JP2006273848A5 - - Google Patents
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- JP2006273848A5 JP2006273848A5 JP2006054782A JP2006054782A JP2006273848A5 JP 2006273848 A5 JP2006273848 A5 JP 2006273848A5 JP 2006054782 A JP2006054782 A JP 2006054782A JP 2006054782 A JP2006054782 A JP 2006054782A JP 2006273848 A5 JP2006273848 A5 JP 2006273848A5
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- 150000001875 compounds Chemical class 0.000 description 310
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 124
- -1 cinnamoyl compounds Chemical class 0.000 description 101
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- 125000005843 halogen group Chemical group 0.000 description 80
- 125000001424 substituent group Chemical group 0.000 description 79
- 239000000203 mixture Substances 0.000 description 75
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 70
- 125000004149 thio group Chemical group *S* 0.000 description 67
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 61
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 49
- 230000015572 biosynthetic process Effects 0.000 description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 46
- 238000003786 synthesis reaction Methods 0.000 description 46
- 230000002194 synthesizing Effects 0.000 description 46
- 238000005160 1H NMR spectroscopy Methods 0.000 description 42
- 125000004093 cyano group Chemical group *C#N 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 39
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 37
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N Tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 36
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- 229920003013 deoxyribonucleic acid Polymers 0.000 description 36
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- 238000006243 chemical reaction Methods 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 34
- 150000002430 hydrocarbons Chemical group 0.000 description 34
- 125000000304 alkynyl group Chemical group 0.000 description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 206010016654 Fibrosis Diseases 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 30
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- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 27
- 125000003342 alkenyl group Chemical group 0.000 description 26
- 125000004432 carbon atoms Chemical group C* 0.000 description 25
- 230000035897 transcription Effects 0.000 description 25
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 24
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 22
- 102000016359 Fibronectins Human genes 0.000 description 22
- 108010067306 Fibronectins Proteins 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 230000037320 fibronectin Effects 0.000 description 22
- 125000002947 alkylene group Chemical group 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- 125000004450 alkenylene group Chemical group 0.000 description 19
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- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000969 carrier Substances 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 238000009825 accumulation Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 13
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- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229960005188 collagen Drugs 0.000 description 12
- 229920001436 collagen Polymers 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 12
- 0 CC1=C(C)N(*)C(O)=CC1=O Chemical compound CC1=C(C)N(*)C(O)=CC1=O 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 230000014509 gene expression Effects 0.000 description 11
- AYMQCLGUHSIDFY-UHFFFAOYSA-N methyl 2-(3-formylphenoxy)acetate Chemical compound COC(=O)COC1=CC=CC(C=O)=C1 AYMQCLGUHSIDFY-UHFFFAOYSA-N 0.000 description 11
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 11
- TVMKRFHVCCARCE-UHFFFAOYSA-N N-(3-formylphenyl)-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC=CC(C=O)=C1 TVMKRFHVCCARCE-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 125000003302 alkenyloxy group Chemical group 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 229920000272 Oligonucleotide Polymers 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 9
- 125000004430 oxygen atoms Chemical group O* 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000006228 supernatant Substances 0.000 description 8
- 230000001629 suppression Effects 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 229910052770 Uranium Inorganic materials 0.000 description 7
- 125000005133 alkynyloxy group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
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- 239000000843 powder Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 235000013373 food additive Nutrition 0.000 description 6
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- WIRJPESFDDIBIW-UHFFFAOYSA-N 3-formyl-N-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=CC(C=O)=C1 WIRJPESFDDIBIW-UHFFFAOYSA-N 0.000 description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 5
- 208000009863 Chronic Kidney Failure Diseases 0.000 description 5
- 208000007342 Diabetic Nephropathy Diseases 0.000 description 5
- 206010061835 Diabetic nephropathy Diseases 0.000 description 5
- 206010038444 Renal failure chronic Diseases 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
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- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
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- 239000012091 fetal bovine serum Substances 0.000 description 5
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- 230000002103 transcriptional Effects 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 206010012601 Diabetes mellitus Diseases 0.000 description 4
- 208000010159 IGA Glomerulonephritis Diseases 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
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- SJRJJKPEHAURKC-UHFFFAOYSA-N n-methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- FNPICKJUBFBFFR-UHFFFAOYSA-N 3-acetyl-4-hydroxy-1H-1,8-naphthyridin-2-one Chemical compound C1=CN=C2NC(=O)C(C(=O)C)=C(O)C2=C1 FNPICKJUBFBFFR-UHFFFAOYSA-N 0.000 description 3
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- NFYQVXRKJWITJS-UHFFFAOYSA-N 1-(4-hydroxy-1,1-dioxo-2H-1$l^{6},2-benzothiazin-3-yl)ethanone Chemical compound C1=CC=C2S(=O)(=O)NC(C(=O)C)=C(O)C2=C1 NFYQVXRKJWITJS-UHFFFAOYSA-N 0.000 description 2
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