TW200934495A - Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 - Google Patents

Info

Publication number

TW200934495A

TW200934495A TW097143034A TW97143034A TW200934495A TW 200934495 A TW200934495 A TW 200934495A TW 097143034 A TW097143034 A TW 097143034A TW 97143034 A TW97143034 A TW 97143034A TW 200934495 A TW200934495 A TW 200934495A

Authority

TW

Taiwan

Prior art keywords

group

cvc6

alkyl

alkoxy

halo

Prior art date

2007-11-07

Links

• Espacenet
• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 11
• 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 title description 3
• 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 title 1
• ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 216
• 238000000034 method Methods 0.000 claims abstract description 82
• 150000003839 salts Chemical class 0.000 claims abstract description 63
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
• 201000010099 disease Diseases 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 695
• 125000003545 alkoxy group Chemical group 0.000 claims description 542
• 125000005843 halogen group Chemical group 0.000 claims description 528
• -1 CH2CH2 oxime Chemical class 0.000 claims description 414
• 125000003282 alkyl amino group Chemical group 0.000 claims description 211
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 168
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 145
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 124
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 118
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 104
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 93
• 125000001072 heteroaryl group Chemical group 0.000 claims description 93
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 92
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 88
• 150000001412 amines Chemical class 0.000 claims description 77
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 75
• 125000004414 alkyl thio group Chemical group 0.000 claims description 74
• 239000007789 gas Chemical group 0.000 claims description 67
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 66
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 64
• 229910052736 halogen Inorganic materials 0.000 claims description 63
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 61
• 150000002367 halogens Chemical class 0.000 claims description 61
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 60
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 59
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 59
• 239000011737 fluorine Substances 0.000 claims description 59
• 229910052731 fluorine Inorganic materials 0.000 claims description 59
• 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 57
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 54
• 125000000623 heterocyclic group Chemical group 0.000 claims description 53
• 125000003342 alkenyl group Chemical group 0.000 claims description 52
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 51
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 50
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 49
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 49
• 102220498322 HLA class II histocompatibility antigen, DR beta 3 chain_R40S_mutation Human genes 0.000 claims description 45
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 44
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 40
• 102200077464 rs398122966 Human genes 0.000 claims description 40
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 38
• 125000000304 alkynyl group Chemical group 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 30
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 29
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 29
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
• 125000001153 fluoro group Chemical group F* 0.000 claims description 28
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 25
• 125000003277 amino group Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 150000003973 alkyl amines Chemical class 0.000 claims description 21
• 150000002576 ketones Chemical class 0.000 claims description 21
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 19
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 19
• 150000001924 cycloalkanes Chemical class 0.000 claims description 18
• 230000000694 effects Effects 0.000 claims description 18
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 18
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 125000005427 anthranyl group Chemical group 0.000 claims description 15
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 13
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003107 substituted aryl group Chemical group 0.000 claims description 11
• 101100451537 Caenorhabditis elegans hsd-1 gene Proteins 0.000 claims description 10
• 239000000460 chlorine Chemical group 0.000 claims description 10
• 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 10
• 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
• 125000000524 functional group Chemical group 0.000 claims description 9
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 239000011734 sodium Substances 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• 125000001769 aryl amino group Chemical group 0.000 claims description 8
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
• 150000002923 oximes Chemical class 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 238000012360 testing method Methods 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• 101150010802 CVC2 gene Proteins 0.000 claims description 6
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
• 125000006612 decyloxy group Chemical group 0.000 claims description 6
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 239000005864 Sulphur Substances 0.000 claims description 4
• 125000005264 aryl amine group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 3
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
• 229910003600 H2NS Inorganic materials 0.000 claims description 3
• 150000004982 aromatic amines Chemical class 0.000 claims description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
• CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
• 150000001345 alkine derivatives Chemical class 0.000 claims description 2
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
• 150000001356 alkyl thiols Chemical class 0.000 claims description 2
• 150000001413 amino acids Chemical class 0.000 claims description 2
• 238000001354 calcination Methods 0.000 claims description 2
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 2
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 239000011733 molybdenum Substances 0.000 claims description 2
• 229910052750 molybdenum Inorganic materials 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 239000002689 soil Substances 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
• 239000004202 carbamide Substances 0.000 claims 2
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 2
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 2
• 125000002757 morpholinyl group Chemical group 0.000 claims 2
• 125000003386 piperidinyl group Chemical group 0.000 claims 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
• 125000000335 thiazolyl group Chemical group 0.000 claims 2
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
• RDXLZJXIVYZKNT-UHFFFAOYSA-N 1-(1-cyclohexylethyl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)-1,3-diazinan-2-one Chemical compound C1CC(CCCO)(C=2C=CC(F)=CC=2)NC(=O)N1C(C)C1CCCCC1 RDXLZJXIVYZKNT-UHFFFAOYSA-N 0.000 claims 1
• YUJAXGHCMAHYOR-UHFFFAOYSA-N 1-[1-(4-bromophenyl)ethyl]-4-(4-fluorophenyl)-4-(3-hydroxypropyl)-3-methyl-1,3-diazinan-2-one Chemical compound C=1C=C(Br)C=CC=1C(C)N(C(N1C)=O)CCC1(CCCO)C1=CC=C(F)C=C1 YUJAXGHCMAHYOR-UHFFFAOYSA-N 0.000 claims 1
• HHDVTFNGTOKZQI-UHFFFAOYSA-N 1-[1-[4-(2,4-difluorophenyl)phenyl]ethyl]-4-(4-fluorophenyl)-4-(3-hydroxypropyl)-1,3-diazinan-2-one Chemical compound C=1C=C(C=2C(=CC(F)=CC=2)F)C=CC=1C(C)N(C(N1)=O)CCC1(CCCO)C1=CC=C(F)C=C1 HHDVTFNGTOKZQI-UHFFFAOYSA-N 0.000 claims 1
• BWCWPIIVYWOSFR-UHFFFAOYSA-N 1-[1-[4-(4-fluorophenyl)phenyl]ethyl]-4-(3-hydroxypropyl)-4-phenyl-1,3-diazinan-2-one Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(C)N(C(N1)=O)CCC1(CCCO)C1=CC=CC=C1 BWCWPIIVYWOSFR-UHFFFAOYSA-N 0.000 claims 1
• ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
• LFBLXBZNMMITTO-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-(2-hydroxyethyl)-1-[1-(4-methoxyphenyl)ethyl]-1,3-diazinan-2-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)NC(CCO)(C=2C=CC(F)=CC=2)CC1 LFBLXBZNMMITTO-UHFFFAOYSA-N 0.000 claims 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical group CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
• 241000266847 Mephitidae Species 0.000 claims 1
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims 1
• 229920002675 Polyoxyl Polymers 0.000 claims 1
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