AU783855B2 - Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds - Google Patents
Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds Download PDFInfo
- Publication number
- AU783855B2 AU783855B2 AU68144/00A AU6814400A AU783855B2 AU 783855 B2 AU783855 B2 AU 783855B2 AU 68144/00 A AU68144/00 A AU 68144/00A AU 6814400 A AU6814400 A AU 6814400A AU 783855 B2 AU783855 B2 AU 783855B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- pyridoxal
- compound
- compound selected
- angiotensin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 237
- 239000000203 mixture Substances 0.000 title claims description 116
- 230000002526 effect on cardiovascular system Effects 0.000 title claims description 112
- 150000003223 pyridoxals Chemical class 0.000 title claims description 63
- 208000024172 Cardiovascular disease Diseases 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims description 126
- 230000001225 therapeutic effect Effects 0.000 claims description 102
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims description 89
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 74
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 claims description 74
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 58
- 239000000480 calcium channel blocker Substances 0.000 claims description 58
- 239000005541 ACE inhibitor Substances 0.000 claims description 57
- 239000000674 adrenergic antagonist Substances 0.000 claims description 57
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 57
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical group SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims description 54
- 229960000830 captopril Drugs 0.000 claims description 54
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical group C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 229960001722 verapamil Drugs 0.000 claims description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 239000002934 diuretic Substances 0.000 claims description 50
- -1 fosinipril Chemical compound 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 47
- 241000124008 Mammalia Species 0.000 claims description 43
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 42
- 229960003581 pyridoxal Drugs 0.000 claims description 42
- 235000008164 pyridoxal Nutrition 0.000 claims description 42
- 239000011674 pyridoxal Substances 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 37
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 37
- 235000008151 pyridoxamine Nutrition 0.000 claims description 37
- 239000011699 pyridoxamine Substances 0.000 claims description 37
- 239000003963 antioxidant agent Substances 0.000 claims description 36
- 235000006708 antioxidants Nutrition 0.000 claims description 36
- 230000001882 diuretic effect Effects 0.000 claims description 36
- 229960003712 propranolol Drugs 0.000 claims description 36
- 230000003078 antioxidant effect Effects 0.000 claims description 34
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims description 34
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 claims description 33
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 claims description 33
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 32
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 26
- 208000028867 ischemia Diseases 0.000 claims description 26
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
- 229940124549 vasodilator Drugs 0.000 claims description 25
- 239000003071 vasodilator agent Substances 0.000 claims description 25
- 125000003107 substituted aryl group Chemical group 0.000 claims description 23
- 206010020772 Hypertension Diseases 0.000 claims description 21
- 206010019280 Heart failures Diseases 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 18
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims description 17
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 16
- 108010061435 Enalapril Proteins 0.000 claims description 15
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 15
- 229960004166 diltiazem Drugs 0.000 claims description 15
- 229960000873 enalapril Drugs 0.000 claims description 15
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims description 15
- 239000002083 C09CA01 - Losartan Substances 0.000 claims description 14
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims description 14
- 206010063837 Reperfusion injury Diseases 0.000 claims description 14
- 229940030606 diuretics Drugs 0.000 claims description 14
- 229960001195 imidapril Drugs 0.000 claims description 14
- KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 claims description 14
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical group CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims description 14
- 229960004773 losartan Drugs 0.000 claims description 14
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 14
- 229960001597 nifedipine Drugs 0.000 claims description 14
- 229960004699 valsartan Drugs 0.000 claims description 14
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 13
- 239000002552 dosage form Substances 0.000 claims description 13
- 208000010125 myocardial infarction Diseases 0.000 claims description 13
- 208000031225 myocardial ischemia Diseases 0.000 claims description 13
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical group C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 claims description 12
- 230000006793 arrhythmia Effects 0.000 claims description 12
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims description 11
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims description 11
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 claims description 11
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 11
- 229960003580 felodipine Drugs 0.000 claims description 11
- 229960005170 moexipril Drugs 0.000 claims description 11
- 229960001783 nicardipine Drugs 0.000 claims description 11
- 229960000715 nimodipine Drugs 0.000 claims description 11
- 229960003401 ramipril Drugs 0.000 claims description 11
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims description 11
- 229960002909 spirapril Drugs 0.000 claims description 11
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 claims description 11
- 108700035424 spirapril Proteins 0.000 claims description 11
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 claims description 10
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 10
- 206010020880 Hypertrophy Diseases 0.000 claims description 10
- 229940127218 antiplatelet drug Drugs 0.000 claims description 10
- 206010003119 arrhythmia Diseases 0.000 claims description 10
- 229960002897 heparin Drugs 0.000 claims description 10
- 229920000669 heparin Polymers 0.000 claims description 10
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 10
- 229960001455 quinapril Drugs 0.000 claims description 10
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 claims description 10
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims description 9
- 229960002576 amiloride Drugs 0.000 claims description 9
- UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 claims description 9
- 229960003665 bepridil Drugs 0.000 claims description 9
- 229940074654 diuril Drugs 0.000 claims description 9
- 229960002490 fosinopril Drugs 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 235000021317 phosphate Nutrition 0.000 claims description 9
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims description 8
- 108010007859 Lisinopril Proteins 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 8
- 229960003883 furosemide Drugs 0.000 claims description 8
- 229960001632 labetalol Drugs 0.000 claims description 8
- 229960002394 lisinopril Drugs 0.000 claims description 8
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical group N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 8
- 229960001289 prazosin Drugs 0.000 claims description 8
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical group CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims description 7
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 7
- 229960002274 atenolol Drugs 0.000 claims description 7
- 229960004605 timolol Drugs 0.000 claims description 7
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000006 Nitroglycerin Substances 0.000 claims description 6
- 229960003711 glyceryl trinitrate Drugs 0.000 claims description 6
- 229960002474 hydralazine Drugs 0.000 claims description 6
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 claims description 6
- 229960000201 isosorbide dinitrate Drugs 0.000 claims description 6
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 6
- 229960002237 metoprolol Drugs 0.000 claims description 6
- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 4
- 102000005962 receptors Human genes 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 2
- 229930003268 Vitamin C Natural products 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002515 isoflavone derivatives Chemical class 0.000 claims description 2
- 235000008696 isoflavones Nutrition 0.000 claims description 2
- 235000019154 vitamin C Nutrition 0.000 claims description 2
- 239000011718 vitamin C Substances 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229960000528 amlodipine Drugs 0.000 claims 10
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 10
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims 9
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 6
- 235000008160 pyridoxine Nutrition 0.000 claims 3
- 239000011677 pyridoxine Substances 0.000 claims 3
- 229940011671 vitamin b6 Drugs 0.000 claims 3
- 102000015427 Angiotensins Human genes 0.000 claims 2
- 108010064733 Angiotensins Proteins 0.000 claims 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 1
- MREOWKKCLXWFQY-UHFFFAOYSA-N Cc1ncc(CO)c(C=O)c1O.Cc1ncc(COP(O)(O)=O)c(C=O)c1O Chemical compound Cc1ncc(CO)c(C=O)c1O.Cc1ncc(COP(O)(O)=O)c(C=O)c1O MREOWKKCLXWFQY-UHFFFAOYSA-N 0.000 claims 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 238000011552 rat model Methods 0.000 description 28
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
- 241000700159 Rattus Species 0.000 description 26
- 230000002861 ventricular Effects 0.000 description 25
- 230000036722 left ventricular developed pressure Effects 0.000 description 23
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 238000011084 recovery Methods 0.000 description 20
- 230000035488 systolic blood pressure Effects 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 210000004351 coronary vessel Anatomy 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229930006000 Sucrose Natural products 0.000 description 13
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 13
- 230000010410 reperfusion Effects 0.000 description 13
- 239000005720 sucrose Substances 0.000 description 13
- 229940079593 drug Drugs 0.000 description 11
- 231100000241 scar Toxicity 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- 230000009286 beneficial effect Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 210000000056 organ Anatomy 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000035487 diastolic blood pressure Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000008602 contraction Effects 0.000 description 7
- 238000001356 surgical procedure Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 6
- 230000037213 diet Effects 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 210000004165 myocardium Anatomy 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 208000001778 Coronary Occlusion Diseases 0.000 description 5
- 206010011086 Coronary artery occlusion Diseases 0.000 description 5
- FVWDBVACVTXVJN-UHFFFAOYSA-L dipotassium;propan-2-one;carbonate Chemical compound [K+].[K+].CC(C)=O.[O-]C([O-])=O FVWDBVACVTXVJN-UHFFFAOYSA-L 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- FCHXJFJNDJXENQ-UHFFFAOYSA-N pyridoxal hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(C=O)=C1O FCHXJFJNDJXENQ-UHFFFAOYSA-N 0.000 description 5
- 229960001327 pyridoxal phosphate Drugs 0.000 description 5
- 125000005425 toluyl group Chemical group 0.000 description 5
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 5
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 4
- WBUUALONSKFMFD-UHFFFAOYSA-N 6-methyl-1-morpholin-4-yl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C12=C(O)C(C)=NC=C2COC1N1CCOCC1 WBUUALONSKFMFD-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 206010000891 acute myocardial infarction Diseases 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001266 acyl halides Chemical class 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000008828 contractile function Effects 0.000 description 4
- 230000035876 healing Effects 0.000 description 4
- 230000000004 hemodynamic effect Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- 230000000302 ischemic effect Effects 0.000 description 4
- 210000005240 left ventricle Anatomy 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 3
- 206010058156 Reperfusion arrhythmia Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 230000036770 blood supply Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000036543 hypotension Effects 0.000 description 3
- GPSDUZXPYCFOSQ-UHFFFAOYSA-M m-toluate Chemical compound CC1=CC=CC(C([O-])=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-M 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 2
- 101800000734 Angiotensin-1 Proteins 0.000 description 2
- 102400000344 Angiotensin-1 Human genes 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 206010030124 Oedema peripheral Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000002651 drug therapy Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 2
- 229960001600 xylazine Drugs 0.000 description 2
- YWRWXPROHROKLY-UHFFFAOYSA-N (6-methyl-1-morpholin-4-yl-1,3-dihydrofuro[3,4-c]pyridin-7-yl) carbamate Chemical compound C12=C(OC(N)=O)C(C)=NC=C2COC1N1CCOCC1 YWRWXPROHROKLY-UHFFFAOYSA-N 0.000 description 1
- MKGQNFIKWWYCAM-UHFFFAOYSA-N (6-methyl-1-morpholin-4-yl-1,3-dihydrofuro[3,4-c]pyridin-7-yl) n,n-dimethylcarbamate Chemical compound O1CC2=CN=C(C)C(OC(=O)N(C)C)=C2C1N1CCOCC1 MKGQNFIKWWYCAM-UHFFFAOYSA-N 0.000 description 1
- YXYWLQVGOLMVSJ-UHFFFAOYSA-N 1-amino-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical group CC1=NC=C2COC(N)C2=C1O YXYWLQVGOLMVSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- ONXPDKGXOOORHB-BYPYZUCNSA-N N(5)-methyl-L-glutamine Chemical compound CNC(=O)CC[C@H](N)C(O)=O ONXPDKGXOOORHB-BYPYZUCNSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 206010047295 Ventricular hypertrophy Diseases 0.000 description 1
- 206010048010 Withdrawal syndrome Diseases 0.000 description 1
- HVTMFBOSQNXQPI-UHFFFAOYSA-N [4-formyl-5-(hydroxymethyl)pyridin-2-yl] 2,3-dimethylbenzoate Chemical compound CC1=CC=CC(C(=O)OC=2N=CC(CO)=C(C=O)C=2)=C1C HVTMFBOSQNXQPI-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I 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](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)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 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 230000037020 contractile activity Effects 0.000 description 1
- 230000009091 contractile dysfunction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 230000005986 heart dysfunction Effects 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 230000008065 myocardial cell damage Effects 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000004963 pathophysiological condition Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000001474 proteinuria Diseases 0.000 description 1
- 208000005333 pulmonary edema Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4415—Pyridoxine, i.e. Vitamin B6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15041599P | 1999-08-24 | 1999-08-24 | |
| US60/150415 | 1999-08-24 | ||
| PCT/CA2000/001020 WO2001013900A2 (en) | 1999-08-24 | 2000-08-24 | Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6814400A AU6814400A (en) | 2001-03-19 |
| AU783855B2 true AU783855B2 (en) | 2005-12-15 |
Family
ID=22534418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU68144/00A Ceased AU783855B2 (en) | 1999-08-24 | 2000-08-24 | Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (7) | US6677356B1 (enExample) |
| EP (2) | EP1872797A3 (enExample) |
| JP (1) | JP2003507418A (enExample) |
| AU (1) | AU783855B2 (enExample) |
| CA (1) | CA2383252A1 (enExample) |
| WO (1) | WO2001013900A2 (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1169322E (pt) * | 1999-03-08 | 2007-04-30 | Medicure Inc | Análogos de piridoxal para o tratamento de desordens causadas por uma deficiência em vitamina b-6. |
| EP1196171A2 (en) * | 1999-07-13 | 2002-04-17 | Medicure Inc. | Use of pyridoxin derivatives for the treatment of diabetes and related complications |
| US7442689B2 (en) | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| EP1278526A2 (en) * | 2000-03-28 | 2003-01-29 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US20040121988A1 (en) * | 2001-03-28 | 2004-06-24 | Medicure International Inc. | Treatment of cerebrovascular disease |
| NO20024880L (no) * | 2002-03-19 | 2003-09-22 | Per Hamre | Sammensetning inneholdende fosfat |
| US20040186077A1 (en) * | 2003-03-17 | 2004-09-23 | Medicure International Inc. | Novel heteroaryl phosphonates as cardioprotective agents |
| AU2004224566A1 (en) * | 2003-03-27 | 2004-10-07 | Medicure Inc. | Compositions for treating angina |
| AU2004224562A1 (en) * | 2003-03-27 | 2004-10-07 | Medicure Inc. | Modulation of cell death |
| US7169805B2 (en) * | 2003-05-28 | 2007-01-30 | Nicox S.A. | Captopril derivatives |
| EP1643999B8 (en) | 2003-06-20 | 2012-03-14 | NephroGenex, Inc. | Pyridoxamine for use in the treatment of diabetic nephropathy in type ii diabetes |
| WO2005089639A2 (en) * | 2004-03-16 | 2005-09-29 | Talarico M D Matthew T | Method for vascular dysregulation |
| ES2282062T1 (es) | 2004-06-04 | 2007-10-16 | Teva Pharmaceutical Industries Ltd. | Composicion farmaceutica que contiene irbesartan. |
| US20060019929A1 (en) * | 2004-07-07 | 2006-01-26 | Albert Friesen | Combination therapies employing platelet aggregation drugs |
| WO2006005173A1 (en) * | 2004-07-09 | 2006-01-19 | Medicure International Inc. | Combination therapies employing nicotinic acid derivatives or fibric acid derivatives |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US20060035864A1 (en) * | 2004-08-10 | 2006-02-16 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| EP1787647B1 (en) * | 2004-09-06 | 2012-06-20 | Kowa Company, Ltd. | Remedy for glomerular diseases |
| AU2005309352A1 (en) * | 2004-09-24 | 2006-06-01 | Medicure International Inc. | Pyridoxal-5-phosphate and stent for the treatment and prevention of atherosclerosis and restenosis |
| CA2580970A1 (en) * | 2004-09-24 | 2006-06-08 | Medicure International Inc. | Pyridoxal-5´-phosphate and related compounds in combination with therapeutic cardiovascular compounds for treating angina. |
| EP1817288A4 (en) * | 2004-10-28 | 2009-08-26 | Medicure Int Inc | DUAL ANTIPLÄTTCHEN / ANTIKOAGULANS PYRIDOXINANALOGE |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| AU2005309297A1 (en) * | 2004-11-26 | 2006-06-01 | Medicure International Inc. | Novel formulation of pyridoxal 5'-phosphate and method of preparation |
| CA2589200A1 (en) * | 2004-11-26 | 2006-06-01 | Medicure International Inc. | Formulations of pyridoxal -5'-phosphate and methods of preparation |
| US20060128797A1 (en) * | 2004-12-15 | 2006-06-15 | Yanming Wang | Method and composition for resuscitation |
| JP2008526783A (ja) * | 2005-01-05 | 2008-07-24 | メディキュア・インターナショナル・インコーポレーテッド | トリグリセリドレベルを調節するための化合物及び方法 |
| CA2503087A1 (en) * | 2005-03-30 | 2006-09-30 | Medicure International Inc. | Intravenous formulations of pyridoxal 5'-phosphate and method of preparation |
| SE529780C2 (sv) * | 2005-08-04 | 2007-11-20 | Hexagon Metrology Ab | Mätförfarande och mätanordning för användning i mätsystem såsom koordinatmätmaskiner |
| US8158146B2 (en) | 2005-09-28 | 2012-04-17 | Teva Pharmaceutical Industries Ltd. | Stable combinations of amlodipine besylate and benazepril hydrochloride |
| JP2009517411A (ja) * | 2005-11-28 | 2009-04-30 | メディキュア インターナショナル インコーポレーテッド | 心血管及び関連病状の処置のための調剤 |
| EP1790331A1 (en) * | 2005-11-28 | 2007-05-30 | Medicure International Inc. | Use of pyridoxal-5-phosphate for the treatment of cardiovascular and related pathologies |
| DK2848938T3 (da) | 2006-04-24 | 2017-11-13 | Critical Care Diagnostics Inc | Evaluering af effektiviteten af en behandling hos et individ baseret på st2- niveauer |
| US20070249562A1 (en) * | 2006-04-25 | 2007-10-25 | Friesen Albert D | Treatment of atrial fibrillation |
| EP2049127B1 (en) * | 2006-05-23 | 2014-11-26 | University of Connecticut | N-methanocarba derivatives to treat cardiac diseases |
| US20110123612A1 (en) * | 2008-04-10 | 2011-05-26 | Sung Wuk Kim | Pharmaceutical preparation containing non-dihydropyridine calcium channel blocker and angiotensin-2 receptor blocker |
| HUE029880T2 (en) | 2008-04-18 | 2017-04-28 | Critical Care Diagnostics Inc | Predicting the risk of serious heart events |
| UA102721C2 (uk) * | 2009-01-23 | 2013-08-12 | Ханми Сайенс Ко., Лтд. | Тверда фармацевтична композиція, яка містить амлодипін і лозартан, і спосіб її отримання |
| CN102985432B (zh) | 2010-02-22 | 2016-11-02 | 康涅狄格大学 | 用于治疗心脏病的amp衍生物 |
| US20160310524A1 (en) * | 2013-12-13 | 2016-10-27 | Ralph Ankenman | Compositions and methods for treating dysregulated systems |
| WO2016046674A1 (en) * | 2014-09-28 | 2016-03-31 | Mohan M Alapati | Compositions and methods for the treatment of moderate to severe pain |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| CN107418989A (zh) * | 2017-08-21 | 2017-12-01 | 浙江工业大学 | 一种脂肪酶催化在线合成n‑(5‑蔗糖酯戊酰基)美托洛尔的方法 |
| CN108508218A (zh) * | 2018-07-09 | 2018-09-07 | 复旦大学附属中山医院 | 晚期糖基化终产物cml作为心肌缺血再灌注损伤的早期诊断标志物及其应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2641189A1 (fr) * | 1988-06-20 | 1990-07-06 | Timol Mamoojee | Compositions pharmaceutiques contenant de l'acide acetyl salicylique et de la vitamine b6 |
| US5254572A (en) * | 1987-11-27 | 1993-10-19 | Vesta Medicines (Pty) Ltd. | Method and composition for supplementing vitamin B6 where the PN-PLP pathway is disturbed |
| WO1998019690A1 (en) * | 1996-11-06 | 1998-05-14 | Bristol-Myers Squibb Company | Method for treating alzheimer's disease |
Family Cites Families (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206463A (en) | 1965-09-14 | Pyridoxine aspartate and its process of preparation | ||
| FR846376A (fr) | 1938-08-23 | 1939-09-15 | Appareillage de navigation aérienne et de bombardement aérien | |
| DE863754C (de) | 1951-04-17 | 1953-01-19 | Gottfried Korbmacher | Bodenbremse mit zwischen Rad und Fahrbahn einschiebbaren Bremsschuhen an Kraftfahrzeugen |
| US2904551A (en) * | 1956-11-14 | 1959-09-15 | Merck & Co Inc | Chemical compounds and processes of preparing the same |
| US3282778A (en) * | 1960-09-02 | 1966-11-01 | Lohel Mervyn Joseph | Medicinal preparation containing acetyl salicylic acid and a pyridoxine compound |
| GB966805A (en) | 1961-05-15 | 1964-08-19 | Merck & Co Inc | Process for the preparation of 2-methyl-3-hydroxypyridines |
| NL280553A (enExample) | 1962-07-05 | |||
| FR5552M (enExample) | 1966-04-28 | 1967-11-20 | ||
| FR5801M (enExample) | 1966-06-27 | 1968-02-19 | ||
| GB1228142A (enExample) | 1967-03-31 | 1971-04-15 | ||
| FR6453M (enExample) | 1967-06-13 | 1968-11-12 | ||
| JPS4821959Y1 (enExample) | 1967-09-04 | 1973-06-26 | ||
| DE1767499A1 (de) | 1968-05-16 | 1971-09-09 | Merck Patent Gmbh | Verfahren zur Herstellung haltbarer Vitaminzubereitungen |
| ES360566A1 (es) | 1968-11-22 | 1970-10-16 | Made Labor Sa | Un metodo de obtencion de alfa-cetoglutarato de piridoxina y sus derivados. |
| GB1236531A (en) | 1969-02-12 | 1971-06-23 | Soc D Etudes Prod Chimique | Adenin derivative |
| JPS4821959B1 (enExample) | 1969-03-31 | 1973-07-02 | ||
| US3910921A (en) | 1970-01-08 | 1975-10-07 | Soc D Etudes Prod Chimique | Papaverine monopyridoxal phosphate |
| GB1297080A (enExample) | 1970-04-17 | 1972-11-22 | ||
| FR2101010A1 (en) | 1970-08-06 | 1972-03-31 | Lyocentre | Sparteine mono-and dipyridoxinates and prepn - as tonics for cardiova disorders |
| JPS5417130B2 (enExample) | 1971-12-21 | 1979-06-27 | ||
| GB1493993A (en) | 1975-05-16 | 1977-12-07 | Howard A | Dietary supplement and dietary methods employing said supplement for the treatment of obesity |
| US4053607A (en) | 1972-04-04 | 1977-10-11 | Beecham Group Limited | Aryloxypyridine for treating hyperglycaemia |
| US4036844A (en) | 1972-04-04 | 1977-07-19 | Beecham Group Limited | Aryloxypyridines |
| GB1360536A (en) | 1972-04-25 | 1974-07-17 | Soc D Etudes Prod Chimique | Pyridoxyl-l-aspartic acid salt |
| BE790118A (fr) | 1972-10-09 | 1973-02-01 | Made Labor Sa | Derives de l'alpha-cetoglutarate de pyridoxal et de pyridoxamine, |
| US4032534A (en) | 1973-03-22 | 1977-06-28 | Ferlus-Chimie S.A. | Certain 2-(2-thioethyl)thiazolidine-4-carboxylic acids |
| FR2255883A1 (en) | 1973-12-28 | 1975-07-25 | Centre Etd Ind Pharma | Clofibric acid-vitamin B6 compsns. - with synergistic hypocholesterolaemic and normolipaemic activity |
| FR2275209A1 (fr) | 1974-06-21 | 1976-01-16 | Synthelabo | Nouveaux esters cetoniques, leurs sels, leur preparation et les medicaments qui les renferment |
| FR2276048A1 (fr) | 1974-06-27 | 1976-01-23 | Synthelabo | Nouveaux esters du cyclohexanol, leurs sels, leur preparation et les medicaments qui les renferment |
| DE2461742C2 (de) | 1974-12-28 | 1983-01-27 | Steigerwald Arzneimittelwerk Gmbh, 6100 Darmstadt | Pyridoxin-5'-phosphorsäureester-Derivate sowie deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPS5417130Y2 (enExample) | 1975-01-29 | 1979-07-03 | ||
| GB1525885A (en) | 1976-05-11 | 1978-09-20 | Soc D Etudes Prod Chimique | Vincamine salt of pyridoxal phosphate |
| JPS5417130A (en) | 1977-07-08 | 1979-02-08 | Chugai Pharmaceut Co Ltd | Remedy for cardio-vasocular diseases |
| BE863754A (fr) | 1978-02-08 | 1978-05-29 | Dechamps Pierre | Nouveaux derives de la vincamine utilisables comme regulateurs de la circulation cerebrale |
| FR2428640A1 (fr) | 1978-06-12 | 1980-01-11 | Parcor | Derives de pyridoxine, leur procede de preparation et leur application therapeutique |
| US4167562A (en) | 1978-08-28 | 1979-09-11 | Evers H Ray | Method and composition for treating arteriosclerosis |
| DE2845484A1 (de) * | 1978-10-19 | 1980-04-30 | Groening Ruediger | Verfahren zur erhoehung der biologischen verfuegbarkeit von arzneistoffen |
| IL62602A (en) | 1980-05-19 | 1984-06-29 | Labaz Sanofi Nv | Pyridoxine derivatives,their preparation and pharmaceutical compositions containing them |
| GB2075983B (en) * | 1980-05-19 | 1984-05-10 | Labaz Nv | Pyridoxine derivatives process for preparing them and use in therapeutics |
| US4753956A (en) * | 1981-01-02 | 1988-06-28 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| IT1141070B (it) | 1980-09-22 | 1986-10-01 | Luso Farmaco Inst | Impiego dell'alfa-chetoglutarato di piridossina nella profilassi della iperlattacidemia |
| CA1184499A (en) | 1981-06-29 | 1985-03-26 | David C. Madsen | Nutritional composition for management of hepatic failure |
| US4369172A (en) | 1981-12-18 | 1983-01-18 | Forest Laboratories Inc. | Prolonged release therapeutic compositions based on hydroxypropylmethylcellulose |
| US4528197A (en) | 1983-01-26 | 1985-07-09 | Kabivitrum Ab | Controlled triglyceride nutrition for hypercatabolic mammals |
| IN160104B (enExample) | 1983-04-05 | 1987-06-27 | Scras | |
| US4735950A (en) | 1983-04-05 | 1988-04-05 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S) | Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same |
| US4515771A (en) | 1983-04-11 | 1985-05-07 | Fine Daniel H | Composition and method for the preventative treatment of dental disease and apparatus for dispensing said composition |
| GB8330517D0 (en) | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330658D0 (en) | 1983-11-17 | 1983-12-29 | Scras | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
| IT1212792B (it) | 1983-11-30 | 1989-11-30 | Egidio Aldo Moja | Supplemento dietetico e alimento preconfezionato che lo contiene procedimento di preparazione e metodo di somministrazione |
| US5272165A (en) | 1984-03-19 | 1993-12-21 | The Rockefeller University | 2-alkylidene-aminoguanidines and methods of use therefor |
| US5130324A (en) | 1984-03-19 | 1992-07-14 | The Rockefeller University | 2-alkylidene-aminoguanidines and methods of use therefor |
| US5288498A (en) * | 1985-05-01 | 1994-02-22 | University Of Utah Research Foundation | Compositions of oral nondissolvable matrixes for transmucosal administration of medicaments |
| US4567179A (en) | 1984-10-11 | 1986-01-28 | Pfizer, Inc. | Antiinflammatory salts of piroxicam |
| DE3519693A1 (de) | 1985-06-01 | 1987-01-02 | Basf Ag | Pyridin-derivate, ihre herstellung und verwendung |
| US4837239A (en) | 1985-08-23 | 1989-06-06 | Syntex (U.S.A.) Inc. | Cardiotonic phosphodiesterase inhibitors complexed with water soluble vitamins |
| US5053396A (en) | 1985-08-27 | 1991-10-01 | Blass David H | Therapeutic composition |
| US4735956A (en) | 1985-09-13 | 1988-04-05 | Merck & Co., Inc. | Certain 1,4-dihydro-2,6-di-lower hydrocarbyl-4-heterocyclic-3,5-pyridine dicarboxylates which are useful as calcium channel blockers |
| US4605741A (en) | 1985-11-13 | 1986-08-12 | Lisapharma Spa | Pharmaceutically active salt derivative of 3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde phosphate |
| DE3634016A1 (de) | 1986-04-17 | 1987-10-29 | Lohmann Gmbh & Co Kg | Flaechenfoermiges therapeutisches system, verfahren zu seiner herstellung und seine verwendung |
| US5210083A (en) | 1986-07-17 | 1993-05-11 | Ed. Geistlich Sohne A.G. Fur Chemische Industrie | Pharmaceutical compositions |
| US5563126A (en) | 1986-11-20 | 1996-10-08 | Metabolite Laboratories | Method for treatment and prevention of deficiencies of vitamins B12, folic acid, and B6 |
| NZ222664A (en) | 1986-11-29 | 1990-06-26 | Vesta Med Pty Ltd | Pharmaceutical compositions containing pyridoxal as a source of vitamin b6 |
| US5631271A (en) | 1986-11-29 | 1997-05-20 | Serfontein; Willem J. | Methods and preparations for the treatment and prophylaxis of metabolic disturbances |
| US4843071A (en) | 1986-12-05 | 1989-06-27 | Serotonin Industries Of Charleston | Method and composition for treating obesity, drug abuse, and narcolepsy |
| US5385938B1 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Method of using glycolic acid for treating wrinkles |
| US5288716A (en) | 1987-02-18 | 1994-02-22 | Ulrich Speck | Use of pyridoxine derivatives in the prevention and treatment of hyperlipidaemia and atherosclerosis |
| DE3705549A1 (de) | 1987-02-18 | 1988-09-01 | Ulrich Speck | Verwendung von pyridoxin-derivaten bei der prophylaxe und therapie von hyperlipidaemien und atherosklerose |
| SE8701662L (sv) | 1987-04-22 | 1988-10-23 | Gelder Nico M Van | Saett och medel foer att behandla neurologiska sjukdomar, exempelvis migraen genom paaverkan av nervcellerna |
| US5213813A (en) | 1987-05-29 | 1993-05-25 | The University Of Vermont | Pyridoxal-5'-phosphate as an in vitro blood platelet stabilizer |
| EP0326034B1 (de) | 1988-01-28 | 1992-08-26 | Peter Dr. Költringer | Kombinationspräparat zur Behandlung von Nervenzell-und Nervenfasererkrankungen und Verletzungen |
| NZ228285A (en) | 1988-03-11 | 1991-08-27 | Teikoku Seiyaku Kk | Pharmaceutical composition comprising a polypeptide and adapted for intravaginal administration |
| US5254557A (en) | 1988-05-09 | 1993-10-19 | Beecham Group P.L.C. | Compound and treatment |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5001115A (en) | 1989-05-17 | 1991-03-19 | University Of Florida | Prodrugs of biologically active hydroxyaromatic compounds |
| GB8918368D0 (en) | 1989-08-11 | 1989-09-20 | Amco Chemie Gmbh | Compositions for treating obstructive airways disease |
| US5527527A (en) * | 1989-09-07 | 1996-06-18 | Alkermes, Inc. | Transferrin receptor specific antibody-neuropharmaceutical agent conjugates |
| DE4016963A1 (de) | 1990-05-25 | 1991-11-28 | Steigerwald Arzneimittelwerk | Verwendung von magnesium-pyridoxal-5'-phosphat-glutaminat zur verhinderung von erkrankungen, die sich infolge von gefaessschaeden ergeben |
| US5668117A (en) * | 1991-02-22 | 1997-09-16 | Shapiro; Howard K. | Methods of treating neurological diseases and etiologically related symptomology using carbonyl trapping agents in combination with previously known medicaments |
| US5385937A (en) | 1991-04-10 | 1995-01-31 | Brigham & Women's Hospital | Nitrosation of homocysteine as a method for treating homocysteinemia |
| GB2254556B (en) | 1991-04-11 | 1995-04-12 | Fisons Plc | Formulations containing linolenic acid |
| IL101879A (en) | 1991-05-15 | 1998-06-15 | Univ Yale | Preparation of preparations of pre-pharmacological compounds that can be used for metabolism in the liver for the treatment of liver-related diseases |
| FR2678622B1 (fr) | 1991-07-03 | 1994-11-18 | Adir | Nouveaux complexes de vanadium, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| WO1993013660A1 (en) | 1992-01-06 | 1993-07-22 | Health Maintenance Programs, Inc. | Pharmaceutically active antioxydant containing composition and the method of its use to prevent and treat restenosis following angioplasty |
| EP0555681A1 (en) * | 1992-02-13 | 1993-08-18 | E.R. SQUIBB & SONS, INC. | Use of a combination of potassium channel activators and sulfhydryl containing compounds for the manufacture of a medicament for the treatment of ischemia and myocarolial infarct |
| JP3623502B2 (ja) | 1992-06-12 | 2005-02-23 | セファロン，インコーポレイテッド | 末梢神経障害の予防および治療 |
| US5420112A (en) | 1992-06-12 | 1995-05-30 | Lewis; Michael E. | Prevention and treatment of peripheral neuropathy |
| US5330743A (en) | 1992-11-12 | 1994-07-19 | Magnetic Research, Inc. | Aminosaccharide contrast agents for magnetic resonance images |
| JPH06172220A (ja) * | 1992-12-03 | 1994-06-21 | Upjohn Co:The | 虚血性疾患治療用医薬組成物 |
| US5795873A (en) | 1992-12-29 | 1998-08-18 | Metabolite Laboratories, Inc. | Method for treatment and prevention of deficiencies of vitamins B12, folic acid and B6 |
| IT1263957B (it) | 1993-02-23 | 1996-09-05 | Impiego terapeutico del pirrolidon carbossilato di piridossina | |
| TW268948B (enExample) | 1993-04-02 | 1996-01-21 | Senju Pharma Co | |
| US5443643A (en) * | 1993-04-21 | 1995-08-22 | Axis Usa, Inc. | Heatless resin coating system |
| US20040180865A1 (en) | 1993-06-04 | 2004-09-16 | Jeffry W. Kreamer | Aspirin and vitamin and/or trace element compositions for the amelioration and treatment of vascular disease |
| JPH0817174B2 (ja) * | 1993-11-10 | 1996-02-21 | キヤノン販売株式会社 | 絶縁膜の改質方法 |
| DE4344751A1 (de) | 1993-12-28 | 1995-06-29 | Carl Heinrich Dr Weischer | Neue Vitamin B6-Derivate und deren Herstellung und Verwendung als Arzneimittel und als Kosmetika |
| US5504090A (en) | 1994-03-30 | 1996-04-02 | Trustees Of The University Of Pennsylvania | Compositions and methods for the prevention and treatment of ischemia-reperfusion organ injury |
| JP2757775B2 (ja) | 1994-05-23 | 1998-05-25 | 日本電気株式会社 | システム時計整合方式およびシステム時計整合機能付電話交換網 |
| DE4440875A1 (de) * | 1994-11-16 | 1996-06-05 | Santrade Ltd | Vorrichtung zur Herstellung von Pastillen |
| EP0799051B1 (en) | 1994-12-12 | 2005-07-27 | Omeros Corporation | Irrigation solution and use thereof for perioperatively inhibiting pain, inflammation and spasm at a wound |
| US5569459A (en) | 1995-02-15 | 1996-10-29 | Bio-Virus Research Incorporated | Pharmaceutical compositions for the management of premenstrual syndrome and alleviation of menopausal disorders |
| US5733916A (en) | 1995-03-24 | 1998-03-31 | The Trustees Of The University Of Pennsylvania | Prevention and treatment of ischemia-reperfusion and endotoxin-related injury using adenosine and purino receptor antagonists |
| US5610115A (en) * | 1995-07-20 | 1997-03-11 | Samsung General Chemicals Co., Ltd. | Organic carrier supported metallocene catalyst for olefin polymerization |
| US5874443A (en) | 1995-10-19 | 1999-02-23 | Trega Biosciences, Inc. | Isoquinoline derivatives and isoquinoline combinatorial libraries |
| US5833998A (en) | 1995-11-06 | 1998-11-10 | The Procter & Gamble Company | Topical compositions for regulating the oily/shiny appearance of skin |
| US5733884A (en) | 1995-11-07 | 1998-03-31 | Nestec Ltd. | Enteral formulation designed for optimized wound healing |
| US5663726A (en) * | 1995-12-01 | 1997-09-02 | U.S. Philips Corporation | High speed variable-length decoder arrangement with reduced memory requirements for tag stream buffering |
| US5874420A (en) | 1995-12-26 | 1999-02-23 | Allegheny University Of The Health Sciences | Process for regulating vagal tone |
| US5847008A (en) | 1996-02-02 | 1998-12-08 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
| US5859051A (en) | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
| US5834446A (en) | 1996-06-21 | 1998-11-10 | Queen's University At Kingston | Nerve process growth modulators |
| GB9613470D0 (en) * | 1996-06-27 | 1996-08-28 | Ciba Geigy Ag | Small solid oral dosage form |
| US5770215A (en) | 1997-01-06 | 1998-06-23 | Moshyedi; Emil Payman | Multivitamin/vascular occlusion inhibiting composition |
| US5804594A (en) | 1997-01-22 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for improving wrinkles and other skin conditions |
| US5888514A (en) | 1997-05-23 | 1999-03-30 | Weisman; Bernard | Natural composition for treating bone or joint inflammation |
| EP0891719A1 (en) | 1997-07-14 | 1999-01-20 | N.V. Nutricia | Nutritional composition containing methionine |
| US6610480B1 (en) | 1997-11-10 | 2003-08-26 | Genentech, Inc. | Treatment and diagnosis of cardiac hypertrophy |
| US6051587A (en) * | 1998-04-16 | 2000-04-18 | Medicure, Inc. | Treatment of iatrogenic and age-related hypertension and pharmaceutical compositions useful therein |
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| US5904090A (en) * | 1998-10-01 | 1999-05-18 | Dart Industries Inc. | Basket and drive arrangement for salad spinner |
| PT1169322E (pt) * | 1999-03-08 | 2007-04-30 | Medicure Inc | Análogos de piridoxal para o tratamento de desordens causadas por uma deficiência em vitamina b-6. |
| WO2001064692A1 (en) * | 2000-02-29 | 2001-09-07 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| CA2414188A1 (en) * | 2000-07-07 | 2002-01-17 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: cardiovascular therapeutics |
| AU2002218002A1 (en) | 2000-11-02 | 2002-05-15 | University Of South Carolina | Use of pyridoxamine for the treatment and inhibition of obesity-related complications |
-
2000
- 2000-08-24 AU AU68144/00A patent/AU783855B2/en not_active Ceased
- 2000-08-24 US US09/645,237 patent/US6677356B1/en not_active Expired - Fee Related
- 2000-08-24 EP EP07017513A patent/EP1872797A3/en not_active Withdrawn
- 2000-08-24 WO PCT/CA2000/001020 patent/WO2001013900A2/en not_active Ceased
- 2000-08-24 EP EP00956009A patent/EP1210117A2/en not_active Withdrawn
- 2000-08-24 JP JP2001518038A patent/JP2003507418A/ja active Pending
- 2000-08-24 CA CA002383252A patent/CA2383252A1/en not_active Abandoned
-
2003
- 2003-08-12 US US10/639,950 patent/US7115625B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,955 patent/US7115626B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,949 patent/US7125889B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,876 patent/US7132430B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,877 patent/US7144892B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,948 patent/US7148233B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5254572A (en) * | 1987-11-27 | 1993-10-19 | Vesta Medicines (Pty) Ltd. | Method and composition for supplementing vitamin B6 where the PN-PLP pathway is disturbed |
| FR2641189A1 (fr) * | 1988-06-20 | 1990-07-06 | Timol Mamoojee | Compositions pharmaceutiques contenant de l'acide acetyl salicylique et de la vitamine b6 |
| WO1998019690A1 (en) * | 1996-11-06 | 1998-05-14 | Bristol-Myers Squibb Company | Method for treating alzheimer's disease |
Also Published As
| Publication number | Publication date |
|---|---|
| US7125889B2 (en) | 2006-10-24 |
| US20040033993A1 (en) | 2004-02-19 |
| JP2003507418A (ja) | 2003-02-25 |
| US20040033991A1 (en) | 2004-02-19 |
| WO2001013900A2 (en) | 2001-03-01 |
| AU6814400A (en) | 2001-03-19 |
| EP1872797A2 (en) | 2008-01-02 |
| EP1210117A2 (en) | 2002-06-05 |
| US20040038945A1 (en) | 2004-02-26 |
| WO2001013900A3 (en) | 2002-02-07 |
| US7148233B2 (en) | 2006-12-12 |
| US6677356B1 (en) | 2004-01-13 |
| US7115626B2 (en) | 2006-10-03 |
| US20040033992A1 (en) | 2004-02-19 |
| US7132430B2 (en) | 2006-11-07 |
| US7144892B2 (en) | 2006-12-05 |
| EP1872797A3 (en) | 2008-04-02 |
| CA2383252A1 (en) | 2001-03-01 |
| US7115625B2 (en) | 2006-10-03 |
| US20040033990A1 (en) | 2004-02-19 |
| US20040033989A1 (en) | 2004-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU783855B2 (en) | Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds | |
| AU763464B2 (en) | Pyridoxal analogues for vitamin B-6 disorders | |
| ES2240419T3 (es) | Fosfonatos protectores del corazon. | |
| US6489345B1 (en) | Treatment of diabetes and related pathologies | |
| CN104619710B (zh) | 用于治疗再灌注损伤的氧杂二环庚烷和氧杂二环庚烯 | |
| WO2007121588A1 (en) | Treatment of atrial fibrillation | |
| AU2010219044B2 (en) | 1,4-benzothiazepine-1-oxide derivative and pharmaceutical composition utilizing the same | |
| CN109503548A (zh) | 一种丁苯酞衍生物及其制备方法和应用 | |
| CN106661060B (zh) | 菲罗啉膦酸类衍生物及其制备方法和应用 | |
| CN114349745B (zh) | 一种用于治疗心肌缺血的药物及其制备方法 | |
| CN112209834B (zh) | 一种有机亚硝酸根供体及其制备方法与医药用途 | |
| CN118724879B (zh) | 一种氘代稠环化合物及其制备方法与用途 | |
| EP1640005A2 (en) | Pyridoxal analogues for the treatment of disorders caused by a deficiency in vitamin B6 |