JP2009502801A

JP2009502801A - Ａｕｒｏｒａキナーゼインヒビターとして有用なピラゾロピリミジン

Ａｕｒｏｒａキナーゼインヒビターとして有用なピラゾロピリミジン Download PDF

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Publication number: JP2009502801A
Authority: JP; Japan
Prior art keywords: alkyl; aryl; heteroaryl; hydrogen; heteroalkyl
Prior art date: 2005-07-22
Legal status : Pending

Application number

JP2008522958A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009502801A5 (enExample

Inventor

ヨハンディー．オスロブ，

チュルヒュンユー，

Original Assignee

サネシスファーマシューティカルズ，インコーポレイテッド

Priority date

2005-07-22

Filing date

2006-07-21

Publication date

2009-01-29

2006-07-21 Application filed by サネシスファーマシューティカルズ，インコーポレイテッド filed Critical サネシスファーマシューティカルズ，インコーポレイテッド

2009-01-29 Publication of JP2009502801A publication Critical patent/JP2009502801A/ja

2009-09-10 Publication of JP2009502801A5 publication Critical patent/JP2009502801A5/ja

Status Pending legal-status Critical Current

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239000003719 aurora kinase inhibitor Substances 0.000 title description 4
APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 373
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 67
201000010099 disease Diseases 0.000 claims abstract description 57
239000005441 aurora Substances 0.000 claims abstract description 37
230000001404 mediated effect Effects 0.000 claims abstract description 22
102000001253 Protein Kinase Human genes 0.000 claims abstract description 16
108060006633 protein kinase Proteins 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims description 653
125000003118 aryl group Chemical group 0.000 claims description 523
125000001072 heteroaryl group Chemical group 0.000 claims description 499
229910052739 hydrogen Inorganic materials 0.000 claims description 471
239000001257 hydrogen Substances 0.000 claims description 460
125000004404 heteroalkyl group Chemical group 0.000 claims description 253
125000000623 heterocyclic group Chemical group 0.000 claims description 195
125000002252 acyl group Chemical group 0.000 claims description 156
229910052736 halogen Inorganic materials 0.000 claims description 146
150000002367 halogens Chemical class 0.000 claims description 146
229910052757 nitrogen Inorganic materials 0.000 claims description 118
239000000203 mixture Substances 0.000 claims description 92
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
125000004433 nitrogen atom Chemical group N* 0.000 claims description 81
-1 heteroaliphatic Chemical group 0.000 claims description 74
125000004093 cyano group Chemical group *C#N 0.000 claims description 69
125000004432 carbon atom Chemical group C* 0.000 claims description 61
229910052801 chlorine Inorganic materials 0.000 claims description 54
229910052731 fluorine Inorganic materials 0.000 claims description 54
125000003342 alkenyl group Chemical group 0.000 claims description 50
125000002947 alkylene group Chemical group 0.000 claims description 48
238000000034 method Methods 0.000 claims description 47
125000000753 cycloalkyl group Chemical group 0.000 claims description 46
125000000304 alkynyl group Chemical group 0.000 claims description 45
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 44
239000003814 drug Substances 0.000 claims description 44
125000001931 aliphatic group Chemical group 0.000 claims description 43
125000001188 haloalkyl group Chemical group 0.000 claims description 43
125000003545 alkoxy group Chemical group 0.000 claims description 42
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 41
125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
229910052760 oxygen Inorganic materials 0.000 claims description 32
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 30
125000002723 alicyclic group Chemical group 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 30
229940079593 drug Drugs 0.000 claims description 23
229940124597 therapeutic agent Drugs 0.000 claims description 20
125000001544 thienyl group Chemical group 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
239000012472 biological sample Substances 0.000 claims description 16
238000009472 formulation Methods 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
102000003989 Aurora kinases Human genes 0.000 claims description 8
108090000433 Aurora kinases Proteins 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 6
125000005647 linker group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
239000003981 vehicle Substances 0.000 claims description 6
125000002619 bicyclic group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000004001 thioalkyl group Chemical group 0.000 claims description 5
208000020084 Bone disease Diseases 0.000 claims description 4
208000024172 Cardiovascular disease Diseases 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 4
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
210000000056 organ Anatomy 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
108010025020 Nerve Growth Factor Proteins 0.000 claims description 3
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125000004423 acyloxy group Chemical group 0.000 claims description 3
230000001028 anti-proliverative effect Effects 0.000 claims description 3
125000002837 carbocyclic group Chemical group 0.000 claims description 3
208000014951 hematologic disease Diseases 0.000 claims description 3
230000002519 immonomodulatory effect Effects 0.000 claims description 3
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239000003018 immunosuppressive agent Substances 0.000 claims description 3
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208000019423 liver disease Diseases 0.000 claims description 3
239000003900 neurotrophic factor Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
150000003456 sulfonamides Chemical class 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
208000023275 Autoimmune disease Diseases 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000005431 alkyl carboxamide group Chemical group 0.000 claims description 2
239000003443 antiviral agent Substances 0.000 claims description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 2
125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 2
125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
230000004770 neurodegeneration Effects 0.000 claims description 2
208000015122 neurodegenerative disease Diseases 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
230000002062 proliferating effect Effects 0.000 claims description 2
125000004963 sulfonylalkyl group Chemical group 0.000 claims description 2
238000002054 transplantation Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 98
238000010276 construction Methods 0.000 claims 41
208000019838 Blood disease Diseases 0.000 claims 2
230000001066 destructive effect Effects 0.000 claims 2
206010012601 diabetes mellitus Diseases 0.000 claims 2
208000018706 hematopoietic system disease Diseases 0.000 claims 2
230000003612 virological effect Effects 0.000 claims 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
125000003368 amide group Chemical group 0.000 claims 1
230000000973 chemotherapeutic effect Effects 0.000 claims 1
238000002512 chemotherapy Methods 0.000 claims 1
208000019622 heart disease Diseases 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 22
239000008194 pharmaceutical composition Substances 0.000 abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 description 277
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
239000011541 reaction mixture Substances 0.000 description 58
239000000460 chlorine Substances 0.000 description 56
201000006417 multiple sclerosis Diseases 0.000 description 53
239000000243 solution Substances 0.000 description 52
235000019439 ethyl acetate Nutrition 0.000 description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
210000004027 cell Anatomy 0.000 description 33
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
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230000002829 reductive effect Effects 0.000 description 26
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238000006243 chemical reaction Methods 0.000 description 22
150000003839 salts Chemical class 0.000 description 21
125000001424 substituent group Chemical group 0.000 description 21
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RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
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125000005842 heteroatom Chemical group 0.000 description 17
239000008346 aqueous phase Substances 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
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239000012267 brine Substances 0.000 description 10
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208000035475 disorder Diseases 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 5
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