JP2011530525A5 - - Google Patents
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- JP2011530525A5 JP2011530525A5 JP2011522226A JP2011522226A JP2011530525A5 JP 2011530525 A5 JP2011530525 A5 JP 2011530525A5 JP 2011522226 A JP2011522226 A JP 2011522226A JP 2011522226 A JP2011522226 A JP 2011522226A JP 2011530525 A5 JP2011530525 A5 JP 2011530525A5
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- JP
- Japan
- Prior art keywords
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- compound
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- 150000001875 compounds Chemical class 0.000 claims 31
- 239000000203 mixture Substances 0.000 claims 25
- -1 methoxy, ethoxy Chemical group 0.000 claims 21
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 150000001412 amines Chemical class 0.000 claims 8
- 230000000598 lipoate effect Effects 0.000 claims 8
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 6
- 150000008430 aromatic amides Chemical class 0.000 claims 6
- 125000000524 functional group Chemical group 0.000 claims 6
- 235000019136 lipoic acid Nutrition 0.000 claims 6
- 229960002663 thioctic acid Drugs 0.000 claims 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
- 125000003977 lipoyl group Chemical group S1SC(C([H])([H])C(C(C(C(=O)[*])([H])[H])([H])[H])([H])[H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001560 (R)-dihydrolipoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@](S[H])([H])C([H])([H])C([H])([H])S[H] 0.000 claims 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 4
- 102000023984 PPAR alpha Human genes 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 229940123464 Thiazolidinedione Drugs 0.000 claims 4
- 150000001448 anilines Chemical class 0.000 claims 4
- 125000004494 ethyl ester group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- BYOPSCVORPQJID-UHFFFAOYSA-N 6-nitro-1,3-benzodioxol-5-ol Chemical compound C1=C([N+]([O-])=O)C(O)=CC2=C1OCO2 BYOPSCVORPQJID-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 230000027455 binding Effects 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 3
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims 2
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 claims 2
- QNJMUNKUQDDPCI-UHFFFAOYSA-N 1,3-benzodioxol-5-yl acetate Chemical compound CC(=O)OC1=CC=C2OCOC2=C1 QNJMUNKUQDDPCI-UHFFFAOYSA-N 0.000 claims 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 2
- 239000005541 ACE inhibitor Substances 0.000 claims 2
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 2
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 241000723347 Cinnamomum Species 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical class [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 claims 2
- 102000000853 LDL receptors Human genes 0.000 claims 2
- 108010001831 LDL receptors Proteins 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 150000008431 aliphatic amides Chemical class 0.000 claims 2
- 229940125364 angiotensin receptor blocker Drugs 0.000 claims 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 159000000032 aromatic acids Chemical class 0.000 claims 2
- 239000002876 beta blocker Substances 0.000 claims 2
- 229940097320 beta blocking agent Drugs 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 235000017803 cinnamon Nutrition 0.000 claims 2
- 230000035602 clotting Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 2
- 239000003925 fat Substances 0.000 claims 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims 2
- 229940114124 ferulic acid Drugs 0.000 claims 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims 2
- 235000001785 ferulic acid Nutrition 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 229910052736 halogen Chemical class 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 150000002537 isoquinolines Chemical class 0.000 claims 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Chemical class OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 230000007505 plaque formation Effects 0.000 claims 2
- 150000003147 proline derivatives Chemical class 0.000 claims 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- CUKWUWBLQQDQAC-VEQWQPCFSA-N (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-ox Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 CUKWUWBLQQDQAC-VEQWQPCFSA-N 0.000 claims 1
- DECGMUJJYLXRPA-UHFFFAOYSA-N (6-nitro-1,3-benzodioxol-5-yl) acetate Chemical compound C1=C([N+]([O-])=O)C(OC(=O)C)=CC2=C1OCO2 DECGMUJJYLXRPA-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 102000005862 Angiotensin II Human genes 0.000 claims 1
- 101800000733 Angiotensin-2 Proteins 0.000 claims 1
- 102000014914 Carrier Proteins Human genes 0.000 claims 1
- 108010078791 Carrier Proteins Proteins 0.000 claims 1
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims 1
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 102000007330 LDL Lipoproteins Human genes 0.000 claims 1
- 102000003945 NF-kappa B Human genes 0.000 claims 1
- 108010057466 NF-kappa B Proteins 0.000 claims 1
- 108010028924 PPAR alpha Proteins 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 102000000536 PPAR gamma Human genes 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010047139 Vasoconstriction Diseases 0.000 claims 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims 1
- 229960004373 acetylcholine Drugs 0.000 claims 1
- 229950006323 angiotensin ii Drugs 0.000 claims 1
- 230000003416 augmentation Effects 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 235000015872 dietary supplement Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 230000008595 infiltration Effects 0.000 claims 1
- 238000001764 infiltration Methods 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 210000002540 macrophage Anatomy 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 210000002460 smooth muscle Anatomy 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000025033 vasoconstriction Effects 0.000 claims 1
- 230000024883 vasodilation Effects 0.000 claims 1
- BRFITNWJRUMLQL-VQHVLOKHSA-N COc1cc(/C=C/C(Oc(cc2OCCc2c2)c2OC(CCCCC(CCS)S)=O)=O)ccc1O Chemical compound COc1cc(/C=C/C(Oc(cc2OCCc2c2)c2OC(CCCCC(CCS)S)=O)=O)ccc1O BRFITNWJRUMLQL-VQHVLOKHSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8642508P | 2008-08-05 | 2008-08-05 | |
| US61/086,425 | 2008-08-05 | ||
| PCT/US2009/052893 WO2010017323A1 (en) | 2008-08-05 | 2009-08-05 | Novel methylenedioxy phenolic compounds and their use to treat disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011530525A JP2011530525A (ja) | 2011-12-22 |
| JP2011530525A5 true JP2011530525A5 (https=) | 2012-09-20 |
Family
ID=41172398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011522226A Withdrawn JP2011530525A (ja) | 2008-08-05 | 2009-08-05 | 新規なメチレンジオキシフェノール系化合物および疾患処置のためのそれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8198317B2 (https=) |
| EP (1) | EP2324005A1 (https=) |
| JP (1) | JP2011530525A (https=) |
| KR (1) | KR20110042108A (https=) |
| CN (1) | CN102149702A (https=) |
| AU (1) | AU2009279667A1 (https=) |
| BR (1) | BRPI0917262A2 (https=) |
| CA (1) | CA2733430A1 (https=) |
| IL (1) | IL211076A0 (https=) |
| RU (1) | RU2011108587A (https=) |
| WO (1) | WO2010017323A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120129818A1 (en) * | 2009-04-23 | 2012-05-24 | Desikan Rajagopal | Compositions and Methods for Treatment of Cardiovascular Disease |
| CN106957298B (zh) * | 2017-04-18 | 2019-07-16 | 湖南中医药大学 | 一种硫辛酸苯酚酯衍生物及其制备方法和应用 |
| CN110305102B (zh) * | 2019-08-13 | 2020-11-24 | 陕西中医药大学 | 1,3-苯并二噁茂天然多酚酸酯类化合物及其降血脂应用 |
| CN112745291A (zh) * | 2019-10-29 | 2021-05-04 | 浙江大学宁波理工学院 | 一种具有HMG-CoA还原酶抑制活性的化合物、药物组合物及应用 |
| US11306076B2 (en) * | 2020-05-11 | 2022-04-19 | Xi'an Taikomed Pharmaceutical Technology Co., Ltd. | Silibinin lipoic acid ester with hepatoprotective activity and a method of preparing the same |
| CN115047092B (zh) * | 2022-04-07 | 2023-10-20 | 济宁医学院 | 一种血管紧张素转移酶ii抑制剂的筛选方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010031275A1 (en) * | 1998-02-09 | 2001-10-18 | Forse R Armour | Sesamol inhibitor of delta-5-desaturase activity and uses therefor |
| ATE305467T1 (de) | 2001-01-31 | 2005-10-15 | Pfizer Prod Inc | Als inhibitoren von pde4-isozymen geeignete etherderivate |
| ES2239203T3 (es) * | 2001-01-31 | 2005-09-16 | Pfizer Products Inc. | Derivados nicotinamida y sus mimeticos como inhibidores de isozimas pde4. |
-
2009
- 2009-08-05 RU RU2011108587/04A patent/RU2011108587A/ru not_active Application Discontinuation
- 2009-08-05 BR BRPI0917262A patent/BRPI0917262A2/pt not_active Application Discontinuation
- 2009-08-05 AU AU2009279667A patent/AU2009279667A1/en not_active Abandoned
- 2009-08-05 KR KR1020117005383A patent/KR20110042108A/ko not_active Withdrawn
- 2009-08-05 JP JP2011522226A patent/JP2011530525A/ja not_active Withdrawn
- 2009-08-05 US US12/536,295 patent/US8198317B2/en not_active Expired - Fee Related
- 2009-08-05 WO PCT/US2009/052893 patent/WO2010017323A1/en not_active Ceased
- 2009-08-05 CN CN2009801354528A patent/CN102149702A/zh active Pending
- 2009-08-05 CA CA2733430A patent/CA2733430A1/en not_active Abandoned
- 2009-08-05 EP EP09791197A patent/EP2324005A1/en not_active Withdrawn
-
2011
- 2011-02-03 IL IL211076A patent/IL211076A0/en unknown
-
2012
- 2012-06-12 US US13/494,606 patent/US20130157986A1/en not_active Abandoned
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