JP2021506858A5 - - Google Patents

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Publication number

JP2021506858A5

JP2021506858A5 JP2020533676A JP2020533676A JP2021506858A5 JP 2021506858 A5 JP2021506858 A5 JP 2021506858A5 JP 2020533676 A JP2020533676 A JP 2020533676A JP 2020533676 A JP2020533676 A JP 2020533676A JP 2021506858 A5 JP2021506858 A5 JP 2021506858A5

Authority

JP

Japan

Prior art keywords

pyridin

pyrrolo

triazolo

pyridine

dimethyl

Prior art date

2018-12-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

• Espacenet
• Global Dossier
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• -1 heptanyl Chemical group 0.000 claims 704
• 125000000217 alkyl group Chemical group 0.000 claims 110
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 81
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 80
• 125000003386 piperidinyl group Chemical group 0.000 claims 71
• 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 62
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 56
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 50
• 125000002757 morpholinyl group Chemical group 0.000 claims 48
• 125000004076 pyridyl group Chemical group 0.000 claims 41
• 125000003709 fluoroalkyl group Chemical group 0.000 claims 40
• 125000004193 piperazinyl group Chemical group 0.000 claims 40
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 38
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 35
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 32
• 125000002393 azetidinyl group Chemical group 0.000 claims 32
• 125000000168 pyrrolyl group Chemical group 0.000 claims 31
• 125000001424 substituent group Chemical group 0.000 claims 29
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 28
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 25
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 23
• 125000003566 oxetanyl group Chemical group 0.000 claims 23
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 23
• 229910052799 carbon Inorganic materials 0.000 claims 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 20
• 125000004966 cyanoalkyl group Chemical group 0.000 claims 19
• 125000005959 diazepanyl group Chemical group 0.000 claims 19
• 125000000623 heterocyclic group Chemical group 0.000 claims 19
• 229910052757 nitrogen Inorganic materials 0.000 claims 18
• 125000001425 triazolyl group Chemical group 0.000 claims 18
• 125000003545 alkoxy group Chemical group 0.000 claims 16
• 150000001875 compounds Chemical class 0.000 claims 16
• 150000003839 salts Chemical class 0.000 claims 16
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 14
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
• 125000004103 aminoalkyl group Chemical group 0.000 claims 12
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 12
• 125000002883 imidazolyl group Chemical group 0.000 claims 12
• 125000003373 pyrazinyl group Chemical group 0.000 claims 11
• 125000004432 carbon atom Chemical group C* 0.000 claims 10
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
• OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 claims 9
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
• KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
• 125000001544 thienyl group Chemical group 0.000 claims 8
• 125000003944 tolyl group Chemical group 0.000 claims 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 7
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 7
• 125000003725 azepanyl group Chemical group 0.000 claims 7
• 125000000335 thiazolyl group Chemical group 0.000 claims 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims 6
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 6
• CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 claims 5
• 125000002971 oxazolyl group Chemical group 0.000 claims 5
• IKHGUXGNUITLKF-QDNHWIQGSA-N 1,2-dideuterioethanone Chemical compound [2H]CC([2H])=O IKHGUXGNUITLKF-QDNHWIQGSA-N 0.000 claims 4
• CNWPASBXBJMZDN-UHFFFAOYSA-N C(C)(C)(C)NC1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C Chemical compound C(C)(C)(C)NC1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C CNWPASBXBJMZDN-UHFFFAOYSA-N 0.000 claims 4
• UTLNCOZJLSUKLW-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(COC2)C1)C1=CN(C2=NC=CC=C21)C Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(COC2)C1)C1=CN(C2=NC=CC=C21)C UTLNCOZJLSUKLW-UHFFFAOYSA-N 0.000 claims 4
• KXKVQMMIBOHSFK-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(COC2)C1)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(COC2)C1)C=1C=C(C=2N(C=1)N=CN=2)OC KXKVQMMIBOHSFK-UHFFFAOYSA-N 0.000 claims 4
• MVQXGQCGLFEQFO-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(CS(C2)(=O)=O)C1)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CC2(CS(C2)(=O)=O)C1)C=1C=C(C=2N(C=1)N=CN=2)OC MVQXGQCGLFEQFO-UHFFFAOYSA-N 0.000 claims 4
• MPMLWXXZDQGDAZ-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CCOCC1)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CCOCC1)C=1C=C(C=2N(C=1)N=CN=2)OC MPMLWXXZDQGDAZ-UHFFFAOYSA-N 0.000 claims 4
• UUNSBEYOEIRBHS-UHFFFAOYSA-N C(C)N(C1CCC(CC1)C1=C(C=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C)C Chemical compound C(C)N(C1CCC(CC1)C1=C(C=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C)C UUNSBEYOEIRBHS-UHFFFAOYSA-N 0.000 claims 4
• XKYRZYODHIYCGT-UHFFFAOYSA-N C(C)N1C=C(C=2C1=NC=CC=2)C1=C(C2=NC(=CC=C2N1)C1CCC(CC1)NC1CCOCC1)C(C)C Chemical compound C(C)N1C=C(C=2C1=NC=CC=2)C1=C(C2=NC(=CC=C2N1)C1CCC(CC1)NC1CCOCC1)C(C)C XKYRZYODHIYCGT-UHFFFAOYSA-N 0.000 claims 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
• ZTTBXKASLZCXGK-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(C1COC1)CC)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(C1COC1)CC)C(C)C)N=CN=2)C ZTTBXKASLZCXGK-UHFFFAOYSA-N 0.000 claims 4
• UWTHGKUPGWGTHX-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CCC#N)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CCC#N)C)C(C)C)N=CN=2)C UWTHGKUPGWGTHX-UHFFFAOYSA-N 0.000 claims 4
• CXPNJFQHRUEUQN-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(C)C)C(C)C)N=CN=2)C CXPNJFQHRUEUQN-UHFFFAOYSA-N 0.000 claims 4
• SKZSGEWYZRDIAG-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(O)C)C(C)C)N=CN=2)C SKZSGEWYZRDIAG-UHFFFAOYSA-N 0.000 claims 4
• HTFYATCZSCMLGG-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)C(=O)N(C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)C(=O)N(C)C)C(C)C)N=CN=2)C HTFYATCZSCMLGG-UHFFFAOYSA-N 0.000 claims 4
• NZYDEZBAGMNAGF-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)OC)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)OC)C(C)C)N=CN=2)C NZYDEZBAGMNAGF-UHFFFAOYSA-N 0.000 claims 4
• YXNTWYWGKJPMHA-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(CC1)F)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(CC1)F)C(C)C)N=CN=2)C YXNTWYWGKJPMHA-UHFFFAOYSA-N 0.000 claims 4
• HSWFDNXIUMOTQR-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(C1)COCC3)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(C1)COCC3)C(C)C)N=CN=2)C HSWFDNXIUMOTQR-UHFFFAOYSA-N 0.000 claims 4
• JEYGXARWKLFVJN-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCO3)C1)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCO3)C1)C(C)C)N=CN=2)C JEYGXARWKLFVJN-UHFFFAOYSA-N 0.000 claims 4
• VAXMGBQEINEHNI-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCOC3)CC1)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCOC3)CC1)C(C)C)N=CN=2)C VAXMGBQEINEHNI-UHFFFAOYSA-N 0.000 claims 4
• GCRWVTKYWLNIAB-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(COC3)CC1)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(COC3)CC1)C(C)C)N=CN=2)C GCRWVTKYWLNIAB-UHFFFAOYSA-N 0.000 claims 4
• HODZQOPSHRDZFY-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)NCC1(CC1)S(=O)(=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)NCC1(CC1)S(=O)(=O)C)C(C)C)N=CN=2)C HODZQOPSHRDZFY-UHFFFAOYSA-N 0.000 claims 4
• MLXDFJWMKJXEHU-UHFFFAOYSA-N COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(C1)COCC3)C(C)C)N=CN=2 Chemical compound COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(C1)COCC3)C(C)C)N=CN=2 MLXDFJWMKJXEHU-UHFFFAOYSA-N 0.000 claims 4
• GXIMXXPTHWZXNL-UHFFFAOYSA-N COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCO3)C1)C(C)C)N=CN=2 Chemical compound COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(CCO3)C1)C(C)C)N=CN=2 GXIMXXPTHWZXNL-UHFFFAOYSA-N 0.000 claims 4
• OMPQKGABYZONEF-UHFFFAOYSA-N COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(COC3)CC1)C(C)C)N=CN=2 Chemical compound COC=1C=2N(C=C(C=1)C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC3(COC3)CC1)C(C)C)N=CN=2 OMPQKGABYZONEF-UHFFFAOYSA-N 0.000 claims 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
• 150000001204 N-oxides Chemical class 0.000 claims 4
• ZKGABBKKSOUUIH-UHFFFAOYSA-N N1(CCC1)C1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C Chemical compound N1(CCC1)C1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C ZKGABBKKSOUUIH-UHFFFAOYSA-N 0.000 claims 4
• 125000003118 aryl group Chemical group 0.000 claims 4
• FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical compound NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 claims 4
• GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims 4
• 229910052736 halogen Inorganic materials 0.000 claims 4
• 150000002367 halogens Chemical class 0.000 claims 4
• 125000006393 methylpyrimidinyl group Chemical group 0.000 claims 4
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 4
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
• BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
• AAFUNFZRUWOWNY-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CC(CC1)NCC(=O)NC)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CC(CC1)NCC(=O)NC)C=1C=C(C=2N(C=1)N=CN=2)OC AAFUNFZRUWOWNY-UHFFFAOYSA-N 0.000 claims 3
• JDGZEKNWRDRRRG-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CCCC1)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)N1CCCC1)C=1C=C(C=2N(C=1)N=CN=2)OC JDGZEKNWRDRRRG-UHFFFAOYSA-N 0.000 claims 3
• RCFXDLXTECFJHV-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)NC1COC1)C=1C=C(C=2N(C=1)N=CN=2)CO Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)NC1COC1)C=1C=C(C=2N(C=1)N=CN=2)CO RCFXDLXTECFJHV-UHFFFAOYSA-N 0.000 claims 3
• XUXIPXPARZBNQW-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)N1CCN(CC1)C(C)C)C1=CN(C=2N=CN=CC=21)C Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)N1CCN(CC1)C(C)C)C1=CN(C=2N=CN=CC=21)C XUXIPXPARZBNQW-UHFFFAOYSA-N 0.000 claims 3
• RBZWTCIHAKJEDZ-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)N(C)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)N(C)C)C)C(C)C)N=CN=2)C RBZWTCIHAKJEDZ-UHFFFAOYSA-N 0.000 claims 3
• PRHSKISKOQNTCM-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)NC)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)NC)C)C(C)C)N=CN=2)C PRHSKISKOQNTCM-UHFFFAOYSA-N 0.000 claims 3
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• FLMMENONIJMVIF-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC(C1)(C)C)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC(C1)(C)C)=O)C(C)C)N=CN=2)C FLMMENONIJMVIF-UHFFFAOYSA-N 0.000 claims 2
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• NJYVMQFBEWDLCR-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC(CC1)(C)O)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC(CC1)(C)O)=O)C(C)C)N=CN=2)C NJYVMQFBEWDLCR-UHFFFAOYSA-N 0.000 claims 2
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• MRHDFGMXTZBSGM-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC3(COC3)CC1)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CC3(COC3)CC1)=O)C(C)C)N=CN=2)C MRHDFGMXTZBSGM-UHFFFAOYSA-N 0.000 claims 2
• NMRUWWRASDZXJO-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CCC(CC1)CO)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CCC(CC1)CO)=O)C(C)C)N=CN=2)C NMRUWWRASDZXJO-UHFFFAOYSA-N 0.000 claims 2
• JRDURUFMDWZWEY-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CCCC1)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CN1CCCC1)=O)C(C)C)N=CN=2)C JRDURUFMDWZWEY-UHFFFAOYSA-N 0.000 claims 2
• KFTJJUGLFGSOQF-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CNC)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CNC)=O)C(C)C)N=CN=2)C KFTJJUGLFGSOQF-UHFFFAOYSA-N 0.000 claims 2
• XHTMUAVHYYKQCK-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CNCC)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)C(CNCC)=O)C(C)C)N=CN=2)C XHTMUAVHYYKQCK-UHFFFAOYSA-N 0.000 claims 2
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• ONXKQCPWUORHGA-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)CCC#N)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)CCC#N)C(C)C)N=CN=2)C ONXKQCPWUORHGA-UHFFFAOYSA-N 0.000 claims 2
• GNGOXSNMUWYNIG-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)S(=O)(=O)CCN(C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1CCN(CC1)S(=O)(=O)CCN(C)C)C(C)C)N=CN=2)C GNGOXSNMUWYNIG-UHFFFAOYSA-N 0.000 claims 2
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• RFZIHYGAFKLZSY-KRWDZBQOSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(C)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(C)C)C)C(C)C)N=CN=2)C RFZIHYGAFKLZSY-KRWDZBQOSA-N 0.000 claims 2
• ZQIVFCVBUIELHN-SFHVURJKSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(CCN(C)C)=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(CCN(C)C)=O)C)C(C)C)N=CN=2)C ZQIVFCVBUIELHN-SFHVURJKSA-N 0.000 claims 2
• MIFMGWLDIIZDRG-KRWDZBQOSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(CN(C)C)=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](N(CC1)C(CN(C)C)=O)C)C(C)C)N=CN=2)C MIFMGWLDIIZDRG-KRWDZBQOSA-N 0.000 claims 2
• OZLIPVLAHSIBTM-AWEZNQCLSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](NCC1)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H](NCC1)C)C(C)C)N=CN=2)C OZLIPVLAHSIBTM-AWEZNQCLSA-N 0.000 claims 2
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• UCERYYQPOUPKCE-KDURUIRLSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H]3N([C@H](C1)C3)C(C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@@H]3N([C@H](C1)C3)C(C)C)C(C)C)N=CN=2)C UCERYYQPOUPKCE-KDURUIRLSA-N 0.000 claims 2
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• QFMRVOVRVVVMAJ-LJQANCHMSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(CC1)C(CN1CCCC1)=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(CC1)C(CN1CCCC1)=O)C)C(C)C)N=CN=2)C QFMRVOVRVVVMAJ-LJQANCHMSA-N 0.000 claims 2
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• ZPHPNGHQYGLATH-KDURUIRLSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N([C@H](C1)C)CCCS(=O)(=O)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N([C@H](C1)C)CCCS(=O)(=O)C)C)C(C)C)N=CN=2)C ZPHPNGHQYGLATH-KDURUIRLSA-N 0.000 claims 2
• OZLIPVLAHSIBTM-CQSZACIVSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)C)C(C)C)N=CN=2)C OZLIPVLAHSIBTM-CQSZACIVSA-N 0.000 claims 2
• XFOUAKVFHFXIBY-INIZCTEOSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)CO)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)CO)C(C)C)N=CN=2)C XFOUAKVFHFXIBY-INIZCTEOSA-N 0.000 claims 2
• MZGZSWPZZLAHTH-HUUCEWRRSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N[C@@H](C1)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N[C@@H](C1)C)C)C(C)C)N=CN=2)C MZGZSWPZZLAHTH-HUUCEWRRSA-N 0.000 claims 2
• MZGZSWPZZLAHTH-GASCZTMLSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N[C@H](C1)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N[C@H](C1)C)C)C(C)C)N=CN=2)C MZGZSWPZZLAHTH-GASCZTMLSA-N 0.000 claims 2
• BEZFYFSBXXFOLC-HDICACEKSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H]3CCC[C@@H](C1)N3)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H]3CCC[C@@H](C1)N3)C(C)C)N=CN=2)C BEZFYFSBXXFOLC-HDICACEKSA-N 0.000 claims 2
• FMMZRUPGRWODOP-OYRHEFFESA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H]3CCC[C@@H](C1)N3CCS(=O)(=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H]3CCC[C@@H](C1)N3CCS(=O)(=O)C)C(C)C)N=CN=2)C FMMZRUPGRWODOP-OYRHEFFESA-N 0.000 claims 2
• HNAIGODTMOKNNK-QGZVFWFLSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(CC1)C(C)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(CC1)C(C)C)C)C(C)C)N=CN=2)C HNAIGODTMOKNNK-QGZVFWFLSA-N 0.000 claims 2
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• DOTFCINXJRZRAI-UHFFFAOYSA-N FC=1C=C2C(=NC=1C1CCNCC1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C Chemical compound FC=1C=C2C(=NC=1C1CCNCC1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C DOTFCINXJRZRAI-UHFFFAOYSA-N 0.000 claims 2
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
• IMWBVEAQJRAXRE-UHFFFAOYSA-N N1(CCC1)C1CCC(CC1)C1=C(C=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C Chemical compound N1(CCC1)C1CCC(CC1)C1=C(C=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C IMWBVEAQJRAXRE-UHFFFAOYSA-N 0.000 claims 2
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• PBIUUJCEMUAWJJ-UHFFFAOYSA-N azetidine-3-carbonitrile Chemical compound N#CC1CNC1 PBIUUJCEMUAWJJ-UHFFFAOYSA-N 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 0 C*c1cc(cccc2)c2[o]1 Chemical compound C*c1cc(cccc2)c2[o]1 0.000 description 2
• QUOUHOVGOUVQBE-MEMLXQNLSA-N CC(C)c1c(-c2c[n]3ncnc3c(C)c2C)[nH]c2c1nc([C@H](CC1)CC[C@@H]1N(CC1)CCS1(=O)=O)cc2 Chemical compound CC(C)c1c(-c2c[n]3ncnc3c(C)c2C)[nH]c2c1nc([C@H](CC1)CC[C@@H]1N(CC1)CCS1(=O)=O)cc2 QUOUHOVGOUVQBE-MEMLXQNLSA-N 0.000 description 1