TWI359148B - - Google Patents

Info

Publication number

TWI359148B

TWI359148B TW094137797A TW94137797A TWI359148B TW I359148 B TWI359148 B TW I359148B TW 094137797 A TW094137797 A TW 094137797A TW 94137797 A TW94137797 A TW 94137797A TW I359148 B TWI359148 B TW I359148B

Authority

TW

Taiwan

Prior art keywords

group

substituent

alkyl

substituted

alkoxy

Prior art date

2004-10-29

Links

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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 178
• 150000003839 salts Chemical class 0.000 claims abstract description 95
• 239000012453 solvate Substances 0.000 claims abstract description 61
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 40
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
• 239000003814 drug Substances 0.000 claims abstract description 28
• 208000004930 Fatty Liver Diseases 0.000 claims abstract description 20
• 208000008589 Obesity Diseases 0.000 claims abstract description 20
• 235000020824 obesity Nutrition 0.000 claims abstract description 20
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 20
• 208000010706 fatty liver disease Diseases 0.000 claims abstract description 19
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 19
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 19
• 206010019708 Hepatic steatosis Diseases 0.000 claims abstract description 18
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
• 231100000240 steatosis hepatitis Toxicity 0.000 claims abstract description 18
• 206010020772 Hypertension Diseases 0.000 claims abstract description 14
• 230000003449 preventive effect Effects 0.000 claims abstract description 14
• 230000037356 lipid metabolism Effects 0.000 claims abstract description 11
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 7
• 230000005856 abnormality Effects 0.000 claims abstract description 5
• 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract 4
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract 2
• 125000001424 substituent group Chemical group 0.000 claims description 509
• -1 3-oxadiazolyl Chemical group 0.000 claims description 210
• 239000013589 supplement Substances 0.000 claims description 151
• 125000000217 alkyl group Chemical group 0.000 claims description 148
• 125000003545 alkoxy group Chemical group 0.000 claims description 118
• 229910052736 halogen Inorganic materials 0.000 claims description 86
• 150000002367 halogens Chemical class 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 71
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
• 239000002253 acid Substances 0.000 claims description 48
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
• 239000003795 chemical substances by application Substances 0.000 claims description 44
• 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 44
• 239000007789 gas Substances 0.000 claims description 35
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 35
• 150000001716 carbazoles Chemical class 0.000 claims description 34
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 33
• 125000004414 alkyl thio group Chemical group 0.000 claims description 32
• 125000001188 haloalkyl group Chemical group 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 27
• 150000001412 amines Chemical class 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 239000002904 solvent Substances 0.000 claims description 23
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
• 239000005557 antagonist Substances 0.000 claims description 19
• 125000001931 aliphatic group Chemical group 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 150000002923 oximes Chemical class 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 239000002689 soil Substances 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 15
• 235000011054 acetic acid Nutrition 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
• 125000006612 decyloxy group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 14
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 125000006611 nonyloxy group Chemical group 0.000 claims description 12
• 235000019260 propionic acid Nutrition 0.000 claims description 12
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
• 125000002723 alicyclic group Chemical group 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 10
• 239000004480 active ingredient Substances 0.000 claims description 10
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
• 210000001596 intra-abdominal fat Anatomy 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
• 239000005711 Benzoic acid Substances 0.000 claims description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 9
• 235000010233 benzoic acid Nutrition 0.000 claims description 9
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 9
• 125000005936 piperidyl group Chemical group 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000005577 anthracene group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 235000013336 milk Nutrition 0.000 claims description 8
• 239000008267 milk Substances 0.000 claims description 8
• 210000004080 milk Anatomy 0.000 claims description 8
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 229930195733 hydrocarbon Natural products 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 238000012546 transfer Methods 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical compound CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 claims description 6
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
• 230000001476 alcoholic effect Effects 0.000 claims description 6
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 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 6
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 6
• 229940067157 phenylhydrazine Drugs 0.000 claims description 6
• 230000000069 prophylactic effect Effects 0.000 claims description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 6
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 5
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 210000003296 saliva Anatomy 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
• PMNLUUOXGOOLSP-UHFFFAOYSA-N alpha-mercaptopropionic acid Natural products CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 239000005864 Sulphur Substances 0.000 claims description 3
• 150000001336 alkenes Chemical group 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 238000001354 calcination Methods 0.000 claims description 3
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
• 150000002429 hydrazines Chemical class 0.000 claims description 3
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 229910052720 vanadium Inorganic materials 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• ONEKODVPFBOORO-UHFFFAOYSA-N 2-methyl lauric acid Chemical compound CCCCCCCCCCC(C)C(O)=O ONEKODVPFBOORO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
• 241000699670 Mus sp. Species 0.000 claims description 2
• 206010036790 Productive cough Diseases 0.000 claims description 2
• 206010039424 Salivary hypersecretion Diseases 0.000 claims description 2
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
• 125000004653 anthracenylene group Chemical group 0.000 claims description 2
• 125000005418 aryl aryl group Chemical group 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• 235000012054 meals Nutrition 0.000 claims description 2
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000001725 pyrenyl group Chemical group 0.000 claims description 2
• 208000026451 salivation Diseases 0.000 claims description 2
• 210000003802 sputum Anatomy 0.000 claims description 2
• 208000024794 sputum Diseases 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
• KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
• QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical group N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 claims 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
• 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims 2
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• ZWKQYTCYQWWVQJ-UHFFFAOYSA-N 2-methoxypentanoic acid Chemical compound CCCC(OC)C(O)=O ZWKQYTCYQWWVQJ-UHFFFAOYSA-N 0.000 claims 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 1
• DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims 1
• 241000206761 Bacillariophyta Species 0.000 claims 1
• 208000032928 Dyslipidaemia Diseases 0.000 claims 1
• 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
• 241001494479 Pecora Species 0.000 claims 1
• 241000555745 Sciuridae Species 0.000 claims 1
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• YEJAJYAHJQIWNU-UHFFFAOYSA-N azelastine hydrochloride Chemical compound Cl.C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YEJAJYAHJQIWNU-UHFFFAOYSA-N 0.000 claims 1
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 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 1
• 239000000796 flavoring agent Substances 0.000 claims 1
• 235000019634 flavors Nutrition 0.000 claims 1
• 125000005567 fluorenylene group Chemical group 0.000 claims 1
• 150000002473 indoazoles Chemical class 0.000 claims 1
• 230000004060 metabolic process Effects 0.000 claims 1
• HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
• 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
• 125000003386 piperidinyl group Chemical group 0.000 claims 1
• NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 claims 1
• 125000004151 quinonyl group Chemical group 0.000 claims 1
• KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical group [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims 1
• 210000001635 urinary tract Anatomy 0.000 claims 1
• 230000009278 visceral effect Effects 0.000 abstract description 8
• 210000000577 adipose tissue Anatomy 0.000 abstract description 7
• 201000005577 familial hyperlipidemia Diseases 0.000 abstract description 3
• 230000001603 reducing effect Effects 0.000 abstract description 3
• 125000006832 (C1-C10) alkylene group Chemical group 0.000 abstract 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
• 208000002705 Glucose Intolerance Diseases 0.000 abstract 1
• 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
• 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
• 201000009104 prediabetes syndrome Diseases 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 279
• 238000003786 synthesis reaction Methods 0.000 description 108
• 239000002585 base Substances 0.000 description 100
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• 230000015572 biosynthetic process Effects 0.000 description 91
• 238000000034 method Methods 0.000 description 91
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
• 239000000243 solution Substances 0.000 description 77
• 238000006243 chemical reaction Methods 0.000 description 56
• 238000012360 testing method Methods 0.000 description 53
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 52
• 239000000203 mixture Substances 0.000 description 48
• 239000013078 crystal Substances 0.000 description 47
• 235000019441 ethanol Nutrition 0.000 description 46
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
• 238000005481 NMR spectroscopy Methods 0.000 description 42
• 230000003595 spectral effect Effects 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• 230000000694 effects Effects 0.000 description 35
• 230000002829 reductive effect Effects 0.000 description 34
• 238000005160 1H NMR spectroscopy Methods 0.000 description 33
• 235000019439 ethyl acetate Nutrition 0.000 description 33
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 32
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 229910052751 metal Inorganic materials 0.000 description 28
• 239000002184 metal Substances 0.000 description 28
• 239000012442 inert solvent Substances 0.000 description 27
• 210000004027 cell Anatomy 0.000 description 26
• 210000002706 plastid Anatomy 0.000 description 25
• 239000000843 powder Substances 0.000 description 24
• 239000011734 sodium Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 22
• 230000003287 optical effect Effects 0.000 description 22
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 18
• 229960004592 isopropanol Drugs 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 238000003756 stirring Methods 0.000 description 18
• 238000004519 manufacturing process Methods 0.000 description 17
• 108020004414 DNA Proteins 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• 238000001914 filtration Methods 0.000 description 16
• 108090000623 proteins and genes Proteins 0.000 description 16
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
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