TWI527819B - 新穎三環化合物 - Google Patents

Info

Publication number

TWI527819B

TWI527819B TW103118323A TW103118323A TWI527819B TW I527819 B TWI527819 B TW I527819B TW 103118323 A TW103118323 A TW 103118323A TW 103118323 A TW103118323 A TW 103118323A TW I527819 B TWI527819 B TW I527819B

Authority

TW

Taiwan

Prior art keywords

optionally substituted

alkyl

group

cycloalkyl

substituted

Prior art date

2008-06-10

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 254
• -1 -N(R a )(R b ) Chemical class 0.000 claims description 338
• 125000000623 heterocyclic group Chemical group 0.000 claims description 160
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 111
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 108
• 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 92
• 229910052757 nitrogen Inorganic materials 0.000 claims description 92
• 229910052739 hydrogen Inorganic materials 0.000 claims description 85
• 239000001257 hydrogen Substances 0.000 claims description 85
• 125000006694 (C2-C10) heterocyclyl group Chemical group 0.000 claims description 82
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 76
• 150000002431 hydrogen Chemical class 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 59
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 58
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 57
• 229910052805 deuterium Inorganic materials 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 47
• 239000003814 drug Substances 0.000 claims description 45
• 201000010099 disease Diseases 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 34
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 34
• 125000000304 alkynyl group Chemical group 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 17
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 16
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 12
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 12
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 11
• 125000002393 azetidinyl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 150000003222 pyridines Chemical class 0.000 claims description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 9
• 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 9
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 150000003235 pyrrolidines Chemical class 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 150000003216 pyrazines Chemical class 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 150000002916 oxazoles Chemical class 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 150000004892 pyridazines Chemical class 0.000 claims description 5
• 150000003230 pyrimidines Chemical class 0.000 claims description 5
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 3
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
• 206010046851 Uveitis Diseases 0.000 claims description 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 150000002240 furans Chemical class 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 150000002460 imidazoles Chemical class 0.000 claims description 3
• 150000002545 isoxazoles Chemical class 0.000 claims description 3
• 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 3
• 150000004866 oxadiazoles Chemical class 0.000 claims description 3
• 150000002923 oximes Chemical class 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 150000003233 pyrroles Chemical class 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 230000009885 systemic effect Effects 0.000 claims description 3
• 150000003557 thiazoles Chemical class 0.000 claims description 3
• 125000004451 (C2-C10)alkenylene group Chemical group 0.000 claims description 2
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
• 208000003456 Juvenile Arthritis Diseases 0.000 claims description 2
• 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 150000005235 imidazopyrazines Chemical class 0.000 claims description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
• 150000003854 isothiazoles Chemical class 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
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• 150000004032 porphyrins Chemical group 0.000 claims description 2
• 150000005229 pyrazolopyridines Chemical class 0.000 claims description 2
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• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
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• 150000003577 thiophenes Chemical class 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims 2
• HYMXQESPSIAYCN-UHFFFAOYSA-N cyclobutanesulfonamide Chemical compound NS(=O)(=O)C1CCC1 HYMXQESPSIAYCN-UHFFFAOYSA-N 0.000 claims 2
• JKASVTAVGFSMGP-UHFFFAOYSA-N 12-(2-methylcyclohexyl)-1,5,7,10,11-pentazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaene Chemical compound CC1CCCCC1C1=NN=C2N1C(C=CN1)=C1N=C2 JKASVTAVGFSMGP-UHFFFAOYSA-N 0.000 claims 1
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
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