CA3033370A1 - Certain chemical entities, compositions, and methods - Google Patents
Certain chemical entities, compositions, and methods Download PDFInfo
- Publication number
- CA3033370A1 CA3033370A1 CA3033370A CA3033370A CA3033370A1 CA 3033370 A1 CA3033370 A1 CA 3033370A1 CA 3033370 A CA3033370 A CA 3033370A CA 3033370 A CA3033370 A CA 3033370A CA 3033370 A1 CA3033370 A1 CA 3033370A1
- Authority
- CA
- Canada
- Prior art keywords
- pyrimidin
- pyridin
- amino
- phenyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims description 56
- 150000005829 chemical entities Chemical class 0.000 title abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 37
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
- 201000011510 cancer Diseases 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims description 286
- -1 nitro, carboxy Chemical group 0.000 claims description 240
- 229910052739 hydrogen Inorganic materials 0.000 claims description 163
- 239000001257 hydrogen Substances 0.000 claims description 151
- 150000003839 salts Chemical class 0.000 claims description 151
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 125000001072 heteroaryl group Chemical group 0.000 claims description 137
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 134
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 111
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 110
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 102
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
- 125000005843 halogen group Chemical group 0.000 claims description 87
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 82
- 125000003107 substituted aryl group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 58
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 48
- 125000004043 oxo group Chemical group O=* 0.000 claims description 47
- 125000002252 acyl group Chemical group 0.000 claims description 45
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 44
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 44
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 42
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 38
- 125000004104 aryloxy group Chemical group 0.000 claims description 37
- 102200048928 rs121434568 Human genes 0.000 claims description 36
- 102200048955 rs121434569 Human genes 0.000 claims description 36
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 35
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 34
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 32
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 32
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 29
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 25
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 239000000725 suspension Substances 0.000 claims description 15
- 230000035772 mutation Effects 0.000 claims description 14
- 239000012038 nucleophile Substances 0.000 claims description 14
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 201000002510 thyroid cancer Diseases 0.000 claims description 12
- 208000032839 leukemia Diseases 0.000 claims description 11
- 235000018102 proteins Nutrition 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 10
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 10
- 206010009944 Colon cancer Diseases 0.000 claims description 10
- 208000017604 Hodgkin disease Diseases 0.000 claims description 10
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 10
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 10
- 206010033128 Ovarian cancer Diseases 0.000 claims description 10
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
- 208000009956 adenocarcinoma Diseases 0.000 claims description 10
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 239000002775 capsule Substances 0.000 claims description 9
- 230000001684 chronic effect Effects 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 201000009030 Carcinoma Diseases 0.000 claims description 8
- 208000034578 Multiple myelomas Diseases 0.000 claims description 8
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 8
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 8
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- 206010025323 Lymphomas Diseases 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 7
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 201000001441 melanoma Diseases 0.000 claims description 7
- 239000003826 tablet Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 208000000172 Medulloblastoma Diseases 0.000 claims description 6
- 206010027406 Mesothelioma Diseases 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 6
- 150000001805 chlorine compounds Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 239000000829 suppository Substances 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 5
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 5
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
- 201000003076 Angiosarcoma Diseases 0.000 claims description 5
- 206010003571 Astrocytoma Diseases 0.000 claims description 5
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
- 206010004593 Bile duct cancer Diseases 0.000 claims description 5
- 206010005003 Bladder cancer Diseases 0.000 claims description 5
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
- 201000005262 Chondroma Diseases 0.000 claims description 5
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 5
- 208000006332 Choriocarcinoma Diseases 0.000 claims description 5
- 208000009798 Craniopharyngioma Diseases 0.000 claims description 5
- 201000009051 Embryonal Carcinoma Diseases 0.000 claims description 5
- 206010014967 Ependymoma Diseases 0.000 claims description 5
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims description 5
- 208000036566 Erythroleukaemia Diseases 0.000 claims description 5
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 5
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 5
- 208000032612 Glial tumor Diseases 0.000 claims description 5
- 206010018338 Glioma Diseases 0.000 claims description 5
- 208000001258 Hemangiosarcoma Diseases 0.000 claims description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 5
- 208000018142 Leiomyosarcoma Diseases 0.000 claims description 5
- 206010024305 Leukaemia monocytic Diseases 0.000 claims description 5
- 208000007054 Medullary Carcinoma Diseases 0.000 claims description 5
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
- 206010029260 Neuroblastoma Diseases 0.000 claims description 5
- 201000010133 Oligodendroglioma Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 208000007641 Pinealoma Diseases 0.000 claims description 5
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 5
- 201000000582 Retinoblastoma Diseases 0.000 claims description 5
- 201000010208 Seminoma Diseases 0.000 claims description 5
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
- 208000014070 Vestibular schwannoma Diseases 0.000 claims description 5
- 208000008383 Wilms tumor Diseases 0.000 claims description 5
- 208000004064 acoustic neuroma Diseases 0.000 claims description 5
- 208000017733 acquired polycythemia vera Diseases 0.000 claims description 5
- 208000021841 acute erythroid leukemia Diseases 0.000 claims description 5
- 201000007180 bile duct carcinoma Diseases 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 201000001531 bladder carcinoma Diseases 0.000 claims description 5
- 208000003362 bronchogenic carcinoma Diseases 0.000 claims description 5
- 201000010881 cervical cancer Diseases 0.000 claims description 5
- 208000024207 chronic leukemia Diseases 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 208000002445 cystadenocarcinoma Diseases 0.000 claims description 5
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 5
- 125000005959 diazepanyl group Chemical group 0.000 claims description 5
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 5
- 208000037828 epithelial carcinoma Diseases 0.000 claims description 5
- 208000025750 heavy chain disease Diseases 0.000 claims description 5
- 201000002222 hemangioblastoma Diseases 0.000 claims description 5
- 206010024627 liposarcoma Diseases 0.000 claims description 5
- 201000005296 lung carcinoma Diseases 0.000 claims description 5
- 208000037829 lymphangioendotheliosarcoma Diseases 0.000 claims description 5
- 208000012804 lymphangiosarcoma Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 claims description 5
- 206010027191 meningioma Diseases 0.000 claims description 5
- 201000006894 monocytic leukemia Diseases 0.000 claims description 5
- 208000001611 myxosarcoma Diseases 0.000 claims description 5
- 208000025189 neoplasm of testis Diseases 0.000 claims description 5
- 201000008968 osteosarcoma Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 208000004019 papillary adenocarcinoma Diseases 0.000 claims description 5
- 201000010198 papillary carcinoma Diseases 0.000 claims description 5
- 208000024724 pineal body neoplasm Diseases 0.000 claims description 5
- 201000004123 pineal gland cancer Diseases 0.000 claims description 5
- 208000037244 polycythemia vera Diseases 0.000 claims description 5
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 5
- 201000008407 sebaceous adenocarcinoma Diseases 0.000 claims description 5
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 5
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 5
- 201000010965 sweat gland carcinoma Diseases 0.000 claims description 5
- 206010042863 synovial sarcoma Diseases 0.000 claims description 5
- 201000003120 testicular cancer Diseases 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 5
- 230000001093 anti-cancer Effects 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 239000002254 cytotoxic agent Substances 0.000 claims description 4
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 4
- 102000039446 nucleic acids Human genes 0.000 claims description 4
- 108020004707 nucleic acids Proteins 0.000 claims description 4
- 102200048929 rs121913444 Human genes 0.000 claims description 4
- 102200048796 rs28929495 Human genes 0.000 claims description 4
- 102200048979 rs28929495 Human genes 0.000 claims description 4
- 150000003892 tartrate salts Chemical class 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- ZANOPAXJMUQJDY-UHFFFAOYSA-N 1-[3-[5-amino-6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=NC=CC=C1)C1CN(CC1)C(C=C)=O ZANOPAXJMUQJDY-UHFFFAOYSA-N 0.000 claims description 3
- LVVGQWUCDMZJJZ-UHFFFAOYSA-N 1-[3-[6-(2-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O LVVGQWUCDMZJJZ-UHFFFAOYSA-N 0.000 claims description 3
- PNENXYSEHYSAKW-UHFFFAOYSA-N 1-[3-[6-(3-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(C=CC=1OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O PNENXYSEHYSAKW-UHFFFAOYSA-N 0.000 claims description 3
- DJWJGVMGQUPQEK-UHFFFAOYSA-N 1-[3-[6-(3-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC=1C=C(C=CC=1OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O DJWJGVMGQUPQEK-UHFFFAOYSA-N 0.000 claims description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- 206010002412 Angiocentric lymphomas Diseases 0.000 claims description 3
- 208000032568 B-cell prolymphocytic leukaemia Diseases 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 3
- 206010052178 Lymphocytic lymphoma Diseases 0.000 claims description 3
- 201000003791 MALT lymphoma Diseases 0.000 claims description 3
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 3
- YGPABYQIECHROT-UHFFFAOYSA-N N-[3-(6-pyridin-2-ylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound N1=C(C=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O YGPABYQIECHROT-UHFFFAOYSA-N 0.000 claims description 3
- QMBDURQRANLPOF-UHFFFAOYSA-N N-[3-[2-amino-6-(2-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)OC)C=1C=C(C=CC=1)NC(C=C)=O QMBDURQRANLPOF-UHFFFAOYSA-N 0.000 claims description 3
- SAOUKNILOKMLSJ-UHFFFAOYSA-N N-[3-[5-amino-6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=NC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O SAOUKNILOKMLSJ-UHFFFAOYSA-N 0.000 claims description 3
- RDHHNNSMLWSPLA-UHFFFAOYSA-N N-[3-[6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O RDHHNNSMLWSPLA-UHFFFAOYSA-N 0.000 claims description 3
- KSUVZFMEVFWJSA-UHFFFAOYSA-N N-[3-[6-(3-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound COC=1C=C(C=CC=1OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O KSUVZFMEVFWJSA-UHFFFAOYSA-N 0.000 claims description 3
- ASEZWLBRXZBNOS-UHFFFAOYSA-N N-[3-[6-[4-(4-cyanopyridin-2-yl)oxy-2-fluorophenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C1=CC(=NC=C1)OC1=CC(=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)F ASEZWLBRXZBNOS-UHFFFAOYSA-N 0.000 claims description 3
- MBVDKXQEABGHCB-UHFFFAOYSA-N N-[3-[6-[4-(4-cyanopyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C1=CC(=NC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O MBVDKXQEABGHCB-UHFFFAOYSA-N 0.000 claims description 3
- 206010029461 Nodal marginal zone B-cell lymphomas Diseases 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- 206010065857 Primary Effusion Lymphoma Diseases 0.000 claims description 3
- 206010036711 Primary mediastinal large B-cell lymphomas Diseases 0.000 claims description 3
- 208000035416 Prolymphocytic B-Cell Leukemia Diseases 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 201000003444 follicular lymphoma Diseases 0.000 claims description 3
- 229940050410 gluconate Drugs 0.000 claims description 3
- 208000006116 lymphomatoid granulomatosis Diseases 0.000 claims description 3
- 150000007523 nucleic acids Chemical class 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- 206010062113 splenic marginal zone lymphoma Diseases 0.000 claims description 3
- 229940095064 tartrate Drugs 0.000 claims description 3
- PXMJLILDFJKEMZ-UHFFFAOYSA-N 1-[2-(2-amino-6-phenylquinazolin-8-yl)pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=CC=C1)C1N(CCC1)C(C#CC)=O PXMJLILDFJKEMZ-UHFFFAOYSA-N 0.000 claims description 2
- ZDYQLSMGTKKOHH-UHFFFAOYSA-N 1-[2-(6-phenylquinazolin-8-yl)pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C1(=CC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O ZDYQLSMGTKKOHH-UHFFFAOYSA-N 0.000 claims description 2
- NQQOABTVYFVELZ-UHFFFAOYSA-N 1-[2-[2-amino-6-(2,6-difluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1F)OC1=NC=CC=C1)F)C1N(CCC1)C(C#CC)=O NQQOABTVYFVELZ-UHFFFAOYSA-N 0.000 claims description 2
- MPZFLMYTSJQIAE-UHFFFAOYSA-N 1-[2-[2-amino-6-(2-chloro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl)C1N(CCC1)C(C#CC)=O MPZFLMYTSJQIAE-UHFFFAOYSA-N 0.000 claims description 2
- KIUPYMNRZIOYEM-UHFFFAOYSA-N 1-[2-[2-amino-6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)F)C1N(CCC1)C(C#CC)=O KIUPYMNRZIOYEM-UHFFFAOYSA-N 0.000 claims description 2
- WZLHZRZTRJREKO-UHFFFAOYSA-N 1-[2-[2-amino-6-(2-fluorophenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=CC=C1)F)C1N(CCC1)C(C#CC)=O WZLHZRZTRJREKO-UHFFFAOYSA-N 0.000 claims description 2
- XICHRHMOYVOCCN-UHFFFAOYSA-N 1-[2-[2-amino-6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC=C1)C1N(CCC1)C(C#CC)=O XICHRHMOYVOCCN-UHFFFAOYSA-N 0.000 claims description 2
- IPMZLJUTCWXCNJ-UHFFFAOYSA-N 1-[2-[6-(2,3-difluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(C=CC(=C1F)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O IPMZLJUTCWXCNJ-UHFFFAOYSA-N 0.000 claims description 2
- SPIGOOYYYXLYJN-UHFFFAOYSA-N 1-[2-[6-(2,6-difluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(C(=CC(=C1)OC1=NC=CC=C1)F)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O SPIGOOYYYXLYJN-UHFFFAOYSA-N 0.000 claims description 2
- CMUURVLXSVSDOL-UHFFFAOYSA-N 1-[2-[6-(2,6-difluorophenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(C(=CC=C1)F)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O CMUURVLXSVSDOL-UHFFFAOYSA-N 0.000 claims description 2
- FJTAAVPWELICDJ-UHFFFAOYSA-N 1-[2-[6-(2-chloro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound ClC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O FJTAAVPWELICDJ-UHFFFAOYSA-N 0.000 claims description 2
- LLHAUFLMAHHTCX-UHFFFAOYSA-N 1-[2-[6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O LLHAUFLMAHHTCX-UHFFFAOYSA-N 0.000 claims description 2
- WHGWTBGXVURGIE-UHFFFAOYSA-N 1-[2-[6-(2-fluorophenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(C=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O WHGWTBGXVURGIE-UHFFFAOYSA-N 0.000 claims description 2
- BJYQDMWALQHFEL-UHFFFAOYSA-N 1-[2-[6-(4-phenoxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O BJYQDMWALQHFEL-UHFFFAOYSA-N 0.000 claims description 2
- PHFFASBRAOSBNE-UHFFFAOYSA-N 1-[2-[6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound N1=C(C=CC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O PHFFASBRAOSBNE-UHFFFAOYSA-N 0.000 claims description 2
- DLCZGBMPQZXDEA-UHFFFAOYSA-N 1-[2-[6-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C1(CC1)C1=CC(=NC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O DLCZGBMPQZXDEA-UHFFFAOYSA-N 0.000 claims description 2
- PITDGWGYSSSOOL-UHFFFAOYSA-N 1-[2-[6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC(C1=CC(=NC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1N(CCC1)C(C#CC)=O)(F)F PITDGWGYSSSOOL-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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
- XNZGQNPRCCMRNI-UHFFFAOYSA-N 1-[3-[2-amino-6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)F)C1CN(CC1)C(C=C)=O XNZGQNPRCCMRNI-UHFFFAOYSA-N 0.000 claims description 2
- KDOIKONQYLKWKJ-UHFFFAOYSA-N 1-[3-[2-amino-6-(2-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)OC)C1CN(CC1)C(C=C)=O KDOIKONQYLKWKJ-UHFFFAOYSA-N 0.000 claims description 2
- NVTZEJGWZZVPKB-UHFFFAOYSA-N 1-[3-[2-amino-6-(4-phenoxyphenyl)quinazolin-8-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=CC=CC=C1)C1CN(CCC1)C(C=C)=O NVTZEJGWZZVPKB-UHFFFAOYSA-N 0.000 claims description 2
- IPDIERJKSWJBBO-UHFFFAOYSA-N 1-[3-[2-amino-6-(4-phenoxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=CC=CC=C1)C1CN(CC1)C(C=C)=O IPDIERJKSWJBBO-UHFFFAOYSA-N 0.000 claims description 2
- LEXHVLKKKNBURE-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl LEXHVLKKKNBURE-UHFFFAOYSA-N 0.000 claims description 2
- HLYMQQVVZYTSJE-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl HLYMQQVVZYTSJE-UHFFFAOYSA-N 0.000 claims description 2
- FYFXUJVCBIMCOG-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl FYFXUJVCBIMCOG-UHFFFAOYSA-N 0.000 claims description 2
- MZPUZFQXFAFDNS-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl MZPUZFQXFAFDNS-UHFFFAOYSA-N 0.000 claims description 2
- SLUOKWZWUFJCMK-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)Cl SLUOKWZWUFJCMK-UHFFFAOYSA-N 0.000 claims description 2
- HJFWEOZSMWGSLH-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)Cl HJFWEOZSMWGSLH-UHFFFAOYSA-N 0.000 claims description 2
- MCMLLJRLGURUHK-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)Cl MCMLLJRLGURUHK-UHFFFAOYSA-N 0.000 claims description 2
- YUNDSRIIBDGUTO-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-methoxy-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)OC YUNDSRIIBDGUTO-UHFFFAOYSA-N 0.000 claims description 2
- XEUHAGVLDFMIQB-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-methoxy-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)OC XEUHAGVLDFMIQB-UHFFFAOYSA-N 0.000 claims description 2
- XIZSNTWXZNSGIQ-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)Cl XIZSNTWXZNSGIQ-UHFFFAOYSA-N 0.000 claims description 2
- KITVIOZAYDDKFF-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)Cl KITVIOZAYDDKFF-UHFFFAOYSA-N 0.000 claims description 2
- LUXAJXHOOKPHBO-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)Cl LUXAJXHOOKPHBO-UHFFFAOYSA-N 0.000 claims description 2
- SYCDDBALBNHUEM-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)Cl SYCDDBALBNHUEM-UHFFFAOYSA-N 0.000 claims description 2
- UOTUQLQZBSIZPV-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F UOTUQLQZBSIZPV-UHFFFAOYSA-N 0.000 claims description 2
- XPZUHXKHEDNDPN-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F XPZUHXKHEDNDPN-UHFFFAOYSA-N 0.000 claims description 2
- TVMBWPJQTRIHGA-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F TVMBWPJQTRIHGA-UHFFFAOYSA-N 0.000 claims description 2
- ZPPUHPVSMUICLJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F ZPPUHPVSMUICLJ-UHFFFAOYSA-N 0.000 claims description 2
- AQAYXXGDZPRGCW-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)Cl AQAYXXGDZPRGCW-UHFFFAOYSA-N 0.000 claims description 2
- NOUIPBSMSLDIIU-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)Cl NOUIPBSMSLDIIU-UHFFFAOYSA-N 0.000 claims description 2
- CTHPICJIVWKHRV-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)Cl CTHPICJIVWKHRV-UHFFFAOYSA-N 0.000 claims description 2
- KZJIXRCFAXKEQF-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)Cl KZJIXRCFAXKEQF-UHFFFAOYSA-N 0.000 claims description 2
- VVSLUPXIZXNZQL-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl VVSLUPXIZXNZQL-UHFFFAOYSA-N 0.000 claims description 2
- HRFAGOHXDIUGCT-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl HRFAGOHXDIUGCT-UHFFFAOYSA-N 0.000 claims description 2
- JKDHVTSKUQFAON-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl JKDHVTSKUQFAON-UHFFFAOYSA-N 0.000 claims description 2
- RETOUORDXRGBAC-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl RETOUORDXRGBAC-UHFFFAOYSA-N 0.000 claims description 2
- QPLSXFBAOHVMLZ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F QPLSXFBAOHVMLZ-UHFFFAOYSA-N 0.000 claims description 2
- BBZCBLGKBGIYFB-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-methoxy-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)OC BBZCBLGKBGIYFB-UHFFFAOYSA-N 0.000 claims description 2
- MAPSCOHJJGLANJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-methoxy-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)OC MAPSCOHJJGLANJ-UHFFFAOYSA-N 0.000 claims description 2
- RLVPPBNFLXFWSQ-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(3-fluoropyridin-2-yl)oxy-3-methoxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1F)OC RLVPPBNFLXFWSQ-UHFFFAOYSA-N 0.000 claims description 2
- CQFLLEUZSBQEGC-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(3-fluoropyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1F CQFLLEUZSBQEGC-UHFFFAOYSA-N 0.000 claims description 2
- RHBOCMLMWMNAAP-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(3-fluoropyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1F RHBOCMLMWMNAAP-UHFFFAOYSA-N 0.000 claims description 2
- WFWAEPNHJKYLQS-UHFFFAOYSA-N 1-[3-[5-amino-6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=C(C=C(C=C1)OC1=NC=CC=C1)F)C1CN(CC1)C(C=C)=O WFWAEPNHJKYLQS-UHFFFAOYSA-N 0.000 claims description 2
- UISHUGNWUMHXTE-UHFFFAOYSA-N 1-[3-[5-amino-6-(4-phenoxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=CC=CC=C1)C1CN(CC1)C(C=C)=O UISHUGNWUMHXTE-UHFFFAOYSA-N 0.000 claims description 2
- YNRREUJYSUDDCE-UHFFFAOYSA-N 1-[3-[5-amino-6-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F)C1CN(CC1)C(C=C)=O YNRREUJYSUDDCE-UHFFFAOYSA-N 0.000 claims description 2
- OBGIDMAZWFQCPQ-UHFFFAOYSA-N 1-[3-[5-amino-6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)C1CN(CC1)C(C=C)=O OBGIDMAZWFQCPQ-UHFFFAOYSA-N 0.000 claims description 2
- YWAIUVIGWDUVJA-UHFFFAOYSA-N 1-[3-[6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O YWAIUVIGWDUVJA-UHFFFAOYSA-N 0.000 claims description 2
- SDGGVEXZBCHGPT-UHFFFAOYSA-N 1-[3-[6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound N1=C(C=CC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O SDGGVEXZBCHGPT-UHFFFAOYSA-N 0.000 claims description 2
- JKYWWHVASMBZPA-UHFFFAOYSA-N 1-[3-[6-(5-cyclopropylpyridin-3-yl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C=1C=C(C=NC=1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O JKYWWHVASMBZPA-UHFFFAOYSA-N 0.000 claims description 2
- UAZUPEYDPJZYKG-UHFFFAOYSA-N 1-[3-[6-[2-fluoro-4-(3-fluoropyridin-2-yl)oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1F)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O UAZUPEYDPJZYKG-UHFFFAOYSA-N 0.000 claims description 2
- LLKLYSAGRVDQNY-UHFFFAOYSA-N 1-[3-[6-[3-(3-cyclopropylanilino)phenyl]quinazolin-8-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C=1C=C(C=CC=1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CCC1)C(C=C)=O LLKLYSAGRVDQNY-UHFFFAOYSA-N 0.000 claims description 2
- XPWCJKLQDCYRRM-UHFFFAOYSA-N 1-[3-[6-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C1=CC(=NC=C1)OC1=CC(=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O)F XPWCJKLQDCYRRM-UHFFFAOYSA-N 0.000 claims description 2
- DKQVCWIELGZQHX-UHFFFAOYSA-N 2-[4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 DKQVCWIELGZQHX-UHFFFAOYSA-N 0.000 claims description 2
- MQIAOIROFLTFDR-UHFFFAOYSA-N 2-[4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]phenoxy]pyridine-4-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(OC=2C=C(C(=O)N)C=CN=2)C=C1 MQIAOIROFLTFDR-UHFFFAOYSA-N 0.000 claims description 2
- LLEQRQJVHIEHSY-UHFFFAOYSA-N 2-[[4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzoyl]amino]pyridine-4-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC=2C=C(C(=O)N)C=CN=2)C=C1 LLEQRQJVHIEHSY-UHFFFAOYSA-N 0.000 claims description 2
- NQGWMNNEDNYKMZ-UHFFFAOYSA-N 2-[[4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzoyl]amino]pyridine-4-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC=2C=C(C(=O)N)C=CN=2)C=C1 NQGWMNNEDNYKMZ-UHFFFAOYSA-N 0.000 claims description 2
- NDHNIFVAKQQGCQ-UHFFFAOYSA-N 3-[3-[8-(1-prop-2-enoylpiperidin-3-yl)quinazolin-6-yl]anilino]benzonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1C=C(C=C2C=NC=NC=12)C=1C=C(C=CC=1)NC=1C=C(C#N)C=CC=1 NDHNIFVAKQQGCQ-UHFFFAOYSA-N 0.000 claims description 2
- 108020004705 Codon Proteins 0.000 claims description 2
- BGSRGGZOBOKNGU-UHFFFAOYSA-N N-[3-(2-amino-6-pyridin-3-ylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=CC=1)C=1C=C(C=CC=1)NC(C=C)=O BGSRGGZOBOKNGU-UHFFFAOYSA-N 0.000 claims description 2
- ZCSXIUDBUIBOHQ-UHFFFAOYSA-N N-[3-(6-pyridin-4-ylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound N1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O ZCSXIUDBUIBOHQ-UHFFFAOYSA-N 0.000 claims description 2
- AKVGPWWVFUJPQZ-UHFFFAOYSA-N N-[3-[2-amino-6-(2-chlorophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=CC=C1)Cl)C=1C=C(C=CC=1)NC(C=C)=O AKVGPWWVFUJPQZ-UHFFFAOYSA-N 0.000 claims description 2
- HACHGNVXYNYUAL-UHFFFAOYSA-N N-[3-[2-amino-6-(2-cyanophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=CC=C1)C#N)C=1C=C(C=CC=1)NC(C=C)=O HACHGNVXYNYUAL-UHFFFAOYSA-N 0.000 claims description 2
- GELOZYOGIRXTBY-UHFFFAOYSA-N N-[3-[2-amino-6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=C(C=C1)OC1=NC=CC=C1)F)C=1C=C(C=CC=1)NC(C=C)=O GELOZYOGIRXTBY-UHFFFAOYSA-N 0.000 claims description 2
- ITDXMYADOCRWRB-UHFFFAOYSA-N N-[3-[2-amino-6-(3-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC(=C(C=C1)OC1=NC=CC=C1)F)C=1C=C(C=CC=1)NC(C=C)=O ITDXMYADOCRWRB-UHFFFAOYSA-N 0.000 claims description 2
- FVTXZHAHLYZKFK-UHFFFAOYSA-N N-[3-[2-amino-6-(5-fluoropyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=C(C=1)F)C=1C=C(C=CC=1)NC(C=C)=O FVTXZHAHLYZKFK-UHFFFAOYSA-N 0.000 claims description 2
- PJXLRBDFTIZNJC-UHFFFAOYSA-N N-[3-[2-amino-6-(5-methoxypyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=C(C=1)OC)C=1C=C(C=CC=1)NC(C=C)=O PJXLRBDFTIZNJC-UHFFFAOYSA-N 0.000 claims description 2
- JPFCTSWIDVMACO-UHFFFAOYSA-N N-[3-[2-amino-6-[4-(4-cyanopyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC(=C1)C#N)C=1C=C(C=CC=1)NC(C=C)=O JPFCTSWIDVMACO-UHFFFAOYSA-N 0.000 claims description 2
- PLJURPWJKLDCOF-UHFFFAOYSA-N N-[3-[2-amino-6-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1)C=1C=C(C=CC=1)NC(C=C)=O PLJURPWJKLDCOF-UHFFFAOYSA-N 0.000 claims description 2
- HKIRQVBFOCXVFE-UHFFFAOYSA-N N-[3-[4-amino-6-(3-anilinophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC=NC2=C(C=C(C=C12)C1=CC(=CC=C1)NC1=CC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O HKIRQVBFOCXVFE-UHFFFAOYSA-N 0.000 claims description 2
- ODGRZJQRULUCRB-UHFFFAOYSA-N N-[3-[5-amino-6-(2-chloro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl)C=1C=C(C=CC=1)NC(C=C)=O ODGRZJQRULUCRB-UHFFFAOYSA-N 0.000 claims description 2
- CZUJHQYTUAVVCL-UHFFFAOYSA-N N-[3-[5-amino-6-(2-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=C(C=C(C=C1)OC1=NC=CC=C1)F)C=1C=C(C=CC=1)NC(C=C)=O CZUJHQYTUAVVCL-UHFFFAOYSA-N 0.000 claims description 2
- BHBAHJCYZOOPFL-UHFFFAOYSA-N N-[3-[5-amino-6-(4-phenoxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=CC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O BHBAHJCYZOOPFL-UHFFFAOYSA-N 0.000 claims description 2
- ASDVPZXJWNVKJR-UHFFFAOYSA-N N-[3-[5-amino-6-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F)C=1C=C(C=CC=1)NC(C=C)=O ASDVPZXJWNVKJR-UHFFFAOYSA-N 0.000 claims description 2
- AQWNMPBZLFJHDG-UHFFFAOYSA-N N-[3-[5-amino-6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=C2C=NC=NC2=C(C=C1C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)C=1C=C(C=CC=1)NC(C=C)=O AQWNMPBZLFJHDG-UHFFFAOYSA-N 0.000 claims description 2
- AEOXYEWMKSLSIV-UHFFFAOYSA-N N-[3-[6-(2-cyanophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C1=C(C=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O AEOXYEWMKSLSIV-UHFFFAOYSA-N 0.000 claims description 2
- KQCLOTFDUJSFPF-UHFFFAOYSA-N N-[3-[6-(2-cyanopyridin-4-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C1=NC=CC(=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O KQCLOTFDUJSFPF-UHFFFAOYSA-N 0.000 claims description 2
- BQYNEICTDIJRKB-UHFFFAOYSA-N N-[3-[6-(2-cyclopropylpyridin-4-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C1=NC=CC(=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O BQYNEICTDIJRKB-UHFFFAOYSA-N 0.000 claims description 2
- JTGFFBSVAASDRL-UHFFFAOYSA-N N-[3-[6-(2-methoxy-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound COC1=C(C=CC(=C1)OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O JTGFFBSVAASDRL-UHFFFAOYSA-N 0.000 claims description 2
- YWESXBPCJSWQRH-UHFFFAOYSA-N N-[3-[6-(3-anilinophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O YWESXBPCJSWQRH-UHFFFAOYSA-N 0.000 claims description 2
- ANQMPFMDOIGROT-UHFFFAOYSA-N N-[3-[6-(3-fluoro-4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC=1C=C(C=CC=1OC1=NC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O ANQMPFMDOIGROT-UHFFFAOYSA-N 0.000 claims description 2
- QACHBZUBVYXUDC-UHFFFAOYSA-N N-[3-[6-(3-fluorophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O QACHBZUBVYXUDC-UHFFFAOYSA-N 0.000 claims description 2
- YBCJWVRDGJYJFT-UHFFFAOYSA-N N-[3-[6-(4-anilinophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)NC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O YBCJWVRDGJYJFT-UHFFFAOYSA-N 0.000 claims description 2
- OMEVQOFQHFBWMA-UHFFFAOYSA-N N-[3-[6-(4-phenoxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O OMEVQOFQHFBWMA-UHFFFAOYSA-N 0.000 claims description 2
- WREVGUMVGKTPSU-UHFFFAOYSA-N N-[3-[6-(4-pyridin-2-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound N1=C(C=CC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O WREVGUMVGKTPSU-UHFFFAOYSA-N 0.000 claims description 2
- GSFXLSBIPKBPBJ-UHFFFAOYSA-N N-[3-[6-(4-pyridin-3-yloxyphenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound N1=CC(=CC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O GSFXLSBIPKBPBJ-UHFFFAOYSA-N 0.000 claims description 2
- UZOWIPUBNOEMQJ-UHFFFAOYSA-N N-[3-[6-(5-cyanopyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C=1C=C(C=NC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O UZOWIPUBNOEMQJ-UHFFFAOYSA-N 0.000 claims description 2
- YNHAPLVZFSUFKX-UHFFFAOYSA-N N-[3-[6-(5-cyclopropylpyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C=1C=C(C=NC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O YNHAPLVZFSUFKX-UHFFFAOYSA-N 0.000 claims description 2
- BQJLNVSXGYFZGG-UHFFFAOYSA-N N-[3-[6-[2-chloro-4-(4-cyanopyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=C(C=CC(=C1)OC1=NC=CC(=C1)C#N)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O BQJLNVSXGYFZGG-UHFFFAOYSA-N 0.000 claims description 2
- OUVOYIZPJKVUHV-UHFFFAOYSA-N N-[3-[6-[2-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=C(C=CC(=C1)OC1=NC=CC(=C1)C1CC1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O OUVOYIZPJKVUHV-UHFFFAOYSA-N 0.000 claims description 2
- MDGIXBZXFZZXNV-UHFFFAOYSA-N N-[3-[6-[4-(3-cyclopropylanilino)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C=1C=C(C=CC=1)NC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O MDGIXBZXFZZXNV-UHFFFAOYSA-N 0.000 claims description 2
- IEAPMUHIBUYIDS-UHFFFAOYSA-N N-[3-[6-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C1=CC(=NC=C1)OC1=CC(=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)F IEAPMUHIBUYIDS-UHFFFAOYSA-N 0.000 claims description 2
- WMKOGJKPKUABLE-UHFFFAOYSA-N N-[3-[6-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C1=CC(=NC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O WMKOGJKPKUABLE-UHFFFAOYSA-N 0.000 claims description 2
- SNPPHOUEUOAJAO-UHFFFAOYSA-N N-[3-[6-[4-[3-(trifluoromethyl)anilino]phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C=1C=C(C=CC=1)NC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)(F)F SNPPHOUEUOAJAO-UHFFFAOYSA-N 0.000 claims description 2
- MVUXHOXHLCQQBP-UHFFFAOYSA-N N-[3-[6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C1=CC(=NC=C1)OC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)(F)F MVUXHOXHLCQQBP-UHFFFAOYSA-N 0.000 claims description 2
- QXGSNEZRVOEXNQ-UHFFFAOYSA-N N-[3-[6-[6-(2-fluorophenoxy)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=CC=C1 QXGSNEZRVOEXNQ-UHFFFAOYSA-N 0.000 claims description 2
- CEJHLZXHOGASRE-UHFFFAOYSA-N N-[3-[6-[6-(3-cyanophenoxy)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=CC=1 CEJHLZXHOGASRE-UHFFFAOYSA-N 0.000 claims description 2
- RFFDZYLCUHHSBU-UHFFFAOYSA-N N-[3-[6-[6-(3-cyclopropylphenoxy)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=CC=1 RFFDZYLCUHHSBU-UHFFFAOYSA-N 0.000 claims description 2
- UCCHYOQRNSMZEH-UHFFFAOYSA-N N-[3-[6-[6-(4-chlorophenoxy)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=CC=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=C1 UCCHYOQRNSMZEH-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 238000012163 sequencing technique Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 13
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 10
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 10
- 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 9
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 4
- FJOFEDQJKITORM-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 FJOFEDQJKITORM-UHFFFAOYSA-N 0.000 claims 3
- SPOURIYQFJNTQN-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 SPOURIYQFJNTQN-UHFFFAOYSA-N 0.000 claims 3
- LMTRUMJHALRNML-UHFFFAOYSA-N 1-[3-[7-(2-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O LMTRUMJHALRNML-UHFFFAOYSA-N 0.000 claims 2
- WSENXQRFOOAOAK-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chlorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl WSENXQRFOOAOAK-UHFFFAOYSA-N 0.000 claims 2
- SVCLNJGZCLELRW-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)F SVCLNJGZCLELRW-UHFFFAOYSA-N 0.000 claims 2
- OQRZZKIQIYIXBH-UHFFFAOYSA-N 2-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F OQRZZKIQIYIXBH-UHFFFAOYSA-N 0.000 claims 2
- QXHBNPBIUOSGEG-UHFFFAOYSA-N 4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1 QXHBNPBIUOSGEG-UHFFFAOYSA-N 0.000 claims 2
- 208000023611 Burkitt leukaemia Diseases 0.000 claims 2
- VODJKVNUBAXZGN-UHFFFAOYSA-N N-(3-cyanophenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC(=CC=C2)C#N)C=C1 VODJKVNUBAXZGN-UHFFFAOYSA-N 0.000 claims 2
- ZKRSYPYNTWKUPJ-UHFFFAOYSA-N N-(3-cyclopropylphenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC(=CC=C2)C2CC2)C=C1 ZKRSYPYNTWKUPJ-UHFFFAOYSA-N 0.000 claims 2
- QJWYVGNEIYZZKT-UHFFFAOYSA-N N-(4-chloropyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)Cl)C=C1 QJWYVGNEIYZZKT-UHFFFAOYSA-N 0.000 claims 2
- ILXXKYSHEJXNPL-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-2-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)OC ILXXKYSHEJXNPL-UHFFFAOYSA-N 0.000 claims 2
- AIZCUJJNLDCKMQ-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-3-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F AIZCUJJNLDCKMQ-UHFFFAOYSA-N 0.000 claims 2
- YDFRMYULKBTIML-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-2-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F YDFRMYULKBTIML-UHFFFAOYSA-N 0.000 claims 2
- CPKZGGJVZCXTEB-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-2-methoxy-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)OC CPKZGGJVZCXTEB-UHFFFAOYSA-N 0.000 claims 2
- GZTCKUSPOANOOP-UHFFFAOYSA-N N-(4-fluoropyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)F)C=C1 GZTCKUSPOANOOP-UHFFFAOYSA-N 0.000 claims 2
- WQLSANVINHHELM-UHFFFAOYSA-N N-phenyl-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 WQLSANVINHHELM-UHFFFAOYSA-N 0.000 claims 2
- 208000007452 Plasmacytoma Diseases 0.000 claims 2
- 208000026876 intravascular large B-cell lymphoma Diseases 0.000 claims 2
- 229920001184 polypeptide Polymers 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- SSBHVNNUNGNHEI-UHFFFAOYSA-N 1-[2-[1-amino-7-(2-chloro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)Cl SSBHVNNUNGNHEI-UHFFFAOYSA-N 0.000 claims 1
- LVSHJZNGEBMRSD-UHFFFAOYSA-N 1-[2-[1-amino-7-(2-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)F LVSHJZNGEBMRSD-UHFFFAOYSA-N 0.000 claims 1
- BAMLVRPINJCSNQ-UHFFFAOYSA-N 1-[2-[1-amino-7-(3-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F BAMLVRPINJCSNQ-UHFFFAOYSA-N 0.000 claims 1
- RQXCZUXWOYENKS-UHFFFAOYSA-N 1-[2-[1-amino-7-(4-phenoxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=CC=CC=C1 RQXCZUXWOYENKS-UHFFFAOYSA-N 0.000 claims 1
- NIACBXIOJCUMDT-UHFFFAOYSA-N 1-[2-[1-amino-7-(4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1 NIACBXIOJCUMDT-UHFFFAOYSA-N 0.000 claims 1
- JKMLUVILKJGKGW-UHFFFAOYSA-N 1-[2-[1-amino-7-[4-(3-chloropyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1Cl JKMLUVILKJGKGW-UHFFFAOYSA-N 0.000 claims 1
- QHOJUXOELFHIOT-UHFFFAOYSA-N 1-[2-[1-amino-7-[4-(3-fluoropyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1F QHOJUXOELFHIOT-UHFFFAOYSA-N 0.000 claims 1
- VYZDUZHXPIDACN-UHFFFAOYSA-N 1-[2-[1-amino-7-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 VYZDUZHXPIDACN-UHFFFAOYSA-N 0.000 claims 1
- ADEXTDBNOWSRJW-UHFFFAOYSA-N 1-[2-[1-amino-7-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F ADEXTDBNOWSRJW-UHFFFAOYSA-N 0.000 claims 1
- JIJHOZMLIOSUHB-UHFFFAOYSA-N 1-[3-(2-amino-6-phenylquinazolin-8-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=CC=C1)C1CN(CC1)C(C=C)=O JIJHOZMLIOSUHB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RBFUOOUTZHFHDE-UHFFFAOYSA-N 1-[3-[1-amino-7-(2-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)F RBFUOOUTZHFHDE-UHFFFAOYSA-N 0.000 claims 1
- WOFYLABBWFZYSX-UHFFFAOYSA-N 1-[3-[1-amino-7-(3-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F WOFYLABBWFZYSX-UHFFFAOYSA-N 0.000 claims 1
- RASMRSXTPVXFAI-UHFFFAOYSA-N 1-[3-[1-amino-7-[4-(3-chloropyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1Cl RASMRSXTPVXFAI-UHFFFAOYSA-N 0.000 claims 1
- IZXAEFMVNGVHHF-UHFFFAOYSA-N 1-[3-[1-amino-7-[4-(3-fluoropyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1F IZXAEFMVNGVHHF-UHFFFAOYSA-N 0.000 claims 1
- GTVHXWUXTUOJMD-UHFFFAOYSA-N 1-[3-[1-amino-7-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 GTVHXWUXTUOJMD-UHFFFAOYSA-N 0.000 claims 1
- ZPANRNVDJHWCIX-UHFFFAOYSA-N 1-[3-[1-amino-7-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=CC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F ZPANRNVDJHWCIX-UHFFFAOYSA-N 0.000 claims 1
- WACUWELIAVLWCM-UHFFFAOYSA-N 1-[3-[2-amino-6-(2-fluorophenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=C(C=CC=C1)F)C1CN(CC1)C(C=C)=O WACUWELIAVLWCM-UHFFFAOYSA-N 0.000 claims 1
- RNHFVJHHBMALDQ-UHFFFAOYSA-N 1-[3-[2-amino-6-(6-methylpyridin-3-yl)quinazolin-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)C)C1CN(CCC1)C(C=C)=O RNHFVJHHBMALDQ-UHFFFAOYSA-N 0.000 claims 1
- YTHKZJKFFRYRPD-UHFFFAOYSA-N 1-[3-[2-amino-6-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1)C1CN(CC1)C(C=C)=O YTHKZJKFFRYRPD-UHFFFAOYSA-N 0.000 claims 1
- ZVJBJVJIPCLQAR-UHFFFAOYSA-N 1-[3-[2-amino-6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)C1CN(CC1)C(C=C)=O ZVJBJVJIPCLQAR-UHFFFAOYSA-N 0.000 claims 1
- GRHIULOTWYIDEP-UHFFFAOYSA-N 1-[3-[2-amino-8-(2-chlorophenyl)purin-9-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=C2N=C(N(C2=N1)C1CN(CCC1)C(C=C)=O)C1=C(C=CC=C1)Cl GRHIULOTWYIDEP-UHFFFAOYSA-N 0.000 claims 1
- HCJBJXXWKDAEBZ-UHFFFAOYSA-N 1-[3-[2-amino-8-(2-chlorophenyl)purin-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=C(C=CC=C1)Cl HCJBJXXWKDAEBZ-UHFFFAOYSA-N 0.000 claims 1
- ONAQEERZRFHNEM-UHFFFAOYSA-N 1-[3-[4-amino-6-(4-phenoxyphenyl)quinazolin-8-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)OC1=CC=CC=C1)C1CN(CCC1)C(C=C)=O ONAQEERZRFHNEM-UHFFFAOYSA-N 0.000 claims 1
- XQGADZKYZFIFQH-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)F XQGADZKYZFIFQH-UHFFFAOYSA-N 0.000 claims 1
- NWDAHJVJHIOTCT-UHFFFAOYSA-N 1-[3-[5-amino-3-(2-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC=C1)F NWDAHJVJHIOTCT-UHFFFAOYSA-N 0.000 claims 1
- PPQPDKKXHZFIEF-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-chloro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)Cl PPQPDKKXHZFIEF-UHFFFAOYSA-N 0.000 claims 1
- NDXLGYHQZIOCNQ-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F NDXLGYHQZIOCNQ-UHFFFAOYSA-N 0.000 claims 1
- RASFIDDJFWIERB-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F RASFIDDJFWIERB-UHFFFAOYSA-N 0.000 claims 1
- BPTCCIMOHABPHG-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F BPTCCIMOHABPHG-UHFFFAOYSA-N 0.000 claims 1
- DTCMRQJTWPMMAH-UHFFFAOYSA-N 1-[3-[5-amino-3-(3-fluoro-4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1)F DTCMRQJTWPMMAH-UHFFFAOYSA-N 0.000 claims 1
- JJDXXHJUDBMFDY-UHFFFAOYSA-N 1-[3-[5-amino-3-(4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1 JJDXXHJUDBMFDY-UHFFFAOYSA-N 0.000 claims 1
- QVAUTLDNKOHSJX-UHFFFAOYSA-N 1-[3-[5-amino-3-(4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1 QVAUTLDNKOHSJX-UHFFFAOYSA-N 0.000 claims 1
- RQULWWBZYBVSBS-UHFFFAOYSA-N 1-[3-[5-amino-3-(4-pyridin-2-yloxyphenyl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1 RQULWWBZYBVSBS-UHFFFAOYSA-N 0.000 claims 1
- ZROPTUUJFRQCID-UHFFFAOYSA-N 1-[3-[5-amino-3-(5-pyridin-2-yloxypyridin-2-yl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC=C1 ZROPTUUJFRQCID-UHFFFAOYSA-N 0.000 claims 1
- OFJWGRIKNNTKOY-UHFFFAOYSA-N 1-[3-[5-amino-3-(5-pyridin-2-yloxypyridin-2-yl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC=C1 OFJWGRIKNNTKOY-UHFFFAOYSA-N 0.000 claims 1
- LQJAFALAIUVCRQ-UHFFFAOYSA-N 1-[3-[5-amino-3-(5-pyridin-2-yloxypyridin-2-yl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC=C1 LQJAFALAIUVCRQ-UHFFFAOYSA-N 0.000 claims 1
- PMCVBIHYMJDVME-UHFFFAOYSA-N 1-[3-[5-amino-3-(5-pyridin-2-yloxypyridin-2-yl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC=C1 PMCVBIHYMJDVME-UHFFFAOYSA-N 0.000 claims 1
- RUXUMGMCQLSSKG-UHFFFAOYSA-N 1-[3-[5-amino-3-(6-pyridin-2-yloxypyridin-3-yl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC=C1 RUXUMGMCQLSSKG-UHFFFAOYSA-N 0.000 claims 1
- RIRSCJKWNNPBNA-UHFFFAOYSA-N 1-[3-[5-amino-3-(6-pyridin-2-yloxypyridin-3-yl)imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC=C1 RIRSCJKWNNPBNA-UHFFFAOYSA-N 0.000 claims 1
- UUYCATBOERCACM-UHFFFAOYSA-N 1-[3-[5-amino-3-(6-pyridin-2-yloxypyridin-3-yl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC=C1 UUYCATBOERCACM-UHFFFAOYSA-N 0.000 claims 1
- FXCJOSGNDITWJF-UHFFFAOYSA-N 1-[3-[5-amino-3-(6-pyridin-2-yloxypyridin-3-yl)imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC=C1 FXCJOSGNDITWJF-UHFFFAOYSA-N 0.000 claims 1
- IYZYLPLIUHIDJV-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl IYZYLPLIUHIDJV-UHFFFAOYSA-N 0.000 claims 1
- XEILYEKZNSCKGP-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl XEILYEKZNSCKGP-UHFFFAOYSA-N 0.000 claims 1
- AKEAAFQBRVEGRR-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl AKEAAFQBRVEGRR-UHFFFAOYSA-N 0.000 claims 1
- BWYPOSRKEQGOKP-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl BWYPOSRKEQGOKP-UHFFFAOYSA-N 0.000 claims 1
- VLUCVPCPGJVOSY-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl VLUCVPCPGJVOSY-UHFFFAOYSA-N 0.000 claims 1
- PVVRJVIALDFLHD-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl PVVRJVIALDFLHD-UHFFFAOYSA-N 0.000 claims 1
- KJTKZRHGRYJWLJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl KJTKZRHGRYJWLJ-UHFFFAOYSA-N 0.000 claims 1
- GVDDUGLXVRPXQF-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)Cl GVDDUGLXVRPXQF-UHFFFAOYSA-N 0.000 claims 1
- HPDVZIAVMYHICT-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)F HPDVZIAVMYHICT-UHFFFAOYSA-N 0.000 claims 1
- NJCQHQHLDUXGQL-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)F NJCQHQHLDUXGQL-UHFFFAOYSA-N 0.000 claims 1
- BYAHNSHOCISSML-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)F BYAHNSHOCISSML-UHFFFAOYSA-N 0.000 claims 1
- LADJMJMJYUSKEY-UHFFFAOYSA-N 1-[3-[5-amino-3-[2-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)OC)F LADJMJMJYUSKEY-UHFFFAOYSA-N 0.000 claims 1
- KWVCXNIDWUHVEM-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl KWVCXNIDWUHVEM-UHFFFAOYSA-N 0.000 claims 1
- YNDQYDWJWCRTPM-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl YNDQYDWJWCRTPM-UHFFFAOYSA-N 0.000 claims 1
- BQWOLTXGIDRMQZ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl BQWOLTXGIDRMQZ-UHFFFAOYSA-N 0.000 claims 1
- FEWSNPXOBCFGMF-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-chloro-4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)Cl FEWSNPXOBCFGMF-UHFFFAOYSA-N 0.000 claims 1
- VGWXHTXLQGYWLJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)F VGWXHTXLQGYWLJ-UHFFFAOYSA-N 0.000 claims 1
- UHDLCSYDUSPJAG-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)F UHDLCSYDUSPJAG-UHFFFAOYSA-N 0.000 claims 1
- LAZHOVQUYBDYKJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)F LAZHOVQUYBDYKJ-UHFFFAOYSA-N 0.000 claims 1
- JTAYBNWCYWKNMK-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)OC)F JTAYBNWCYWKNMK-UHFFFAOYSA-N 0.000 claims 1
- ITAOTVAAJCELHJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1C(F)(F)F)F ITAOTVAAJCELHJ-UHFFFAOYSA-N 0.000 claims 1
- BCCNBKGDSIFZSG-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F BCCNBKGDSIFZSG-UHFFFAOYSA-N 0.000 claims 1
- HBUWTOZXUOJUHG-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F HBUWTOZXUOJUHG-UHFFFAOYSA-N 0.000 claims 1
- VQLYBSASTSUIQH-UHFFFAOYSA-N 1-[3-[5-amino-3-[3-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)F VQLYBSASTSUIQH-UHFFFAOYSA-N 0.000 claims 1
- JNGSMOJLHVEJEE-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(3-fluoropyridin-2-yl)oxy-3-methoxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC=C1F)OC JNGSMOJLHVEJEE-UHFFFAOYSA-N 0.000 claims 1
- POCGOONHBJVSLL-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)F POCGOONHBJVSLL-UHFFFAOYSA-N 0.000 claims 1
- DOUYZMBSYLMZMN-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)F DOUYZMBSYLMZMN-UHFFFAOYSA-N 0.000 claims 1
- IOCQTTGIIQHZLQ-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)F IOCQTTGIIQHZLQ-UHFFFAOYSA-N 0.000 claims 1
- NENLBOBLGTVGOP-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-2-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=C(C=C(C=C1)OC1=NC=CC(=C1)C1CC1)F NENLBOBLGTVGOP-UHFFFAOYSA-N 0.000 claims 1
- BWLVPCYLPXCBLB-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-3-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)F BWLVPCYLPXCBLB-UHFFFAOYSA-N 0.000 claims 1
- RPOMATVZONLZBR-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-3-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)F RPOMATVZONLZBR-UHFFFAOYSA-N 0.000 claims 1
- SSPQAPCRWRFXCW-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-3-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)F SSPQAPCRWRFXCW-UHFFFAOYSA-N 0.000 claims 1
- ZYHDEMGKYHIQRJ-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxy-3-fluorophenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC(=C(C=C1)OC1=NC=CC(=C1)C1CC1)F ZYHDEMGKYHIQRJ-UHFFFAOYSA-N 0.000 claims 1
- ZTFOMESZDPBMKF-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 ZTFOMESZDPBMKF-UHFFFAOYSA-N 0.000 claims 1
- WMDHYITYQVNWNI-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 WMDHYITYQVNWNI-UHFFFAOYSA-N 0.000 claims 1
- FVWQNPNOKSJWGF-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 FVWQNPNOKSJWGF-UHFFFAOYSA-N 0.000 claims 1
- XPKCLDAGNRWYCO-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C1CC1 XPKCLDAGNRWYCO-UHFFFAOYSA-N 0.000 claims 1
- XBYBVKGWVWEKNG-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)OC XBYBVKGWVWEKNG-UHFFFAOYSA-N 0.000 claims 1
- UEKSENOWIQPTMU-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)OC UEKSENOWIQPTMU-UHFFFAOYSA-N 0.000 claims 1
- CNCGKTBKQSSPCX-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)OC CNCGKTBKQSSPCX-UHFFFAOYSA-N 0.000 claims 1
- UHWSPGOKTOEDFE-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-(4-methoxypyridin-2-yl)oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)OC UHWSPGOKTOEDFE-UHFFFAOYSA-N 0.000 claims 1
- ORNMVBBVUUOOFH-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC=C1C(F)(F)F ORNMVBBVUUOOFH-UHFFFAOYSA-N 0.000 claims 1
- JYFPJYOQELZONR-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1C(F)(F)F JYFPJYOQELZONR-UHFFFAOYSA-N 0.000 claims 1
- ZNDPJKVMYYGQRX-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F ZNDPJKVMYYGQRX-UHFFFAOYSA-N 0.000 claims 1
- PJVZOJGDNHVJOQ-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F PJVZOJGDNHVJOQ-UHFFFAOYSA-N 0.000 claims 1
- ZOTQHIVVYVSIRB-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F ZOTQHIVVYVSIRB-UHFFFAOYSA-N 0.000 claims 1
- WQAZCDSGMLSTGI-UHFFFAOYSA-N 1-[3-[5-amino-3-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F WQAZCDSGMLSTGI-UHFFFAOYSA-N 0.000 claims 1
- VLQNMOAERRBLMM-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-cyclopropylpyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C1CC1 VLQNMOAERRBLMM-UHFFFAOYSA-N 0.000 claims 1
- WNWWIHCNAUZCBW-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-cyclopropylpyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C1CC1 WNWWIHCNAUZCBW-UHFFFAOYSA-N 0.000 claims 1
- ZGURIOBRGPQNLM-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-cyclopropylpyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C1CC1 ZGURIOBRGPQNLM-UHFFFAOYSA-N 0.000 claims 1
- QZTLTLRQUFYGTM-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-cyclopropylpyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C1CC1 QZTLTLRQUFYGTM-UHFFFAOYSA-N 0.000 claims 1
- GUMFBHLEESXYJY-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-methoxypyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)OC GUMFBHLEESXYJY-UHFFFAOYSA-N 0.000 claims 1
- AHCNZUDNTNICCR-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-methoxypyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)OC AHCNZUDNTNICCR-UHFFFAOYSA-N 0.000 claims 1
- MSUOGYBJWIRPIO-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-methoxypyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)OC MSUOGYBJWIRPIO-UHFFFAOYSA-N 0.000 claims 1
- ZZDPRKKODIADHA-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-(4-methoxypyridin-2-yl)oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)OC ZZDPRKKODIADHA-UHFFFAOYSA-N 0.000 claims 1
- ATLCLZJGNOQAGQ-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F ATLCLZJGNOQAGQ-UHFFFAOYSA-N 0.000 claims 1
- IJJSHAQYOWKCJU-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F IJJSHAQYOWKCJU-UHFFFAOYSA-N 0.000 claims 1
- LULOTTWLZAWMOL-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F LULOTTWLZAWMOL-UHFFFAOYSA-N 0.000 claims 1
- LJQNWXFYWFYAES-UHFFFAOYSA-N 1-[3-[5-amino-3-[5-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-2-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C1=NC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F LJQNWXFYWFYAES-UHFFFAOYSA-N 0.000 claims 1
- ULTGNBACCYCOOU-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-cyclopropylpyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C1CC1 ULTGNBACCYCOOU-UHFFFAOYSA-N 0.000 claims 1
- LRISUHIAFQUTFP-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-cyclopropylpyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C1CC1 LRISUHIAFQUTFP-UHFFFAOYSA-N 0.000 claims 1
- WLABPWWYKPKUDN-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-cyclopropylpyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C1CC1 WLABPWWYKPKUDN-UHFFFAOYSA-N 0.000 claims 1
- FWIWTXXRPKROTH-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-cyclopropylpyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C1CC1 FWIWTXXRPKROTH-UHFFFAOYSA-N 0.000 claims 1
- RIQNCUWPISMQJY-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-methoxypyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)OC RIQNCUWPISMQJY-UHFFFAOYSA-N 0.000 claims 1
- IYFXFKYWVRSXAZ-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-methoxypyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)OC IYFXFKYWVRSXAZ-UHFFFAOYSA-N 0.000 claims 1
- RRPJOGIDKNBZPR-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-methoxypyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)OC RRPJOGIDKNBZPR-UHFFFAOYSA-N 0.000 claims 1
- KURRIVGLIOWTOS-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-(4-methoxypyridin-2-yl)oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)OC KURRIVGLIOWTOS-UHFFFAOYSA-N 0.000 claims 1
- DBXYPXIFHBLLPM-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C(F)(F)F DBXYPXIFHBLLPM-UHFFFAOYSA-N 0.000 claims 1
- ZSZKGRDAJRSHJB-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C(F)(F)F ZSZKGRDAJRSHJB-UHFFFAOYSA-N 0.000 claims 1
- HIJLGKQPYJTNAS-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C(F)(F)F HIJLGKQPYJTNAS-UHFFFAOYSA-N 0.000 claims 1
- ZRCHGNJQPXWHRY-UHFFFAOYSA-N 1-[3-[5-amino-3-[6-[4-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]imidazo[1,5-c]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C=C)=O)C=1C=NC(=CC=1)OC1=NC=CC(=C1)C(F)(F)F ZRCHGNJQPXWHRY-UHFFFAOYSA-N 0.000 claims 1
- YUFZQIOJEPEDCG-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O YUFZQIOJEPEDCG-UHFFFAOYSA-N 0.000 claims 1
- SKOPZWHKGHSJQP-UHFFFAOYSA-N 1-[3-[6-(4-phenoxyphenyl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O SKOPZWHKGHSJQP-UHFFFAOYSA-N 0.000 claims 1
- BICBQSKDLYVXIA-UHFFFAOYSA-N 1-[3-[6-(6-phenoxypyridin-3-yl)quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=N1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O BICBQSKDLYVXIA-UHFFFAOYSA-N 0.000 claims 1
- YFKOQEJDTJNPGJ-UHFFFAOYSA-N 1-[3-[6-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC(=C1)C(F)(F)F)C=1C=C2C=NC=NC2=C(C=1)C1CN(CC1)C(C=C)=O YFKOQEJDTJNPGJ-UHFFFAOYSA-N 0.000 claims 1
- JXCQPACGEQMNLQ-UHFFFAOYSA-N 1-[3-[6-[3-[3-(trifluoromethyl)anilino]phenyl]quinazolin-8-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC(C=1C=C(C=CC=1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C1CN(CCC1)C(C=C)=O)(F)F JXCQPACGEQMNLQ-UHFFFAOYSA-N 0.000 claims 1
- MXICJTZMYZSYQJ-UHFFFAOYSA-N 1-[3-[6-[6-(2-fluorophenoxy)pyridin-3-yl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C2CN(CC2)C(C=C)=O)C=CC=C1 MXICJTZMYZSYQJ-UHFFFAOYSA-N 0.000 claims 1
- JDHHUSPMMRWJIY-UHFFFAOYSA-N 1-[3-[6-[6-(3-fluorophenoxy)pyridin-3-yl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C2CN(CC2)C(C=C)=O)C=CC=1 JDHHUSPMMRWJIY-UHFFFAOYSA-N 0.000 claims 1
- QDDJQQUJHSFUNG-UHFFFAOYSA-N 1-[3-[6-[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC(C=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C2CN(CC2)C(C=C)=O)C=CC=1)(F)F QDDJQQUJHSFUNG-UHFFFAOYSA-N 0.000 claims 1
- ZWBHONZRRKZNPC-UHFFFAOYSA-N 1-[3-[7-(2,3-difluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1F)OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O ZWBHONZRRKZNPC-UHFFFAOYSA-N 0.000 claims 1
- WGEMZKFHJYRMPF-UHFFFAOYSA-N 1-[3-[7-(2-chloro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC(=C1)OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O WGEMZKFHJYRMPF-UHFFFAOYSA-N 0.000 claims 1
- WXBBXYQHPOQZLZ-UHFFFAOYSA-N 1-[3-[7-(2-methoxy-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=C(C=CC(=C1)OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O WXBBXYQHPOQZLZ-UHFFFAOYSA-N 0.000 claims 1
- SOPBZRNBBALROP-UHFFFAOYSA-N 1-[3-[7-(3-fluoro-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(C=CC=1OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O SOPBZRNBBALROP-UHFFFAOYSA-N 0.000 claims 1
- GOPJMPYCYCBLOD-UHFFFAOYSA-N 1-[3-[7-(3-methoxy-4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC=1C=C(C=CC=1OC1=NC=CC=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O GOPJMPYCYCBLOD-UHFFFAOYSA-N 0.000 claims 1
- KETSJPUCOQVPIG-UHFFFAOYSA-N 1-[3-[7-(4-pyridin-2-yloxyphenyl)pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound N1=C(C=CC=C1)OC1=CC=C(C=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O KETSJPUCOQVPIG-UHFFFAOYSA-N 0.000 claims 1
- GXMZIHGODKLSCD-UHFFFAOYSA-N 1-[3-[7-[4-(4-cyclopropylpyridin-2-yl)oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C1=CC(=NC=C1)OC1=CC=C(C=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O GXMZIHGODKLSCD-UHFFFAOYSA-N 0.000 claims 1
- WTRNOOYLIFHIMY-UHFFFAOYSA-N 1-[3-[7-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyrrolo[1,2-c]pyrimidin-5-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC(C1=CC(=NC=C1)OC1=CC=C(C=C1)C1=CC(=C2N1C=NC=C2)C1CN(CC1)C(C=C)=O)(F)F WTRNOOYLIFHIMY-UHFFFAOYSA-N 0.000 claims 1
- PKXBJBLTGHSUNB-UHFFFAOYSA-N 1-[3-[8-(2-chlorophenyl)purin-9-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC=C1)C=1N(C2=NC=NC=C2N=1)C1CN(CC1)C(C=C)=O PKXBJBLTGHSUNB-UHFFFAOYSA-N 0.000 claims 1
- AKXUIYMVEZQRAF-UHFFFAOYSA-N 1-[3-[8-(2-fluorophenyl)purin-9-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC=C1)C=1N(C2=NC=NC=C2N=1)C1CN(CC1)C(C=C)=O AKXUIYMVEZQRAF-UHFFFAOYSA-N 0.000 claims 1
- YCROLOYLLNUHHP-UHFFFAOYSA-N 2,3-difluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C(=C(C(=O)NC2=NC=CC=C2)C=C1)F)F YCROLOYLLNUHHP-UHFFFAOYSA-N 0.000 claims 1
- DZZFDZUOZJBHFI-UHFFFAOYSA-N 2-[3-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)F DZZFDZUOZJBHFI-UHFFFAOYSA-N 0.000 claims 1
- RTWHUPNPDSSKOQ-UHFFFAOYSA-N 2-[3-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]phenoxy]pyridine-4-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(OC=2C=C(C(=O)N)C=CN=2)C=C1)F RTWHUPNPDSSKOQ-UHFFFAOYSA-N 0.000 claims 1
- PPUKOVORCPJTQK-UHFFFAOYSA-N 2-[4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]phenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 PPUKOVORCPJTQK-UHFFFAOYSA-N 0.000 claims 1
- KSKLBRMLMCSFLG-UHFFFAOYSA-N 2-[4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 KSKLBRMLMCSFLG-UHFFFAOYSA-N 0.000 claims 1
- RVXLXDZMUSIRRY-UHFFFAOYSA-N 2-[4-[2-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC(=NC=12)N)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 RVXLXDZMUSIRRY-UHFFFAOYSA-N 0.000 claims 1
- BHGAWUNPTHWOQS-UHFFFAOYSA-N 2-[4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 BHGAWUNPTHWOQS-UHFFFAOYSA-N 0.000 claims 1
- XJMZGCKCCABFRN-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chlorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl XJMZGCKCCABFRN-UHFFFAOYSA-N 0.000 claims 1
- DXLDMWAKJMLJNE-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)F DXLDMWAKJMLJNE-UHFFFAOYSA-N 0.000 claims 1
- TXPQBCKCEFJFNV-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chlorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl TXPQBCKCEFJFNV-UHFFFAOYSA-N 0.000 claims 1
- HDJSMDOBHWKUAS-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluorophenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)F HDJSMDOBHWKUAS-UHFFFAOYSA-N 0.000 claims 1
- KUZAXAWXMRCQDB-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 KUZAXAWXMRCQDB-UHFFFAOYSA-N 0.000 claims 1
- ZUSWFTDRYSOIMC-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-3-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(OC2=C(C#N)C=CC=N2)C=C1 ZUSWFTDRYSOIMC-UHFFFAOYSA-N 0.000 claims 1
- GIBVEQDAXSCZDM-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 GIBVEQDAXSCZDM-UHFFFAOYSA-N 0.000 claims 1
- UCWKYJHHELZIGB-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chlorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl UCWKYJHHELZIGB-UHFFFAOYSA-N 0.000 claims 1
- DMGDPKLJAMWBQW-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluorophenoxy]pyridine-3-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(OC2=C(C#N)C=CC=N2)C=C1)F DMGDPKLJAMWBQW-UHFFFAOYSA-N 0.000 claims 1
- KWVDNFGCDDGMGO-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)F KWVDNFGCDDGMGO-UHFFFAOYSA-N 0.000 claims 1
- FXYJTIDFUZZNHZ-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chlorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl FXYJTIDFUZZNHZ-UHFFFAOYSA-N 0.000 claims 1
- XTMMJQNNXFNYRP-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)F XTMMJQNNXFNYRP-UHFFFAOYSA-N 0.000 claims 1
- VLXXYKBSTWGJBB-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 VLXXYKBSTWGJBB-UHFFFAOYSA-N 0.000 claims 1
- JSZLNCLMRCVHPW-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chlorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl JSZLNCLMRCVHPW-UHFFFAOYSA-N 0.000 claims 1
- RDKALUKILDRJSV-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(OC=2C=C(C#N)C=CN=2)C=C1)F RDKALUKILDRJSV-UHFFFAOYSA-N 0.000 claims 1
- PFMMHKINGMOCOC-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chlorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)Cl PFMMHKINGMOCOC-UHFFFAOYSA-N 0.000 claims 1
- BTNOLHIPPPTMLU-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluorophenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(OC=2C=C(C#N)C=CN=2)C=C1)F BTNOLHIPPPTMLU-UHFFFAOYSA-N 0.000 claims 1
- JPNISEBGTBWOTM-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-3-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(OC2=C(C#N)C=CC=N2)C=C1 JPNISEBGTBWOTM-UHFFFAOYSA-N 0.000 claims 1
- WTSGVABETXTOFE-UHFFFAOYSA-N 2-[4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]phenoxy]pyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(OC=2C=C(C#N)C=CN=2)C=C1 WTSGVABETXTOFE-UHFFFAOYSA-N 0.000 claims 1
- ZKIPKUNRYBRHAM-UHFFFAOYSA-N 2-[5-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-2-yl]oxypyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=CC(=NC=1)OC=1C=C(C#N)C=CN=1 ZKIPKUNRYBRHAM-UHFFFAOYSA-N 0.000 claims 1
- MTVQDJCYQHMUOL-UHFFFAOYSA-N 2-[5-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-2-yl]oxypyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=CC(=NC=1)OC=1C=C(C#N)C=CN=1 MTVQDJCYQHMUOL-UHFFFAOYSA-N 0.000 claims 1
- WNAZZGJAPADJMH-UHFFFAOYSA-N 2-[5-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-2-yl]oxypyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)OC=1C=C(C#N)C=CN=1 WNAZZGJAPADJMH-UHFFFAOYSA-N 0.000 claims 1
- JQHARBOCPHLVTC-UHFFFAOYSA-N 2-[5-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-2-yl]oxypyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)OC=1C=C(C#N)C=CN=1 JQHARBOCPHLVTC-UHFFFAOYSA-N 0.000 claims 1
- ZANZYEYXFAHDFJ-UHFFFAOYSA-N 2-[6-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-3-yl]oxypyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C=N1)OC=1C=C(C#N)C=CN=1 ZANZYEYXFAHDFJ-UHFFFAOYSA-N 0.000 claims 1
- FTGYWFGXEGRGJJ-UHFFFAOYSA-N 2-[6-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-3-yl]oxypyridine-4-carbonitrile Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C=N1)OC=1C=C(C#N)C=CN=1 FTGYWFGXEGRGJJ-UHFFFAOYSA-N 0.000 claims 1
- RVLGWQGVHBSSLL-UHFFFAOYSA-N 2-[6-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-3-yl]oxypyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C=N1)OC=1C=C(C#N)C=CN=1 RVLGWQGVHBSSLL-UHFFFAOYSA-N 0.000 claims 1
- HCFDCZLNUHGVHR-UHFFFAOYSA-N 2-[6-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]pyridin-3-yl]oxypyridine-4-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C=N1)OC=1C=C(C#N)C=CN=1 HCFDCZLNUHGVHR-UHFFFAOYSA-N 0.000 claims 1
- DKIZIRORGRBFLF-UHFFFAOYSA-N 2-[[3-chloro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzoyl]amino]pyridine-4-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC=2C=C(C(=O)N)C=CN=2)C=C1)Cl DKIZIRORGRBFLF-UHFFFAOYSA-N 0.000 claims 1
- TXBXYBINOVPVIV-UHFFFAOYSA-N 2-chloro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)Cl TXBXYBINOVPVIV-UHFFFAOYSA-N 0.000 claims 1
- MLMNZHARXNNHCF-UHFFFAOYSA-N 2-chloro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl MLMNZHARXNNHCF-UHFFFAOYSA-N 0.000 claims 1
- SEHDIQWXJKVSIE-UHFFFAOYSA-N 2-chloro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)Cl SEHDIQWXJKVSIE-UHFFFAOYSA-N 0.000 claims 1
- ABGWHSZQQUYSGP-UHFFFAOYSA-N 2-chloro-N-(4-cyanopyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl ABGWHSZQQUYSGP-UHFFFAOYSA-N 0.000 claims 1
- OAUKFWPNBOFNPQ-UHFFFAOYSA-N 2-chloro-N-(4-cyclopropylpyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl OAUKFWPNBOFNPQ-UHFFFAOYSA-N 0.000 claims 1
- BWYXGNXZCJHECC-UHFFFAOYSA-N 2-chloro-N-(4-cyclopropylpyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl BWYXGNXZCJHECC-UHFFFAOYSA-N 0.000 claims 1
- KYYNNYXRFCAJJK-UHFFFAOYSA-N 2-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F KYYNNYXRFCAJJK-UHFFFAOYSA-N 0.000 claims 1
- KFHKSJNTPVEPJA-UHFFFAOYSA-N 2-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F KFHKSJNTPVEPJA-UHFFFAOYSA-N 0.000 claims 1
- YETCWFMBHVZWCI-UHFFFAOYSA-N 2-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F YETCWFMBHVZWCI-UHFFFAOYSA-N 0.000 claims 1
- MJLUZRHUKMSEHG-UHFFFAOYSA-N 2-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F MJLUZRHUKMSEHG-UHFFFAOYSA-N 0.000 claims 1
- IQOKEENQFTXLPI-UHFFFAOYSA-N 2-fluoro-N-(4-methoxypyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC(=C2)OC)C=C1)F IQOKEENQFTXLPI-UHFFFAOYSA-N 0.000 claims 1
- AQDAZUXZYWYWKS-UHFFFAOYSA-N 2-methoxy-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)OC AQDAZUXZYWYWKS-UHFFFAOYSA-N 0.000 claims 1
- GLEDZTKOTKIZGA-UHFFFAOYSA-N 2-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)OC GLEDZTKOTKIZGA-UHFFFAOYSA-N 0.000 claims 1
- UHAIOGGHYIFISZ-UHFFFAOYSA-N 2-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)OC UHAIOGGHYIFISZ-UHFFFAOYSA-N 0.000 claims 1
- YRDXJCQMKODHPC-UHFFFAOYSA-N 3-[5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridin-2-yl]oxybenzonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)OC=1C=C(C#N)C=CC=1 YRDXJCQMKODHPC-UHFFFAOYSA-N 0.000 claims 1
- NPRUXXGUPTXUIG-UHFFFAOYSA-N 3-chloro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl NPRUXXGUPTXUIG-UHFFFAOYSA-N 0.000 claims 1
- BOPHQLAMPYJSCH-UHFFFAOYSA-N 3-chloro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl BOPHQLAMPYJSCH-UHFFFAOYSA-N 0.000 claims 1
- SWJVUCODQMRAHR-UHFFFAOYSA-N 3-chloro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl SWJVUCODQMRAHR-UHFFFAOYSA-N 0.000 claims 1
- RWVDWVCPLMTGAS-UHFFFAOYSA-N 3-chloro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl RWVDWVCPLMTGAS-UHFFFAOYSA-N 0.000 claims 1
- GQKDUGDNUQVOPY-UHFFFAOYSA-N 3-chloro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl GQKDUGDNUQVOPY-UHFFFAOYSA-N 0.000 claims 1
- HEQRFYRASIFFPB-UHFFFAOYSA-N 3-chloro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl HEQRFYRASIFFPB-UHFFFAOYSA-N 0.000 claims 1
- RIVMAAPKKLUNKT-UHFFFAOYSA-N 3-chloro-N-(4-cyanopyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl RIVMAAPKKLUNKT-UHFFFAOYSA-N 0.000 claims 1
- VENVXMQEFQKXMR-UHFFFAOYSA-N 3-chloro-N-(4-cyanopyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl VENVXMQEFQKXMR-UHFFFAOYSA-N 0.000 claims 1
- KMSAIMKVPWFTMX-UHFFFAOYSA-N 3-chloro-N-(4-cyanopyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl KMSAIMKVPWFTMX-UHFFFAOYSA-N 0.000 claims 1
- XBVDPKZRPOEDEZ-UHFFFAOYSA-N 3-chloro-N-(4-cyclopropylpyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl XBVDPKZRPOEDEZ-UHFFFAOYSA-N 0.000 claims 1
- OUBVLJFEZMYBFM-UHFFFAOYSA-N 3-chloro-N-(4-cyclopropylpyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl OUBVLJFEZMYBFM-UHFFFAOYSA-N 0.000 claims 1
- SUTFRCNIGPKHCH-UHFFFAOYSA-N 3-cyano-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C#N SUTFRCNIGPKHCH-UHFFFAOYSA-N 0.000 claims 1
- XHHSEFVFUQMHBO-UHFFFAOYSA-N 3-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F XHHSEFVFUQMHBO-UHFFFAOYSA-N 0.000 claims 1
- TYGGDTJRCCSTBQ-UHFFFAOYSA-N 3-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F TYGGDTJRCCSTBQ-UHFFFAOYSA-N 0.000 claims 1
- AGMIAUIVLRJUPT-UHFFFAOYSA-N 3-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F AGMIAUIVLRJUPT-UHFFFAOYSA-N 0.000 claims 1
- GKMDZFYVUMPPQI-UHFFFAOYSA-N 3-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F GKMDZFYVUMPPQI-UHFFFAOYSA-N 0.000 claims 1
- CREQRNYFYAZIMJ-UHFFFAOYSA-N 3-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F CREQRNYFYAZIMJ-UHFFFAOYSA-N 0.000 claims 1
- KOVXFRJQCMTRHC-UHFFFAOYSA-N 3-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F KOVXFRJQCMTRHC-UHFFFAOYSA-N 0.000 claims 1
- UPWBXCCWUGGHEY-UHFFFAOYSA-N 3-fluoro-N-(4-methoxypyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)OC)C=C1)F UPWBXCCWUGGHEY-UHFFFAOYSA-N 0.000 claims 1
- YAGQNUWJASNRHM-UHFFFAOYSA-N 3-fluoro-N-phenyl-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=CC=CC=C2)C=C1)F YAGQNUWJASNRHM-UHFFFAOYSA-N 0.000 claims 1
- GXNPXBUEJVXXEV-UHFFFAOYSA-N 3-methoxy-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)OC GXNPXBUEJVXXEV-UHFFFAOYSA-N 0.000 claims 1
- FVCXELRRWVVGRG-UHFFFAOYSA-N 3-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)OC FVCXELRRWVVGRG-UHFFFAOYSA-N 0.000 claims 1
- VYOSHGCTCOVXHA-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-2-fluoro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F VYOSHGCTCOVXHA-UHFFFAOYSA-N 0.000 claims 1
- IKNOWDQYMYSOIO-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl IKNOWDQYMYSOIO-UHFFFAOYSA-N 0.000 claims 1
- AHPKUZPXKYMKEI-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(3-chloropyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2Cl)C=C1 AHPKUZPXKYMKEI-UHFFFAOYSA-N 0.000 claims 1
- CHKSIBXDHPRHMU-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(3-fluoropyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2F)C=C1 CHKSIBXDHPRHMU-UHFFFAOYSA-N 0.000 claims 1
- QJOOYIIQTDHRDQ-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 QJOOYIIQTDHRDQ-UHFFFAOYSA-N 0.000 claims 1
- LORITRUFVLJIGS-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 LORITRUFVLJIGS-UHFFFAOYSA-N 0.000 claims 1
- GMEULOZMWKUMLW-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 GMEULOZMWKUMLW-UHFFFAOYSA-N 0.000 claims 1
- GOBFHTAQUKBWOD-UHFFFAOYSA-N 4-[1-amino-5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=CC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 GOBFHTAQUKBWOD-UHFFFAOYSA-N 0.000 claims 1
- KEUADBLWKCDJRI-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-2-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F KEUADBLWKCDJRI-UHFFFAOYSA-N 0.000 claims 1
- VGDDNUPTSAQEGG-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl VGDDNUPTSAQEGG-UHFFFAOYSA-N 0.000 claims 1
- LUQKAQMFNJRYQH-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(3-chloropyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2Cl)C=C1 LUQKAQMFNJRYQH-UHFFFAOYSA-N 0.000 claims 1
- NZLYNYNLSUORTA-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 NZLYNYNLSUORTA-UHFFFAOYSA-N 0.000 claims 1
- GRHSNUDGGSPEED-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 GRHSNUDGGSPEED-UHFFFAOYSA-N 0.000 claims 1
- WIPYNBMWBQMERN-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 WIPYNBMWBQMERN-UHFFFAOYSA-N 0.000 claims 1
- WJOUMONTIGQWNW-UHFFFAOYSA-N 4-[1-amino-5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 WJOUMONTIGQWNW-UHFFFAOYSA-N 0.000 claims 1
- GIEMZAUTYGSAOJ-UHFFFAOYSA-N 4-[2,5-diamino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC(=NC=12)N)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 GIEMZAUTYGSAOJ-UHFFFAOYSA-N 0.000 claims 1
- FKVPWUHBZFVGAB-UHFFFAOYSA-N 4-[2-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-(4-methylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC(=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C)C=C1 FKVPWUHBZFVGAB-UHFFFAOYSA-N 0.000 claims 1
- BCORUAKTSBEKGJ-UHFFFAOYSA-N 4-[2-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC(=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BCORUAKTSBEKGJ-UHFFFAOYSA-N 0.000 claims 1
- FFTXRPXOPALPFT-UHFFFAOYSA-N 4-[4-amino-8-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=NC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 FFTXRPXOPALPFT-UHFFFAOYSA-N 0.000 claims 1
- CTOCVFLWTZQRNB-UHFFFAOYSA-N 4-[4-amino-8-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=NC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 CTOCVFLWTZQRNB-UHFFFAOYSA-N 0.000 claims 1
- BVEFSHPLIXYASA-UHFFFAOYSA-N 4-[4-amino-8-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=NC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BVEFSHPLIXYASA-UHFFFAOYSA-N 0.000 claims 1
- UIMBUHGTSYLUDD-UHFFFAOYSA-N 4-[4-amino-8-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C=1N=CN=C2N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 UIMBUHGTSYLUDD-UHFFFAOYSA-N 0.000 claims 1
- QCDXPAUQILXKRS-UHFFFAOYSA-N 4-[4-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C=1N=CN=C2N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 QCDXPAUQILXKRS-UHFFFAOYSA-N 0.000 claims 1
- NFSSGMNLADBWAW-UHFFFAOYSA-N 4-[4-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C=1N=CN=C2N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 NFSSGMNLADBWAW-UHFFFAOYSA-N 0.000 claims 1
- HYUWBYWTMFQFAE-UHFFFAOYSA-N 4-[4-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-a][1,3,5]triazin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C=1N=CN=C2N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 HYUWBYWTMFQFAE-UHFFFAOYSA-N 0.000 claims 1
- MTEVEAWKRFNQEJ-UHFFFAOYSA-N 4-[4-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-5-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=CC(=C2C(=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 MTEVEAWKRFNQEJ-UHFFFAOYSA-N 0.000 claims 1
- GMTJSKKUJRBFGZ-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-2-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F GMTJSKKUJRBFGZ-UHFFFAOYSA-N 0.000 claims 1
- MYPPVIIAKPJWHO-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3,5-dichloro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1Cl)Cl MYPPVIIAKPJWHO-UHFFFAOYSA-N 0.000 claims 1
- JGYLHZWECLREKW-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3,5-difluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1F)F JGYLHZWECLREKW-UHFFFAOYSA-N 0.000 claims 1
- MISICJICQUANCX-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl MISICJICQUANCX-UHFFFAOYSA-N 0.000 claims 1
- YTFLUZBYFFNQRV-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl YTFLUZBYFFNQRV-UHFFFAOYSA-N 0.000 claims 1
- DVJVSJJLOJRGRW-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl DVJVSJJLOJRGRW-UHFFFAOYSA-N 0.000 claims 1
- CCAIIJCDFLGWBA-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl CCAIIJCDFLGWBA-UHFFFAOYSA-N 0.000 claims 1
- QAOGXEGUAWMVAH-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F QAOGXEGUAWMVAH-UHFFFAOYSA-N 0.000 claims 1
- UYEFTJMSLCBIFN-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F UYEFTJMSLCBIFN-UHFFFAOYSA-N 0.000 claims 1
- BZUVVFGJCFSANK-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(3-chloropyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC=C2Cl)C=C1 BZUVVFGJCFSANK-UHFFFAOYSA-N 0.000 claims 1
- ZOEMQJMORBAPSC-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-chloropyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)Cl)C=C1 ZOEMQJMORBAPSC-UHFFFAOYSA-N 0.000 claims 1
- HBCIAFUAJLNZTH-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyanopyridin-2-yl)-3-fluorobenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F HBCIAFUAJLNZTH-UHFFFAOYSA-N 0.000 claims 1
- INCBPRKGBABOFK-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 INCBPRKGBABOFK-UHFFFAOYSA-N 0.000 claims 1
- XMOSTDRNHZQUEY-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyclopropylpyridin-2-yl)-3-fluorobenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F XMOSTDRNHZQUEY-UHFFFAOYSA-N 0.000 claims 1
- FKJJVENAPGUEED-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 FKJJVENAPGUEED-UHFFFAOYSA-N 0.000 claims 1
- QUVLLPMRDUNGLR-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 QUVLLPMRDUNGLR-UHFFFAOYSA-N 0.000 claims 1
- FGEDTKFITCLJOE-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-phenylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 FGEDTKFITCLJOE-UHFFFAOYSA-N 0.000 claims 1
- CKXACLOBRKCMFS-UHFFFAOYSA-N 4-[5-(1-but-2-ynoylpyrrolidin-2-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 CKXACLOBRKCMFS-UHFFFAOYSA-N 0.000 claims 1
- ZSZMFARRZORSND-UHFFFAOYSA-N 4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 ZSZMFARRZORSND-UHFFFAOYSA-N 0.000 claims 1
- SLODALASUNJBOH-UHFFFAOYSA-N 4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 SLODALASUNJBOH-UHFFFAOYSA-N 0.000 claims 1
- KTPZWXLRSHMNQJ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F KTPZWXLRSHMNQJ-UHFFFAOYSA-N 0.000 claims 1
- ZAMUEACDDSFJJQ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl ZAMUEACDDSFJJQ-UHFFFAOYSA-N 0.000 claims 1
- RTJOYHBSDMYFGT-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl RTJOYHBSDMYFGT-UHFFFAOYSA-N 0.000 claims 1
- WSXCDJKLJVYJMF-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl WSXCDJKLJVYJMF-UHFFFAOYSA-N 0.000 claims 1
- OBPJXINFFHRPJB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N OBPJXINFFHRPJB-UHFFFAOYSA-N 0.000 claims 1
- UAOBPHFJCQAWRV-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C#N UAOBPHFJCQAWRV-UHFFFAOYSA-N 0.000 claims 1
- YZBMHIPZCAYPEY-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N YZBMHIPZCAYPEY-UHFFFAOYSA-N 0.000 claims 1
- RQVZRWJDXSKSLB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F RQVZRWJDXSKSLB-UHFFFAOYSA-N 0.000 claims 1
- GDRZOGPOFFEJDX-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F GDRZOGPOFFEJDX-UHFFFAOYSA-N 0.000 claims 1
- UQOIMKOBOHGYIM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl UQOIMKOBOHGYIM-UHFFFAOYSA-N 0.000 claims 1
- BVDWWPGSGFHVKT-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl BVDWWPGSGFHVKT-UHFFFAOYSA-N 0.000 claims 1
- AIHKTYBXZVNUCL-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N AIHKTYBXZVNUCL-UHFFFAOYSA-N 0.000 claims 1
- WEIGLMMGXQYDOK-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N WEIGLMMGXQYDOK-UHFFFAOYSA-N 0.000 claims 1
- SRGOMCVTGJHULV-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C#N SRGOMCVTGJHULV-UHFFFAOYSA-N 0.000 claims 1
- YHHLOCYPLUZKBO-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F YHHLOCYPLUZKBO-UHFFFAOYSA-N 0.000 claims 1
- RTEBVZWNYSFTRU-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F RTEBVZWNYSFTRU-UHFFFAOYSA-N 0.000 claims 1
- NGVVDIMVPVENLB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F NGVVDIMVPVENLB-UHFFFAOYSA-N 0.000 claims 1
- UFWKYRIILJQMGV-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F UFWKYRIILJQMGV-UHFFFAOYSA-N 0.000 claims 1
- WXSXKHZULVAQGU-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F WXSXKHZULVAQGU-UHFFFAOYSA-N 0.000 claims 1
- SGTUFYWVGLLTOB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F SGTUFYWVGLLTOB-UHFFFAOYSA-N 0.000 claims 1
- JAUMEFRRRKMNNZ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 JAUMEFRRRKMNNZ-UHFFFAOYSA-N 0.000 claims 1
- VRCKZCNCQAPELV-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C(F)(F)F VRCKZCNCQAPELV-UHFFFAOYSA-N 0.000 claims 1
- VICUTUIUWSYGAH-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F VICUTUIUWSYGAH-UHFFFAOYSA-N 0.000 claims 1
- IOWWHGQXTPDIBQ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 IOWWHGQXTPDIBQ-UHFFFAOYSA-N 0.000 claims 1
- UAIGFCQYRYZOBE-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 UAIGFCQYRYZOBE-UHFFFAOYSA-N 0.000 claims 1
- IBTVYRZNTKOKAO-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-2-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F IBTVYRZNTKOKAO-UHFFFAOYSA-N 0.000 claims 1
- VSITURWSPVVVHF-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-3-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F VSITURWSPVVVHF-UHFFFAOYSA-N 0.000 claims 1
- DXDDTRVEMGZPLD-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 DXDDTRVEMGZPLD-UHFFFAOYSA-N 0.000 claims 1
- BUDCINQJMNWFFN-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-2-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BUDCINQJMNWFFN-UHFFFAOYSA-N 0.000 claims 1
- YPKVDYICLDEBNP-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F YPKVDYICLDEBNP-UHFFFAOYSA-N 0.000 claims 1
- UEVKJAFAKAGENF-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl UEVKJAFAKAGENF-UHFFFAOYSA-N 0.000 claims 1
- GHMXBYUZRYCGMF-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl GHMXBYUZRYCGMF-UHFFFAOYSA-N 0.000 claims 1
- NLIHJKZDNHDNOR-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl NLIHJKZDNHDNOR-UHFFFAOYSA-N 0.000 claims 1
- KONCTWNJRJSZIW-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N KONCTWNJRJSZIW-UHFFFAOYSA-N 0.000 claims 1
- BXJVTNLAAUFCNA-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C#N BXJVTNLAAUFCNA-UHFFFAOYSA-N 0.000 claims 1
- HAHKDWRAOJDZNB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N HAHKDWRAOJDZNB-UHFFFAOYSA-N 0.000 claims 1
- XDDAACOBYFJPBL-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F XDDAACOBYFJPBL-UHFFFAOYSA-N 0.000 claims 1
- RPJDZJAPUXPVHB-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F RPJDZJAPUXPVHB-UHFFFAOYSA-N 0.000 claims 1
- QDKXJOHVKCDMHR-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F QDKXJOHVKCDMHR-UHFFFAOYSA-N 0.000 claims 1
- MXJCCHXAACNYIM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl MXJCCHXAACNYIM-UHFFFAOYSA-N 0.000 claims 1
- ALBVLAGJQPCGJR-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl ALBVLAGJQPCGJR-UHFFFAOYSA-N 0.000 claims 1
- QWOIZGVKDXVIAK-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl QWOIZGVKDXVIAK-UHFFFAOYSA-N 0.000 claims 1
- ZDTAHPJZHKFNDC-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N ZDTAHPJZHKFNDC-UHFFFAOYSA-N 0.000 claims 1
- KOYZGESIVROSMA-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N KOYZGESIVROSMA-UHFFFAOYSA-N 0.000 claims 1
- JZRFWXCTYCKCMJ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C#N JZRFWXCTYCKCMJ-UHFFFAOYSA-N 0.000 claims 1
- ZOFACJPTBHWMOK-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F ZOFACJPTBHWMOK-UHFFFAOYSA-N 0.000 claims 1
- YGNZBVDOEPMSPZ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F YGNZBVDOEPMSPZ-UHFFFAOYSA-N 0.000 claims 1
- XGXJQRPQMVORJI-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F XGXJQRPQMVORJI-UHFFFAOYSA-N 0.000 claims 1
- TYTNFMZBXVGXBF-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F TYTNFMZBXVGXBF-UHFFFAOYSA-N 0.000 claims 1
- RAIXVZJQLJXQMJ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F RAIXVZJQLJXQMJ-UHFFFAOYSA-N 0.000 claims 1
- MZOHNRUIYCPPEA-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F MZOHNRUIYCPPEA-UHFFFAOYSA-N 0.000 claims 1
- GWXNWTZWTYQVAO-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 GWXNWTZWTYQVAO-UHFFFAOYSA-N 0.000 claims 1
- GYWNQWLUIBQODM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C(F)(F)F GYWNQWLUIBQODM-UHFFFAOYSA-N 0.000 claims 1
- FEVGANOGLUWODM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-fluorobenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F FEVGANOGLUWODM-UHFFFAOYSA-N 0.000 claims 1
- QNHIVSPYVMPLKM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 QNHIVSPYVMPLKM-UHFFFAOYSA-N 0.000 claims 1
- WCWQDFFLWHKNNM-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-methoxypyridin-2-yl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)OC)C=C1 WCWQDFFLWHKNNM-UHFFFAOYSA-N 0.000 claims 1
- OPYBIHGVHKFQIZ-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 OPYBIHGVHKFQIZ-UHFFFAOYSA-N 0.000 claims 1
- LRECFJFWXQQYBA-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-3-(trifluoromethyl)benzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F LRECFJFWXQQYBA-UHFFFAOYSA-N 0.000 claims 1
- OZDQAMJMRMRPIC-UHFFFAOYSA-N 4-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 OZDQAMJMRMRPIC-UHFFFAOYSA-N 0.000 claims 1
- JRJDBDXDKHYDGO-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F JRJDBDXDKHYDGO-UHFFFAOYSA-N 0.000 claims 1
- LDMSORPZHJJASZ-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl LDMSORPZHJJASZ-UHFFFAOYSA-N 0.000 claims 1
- XRHMVPWTBOQWHY-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl XRHMVPWTBOQWHY-UHFFFAOYSA-N 0.000 claims 1
- INEIFAKKRMDIFD-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl INEIFAKKRMDIFD-UHFFFAOYSA-N 0.000 claims 1
- SJNHVMASDWBENX-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N SJNHVMASDWBENX-UHFFFAOYSA-N 0.000 claims 1
- ICQGLNYDOLAHOI-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C#N ICQGLNYDOLAHOI-UHFFFAOYSA-N 0.000 claims 1
- RMPZJKPYBIIFRH-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N RMPZJKPYBIIFRH-UHFFFAOYSA-N 0.000 claims 1
- JQSXDWJCVQXBAI-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F JQSXDWJCVQXBAI-UHFFFAOYSA-N 0.000 claims 1
- AXOIDPIRQUMRSY-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F AXOIDPIRQUMRSY-UHFFFAOYSA-N 0.000 claims 1
- BNVKMEFDHUQCAM-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl BNVKMEFDHUQCAM-UHFFFAOYSA-N 0.000 claims 1
- YGSNMCYYHFIUFO-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl YGSNMCYYHFIUFO-UHFFFAOYSA-N 0.000 claims 1
- UMQCEDOIVXQFIH-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N UMQCEDOIVXQFIH-UHFFFAOYSA-N 0.000 claims 1
- MIHKHPTWRQLXEM-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N MIHKHPTWRQLXEM-UHFFFAOYSA-N 0.000 claims 1
- QXHXFOFGHAMXKV-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C#N QXHXFOFGHAMXKV-UHFFFAOYSA-N 0.000 claims 1
- NAVZDMHWGRHQPD-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F NAVZDMHWGRHQPD-UHFFFAOYSA-N 0.000 claims 1
- QALNDADJWIMEHV-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F QALNDADJWIMEHV-UHFFFAOYSA-N 0.000 claims 1
- CHVDARXVFCSBCR-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F CHVDARXVFCSBCR-UHFFFAOYSA-N 0.000 claims 1
- XDOUBDKJVJULHN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F XDOUBDKJVJULHN-UHFFFAOYSA-N 0.000 claims 1
- UBPYAPUJIOJPAU-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F UBPYAPUJIOJPAU-UHFFFAOYSA-N 0.000 claims 1
- OPTDXULFWXZRCI-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F OPTDXULFWXZRCI-UHFFFAOYSA-N 0.000 claims 1
- RNQWPNPGHHJKOF-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 RNQWPNPGHHJKOF-UHFFFAOYSA-N 0.000 claims 1
- LTGZZVGLKWOPAP-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C(F)(F)F LTGZZVGLKWOPAP-UHFFFAOYSA-N 0.000 claims 1
- GBZHDSJNQOFHKI-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F GBZHDSJNQOFHKI-UHFFFAOYSA-N 0.000 claims 1
- WLMCWEWSHJNRBO-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 WLMCWEWSHJNRBO-UHFFFAOYSA-N 0.000 claims 1
- HSPJRPTWDQULDD-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 HSPJRPTWDQULDD-UHFFFAOYSA-N 0.000 claims 1
- MOOQBUHMNNKFBN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-2-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F MOOQBUHMNNKFBN-UHFFFAOYSA-N 0.000 claims 1
- AWPQBHUARVZPKF-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-3-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F AWPQBHUARVZPKF-UHFFFAOYSA-N 0.000 claims 1
- FXRAOPYYSPLOHK-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 FXRAOPYYSPLOHK-UHFFFAOYSA-N 0.000 claims 1
- ATPJMLUGTDBHMX-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F ATPJMLUGTDBHMX-UHFFFAOYSA-N 0.000 claims 1
- DFMQHTLDOUVDGE-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl DFMQHTLDOUVDGE-UHFFFAOYSA-N 0.000 claims 1
- LJEISNCXKYXCBN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl LJEISNCXKYXCBN-UHFFFAOYSA-N 0.000 claims 1
- GGZMUKNHQIZFHG-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl GGZMUKNHQIZFHG-UHFFFAOYSA-N 0.000 claims 1
- FZHANDGBSVJGSI-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N FZHANDGBSVJGSI-UHFFFAOYSA-N 0.000 claims 1
- BLXOCSCJBOCQBN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C#N BLXOCSCJBOCQBN-UHFFFAOYSA-N 0.000 claims 1
- PCJLAECAIXJJNV-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N PCJLAECAIXJJNV-UHFFFAOYSA-N 0.000 claims 1
- RSSKFWQIMFIJMQ-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F RSSKFWQIMFIJMQ-UHFFFAOYSA-N 0.000 claims 1
- DXIAUCLQSDCNHF-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-2-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC=C2)C=C1)F DXIAUCLQSDCNHF-UHFFFAOYSA-N 0.000 claims 1
- KPKJNVLAFIVVEP-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-(trifluoromethyl)-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C(F)(F)F KPKJNVLAFIVVEP-UHFFFAOYSA-N 0.000 claims 1
- JPSKHDIYFZIKGB-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)Cl JPSKHDIYFZIKGB-UHFFFAOYSA-N 0.000 claims 1
- OBNOBYAWWMRJJB-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)Cl OBNOBYAWWMRJJB-UHFFFAOYSA-N 0.000 claims 1
- IRTCCXCEQQSZKF-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl IRTCCXCEQQSZKF-UHFFFAOYSA-N 0.000 claims 1
- IWBQBEMUHURGAF-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C#N IWBQBEMUHURGAF-UHFFFAOYSA-N 0.000 claims 1
- JCMBIJKFMVUQIP-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)C#N JCMBIJKFMVUQIP-UHFFFAOYSA-N 0.000 claims 1
- MKNYVZCSXNDCMK-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-cyano-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C#N MKNYVZCSXNDCMK-UHFFFAOYSA-N 0.000 claims 1
- PGENQPZKTRTOTP-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F PGENQPZKTRTOTP-UHFFFAOYSA-N 0.000 claims 1
- IPPBYTVUCRQICN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F IPPBYTVUCRQICN-UHFFFAOYSA-N 0.000 claims 1
- PYBOIOUKGWXIAV-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F PYBOIOUKGWXIAV-UHFFFAOYSA-N 0.000 claims 1
- NOKSVVDLXFMKQG-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-2-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F NOKSVVDLXFMKQG-UHFFFAOYSA-N 0.000 claims 1
- ZNBMVWNOKFDLEK-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)C(F)(F)F ZNBMVWNOKFDLEK-UHFFFAOYSA-N 0.000 claims 1
- VFMJXBIZGRBCPB-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)-3-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F VFMJXBIZGRBCPB-UHFFFAOYSA-N 0.000 claims 1
- CZTHGHIWEQYYOK-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 CZTHGHIWEQYYOK-UHFFFAOYSA-N 0.000 claims 1
- BGRAYUJIPQTTMT-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)C(F)(F)F BGRAYUJIPQTTMT-UHFFFAOYSA-N 0.000 claims 1
- ZMKKBUCWTUGOHT-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)-2-fluorobenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F ZMKKBUCWTUGOHT-UHFFFAOYSA-N 0.000 claims 1
- GVGYLTFYMGTIEN-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 GVGYLTFYMGTIEN-UHFFFAOYSA-N 0.000 claims 1
- CYWGEKAUNFSQTK-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-methoxypyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)OC)C=C1 CYWGEKAUNFSQTK-UHFFFAOYSA-N 0.000 claims 1
- WVDDDPUJYMJHOL-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 WVDDDPUJYMJHOL-UHFFFAOYSA-N 0.000 claims 1
- OIYGVOIDICFWJE-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-yl-3-(trifluoromethyl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)C(F)(F)F OIYGVOIDICFWJE-UHFFFAOYSA-N 0.000 claims 1
- JNWZRSVELQIQMH-UHFFFAOYSA-N 4-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 JNWZRSVELQIQMH-UHFFFAOYSA-N 0.000 claims 1
- BUDCINQJMNWFFN-LJQANCHMSA-N 4-[5-amino-1-[(2R)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@@H]1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BUDCINQJMNWFFN-LJQANCHMSA-N 0.000 claims 1
- BUDCINQJMNWFFN-IBGZPJMESA-N 4-[5-amino-1-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@H]1N(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BUDCINQJMNWFFN-IBGZPJMESA-N 0.000 claims 1
- DXDDTRVEMGZPLD-HXUWFJFHSA-N 4-[5-amino-1-[(3R)-1-but-2-ynoylpiperidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@H]1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 DXDDTRVEMGZPLD-HXUWFJFHSA-N 0.000 claims 1
- OZDQAMJMRMRPIC-LJQANCHMSA-N 4-[5-amino-1-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@H]1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 OZDQAMJMRMRPIC-LJQANCHMSA-N 0.000 claims 1
- FXRAOPYYSPLOHK-LJQANCHMSA-N 4-[5-amino-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1C[C@@H](CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 FXRAOPYYSPLOHK-LJQANCHMSA-N 0.000 claims 1
- JNWZRSVELQIQMH-GOSISDBHSA-N 4-[5-amino-1-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 JNWZRSVELQIQMH-GOSISDBHSA-N 0.000 claims 1
- DXDDTRVEMGZPLD-FQEVSTJZSA-N 4-[5-amino-1-[(3S)-1-but-2-ynoylpiperidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@@H]1CN(CCC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 DXDDTRVEMGZPLD-FQEVSTJZSA-N 0.000 claims 1
- OZDQAMJMRMRPIC-IBGZPJMESA-N 4-[5-amino-1-[(3S)-1-but-2-ynoylpyrrolidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound NC1=NC=CC=2N1C(=NC=2[C@@H]1CN(CC1)C(C#CC)=O)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 OZDQAMJMRMRPIC-IBGZPJMESA-N 0.000 claims 1
- FXRAOPYYSPLOHK-IBGZPJMESA-N 4-[5-amino-1-[(3S)-1-prop-2-enoylpiperidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1C[C@H](CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 FXRAOPYYSPLOHK-IBGZPJMESA-N 0.000 claims 1
- JNWZRSVELQIQMH-SFHVURJKSA-N 4-[5-amino-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 JNWZRSVELQIQMH-SFHVURJKSA-N 0.000 claims 1
- BEIHOKHAVHFZHG-UHFFFAOYSA-N 4-[5-amino-8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-(3-fluoropyridin-2-yl)benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C(=C2C=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC=C2F)C=C1 BEIHOKHAVHFZHG-UHFFFAOYSA-N 0.000 claims 1
- PWABEMWALYYSNM-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-3-chloro-N-(3-fluoropyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=C(C=C(C(=O)NC2=NC=CC=C2F)C=C1)Cl PWABEMWALYYSNM-UHFFFAOYSA-N 0.000 claims 1
- VIPWBIGSVRFYOB-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-3-chloro-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)Cl VIPWBIGSVRFYOB-UHFFFAOYSA-N 0.000 claims 1
- UCZYCFWEJZOEFO-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl UCZYCFWEJZOEFO-UHFFFAOYSA-N 0.000 claims 1
- ZOPNAIQQLCWKQU-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F ZOPNAIQQLCWKQU-UHFFFAOYSA-N 0.000 claims 1
- OINKZXAJFCORQO-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-(3-fluoropyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC=C2F)C=C1 OINKZXAJFCORQO-UHFFFAOYSA-N 0.000 claims 1
- QUMYNWPLYYLVQK-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 QUMYNWPLYYLVQK-UHFFFAOYSA-N 0.000 claims 1
- FTUJWWHWVQPFNE-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-(4-cyclopropylpyridin-2-yl)-3-fluorobenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F FTUJWWHWVQPFNE-UHFFFAOYSA-N 0.000 claims 1
- PVLIDVBIUOPEQM-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 PVLIDVBIUOPEQM-UHFFFAOYSA-N 0.000 claims 1
- MXSXDVPPOXTPCV-UHFFFAOYSA-N 4-[5-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C(=C2C=NC=NC=12)N)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 MXSXDVPPOXTPCV-UHFFFAOYSA-N 0.000 claims 1
- FHRUGSNLUIVWSK-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-2,3-difluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C(=C(C(=O)NC2=NC=CC=C2)C=C1)F)F FHRUGSNLUIVWSK-UHFFFAOYSA-N 0.000 claims 1
- LIPBRRMMPWBGFT-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-3,5-difluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1F)F LIPBRRMMPWBGFT-UHFFFAOYSA-N 0.000 claims 1
- SZXLGUGFVKLLMR-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-3-chloro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)Cl SZXLGUGFVKLLMR-UHFFFAOYSA-N 0.000 claims 1
- FAXRQVUDNZSTHG-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F FAXRQVUDNZSTHG-UHFFFAOYSA-N 0.000 claims 1
- ZSFQAWOSCLNCEN-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-3-fluoro-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC=C2)C=C1)F ZSFQAWOSCLNCEN-UHFFFAOYSA-N 0.000 claims 1
- NEXWAIQXTBPQCP-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-(4-cyanopyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 NEXWAIQXTBPQCP-UHFFFAOYSA-N 0.000 claims 1
- BRSSPRVWONVCKV-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-(4-cyclopropylpyridin-2-yl)-3-fluorobenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F BRSSPRVWONVCKV-UHFFFAOYSA-N 0.000 claims 1
- LQLJPURVYDQQBH-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-(4-cyclopropylpyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 LQLJPURVYDQQBH-UHFFFAOYSA-N 0.000 claims 1
- UWQXTNKBFOTSAE-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-(4-fluoropyridin-2-yl)benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)F)C=C1 UWQXTNKBFOTSAE-UHFFFAOYSA-N 0.000 claims 1
- INMVQGQZWVCYLG-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 INMVQGQZWVCYLG-UHFFFAOYSA-N 0.000 claims 1
- UQAGNJIZESDVJE-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-phenylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 UQAGNJIZESDVJE-UHFFFAOYSA-N 0.000 claims 1
- VRDPFCRYZRGMHV-UHFFFAOYSA-N 4-[8-(1-but-2-ynoylpyrrolidin-2-yl)quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1C(CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 VRDPFCRYZRGMHV-UHFFFAOYSA-N 0.000 claims 1
- VLBULJOYRKATTQ-UHFFFAOYSA-N 4-[8-(1-prop-2-enoyl-3,6-dihydro-2H-pyridin-5-yl)quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(=CCC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 VLBULJOYRKATTQ-UHFFFAOYSA-N 0.000 claims 1
- ULTSDDJPMKNXKK-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpiperidin-3-yl)quinazolin-5-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1C=CC(=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 ULTSDDJPMKNXKK-UHFFFAOYSA-N 0.000 claims 1
- VEALQFMDRMKPFW-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-5-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=CC(=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 VEALQFMDRMKPFW-UHFFFAOYSA-N 0.000 claims 1
- ZQDIWFICVTYYKH-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1 ZQDIWFICVTYYKH-UHFFFAOYSA-N 0.000 claims 1
- CCXMFRCNSALHOE-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 CCXMFRCNSALHOE-UHFFFAOYSA-N 0.000 claims 1
- RGSMUPGVTSNTJG-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[5-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=C(C=C2)C(F)(F)F)C=C1 RGSMUPGVTSNTJG-UHFFFAOYSA-N 0.000 claims 1
- OADJIOWIQYCAPN-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridazin-4-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CN=NC=C2)C=C1 OADJIOWIQYCAPN-UHFFFAOYSA-N 0.000 claims 1
- AWZZOGYZHXBDJV-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 AWZZOGYZHXBDJV-UHFFFAOYSA-N 0.000 claims 1
- QMESXTVCUSYNJX-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridin-3-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC=2C=NC=CC=2)C=C1 QMESXTVCUSYNJX-UHFFFAOYSA-N 0.000 claims 1
- OJDQLVIYQQQGFN-UHFFFAOYSA-N 4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-pyridin-4-ylbenzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC=NC=C2)C=C1 OJDQLVIYQQQGFN-UHFFFAOYSA-N 0.000 claims 1
- NRAZHAYIAKQPGQ-UHFFFAOYSA-N 4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-5-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=CC(=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 NRAZHAYIAKQPGQ-UHFFFAOYSA-N 0.000 claims 1
- HHLJENOCANTXSH-UHFFFAOYSA-N 4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1 HHLJENOCANTXSH-UHFFFAOYSA-N 0.000 claims 1
- PLNUQOJWQXLULN-UHFFFAOYSA-N 4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 PLNUQOJWQXLULN-UHFFFAOYSA-N 0.000 claims 1
- KCCUNMIZZHNQSD-UHFFFAOYSA-N 4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 KCCUNMIZZHNQSD-UHFFFAOYSA-N 0.000 claims 1
- BPGNTVPXWROCFW-UHFFFAOYSA-N 4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-3-ylbenzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC=2C=NC=CC=2)C=C1 BPGNTVPXWROCFW-UHFFFAOYSA-N 0.000 claims 1
- XVXXHCVQXCXHOY-UHFFFAOYSA-N 5-[2-amino-8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-phenylpyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC(=NC=12)N)C=1C=CC(=NC=1)C(=O)NC1=CC=CC=C1 XVXXHCVQXCXHOY-UHFFFAOYSA-N 0.000 claims 1
- JINMTXIFVVWPBZ-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C#N JINMTXIFVVWPBZ-UHFFFAOYSA-N 0.000 claims 1
- DTRBKRVSQWSPRR-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C1CC1 DTRBKRVSQWSPRR-UHFFFAOYSA-N 0.000 claims 1
- FZVRSIJOZIFAEI-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C(F)(F)F FZVRSIJOZIFAEI-UHFFFAOYSA-N 0.000 claims 1
- ZBDDQBFCLGTKDM-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC=C1 ZBDDQBFCLGTKDM-UHFFFAOYSA-N 0.000 claims 1
- VYHVPMBPZAHAAO-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C#N VYHVPMBPZAHAAO-UHFFFAOYSA-N 0.000 claims 1
- FIQXLIOHBVJGLZ-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C1CC1 FIQXLIOHBVJGLZ-UHFFFAOYSA-N 0.000 claims 1
- BCHVRMVVSJCKRB-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C(F)(F)F BCHVRMVVSJCKRB-UHFFFAOYSA-N 0.000 claims 1
- PUDWRTLKEQPKNB-UHFFFAOYSA-N 5-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-2-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C=1C=CC(=NC=1)C(=O)NC1=NC=CC=C1 PUDWRTLKEQPKNB-UHFFFAOYSA-N 0.000 claims 1
- DEIIEUGPHACLSD-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C#N DEIIEUGPHACLSD-UHFFFAOYSA-N 0.000 claims 1
- XEPVMQPIKZEPTP-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C1CC1 XEPVMQPIKZEPTP-UHFFFAOYSA-N 0.000 claims 1
- CKKZWUGKUXJVAZ-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C(F)(F)F CKKZWUGKUXJVAZ-UHFFFAOYSA-N 0.000 claims 1
- IQTDJFVSJXIUTK-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC=C1 IQTDJFVSJXIUTK-UHFFFAOYSA-N 0.000 claims 1
- UAJHDXCRKLXSLS-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C#N UAJHDXCRKLXSLS-UHFFFAOYSA-N 0.000 claims 1
- FOHRIVKEYVLITJ-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C1CC1 FOHRIVKEYVLITJ-UHFFFAOYSA-N 0.000 claims 1
- VCAGYTBZOJIVRU-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC(=C1)C(F)(F)F VCAGYTBZOJIVRU-UHFFFAOYSA-N 0.000 claims 1
- NVLHIIPJARNWKP-UHFFFAOYSA-N 5-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C=1C=CC(=NC=1)C(=O)NC1=NC=CC=C1 NVLHIIPJARNWKP-UHFFFAOYSA-N 0.000 claims 1
- QJZYXZYGWYVYPE-UHFFFAOYSA-N 5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]-N-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)C(F)(F)F QJZYXZYGWYVYPE-UHFFFAOYSA-N 0.000 claims 1
- VZWRASJMLKPNKJ-UHFFFAOYSA-N 5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-3-carbonitrile Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=NC=C(C#N)C=1 VZWRASJMLKPNKJ-UHFFFAOYSA-N 0.000 claims 1
- QPUVPWRASCIJJC-UHFFFAOYSA-N 5-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)C(F)(F)F QPUVPWRASCIJJC-UHFFFAOYSA-N 0.000 claims 1
- HSAHKBIYBWYIKR-UHFFFAOYSA-N 5-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]-N-pyridin-2-ylpyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=NC=CC=C1 HSAHKBIYBWYIKR-UHFFFAOYSA-N 0.000 claims 1
- FKQXKGJDDVVBBR-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 FKQXKGJDDVVBBR-UHFFFAOYSA-N 0.000 claims 1
- JSKNUMTUGCIUAC-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 JSKNUMTUGCIUAC-UHFFFAOYSA-N 0.000 claims 1
- LYZPGKWQYHMIOT-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 LYZPGKWQYHMIOT-UHFFFAOYSA-N 0.000 claims 1
- SAUZHXMRDTYMMA-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CCC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC=C2)C=C1 SAUZHXMRDTYMMA-UHFFFAOYSA-N 0.000 claims 1
- PIPTYJOYMIMNMP-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 PIPTYJOYMIMNMP-UHFFFAOYSA-N 0.000 claims 1
- PNGNEBHUKDCZQR-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 PNGNEBHUKDCZQR-UHFFFAOYSA-N 0.000 claims 1
- GXUBEYBVNRCHJG-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 GXUBEYBVNRCHJG-UHFFFAOYSA-N 0.000 claims 1
- VIGWTEFZKUWGPM-UHFFFAOYSA-N 6-[5-amino-1-(1-but-2-ynoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-3-carboxamide Chemical compound NC1=NC=CC=2N1C(=NC=2C1CN(CC1)C(C#CC)=O)C1=NC=C(C(=O)NC2=NC=CC=C2)C=C1 VIGWTEFZKUWGPM-UHFFFAOYSA-N 0.000 claims 1
- NDCVQSXMXYLLJS-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 NDCVQSXMXYLLJS-UHFFFAOYSA-N 0.000 claims 1
- PJOLHMIVBXEXMM-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 PJOLHMIVBXEXMM-UHFFFAOYSA-N 0.000 claims 1
- ZJEPJDWYORWQFK-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 ZJEPJDWYORWQFK-UHFFFAOYSA-N 0.000 claims 1
- RPSONEZGXPNBAE-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpiperidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC=C2)C=C1 RPSONEZGXPNBAE-UHFFFAOYSA-N 0.000 claims 1
- DYEQDBYNJXGDQP-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyanopyridin-2-yl)pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 DYEQDBYNJXGDQP-UHFFFAOYSA-N 0.000 claims 1
- MTERLDNIPJNCQN-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-(4-cyclopropylpyridin-2-yl)pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 MTERLDNIPJNCQN-UHFFFAOYSA-N 0.000 claims 1
- IVMJWMMQEULBFZ-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1 IVMJWMMQEULBFZ-UHFFFAOYSA-N 0.000 claims 1
- OLENDFLGSRNPAK-UHFFFAOYSA-N 6-[5-amino-1-(1-prop-2-enoylpyrrolidin-3-yl)imidazo[1,5-c]pyrimidin-3-yl]-N-pyridin-2-ylpyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1N=C(N2C(=NC=CC2=1)N)C1=NC=C(C(=O)NC2=NC=CC=C2)C=C1 OLENDFLGSRNPAK-UHFFFAOYSA-N 0.000 claims 1
- PGSZAJAJXMMDOW-UHFFFAOYSA-N N-(2-chlorophenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=C(C=CC=C2)Cl)C=C1 PGSZAJAJXMMDOW-UHFFFAOYSA-N 0.000 claims 1
- BCZUWLDBTDQWAC-UHFFFAOYSA-N N-(2-fluorophenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=C(C=CC=C2)F)C=C1 BCZUWLDBTDQWAC-UHFFFAOYSA-N 0.000 claims 1
- BERXZACFTNWARG-UHFFFAOYSA-N N-(3-chlorophenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC(=CC=C2)Cl)C=C1 BERXZACFTNWARG-UHFFFAOYSA-N 0.000 claims 1
- VNAPRCLCBYNUGO-UHFFFAOYSA-N N-(3-chloropyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC=C2Cl)C=C1 VNAPRCLCBYNUGO-UHFFFAOYSA-N 0.000 claims 1
- HDBZXDQZEJGZSM-UHFFFAOYSA-N N-(3-cyanophenyl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C#N)C=C1 HDBZXDQZEJGZSM-UHFFFAOYSA-N 0.000 claims 1
- LGZBUJRSECIBGR-UHFFFAOYSA-N N-(3-cyanophenyl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C#N)C=C1 LGZBUJRSECIBGR-UHFFFAOYSA-N 0.000 claims 1
- MMVYYTMDCVKAKN-UHFFFAOYSA-N N-(3-cyanophenyl)-5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)C#N MMVYYTMDCVKAKN-UHFFFAOYSA-N 0.000 claims 1
- OUFDPVLXMFCJTB-UHFFFAOYSA-N N-(3-cyclopropylphenyl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C2CC2)C=C1 OUFDPVLXMFCJTB-UHFFFAOYSA-N 0.000 claims 1
- UHDZRSFNKMUPSC-UHFFFAOYSA-N N-(3-cyclopropylphenyl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC(=CC=C2)C2CC2)C=C1 UHDZRSFNKMUPSC-UHFFFAOYSA-N 0.000 claims 1
- MSWXSXGYZXBRIK-UHFFFAOYSA-N N-(3-cyclopropylphenyl)-5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)C1CC1 MSWXSXGYZXBRIK-UHFFFAOYSA-N 0.000 claims 1
- VVVYKADYLNPCJN-UHFFFAOYSA-N N-(3-cyclopropylphenyl)-5-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)C1CC1 VVVYKADYLNPCJN-UHFFFAOYSA-N 0.000 claims 1
- ZYTTWPGMBMJVTO-UHFFFAOYSA-N N-(3-fluorophenyl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=CC(=CC=C2)F)C=C1 ZYTTWPGMBMJVTO-UHFFFAOYSA-N 0.000 claims 1
- NWLJQJCQKUNUMY-UHFFFAOYSA-N N-(3-fluorophenyl)-5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)F NWLJQJCQKUNUMY-UHFFFAOYSA-N 0.000 claims 1
- ASQDXSORILMNHN-UHFFFAOYSA-N N-(3-fluorophenyl)-5-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC(=CC=C1)F ASQDXSORILMNHN-UHFFFAOYSA-N 0.000 claims 1
- NSZBVGWVDXRRKS-UHFFFAOYSA-N N-(3-fluoropyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC=C2F)C=C1 NSZBVGWVDXRRKS-UHFFFAOYSA-N 0.000 claims 1
- MRAASYIQYXBZTI-UHFFFAOYSA-N N-(3-methylphenyl)-5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC=1C=C(C=CC=1)C MRAASYIQYXBZTI-UHFFFAOYSA-N 0.000 claims 1
- LEKUXNKERZZBFE-UHFFFAOYSA-N N-(3-methylphenyl)-5-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC=1C=C(C=CC=1)C LEKUXNKERZZBFE-UHFFFAOYSA-N 0.000 claims 1
- RNQABRPNMMCKTH-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-2-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F RNQABRPNMMCKTH-UHFFFAOYSA-N 0.000 claims 1
- MHGZPOILOSWDNS-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-2-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F MHGZPOILOSWDNS-UHFFFAOYSA-N 0.000 claims 1
- ZIZFDUMHTASUGQ-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-2-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F ZIZFDUMHTASUGQ-UHFFFAOYSA-N 0.000 claims 1
- LMFBXJXEUKKTSA-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-2-methoxy-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)OC LMFBXJXEUKKTSA-UHFFFAOYSA-N 0.000 claims 1
- XDHAPFLXUHEBRT-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-3-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F XDHAPFLXUHEBRT-UHFFFAOYSA-N 0.000 claims 1
- NVDXYGLCAICPCU-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-3-fluoro-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)F NVDXYGLCAICPCU-UHFFFAOYSA-N 0.000 claims 1
- TWTORNQZBLWXFT-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-3-methoxy-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)OC TWTORNQZBLWXFT-UHFFFAOYSA-N 0.000 claims 1
- XPSVYSLZZUGHRI-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-3-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1)OC XPSVYSLZZUGHRI-UHFFFAOYSA-N 0.000 claims 1
- JOVWQLIWJWSPGZ-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 JOVWQLIWJWSPGZ-UHFFFAOYSA-N 0.000 claims 1
- ZEZTWQWUFCSRNT-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C#N)C=C1 ZEZTWQWUFCSRNT-UHFFFAOYSA-N 0.000 claims 1
- ZJFPJULJVVCESF-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-2-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F ZJFPJULJVVCESF-UHFFFAOYSA-N 0.000 claims 1
- DJELSECHQWQSAZ-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-2-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F DJELSECHQWQSAZ-UHFFFAOYSA-N 0.000 claims 1
- GUEQOBWITMMWDF-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-2-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC(=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)OC GUEQOBWITMMWDF-UHFFFAOYSA-N 0.000 claims 1
- BIEOFUYQVMLAEQ-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-3-fluoro-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F BIEOFUYQVMLAEQ-UHFFFAOYSA-N 0.000 claims 1
- IHVRMTOOHMFMJH-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-3-fluoro-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)F IHVRMTOOHMFMJH-UHFFFAOYSA-N 0.000 claims 1
- VHQHGWLRTCNQTH-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-3-methoxy-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1)OC VHQHGWLRTCNQTH-UHFFFAOYSA-N 0.000 claims 1
- WUDKAYPVZKKDEY-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 WUDKAYPVZKKDEY-UHFFFAOYSA-N 0.000 claims 1
- GAWGIOBITJLZNW-UHFFFAOYSA-N N-(4-cyclopropylpyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C2CC2)C=C1 GAWGIOBITJLZNW-UHFFFAOYSA-N 0.000 claims 1
- QOEMEJVKRSOFCD-UHFFFAOYSA-N N-(4-methoxypyridin-2-yl)-4-[5-(1-prop-2-enoylpyrrolidin-3-yl)pyrrolo[1,2-c]pyrimidin-7-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(N2C=NC=CC2=1)C1=CC=C(C(=O)NC2=NC=CC(=C2)OC)C=C1 QOEMEJVKRSOFCD-UHFFFAOYSA-N 0.000 claims 1
- KPRWTGVTWKXJPF-UHFFFAOYSA-N N-(4-methylpyridin-2-yl)-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=NC=CC(=C2)C)C=C1 KPRWTGVTWKXJPF-UHFFFAOYSA-N 0.000 claims 1
- ZSLPGTSEWBCFPS-UHFFFAOYSA-N N-[3-(2,6-diphenylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)C1=NC2=C(C=C(C=C2C=N1)C1=CC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O ZSLPGTSEWBCFPS-UHFFFAOYSA-N 0.000 claims 1
- DQIWUEZMASOMSY-UHFFFAOYSA-N N-[3-(2-amino-6-phenylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O DQIWUEZMASOMSY-UHFFFAOYSA-N 0.000 claims 1
- JWRRDWPPMZJYSJ-UHFFFAOYSA-N N-[3-(2-amino-8-phenylpurin-9-yl)phenyl]prop-2-enamide Chemical compound NC1=NC=C2N=C(N(C2=N1)C=1C=C(C=CC=1)NC(C=C)=O)C1=CC=CC=C1 JWRRDWPPMZJYSJ-UHFFFAOYSA-N 0.000 claims 1
- KZXUOLDEHVFSKS-UHFFFAOYSA-N N-[3-(2-anilino-6-phenylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)C=1C=C2C=NC(=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)NC1=CC=CC=C1 KZXUOLDEHVFSKS-UHFFFAOYSA-N 0.000 claims 1
- XJBXXMUKGFLZIF-UHFFFAOYSA-N N-[3-(2-anilino-6-pyridin-3-ylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=CC=1)C=1C=C(C=CC=1)NC(C=C)=O XJBXXMUKGFLZIF-UHFFFAOYSA-N 0.000 claims 1
- UDWATZNEZCMEIZ-UHFFFAOYSA-N N-[3-(4-amino-6-phenylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound NC1=NC=NC2=C(C=C(C=C12)C1=CC=CC=C1)C=1C=C(C=CC=1)NC(C=C)=O UDWATZNEZCMEIZ-UHFFFAOYSA-N 0.000 claims 1
- HBMMZDBYTITHHJ-UHFFFAOYSA-N N-[3-(6-phenylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O HBMMZDBYTITHHJ-UHFFFAOYSA-N 0.000 claims 1
- SRVFYFILSFKRDY-UHFFFAOYSA-N N-[3-(6-pyridin-3-ylquinazolin-8-yl)phenyl]prop-2-enamide Chemical compound N1=CC(=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O SRVFYFILSFKRDY-UHFFFAOYSA-N 0.000 claims 1
- CAMFYRHMRNWYRP-UHFFFAOYSA-N N-[3-(8-phenylpurin-9-yl)phenyl]prop-2-enamide Chemical compound C1(=CC=CC=C1)C=1N(C2=NC=NC=C2N=1)C=1C=C(C=CC=1)NC(C=C)=O CAMFYRHMRNWYRP-UHFFFAOYSA-N 0.000 claims 1
- NWFXKCZQPVCADC-UHFFFAOYSA-N N-[3-[2-amino-6-(5-chloropyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC=C(C=1)Cl)C=1C=C(C=CC=1)NC(C=C)=O NWFXKCZQPVCADC-UHFFFAOYSA-N 0.000 claims 1
- XPDLECOFMBFVLG-UHFFFAOYSA-N N-[3-[2-amino-6-(6-methylpyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C=1C=NC(=CC=1)C)C=1C=C(C=CC=1)NC(C=C)=O XPDLECOFMBFVLG-UHFFFAOYSA-N 0.000 claims 1
- UQJKMSOHOGPBFW-UHFFFAOYSA-N N-[3-[2-amino-6-[4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC1=NC2=C(C=C(C=C2C=N1)C1=CC=C(C=C1)OC1=NC=CC(=C1)C(F)(F)F)C=1C=C(C=CC=1)NC(C=C)=O UQJKMSOHOGPBFW-UHFFFAOYSA-N 0.000 claims 1
- MCHOBXCJJBLWPD-UHFFFAOYSA-N N-[3-[5-amino-3-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]imidazo[1,5-c]pyrimidin-1-yl]phenyl]prop-2-enamide Chemical compound NC1=NC=CC=2N1C(=NC=2C=1C=C(C=CC=1)NC(C=C)=O)C1=CC=C(C=C1)OC1=NC=CC=C1C(F)(F)F MCHOBXCJJBLWPD-UHFFFAOYSA-N 0.000 claims 1
- HBNDQDSPRUMKID-UHFFFAOYSA-N N-[3-[6-(2-chlorophenyl)-2-phenylquinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=C(C=CC=C1)C=1C=C2C=NC(=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)C1=CC=CC=C1 HBNDQDSPRUMKID-UHFFFAOYSA-N 0.000 claims 1
- MUVGXJGENMSHIL-UHFFFAOYSA-N N-[3-[6-(2-chlorophenyl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=C(C=CC=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O MUVGXJGENMSHIL-UHFFFAOYSA-N 0.000 claims 1
- IRIBSJIWIZUONZ-UHFFFAOYSA-N N-[3-[6-(6-methylpyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=N1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O IRIBSJIWIZUONZ-UHFFFAOYSA-N 0.000 claims 1
- VIVFDZGQZUQYIC-UHFFFAOYSA-N N-[3-[6-(6-phenoxypyridin-3-yl)quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=N1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O VIVFDZGQZUQYIC-UHFFFAOYSA-N 0.000 claims 1
- DXJFGTOHWAGLLM-UHFFFAOYSA-N N-[3-[6-[2-(trifluoromethyl)pyridin-4-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C1=NC=CC(=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)(F)F DXJFGTOHWAGLLM-UHFFFAOYSA-N 0.000 claims 1
- XPMYWUKWVYIKIY-UHFFFAOYSA-N N-[3-[6-[2-chloro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC1=C(C=CC(=C1)OC1=NC=CC(=C1)C(F)(F)F)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O XPMYWUKWVYIKIY-UHFFFAOYSA-N 0.000 claims 1
- LQBRLGKTAUCUAM-UHFFFAOYSA-N N-[3-[6-[2-fluoro-4-(3-fluoropyridin-2-yl)oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC=C1F)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O LQBRLGKTAUCUAM-UHFFFAOYSA-N 0.000 claims 1
- IKKXKOMVNYZHDG-UHFFFAOYSA-N N-[3-[6-[2-fluoro-4-[4-(trifluoromethyl)pyridin-2-yl]oxyphenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=C(C=CC(=C1)OC1=NC=CC(=C1)C(F)(F)F)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O IKKXKOMVNYZHDG-UHFFFAOYSA-N 0.000 claims 1
- JHUVDFFDVGUWSK-UHFFFAOYSA-N N-[3-[6-[3-(3-cyanoanilino)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C=1C=C(C=CC=1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O JHUVDFFDVGUWSK-UHFFFAOYSA-N 0.000 claims 1
- YCFAMIASKGMQNT-UHFFFAOYSA-N N-[3-[6-[3-(3-cyclopropylanilino)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C1(CC1)C=1C=C(C=CC=1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O YCFAMIASKGMQNT-UHFFFAOYSA-N 0.000 claims 1
- YBMIBLAGRSCFLH-UHFFFAOYSA-N N-[3-[6-[3-[3-(trifluoromethyl)anilino]phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C=1C=C(C=CC=1)NC=1C=C(C=CC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)(F)F YBMIBLAGRSCFLH-UHFFFAOYSA-N 0.000 claims 1
- FPKILVKKFMUZRD-UHFFFAOYSA-N N-[3-[6-[4-(3-chloropyridin-2-yl)oxy-2-fluorophenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound ClC=1C(=NC=CC=1)OC1=CC(=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)F FPKILVKKFMUZRD-UHFFFAOYSA-N 0.000 claims 1
- FWNHBEZAQIDQPF-UHFFFAOYSA-N N-[3-[6-[4-(3-cyanoanilino)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound C(#N)C=1C=C(C=CC=1)NC1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O FWNHBEZAQIDQPF-UHFFFAOYSA-N 0.000 claims 1
- JWAFNHOXNRWALO-UHFFFAOYSA-N N-[3-[6-[4-(morpholine-4-carbonyl)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound N1(CCOCC1)C(=O)C1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O JWAFNHOXNRWALO-UHFFFAOYSA-N 0.000 claims 1
- PTRAMKLVDLMSDR-UHFFFAOYSA-N N-[3-[6-[4-(pyrrolidine-1-carbonyl)phenyl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound N1(CCCC1)C(=O)C1=CC=C(C=C1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O PTRAMKLVDLMSDR-UHFFFAOYSA-N 0.000 claims 1
- OUFMJTFJCZKWLA-UHFFFAOYSA-N N-[3-[6-[5-(trifluoromethyl)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C=1C=C(C=NC=1)C=1C=C2C=NC=NC2=C(C=1)C=1C=C(C=CC=1)NC(C=C)=O)(F)F OUFMJTFJCZKWLA-UHFFFAOYSA-N 0.000 claims 1
- HQCNRHNULPKTMN-UHFFFAOYSA-N N-[3-[6-[6-(3-fluorophenoxy)pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=CC=1 HQCNRHNULPKTMN-UHFFFAOYSA-N 0.000 claims 1
- GUSIVBIRTXSJCV-UHFFFAOYSA-N N-[3-[6-[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC(C=1C=C(OC2=CC=C(C=N2)C=2C=C3C=NC=NC3=C(C=2)C=2C=C(C=CC=2)NC(C=C)=O)C=CC=1)(F)F GUSIVBIRTXSJCV-UHFFFAOYSA-N 0.000 claims 1
- AGEDDDSWTWICQP-UHFFFAOYSA-N N-phenyl-4-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 AGEDDDSWTWICQP-UHFFFAOYSA-N 0.000 claims 1
- DZMJLVWEOLXHFL-UHFFFAOYSA-N N-phenyl-4-[8-[3-(prop-2-enoylamino)phenyl]quinazolin-6-yl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1)C=1C=C(C=C2C=NC=NC=12)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 DZMJLVWEOLXHFL-UHFFFAOYSA-N 0.000 claims 1
- MRPWVGDGCMGFGE-UHFFFAOYSA-N N-phenyl-5-[8-(1-prop-2-enoylpyrrolidin-3-yl)quinazolin-6-yl]pyridine-2-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C=1C=C(C=C2C=NC=NC=12)C=1C=CC(=NC=1)C(=O)NC1=CC=CC=C1 MRPWVGDGCMGFGE-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 11
- 229940043355 kinase inhibitor Drugs 0.000 abstract 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 abstract 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 107
- 102000001301 EGF receptor Human genes 0.000 description 62
- 108060006698 EGF receptor Proteins 0.000 description 62
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 51
- 235000002639 sodium chloride Nutrition 0.000 description 48
- 229910052757 nitrogen Inorganic materials 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 46
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 40
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 108091000080 Phosphotransferase Proteins 0.000 description 32
- 102000020233 phosphotransferase Human genes 0.000 description 32
- 125000005037 alkyl phenyl group Chemical group 0.000 description 27
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 229940117913 acrylamide Drugs 0.000 description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 23
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 23
- 238000009472 formulation Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 101000864342 Homo sapiens Tyrosine-protein kinase BTK Proteins 0.000 description 19
- 102100029823 Tyrosine-protein kinase BTK Human genes 0.000 description 19
- 229960005419 nitrogen Drugs 0.000 description 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 15
- 125000004404 heteroalkyl group Chemical group 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 14
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 13
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 229910006074 SO2NH2 Inorganic materials 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 239000000651 prodrug Substances 0.000 description 12
- 229940002612 prodrug Drugs 0.000 description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 11
- ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 description 11
- 101150029707 ERBB2 gene Proteins 0.000 description 11
- 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 description 11
- 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 description 11
- 101710182389 Fibroblast growth factor receptor 2 Proteins 0.000 description 11
- 102100023600 Fibroblast growth factor receptor 2 Human genes 0.000 description 11
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 description 11
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 description 11
- 125000001246 bromo group Chemical group Br* 0.000 description 11
- 238000000099 in vitro assay Methods 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 239000000546 pharmaceutical excipient Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 9
- 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 9
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 description 9
- 108060006678 I-kappa-B kinase Proteins 0.000 description 9
- 102000001284 I-kappa-B kinase Human genes 0.000 description 9
- 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 description 9
- 101150001535 SRC gene Proteins 0.000 description 9
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 102100033793 ALK tyrosine kinase receptor Human genes 0.000 description 8
- 101000779641 Homo sapiens ALK tyrosine kinase receptor Proteins 0.000 description 8
- 102000001253 Protein Kinase Human genes 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 108060006633 protein kinase Proteins 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 7
- 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 description 7
- 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 description 7
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 description 7
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 description 7
- 108010068342 MAP Kinase Kinase 1 Proteins 0.000 description 7
- 102100034069 MAP kinase-activated protein kinase 2 Human genes 0.000 description 7
- 108010041955 MAP-kinase-activated kinase 2 Proteins 0.000 description 7
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 description 7
- 101150054691 PIM3 gene Proteins 0.000 description 7
- 101150054473 PTK2 gene Proteins 0.000 description 7
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 7
- 101150094745 Ptk2b gene Proteins 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N epoxyketone group Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 7
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 7
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 125000006413 ring segment Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 6
- 101150028321 Lck gene Proteins 0.000 description 6
- 101150058160 Lyn gene Proteins 0.000 description 6
- 101150113474 MAPK10 gene Proteins 0.000 description 6
- 101150031398 MAPK9 gene Proteins 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000004663 cell proliferation Effects 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical group ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 150000003573 thiols Chemical group 0.000 description 6
- KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- KIWODJBCHRADND-UHFFFAOYSA-N 3-anilino-4-[1-[3-(1-imidazolyl)propyl]-3-indolyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C3=CC=CC=C3N(CCCN3C=NC=C3)C=2)=C1NC1=CC=CC=C1 KIWODJBCHRADND-UHFFFAOYSA-N 0.000 description 5
- ZYJSTSMEUKNCEV-UHFFFAOYSA-N 3-diazo-1-diazonioprop-1-en-2-olate Chemical group [N-]=[N+]=CC(=O)C=[N+]=[N-] ZYJSTSMEUKNCEV-UHFFFAOYSA-N 0.000 description 5
- 102100037263 3-phosphoinositide-dependent protein kinase 1 Human genes 0.000 description 5
- 101150107888 AKT2 gene Proteins 0.000 description 5
- 101150019464 ARAF gene Proteins 0.000 description 5
- 101150095401 AURKA gene Proteins 0.000 description 5
- 101150051155 Akt3 gene Proteins 0.000 description 5
- RYVZYACBVYKUHD-UHFFFAOYSA-N Alk5 Natural products CC#CC#CCCCCC=CC(=O)NCC(C)C RYVZYACBVYKUHD-UHFFFAOYSA-N 0.000 description 5
- 101150053778 CSF1R gene Proteins 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 5
- 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 description 5
- 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 5
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 5
- 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 5
- 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 description 5
- 101100503636 Danio rerio fyna gene Proteins 0.000 description 5
- 101100481408 Danio rerio tie2 gene Proteins 0.000 description 5
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical group N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 5
- 102100023266 Dual specificity mitogen-activated protein kinase kinase 2 Human genes 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 108010055196 EphA2 Receptor Proteins 0.000 description 5
- 108010055334 EphB2 Receptor Proteins 0.000 description 5
- 102100030340 Ephrin type-A receptor 2 Human genes 0.000 description 5
- 102100031968 Ephrin type-B receptor 2 Human genes 0.000 description 5
- 102100031983 Ephrin type-B receptor 4 Human genes 0.000 description 5
- 101150004694 Erbb4 gene Proteins 0.000 description 5
- 101100306202 Escherichia coli (strain K12) rpoB gene Proteins 0.000 description 5
- 101150009958 FLT4 gene Proteins 0.000 description 5
- 101150018370 FRK gene Proteins 0.000 description 5
- 101150018272 FYN gene Proteins 0.000 description 5
- 101000600756 Homo sapiens 3-phosphoinositide-dependent protein kinase 1 Proteins 0.000 description 5
- 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 description 5
- 101001055085 Homo sapiens Mitogen-activated protein kinase kinase kinase 9 Proteins 0.000 description 5
- 101001059984 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 4 Proteins 0.000 description 5
- 101001126417 Homo sapiens Platelet-derived growth factor receptor alpha Proteins 0.000 description 5
- 101000669917 Homo sapiens Rho-associated protein kinase 1 Proteins 0.000 description 5
- 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 description 5
- 101000984551 Homo sapiens Tyrosine-protein kinase Blk Proteins 0.000 description 5
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 5
- 101150009057 JAK2 gene Proteins 0.000 description 5
- 101150069380 JAK3 gene Proteins 0.000 description 5
- 108010068353 MAP Kinase Kinase 2 Proteins 0.000 description 5
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 101150024075 Mapk1 gene Proteins 0.000 description 5
- 102100026909 Mitogen-activated protein kinase kinase kinase 9 Human genes 0.000 description 5
- 102100028194 Mitogen-activated protein kinase kinase kinase kinase 4 Human genes 0.000 description 5
- 101100381978 Mus musculus Braf gene Proteins 0.000 description 5
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 5
- 101100306001 Mus musculus Mst1r gene Proteins 0.000 description 5
- 101100481410 Mus musculus Tek gene Proteins 0.000 description 5
- 101100268066 Mus musculus Zap70 gene Proteins 0.000 description 5
- 101150111783 NTRK1 gene Proteins 0.000 description 5
- 101150056950 Ntrk2 gene Proteins 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 102100030485 Platelet-derived growth factor receptor alpha Human genes 0.000 description 5
- 102000001892 Protein Kinase C-theta Human genes 0.000 description 5
- 108010015499 Protein Kinase C-theta Proteins 0.000 description 5
- 102100024924 Protein kinase C alpha type Human genes 0.000 description 5
- 101710109947 Protein kinase C alpha type Proteins 0.000 description 5
- 102100039313 Rho-associated protein kinase 1 Human genes 0.000 description 5
- 102100039314 Rho-associated protein kinase 2 Human genes 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 102100027053 Tyrosine-protein kinase Blk Human genes 0.000 description 5
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 5
- 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001299 aldehydes Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 101150073031 cdk2 gene Proteins 0.000 description 5
- 101150060629 def gene Proteins 0.000 description 5
- IUOALNGUUSBIEJ-UHFFFAOYSA-N diazomethanamine Chemical group NC=[N+]=[N-] IUOALNGUUSBIEJ-UHFFFAOYSA-N 0.000 description 5
- 150000002019 disulfides Chemical group 0.000 description 5
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical group NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 238000000021 kinase assay Methods 0.000 description 5
- 239000002502 liposome Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RQIAYLLGYGPVOH-UHFFFAOYSA-N n-cyanocyclopropanecarboxamide Chemical group N#CNC(=O)C1CC1 RQIAYLLGYGPVOH-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical group NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 4
- 101001059982 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 5 Proteins 0.000 description 4
- 101001120056 Homo sapiens Phosphatidylinositol 3-kinase regulatory subunit alpha Proteins 0.000 description 4
- 101000878540 Homo sapiens Protein-tyrosine kinase 2-beta Proteins 0.000 description 4
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 4
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 4
- 102100028195 Mitogen-activated protein kinase kinase kinase kinase 5 Human genes 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- 102100026169 Phosphatidylinositol 3-kinase regulatory subunit alpha Human genes 0.000 description 4
- 102100037787 Protein-tyrosine kinase 2-beta Human genes 0.000 description 4
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 4
- 101150077555 Ret gene Proteins 0.000 description 4
- 102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 230000033077 cellular process Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 238000006366 phosphorylation reaction Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102100037813 Focal adhesion kinase 1 Human genes 0.000 description 3
- 101000878536 Homo sapiens Focal adhesion kinase 1 Proteins 0.000 description 3
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 3
- 101000729945 Homo sapiens Serine/threonine-protein kinase PLK2 Proteins 0.000 description 3
- 101000691614 Homo sapiens Serine/threonine-protein kinase PLK3 Proteins 0.000 description 3
- 101000582914 Homo sapiens Serine/threonine-protein kinase PLK4 Proteins 0.000 description 3
- 101001050476 Homo sapiens Tyrosine-protein kinase ITK/TSK Proteins 0.000 description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 229920006063 Lamide® Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 102100021733 NUAK family SNF1-like kinase 2 Human genes 0.000 description 3
- 101710151812 NUAK family SNF1-like kinase 2 Proteins 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 3
- 102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 description 3
- 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 description 3
- 206010039491 Sarcoma Diseases 0.000 description 3
- 102100031463 Serine/threonine-protein kinase PLK1 Human genes 0.000 description 3
- 102100031462 Serine/threonine-protein kinase PLK2 Human genes 0.000 description 3
- 102100026209 Serine/threonine-protein kinase PLK3 Human genes 0.000 description 3
- 102100030267 Serine/threonine-protein kinase PLK4 Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 101100234844 Trametes versicolor LCC2 gene Proteins 0.000 description 3
- 102100023345 Tyrosine-protein kinase ITK/TSK Human genes 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 3
- 125000002393 azetidinyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940001468 citrate Drugs 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229940001447 lactate Drugs 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 239000006186 oral dosage form Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000005022 packaging material Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 108010056274 polo-like kinase 1 Proteins 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000037317 transdermal delivery Effects 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- FKBYDGHOPOEEEP-UHFFFAOYSA-N 2-pyridin-2-ylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=N1 FKBYDGHOPOEEEP-UHFFFAOYSA-N 0.000 description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 102100032306 Aurora kinase B Human genes 0.000 description 2
- 102000002427 Cyclin B Human genes 0.000 description 2
- 108010068150 Cyclin B Proteins 0.000 description 2
- 101100457345 Danio rerio mapk14a gene Proteins 0.000 description 2
- 101100457347 Danio rerio mapk14b gene Proteins 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000798306 Homo sapiens Aurora kinase B Proteins 0.000 description 2
- 101000967216 Homo sapiens Eosinophil cationic protein Proteins 0.000 description 2
- 101000852815 Homo sapiens Insulin receptor Proteins 0.000 description 2
- 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 description 2
- 101001051767 Homo sapiens Protein kinase C beta type Proteins 0.000 description 2
- 101000606502 Homo sapiens Protein-tyrosine kinase 6 Proteins 0.000 description 2
- 101000779418 Homo sapiens RAC-alpha serine/threonine-protein kinase Proteins 0.000 description 2
- 101000712530 Homo sapiens RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 description 2
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 description 2
- 101001051706 Homo sapiens Ribosomal protein S6 kinase beta-1 Proteins 0.000 description 2
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
- 101000623857 Homo sapiens Serine/threonine-protein kinase mTOR Proteins 0.000 description 2
- 101000823316 Homo sapiens Tyrosine-protein kinase ABL1 Proteins 0.000 description 2
- 101000912503 Homo sapiens Tyrosine-protein kinase Fgr Proteins 0.000 description 2
- 101001022129 Homo sapiens Tyrosine-protein kinase Fyn Proteins 0.000 description 2
- 101000587313 Homo sapiens Tyrosine-protein kinase Srms Proteins 0.000 description 2
- 101000820294 Homo sapiens Tyrosine-protein kinase Yes Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 102100036721 Insulin receptor Human genes 0.000 description 2
- 108700012928 MAPK14 Proteins 0.000 description 2
- 229940124647 MEK inhibitor Drugs 0.000 description 2
- 101150003941 Mapk14 gene Proteins 0.000 description 2
- 102000054819 Mitogen-activated protein kinase 14 Human genes 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101100523539 Mus musculus Raf1 gene Proteins 0.000 description 2
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 102100038332 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Human genes 0.000 description 2
- 102000018967 Platelet-Derived Growth Factor beta Receptor Human genes 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 108010024526 Protein Kinase C beta Proteins 0.000 description 2
- 102000015766 Protein Kinase C beta Human genes 0.000 description 2
- 102100024923 Protein kinase C beta type Human genes 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 102100039810 Protein-tyrosine kinase 6 Human genes 0.000 description 2
- 102100028286 Proto-oncogene tyrosine-protein kinase receptor Ret Human genes 0.000 description 2
- 101710113459 RAC-alpha serine/threonine-protein kinase Proteins 0.000 description 2
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 2
- 102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 description 2
- 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 2
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 description 2
- 102100024908 Ribosomal protein S6 kinase beta-1 Human genes 0.000 description 2
- 108060006706 SRC Proteins 0.000 description 2
- 102000001332 SRC Human genes 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 102100022596 Tyrosine-protein kinase ABL1 Human genes 0.000 description 2
- 102100026150 Tyrosine-protein kinase Fgr Human genes 0.000 description 2
- 102100035221 Tyrosine-protein kinase Fyn Human genes 0.000 description 2
- 102100029654 Tyrosine-protein kinase Srms Human genes 0.000 description 2
- 102100021788 Tyrosine-protein kinase Yes Human genes 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000005441 aurora Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 210000003679 cervix uteri Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 229960002086 dextran Drugs 0.000 description 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 2
- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 2
- 125000000597 dioxinyl group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940079360 enema for constipation Drugs 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 2
- 125000003838 furazanyl group Chemical group 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 210000000244 kidney pelvis Anatomy 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NCEXCXGPAUUSLF-UHFFFAOYSA-N n-(4-methoxypyridin-2-yl)benzamide Chemical compound COC1=CC=NC(NC(=O)C=2C=CC=CC=2)=C1 NCEXCXGPAUUSLF-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 210000003800 pharynx Anatomy 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 102220079512 rs143258862 Human genes 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229940086735 succinate Drugs 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 2
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XETLOFNELZCXMX-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenylacetate;hydrochloride Chemical compound Cl.C1=CC(OCCCCCC)=CC=C1C(O)(C(=O)OCCN(CC)CC)C1=CC=CC=C1 XETLOFNELZCXMX-UHFFFAOYSA-N 0.000 description 1
- HNLXNOZHXNSSPN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCOCCOCCOCCO)C=C1 HNLXNOZHXNSSPN-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- IVHKZCSZELZKSJ-UHFFFAOYSA-N 2-hydroxyethyl sulfonate Chemical compound OCCOS(=O)=O IVHKZCSZELZKSJ-UHFFFAOYSA-N 0.000 description 1
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 125000004606 5,6,7,8-tetrahydroisoquinolinyl group Chemical group C1(=NC=CC=2CCCCC12)* 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004155 Chlorine dioxide Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
- 101000940468 Drosophila melanogaster COP9 signalosome complex subunit 2 Proteins 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 229920001499 Heparinoid Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- 241001580017 Jana Species 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 208000003445 Mouth Neoplasms Diseases 0.000 description 1
- 102000007474 Multiprotein Complexes Human genes 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 108030005449 Polo kinases Proteins 0.000 description 1
- 229920000148 Polycarbophil calcium Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
- 229920002807 Thiomer Polymers 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229940040563 agaric acid Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000003080 antimitotic agent Substances 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960000997 bicalutamide Drugs 0.000 description 1
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 125000005510 but-1-en-2-yl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000019398 chlorine dioxide Nutrition 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940046044 combinations of antineoplastic agent Drugs 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- CFCUWKMKBJTWLW-UHFFFAOYSA-N deoliosyl-3C-alpha-L-digitoxosyl-MTM Natural products CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1O)CC1OC1CC(O)C(O)C(C)O1 CFCUWKMKBJTWLW-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229960000633 dextran sulfate Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 229940069417 doxy Drugs 0.000 description 1
- HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 description 1
- 229950004203 droloxifene Drugs 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000005699 fluoropyrimidines Chemical class 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000002554 heparinoid Substances 0.000 description 1
- 229940025770 heparinoids Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 210000003228 intrahepatic bile duct Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000007914 intraventricular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 201000000564 macroglobulinemia Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LZIJKEIPCFEOLH-UHFFFAOYSA-N n-pyridin-2-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=N1 LZIJKEIPCFEOLH-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229920004905 octoxynol-10 Polymers 0.000 description 1
- 229920004914 octoxynol-40 Polymers 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 229940043138 pentosan polysulfate Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011129 pharmaceutical packaging material Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229950005134 polycarbophil Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000955 prescription drug Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000029983 protein stabilization Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000000541 pulsatile effect Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 229960004622 raloxifene Drugs 0.000 description 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 210000004994 reproductive system Anatomy 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound 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 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229960004906 thiomersal Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- PLHJCIYEEKOWNM-HHHXNRCGSA-N tipifarnib Chemical compound CN1C=NC=C1[C@](N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-HHHXNRCGSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- 239000012443 tonicity enhancing agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 238000012447 xenograft mouse model Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- 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
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D403/02—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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662375382P | 2016-08-15 | 2016-08-15 | |
| US62/375,382 | 2016-08-15 | ||
| PCT/US2017/046819 WO2018035061A1 (en) | 2016-08-15 | 2017-08-14 | Certain chemical entities, compositions, and methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3033370A1 true CA3033370A1 (en) | 2018-02-22 |
Family
ID=61196987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3033370A Pending CA3033370A1 (en) | 2016-08-15 | 2017-08-14 | Certain chemical entities, compositions, and methods |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US10544106B2 (enExample) |
| EP (2) | EP4006035B1 (enExample) |
| JP (2) | JP7101165B2 (enExample) |
| CN (1) | CN109843858B (enExample) |
| AU (1) | AU2017312561B2 (enExample) |
| CA (1) | CA3033370A1 (enExample) |
| WO (1) | WO2018035061A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014308616B2 (en) | 2013-08-23 | 2018-12-06 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| US10947201B2 (en) | 2015-02-17 | 2021-03-16 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| EP4006035B1 (en) | 2016-08-15 | 2023-11-22 | Neupharma, Inc. | Quinazoline derivatives as tyrosine kinase inhibitors for the treatment of cancer |
| CN110386921A (zh) * | 2018-04-23 | 2019-10-29 | 南京药捷安康生物科技有限公司 | 成纤维细胞生长因子受体抑制剂化合物 |
| WO2020097398A1 (en) | 2018-11-07 | 2020-05-14 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| CN111574521A (zh) * | 2019-02-18 | 2020-08-25 | 深圳市塔吉瑞生物医药有限公司 | 取代的芳香稠合环衍生物及其组合物及用途 |
| MA56022A (fr) * | 2019-05-31 | 2022-04-06 | Chiesi Farm Spa | Dérivés d'amino quinazoline servant d'inhibiteurs de p2x3 |
| CN110724143B (zh) * | 2019-10-09 | 2021-03-23 | 清华大学 | 一种靶向btk蛋白降解化合物的制备及其在治疗自身免疫系统疾病与肿瘤中的应用 |
| GB201915831D0 (en) * | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
| WO2021102361A1 (en) * | 2019-11-22 | 2021-05-27 | The Regents Of The University Of California | Caspase 6 inhibitors and uses thereof |
| WO2021102299A1 (en) * | 2019-11-22 | 2021-05-27 | The Regents Of The University Of California | Caspase 6 inhibitors and uses thereof |
| WO2021138391A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Indazole compounds |
| WO2021198981A1 (en) | 2020-04-01 | 2021-10-07 | Janssen Biopharma, Inc. | Antiviral compounds and uses thereof |
| CA3181537A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| CN115916759B (zh) * | 2020-06-19 | 2025-07-15 | 泰州红云制药有限公司 | 取代喹唑啉类化合物、其制备方法、药物组合及应用 |
| CN115836070B (zh) * | 2020-08-10 | 2024-08-09 | 上海和誉生物医药科技有限公司 | 作为egfr抑制剂的稠环化合物及其制备方法和应用 |
| CN115956080B (zh) * | 2020-08-17 | 2025-07-11 | 贝达药业股份有限公司 | 双环化合物，包含其的组合物及其应用 |
| WO2022053000A1 (zh) * | 2020-09-10 | 2022-03-17 | 四川海思科制药有限公司 | 一种碳环酰胺衍生物及其在医药上的应用 |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| US20240100172A1 (en) | 2020-12-21 | 2024-03-28 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| WO2022140527A1 (en) | 2020-12-23 | 2022-06-30 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| 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 |
| CA3234638A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| TW202325289A (zh) | 2021-11-09 | 2023-07-01 | 美商雅捷可斯治療公司 | Ｊａｋ２抑制劑之形式及組合物 |
| 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 |
| JP3696884B2 (ja) | 1994-03-25 | 2005-09-21 | アイソテクニカ、インコーポレーテッド | ジュウテリウム化による薬物の効能の増強 |
| 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 |
| BR9707425A (pt) | 1996-02-12 | 1999-07-20 | Univ Rutgers | Composto processo terapêutico para inibir o crescimento de células cancerosas e processo para utilizar o composto |
| WO1997030035A1 (en) | 1996-02-13 | 1997-08-21 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| PT885198E (pt) | 1996-03-05 | 2002-06-28 | Astrazeneca Ab | Derivados de 4-anilinoquinazolina |
| 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 |
| EP1054012B1 (en) | 1998-01-05 | 2003-06-11 | 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 |
| BRPI0017548B8 (pt) | 1999-02-10 | 2023-05-02 | Astrazeneca Ab | Composto |
| CA2376835C (en) | 1999-07-02 | 2009-09-15 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| ATE339406T1 (de) | 1999-09-23 | 2006-10-15 | Astrazeneca Ab | Chinazoline verbindungen als heilmittel |
| AU2001258628A1 (en) | 2000-05-31 | 2001-12-11 | 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 |
| MXPA02012905A (es) | 2000-07-07 | 2004-07-30 | Angiogene Pharm Ltd | Derivados de colquinol como agentes de dano vascular.. |
| BR0112225A (pt) | 2000-07-07 | 2003-05-06 | Angiogene Pharm Ltd | Composto, composição farmacêutica, uso de um composto, e, processo papa preparar um composto |
| UA80295C2 (en) | 2002-09-06 | 2007-09-10 | Biogen Inc | Pyrazolopyridines and using the same |
| AU2004222387A1 (en) * | 2003-03-13 | 2004-09-30 | Synta Pharmaceuticals Corp. | Fused pyrrole compounds |
| WO2005032481A2 (en) | 2003-09-30 | 2005-04-14 | Scios Inc. | Quinazoline derivatives as medicaments |
| CA2577588C (en) | 2004-10-29 | 2013-09-10 | Tibotec Pharmaceuticals Ltd. | 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 |
| AR060358A1 (es) | 2006-04-06 | 2008-06-11 | Novartis Vaccines & Diagnostic | Quinazolinas para la inhibicion de pdk 1 |
| TWI389893B (zh) | 2007-07-06 | 2013-03-21 | Astellas Pharma Inc | 二（芳胺基）芳基化合物 |
| EP2269993B1 (en) | 2008-04-23 | 2013-02-27 | Kyowa Hakko Kirin Co., Ltd. | 2-aminoquinazoline derivative |
| WO2010019762A1 (en) | 2008-08-13 | 2010-02-18 | Jenrin Discovery | 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 |
| BR112012008019A2 (pt) | 2009-10-07 | 2016-03-01 | Sloan Kettering Inst Cancer | derivados de purina úteis como inibidores de hsp90 |
| US7741330B1 (en) | 2009-10-12 | 2010-06-22 | 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 |
| CN103889962B (zh) | 2011-04-01 | 2017-05-03 | 犹他大学研究基金会 | 作为受体酪氨酸激酶btk抑制剂的取代的n‑(3‑(嘧啶‑4‑基)苯基)丙烯酰胺类似物 |
| WO2013005157A1 (en) | 2011-07-05 | 2013-01-10 | Lupin Limited | Sulfone derivatives and their use as pkm2 modulators for the treatment of cancer |
| US8796289B2 (en) | 2011-07-19 | 2014-08-05 | Abbvie Inc. | Pyridazino[4,5-D]pyrimidin-5(6H)-one inhibitors of kinases |
| PT3009431T (pt) | 2011-07-27 | 2017-12-26 | Astrazeneca Ab | Compostos de 2-(2,4,5-anilino-substituídos)pirimidina como moduladores úteis do egfr para o tratamento do cancro |
| ES2725790T3 (es) | 2011-08-26 | 2019-09-27 | Neupharma Inc | Algunas entidades químicas, composiciones, y métodos |
| WO2013040515A1 (en) | 2011-09-14 | 2013-03-21 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| WO2013106792A1 (en) | 2012-01-13 | 2013-07-18 | Acea Biosciences Inc. | Heterocyclic compounds and uses as anticancer agents. |
| TW201336847A (zh) | 2012-02-07 | 2013-09-16 | Taiho Pharmaceutical Co Ltd | 喹啉基吡咯并嘧啶化合物或其鹽 |
| US9394297B2 (en) | 2012-02-28 | 2016-07-19 | Amgen Inc. | Amides as pim inhibitors |
| US8802697B2 (en) | 2012-07-11 | 2014-08-12 | Blueprint Medicines Corporation | Inhibitors of the fibroblast growth factor receptor |
| 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 |
| NZ706857A (en) | 2012-09-28 | 2018-05-25 | Ignyta 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 |
| WO2014130693A1 (en) | 2013-02-25 | 2014-08-28 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
| WO2014135245A1 (en) | 2013-03-05 | 2014-09-12 | Merck Patent Gmbh | 9-(aryl or heteroaryl)-2-(pyrazolyl, pyrrolidinyl or cyclopentyl)aminopurine derivatives as anticancer agents |
| EP3342770B1 (en) | 2013-03-06 | 2022-03-30 | AstraZeneca AB | Quinazoline inhibitors of activating mutant forms of epidermal growth factor receptor |
| WO2014180524A1 (en) | 2013-05-06 | 2014-11-13 | 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 |
| AU2014287016B2 (en) | 2013-07-11 | 2018-11-01 | Acea Biosciences Inc. | Pyrimidine derivatives as kinase inhibitors |
| CN105452257B (zh) | 2013-08-12 | 2017-09-05 | 大鹏药品工业株式会社 | 新型稠合嘧啶化合物或其盐 |
| AU2014308616B2 (en) * | 2013-08-23 | 2018-12-06 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| US20160272645A1 (en) | 2013-10-18 | 2016-09-22 | Medivation Technologies, Inc. | Heterocyclic Compounds and Methods of Use |
| GB201404987D0 (en) | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| KR20170003688A (ko) | 2014-05-14 | 2017-01-09 | 더 리젠츠 오브 더 유니버시티 오브 콜로라도, 어 바디 코포레이트 | 단백질 탈아세틸화효소 억제제 및 이중 단백질 탈아세틸화효소-단백질 키나제 억제제로서의 헤테로사이클릭 하이드록삼산 및 그 이용 방법 |
| 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 |
| TW201613644A (en) | 2014-06-17 | 2016-04-16 | Acerta Pharma Bv | 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 |
| CA2959602A1 (en) | 2014-08-01 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| EP3242878B1 (en) | 2015-01-08 | 2020-10-14 | Impetis Biosciences Ltd. | 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 |
| US10947201B2 (en) | 2015-02-17 | 2021-03-16 | 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 |
| EP4006035B1 (en) | 2016-08-15 | 2023-11-22 | Neupharma, Inc. | Quinazoline derivatives as tyrosine kinase inhibitors for the treatment of cancer |
-
2017
- 2017-08-14 EP EP21201676.0A patent/EP4006035B1/en active Active
- 2017-08-14 US US15/676,852 patent/US10544106B2/en active Active
- 2017-08-14 JP JP2019508173A patent/JP7101165B2/ja active Active
- 2017-08-14 AU AU2017312561A patent/AU2017312561B2/en active Active
- 2017-08-14 WO PCT/US2017/046819 patent/WO2018035061A1/en not_active Ceased
- 2017-08-14 EP EP17841949.5A patent/EP3497087B1/en active Active
- 2017-08-14 CA CA3033370A patent/CA3033370A1/en active Pending
- 2017-08-14 CN CN201780063561.8A patent/CN109843858B/zh active Active
-
2019
- 2019-12-04 US US16/702,936 patent/US11208388B2/en active Active
-
2021
- 2021-10-20 US US17/506,367 patent/US12018002B2/en active Active
-
2022
- 2022-02-07 JP JP2022017081A patent/JP2022058912A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2017312561B2 (en) | 2022-06-30 |
| US10544106B2 (en) | 2020-01-28 |
| EP3497087A1 (en) | 2019-06-19 |
| US20230043970A1 (en) | 2023-02-09 |
| AU2017312561A1 (en) | 2019-03-07 |
| JP2022058912A (ja) | 2022-04-12 |
| CN109843858A (zh) | 2019-06-04 |
| EP3497087B1 (en) | 2021-11-10 |
| US12018002B2 (en) | 2024-06-25 |
| WO2018035061A1 (en) | 2018-02-22 |
| JP2019526550A (ja) | 2019-09-19 |
| US20200172495A1 (en) | 2020-06-04 |
| EP4006035A1 (en) | 2022-06-01 |
| JP7101165B2 (ja) | 2022-07-14 |
| EP3497087A4 (en) | 2020-07-29 |
| EP4006035B1 (en) | 2023-11-22 |
| US20180072688A1 (en) | 2018-03-15 |
| CN109843858B (zh) | 2023-05-05 |
| US11208388B2 (en) | 2021-12-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US12018002B2 (en) | Certain chemical entities, compositions, and methods | |
| US12403145B2 (en) | Substituted quinazolines for inhibiting kinase activity | |
| EP3332785B1 (en) | Certain chemical entities, compositions, and methods | |
| EP2916838B1 (en) | Certain chemical entities, compositions, and methods | |
| HK1226939B (en) | Certain chemical entities, compositions, and methods |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20220719 |
|
| EEER | Examination request |
Effective date: 20220719 |
|
| EEER | Examination request |
Effective date: 20220719 |
|
| EEER | Examination request |
Effective date: 20220719 |
|
| EEER | Examination request |
Effective date: 20220719 |