JP2014532885A5 - - Google Patents
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- JP2014532885A5 JP2014532885A5 JP2014540426A JP2014540426A JP2014532885A5 JP 2014532885 A5 JP2014532885 A5 JP 2014532885A5 JP 2014540426 A JP2014540426 A JP 2014540426A JP 2014540426 A JP2014540426 A JP 2014540426A JP 2014532885 A5 JP2014532885 A5 JP 2014532885A5
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- JP
- Japan
- Prior art keywords
- lipid
- cer
- compared
- control
- sample
- 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.)
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- 208000037998 chronic venous disease Diseases 0.000 claims description 142
- 150000002632 lipids Chemical class 0.000 claims description 109
- 239000000523 sample Substances 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 77
- 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 description 68
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 64
- 238000011282 treatment Methods 0.000 claims description 61
- ZJVVOYPTFQEGPH-UHFFFAOYSA-N 102917-80-6 Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC ZJVVOYPTFQEGPH-UHFFFAOYSA-N 0.000 claims description 60
- ZJVVOYPTFQEGPH-AUTSUKAISA-N N-tetracosanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC ZJVVOYPTFQEGPH-AUTSUKAISA-N 0.000 claims description 60
- 239000013068 control sample Substances 0.000 claims description 54
- MGOOTGNGBOPVIV-VVNLPLDBSA-N alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/16:0) Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 MGOOTGNGBOPVIV-VVNLPLDBSA-N 0.000 claims description 48
- 230000003247 decreasing effect Effects 0.000 claims description 48
- 235000012000 cholesterol Nutrition 0.000 claims description 34
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 30
- 229940079593 drug Drugs 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 29
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 27
- YDNKGFDKKRUKPY-TURZORIXSA-N N-hexadecanoylsphingosine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC YDNKGFDKKRUKPY-TURZORIXSA-N 0.000 claims description 27
- 108010033266 Lipoprotein(a) Proteins 0.000 claims description 24
- 102000057248 Lipoprotein(a) Human genes 0.000 claims description 24
- FZLJBZZCTNZGFA-ONMSRFGWSA-N alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 FZLJBZZCTNZGFA-ONMSRFGWSA-N 0.000 claims description 24
- VJLLLMIZEJJZTE-NNTBDIJYSA-N beta-D-glucosyl-N-hexadecanoylsphingosine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VJLLLMIZEJJZTE-NNTBDIJYSA-N 0.000 claims description 24
- 108010074051 C-Reactive Protein Proteins 0.000 claims description 18
- OAHFTKWSJGVMTG-MBIABJCFSA-N N-(9Z-hexadecenoyl)sphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCC OAHFTKWSJGVMTG-MBIABJCFSA-N 0.000 claims description 18
- 238000002560 therapeutic procedure Methods 0.000 claims description 18
- VODZWWMEJITOND-NXCSZAMKSA-N N-octadecanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC VODZWWMEJITOND-NXCSZAMKSA-N 0.000 claims description 17
- XWBWIAOWSABHFI-NUKVNZTCSA-N N-icosanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC XWBWIAOWSABHFI-NUKVNZTCSA-N 0.000 claims description 16
- 230000009469 supplementation Effects 0.000 claims description 16
- 102100032752 C-reactive protein Human genes 0.000 claims description 15
- 102000005666 Apolipoprotein A-I Human genes 0.000 claims description 12
- 108010059886 Apolipoprotein A-I Proteins 0.000 claims description 12
- 108010010234 HDL Lipoproteins Proteins 0.000 claims description 12
- 102000015779 HDL Lipoproteins Human genes 0.000 claims description 12
- YMQZQHIESOAPQH-JXGHDCMNSA-N N-heptadecanoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC YMQZQHIESOAPQH-JXGHDCMNSA-N 0.000 claims description 12
- RWKUXQNLWDTSLO-GWQJGLRPSA-N N-hexadecanoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC RWKUXQNLWDTSLO-GWQJGLRPSA-N 0.000 claims description 12
- QEDPUVGSSDPBMD-XTAIVQBESA-N N-lignoceroylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC QEDPUVGSSDPBMD-XTAIVQBESA-N 0.000 claims description 12
- KYICBZWZQPCUMO-PSALXKTOSA-N N-myristoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCC KYICBZWZQPCUMO-PSALXKTOSA-N 0.000 claims description 12
- KWGVNZWSEWAOMI-DHCJWVHISA-N alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0) Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 KWGVNZWSEWAOMI-DHCJWVHISA-N 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 101710095342 Apolipoprotein B Proteins 0.000 claims description 10
- 102100040202 Apolipoprotein B-100 Human genes 0.000 claims description 10
- 210000002966 serum Anatomy 0.000 claims description 10
- KEPQASGDXIEOIL-UHFFFAOYSA-N (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC KEPQASGDXIEOIL-UHFFFAOYSA-N 0.000 claims description 9
- KEPQASGDXIEOIL-GLQCRSEXSA-N N-docosanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC KEPQASGDXIEOIL-GLQCRSEXSA-N 0.000 claims description 9
- YMYQEDCYNANIPI-DYJXBSQNSA-N beta-D-glucosyl-N-octadecanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YMYQEDCYNANIPI-DYJXBSQNSA-N 0.000 claims description 9
- 102000030169 Apolipoprotein C-III Human genes 0.000 claims description 8
- 108010056301 Apolipoprotein C-III Proteins 0.000 claims description 8
- 108010023302 HDL Cholesterol Proteins 0.000 claims description 8
- 108010028554 LDL Cholesterol Proteins 0.000 claims description 8
- HLIJNIKSBCIDGO-QKLMXXKVSA-N beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-hexadecanoylsphingosine Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HLIJNIKSBCIDGO-QKLMXXKVSA-N 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 238000008214 LDL Cholesterol Methods 0.000 claims description 6
- LQINJRUGTUOHGS-YPDYIYJKSA-N N-pentadecanoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC LQINJRUGTUOHGS-YPDYIYJKSA-N 0.000 claims description 6
- QYWVASPEUXEHSY-NNRNTGNWSA-N beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-(docosanoyl)sphingosine Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QYWVASPEUXEHSY-NNRNTGNWSA-N 0.000 claims description 6
- POQRWMRXUOPCLD-GZXCKHLVSA-N beta-D-glucosyl-N-(tetracosanoyl)sphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O POQRWMRXUOPCLD-GZXCKHLVSA-N 0.000 claims description 6
- DFELABABMXOKTD-IYFIADHGSA-N beta-D-glucosyl-N-eicosanoylsphingosine Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DFELABABMXOKTD-IYFIADHGSA-N 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 claims description 4
- 102000018616 Apolipoproteins B Human genes 0.000 claims description 4
- 108010027006 Apolipoproteins B Proteins 0.000 claims description 4
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 4
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 4
- 102000004895 Lipoproteins Human genes 0.000 claims description 4
- 108090001030 Lipoproteins Proteins 0.000 claims description 4
- 108020004459 Small interfering RNA Proteins 0.000 claims description 4
- 229960003765 fluvastatin Drugs 0.000 claims description 4
- 238000004949 mass spectrometry Methods 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 210000002381 plasma Anatomy 0.000 claims description 4
- 230000036470 plasma concentration Effects 0.000 claims description 4
- 239000004055 small Interfering RNA Substances 0.000 claims description 4
- 210000001519 tissue Anatomy 0.000 claims description 4
- 210000002700 urine Anatomy 0.000 claims description 4
- 239000003524 antilipemic agent Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 claims description 2
- 108020005544 Antisense RNA Proteins 0.000 claims description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 2
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 2
- 229920001268 Cholestyramine Polymers 0.000 claims description 2
- 229920002905 Colesevelam Polymers 0.000 claims description 2
- 229920002911 Colestipol Polymers 0.000 claims description 2
- 238000002965 ELISA Methods 0.000 claims description 2
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 claims description 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 2
- 238000005481 NMR spectroscopy Methods 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 2
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- MZZLGJHLQGUVPN-HAWMADMCSA-N anacetrapib Chemical compound COC1=CC(F)=C(C(C)C)C=C1C1=CC=C(C(F)(F)F)C=C1CN1C(=O)O[C@H](C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]1C MZZLGJHLQGUVPN-HAWMADMCSA-N 0.000 claims description 2
- 229950000285 anacetrapib Drugs 0.000 claims description 2
- 239000012491 analyte Substances 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- 229960005370 atorvastatin Drugs 0.000 claims description 2
- 229960000516 bezafibrate Drugs 0.000 claims description 2
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 claims description 2
- 229920000080 bile acid sequestrant Polymers 0.000 claims description 2
- 229960005110 cerivastatin Drugs 0.000 claims description 2
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 229960001214 clofibrate Drugs 0.000 claims description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims description 2
- 229960001152 colesevelam Drugs 0.000 claims description 2
- 229960002604 colestipol Drugs 0.000 claims description 2
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003184 complementary RNA Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 235000015872 dietary supplement Nutrition 0.000 claims description 2
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 claims description 2
- 229960000815 ezetimibe Drugs 0.000 claims description 2
- 229960002297 fenofibrate Drugs 0.000 claims description 2
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 claims description 2
- 229960003627 gemfibrozil Drugs 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 238000003018 immunoassay Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000005305 interferometry Methods 0.000 claims description 2
- 229960004844 lovastatin Drugs 0.000 claims description 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000013642 negative control Substances 0.000 claims description 2
- 208000030613 peripheral artery disease Diseases 0.000 claims description 2
- 229960002797 pitavastatin Drugs 0.000 claims description 2
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims description 2
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- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 2
- IMNTVVOUWFPRSB-JWQCQUIFSA-N sch-48461 Chemical compound C1=CC(OC)=CC=C1[C@H]1N(C=2C=CC(OC)=CC=2)C(=O)[C@@H]1CCCC1=CC=CC=C1 IMNTVVOUWFPRSB-JWQCQUIFSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229960002855 simvastatin Drugs 0.000 claims description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 2
- 150000003384 small molecules Chemical group 0.000 claims description 2
- CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 claims description 2
- 229950004514 torcetrapib Drugs 0.000 claims description 2
- 238000004704 ultra performance liquid chromatography Methods 0.000 claims description 2
- MKOKWBRPIBQYJJ-WZBOJYASSA-N beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-[(15Z)-tetracosenoyl]sphingosine Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MKOKWBRPIBQYJJ-WZBOJYASSA-N 0.000 claims 3
- 229940122392 PCSK9 inhibitor Drugs 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 30
- YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 description 1
- 229940096699 bile acid sequestrants Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161556909P | 2011-11-08 | 2011-11-08 | |
| US61/556,909 | 2011-11-08 | ||
| EP11188328.6 | 2011-11-08 | ||
| EP11188328.6A EP2592423A1 (en) | 2011-11-08 | 2011-11-08 | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients not undergoing statin treatment |
| PCT/EP2012/071972 WO2013068373A2 (en) | 2011-11-08 | 2012-11-07 | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients not undergoing statin treatment |
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| JP2014532885A JP2014532885A (ja) | 2014-12-08 |
| JP2014532885A5 true JP2014532885A5 (https=) | 2016-03-24 |
| JP6388283B2 JP6388283B2 (ja) | 2018-09-12 |
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| CA (1) | CA2853220A1 (https=) |
| HK (1) | HK1202157A1 (https=) |
| WO (1) | WO2013068373A2 (https=) |
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| EP2592422A1 (en) | 2011-11-08 | 2013-05-15 | Zora Biosciences OY | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients undergoing statin treatment |
| EP2592423A1 (en) | 2011-11-08 | 2013-05-15 | Zora Biosciences OY | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients not undergoing statin treatment |
| EP2667197B1 (en) * | 2012-05-25 | 2015-09-16 | Zora Biosciences OY | Sensitive efficacy and specificity biomarkers for proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibition |
| CA2926592A1 (en) * | 2013-11-14 | 2015-05-21 | Nestec S.A. | Lipid biomarkers of healthy ageing |
| WO2015156844A1 (en) | 2014-04-10 | 2015-10-15 | MEP Equine Solutions LLC | Method for the quantification of parasite eggs in feces |
| US9347960B2 (en) | 2014-06-16 | 2016-05-24 | Zora Biosciences, Oy | Ceramides and their use in diagnosing CVD |
| CN107110939B (zh) | 2014-09-11 | 2021-05-14 | 力保科学公司 | 用于测定心血管疾病或事件的风险参数的系统 |
| WO2016100549A2 (en) | 2014-12-16 | 2016-06-23 | Washington University | Ceramides for evaluating risk of cardiovascular disease |
| US20180238914A1 (en) * | 2015-08-19 | 2018-08-23 | Metanomics Gmbh | Means and methods for diagnosing cardiac disease in a subject |
| ES2861401T3 (es) * | 2015-10-20 | 2021-10-06 | Medimmune Llc | Marcador de diagnóstico para arteriopatía coronaria |
| WO2017097852A2 (en) | 2015-12-07 | 2017-06-15 | Zora Biosciences Oy | Use of ceramides and lpls in diagnosing cvd |
| CN105424841B (zh) * | 2015-12-25 | 2017-11-03 | 齐炼文 | 用于诊断冠状动脉粥样硬化的代谢标志物 |
| CN107014942A (zh) * | 2017-05-05 | 2017-08-04 | 北京骐骥生物技术有限公司 | 利用脂质生物标志物预测糖尿病冠心病的方法 |
| CN107144624B (zh) * | 2017-05-15 | 2021-01-05 | 中国科学院生态环境研究中心 | 甄别二氧化硅颗粒来源的方法 |
| CN108037275A (zh) * | 2017-12-14 | 2018-05-15 | 北京豪思生物科技有限公司 | 一种用于评估冠状动脉疾病的试剂盒 |
| WO2019119049A1 (en) * | 2017-12-20 | 2019-06-27 | Baker Heart and Diabetes Institute | Method of predicting drug therapeutic responder status and methods of treatment |
| US12399188B2 (en) | 2018-12-06 | 2025-08-26 | Zora Biosciences Oy | Biomarkers for cardiovascular events |
| CN113533754A (zh) * | 2021-07-12 | 2021-10-22 | 北京市心肺血管疾病研究所 | 神经酰胺在制备用于评估高血压患者发生不良事件风险的试剂盒中的应用 |
| WO2024192471A1 (en) * | 2023-03-20 | 2024-09-26 | Baker Heart and Diabetes Institute | Methods of assessing metabolic health |
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| JP5264026B2 (ja) * | 1997-06-10 | 2013-08-14 | エルパス・インコーポレイテッド | 心疾患の早期発見のための方法 |
| WO2004038381A2 (en) | 2002-10-25 | 2004-05-06 | Metabolon, Inc. | Methods for drug discovery, disease treatment, and diagnosis using metabolomics |
| GB0517878D0 (en) * | 2005-09-02 | 2005-10-12 | Bioinvent Int Ab | Immunotherapeutic treatment |
| US7972802B2 (en) | 2005-10-31 | 2011-07-05 | University Of Washington | Lipoprotein-associated markers for cardiovascular disease |
| US8137977B2 (en) * | 2006-04-24 | 2012-03-20 | Children's Hospital & Research Center At Oakland | Lipidomic approaches to determining drug response phenotypes in cardiovascular disease |
| DE102006034153B4 (de) | 2006-07-24 | 2018-02-08 | Magna powertrain gmbh & co kg | Getriebe |
| WO2008148857A1 (en) | 2007-06-07 | 2008-12-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for assessing the risk of a cardiovascular disease and for diagnosing dyslipidemia |
| EP2645107B1 (en) * | 2007-06-08 | 2018-02-28 | Quest Diagnostics Investments Incorporated | Method for purifying lipoprotein suitable for analysis by differential charged-particle mobility |
| EP2048243A1 (en) | 2007-09-24 | 2009-04-15 | sanofi-aventis | Use of clec1B for the determination of cardiovascular and thrombotic risk |
| GB2469244A (en) | 2008-01-28 | 2010-10-06 | Univ Singapore | Lipid tumour profile |
| JP2011516038A (ja) | 2008-03-12 | 2011-05-26 | オタゴ イノベーション リミテッド | バイオマーカー |
| US20110294683A1 (en) | 2008-10-30 | 2011-12-01 | Centre de Recherche Public de la Sant'e | Biomarkers |
| US20110034419A1 (en) * | 2009-06-27 | 2011-02-10 | Musc Foundation For Research Development | Cardioprotective Drugs and Diagnostics for Assessing Risk of Cardiovascular Disease |
| WO2011063048A2 (en) * | 2009-11-17 | 2011-05-26 | Baylor Research Institute | Urinary triaosylceramide (gb3) as a marker of cardiac disease |
| WO2011063470A1 (en) | 2009-11-27 | 2011-06-03 | Baker Idi Heart And Diabetes Institute Holdings Limited | Lipid biomarkers for stable and unstable heart disease |
| NO2385374T3 (https=) | 2010-05-05 | 2014-06-07 | ||
| CN108445241B (zh) | 2010-06-20 | 2021-11-02 | 佐拉生物科学公司 | 用于鉴定高风险冠状动脉疾病患者的脂质组学标志 |
| JP5980900B2 (ja) | 2011-04-08 | 2016-08-31 | ゾラ バイオサイエンシーズ オサケ ユキチュア | スタチン誘発性筋毒性の高感度検出のためのバイオマーカー |
| EP2592422A1 (en) | 2011-11-08 | 2013-05-15 | Zora Biosciences OY | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients undergoing statin treatment |
| EP2592423A1 (en) | 2011-11-08 | 2013-05-15 | Zora Biosciences OY | Lipidomic biomarkers for the prediction of cardiovascular outcomes in coronary artery disease patients not undergoing statin treatment |
-
2011
- 2011-11-08 EP EP11188328.6A patent/EP2592423A1/en not_active Withdrawn
-
2012
- 2012-11-07 US US14/356,594 patent/US9052328B2/en active Active
- 2012-11-07 EP EP12781324.4A patent/EP2776841B1/en active Active
- 2012-11-07 HK HK15102644.9A patent/HK1202157A1/xx unknown
- 2012-11-07 CA CA2853220A patent/CA2853220A1/en not_active Abandoned
- 2012-11-07 EP EP17150693.4A patent/EP3208617B1/en active Active
- 2012-11-07 CN CN201280054323.8A patent/CN103917876B/zh active Active
- 2012-11-07 WO PCT/EP2012/071972 patent/WO2013068373A2/en not_active Ceased
- 2012-11-07 JP JP2014540426A patent/JP6388283B2/ja active Active
-
2015
- 2015-05-27 US US14/722,964 patent/US9423406B2/en active Active
-
2016
- 2016-07-14 US US15/210,048 patent/US9863965B2/en active Active
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