JP2003520268A5 - - Google Patents

Info

Publication number

JP2003520268A5

JP2003520268A5 JP2001553262A JP2001553262A JP2003520268A5 JP 2003520268 A5 JP2003520268 A5 JP 2003520268A5 JP 2001553262 A JP2001553262 A JP 2001553262A JP 2001553262 A JP2001553262 A JP 2001553262A JP 2003520268 A5 JP2003520268 A5 JP 2003520268A5

Authority

JP

Japan

Prior art keywords

phenyl

acid

ethoxy

substituted

pharmaceutically acceptable

Prior art date

2001-01-17

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

Links

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• 150000001875 compounds Chemical class 0.000 description 125
• -1 hydroxy, thio, amino Chemical group 0.000 description 120
• 150000003839 salts Chemical class 0.000 description 95
• 125000000217 alkyl group Chemical group 0.000 description 53
• 239000000203 mixture Substances 0.000 description 38
• 125000003118 aryl group Chemical group 0.000 description 37
• 238000006243 chemical reaction Methods 0.000 description 32
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 125000003710 aryl alkyl group Chemical group 0.000 description 30
• 125000001072 heteroaryl group Chemical group 0.000 description 29
• 125000003545 alkoxy group Chemical group 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 238000000034 method Methods 0.000 description 26
• 125000000623 heterocyclic group Chemical group 0.000 description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 22
• 125000004475 heteroaralkyl group Chemical group 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 125000002252 acyl group Chemical group 0.000 description 21
• 229910052739 hydrogen Inorganic materials 0.000 description 20
• 239000001257 hydrogen Substances 0.000 description 20
• 229910052760 oxygen Inorganic materials 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 125000000753 cycloalkyl group Chemical group 0.000 description 17
• 229910052736 halogen Inorganic materials 0.000 description 17
• 150000002367 halogens Chemical class 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
• 229910052717 sulfur Inorganic materials 0.000 description 16
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
• 239000012453 solvate Substances 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 150000002431 hydrogen Chemical class 0.000 description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 13
• IPAUKBFVTRGOJW-UHFFFAOYSA-N 3-[4-[2-(2,5-dimethylpyrrol-1-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C)=CC=C1C IPAUKBFVTRGOJW-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 125000004442 acylamino group Chemical group 0.000 description 12
• 201000010099 disease Diseases 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 208000008589 Obesity Diseases 0.000 description 11
• 125000004423 acyloxy group Chemical group 0.000 description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• 235000020824 obesity Nutrition 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 125000004414 alkyl thio group Chemical group 0.000 description 10
• 239000012298 atmosphere Substances 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 201000001320 Atherosclerosis Diseases 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000004103 aminoalkyl group Chemical group 0.000 description 9
• 125000001769 aryl amino group Chemical group 0.000 description 9
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 9
• 125000004104 aryloxy group Chemical group 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 206010012601 diabetes mellitus Diseases 0.000 description 9
• 125000005843 halogen group Chemical group 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 150000003009 phosphonic acids Chemical class 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• 125000005160 aryl oxy alkyl group Chemical group 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• 235000012000 cholesterol Nutrition 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 206010022489 Insulin Resistance Diseases 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
• 108010016731 PPAR gamma Proteins 0.000 description 7
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 7
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
• 229910052799 carbon Inorganic materials 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 235000019260 propionic acid Nutrition 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 150000003626 triacylglycerols Chemical class 0.000 description 7
• IYDWZEAUTWAAOU-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-methyl-5-propan-2-ylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(C)C)=CC=C1C IYDWZEAUTWAAOU-UHFFFAOYSA-N 0.000 description 6
• NTQFKQRYDOJPPG-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-3-phenyl-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=C(C=2C=CC=CC=2)C=C1C(C)C NTQFKQRYDOJPPG-UHFFFAOYSA-N 0.000 description 6
• GPARKEJZVNFADP-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-5-phenylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=CC=C1C1=CC=CC=C1 GPARKEJZVNFADP-UHFFFAOYSA-N 0.000 description 6
• XIXQFXWGHVLSIQ-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=CC=C1C(C)C XIXQFXWGHVLSIQ-UHFFFAOYSA-N 0.000 description 6
• QWNQOLMKARXDEB-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-methoxyphenyl)-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(OC)=CC=2)=CC=C1C(C)C QWNQOLMKARXDEB-UHFFFAOYSA-N 0.000 description 6
• OCXWRPVOLYNDJZ-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[3-phenyl-2,5-di(propan-2-yl)pyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(C)C)=C(C=2C=CC=CC=2)C=C1C(C)C OCXWRPVOLYNDJZ-UHFFFAOYSA-N 0.000 description 6
• IQTYBOQGSBZJIM-UHFFFAOYSA-N 2-ethoxy-3-[4-[3-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]propoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCCN1C(C=2C=CC(F)=CC=2)=C(C=2C=CC=CC=2)C(C(=O)NC=2C=CC=CC=2)=C1C(C)C IQTYBOQGSBZJIM-UHFFFAOYSA-N 0.000 description 6
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
• 0 Cc(c(*)c1*)c(*)c(*2)c1N(*)C1C2CCCCC1 Chemical compound Cc(c(*)c1*)c(*)c(*2)c1N(*)C1C2CCCCC1 0.000 description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 108010007622 LDL Lipoproteins Proteins 0.000 description 6
• 102000007330 LDL Lipoproteins Human genes 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
• 125000003282 alkyl amino group Chemical group 0.000 description 6
• 125000006598 aminocarbonylamino group Chemical group 0.000 description 6
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 6
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 6
• 239000008280 blood Substances 0.000 description 6
• 210000004369 blood Anatomy 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 description 6
• 125000004663 dialkyl amino group Chemical group 0.000 description 6
• JNWNQEQSQTVAND-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-3-phenyl-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=C(C=2C=CC=CC=2)C=C1C(C)C JNWNQEQSQTVAND-UHFFFAOYSA-N 0.000 description 6
• KKWZECKFOFFAFQ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-5-phenylpyrrol-1-yl]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=CC=C1C1=CC=CC=C1 KKWZECKFOFFAFQ-UHFFFAOYSA-N 0.000 description 6
• INOQUFYQZQZWQS-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=CC=C1C(C)C INOQUFYQZQZWQS-UHFFFAOYSA-N 0.000 description 6
• WXMKLGDJXQWHMA-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[2-(4-methoxyphenyl)-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN1C(C=2C=CC(OC)=CC=2)=CC=C1C(C)C WXMKLGDJXQWHMA-UHFFFAOYSA-N 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 125000002541 furyl group Chemical group 0.000 description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
• 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 150000003460 sulfonic acids Chemical class 0.000 description 6
• 125000001544 thienyl group Chemical group 0.000 description 6
• QNPAFNGIIMDYHU-UHFFFAOYSA-N 2-ethoxy-3-[4-(2-pyrrol-1-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C=CC=C1 QNPAFNGIIMDYHU-UHFFFAOYSA-N 0.000 description 5
• WIHJPIMCOWMXAB-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=C(C=2C=CC=CC=2)C(C(=O)NC=2C=CC=CC=2)=C1C(C)C WIHJPIMCOWMXAB-UHFFFAOYSA-N 0.000 description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
• ASZLFHBBCRLSNI-UHFFFAOYSA-N CCOC(Cc1ccc(OCCn2c(cc(C(=O)OCC)c2-c2ccccc2)-c2ccc(F)cc2)cc1)C(O)=O Chemical compound CCOC(Cc1ccc(OCCn2c(cc(C(=O)OCC)c2-c2ccccc2)-c2ccc(F)cc2)cc1)C(O)=O ASZLFHBBCRLSNI-UHFFFAOYSA-N 0.000 description 5
• 208000024172 Cardiovascular disease Diseases 0.000 description 5
• 108010010234 HDL Lipoproteins Proteins 0.000 description 5
• 102000015779 HDL Lipoproteins Human genes 0.000 description 5
• 206010020772 Hypertension Diseases 0.000 description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 108010069201 VLDL Cholesterol Proteins 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 150000001602 bicycloalkyls Chemical group 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 208000029078 coronary artery disease Diseases 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• OZEYXHPIKLICLU-UHFFFAOYSA-N hydrazinyl(hydroxy)carbamic acid Chemical compound N(N)N(O)C(=O)O OZEYXHPIKLICLU-UHFFFAOYSA-N 0.000 description 5
• 201000001421 hyperglycemia Diseases 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 125000003386 piperidinyl group Chemical group 0.000 description 5
• 230000002265 prevention Effects 0.000 description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
• 239000011734 sodium Chemical class 0.000 description 5
• 208000011580 syndromic disease Diseases 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000004001 thioalkyl group Chemical group 0.000 description 5
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 208000035150 Hypercholesterolemia Diseases 0.000 description 4
• 102000016267 Leptin Human genes 0.000 description 4
• 108010092277 Leptin Proteins 0.000 description 4
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• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 4
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 206010048215 Xanthomatosis Diseases 0.000 description 4
• 235000011054 acetic acid Nutrition 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 239000000556 agonist Substances 0.000 description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 description 4
• 125000004069 aziridinyl group Chemical group 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
• 208000035475 disorder Diseases 0.000 description 4
• 239000003937 drug carrier Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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