CA2934709C - Serine/threonine kinase inhibitors - Google Patents

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Publication number

CA2934709C

CA2934709C CA2934709A CA2934709A CA2934709C CA 2934709 C CA2934709 C CA 2934709C CA 2934709 A CA2934709 A CA 2934709A CA 2934709 A CA2934709 A CA 2934709A CA 2934709 C CA2934709 C CA 2934709C

Authority

CA

Canada

Prior art keywords

pyrazol

pyridin

triazolo

amine

methyl

Prior art date

2013-12-30

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.)

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• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 title description 3
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 title description 3
• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 80
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 201000010099 disease Diseases 0.000 claims abstract description 57
• 238000011282 treatment Methods 0.000 claims abstract description 51
• -1 adamantanyl Chemical group 0.000 claims description 1243
• 229910052736 halogen Inorganic materials 0.000 claims description 436
• 150000002367 halogens Chemical class 0.000 claims description 436
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 194
• 239000000203 mixture Substances 0.000 claims description 149
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 143
• 125000000217 alkyl group Chemical group 0.000 claims description 139
• 229910052739 hydrogen Inorganic materials 0.000 claims description 122
• 239000001257 hydrogen Substances 0.000 claims description 121
• 125000005842 heteroatom Chemical group 0.000 claims description 111
• 125000000623 heterocyclic group Chemical group 0.000 claims description 106
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 85
• 125000001072 heteroaryl group Chemical group 0.000 claims description 65
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 65
• 125000004043 oxo group Chemical group O=* 0.000 claims description 64
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 63
• 230000003463 hyperproliferative effect Effects 0.000 claims description 45
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
• 206010028980 Neoplasm Diseases 0.000 claims description 43
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 39
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 38
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims description 34
• 201000011510 cancer Diseases 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 239000003814 drug Substances 0.000 claims description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 26
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
• 208000027866 inflammatory disease Diseases 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 21
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 20
• MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 19
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 229910052731 fluorine Chemical group 0.000 claims description 18
• 239000011737 fluorine Chemical group 0.000 claims description 18
• 239000003085 diluting agent Substances 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 239000003937 drug carrier Substances 0.000 claims description 16
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 10
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 10
• 206010006187 Breast cancer Diseases 0.000 claims description 9
• 201000009030 Carcinoma Diseases 0.000 claims description 9
• 206010009944 Colon cancer Diseases 0.000 claims description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 9
• 206010033128 Ovarian cancer Diseases 0.000 claims description 9
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 9
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 201000005202 lung cancer Diseases 0.000 claims description 9
• 208000020816 lung neoplasm Diseases 0.000 claims description 9
• 201000001441 melanoma Diseases 0.000 claims description 9
• 201000002528 pancreatic cancer Diseases 0.000 claims description 9
• 201000002510 thyroid cancer Diseases 0.000 claims description 9
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 8
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
• 229910052702 rhenium Inorganic materials 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 6
• 206010038389 Renal cancer Diseases 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 6
• 229940127089 cytotoxic agent Drugs 0.000 claims description 6
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 6
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
• 206010005003 Bladder cancer Diseases 0.000 claims description 5
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
• 206010039491 Sarcoma Diseases 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 201000010982 kidney cancer Diseases 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 5
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 5
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 4
• 208000003200 Adenoma Diseases 0.000 claims description 4
• 206010001233 Adenoma benign Diseases 0.000 claims description 4
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
• 208000017604 Hodgkin disease Diseases 0.000 claims description 4
• 206010023347 Keratoacanthoma Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 4
• 206010029260 Neuroblastoma Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 201000010536 head and neck cancer Diseases 0.000 claims description 4
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
• 208000003849 large cell carcinoma Diseases 0.000 claims description 4
• 208000025113 myeloid leukemia Diseases 0.000 claims description 4
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 201000010198 papillary carcinoma Diseases 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 201000001275 rectum cancer Diseases 0.000 claims description 4
• 201000000849 skin cancer Diseases 0.000 claims description 4
• 208000000649 small cell carcinoma Diseases 0.000 claims description 4
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 4
• 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
• 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000005917 3-methylpentyl group Chemical group 0.000 claims description 3
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 208000008035 Back Pain Diseases 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000008930 Low Back Pain Diseases 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
• 208000029742 colonic neoplasm Diseases 0.000 claims description 3
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 3
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 201000003068 rheumatic fever Diseases 0.000 claims description 3
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 3
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
• UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
• 125000005605 benzo group Chemical group 0.000 claims description 2
• 210000001072 colon Anatomy 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 200
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 13
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
• 150000002431 hydrogen Chemical class 0.000 claims 6
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 5
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• 208000003174 Brain Neoplasms Diseases 0.000 claims 3
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims 3
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 3
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• 206010057644 Testis cancer Diseases 0.000 claims 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
• 201000003120 testicular cancer Diseases 0.000 claims 3
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
• 238000011260 co-administration Methods 0.000 claims 2
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
• NODLZCJDRXTSJO-UHFFFAOYSA-N 1,3-dimethylpyrazole Chemical compound CC=1C=CN(C)N=1 NODLZCJDRXTSJO-UHFFFAOYSA-N 0.000 claims 1
• 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
• NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims 1
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
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