JP2010536882A5 - - Google Patents
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- JP2010536882A5 JP2010536882A5 JP2010522073A JP2010522073A JP2010536882A5 JP 2010536882 A5 JP2010536882 A5 JP 2010536882A5 JP 2010522073 A JP2010522073 A JP 2010522073A JP 2010522073 A JP2010522073 A JP 2010522073A JP 2010536882 A5 JP2010536882 A5 JP 2010536882A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cycloalkyl
- alkenyl
- optionally
- Prior art date
- 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.)
- Granted
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 21
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 17
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 4
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 18
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 2
- MQROWBZJYWQTKC-XILPJHNUSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(1-prop-2-ynoxypropan-2-yloxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OC(COCC#C)C)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl MQROWBZJYWQTKC-XILPJHNUSA-N 0.000 claims 1
- GEKMJNUTSMVHIA-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclobutyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CCC3)=CC=2)=C1 GEKMJNUTSMVHIA-RXFVIIJJSA-N 0.000 claims 1
- KQWVDYYPFPMBGI-ZRXLTWLYSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclohex-2-en-1-yloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3C=CCCC3)=CC=2)=C1 KQWVDYYPFPMBGI-ZRXLTWLYSA-N 0.000 claims 1
- WQHQGECQHKTVOS-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopentyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CCCC3)=CC=2)=C1 WQHQGECQHKTVOS-RTJMFUJLSA-N 0.000 claims 1
- BTCRKOKVYTVOLU-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOC3CC3)=CC=2)=C1 BTCRKOKVYTVOLU-SJSRKZJXSA-N 0.000 claims 1
- LQLLRLTVYLVSTP-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxyethyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCOC3CC3)=CC=2)=C1 LQLLRLTVYLVSTP-SJSRKZJXSA-N 0.000 claims 1
- MMFIJGNWQQHBQZ-GEMFNBEASA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-cyclopropyloxypropoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1CC1OC(C)COC(C=C1)=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MMFIJGNWQQHBQZ-GEMFNBEASA-N 0.000 claims 1
- MSMWKUYWZFAMKM-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(2-prop-2-ynoxyethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC#C)=CC=2)=C1 MSMWKUYWZFAMKM-SJSRKZJXSA-N 0.000 claims 1
- RQAIBPUKCDEEFR-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(3-cyclopropyloxypropyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCCOC3CC3)=CC=2)=C1 RQAIBPUKCDEEFR-RXFVIIJJSA-N 0.000 claims 1
- ZBTRKQLHARGRNC-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(3-cyclopropylprop-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCC#CC3CC3)=CC=2)=C1 ZBTRKQLHARGRNC-RXFVIIJJSA-N 0.000 claims 1
- CDGGMQKRHMAOOH-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(4-hydroxybut-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC#CCO)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl CDGGMQKRHMAOOH-ZQGJOIPISA-N 0.000 claims 1
- RVVVWCKTJNHSHH-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-(4-methoxybut-2-ynoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC#CCOC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl RVVVWCKTJNHSHH-SJSRKZJXSA-N 0.000 claims 1
- UBKUUUVWYGYTIJ-IZDGYUISSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[(e)-3-cyclopropylprop-2-enoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OC\C=C\C3CC3)=CC=2)=C1 UBKUUUVWYGYTIJ-IZDGYUISSA-N 0.000 claims 1
- RSKISEGUPKNIQB-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(1-methylcyclopropyl)oxyethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(CC=2C(=CC=C(C=2)[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)Cl)C=CC=1OCCOC1(C)CC1 RSKISEGUPKNIQB-SJSRKZJXSA-N 0.000 claims 1
- KAGIONOGUAKIHP-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2,2,2-trifluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC(F)(F)F)=CC=2)=C1 KAGIONOGUAKIHP-BDHVOXNPSA-N 0.000 claims 1
- UKCQFFWJYRBCDQ-IFPLKCGESA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2,2-difluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCC(F)F)=CC=2)=C1 UKCQFFWJYRBCDQ-IFPLKCGESA-N 0.000 claims 1
- VSIOFYMNPQFYQS-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-fluoroethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCCF)=CC=2)=C1 VSIOFYMNPQFYQS-ZQGJOIPISA-N 0.000 claims 1
- GNFILVCRLHZYQW-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-methoxyethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCCOCCOC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl GNFILVCRLHZYQW-SJSRKZJXSA-N 0.000 claims 1
- DGCHJACJEUHZMB-SEFGFODJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(2-pyrrolidin-1-ylethoxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCOCCN3CCCC3)=CC=2)=C1 DGCHJACJEUHZMB-SEFGFODJSA-N 0.000 claims 1
- GCYCBOWTHWGKFK-ADAARDCZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-(difluoromethoxy)ethyl]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(CCOC(F)F)=CC=2)=C1 GCYCBOWTHWGKFK-ADAARDCZSA-N 0.000 claims 1
- BTQUQFQLIUNWQM-YRLFNMAZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[2-[(3r)-oxolan-3-yl]oxyethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(OCCO[C@H]3COCC3)=CC=2)=C1 BTQUQFQLIUNWQM-YRLFNMAZSA-N 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 201000001431 Hyperuricemia Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 1
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 229940125710 antiobesity agent Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BHBZWCSWSRMTIV-GOSISDBHSA-N (3r)-3-[2-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]ethoxy]oxolane Chemical compound ClC1=CC=C(Br)C=C1CC(C=C1)=CC=C1OCCO[C@H]1COCC1 BHBZWCSWSRMTIV-GOSISDBHSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- QXAMTEJJAZOINB-UHFFFAOYSA-N oxane-3,4,5-triol Chemical compound OC1COCC(O)C1O QXAMTEJJAZOINB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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