JP2014521696A5 - - Google Patents
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- Publication number
- JP2014521696A5 JP2014521696A5 JP2014524111A JP2014524111A JP2014521696A5 JP 2014521696 A5 JP2014521696 A5 JP 2014521696A5 JP 2014524111 A JP2014524111 A JP 2014524111A JP 2014524111 A JP2014524111 A JP 2014524111A JP 2014521696 A5 JP2014521696 A5 JP 2014521696A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluoro
- quinazoline
- ylamino
- phenyl
- Prior art date
- 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.)
- Granted
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- -1 2-oxabicyclo [2.2.1] heptan-5-yl Chemical group 0.000 claims description 159
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 54
- TYHCBIKGTCZFTK-UHFFFAOYSA-N quinazoline-7-carboxamide Chemical compound C1=NC=NC2=CC(C(=O)N)=CC=C21 TYHCBIKGTCZFTK-UHFFFAOYSA-N 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 230000003463 hyperproliferative effect Effects 0.000 claims description 18
- WIVJYUYFVAZMMS-UHFFFAOYSA-N 2-(oxan-4-ylamino)quinazoline-7-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2C=NC=1NC1CCOCC1 WIVJYUYFVAZMMS-UHFFFAOYSA-N 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- AYDRXUGEVYPGIK-UHFFFAOYSA-N quinazoline-7-carbohydrazide Chemical compound C1=NC=NC2=CC(C(=O)NN)=CC=C21 AYDRXUGEVYPGIK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
- 125000006309 butyl amino group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- NWUZPNZUNARLLZ-LBPRGKRZSA-N (s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methanamine Chemical compound C1=C(F)C(OC)=CC=C1[C@H](N)C1=CN(C)N=C1 NWUZPNZUNARLLZ-LBPRGKRZSA-N 0.000 claims description 2
- NBXOSGJMUZEDBS-QFIPXVFZSA-N 2-(2-cyanoethylamino)-5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NCCC#N)=N2)C2=C1 NBXOSGJMUZEDBS-QFIPXVFZSA-N 0.000 claims description 2
- HNMQRKFRTUIPCB-DEOSSOPVSA-N 2-[(2,5-dimethylpyrazol-3-yl)amino]-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(NC=2N(N=C(C)C=2)C)=N2)C2=C1 HNMQRKFRTUIPCB-DEOSSOPVSA-N 0.000 claims description 2
- KLXOIEADLOCBLO-OECQAKIHSA-N 2-[[(1R)-1-cyclopropylethyl]amino]-N-[(R)-(3-fluoro-4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methyl]quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1OC)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)N[C@H](C)C1CC1 KLXOIEADLOCBLO-OECQAKIHSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- UEOXRBXYKVEYEB-HXOBKFHXSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3r)-oxolan-3-yl]amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(N[C@H]2COCC2)=N2)C2=C1 UEOXRBXYKVEYEB-HXOBKFHXSA-N 0.000 claims description 2
- YHZOHYDIEKONRJ-DPLHUUCSSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3s,4s)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(N[C@@H]2[C@@H](COCC2)F)=N2)C2=C1 YHZOHYDIEKONRJ-DPLHUUCSSA-N 0.000 claims description 2
- AEOHEXWDZQICMA-QHCPKHFHSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(2-methyltriazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=NN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NC2CCOCC2)=N2)C2=C1 AEOHEXWDZQICMA-QHCPKHFHSA-N 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 206010001233 Adenoma benign Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- SUACLAUUOPMUKK-WCSIJFPASA-N CC1(COC1)N[C@@H]2N=CC3=C(N2C(C4=CC(=C(C=C4)OC)F)C5=CN(N=C5)C)C=CC=C3F Chemical compound CC1(COC1)N[C@@H]2N=CC3=C(N2C(C4=CC(=C(C=C4)OC)F)C5=CN(N=C5)C)C=CC=C3F SUACLAUUOPMUKK-WCSIJFPASA-N 0.000 claims description 2
- UPISKIFWDKTLLE-SKCDSABHSA-N CC1=NC=C(N1)[C@H](C2=CC(=C(C=C2)OC)F)N3C(N=CC4=C3C=CC=C4F)NC5CCOCC5 Chemical compound CC1=NC=C(N1)[C@H](C2=CC(=C(C=C2)OC)F)N3C(N=CC4=C3C=CC=C4F)NC5CCOCC5 UPISKIFWDKTLLE-SKCDSABHSA-N 0.000 claims description 2
- DQWWSJYXTRBOOL-CGAIIQECSA-N CN1C=C(C=N1)C(C2=CC(=CC=C2)F)N3[C@@H](N=CC4=C3C=CC=C4F)NC5CCOCC5 Chemical compound CN1C=C(C=N1)C(C2=CC(=CC=C2)F)N3[C@@H](N=CC4=C3C=CC=C4F)NC5CCOCC5 DQWWSJYXTRBOOL-CGAIIQECSA-N 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- WNSYKSQGFKHXNC-QHCPKHFHSA-N FC(OC1=CC=C(C=C1)[C@@H](C=1C=NN(C1)C)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F Chemical compound FC(OC1=CC=C(C=C1)[C@@H](C=1C=NN(C1)C)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F WNSYKSQGFKHXNC-QHCPKHFHSA-N 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 2
- AFAWDEPWXNAQDC-XUZZJYLKSA-N N-[(R)-(3-fluoro-4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1OC)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1 AFAWDEPWXNAQDC-XUZZJYLKSA-N 0.000 claims description 2
- XBGYKGMFTCOQNV-JTHBVZDNSA-N N-[(R)-(4-chloro-3-fluorophenyl)-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound ClC1=C(C=C(C=C1)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F XBGYKGMFTCOQNV-JTHBVZDNSA-N 0.000 claims description 2
- WPDRHVKUBYGIJD-JTHBVZDNSA-N N-[(R)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1C(F)(F)F)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1 WPDRHVKUBYGIJD-JTHBVZDNSA-N 0.000 claims description 2
- JYEXVJLIAPTLGM-PZJWPPBQSA-N N-[(R)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-2-yl]methyl]-2-(propan-2-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1C(F)(F)F)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC(C)C JYEXVJLIAPTLGM-PZJWPPBQSA-N 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 210000002615 epidermis Anatomy 0.000 claims description 2
- 230000003325 follicular Effects 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000003849 large cell carcinoma Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 208000025113 myeloid leukemia Diseases 0.000 claims description 2
- QSUJYAYZUAGHMC-UHFFFAOYSA-N n-[(3-chloro-4-fluorophenyl)-(3-fluoropyrrolidin-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1C(C1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-UHFFFAOYSA-N 0.000 claims description 2
- RCDKWQHFIJMQDJ-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound CN1C=CC(C(NC(=O)C=2C=C3N=C(NC4CCOCC4)N=CC3=CC=2)C=2C=C(F)C(Cl)=CC=2)=N1 RCDKWQHFIJMQDJ-UHFFFAOYSA-N 0.000 claims description 2
- OZPDXPIOCLPNAM-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1C(C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 OZPDXPIOCLPNAM-UHFFFAOYSA-N 0.000 claims description 2
- KJYWWRQXFYFUCA-JRTLGTJJSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s)-1-hydroxypropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C=1C2=NC(N[C@H](CO)C)=NC=C2C=CC=1C(=O)NC(C=1C=C(F)C(Cl)=CC=1)C=1C=NN(C)C=1 KJYWWRQXFYFUCA-JRTLGTJJSA-N 0.000 claims description 2
- SAXAAPPSFKUDQZ-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(3-fluoropyrrolidin-3-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound CN1N=CC=C1NC1=NC=C(C=CC(=C2)C(=O)NC(C=3C=C(F)C(Cl)=CC=3)C3(F)CNCC3)C2=N1 SAXAAPPSFKUDQZ-UHFFFAOYSA-N 0.000 claims description 2
- QSUJYAYZUAGHMC-RCZVLFRGSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3r)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-RCZVLFRGSA-N 0.000 claims description 2
- SYKRLDPZXIDMRJ-JPYJTQIMSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3r)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-JPYJTQIMSA-N 0.000 claims description 2
- QSUJYAYZUAGHMC-RDGATRHJSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3s)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-RDGATRHJSA-N 0.000 claims description 2
- SYKRLDPZXIDMRJ-MBSDFSHPSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3s)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-MBSDFSHPSA-N 0.000 claims description 2
- KJYWWRQXFYFUCA-YEJXKQKISA-N n-[(r)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s)-1-hydroxypropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C=1([C@H](NC(=O)C=2C=CC3=CN=C(N=C3C=2)N[C@H](CO)C)C=2C=C(F)C(Cl)=CC=2)C=NN(C)C=1 KJYWWRQXFYFUCA-YEJXKQKISA-N 0.000 claims description 2
- HBBURBVOOIZAEO-XMMPIXPASA-N n-[(r)-(4-cyano-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@@H](C=1C=C(F)C(C#N)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 HBBURBVOOIZAEO-XMMPIXPASA-N 0.000 claims description 2
- QSUJYAYZUAGHMC-WIOPSUGQSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3r)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-WIOPSUGQSA-N 0.000 claims description 2
- SYKRLDPZXIDMRJ-WZONZLPQSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3r)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-WZONZLPQSA-N 0.000 claims description 2
- QSUJYAYZUAGHMC-DHLKQENFSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3s)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-DHLKQENFSA-N 0.000 claims description 2
- SYKRLDPZXIDMRJ-FDDCHVKYSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3s)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-FDDCHVKYSA-N 0.000 claims description 2
- LZHGVCWCMKIINY-DEOSSOPVSA-N n-[(s)-(3-chloro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 LZHGVCWCMKIINY-DEOSSOPVSA-N 0.000 claims description 2
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- VSSSIAXNZPSODL-CZSZKKDXSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s,4r)-2-(hydroxymethyl)oxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(N[C@H]2C[C@@H](CO)OCC2)=N2)C2=C1 VSSSIAXNZPSODL-CZSZKKDXSA-N 0.000 claims description 2
- WEZUSONGOXQEOY-ANJVHQHFSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-[(2r,4s)-4-fluoropyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H]([C@@H]1NC[C@@H](F)C1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 WEZUSONGOXQEOY-ANJVHQHFSA-N 0.000 claims description 2
- KJYWWRQXFYFUCA-ZSEKCTLFSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s)-1-hydroxypropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C=1([C@@H](NC(=O)C=2C=CC3=CN=C(N=C3C=2)N[C@H](CO)C)C=2C=C(F)C(Cl)=CC=2)C=NN(C)C=1 KJYWWRQXFYFUCA-ZSEKCTLFSA-N 0.000 claims description 2
- FWSWGJRTWXRQJN-SKPFHBQLSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s,4s)-2-(hydroxymethyl)oxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@@H]2C[C@@H](CO)OCC2)=N2)C2=C1 FWSWGJRTWXRQJN-SKPFHBQLSA-N 0.000 claims description 2
- RYAVEUFXJVCQNW-XJUOHMSHSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3r,4r)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@H]2[C@H](COCC2)F)=N2)C2=C1 RYAVEUFXJVCQNW-XJUOHMSHSA-N 0.000 claims description 2
- RYAVEUFXJVCQNW-FUDKSRODSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3r,4s)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@@H]2[C@H](COCC2)F)=N2)C2=C1 RYAVEUFXJVCQNW-FUDKSRODSA-N 0.000 claims description 2
- RYAVEUFXJVCQNW-XPNTWCBSSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3s,4r)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@H]2[C@@H](COCC2)F)=N2)C2=C1 RYAVEUFXJVCQNW-XPNTWCBSSA-N 0.000 claims description 2
- RYAVEUFXJVCQNW-GIWBLDEGSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3s,4s)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@@H]2[C@@H](COCC2)F)=N2)C2=C1 RYAVEUFXJVCQNW-GIWBLDEGSA-N 0.000 claims description 2
- BJQJOYNOELTEHJ-CHVDNLQBSA-N n-[(s)-(4-chloro-3-fluorophenyl)-[(2r,5r)-5-methylpyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound N1[C@H](C)CC[C@@H]1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 BJQJOYNOELTEHJ-CHVDNLQBSA-N 0.000 claims description 2
- IOOCGMZCMZXLSH-OPURJYLOSA-N n-[(s)-(4-chloro-3-fluorophenyl)-[(2s)-pyrrolidin-2-yl]methyl]-2-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C([C@H]1[C@@H](NC(=O)C=2C=CC3=CN=C(N=C3C=2)N[C@@H](C)C(F)(F)F)C=2C=C(F)C(Cl)=CC=2)CCN1 IOOCGMZCMZXLSH-OPURJYLOSA-N 0.000 claims description 2
- ILXGLHJWTMZTDE-RPWUZVMVSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2r)-1-methylpyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound CN1CCC[C@@H]1[C@H](C=1C=C(F)C(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 ILXGLHJWTMZTDE-RPWUZVMVSA-N 0.000 claims description 2
- WPDRHVKUBYGIJD-GMAHTHKFSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2s)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3N=C(NC4CCOCC4)N=CC3=CC=2)[C@H]2NCCC2)=C1 WPDRHVKUBYGIJD-GMAHTHKFSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 210000000496 pancreas Anatomy 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 208000000649 small cell carcinoma Diseases 0.000 claims description 2
- 208000001608 teratocarcinoma Diseases 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- 238000004806 packaging method and process Methods 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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| BR112014002675A2 (pt) | 2011-08-04 | 2017-02-21 | Array Biopharma Inc | "quinazolina como inibidores de serina/treonina quinase, seus usos, e composição" |
| PL2820009T3 (pl) | 2012-03-01 | 2018-09-28 | Array Biopharma, Inc. | Inhibitory kinaz serynowo/treoninowych |
| CA2882750A1 (en) * | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
| CN104755478B (zh) | 2012-10-16 | 2017-10-10 | 霍夫曼-拉罗奇有限公司 | 丝氨酸/苏氨酸激酶抑制剂 |
| CN103254142B (zh) * | 2013-04-26 | 2015-10-28 | 浙江工业大学 | 4-[4-(2-取代氨基乙酰氨基)苯胺基]喹唑啉类衍生物及制备和应用 |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| CR20160309A (es) | 2013-12-06 | 2016-08-25 | Genentech Inc | Inhibidores de serina/treonina cinasa |
| JP6487925B2 (ja) | 2013-12-30 | 2019-03-20 | ジェネンテック， インコーポレイテッド | セリン／トレオニンキナーゼ阻害剤 |
| WO2015103137A1 (en) | 2013-12-30 | 2015-07-09 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| WO2015154064A2 (en) | 2014-04-04 | 2015-10-08 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| MX2018012471A (es) | 2016-04-15 | 2019-02-21 | Genentech Inc | Metodos de diagnostico y terapeuticos para el cancer. |
| TW202428305A (zh) | 2017-09-08 | 2024-07-16 | 美商建南德克公司 | 癌症之診斷及治療方法 |
| US20210008047A1 (en) | 2018-02-13 | 2021-01-14 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| US11447493B2 (en) | 2018-05-02 | 2022-09-20 | Kinnate Biopharma Inc. | Inhibitors of cyclin-dependent kinases |
| SG11202013175SA (en) | 2018-06-29 | 2021-01-28 | Kinnate Biopharma Inc | Inhibitors of cyclin-dependent kinases |
| MX2021005047A (es) | 2018-10-31 | 2021-09-08 | Gilead Sciences Inc | Compuestos de 6-azabenzimidazol sustituidos como inhibidores de hpk1. |
| CN117105933A (zh) | 2018-10-31 | 2023-11-24 | 吉利德科学公司 | 具有hpk1抑制活性的取代的6-氮杂苯并咪唑化合物 |
| TWI826690B (zh) | 2019-05-23 | 2023-12-21 | 美商基利科學股份有限公司 | 經取代之烯吲哚酮化物及其用途 |
| JP2023502857A (ja) | 2019-10-25 | 2023-01-26 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｌｒｒｋ２阻害薬としてのｎ－（ヘテロアリール）キナゾリン－２－アミン誘導体、医薬組成物及びその使用 |
| CN115448864B (zh) * | 2022-08-26 | 2023-12-22 | 上海方予健康医药科技有限公司 | 3-氟-3-（1-羟乙基）吡咯烷-1-羧酸叔丁酯的制备方法 |
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| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| CN1328277C (zh) | 1996-12-05 | 2007-07-25 | 安姆根有限公司 | 取代的嘧啶酮和吡啶酮化合物和它们的应用 |
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| CN1438890A (zh) | 2000-02-25 | 2003-08-27 | 弗·哈夫曼-拉罗切有限公司 | 腺苷受体调制剂 |
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| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
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| WO2004007468A1 (en) | 2002-07-15 | 2004-01-22 | Merck & Co., Inc. | Piperidino pyrimidine dipeptidyl peptidase inhibitors for the treatment of diabetes |
| TW200533357A (en) | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
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| US7572809B2 (en) | 2005-12-19 | 2009-08-11 | Hoffmann-La Roche Inc. | Isoquinoline aminopyrazole derivatives |
| ES2353437T3 (es) | 2006-02-16 | 2011-03-02 | Schering Corporation | Derivados de pirrolidina como inhibidores de erk. |
| US7998978B2 (en) | 2006-05-01 | 2011-08-16 | Pfizer Inc. | Substituted 2-amino-fused heterocyclic compounds |
| DE102006035202A1 (de) | 2006-07-29 | 2008-01-31 | Lanxess Deutschland Gmbh | Konservierungsmittel auf Basis von Carbonsäureanhydriden |
| KR20090052884A (ko) | 2006-08-23 | 2009-05-26 | 화이자 프로덕츠 인크. | Ｇｓｋ-3 억제제로서의 피리미돈 화합물 |
| WO2008039882A1 (en) | 2006-09-30 | 2008-04-03 | Sanofi-Aventis U.S. Llc | A combination of niacin and a prostaglandin d2 receptor antagonist |
| WO2008079933A2 (en) | 2006-12-22 | 2008-07-03 | Novartis Ag | Heteroaryl-heteroaryl compounds as cdk inhibitors for the treatment of cancer, inflammation and viral infections |
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| CN101902912A (zh) | 2007-11-06 | 2010-12-01 | 纳幕尔杜邦公司 | 杀真菌杂环胺 |
| WO2009146034A2 (en) * | 2008-03-31 | 2009-12-03 | Takeda Pharmaceutical Company Limited | Mapk/erk kinase inhibitors and methods of use thereof |
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| BR112014002675A2 (pt) | 2011-08-04 | 2017-02-21 | Array Biopharma Inc | "quinazolina como inibidores de serina/treonina quinase, seus usos, e composição" |
| PL2820009T3 (pl) | 2012-03-01 | 2018-09-28 | Array Biopharma, Inc. | Inhibitory kinaz serynowo/treoninowych |
| CA2882750A1 (en) | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
-
2012
- 2012-08-03 BR BR112014002675A patent/BR112014002675A2/pt not_active IP Right Cessation
- 2012-08-03 CA CA2844058A patent/CA2844058A1/en not_active Abandoned
- 2012-08-03 RU RU2014108140/04A patent/RU2014108140A/ru not_active Application Discontinuation
- 2012-08-03 KR KR1020147005731A patent/KR101979042B1/ko not_active Expired - Fee Related
- 2012-08-03 WO PCT/US2012/049551 patent/WO2013020062A1/en not_active Ceased
- 2012-08-03 MX MX2014001389A patent/MX340756B/es active IP Right Grant
- 2012-08-03 ES ES12769775.3T patent/ES2552989T3/es active Active
- 2012-08-03 JP JP2014524111A patent/JP6097289B2/ja active Active
- 2012-08-03 US US14/237,143 patent/US9187462B2/en active Active
- 2012-08-03 CN CN201280049268.3A patent/CN103958502B/zh active Active
- 2012-08-03 EP EP12769775.3A patent/EP2739618B1/en active Active
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