RU2011108587A - Новые метилендиоксифенольные соединения и их применение для лечения заболеваний - Google Patents
Новые метилендиоксифенольные соединения и их применение для лечения заболеваний Download PDFInfo
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- RU2011108587A RU2011108587A RU2011108587/04A RU2011108587A RU2011108587A RU 2011108587 A RU2011108587 A RU 2011108587A RU 2011108587/04 A RU2011108587/04 A RU 2011108587/04A RU 2011108587 A RU2011108587 A RU 2011108587A RU 2011108587 A RU2011108587 A RU 2011108587A
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- XRSKRSVTUVLURN-UHFFFAOYSA-N 1,3-benzodioxol-4-ol Chemical class OC1=CC=CC2=C1OCO2 XRSKRSVTUVLURN-UHFFFAOYSA-N 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- -1 methoxy, ethoxy Chemical group 0.000 claims abstract 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract 11
- 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 abstract 10
- 235000019136 lipoic acid Nutrition 0.000 claims abstract 9
- 229960002663 thioctic acid Drugs 0.000 claims abstract 9
- 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 abstract 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract 8
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract 8
- 150000008431 aliphatic amides Chemical class 0.000 claims abstract 8
- 150000003973 alkyl amines Chemical class 0.000 claims abstract 8
- 150000001408 amides Chemical group 0.000 claims abstract 8
- 150000001412 amines Chemical class 0.000 claims abstract 8
- 150000008430 aromatic amides Chemical class 0.000 claims abstract 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 8
- 125000000524 functional group Chemical group 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 8
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims abstract 7
- 229940123464 Thiazolidinedione Drugs 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Chemical group 0.000 claims abstract 6
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims abstract 4
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 claims abstract 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract 4
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims abstract 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical group CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 4
- 150000007513 acids Chemical class 0.000 claims abstract 4
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract 4
- 159000000032 aromatic acids Chemical class 0.000 claims abstract 4
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract 4
- 229930016911 cinnamic acid Natural products 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 125000004494 ethyl ester group Chemical group 0.000 claims abstract 4
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims abstract 4
- 235000001785 ferulic acid Nutrition 0.000 claims abstract 4
- 229940114124 ferulic acid Drugs 0.000 claims abstract 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims abstract 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims 26
- 230000000598 lipoate effect Effects 0.000 claims 10
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 239000000556 agonist Substances 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- 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 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 4
- 108010016731 PPAR gamma Proteins 0.000 claims 4
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 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 3
- QNJMUNKUQDDPCI-UHFFFAOYSA-N 1,3-benzodioxol-5-yl acetate Chemical compound CC(=O)OC1=CC=C2OCOC2=C1 QNJMUNKUQDDPCI-UHFFFAOYSA-N 0.000 claims 3
- 239000005541 ACE inhibitor Substances 0.000 claims 3
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 3
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 3
- 101150014691 PPARA gene Proteins 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 3
- 229940125364 angiotensin receptor blocker Drugs 0.000 claims 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 3
- 239000002876 beta blocker Substances 0.000 claims 3
- 229940097320 beta blocking agent Drugs 0.000 claims 3
- 230000029087 digestion Effects 0.000 claims 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims 3
- 229940125753 fibrate Drugs 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 150000002537 isoquinolines Chemical class 0.000 claims 3
- 208000017169 kidney disease Diseases 0.000 claims 3
- 229960003512 nicotinic acid Drugs 0.000 claims 3
- 235000001968 nicotinic acid Nutrition 0.000 claims 3
- 239000011664 nicotinic acid Substances 0.000 claims 3
- 150000003147 proline derivatives Chemical class 0.000 claims 3
- 208000023516 stroke disease Diseases 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 2
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims 2
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000000853 LDL receptors Human genes 0.000 claims 2
- 108010001831 LDL receptors Proteins 0.000 claims 2
- 102000023984 PPAR alpha Human genes 0.000 claims 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 229940127218 antiplatelet drug Drugs 0.000 claims 2
- 210000000709 aorta Anatomy 0.000 claims 2
- 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 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- 230000007505 plaque formation Effects 0.000 claims 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 208000019553 vascular disease 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
- 102000005862 Angiotensin II Human genes 0.000 claims 1
- 101800000733 Angiotensin-2 Proteins 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 102000007330 LDL Lipoproteins Human genes 0.000 claims 1
- 108010057466 NF-kappa B Proteins 0.000 claims 1
- 102100023050 Nuclear factor NF-kappa-B p105 subunit Human genes 0.000 claims 1
- 102100035100 Transcription factor p65 Human genes 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 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
- 238000004220 aggregation Methods 0.000 claims 1
- 230000002776 aggregation Effects 0.000 claims 1
- 229950006323 angiotensin ii Drugs 0.000 claims 1
- 230000027455 binding Effects 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 229940107161 cholesterol Drugs 0.000 claims 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 1
- 150000001840 cholesterol esters Chemical class 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
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- 230000008021 deposition Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 235000015872 dietary supplement Nutrition 0.000 claims 1
- 230000008595 infiltration Effects 0.000 claims 1
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- 229940125396 insulin Drugs 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 230000002265 prevention Effects 0.000 claims 1
- 229940121649 protein inhibitor Drugs 0.000 claims 1
- 239000012268 protein inhibitor Substances 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
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- 208000024891 symptom Diseases 0.000 claims 1
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- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical group [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
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- 0 *c(cc1OC(CNC(CCCCC2SSCC2)=O)Oc1c1)c1O Chemical compound *c(cc1OC(CNC(CCCCC2SSCC2)=O)Oc1c1)c1O 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8642508P | 2008-08-05 | 2008-08-05 | |
| US61/086,425 | 2008-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011108587A true RU2011108587A (ru) | 2012-09-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011108587/04A RU2011108587A (ru) | 2008-08-05 | 2009-08-05 | Новые метилендиоксифенольные соединения и их применение для лечения заболеваний |
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
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009279667A1 (en) | 2010-02-11 |
| KR20110042108A (ko) | 2011-04-22 |
| EP2324005A1 (en) | 2011-05-25 |
| CN102149702A (zh) | 2011-08-10 |
| US20100035849A1 (en) | 2010-02-11 |
| BRPI0917262A2 (pt) | 2015-11-10 |
| JP2011530525A (ja) | 2011-12-22 |
| US20130157986A1 (en) | 2013-06-20 |
| CA2733430A1 (en) | 2010-02-11 |
| US8198317B2 (en) | 2012-06-12 |
| WO2010017323A1 (en) | 2010-02-11 |
| IL211076A0 (en) | 2011-04-28 |
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Legal Events
| Date | Code | Title | Description |
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20120912 |