CA3092362A1 - Composes de picolinamide - Google Patents
Composes de picolinamide Download PDFInfo
- Publication number
- CA3092362A1 CA3092362A1 CA3092362A CA3092362A CA3092362A1 CA 3092362 A1 CA3092362 A1 CA 3092362A1 CA 3092362 A CA3092362 A CA 3092362A CA 3092362 A CA3092362 A CA 3092362A CA 3092362 A1 CA3092362 A1 CA 3092362A1
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- compound
- cyclobutyl
- pharmaceutically acceptable
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 169
- 201000011510 cancer Diseases 0.000 claims abstract description 152
- 150000003839 salts Chemical class 0.000 claims abstract description 118
- 239000012453 solvate Substances 0.000 claims abstract description 44
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 38
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 38
- 206010009944 Colon cancer Diseases 0.000 claims abstract description 38
- 206010033128 Ovarian cancer Diseases 0.000 claims abstract description 38
- 206010061535 Ovarian neoplasm Diseases 0.000 claims abstract description 38
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims abstract description 38
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims abstract description 38
- 201000002528 pancreatic cancer Diseases 0.000 claims abstract description 38
- 208000008443 pancreatic carcinoma Diseases 0.000 claims abstract description 38
- 206010005003 Bladder cancer Diseases 0.000 claims abstract description 37
- 206010008342 Cervix carcinoma Diseases 0.000 claims abstract description 37
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 37
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 37
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 37
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims abstract description 37
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims abstract description 37
- 201000010881 cervical cancer Diseases 0.000 claims abstract description 37
- 208000029742 colonic neoplasm Diseases 0.000 claims abstract description 37
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims abstract description 37
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims abstract description 37
- 201000005202 lung cancer Diseases 0.000 claims abstract description 37
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 37
- 201000005112 urinary bladder cancer Diseases 0.000 claims abstract description 37
- 201000001441 melanoma Diseases 0.000 claims abstract description 27
- 208000005718 Stomach Neoplasms Diseases 0.000 claims abstract description 25
- 206010017758 gastric cancer Diseases 0.000 claims abstract description 25
- 208000005017 glioblastoma Diseases 0.000 claims abstract description 25
- 201000010536 head and neck cancer Diseases 0.000 claims abstract description 25
- 208000014829 head and neck neoplasm Diseases 0.000 claims abstract description 25
- 201000011549 stomach cancer Diseases 0.000 claims abstract description 25
- 206010004146 Basal cell carcinoma Diseases 0.000 claims abstract description 24
- 206010005949 Bone cancer Diseases 0.000 claims abstract description 24
- 208000018084 Bone neoplasm Diseases 0.000 claims abstract description 24
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims abstract description 24
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims abstract description 24
- 208000003445 Mouth Neoplasms Diseases 0.000 claims abstract description 24
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims abstract description 24
- 208000006265 Renal cell carcinoma Diseases 0.000 claims abstract description 24
- 208000009956 adenocarcinoma Diseases 0.000 claims abstract description 24
- 201000004101 esophageal cancer Diseases 0.000 claims abstract description 24
- 201000002313 intestinal cancer Diseases 0.000 claims abstract description 24
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims abstract description 24
- 206010041823 squamous cell carcinoma Diseases 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 45
- 210000004027 cell Anatomy 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 230000035755 proliferation Effects 0.000 claims description 12
- 210000003289 regulatory T cell Anatomy 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 230000003247 decreasing effect Effects 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- KHVYCBFOIAUCGZ-UHFFFAOYSA-N N-ethyl-4-[4-[1-[(2-methoxypyrimidin-5-yl)carbamoyl]cyclobutyl]phenyl]pyridine-2-carboxamide Chemical compound C(C)NC(C1=NC=CC(=C1)C1=CC=C(C=C1)C1(CCC1)C(NC=1C=NC(=NC=1)OC)=O)=O KHVYCBFOIAUCGZ-UHFFFAOYSA-N 0.000 claims description 3
- RLRAXSAMTMWWJG-UHFFFAOYSA-N N-methyl-4-[4-[1-(pyridin-3-ylcarbamoyl)cyclobutyl]phenyl]pyridine-2-carboxamide Chemical compound CNC(C1=NC=CC(=C1)C1=CC=C(C=C1)C1(CCC1)C(NC=1C=NC=CC=1)=O)=O RLRAXSAMTMWWJG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- RQLTWUWDQBSRON-UHFFFAOYSA-N N-methyl-4-[4-[1-(pyridin-2-ylcarbamoyl)cyclobutyl]phenyl]pyridine-2-carboxamide Chemical compound CNC(C1=NC=CC(=C1)C1=CC=C(C=C1)C1(CCC1)C(NC1=NC=CC=C1)=O)=O RQLTWUWDQBSRON-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- VPVSGTHVAINJFY-UHFFFAOYSA-N 4-[4-[1-[(2-ethylpyrimidin-5-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound C(C)C1=NC=C(C=N1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC VPVSGTHVAINJFY-UHFFFAOYSA-N 0.000 claims 1
- ZVQQLZKOMAURGB-FIBGUPNXSA-N 4-[4-[1-[(2-methoxypyrimidin-5-yl)carbamoyl]cyclobutyl]phenyl]-N-(trideuteriomethyl)pyridine-2-carboxamide Chemical compound COC1=NC=C(C=N1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC([2H])([2H])[2H] ZVQQLZKOMAURGB-FIBGUPNXSA-N 0.000 claims 1
- DNMHXVAZGKNWFC-UHFFFAOYSA-N 4-[4-[1-[(5-bromopyridin-2-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound BrC=1C=CC(=NC=1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC DNMHXVAZGKNWFC-UHFFFAOYSA-N 0.000 claims 1
- SPDWAJXBYNSJNZ-UHFFFAOYSA-N 4-[4-[1-[(5-chloropyridin-2-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound ClC=1C=CC(=NC=1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC SPDWAJXBYNSJNZ-UHFFFAOYSA-N 0.000 claims 1
- LWYXBFYLULOKMH-UHFFFAOYSA-N 4-[4-[1-[(5-chloropyrimidin-2-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound ClC=1C=NC(=NC=1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC LWYXBFYLULOKMH-UHFFFAOYSA-N 0.000 claims 1
- BPPOVGYMGFIEOM-UHFFFAOYSA-N 4-[4-[1-[(5-cyanopyrimidin-2-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=NC(=NC=1)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC BPPOVGYMGFIEOM-UHFFFAOYSA-N 0.000 claims 1
- LGEIVWDCLIVPBA-UHFFFAOYSA-N 4-[4-[1-[(5-fluoro-6-methoxypyridin-3-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound FC=1C=C(C=NC=1OC)NC(=O)C1(CCC1)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC LGEIVWDCLIVPBA-UHFFFAOYSA-N 0.000 claims 1
- OPLOKTZOEALHKM-UHFFFAOYSA-N 4-[4-[3,3-difluoro-1-[(2-methoxypyrimidin-5-yl)carbamoyl]cyclobutyl]phenyl]-N-methylpyridine-2-carboxamide Chemical compound FC1(CC(C1)(C(NC=1C=NC(=NC=1)OC)=O)C1=CC=C(C=C1)C1=CC(=NC=C1)C(=O)NC)F OPLOKTZOEALHKM-UHFFFAOYSA-N 0.000 claims 1
- OFHSYXBHXUVSAW-UHFFFAOYSA-N 4-[6-[1-[(2-methoxypyrimidin-5-yl)carbamoyl]cyclobutyl]pyridin-3-yl]-N-methylpyridine-2-carboxamide Chemical compound COC1=NC=C(C=N1)NC(=O)C1(CCC1)C1=CC=C(C=N1)C1=CC(=NC=C1)C(=O)NC OFHSYXBHXUVSAW-UHFFFAOYSA-N 0.000 claims 1
- DKNLLRJGHLWWGU-UHFFFAOYSA-N 4-[6-[1-[(5-chloropyrimidin-2-yl)carbamoyl]cyclobutyl]pyridin-3-yl]-N-methylpyridine-2-carboxamide Chemical compound ClC=1C=NC(=NC=1)NC(=O)C1(CCC1)C1=CC=C(C=N1)C1=CC(=NC=C1)C(=O)NC DKNLLRJGHLWWGU-UHFFFAOYSA-N 0.000 claims 1
- OEDKANYIHIEUIU-UHFFFAOYSA-N N-cyclopropyl-4-[4-[1-[(2-methoxypyrimidin-5-yl)carbamoyl]cyclobutyl]phenyl]pyridine-2-carboxamide Chemical compound C1(CC1)NC(C1=NC=CC(=C1)C1=CC=C(C=C1)C1(CCC1)C(NC=1C=NC(=NC=1)OC)=O)=O OEDKANYIHIEUIU-UHFFFAOYSA-N 0.000 claims 1
- BVUJGTOLSTZFRW-UHFFFAOYSA-N N-methyl-4-[4-[1-[(3-methyl-1,2-oxazol-5-yl)carbamoyl]cyclobutyl]phenyl]pyridine-2-carboxamide Chemical compound CNC(C1=NC=CC(=C1)C1=CC=C(C=C1)C1(CCC1)C(NC1=CC(=NO1)C)=O)=O BVUJGTOLSTZFRW-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract description 3
- -1 for example Chemical group 0.000 description 110
- 239000000203 mixture Substances 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000010410 layer Substances 0.000 description 15
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 125000001246 bromo group Chemical group Br* 0.000 description 13
- 125000001153 fluoro group Chemical group F* 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- NXWBOAQGGZVKBT-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1C[CH]C1 NXWBOAQGGZVKBT-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 12
- 101001037256 Homo sapiens Indoleamine 2,3-dioxygenase 1 Proteins 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 102100040061 Indoleamine 2,3-dioxygenase 1 Human genes 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 9
- YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical compound C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
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- 125000002393 azetidinyl group Chemical group 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 6
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- 125000002950 monocyclic group Chemical group 0.000 description 6
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
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- 125000003386 piperidinyl group Chemical group 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 102000008096 B7-H1 Antigen Human genes 0.000 description 5
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La présente invention concerne de nouveaux composés de formule (I) et des sels pharmaceutiquement acceptables, des solvates, des solvates du sel de ceux-ci, utiles dans la prévention (par exemple, retarder l'apparition ou réduire le risque de développement) et le traitement (par exemple, maîtriser, soulager ou ralentir la progression) du cancer, y compris le glioblastome, le cancer de l'os, le cancer de la tête et du cou, le mélanome, le carcinome basocellulaire, le carcinome des cellules squameuses, l'adénocarcinome, le cancer buccal, le cancer de l'sophage, le cancer gastrique, le cancer du côlon, le cancer de la vessie, le carcinome hépatocellulaire, le carcinome des cellules rénales, le cancer du pancréas, le cancer de l'ovaire, le cancer du col de l'utérus, le cancer du poumon, le cancer du sein et le cancer de la prostate. Les composés de formule (I), ou leurs sels pharmaceutiquement acceptables, sont des inhibiteurs de l'IDO.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201762574583P | 2017-10-19 | 2017-10-19 | |
US62/574,583 | 2017-10-19 | ||
PCT/US2018/056539 WO2019079614A1 (fr) | 2017-10-19 | 2018-10-18 | Composés de picolinamide |
Publications (1)
Publication Number | Publication Date |
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CA3092362A1 true CA3092362A1 (fr) | 2019-04-25 |
Family
ID=66174302
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA3092362A Abandoned CA3092362A1 (fr) | 2017-10-19 | 2018-10-18 | Composes de picolinamide |
Country Status (3)
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EP (1) | EP3735410A4 (fr) |
CA (1) | CA3092362A1 (fr) |
WO (1) | WO2019079614A1 (fr) |
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BR112022026397A2 (pt) * | 2020-06-23 | 2023-03-14 | Chemocentryx Inc | Métodos para tratar câncer usando derivados de amida de heteroaril-bifenila |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006012227A2 (fr) * | 2004-06-24 | 2006-02-02 | Incyte Corporation | Composes amido et utilisations de ces derniers en tant que produits pharmaceutiques |
US8034940B2 (en) * | 2006-08-09 | 2011-10-11 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
EP2493862B1 (fr) * | 2009-10-28 | 2016-10-05 | Newlink Genetics Corporation | Dérivés imidazole comme inhibiteurs de l'ido |
EP2651930B1 (fr) * | 2010-12-16 | 2015-10-28 | Boehringer Ingelheim International GmbH | Inhibiteurs biarylamide de production de leukotriènes |
CA2905452A1 (fr) * | 2013-03-15 | 2014-09-25 | Bristol-Myers Squibb Company | Inhibiteurs de l'indoleamine 2,3-dioxygenase (ido) |
JP6510068B2 (ja) * | 2015-11-27 | 2019-05-08 | 大鵬薬品工業株式会社 | 新規なビフェニル化合物又はその塩 |
-
2018
- 2018-10-18 EP EP18869428.5A patent/EP3735410A4/fr not_active Withdrawn
- 2018-10-18 WO PCT/US2018/056539 patent/WO2019079614A1/fr unknown
- 2018-10-18 CA CA3092362A patent/CA3092362A1/fr not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
WO2019079614A1 (fr) | 2019-04-25 |
EP3735410A4 (fr) | 2021-11-03 |
EP3735410A1 (fr) | 2020-11-11 |
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