TWI359148B - - Google Patents
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- 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
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- Prior art keywords
- group
- substituent
- alkyl
- substituted
- alkoxy
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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
- 239000000126 substance Substances 0.000 description 15
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| JP2004316872 | 2004-10-29 |
Publications (2)
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| TW200635922A TW200635922A (en) | 2006-10-16 |
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| TW094137797A TW200635922A (en) | 2004-10-29 | 2005-10-28 | Carbazole derivatives, solvents thereof and pharmaceutically acceptable salts thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8329913B2 (enExample) |
| EP (1) | EP1852433B1 (enExample) |
| JP (1) | JP3997491B2 (enExample) |
| KR (1) | KR101223820B1 (enExample) |
| CN (1) | CN101048402B (enExample) |
| AT (1) | ATE534646T1 (enExample) |
| AU (1) | AU2005297800B2 (enExample) |
| CA (1) | CA2585642C (enExample) |
| CY (1) | CY1112649T1 (enExample) |
| DK (1) | DK1852433T3 (enExample) |
| ES (1) | ES2378177T3 (enExample) |
| PL (1) | PL1852433T3 (enExample) |
| PT (1) | PT1852433E (enExample) |
| SI (1) | SI1852433T1 (enExample) |
| TW (1) | TW200635922A (enExample) |
| WO (1) | WO2006046779A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7393181B2 (en) | 2004-09-17 | 2008-07-01 | The Penn State Research Foundation | Expandable impeller pump |
| AU2007230945B2 (en) | 2006-03-23 | 2013-05-02 | The Penn State Research Foundation | Heart assist device with expandable impeller pump |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| EP2185544B1 (en) | 2007-07-19 | 2014-11-26 | Cymabay Therapeutics, Inc. | N-azacyclic substituted pyrrole, pyrazole, imidazole, triazole and tetrazole derivatives as agonists of the rup3 or gpr119 for the treatment of diabetes and metabolic disorders |
| US8535211B2 (en) | 2009-07-01 | 2013-09-17 | Thoratec Corporation | Blood pump with expandable cannula |
| EP2483281B1 (en) | 2009-10-01 | 2014-06-04 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
| BR112012032248A2 (pt) | 2010-06-23 | 2016-09-13 | Metabolex Inc | composições de 5-etil-2-{4-[-4(-4-tetrazol-1-il-fenoximetil)-tiazol-2-il]-piperidin-1-il}-pirimidina |
| CN102382037B (zh) * | 2010-09-03 | 2016-01-20 | 中国医学科学院药物研究所 | 苯丙酸类化合物及其制法和药物用途 |
| US8597170B2 (en) | 2011-01-05 | 2013-12-03 | Thoratec Corporation | Catheter pump |
| US8485961B2 (en) | 2011-01-05 | 2013-07-16 | Thoratec Corporation | Impeller housing for percutaneous heart pump |
| WO2012094641A2 (en) | 2011-01-06 | 2012-07-12 | Thoratec Corporation | Percutaneous heart pump |
| WO2012094535A2 (en) | 2011-01-06 | 2012-07-12 | Thoratec Corporation | Percutaneous heart pump |
| US9872947B2 (en) | 2012-05-14 | 2018-01-23 | Tc1 Llc | Sheath system for catheter pump |
| US8721517B2 (en) | 2012-05-14 | 2014-05-13 | Thoratec Corporation | Impeller for catheter pump |
| US9327067B2 (en) | 2012-05-14 | 2016-05-03 | Thoratec Corporation | Impeller for catheter pump |
| US9446179B2 (en) | 2012-05-14 | 2016-09-20 | Thoratec Corporation | Distal bearing support |
| DE102013008159A1 (de) | 2012-05-14 | 2013-11-14 | Thoratec Corporation | Mantelsystem für Katheterpumpe |
| GB2504176A (en) | 2012-05-14 | 2014-01-22 | Thoratec Corp | Collapsible impeller for catheter pump |
| EP4186557A1 (en) | 2012-07-03 | 2023-05-31 | Tc1 Llc | Motor assembly for catheter pump |
| US9358329B2 (en) | 2012-07-03 | 2016-06-07 | Thoratec Corporation | Catheter pump |
| US9421311B2 (en) | 2012-07-03 | 2016-08-23 | Thoratec Corporation | Motor assembly for catheter pump |
| US11077294B2 (en) | 2013-03-13 | 2021-08-03 | Tc1 Llc | Sheath assembly for catheter pump |
| JP6530367B2 (ja) | 2013-03-13 | 2019-06-12 | ティーシーワン エルエルシー | 流体導出入システム |
| US11033728B2 (en) | 2013-03-13 | 2021-06-15 | Tc1 Llc | Fluid handling system |
| EP4190376A1 (en) | 2013-03-15 | 2023-06-07 | Tc1 Llc | Catheter pump assembly including a stator |
| US9308302B2 (en) | 2013-03-15 | 2016-04-12 | Thoratec Corporation | Catheter pump assembly including a stator |
| US10583232B2 (en) | 2014-04-15 | 2020-03-10 | Tc1 Llc | Catheter pump with off-set motor position |
| WO2015160990A1 (en) | 2014-04-15 | 2015-10-22 | Thoratec Corporation | Catheter pump introducer systems and methods |
| EP3479854A1 (en) | 2014-04-15 | 2019-05-08 | Tc1 Llc | Catheter pump with access ports |
| WO2015160943A1 (en) | 2014-04-15 | 2015-10-22 | Thoratec Corporation | Sensors for catheter pumps |
| WO2016028644A1 (en) | 2014-08-18 | 2016-02-25 | Thoratec Corporation | Guide features for percutaneous catheter pump |
| US9675738B2 (en) | 2015-01-22 | 2017-06-13 | Tc1 Llc | Attachment mechanisms for motor of catheter pump |
| WO2016118781A2 (en) | 2015-01-22 | 2016-07-28 | Thoratec Corporation | Motor assembly with heat exchanger for catheter pump |
| EP3247420B1 (en) | 2015-01-22 | 2019-10-02 | Tc1 Llc | Reduced rotational mass motor assembly for catheter pump |
| US9907890B2 (en) | 2015-04-16 | 2018-03-06 | Tc1 Llc | Catheter pump with positioning brace |
| EP3804804A1 (en) | 2016-07-21 | 2021-04-14 | Tc1 Llc | Fluid seals for catheter pump motor assembly |
| EP3808402A1 (en) | 2016-07-21 | 2021-04-21 | Tc1 Llc | Gas-filled chamber for catheter pump motor assembly |
| WO2018026890A1 (en) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
| JP7479278B2 (ja) | 2017-10-06 | 2024-05-08 | ギリアード サイエンシーズ， インコーポレイテッド | Ａｃｃ阻害剤を含む併用療法 |
| CN116327749A (zh) * | 2023-04-21 | 2023-06-27 | 重庆医科大学 | Gw9662制备治疗非酒精性脂肪性肝炎药物的应用 |
Family Cites Families (11)
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| HUT76923A (hu) | 1994-07-27 | 1998-01-28 | Sankyo Company Limited | Muszkarinreceptorokra alloszterikus hatást kifejtő heterociklusos vegyületek |
| JP2001503055A (ja) | 1996-10-30 | 2001-03-06 | イーライ・リリー・アンド・カンパニー | 置換三環化合物群 |
| MY125942A (en) * | 1999-09-07 | 2006-09-29 | Upjohn Co | Aminoalkoxy carbazoles for the treatment of cns diseases |
| AU7559600A (en) | 1999-10-15 | 2001-04-23 | Shionogi & Co., Ltd. | V type and/or x type spla2 inhibitors |
| AU2001267825A1 (en) | 2000-06-29 | 2002-01-08 | Shionogi And Co., Ltd. | Remedies for cirrhosis |
| EP1300159B1 (en) | 2000-06-29 | 2007-10-10 | Anthera Pharmaceuticals, Inc. | Remedies for cancer |
| AU2001267826A1 (en) | 2000-06-29 | 2002-01-08 | Shionogi And Co., Ltd. | Remedies for alzheimer's disease |
| TWI314457B (enExample) | 2001-03-19 | 2009-09-11 | Shionogi & Co | |
| ATE353876T1 (de) | 2001-03-28 | 2007-03-15 | Lilly Co Eli | Substituierte carbazole als inhibitoren von spla2 |
| WO2004024939A2 (en) | 2002-09-13 | 2004-03-25 | Georgetown University | Ligands for the peroxisome proliferator-activated receptor, and methods of use thereof |
| US7268157B2 (en) | 2002-11-26 | 2007-09-11 | Shenzhen Chipscreen Biosciences, Ltd. | Substituted arylalcanoic acid derivatives as PPAR pan agonists with potent antihyperglycemic and antihyperlipidemic activity |
-
2005
- 2005-10-28 PT PT05799893T patent/PT1852433E/pt unknown
- 2005-10-28 AT AT05799893T patent/ATE534646T1/de active
- 2005-10-28 PL PL05799893T patent/PL1852433T3/pl unknown
- 2005-10-28 US US11/666,631 patent/US8329913B2/en not_active Expired - Fee Related
- 2005-10-28 CA CA2585642A patent/CA2585642C/en not_active Expired - Fee Related
- 2005-10-28 CN CN2005800370489A patent/CN101048402B/zh not_active Expired - Fee Related
- 2005-10-28 SI SI200531453T patent/SI1852433T1/sl unknown
- 2005-10-28 WO PCT/JP2005/020250 patent/WO2006046779A1/ja not_active Ceased
- 2005-10-28 DK DK05799893.2T patent/DK1852433T3/da active
- 2005-10-28 KR KR1020077009734A patent/KR101223820B1/ko not_active Expired - Fee Related
- 2005-10-28 ES ES05799893T patent/ES2378177T3/es not_active Expired - Lifetime
- 2005-10-28 EP EP05799893A patent/EP1852433B1/en not_active Expired - Lifetime
- 2005-10-28 TW TW094137797A patent/TW200635922A/zh not_active IP Right Cessation
- 2005-10-28 JP JP2006542433A patent/JP3997491B2/ja not_active Expired - Fee Related
- 2005-10-28 AU AU2005297800A patent/AU2005297800B2/en not_active Ceased
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2012
- 2012-01-25 CY CY20121100086T patent/CY1112649T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2006046779A1 (ja) | 2008-05-22 |
| AU2005297800A1 (en) | 2006-05-04 |
| TW200635922A (en) | 2006-10-16 |
| EP1852433A4 (en) | 2010-07-21 |
| CA2585642C (en) | 2013-04-02 |
| CY1112649T1 (el) | 2016-02-10 |
| EP1852433A1 (en) | 2007-11-07 |
| KR20070072554A (ko) | 2007-07-04 |
| AU2005297800B2 (en) | 2011-02-03 |
| US8329913B2 (en) | 2012-12-11 |
| CN101048402B (zh) | 2011-11-09 |
| ATE534646T1 (de) | 2011-12-15 |
| DK1852433T3 (da) | 2012-01-30 |
| CA2585642A1 (en) | 2006-05-04 |
| PT1852433E (pt) | 2012-02-08 |
| WO2006046779A1 (ja) | 2006-05-04 |
| US20100286210A1 (en) | 2010-11-11 |
| JP3997491B2 (ja) | 2007-10-24 |
| CN101048402A (zh) | 2007-10-03 |
| KR101223820B1 (ko) | 2013-01-17 |
| SI1852433T1 (sl) | 2012-06-29 |
| PL1852433T3 (pl) | 2012-05-31 |
| ES2378177T3 (es) | 2012-04-09 |
| EP1852433B1 (en) | 2011-11-23 |
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