TWI235751B - Imidazolyl-cyclic acetals and the composition and preparation thereof - Google Patents

Info

Publication number

TWI235751B

TWI235751B TW087112466A TW87112466A TWI235751B TW I235751 B TWI235751 B TW I235751B TW 087112466 A TW087112466 A TW 087112466A TW 87112466 A TW87112466 A TW 87112466A TW I235751 B TWI235751 B TW I235751B

Authority

TW

Taiwan

Prior art keywords

compound

methyl

fluorophenyl

group

alkyl

Prior art date

1997-06-12

Links

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• 239000000203 mixture Substances 0.000 title claims description 123
• 238000002360 preparation method Methods 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 1582
• -1 azido, hydroxy Chemical group 0.000 claims abstract description 622
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 141
• 239000001257 hydrogen Substances 0.000 claims abstract description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 89
• 150000003839 salts Chemical class 0.000 claims abstract description 54
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
• 239000012453 solvate Substances 0.000 claims abstract description 22
• 150000004677 hydrates Chemical class 0.000 claims abstract description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 742
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 616
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 381
• 238000000034 method Methods 0.000 claims description 62
• 150000001412 amines Chemical class 0.000 claims description 59
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
• 150000002431 hydrogen Chemical class 0.000 claims description 45
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 39
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 239000001301 oxygen Substances 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 27
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 27
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 26
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 22
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 208000024891 symptom Diseases 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 8
• 238000006317 isomerization reaction Methods 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 229940126062 Compound A Drugs 0.000 claims description 5
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical group NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000006308 propyl amino group Chemical group 0.000 claims description 3
• OGFKTAMJLKHRAZ-UHFFFAOYSA-N 2,2-dimethoxyacetaldehyde Chemical compound COC(OC)C=O OGFKTAMJLKHRAZ-UHFFFAOYSA-N 0.000 claims description 2
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
• 239000005695 Ammonium acetate Substances 0.000 claims description 2
• 229940043376 ammonium acetate Drugs 0.000 claims description 2
• 235000019257 ammonium acetate Nutrition 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical group NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
• 150000001924 cycloalkanes Chemical class 0.000 claims 1
• 210000004268 dentin Anatomy 0.000 claims 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
• 150000002576 ketones Chemical class 0.000 claims 1
• LZHLKGAMXQASQE-UHFFFAOYSA-N o-(2,2,2-trifluoroethyl)hydroxylamine Chemical compound NOCC(F)(F)F LZHLKGAMXQASQE-UHFFFAOYSA-N 0.000 claims 1
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical class NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 claims 1
• 125000003118 aryl group Chemical group 0.000 abstract description 91
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 69
• 239000002253 acid Substances 0.000 abstract description 60
• 229940002612 prodrug Drugs 0.000 abstract description 24
• 239000000651 prodrug Substances 0.000 abstract description 24
• 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 19
• 125000002947 alkylene group Chemical group 0.000 abstract description 16
• 150000001204 N-oxides Chemical class 0.000 abstract description 14
• 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 abstract description 9
• 239000003814 drug Substances 0.000 abstract description 7
• 125000002102 aryl alkyloxo group Chemical group 0.000 abstract description 6
• 150000001721 carbon Chemical group 0.000 abstract description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 abstract description 6
• 125000004104 aryloxy group Chemical group 0.000 abstract description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
• 125000005114 heteroarylalkoxy group Chemical group 0.000 abstract description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 2
• 125000003107 substituted aryl group Chemical group 0.000 abstract description 2
• 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 abstract description 2
• 101150020251 NR13 gene Proteins 0.000 abstract 1
• 239000002451 tumor necrosis factor inhibitor Substances 0.000 abstract 1
• 238000011049 filling Methods 0.000 description 185
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
• 239000000243 solution Substances 0.000 description 58
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• 239000002585 base Substances 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 37
• 239000007787 solid Substances 0.000 description 37
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 229920005989 resin Polymers 0.000 description 29
• 239000011347 resin Substances 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 28
• 239000003480 eluent Substances 0.000 description 27
• 238000010992 reflux Methods 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
• 239000012442 inert solvent Substances 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 201000010099 disease Diseases 0.000 description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
• 230000000875 corresponding effect Effects 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 20
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
• 239000011425 bamboo Substances 0.000 description 19
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• 235000017166 Bambusa arundinacea Nutrition 0.000 description 18
• 235000017491 Bambusa tulda Nutrition 0.000 description 18
• 241001330002 Bambuseae Species 0.000 description 18
• 235000015334 Phyllostachys viridis Nutrition 0.000 description 18
• 238000002844 melting Methods 0.000 description 18
• 230000008018 melting Effects 0.000 description 18
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 17
• 125000003710 aryl alkyl group Chemical group 0.000 description 17
• 241000790917 Dioxys <bee> Species 0.000 description 16
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 16
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 238000003818 flash chromatography Methods 0.000 description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 12
• 125000002883 imidazolyl group Chemical group 0.000 description 12
• 239000000543 intermediate Substances 0.000 description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
• 229960000583 acetic acid Drugs 0.000 description 11
• 230000008030 elimination Effects 0.000 description 11
• 238000003379 elimination reaction Methods 0.000 description 11
• 229940124530 sulfonamide Drugs 0.000 description 11
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 229910021529 ammonia Inorganic materials 0.000 description 9
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 208000011580 syndromic disease Diseases 0.000 description 9
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 229920001296 polysiloxane Polymers 0.000 description 8
• 150000003254 radicals Chemical class 0.000 description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• 102000004127 Cytokines Human genes 0.000 description 7
• 108090000695 Cytokines Proteins 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 150000007857 hydrazones Chemical class 0.000 description 7
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 7
• 238000004519 manufacturing process Methods 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000005567 fluorenylene group Chemical group 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 150000004702 methyl esters Chemical class 0.000 description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 230000002441 reversible effect Effects 0.000 description 6
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• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 description 5
• 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
• 241001674048 Phthiraptera Species 0.000 description 5
• 125000004414 alkyl thio group Chemical group 0.000 description 5
• 229910052797 bismuth Inorganic materials 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• 230000029087 digestion Effects 0.000 description 5
• SNQXJPARXFUULZ-UHFFFAOYSA-N dioxolane Chemical compound C1COOC1 SNQXJPARXFUULZ-UHFFFAOYSA-N 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
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• 239000002609 medium Substances 0.000 description 5
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• 125000003367 polycyclic group Chemical group 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
• HHYMYUNAMQPTRW-UHFFFAOYSA-N 1,3-dioxolan-4-amine Chemical compound NC1COCO1 HHYMYUNAMQPTRW-UHFFFAOYSA-N 0.000 description 4
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• 206010006895 Cachexia Diseases 0.000 description 4
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• 241000725303 Human immunodeficiency virus Species 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 206010028980 Neoplasm Diseases 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 229910000831 Steel Inorganic materials 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
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