JPH0449551B2 - - Google Patents
Info
- Publication number
- JPH0449551B2 JPH0449551B2 JP22936784A JP22936784A JPH0449551B2 JP H0449551 B2 JPH0449551 B2 JP H0449551B2 JP 22936784 A JP22936784 A JP 22936784A JP 22936784 A JP22936784 A JP 22936784A JP H0449551 B2 JPH0449551 B2 JP H0449551B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydrobenzopyran
- benzopyran
- tetramethyl
- dihydro
- compound
- 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.)
- Expired
Links
- -1 nicotinoyl group Chemical group 0.000 claims description 19
- 210000004369 blood Anatomy 0.000 claims description 14
- 239000008280 blood Substances 0.000 claims description 14
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003524 antilipemic agent Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 13
- 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 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000001968 nicotinic acid Nutrition 0.000 description 8
- 239000011664 nicotinic acid Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- GZCJJOLJSBCUNR-UHFFFAOYSA-N chroman-6-ol Chemical compound O1CCCC2=CC(O)=CC=C21 GZCJJOLJSBCUNR-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229960003512 nicotinic acid Drugs 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VRAHPESAMYMDQI-UHFFFAOYSA-N Nicomol Chemical compound C1CCC(COC(=O)C=2C=NC=CC=2)(COC(=O)C=2C=NC=CC=2)C(O)C1(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 VRAHPESAMYMDQI-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229950001071 nicomol Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WQLAMERSARXVBS-UHFFFAOYSA-N (6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methyl pyridine-3-carboxylate Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(=O)C1=CC=CN=C1 WQLAMERSARXVBS-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZOVSZMJTWVZDFS-UHFFFAOYSA-N 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)ethyl pyridine-3-carboxylate Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)CCOC(=O)C1=CC=CN=C1 ZOVSZMJTWVZDFS-UHFFFAOYSA-N 0.000 description 1
- QPWRLXHOVLBKID-UHFFFAOYSA-N 2-[2,5,7,8-tetramethyl-6-(pyridine-3-carbonyloxy)-3,4-dihydrochromen-2-yl]ethyl pyridine-3-carboxylate Chemical compound C1CC=2C(C)=C(OC(=O)C=3C=NC=CC=3)C(C)=C(C)C=2OC1(C)CCOC(=O)C1=CC=CN=C1 QPWRLXHOVLBKID-UHFFFAOYSA-N 0.000 description 1
- NAHHIXKSGGSPOL-UHFFFAOYSA-N 2h-chromen-6-ol Chemical compound O1CC=CC2=CC(O)=CC=C21 NAHHIXKSGGSPOL-UHFFFAOYSA-N 0.000 description 1
- XTMVDYMHFQIDOH-UHFFFAOYSA-N 4-methylbenzenesulfonate;pyridin-1-ium-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1.CC1=CC=C(S(O)(=O)=O)C=C1 XTMVDYMHFQIDOH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- MHBUENIZXLHJCH-UHFFFAOYSA-N [2-(2-hydroxyethyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] pyridine-3-carboxylate Chemical compound CC1=C(C)C=2OC(C)(CCO)CCC=2C(C)=C1OC(=O)C1=CC=CN=C1 MHBUENIZXLHJCH-UHFFFAOYSA-N 0.000 description 1
- RVSNGCIONYJGTI-UHFFFAOYSA-N [2-(pyridine-3-carbonyloxy)-3-[2,5,7,8-tetramethyl-6-(pyridine-3-carbonyloxy)-3,4-dihydrochromen-2-yl]propyl] pyridine-3-carboxylate Chemical compound C1CC=2C(C)=C(OC(=O)C=3C=NC=CC=3)C(C)=C(C)C=2OC1(C)CC(OC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 RVSNGCIONYJGTI-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000260 hypercholesteremic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000002960 lipid emulsion Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229960000827 niceritrol Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22936784A JPS61106571A (ja) | 1984-10-30 | 1984-10-30 | ３，４−ジヒドロベンゾピラン誘導体及びこれを有効成分とする血中脂質低下剤 |
| US06/790,670 US4681890A (en) | 1984-10-30 | 1985-10-23 | 3,4-dihydrobenzopyran compounds and pharmaceutical composition containing the same |
| AT85113726T ATE50995T1 (de) | 1984-10-30 | 1985-10-29 | 3,4-dihydrobenzopyranverbindungen und diese enthaltende pharmazeutische zusammenstellungen. |
| EP85113726A EP0180190B1 (de) | 1984-10-30 | 1985-10-29 | 3,4-Dihydrobenzopyranverbindungen und diese enthaltende pharmazeutische Zusammenstellungen |
| DE8585113726T DE3576505D1 (de) | 1984-10-30 | 1985-10-29 | 3,4-dihydrobenzopyranverbindungen und diese enthaltende pharmazeutische zusammenstellungen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22936784A JPS61106571A (ja) | 1984-10-30 | 1984-10-30 | ３，４−ジヒドロベンゾピラン誘導体及びこれを有効成分とする血中脂質低下剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61106571A JPS61106571A (ja) | 1986-05-24 |
| JPH0449551B2 true JPH0449551B2 (de) | 1992-08-11 |
Family
ID=16891055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22936784A Granted JPS61106571A (ja) | 1984-10-30 | 1984-10-30 | ３，４−ジヒドロベンゾピラン誘導体及びこれを有効成分とする血中脂質低下剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61106571A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100402054B1 (ko) * | 2001-03-30 | 2003-10-17 | 한국화학연구원 | 항산화 활성을 갖는 2-아릴-2-메틸-2,3-디히드로벤조퓨란화합물 |
-
1984
- 1984-10-30 JP JP22936784A patent/JPS61106571A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61106571A (ja) | 1986-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5698527A (en) | Steroidal glycosides as antihyperlipidemic agents | |
| CZ285970B6 (cs) | Deriváty benzopyranu, meziprodukty pro jejich výrobu a farmaceutické prostředky na jejich bázi | |
| KR102551018B1 (ko) | 디히드로피리미딘-2-온 화합물 및 그의 의약 용도 | |
| JPS6323878A (ja) | ７−アシルオキシ−６−アミノアシルオキシポリオキシラブダンおよびその製法 | |
| JPH0640994A (ja) | 薬理活性のある新規テトラロン類 | |
| EP0180190B1 (de) | 3,4-Dihydrobenzopyranverbindungen und diese enthaltende pharmazeutische Zusammenstellungen | |
| JPH01151570A (ja) | クロマン誘導体、その製造法、及びその医薬での使用 | |
| FR2486076A1 (fr) | Aminocyclopentanone amides, leur preparation et compositions pharmaceutiques qui les contiennent | |
| AU3159293A (en) | New BHT ether compounds and their use as hypolipidemic and antiatherosclerotic drugs | |
| JPH0449551B2 (de) | ||
| JPH0578552B2 (de) | ||
| EP0373204A1 (de) | Verbindungen und behandlung | |
| JPH06329665A (ja) | 新規な置換ベンゾジオキシン類、その製造法及びそのベンゾジオキシン類を含有する製剤組成物 | |
| DE69122284T2 (de) | 4-Hydroxytetrahydropyran-2-on Derivate nützlich als cholesterin- und lipidsenkende Agenzien | |
| EP0228314A2 (de) | Verwendung von Äthanolamin-derivaten zur Behandlung oder Prävention von Hyperlipämie | |
| JPH01313474A (ja) | ５‐クロル‐３‐クロルスルホニル‐２‐チオフエンカルボン酸エステルの製造方法 | |
| JPS62209070A (ja) | ネオリグナン誘導体 | |
| JPH08217672A (ja) | キサントン誘導体を含有する抗ヘリコバクター・ピロリ薬 | |
| CA1279646C (en) | 3,4-dihydrobenzopyran compounds and pharmaceutical composition containing the same | |
| JPS6339862A (ja) | ピリジルアミノフエノ−ル誘導体 | |
| JP2662607B2 (ja) | ビシクロ［８．３．０］トリデカ―９，１３―ジエン―２，７―ジイン誘導体 | |
| EP0200345A2 (de) | Antiallergische oder antiinflammatorische substituierte (Hetero)-aralkyl-amino-ortho-phenole | |
| JPH0578551B2 (de) | ||
| JPH1129471A (ja) | クマリン誘導体を薬効成分として含有する肝疾患治療剤 | |
| KR100247561B1 (ko) | 신규한 피리디닐메틸아민 유도체와 그 제조방법 및 이를 함유하는 약제조성물 |