JP2018530557A5 - - Google Patents

Info

Publication number

JP2018530557A5

JP2018530557A5 JP2018517362A JP2018517362A JP2018530557A5 JP 2018530557 A5 JP2018530557 A5 JP 2018530557A5 JP 2018517362 A JP2018517362 A JP 2018517362A JP 2018517362 A JP2018517362 A JP 2018517362A JP 2018530557 A5 JP2018530557 A5 JP 2018530557A5

Authority

JP

Japan

Prior art keywords

pyrazolo

pyridine

carboxylic acid

phenyl

cyclobutyl

Prior art date

2016-10-07

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

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• -1 C 1 -C 6 alkyl Chemical group 0.000 claims 98
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 64
• 239000002253 acid Substances 0.000 claims 54
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 51
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound 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 claims 50
• 239000005973 Carvone Substances 0.000 claims 43
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 37
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 36
• 150000003839 salts Chemical class 0.000 claims 35
• 150000001875 compounds Chemical class 0.000 claims 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 28
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 27
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 27
• UDKVMASCRFDIIP-UHFFFAOYSA-N 1,7,9,11-tetrahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CCC(C=C(C(=C3O)C(O)=O)C)=C3C1=C2 UDKVMASCRFDIIP-UHFFFAOYSA-N 0.000 claims 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 16
• 125000005466 alkylenyl group Chemical group 0.000 claims 15
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 14
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 11
• 229910052739 hydrogen Inorganic materials 0.000 claims 11
• 239000001257 hydrogen Substances 0.000 claims 11
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
• 229910052799 carbon Inorganic materials 0.000 claims 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 8
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 8
• 239000008194 pharmaceutical composition Substances 0.000 claims 8
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 8
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
• 125000000623 heterocyclic group Chemical group 0.000 claims 6
• 229910052760 oxygen Inorganic materials 0.000 claims 6
• 229910052757 nitrogen Inorganic materials 0.000 claims 5
• 125000001424 substituent group Chemical group 0.000 claims 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 3
• 201000003883 Cystic fibrosis Diseases 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 3
• 229910052736 halogen Inorganic materials 0.000 claims 3
• 150000002367 halogens Chemical class 0.000 claims 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
• 229940124597 therapeutic agent Drugs 0.000 claims 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 1
• CSCGUIQHODTEGT-UHFFFAOYSA-N 1-propan-2-ylpyrazolo[3,4-b]pyridine-6-carboxylic acid Chemical compound C1=C(C(O)=O)N=C2N(C(C)C)N=CC2=C1 CSCGUIQHODTEGT-UHFFFAOYSA-N 0.000 claims 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
• CMOMBCCGGQNCTO-UHFFFAOYSA-N BrC=1C=C(C=CC=1)N1N=C(C=2C1=NC(=CC=2C1=CC=C(C=C1)N1CCOCC1)C(=O)O)C Chemical compound BrC=1C=C(C=CC=1)N1N=C(C=2C1=NC(=CC=2C1=CC=C(C=C1)N1CCOCC1)C(=O)O)C CMOMBCCGGQNCTO-UHFFFAOYSA-N 0.000 claims 1
• LEAIZWAFVQXOOE-UHFFFAOYSA-N BrC=1C=C(C=CC=1N1CCOCC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C)C1=CC=CC=C1 Chemical compound BrC=1C=C(C=CC=1N1CCOCC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C)C1=CC=CC=C1 LEAIZWAFVQXOOE-UHFFFAOYSA-N 0.000 claims 1
• AJPSQIRZJOCBQG-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2OC(C)C)C1CCCCC1 Chemical compound C(#N)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2OC(C)C)C1CCCCC1 AJPSQIRZJOCBQG-UHFFFAOYSA-N 0.000 claims 1
• QOGDKWBMRURFLW-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C Chemical compound C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C QOGDKWBMRURFLW-UHFFFAOYSA-N 0.000 claims 1
• FSHMLFRDWNVUAD-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 Chemical compound C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 FSHMLFRDWNVUAD-UHFFFAOYSA-N 0.000 claims 1
• DBMNDOMOOYNELJ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC=CC=C1 DBMNDOMOOYNELJ-UHFFFAOYSA-N 0.000 claims 1
• DFWRRJNTGMPBNE-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=C(C=C(C=C1)F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=C(C=C(C=C1)F)F DFWRRJNTGMPBNE-UHFFFAOYSA-N 0.000 claims 1
• JAHXCYMYTPQKGN-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC(=C1)F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC(=C1)F)F JAHXCYMYTPQKGN-UHFFFAOYSA-N 0.000 claims 1
• PSJHBQQZMANFLD-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C(F)(F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C(F)(F)F PSJHBQQZMANFLD-UHFFFAOYSA-N 0.000 claims 1
• RAWUAOFVAYQLFN-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N(C)C Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N(C)C RAWUAOFVAYQLFN-UHFFFAOYSA-N 0.000 claims 1
• RBIJOTKSBXPESQ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 RBIJOTKSBXPESQ-UHFFFAOYSA-N 0.000 claims 1
• AOLMUQGWNKHNBG-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 AOLMUQGWNKHNBG-UHFFFAOYSA-N 0.000 claims 1
• VTMDLFCHXYSXIV-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCCC1 VTMDLFCHXYSXIV-UHFFFAOYSA-N 0.000 claims 1
• LUKZRLKSNOOIOG-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 LUKZRLKSNOOIOG-UHFFFAOYSA-N 0.000 claims 1
• PJORYNYPDCOPKO-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C)C1=CC=CC=C1 PJORYNYPDCOPKO-UHFFFAOYSA-N 0.000 claims 1
• HOBBPTYZFAJHAV-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1CCCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1CCCCC1 HOBBPTYZFAJHAV-UHFFFAOYSA-N 0.000 claims 1
• NGPUAPQXMLVMSY-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=C(C=C(C=C1)F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=C(C=C(C=C1)F)F NGPUAPQXMLVMSY-UHFFFAOYSA-N 0.000 claims 1
• GGXDHVGCFNXDSJ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=C(C=C1)F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=C(C=C1)F)F GGXDHVGCFNXDSJ-UHFFFAOYSA-N 0.000 claims 1
• CJDMNZZCZVFQBZ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C CJDMNZZCZVFQBZ-UHFFFAOYSA-N 0.000 claims 1
• XTFANUHRFOYEHK-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C(F)(F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)C(F)(F)F XTFANUHRFOYEHK-UHFFFAOYSA-N 0.000 claims 1
• YSBPPEATGIYQAH-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)F YSBPPEATGIYQAH-UHFFFAOYSA-N 0.000 claims 1
• NBPGYTZEFZRJSA-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 NBPGYTZEFZRJSA-UHFFFAOYSA-N 0.000 claims 1
• XBTGLHYTLMQEMG-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 XBTGLHYTLMQEMG-UHFFFAOYSA-N 0.000 claims 1
• URXMAPJPAJEMSR-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCCC1 URXMAPJPAJEMSR-UHFFFAOYSA-N 0.000 claims 1
• WXZJBIGBPAVJAY-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCOCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=NC=C1)N1CCOCC1 WXZJBIGBPAVJAY-UHFFFAOYSA-N 0.000 claims 1
• MTIKDZCDZKVHFF-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1CCCCC1 MTIKDZCDZKVHFF-UHFFFAOYSA-N 0.000 claims 1
• SVQUEUXMQFJSAW-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CC(C1)(C)C)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CC(C1)(C)C)C1=CC=CC=C1 SVQUEUXMQFJSAW-UHFFFAOYSA-N 0.000 claims 1
• DCPKVSGWZPNTEJ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CC(C1)(F)F)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CC(C1)(F)F)C1=CC=CC=C1 DCPKVSGWZPNTEJ-UHFFFAOYSA-N 0.000 claims 1
• LUSMCSBSHWQQQJ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=CC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=CC=C1)N1CCCC1 LUSMCSBSHWQQQJ-UHFFFAOYSA-N 0.000 claims 1
• DAUFDPMCHRXTKJ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=NC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=NC=C1)N1CCCC1 DAUFDPMCHRXTKJ-UHFFFAOYSA-N 0.000 claims 1
• JQRSXKCADUJFQY-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=NC=C1)N1CCOCC1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C1CCC1)C1=CC(=NC=C1)N1CCOCC1 JQRSXKCADUJFQY-UHFFFAOYSA-N 0.000 claims 1
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• IAQUEIAXLRDJMX-BGYRXZFFSA-N C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2[C@@H]1C[C@@H](C1)F)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2[C@@H]1C[C@@H](C1)F)C1=CC=CC=C1 IAQUEIAXLRDJMX-BGYRXZFFSA-N 0.000 claims 1
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• KFTHWPPQVVSZCG-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=NC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 Chemical compound C(#N)C1CCN(CC1)C1=NC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCCC1 KFTHWPPQVVSZCG-UHFFFAOYSA-N 0.000 claims 1
• KKKAEPVZDQRTOE-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=NC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 Chemical compound C(#N)C1CCN(CC1)C1=NC=C(C=N1)C1=C2C(=NC(=C1)C(=O)O)N(N=C2C(C)C)C1=CC(=CC=C1)N1CCOCC1 KKKAEPVZDQRTOE-UHFFFAOYSA-N 0.000 claims 1
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• WHYUAGZAHLUISP-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]-3,6-dihydro-2h-pyridin-4-yl]boronic acid Chemical group CC(C)(C)OC(=O)N1CCC(B(O)O)=CC1 WHYUAGZAHLUISP-UHFFFAOYSA-N 0.000 claims 1
• 230000001548 androgenic effect Effects 0.000 claims 1
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
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• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
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• 239000003607 modifier Substances 0.000 claims 1
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