HRP20000253A2 - Indazole bioisostere replacement of catechol in therapeutically active compounds - Google Patents

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Publication number

HRP20000253A2

HRP20000253A2 HR20000253A HRP20000253A HRP20000253A2 HR P20000253 A2 HRP20000253 A2 HR P20000253A2 HR 20000253 A HR20000253 A HR 20000253A HR P20000253 A HRP20000253 A HR P20000253A HR P20000253 A2 HRP20000253 A2 HR P20000253A2

Authority

HR

Croatia

Prior art keywords

group

alkyl

independently selected

hydrogen

image

Prior art date

1997-11-04

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• 150000001875 compounds Chemical class 0.000 title claims description 326
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims description 114
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title claims description 41
• -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 289
• 239000001257 hydrogen Substances 0.000 claims description 283
• 229910052739 hydrogen Inorganic materials 0.000 claims description 283
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 250
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 215
• 125000001424 substituent group Chemical group 0.000 claims description 179
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 166
• 230000036961 partial effect Effects 0.000 claims description 142
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
• 125000001153 fluoro group Chemical group F* 0.000 claims description 90
• 125000001246 bromo group Chemical group Br* 0.000 claims description 78
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 78
• 150000003839 salts Chemical class 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 66
• 238000006467 substitution reaction Methods 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 64
• 238000011282 treatment Methods 0.000 claims description 64
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 54
• 201000010099 disease Diseases 0.000 claims description 52
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 48
• 229910052760 oxygen Inorganic materials 0.000 claims description 47
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 229910052717 sulfur Inorganic materials 0.000 claims description 41
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 230000000694 effects Effects 0.000 claims description 40
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
• 230000001225 therapeutic effect Effects 0.000 claims description 40
• 125000004076 pyridyl group Chemical group 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 32
• 125000002883 imidazolyl group Chemical group 0.000 claims description 31
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 29
• 238000002360 preparation method Methods 0.000 claims description 29
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 28
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 27
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• 125000000335 thiazolyl group Chemical group 0.000 claims description 25
• 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 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• 125000002971 oxazolyl group Chemical group 0.000 claims description 24
• 229940127291 Calcium channel antagonist Drugs 0.000 claims description 23
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 150000001721 carbon Chemical group 0.000 claims description 21
• 239000000460 chlorine Substances 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• 125000001425 triazolyl group Chemical group 0.000 claims description 21
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
• 208000006673 asthma Diseases 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 20
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
• 239000011737 fluorine Substances 0.000 claims description 18
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 18
• 125000002757 morpholinyl group Chemical group 0.000 claims description 18
• 125000003386 piperidinyl group Chemical group 0.000 claims description 18
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 18
• 125000001544 thienyl group Chemical group 0.000 claims description 18
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 239000004480 active ingredient Substances 0.000 claims description 16
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
• 125000002837 carbocyclic group Chemical group 0.000 claims description 16
• 239000000544 cholinesterase inhibitor Substances 0.000 claims description 16
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 15
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 15
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 15
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 15
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 15
• 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000001041 indolyl group Chemical group 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 claims description 13
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 12
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 12
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 150000003254 radicals Chemical class 0.000 claims description 12
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• 208000027866 inflammatory disease Diseases 0.000 claims description 11
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 11
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 11
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 11
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 11
• 125000004306 triazinyl group Chemical group 0.000 claims description 11
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
• JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 claims description 10
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 9
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 9
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
• 239000000785 adrenergic beta-1 receptor agonist Substances 0.000 claims description 9
• 230000000118 anti-neoplastic effect Effects 0.000 claims description 9
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 8
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 8
• VXPGKSAYOBZMSX-UHFFFAOYSA-N 1,3-dioxane;1,3-dioxolane Chemical compound C1COCO1.C1COCOC1 VXPGKSAYOBZMSX-UHFFFAOYSA-N 0.000 claims description 8
• IMHJVJUMANXYCI-UHFFFAOYSA-N 1,3-dithiane;1,3-dithiolane Chemical compound C1CSCS1.C1CSCSC1 IMHJVJUMANXYCI-UHFFFAOYSA-N 0.000 claims description 8
• WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 claims description 8
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 8
• NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 8
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 8
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 8
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 8
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
• 239000000812 cholinergic antagonist Substances 0.000 claims description 8
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 8
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 8
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 8
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 8
• 241000894007 species Species 0.000 claims description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 7
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 239000003446 ligand Substances 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
• 230000001028 anti-proliverative effect Effects 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
• 229930192474 thiophene Natural products 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 108090000312 Calcium Channels Proteins 0.000 claims description 5
• 102000003922 Calcium Channels Human genes 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 4
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 4
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
• LQPOOAJESJYDLS-UHFFFAOYSA-N 1,3-oxazinane Chemical compound C1CNCOC1 LQPOOAJESJYDLS-UHFFFAOYSA-N 0.000 claims description 4
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 4
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 4
• 101100294113 Caenorhabditis elegans nhr-48 gene Proteins 0.000 claims description 4
• 101100294114 Caenorhabditis elegans nhr-49 gene Proteins 0.000 claims description 4
• 241000252506 Characiformes Species 0.000 claims description 4
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 4
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 229940097043 glucuronic acid Drugs 0.000 claims description 4
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 230000003993 interaction Effects 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• AHKJGIUKIBGOKH-UHFFFAOYSA-N morpholine;piperidine Chemical compound C1CCNCC1.C1COCCN1 AHKJGIUKIBGOKH-UHFFFAOYSA-N 0.000 claims description 4
• OZQGLZFAWYKKLQ-UHFFFAOYSA-N oxazinane Chemical compound C1CCONC1 OZQGLZFAWYKKLQ-UHFFFAOYSA-N 0.000 claims description 4
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