JP5451611B2 - １１β−ヒドロキシステロイドデヒドロゲナーゼ１のサイクリックインヒビター - Google Patents

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Publication number

JP5451611B2

JP5451611B2 JP2010518226A JP2010518226A JP5451611B2 JP 5451611 B2 JP5451611 B2 JP 5451611B2 JP 2010518226 A JP2010518226 A JP 2010518226A JP 2010518226 A JP2010518226 A JP 2010518226A JP 5451611 B2 JP5451611 B2 JP 5451611B2

Authority

JP

Japan

Prior art keywords

alkyl

halo

alkoxy

cycloalkyl

hydroxy

Prior art date

2007-07-26

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title description 9
• 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 title description 3
• 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 title 1
• 125000004122 cyclic group Chemical group 0.000 title 1
• 125000005843 halogen group Chemical group 0.000 claims description 729
• -1 CO 2 H Chemical group 0.000 claims description 597
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 240
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 236
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 216
• 125000003545 alkoxy group Chemical group 0.000 claims description 210
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 170
• 150000001875 compounds Chemical class 0.000 claims description 166
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 165
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 162
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 160
• 125000004043 oxo group Chemical group O=* 0.000 claims description 156
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 152
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 128
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 127
• 125000001072 heteroaryl group Chemical group 0.000 claims description 121
• 125000000217 alkyl group Chemical group 0.000 claims description 114
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 111
• 150000003839 salts Chemical class 0.000 claims description 107
• 239000011737 fluorine Substances 0.000 claims description 102
• 229910052731 fluorine Inorganic materials 0.000 claims description 102
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 101
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 100
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 91
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 88
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 79
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 79
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 78
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 78
• 239000000460 chlorine Substances 0.000 claims description 78
• 229910052801 chlorine Inorganic materials 0.000 claims description 78
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 73
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 70
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 69
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 68
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 68
• 150000001408 amides Chemical class 0.000 claims description 67
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 67
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 65
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 65
• 229910052794 bromium Inorganic materials 0.000 claims description 65
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 62
• 150000002367 halogens Chemical group 0.000 claims description 62
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 62
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 55
• 229910052757 nitrogen Chemical class 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 claims description 47
• 125000000623 heterocyclic group Chemical group 0.000 claims description 47
• 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 claims description 46
• 125000005148 cycloalkylalkanesulfinyl group Chemical group 0.000 claims description 41
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
• 125000004414 alkyl thio group Chemical group 0.000 claims description 39
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 37
• 125000002947 alkylene group Chemical group 0.000 claims description 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 27
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 25
• 125000001769 aryl amino group Chemical group 0.000 claims description 22
• 230000000694 effects Effects 0.000 claims description 22
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 19
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 18
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 14
• 239000001301 oxygen Substances 0.000 claims description 14
• 125000004633 N-oxo-pyridyl group Chemical group 0.000 claims description 13
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 13
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000003368 amide group Chemical class 0.000 claims description 9
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
• 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 8
• 201000010099 disease Diseases 0.000 claims description 8
• 230000014509 gene expression Effects 0.000 claims description 8
• 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• 229920002554 vinyl polymer Polymers 0.000 claims description 8
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 4
• 230000027455 binding Effects 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
• 125000003282 alkyl amino group Chemical group 0.000 claims 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
• 125000005549 heteroarylene group Chemical group 0.000 claims 1
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 83
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 82
• 125000001424 substituent group Chemical group 0.000 description 71
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 49
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 42
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 39
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 31
• 239000003862 glucocorticoid Substances 0.000 description 31
• 229910052739 hydrogen Inorganic materials 0.000 description 31
• 239000001257 hydrogen Substances 0.000 description 29
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 28
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 27
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
• 125000003226 pyrazolyl group Chemical group 0.000 description 21
• 125000001207 fluorophenyl group Chemical group 0.000 description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
• 229940037128 systemic glucocorticoids Drugs 0.000 description 18
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 17
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 17
• 125000005479 oxodihydropyridyl group Chemical group 0.000 description 17
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 16
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 15
• 229960000890 hydrocortisone Drugs 0.000 description 14
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 14
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 13
• 125000003373 pyrazinyl group Chemical group 0.000 description 13
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 150000001924 cycloalkanes Chemical class 0.000 description 12
• 150000004867 thiadiazoles Chemical group 0.000 description 12
• 238000006467 substitution reaction Methods 0.000 description 11
• LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 238000000034 method Methods 0.000 description 10
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 10
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 10
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 9
• WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
• 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 210000001519 tissue Anatomy 0.000 description 8
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 7
• OTVAEFIXJLOWRX-UHFFFAOYSA-N 2,2-dichloro-n-[1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide Chemical group CS(=O)(=O)C1=CC=C(C(O)C(CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-UHFFFAOYSA-N 0.000 description 7
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 7
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 7
• 206010020772 Hypertension Diseases 0.000 description 7
• 208000001145 Metabolic Syndrome Diseases 0.000 description 7
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 7
• 230000004410 intraocular pressure Effects 0.000 description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 7
• 108010086356 11-beta-Hydroxysteroid Dehydrogenase Type 2 Proteins 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 description 6
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
• ADBZIZGMAVRJPN-UHFFFAOYSA-N 1,2,5-thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)NCCN1 ADBZIZGMAVRJPN-UHFFFAOYSA-N 0.000 description 5
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 5
• XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 description 5
• VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 5
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 5
• OYELEBBISJGNHJ-UHFFFAOYSA-N 1,3-oxazinan-2-one Chemical compound O=C1NCCCO1 OYELEBBISJGNHJ-UHFFFAOYSA-N 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• GFPOCAYEKCWFPD-UHFFFAOYSA-N 1-(2,2,2-trifluoroethyl)piperazine Chemical compound FC(F)(F)CN1CCNCC1 GFPOCAYEKCWFPD-UHFFFAOYSA-N 0.000 description 5
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 5
• 102000006739 11-beta-Hydroxysteroid Dehydrogenase Type 2 Human genes 0.000 description 5
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 5
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 5
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
• IHXNIOYEXQWUNI-UHFFFAOYSA-N 4,5-dihydro-1h-pyrimidin-6-one Chemical compound O=C1CCN=CN1 IHXNIOYEXQWUNI-UHFFFAOYSA-N 0.000 description 5
• RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 241000277306 Esocidae Species 0.000 description 5
• 208000008589 Obesity Diseases 0.000 description 5
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 210000000988 bone and bone Anatomy 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
• 229950004696 flusalan Drugs 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 230000004060 metabolic process Effects 0.000 description 5
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 5
• 125000002757 morpholinyl group Chemical group 0.000 description 5
• 235000020824 obesity Nutrition 0.000 description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 description 5
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 5
• 229960005141 piperazine Drugs 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 description 5
• KPROUAAIOYAJTP-AVRWGWEMSA-N (6r)-3-[(1s)-1-[4-(4-fluorophenyl)phenyl]ethyl]-6-(3-hydroxypropyl)-6-thiophen-2-yl-1,3-oxazinan-2-one Chemical compound C1([C@@]2(CCCO)CCN(C(O2)=O)[C@@H](C)C=2C=CC(=CC=2)C=2C=CC(F)=CC=2)=CC=CS1 KPROUAAIOYAJTP-AVRWGWEMSA-N 0.000 description 4
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