KR20080074161A

KR20080074161A - ＥＰＨＢ 및 ＶＥＧＦＲ２ 키나아제 억제제로서의피라졸로[１,５-ａ]피리딘-３-카르복실산

ＥＰＨＢ 및 ＶＥＧＦＲ２ 키나아제 억제제로서의피라졸로[１,５-ａ]피리딘-３-카르복실산 Download PDF

Info

Publication number: KR20080074161A
Authority: KR; South Korea
Prior art keywords: alkyl; phenyl; formula; unsubstituted; substituted
Prior art date: 2005-12-08
Legal status : Withdrawn

Application number

KR1020087013615A

Other languages

English (en)

Korean (ko)

Inventor

파트리샤 임바흐

필립 홀처

파스칼 퓌레

Original Assignee

노파르티스 아게

Priority date

2005-12-08

Filing date

2006-12-06

Publication date

2008-08-12

2005-12-08 Priority claimed from GB0525065A external-priority patent/GB0525065D0/en

2006-01-17 Priority claimed from GB0600931A external-priority patent/GB0600931D0/en

2006-12-06 Application filed by 노파르티스 아게 filed Critical 노파르티스 아게

2008-08-12 Publication of KR20080074161A publication Critical patent/KR20080074161A/ko

Status Withdrawn legal-status Critical Current

Links

HRSDPDBQVZHCRC-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)C=NN21 HRSDPDBQVZHCRC-UHFFFAOYSA-N 0.000 title abstract description 6
229940043355 kinase inhibitor Drugs 0.000 title description 5
239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
150000003839 salts Chemical group 0.000 claims abstract description 77
239000003814 drug Substances 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 266
-1 - alkyl Chemical group 0.000 claims description 160
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 99
125000000217 alkyl group Chemical group 0.000 claims description 86
201000010099 disease Diseases 0.000 claims description 81
229910052757 nitrogen Inorganic materials 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 72
239000001257 hydrogen Substances 0.000 claims description 63
238000011282 treatment Methods 0.000 claims description 63
102000001253 Protein Kinase Human genes 0.000 claims description 56
108060006633 protein kinase Proteins 0.000 claims description 56
238000000034 method Methods 0.000 claims description 55
108091000080 Phosphotransferase Proteins 0.000 claims description 47
102000020233 phosphotransferase Human genes 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 47
125000000547 substituted alkyl group Chemical group 0.000 claims description 46
150000002431 hydrogen Chemical group 0.000 claims description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
125000003107 substituted aryl group Chemical group 0.000 claims description 40
206010028980 Neoplasm Diseases 0.000 claims description 39
125000005843 halogen group Chemical group 0.000 claims description 38
230000005764 inhibitory process Effects 0.000 claims description 35
108090000623 proteins and genes Proteins 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 31
102000004169 proteins and genes Human genes 0.000 claims description 31
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 30
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
241001465754 Metazoa Species 0.000 claims description 21
230000002401 inhibitory effect Effects 0.000 claims description 21
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
201000011510 cancer Diseases 0.000 claims description 17
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 16
125000001624 naphthyl group Chemical group 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 14
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 14
230000033115 angiogenesis Effects 0.000 claims description 13
125000001246 bromo group Chemical group Br* 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
102000050554 Eph Family Receptors Human genes 0.000 claims description 12
108091008815 Eph receptors Proteins 0.000 claims description 12
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
230000002062 proliferating effect Effects 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
208000032839 leukemia Diseases 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
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208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
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102000029330 CSK Tyrosine-Protein Kinase Human genes 0.000 claims description 5
108010069682 CSK Tyrosine-Protein Kinase Proteins 0.000 claims description 5
101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims description 5
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239000003937 drug carrier Substances 0.000 claims description 5
210000003734 kidney Anatomy 0.000 claims description 5
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
230000035755 proliferation Effects 0.000 claims description 5
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
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206010025323 Lymphomas Diseases 0.000 claims description 4
208000034578 Multiple myelomas Diseases 0.000 claims description 4
206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
230000003511 endothelial effect Effects 0.000 claims description 4
230000006698 induction Effects 0.000 claims description 4
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210000004072 lung Anatomy 0.000 claims description 4
201000001441 melanoma Diseases 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 4
125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
230000008929 regeneration Effects 0.000 claims description 4
238000011069 regeneration method Methods 0.000 claims description 4
230000011664 signaling Effects 0.000 claims description 4
125000005505 thiomorpholino group Chemical group 0.000 claims description 4
206010039491 Sarcoma Diseases 0.000 claims description 3
208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims description 3
210000003050 axon Anatomy 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
210000000481 breast Anatomy 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
230000004761 fibrosis Effects 0.000 claims description 3
201000000459 head and neck squamous cell carcinoma Diseases 0.000 claims description 3
208000006178 malignant mesothelioma Diseases 0.000 claims description 3
201000005282 malignant pleural mesothelioma Diseases 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
210000002307 prostate Anatomy 0.000 claims description 3
210000000664 rectum Anatomy 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
230000000638 stimulation Effects 0.000 claims description 3
210000002784 stomach Anatomy 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
238000002054 transplantation Methods 0.000 claims description 3
210000003932 urinary bladder Anatomy 0.000 claims description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
VOZRGVOHRTXRBW-UHFFFAOYSA-N 6-(4-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN2N=CC(C(=O)NC=3C(=CC=CC=3)C)=C2C=C1 VOZRGVOHRTXRBW-UHFFFAOYSA-N 0.000 claims description 2
201000009030 Carcinoma Diseases 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
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208000010412 Glaucoma Diseases 0.000 claims description 2
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208000017604 Hodgkin disease Diseases 0.000 claims description 2
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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206010052779 Transplant rejections Diseases 0.000 claims description 2
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125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
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125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
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125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
201000003142 neovascular glaucoma Diseases 0.000 claims description 2
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125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 2
210000001428 peripheral nervous system Anatomy 0.000 claims description 2
125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000005936 piperidyl group Chemical group 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
CJPZOHYELJKKEL-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN2N=CC(C(=O)NC=3C(=CC=CC=3)C)=C2C=C1 CJPZOHYELJKKEL-UHFFFAOYSA-N 0.000 claims 1
NTDHZKMLYLHSHG-UHFFFAOYSA-N 6-(3-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound COC1=CC=CC(C2=CN3N=CC(=C3C=C2)C(=O)NC=2C(=CC=CC=2)C)=C1 NTDHZKMLYLHSHG-UHFFFAOYSA-N 0.000 claims 1
FNLOOMKOQOZFEH-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-n-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=NN2C=C(S(=O)(=O)N(C)C)C=CC2=C1C(=O)NC(C(=CC=1)C)=CC=1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FNLOOMKOQOZFEH-UHFFFAOYSA-N 0.000 claims 1
CUFXCXRHYOZGHC-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-n-[5-[[4-methoxy-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical class C1=C(C(F)(F)F)C(OC)=CC=C1NC(=O)C1=CC=C(C)C(NC(=O)C2=C3C=CC(=CN3N=C2)S(=O)(=O)N(C)C)=C1 CUFXCXRHYOZGHC-UHFFFAOYSA-N 0.000 claims 1
WRIUDPIXTLSRHB-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN2N=CC(C(=O)NC=3C(=CC=CC=3)C)=C2C=C1 WRIUDPIXTLSRHB-UHFFFAOYSA-N 0.000 claims 1
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GKKBOYULKXSRJE-UHFFFAOYSA-N n-(2-methylphenyl)-6-(4-morpholin-4-ylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=C2C=CC(C=3C=CC(=CC=3)N3CCOCC3)=CN2N=C1 GKKBOYULKXSRJE-UHFFFAOYSA-N 0.000 claims 1
GVSAVGKQNHLKIZ-UHFFFAOYSA-N n-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]-6-phenylpyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C2=C3C=CC(=CN3N=C2)C=2C=CC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GVSAVGKQNHLKIZ-UHFFFAOYSA-N 0.000 claims 1
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