-[1-(cyanomethyl)-3-(3-hydroxy-5-methylphenyl)pyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)CNC1=NC=CC(C=2C(=NN(CC#N)C=2)C=2C=C(O)C=C(C)C=2)=N1 LASRDKLTSMEGOO-AWEZNQCLSA-N 0.000 claims 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 33
230000015572 biosynthetic process Effects 0.000 abstract description 11
238000003786 synthesis reaction Methods 0.000 abstract description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 194
229910052739 hydrogen Inorganic materials 0.000 description 173
239000000203 mixture Substances 0.000 description 163
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 156
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 124
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 122
229910052740 iodine Inorganic materials 0.000 description 105
238000005481 NMR spectroscopy Methods 0.000 description 97
-1 aliphatic hydrocarbon radical Chemical class 0.000 description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 90
239000000243 solution Substances 0.000 description 89
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
238000002360 preparation method Methods 0.000 description 74
235000019439 ethyl acetate Nutrition 0.000 description 70
239000000460 chlorine Substances 0.000 description 65
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
229910052757 nitrogen Inorganic materials 0.000 description 47
238000006243 chemical reaction Methods 0.000 description 39
239000003795 chemical substances by application Substances 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
206010028980 Neoplasm Diseases 0.000 description 33
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 32
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
229920006395 saturated elastomer Polymers 0.000 description 30
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
210000004027 cell Anatomy 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
238000010898 silica gel chromatography Methods 0.000 description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
239000002904 solvent Substances 0.000 description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000002246 antineoplastic agent Substances 0.000 description 21
239000002585 base Substances 0.000 description 21
201000010099 disease Diseases 0.000 description 21
239000010410 layer Substances 0.000 description 21
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 18
238000009472 formulation Methods 0.000 description 17
VQGISNOMGHCEPX-UHFFFAOYSA-N propanenitrile Chemical compound C[CH]C#N VQGISNOMGHCEPX-UHFFFAOYSA-N 0.000 description 17
238000000746 purification Methods 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
239000000725 suspension Substances 0.000 description 17
201000011510 cancer Diseases 0.000 description 16
230000000694 effects Effects 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
238000003756 stirring Methods 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 15
239000012267 brine Substances 0.000 description 15
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 12
125000004429 atom Chemical group 0.000 description 12
239000000969 carrier Substances 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 12
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 11
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 11
229910000024 caesium carbonate Inorganic materials 0.000 description 11
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ZPUHVPYXSITYDI-HEUWMMRCSA-N xyotax Chemical compound OC(=O)[C@@H](N)CCC(O)=O.O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 ZPUHVPYXSITYDI-HEUWMMRCSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229940033942 zoladex Drugs 0.000 description 1
229960004276 zoledronic acid Drugs 0.000 description 1
XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002643066A 2006-03-16 2007-03-05 Pyrazoles Abandoned CA2643066A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US78278606P	2006-03-16	2006-03-16
US60/782,786		2006-03-16
US88656107P	2007-01-25	2007-01-25
US60/886,561		2007-01-25
PCT/IB2007/000561 WO2007105058A2 (fr)	2006-03-16	2007-03-05	Pyrazoles

Publications (1)

Publication Number	Publication Date
CA2643066A1 true CA2643066A1 (fr)	2007-09-20

Family

ID=38235169

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002643066A Abandoned CA2643066A1 (fr)	2006-03-16	2007-03-05	Pyrazoles

Country Status (4)

Country	Link
EP (1)	EP2024353A2 (fr)
JP (1)	JP2009530261A (fr)
CA (1)	CA2643066A1 (fr)
WO (1)	WO2007105058A2 (fr)

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AR077975A1 (es)	2009-08-28	2011-10-05	Irm Llc	Derivados de pirazol pirimidina y composiciones como inhibidores de cinasa de proteina
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KR101123071B1 (ko) *	2009-10-23	2012-03-05	한국과학기술연구원	신규 이미다졸 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 흑색종의 예방 및 치료용 약학적 조성물
ME01908B (me)	2009-12-17	2014-12-20	Boehringer Ingelheim Int	Novi antagonisti ccr2 receptora i njihova primjena
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AR081810A1 (es)	2010-04-07	2012-10-24	Bayer Cropscience Ag	Piridinilpirazoles biciclicos
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WO2011141477A1 (fr)	2010-05-12	2011-11-17	Boehringer Ingelheim International Gmbh	Nouveaux antagonistes du récepteur ccr2, leur procédé de production et leur utilisation en tant que médicaments
US8841313B2 (en)	2010-05-17	2014-09-23	Boehringer Ingelheim International Gmbh	CCR2 antagonists and uses thereof
WO2011147772A1 (fr)	2010-05-25	2011-12-01	Boehringer Ingelheim International Gmbh	Antagonistes du récepteur ccr2
EP2576538B1 (fr)	2010-06-01	2015-10-28	Boehringer Ingelheim International GmbH	Nouveaux antagonistes de CCR2
EP2601185B1 (fr)	2010-08-03	2015-10-07	Nerviano Medical Sciences S.r.l.	Dérivés de composés de pyrazolophényl-benzènesulfonamide et leur utilisation en tant qu'agents antitumoraux
PL2647629T3 (pl) *	2010-12-01	2015-12-31	Nissan Chemical Ind Ltd	Związki pirazolowe o terapeutycznym działaniu na szpiczaka mnogiego
MX2013009931A (es)	2011-04-18	2013-10-01	Eisai R&D Man Co Ltd	Agentes terapeuticos contra tumores.
EP2731941B1 (fr)	2011-07-15	2019-05-08	Boehringer Ingelheim International GmbH	Antagonistes ccr2, nouveaux et sélectifs
BR112014011223A8 (pt)	2011-11-11	2023-01-31	Novartis Ag	Método de tratar uma doença proliferativa
KR102091295B1 (ko)	2011-11-23	2020-03-19	어레이 바이오파마 인크.	제약 제제
AU2014372166B2 (en)	2013-12-23	2017-10-26	Novartis Ag	Pharmaceutical combinations
AU2016287584B2 (en)	2015-07-02	2020-03-26	Centrexion Therapeutics Corporation	(4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate
US11066404B2 (en)	2018-10-11	2021-07-20	Incyte Corporation	Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors
WO2020168197A1 (fr)	2019-02-15	2020-08-20	Incyte Corporation	Composés de pyrrolo[2,3-d]pyrimidinone en tant qu'inhibiteurs de cdk2
TW202100520A (zh)	2019-03-05	2021-01-01	美商英塞特公司	作為cdk2 抑制劑之吡唑基嘧啶基胺化合物
WO2020205560A1 (fr)	2019-03-29	2020-10-08	Incyte Corporation	Composés sulfonylamides utilisés comme inhibiteurs de la cdk2
US11440914B2 (en)	2019-05-01	2022-09-13	Incyte Corporation	Tricyclic amine compounds as CDK2 inhibitors
WO2020223558A1 (fr)	2019-05-01	2020-11-05	Incyte Corporation	Composés aminés tricycliques en tant qu'inhibiteurs de cdk2
TW202115024A (zh)	2019-08-14	2021-04-16	美商英塞特公司	作為cdk2 抑制劑之咪唑基嘧啶基胺化合物
CN119930610A (zh)	2019-10-11	2025-05-06	因赛特公司	作为cdk2抑制剂的双环胺
WO2021120890A1 (fr)	2019-12-20	2021-06-24	Novartis Ag	Dérivés pyrazolyle utiles en tant qu'agents anticancéreux
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2007
- 2007-03-05 JP JP2008558927A patent/JP2009530261A/ja not_active Withdrawn
- 2007-03-05 EP EP07705682A patent/EP2024353A2/fr not_active Withdrawn
- 2007-03-05 CA CA002643066A patent/CA2643066A1/fr not_active Abandoned
- 2007-03-05 WO PCT/IB2007/000561 patent/WO2007105058A2/fr not_active Ceased

Also Published As

Publication number	Publication date
WO2007105058A8 (fr)	2008-10-16
WO2007105058A2 (fr)	2007-09-20
WO2007105058A3 (fr)	2007-12-21
EP2024353A2 (fr)	2009-02-18
JP2009530261A (ja)	2009-08-27

Publication	Publication Date	Title
CA2643066A1 (fr)	2007-09-20	Pyrazoles
US7772246B2 (en)	2010-08-10	Pyrazole compounds as RAF inhibitors
AU2007297212B2 (en)	2011-04-14	Pyrido (2, 3-D) pyrimidinone compounds and their use as PI3 inhibitors
US20090111805A1 (en)	2009-04-30	Bicyclic heteroaromatic derivatives useful as anticancer agents
JP2008540395A (ja)	2008-11-20	アミドレソルシノール化合物
WO2007023382A2 (fr)	2007-03-01	Composes de pyrimidine amino pyrazole, puissants inhibiteurs de kinase
EP2118111B1 (fr)	2011-03-23	Dérivés de 2-amino-5,7-dihydro-6h-pyrrolo [3,4-d] pyrimidine en tant qu'inhibiteurs de la hsp 90 pour le traitement du cancer
WO2008059368A2 (fr)	2008-05-22	Composés de 2-amino pyridine
WO2014047427A2 (fr)	2014-03-27	Inhibiteurs de la mcl-1 à base de benzofurane, de benzothiophène et d'indole substitués
WO2006067614A2 (fr)	2006-06-29	Derives heteroaromatiques utiles en tant qu'agents anticancereux
TW202342464A (zh)	2023-11-01	Rna解旋酶dhx9之抑制劑及其用途
CA2732922A1 (fr)	2010-02-18	Composes 2-amino pyrimidine comme inhibiteurs puissants de l'hsp-90
ES2402855T3 (es)	2013-05-09	Derivados de cianuro de azol-metilideno y su uso como moduladores de proteína cinasas
CN101663305A (zh)	2010-03-03	作为hsp-90抑制剂用于治疗癌症的2-氨基-5,7-二氢-6h-吡咯并[3,4-d]嘧啶衍生物
HK1139668A (en)	2010-09-24	2-amino-5, 7-dihydro-6h-pyrrolo[3,4-d]pyrimidine derivatives as hsp-90 inhibitors for treating cancer

Legal Events

Date	Code	Title	Description
2008-08-20	EEER	Examination request
2011-03-07	FZDE	Dead