JP2003520268A5

JP2003520268A5 -

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Publication number: JP2003520268A5
Authority: JP; Japan
Prior art keywords: phenyl; acid; ethoxy; substituted; pharmaceutically acceptable
Prior art date: 2001-01-17
Legal status : Granted

Application number

JP2001553262A

Other languages

English (en)

Japanese (ja)

Other versions

JP2003520268A (ja

JP4213385B2 (ja

Filing date

2001-01-17

Publication date

2006-01-05

2001-01-17 Application filed filed Critical

2001-01-17 Priority claimed from PCT/IN2001/000005 external-priority patent/WO2001053257A2/en

2003-07-02 Publication of JP2003520268A publication Critical patent/JP2003520268A/ja

2006-01-05 Publication of JP2003520268A5 publication Critical patent/JP2003520268A5/ja

2009-01-21 Application granted granted Critical

2009-01-21 Publication of JP4213385B2 publication Critical patent/JP4213385B2/ja

2021-01-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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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
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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
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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
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102000016267 Leptin 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
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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235000011054 acetic acid Nutrition 0.000 description 4
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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
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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
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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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JP2001553262A 2000-01-19 2001-01-17 低脂血、低コレステロール血活性を有する新規化合物、それらの製造方法ならびにそれらを含有する製剤組成物 Expired - Fee Related JP4213385B2 (ja)