JP2019526550A5 - - Google Patents
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- Publication number
- JP2019526550A5 JP2019526550A5 JP2019508173A JP2019508173A JP2019526550A5 JP 2019526550 A5 JP2019526550 A5 JP 2019526550A5 JP 2019508173 A JP2019508173 A JP 2019508173A JP 2019508173 A JP2019508173 A JP 2019508173A JP 2019526550 A5 JP2019526550 A5 JP 2019526550A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyridin
- amino
- pyrimidin
- benzamide
- 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 nitro, carboxy Chemical group 0.000 claims description 1565
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 567
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 236
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 152
- 150000003839 salts Chemical class 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 132
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 102
- NYTBSQABQFKJQV-UHFFFAOYSA-N C=CC(N(CC1)CC1N1C(N)=CN=C1)=O Chemical compound C=CC(N(CC1)CC1N1C(N)=CN=C1)=O NYTBSQABQFKJQV-UHFFFAOYSA-N 0.000 claims description 85
- QFMZEZOREOKKDU-UHFFFAOYSA-N C=CC(N(CCC1)CC1N1C(N)=CN=C1)=O Chemical compound C=CC(N(CCC1)CC1N1C(N)=CN=C1)=O QFMZEZOREOKKDU-UHFFFAOYSA-N 0.000 claims description 66
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 64
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 40
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 13
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 13
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- SAOVSRNDELSDHS-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1 SAOVSRNDELSDHS-UHFFFAOYSA-N 0.000 claims description 10
- 230000035772 mutation Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- FWAYNVADYPHGBQ-UHFFFAOYSA-N COC1=CC(OC(C=C2)=CC(Cl)=C2N2C=NC(N)=C2)=NC=C1 Chemical compound COC1=CC(OC(C=C2)=CC(Cl)=C2N2C=NC(N)=C2)=NC=C1 FWAYNVADYPHGBQ-UHFFFAOYSA-N 0.000 claims description 8
- IZTGQUSUIGFUDG-UHFFFAOYSA-N COC1=CC(OC(C=C2)=CC(F)=C2N2C=NC(N)=C2)=NC=C1 Chemical compound COC1=CC(OC(C=C2)=CC(F)=C2N2C=NC(N)=C2)=NC=C1 IZTGQUSUIGFUDG-UHFFFAOYSA-N 0.000 claims description 8
- WKSFFOQTRUONNU-UHFFFAOYSA-N COC1=CC(OC(C=C2)=CC=C2N2C=NC(N)=C2)=NC=C1 Chemical compound COC1=CC(OC(C=C2)=CC=C2N2C=NC(N)=C2)=NC=C1 WKSFFOQTRUONNU-UHFFFAOYSA-N 0.000 claims description 8
- CTKHBWMFEGZGDS-UHFFFAOYSA-N COC1=CC(OC(C=C2)=CN=C2N2C=NC(N)=C2)=NC=C1 Chemical compound COC1=CC(OC(C=C2)=CN=C2N2C=NC(N)=C2)=NC=C1 CTKHBWMFEGZGDS-UHFFFAOYSA-N 0.000 claims description 8
- RRPGFYPGYUBQPQ-UHFFFAOYSA-N COC1=CC(OC(C=CC(N2C=NC(N)=C2)=C2)=C2Cl)=NC=C1 Chemical compound COC1=CC(OC(C=CC(N2C=NC(N)=C2)=C2)=C2Cl)=NC=C1 RRPGFYPGYUBQPQ-UHFFFAOYSA-N 0.000 claims description 8
- HKTAMRDUSDAVQO-UHFFFAOYSA-N COC1=CC(OC(C=CC(N2C=NC(N)=C2)=C2)=C2F)=NC=C1 Chemical compound COC1=CC(OC(C=CC(N2C=NC(N)=C2)=C2)=C2F)=NC=C1 HKTAMRDUSDAVQO-UHFFFAOYSA-N 0.000 claims description 8
- STHBEEHRUWADBE-UHFFFAOYSA-N COC1=CC(OC(N=C2)=CC=C2N2C=NC(N)=C2)=NC=C1 Chemical compound COC1=CC(OC(N=C2)=CC=C2N2C=NC(N)=C2)=NC=C1 STHBEEHRUWADBE-UHFFFAOYSA-N 0.000 claims description 8
- DEYUDNVIYCNDEQ-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC(C(F)(F)F)=C1 DEYUDNVIYCNDEQ-UHFFFAOYSA-N 0.000 claims description 8
- QNINXWJPADHUAR-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC(C2CC2)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC(C2CC2)=C1 QNINXWJPADHUAR-UHFFFAOYSA-N 0.000 claims description 8
- BYCCKMMMSAONAD-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(Cl)=C1OC1=NC=CC=C1 BYCCKMMMSAONAD-UHFFFAOYSA-N 0.000 claims description 8
- LNHWZVNBIPPIDR-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC(C(F)(F)F)=C1 LNHWZVNBIPPIDR-UHFFFAOYSA-N 0.000 claims description 8
- OVXQSVDJNMMFCK-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC(C2CC2)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC(C2CC2)=C1 OVXQSVDJNMMFCK-UHFFFAOYSA-N 0.000 claims description 8
- SIUODXZDHGKCTO-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC(F)=C1OC1=NC=CC=C1 SIUODXZDHGKCTO-UHFFFAOYSA-N 0.000 claims description 8
- SWRWTWGJTKGYQE-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC(C(F)(F)F)=C1 SWRWTWGJTKGYQE-UHFFFAOYSA-N 0.000 claims description 8
- APMJWNDTRJEXRY-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC(C2CC2)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC(C2CC2)=C1 APMJWNDTRJEXRY-UHFFFAOYSA-N 0.000 claims description 8
- QRSCCMBNFYAFBC-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC(C(F)(F)F)=C1 QRSCCMBNFYAFBC-UHFFFAOYSA-N 0.000 claims description 8
- WKQFQSMYCVDJMB-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC(C2CC2)=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC(C2CC2)=C1 WKQFQSMYCVDJMB-UHFFFAOYSA-N 0.000 claims description 8
- FKKNUMGBHVAOLL-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC=C1 Chemical compound NC(N=C1)=CN1C(C=C1)=NC=C1OC1=NC=CC=C1 FKKNUMGBHVAOLL-UHFFFAOYSA-N 0.000 claims description 8
- HESXTZIFXAOSML-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C(F)(F)F)=C1)=C1)=C1Cl Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C(F)(F)F)=C1)=C1)=C1Cl HESXTZIFXAOSML-UHFFFAOYSA-N 0.000 claims description 8
- MIWCDIYCATURNL-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C(F)(F)F)=C1)=C1)=C1F Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C(F)(F)F)=C1)=C1)=C1F MIWCDIYCATURNL-UHFFFAOYSA-N 0.000 claims description 8
- CBECHCGROWIWOJ-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C2CC2)=C1)=C1)=C1Cl Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C2CC2)=C1)=C1)=C1Cl CBECHCGROWIWOJ-UHFFFAOYSA-N 0.000 claims description 8
- ILQZRHCHUPSAPQ-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C2CC2)=C1)=C1)=C1F Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC(C2CC2)=C1)=C1)=C1F ILQZRHCHUPSAPQ-UHFFFAOYSA-N 0.000 claims description 8
- JXRQVQQRTKIYDH-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC=C1)=C1)=C1Cl Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC=C1)=C1)=C1Cl JXRQVQQRTKIYDH-UHFFFAOYSA-N 0.000 claims description 8
- IPMHDEIWWLLBEG-UHFFFAOYSA-N NC(N=C1)=CN1C(C=CC(OC1=NC=CC=C1)=C1)=C1F Chemical compound NC(N=C1)=CN1C(C=CC(OC1=NC=CC=C1)=C1)=C1F IPMHDEIWWLLBEG-UHFFFAOYSA-N 0.000 claims description 8
- BFSHEWCCSZGCRU-UHFFFAOYSA-N NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC(C(F)(F)F)=C1 BFSHEWCCSZGCRU-UHFFFAOYSA-N 0.000 claims description 8
- YVQNWZLYRDRRJG-UHFFFAOYSA-N NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC(C2CC2)=C1 Chemical compound NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC(C2CC2)=C1 YVQNWZLYRDRRJG-UHFFFAOYSA-N 0.000 claims description 8
- UWABUWLONJRUAS-UHFFFAOYSA-N NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC=C1 Chemical compound NC(N=C1)=CN1C(C=N1)=CC=C1OC1=NC=CC=C1 UWABUWLONJRUAS-UHFFFAOYSA-N 0.000 claims description 8
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 8
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- KAOGOFCVBQPTIX-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1C(F)(F)F Chemical compound NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1C(F)(F)F KAOGOFCVBQPTIX-UHFFFAOYSA-N 0.000 claims description 6
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000012472 biological sample Substances 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
- 239000012434 nucleophilic reagent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 4
- VKFHZXBIAJSFFN-UHFFFAOYSA-N C=CC(NC1=CC(C2=C3N=CN=CC3=CC(C3=CC=CC=C3NC3=CC(C(F)(F)F)=CC=C3)=C2)=CC=C1)=O Chemical compound C=CC(NC1=CC(C2=C3N=CN=CC3=CC(C3=CC=CC=C3NC3=CC(C(F)(F)F)=CC=C3)=C2)=CC=C1)=O VKFHZXBIAJSFFN-UHFFFAOYSA-N 0.000 claims description 4
- FBWMYSAXEVAGHE-UHFFFAOYSA-N COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC(C(F)(F)F)=C1 Chemical compound COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC(C(F)(F)F)=C1 FBWMYSAXEVAGHE-UHFFFAOYSA-N 0.000 claims description 4
- KRLJWBCPVMJTFU-UHFFFAOYSA-N COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC=C1 Chemical compound COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC=C1 KRLJWBCPVMJTFU-UHFFFAOYSA-N 0.000 claims description 4
- RXXGUVFWZYLCKS-UHFFFAOYSA-N COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC=C1F Chemical compound COC(C=C(C=C1)N2C=NC(N)=C2)=C1OC1=NC=CC=C1F RXXGUVFWZYLCKS-UHFFFAOYSA-N 0.000 claims description 4
- XUNMMVLRTDNASQ-UHFFFAOYSA-N NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1F Chemical compound NC(N=C1)=CN1C(C=C1)=CC=C1OC1=NC=CC=C1F XUNMMVLRTDNASQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- JJXZIAQFAIZEOG-UHFFFAOYSA-N 1-[3-(2-amino-6-pyridin-3-ylquinazolin-8-yl)piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=CC=1)C1CN(CCC1)C(C=C)=O JJXZIAQFAIZEOG-UHFFFAOYSA-N 0.000 claims description 2
- UZNYBTOHYFPEAB-UHFFFAOYSA-N 1-[3-(2-amino-8-phenylpurin-9-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=C2N=C(N(C2=N1)C1CN(CC1)C(C=C)=O)C1=CC=CC=C1 UZNYBTOHYFPEAB-UHFFFAOYSA-N 0.000 claims description 2
- XNPLZLPEMGKTGP-UHFFFAOYSA-N 1-[3-(4-amino-6-phenylquinazolin-8-yl)piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=NC2=C(C=C(C=C12)C1=CC=CC=C1)C1CN(CCC1)C(C=C)=O XNPLZLPEMGKTGP-UHFFFAOYSA-N 0.000 claims description 2
- YOTUNBXRJFBGGP-UHFFFAOYSA-N 1-[3-(6-phenylquinazolin-8-yl)piperidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CCC1)C(C=C)=O YOTUNBXRJFBGGP-UHFFFAOYSA-N 0.000 claims description 2
- HVXLKTICADBPMX-UHFFFAOYSA-N 1-[3-(6-phenylquinazolin-8-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O HVXLKTICADBPMX-UHFFFAOYSA-N 0.000 claims description 2
- YHLZOPLNXWMVQC-UHFFFAOYSA-N 1-[3-(6-pyridin-3-ylquinazolin-8-yl)piperidin-1-yl]prop-2-en-1-one Chemical compound N1=CC(=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CCC1)C(C=C)=O YHLZOPLNXWMVQC-UHFFFAOYSA-N 0.000 claims description 2
- WEWORHFIMGFXNS-UHFFFAOYSA-N 1-[3-(6-pyridin-3-ylquinazolin-8-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound N1=CC(=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O WEWORHFIMGFXNS-UHFFFAOYSA-N 0.000 claims description 2
- WJTHHWBYKWSMCO-UHFFFAOYSA-N 1-[3-(8-phenylpurin-9-yl)piperidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC=CC=C1)C=1N(C2=NC=NC=C2N=1)C1CN(CCC1)C(C=C)=O WJTHHWBYKWSMCO-UHFFFAOYSA-N 0.000 claims description 2
- ANWFFKICPOYEDT-UHFFFAOYSA-N 1-[3-(8-phenylpurin-9-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC=CC=C1)C=1N(C2=NC=NC=C2N=1)C1CN(CC1)C(C=C)=O ANWFFKICPOYEDT-UHFFFAOYSA-N 0.000 claims description 2
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| WO2022140246A1 (en) | 2020-12-21 | 2022-06-30 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| TW202241889A (zh) | 2020-12-23 | 2022-11-01 | 美商雅捷可斯治療公司 | 作為ｊａｋ２抑制劑之６－雜芳基氧基苯并咪唑及氮雜苯并咪唑 |
| CN113603695B (zh) * | 2021-08-05 | 2022-06-14 | 青岛恒宁生物科技有限公司 | 一种取代的嘧啶胺类化合物或其作为农药可接受的盐、组合物及其用途 |
| US12162881B2 (en) | 2021-11-09 | 2024-12-10 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of JAK2 |
| AU2022388555A1 (en) | 2021-11-09 | 2024-05-02 | Ajax Therapeutics, Inc. | 6-he tero aryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| CN119841806A (zh) * | 2023-10-16 | 2025-04-18 | 中国医学科学院药物研究所 | 多取代的喹唑啉类化合物及其制备方法、用途和药物组合物 |
| WO2025235874A1 (en) * | 2024-05-10 | 2025-11-13 | Schrödinger, Inc. | Heterocyclics as egfr inhibitors |
Family Cites Families (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB587936A (en) | 1944-09-05 | 1947-05-09 | Francis Henry Swinden Curd | New quinazoline derivatives |
| GB8515934D0 (en) * | 1985-06-24 | 1985-07-24 | Janssen Pharmaceutica Nv | (4-piperidinomethyl and-hetero)purines |
| US5052558A (en) | 1987-12-23 | 1991-10-01 | Entravision, Inc. | Packaged pharmaceutical product |
| US5033252A (en) | 1987-12-23 | 1991-07-23 | Entravision, Inc. | Method of packaging and sterilizing a pharmaceutical product |
| US5323907A (en) | 1992-06-23 | 1994-06-28 | Multi-Comp, Inc. | Child resistant package assembly for dispensing pharmaceutical medications |
| KR20040068613A (ko) | 1994-03-25 | 2004-07-31 | 이소테크니카 인코포레이티드 | 중수소화된 화합물 이를 포함하는 고혈압 치료용 조성물 |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| CN1067070C (zh) | 1996-02-12 | 2001-06-13 | 新泽西州州立大学(拉特格斯) | 用作拓扑异构酶抑制剂的甲氧檗因类似物 |
| KR19990082463A (ko) | 1996-02-13 | 1999-11-25 | 돈 리사 로얄 | 혈관 내피 성장 인자 억제제로서의 퀴나졸린유도체 |
| AU719327B2 (en) | 1996-03-05 | 2000-05-04 | Astrazeneca Ab | 4-anilinoquinazoline derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| WO1999035147A1 (en) | 1998-01-05 | 1999-07-15 | Eisai Co., Ltd. | Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes |
| JP3990061B2 (ja) * | 1998-01-05 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | プリン誘導体および糖尿病の予防・治療剤としてのアデノシンａ２受容体拮抗剤 |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| SK288365B6 (sk) | 1999-02-10 | 2016-07-01 | Astrazeneca Ab | Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy |
| ES2246867T3 (es) * | 1999-07-02 | 2006-03-01 | Eisai Co., Ltd. | Compuestos de imidazol condensados y medicamentos contra la diabetes mellitus. |
| AU7031500A (en) | 1999-09-23 | 2001-04-24 | Astrazeneca Ab | Therapeutic quinazoline compounds |
| EP1289952A1 (en) | 2000-05-31 | 2003-03-12 | AstraZeneca AB | Indole derivatives with vascular damaging activity |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| WO2002008213A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| MXPA02012905A (es) | 2000-07-07 | 2004-07-30 | Angiogene Pharm Ltd | Derivados de colquinol como agentes de dano vascular.. |
| UA80295C2 (en) * | 2002-09-06 | 2007-09-10 | Biogen Inc | Pyrazolopyridines and using the same |
| EP1601678A2 (en) | 2003-03-13 | 2005-12-07 | Synta Pharmaceuticals Corporation | Fused pyrrole compounds |
| WO2005032481A2 (en) * | 2003-09-30 | 2005-04-14 | Scios Inc. | Quinazoline derivatives as medicaments |
| AU2005298637B8 (en) | 2004-10-29 | 2012-12-06 | Janssen Sciences Ireland Uc | HIV inhibiting bicyclic pyrimidine derivatives |
| CR9465A (es) * | 2005-03-25 | 2008-06-19 | Surface Logix Inc | Compuestos mejorados farmacocineticamente |
| GB0526246D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| TW200808739A (en) | 2006-04-06 | 2008-02-16 | Novartis Vaccines & Diagnostic | Quinazolines for PDK1 inhibition |
| TWI389893B (zh) | 2007-07-06 | 2013-03-21 | Astellas Pharma Inc | 二（芳胺基）芳基化合物 |
| WO2009131173A1 (ja) * | 2008-04-23 | 2009-10-29 | 協和発酵キリン株式会社 | 2-アミノキナゾリン誘導体 |
| US8252791B2 (en) * | 2008-08-13 | 2012-08-28 | Jenrin Discovery, Inc. | Purine compounds as cannabinoid receptor blockers |
| WO2010056758A1 (en) * | 2008-11-12 | 2010-05-20 | Yangbo Feng | Quinazoline derivatives as kinase inhibitors |
| JP5918693B2 (ja) | 2009-05-05 | 2016-05-18 | ダナ ファーバー キャンサー インスティテュート インコーポレイテッド | Ｅｇｆｒ阻害剤及び疾患の治療方法 |
| KR101906568B1 (ko) * | 2009-10-07 | 2018-10-10 | 슬로안-케테링인스티튜트퍼캔서리서치 | Ｈｓｐ９０ 저해제로서 유용한 퓨린 유도체 |
| US7718662B1 (en) * | 2009-10-12 | 2010-05-18 | Pharmacyclics, Inc. | Pyrazolo-pyrimidine inhibitors of bruton's tyrosine kinase |
| WO2011079231A1 (en) | 2009-12-23 | 2011-06-30 | Gatekeeper Pharmaceutical, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
| WO2011106168A1 (en) | 2010-02-24 | 2011-09-01 | Dcam Pharma Inc | Purine compounds for treating autoimmune and demyelinating diseases |
| FR2959510B1 (fr) | 2010-04-28 | 2013-04-26 | Centre Nat Rech Scient | Derives de pyrido[3,2-d]pyrimidine, leurs procedes de preparation et leurs utilisations therapeutiques |
| CN102260263A (zh) * | 2010-05-26 | 2011-11-30 | 四川大学 | 一类二苯胺基嘌呤衍生物及制备方法和医药用途 |
| WO2012135801A1 (en) | 2011-04-01 | 2012-10-04 | University Of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| WO2013005157A1 (en) * | 2011-07-05 | 2013-01-10 | Lupin Limited | Sulfone derivatives and their use as pkm2 modulators for the treatment of cancer |
| WO2013013031A1 (en) | 2011-07-19 | 2013-01-24 | Abbvie Inc. | Pyridazino [4, 5 -d] pyrimidin- (6h) -one inhibitors of wee - 1 kinase |
| ME02887B (me) | 2011-07-27 | 2018-04-20 | Astrazeneca Ab | 2-(2,4,5-supstituisani-anilino) pirimidinski derivati kao egfr modulatori korisni za tretman raka |
| JP6002223B2 (ja) | 2011-08-26 | 2016-10-05 | ニューファーマ， インコーポレイテッド | 特定の化学的実体、組成物、および方法 |
| US9518029B2 (en) * | 2011-09-14 | 2016-12-13 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| CN104203924B (zh) | 2012-01-13 | 2019-06-11 | 艾森生物科学公司 | 杂环化合物及其作为抗癌药的用途 |
| WO2013118817A1 (ja) * | 2012-02-07 | 2013-08-15 | 大鵬薬品工業株式会社 | キノリルピロロピリミジン化合物又はその塩 |
| TW201348226A (zh) | 2012-02-28 | 2013-12-01 | Amgen Inc | 作為ｐｉｍ抑制劑之醯胺 |
| RU2679130C2 (ru) | 2012-07-11 | 2019-02-06 | Блюпринт Медсинс Корпорейшн | Ингибиторы рецептора фактора роста фибробластов |
| GB201216017D0 (en) | 2012-09-07 | 2012-10-24 | Cancer Rec Tech Ltd | Inhibitor compounds |
| TW201427958A (zh) | 2012-09-14 | 2014-07-16 | Univ Nat Yang Ming | 芳基胺取代之嘧啶及喹唑啉及其作為抗癌藥物之用途 |
| WO2014052699A1 (en) * | 2012-09-28 | 2014-04-03 | Cephalon, Inc. | Azaquinazoline inhibitors of atypical protein kinase c |
| CN103864792B (zh) * | 2012-12-12 | 2017-01-18 | 山东亨利医药科技有限责任公司 | 作为酪氨酸激酶抑制剂的含氮并环类化合物 |
| CN103936742B (zh) | 2013-01-17 | 2017-05-03 | 程鹏 | 含嘌呤基的新型pi3k抑制剂及其制备方法和应用 |
| US9708326B2 (en) | 2013-02-25 | 2017-07-18 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| CA2903901A1 (en) | 2013-03-05 | 2014-09-12 | Merck Patent Gmbh | 9-(aryl or heteroaryl)-2-(pyrazolyl, pyrrolidinyl or cyclopentyl)aminopurine derivatives as anticancer agents |
| SI2964638T1 (sl) | 2013-03-06 | 2017-11-30 | Astrazeneca Ab | Kinazolinski inhibitorji aktiviranja mutantnih oblik receptorja epidermalnega rastnega faktorja |
| EP2994471B1 (en) | 2013-05-06 | 2017-05-17 | Merck Patent GmbH | Macrocycles as kinase inhibitors |
| CN103554038B (zh) * | 2013-06-19 | 2015-10-14 | 云南大学 | 多卤代苯腈喹唑啉酮化合物及其制备方法和用途 |
| DK3019496T3 (da) | 2013-07-11 | 2019-12-09 | Acea Therapeutics Inc | Pyrimidinderivater som kinaseinhibitorer |
| EP2947086B1 (en) * | 2013-08-12 | 2018-01-03 | Taiho Pharmaceutical Co., Ltd. | Novel fused pyrimidine compound or salt thereof |
| PH12019500143B1 (en) | 2013-08-23 | 2023-03-24 | Neupharma Inc | Certain chemical entities, compositions, and methods |
| CA2922044A1 (en) * | 2013-10-18 | 2015-05-14 | Medivation Technologies, Inc. | Pyrazolo-, imidazolo- and pyrrolo-pyridine or -pyrimidine derivatives as inhibitors o brutons kinase (btk) |
| GB201404987D0 (en) * | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| US9840520B2 (en) | 2014-05-14 | 2017-12-12 | The Regents Of The University Of Colorado, A Body Corporate | Heterocyclic hydroxamic acids as protein deacetylase inhibitors and dual protein deacetylase-protein kinase inhibitors and methods of use thereof |
| CN104086551B (zh) | 2014-06-06 | 2016-09-21 | 人福医药集团股份公司 | 化合物及其制备方法和用途 |
| WO2015193740A2 (en) | 2014-06-17 | 2015-12-23 | Acerta Pharma B.V. | Therapeutic combinations of a btk inhibitor, a pi3k inhibitor and/or a jak-2 inhibitor |
| CN105315283A (zh) * | 2014-07-22 | 2016-02-10 | 成都贝斯凯瑞生物科技有限公司 | 一种Bruton酪氨酸激酶抑制剂 |
| EP3174539A4 (en) * | 2014-08-01 | 2017-12-13 | Pharmacyclics, LLC | Inhibitors of bruton's tyrosine kinase |
| US10435402B2 (en) * | 2015-01-08 | 2019-10-08 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| CN105837576B (zh) | 2015-01-14 | 2019-03-26 | 湖北生物医药产业技术研究院有限公司 | Btk抑制剂 |
| AU2016220219B2 (en) | 2015-02-17 | 2020-05-14 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| CN105777759B (zh) * | 2016-04-29 | 2018-01-26 | 杭州和正医药有限公司 | 一种布鲁顿酪氨酸激酶抑制剂 |
| WO2018035061A1 (en) | 2016-08-15 | 2018-02-22 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
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