JPS60197642A - エタノ−ルアミン誘導体およびこれを有効成分として含有する血小板凝集抑制剤 - Google Patents
エタノ−ルアミン誘導体およびこれを有効成分として含有する血小板凝集抑制剤Info
- Publication number
- JPS60197642A JPS60197642A JP5379684A JP5379684A JPS60197642A JP S60197642 A JPS60197642 A JP S60197642A JP 5379684 A JP5379684 A JP 5379684A JP 5379684 A JP5379684 A JP 5379684A JP S60197642 A JPS60197642 A JP S60197642A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- higher fatty
- fatty acid
- platelet aggregation
- acyl group
- 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.)
- Granted
Links
- 150000002169 ethanolamines Chemical class 0.000 title claims description 18
- 239000004480 active ingredient Substances 0.000 title claims description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 title abstract description 20
- 210000001772 blood platelet Anatomy 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 30
- 239000000194 fatty acid Substances 0.000 claims abstract description 30
- 229930195729 fatty acid Natural products 0.000 claims abstract description 30
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 30
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000002252 acyl group Chemical group 0.000 claims abstract description 17
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000001968 nicotinic acid Nutrition 0.000 claims abstract description 14
- 239000011664 nicotinic acid Substances 0.000 claims abstract description 14
- 229960003512 nicotinic acid Drugs 0.000 claims abstract description 13
- 150000005671 trienes Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims description 15
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims description 8
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims description 8
- 229940127218 antiplatelet drug Drugs 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 206010027476 Metastases Diseases 0.000 abstract description 7
- 206010028980 Neoplasm Diseases 0.000 abstract description 7
- 201000011510 cancer Diseases 0.000 abstract description 7
- 230000009401 metastasis Effects 0.000 abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000003449 preventive effect Effects 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 208000007536 Thrombosis Diseases 0.000 abstract description 5
- 239000012300 argon atmosphere Substances 0.000 abstract description 3
- 208000010125 myocardial infarction Diseases 0.000 abstract description 3
- 206010008118 cerebral infarction Diseases 0.000 abstract description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OVKKNJPJQKTXIT-UHFFFAOYSA-N n-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide Chemical compound CCC=CCC=CCC=CCC=CCC=CCCCC(=O)NCCO OVKKNJPJQKTXIT-UHFFFAOYSA-N 0.000 abstract 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- 150000001793 charged compounds Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 230000000702 anti-platelet effect Effects 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- SJZLOWYUGKIWAK-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound OCCNC(=O)C1=CC=CN=C1 SJZLOWYUGKIWAK-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- SBHCLVQMTBWHCD-METXMMQOSA-N (2e,4e,6e,8e,10e)-icosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C(O)=O SBHCLVQMTBWHCD-METXMMQOSA-N 0.000 description 1
- ZNPNOVHKCAAQCG-UHFFFAOYSA-N 2-chloro-1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1Cl ZNPNOVHKCAAQCG-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- -1 N-nicotinoyl-2-aminoethyl Chemical group 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004848 nephelometry Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5379684A JPS60197642A (ja) | 1984-03-21 | 1984-03-21 | エタノ−ルアミン誘導体およびこれを有効成分として含有する血小板凝集抑制剤 |
| US06/713,496 US4619938A (en) | 1984-03-21 | 1985-03-19 | Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet aggregation inhibitors |
| EP85103253A EP0161422B1 (en) | 1984-03-21 | 1985-03-20 | Alkanolamine derivatives and platelet aggregation inhibitors containing the same as an active ingredient |
| DE8585103253T DE3568427D1 (en) | 1984-03-21 | 1985-03-20 | Alkanolamine derivatives and platelet aggregation inhibitors containing the same as an active ingredient |
| BE0/214681A BE901987A (fr) | 1984-03-21 | 1985-03-21 | Derives d'alcanolamines et inhibiteurs de l'agregation des plaquettes en contenant comme principe actif. |
| IT19992/85A IT1185097B (it) | 1984-03-21 | 1985-03-21 | Derivati alcanolaminici e inibitori di aggregazione delle piastrine contenenti gli stessi come un ingrediente attivo |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5379684A JPS60197642A (ja) | 1984-03-21 | 1984-03-21 | エタノ−ルアミン誘導体およびこれを有効成分として含有する血小板凝集抑制剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60197642A true JPS60197642A (ja) | 1985-10-07 |
| JPH0113703B2 JPH0113703B2 (enrdf_load_stackoverflow) | 1989-03-07 |
Family
ID=12952777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5379684A Granted JPS60197642A (ja) | 1984-03-21 | 1984-03-21 | エタノ−ルアミン誘導体およびこれを有効成分として含有する血小板凝集抑制剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60197642A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62106019A (ja) * | 1985-11-01 | 1987-05-16 | Terumo Corp | 抗高脂血症剤 |
| JP2023533864A (ja) * | 2020-07-17 | 2023-08-04 | サノフィ・パスツール | 式－ｎｈ－ｃｘ－ａまたは－ｎｈ－ｃｘ－ｎｈ－ａの少なくとも１つの末端ラジカルを含む脂質化合物、それらを含有する組成物およびそれらの使用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911368A (enrdf_load_stackoverflow) * | 1972-05-31 | 1974-01-31 |
-
1984
- 1984-03-21 JP JP5379684A patent/JPS60197642A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911368A (enrdf_load_stackoverflow) * | 1972-05-31 | 1974-01-31 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62106019A (ja) * | 1985-11-01 | 1987-05-16 | Terumo Corp | 抗高脂血症剤 |
| JP2023533864A (ja) * | 2020-07-17 | 2023-08-04 | サノフィ・パスツール | 式－ｎｈ－ｃｘ－ａまたは－ｎｈ－ｃｘ－ｎｈ－ａの少なくとも１つの末端ラジカルを含む脂質化合物、それらを含有する組成物およびそれらの使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0113703B2 (enrdf_load_stackoverflow) | 1989-03-07 |
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