JPS5879944A - ３，５−ジ・タ−シヤリ−・ブチルスチレン誘導体及び抗炎症、鎮痛、解熱剤並びに血小板凝集阻害剤 - Google Patents
３，５−ジ・タ−シヤリ−・ブチルスチレン誘導体及び抗炎症、鎮痛、解熱剤並びに血小板凝集阻害剤Info
- Publication number
- JPS5879944A JPS5879944A JP17994881A JP17994881A JPS5879944A JP S5879944 A JPS5879944 A JP S5879944A JP 17994881 A JP17994881 A JP 17994881A JP 17994881 A JP17994881 A JP 17994881A JP S5879944 A JPS5879944 A JP S5879944A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- butylstyrene
- group
- hydrogen
- tertiary
- 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
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- 239000002260 anti-inflammatory agent Substances 0.000 title claims abstract description 4
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- 230000000202 analgesic effect Effects 0.000 title abstract description 13
- 208000010110 spontaneous platelet aggregation Diseases 0.000 title abstract description 12
- -1 analgesic Substances 0.000 title abstract description 9
- 230000001754 anti-pyretic effect Effects 0.000 title abstract description 8
- 239000003112 inhibitor Substances 0.000 title abstract description 4
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- 210000001772 blood platelet Anatomy 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
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- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
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- 239000001301 oxygen Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
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- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000730 antalgic agent Substances 0.000 claims description 2
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- 150000001875 compounds Chemical class 0.000 abstract description 74
- 238000000034 method Methods 0.000 abstract description 23
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- 239000000463 material Substances 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 231100000957 no side effect Toxicity 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
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- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 239000000203 mixture Substances 0.000 description 9
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 230000002401 inhibitory effect Effects 0.000 description 6
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- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical class CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 5
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- 235000010489 acacia gum Nutrition 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
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- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic 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 |
|---|---|---|---|
| JP17994881A JPS5879944A (ja) | 1981-11-09 | 1981-11-09 | ３，５−ジ・タ−シヤリ−・ブチルスチレン誘導体及び抗炎症、鎮痛、解熱剤並びに血小板凝集阻害剤 |
| US06/337,168 US4431656A (en) | 1981-02-05 | 1982-01-05 | 3,5-di-Tert-butylstyrene derivatives, salts thereof, and pharmaceutical compositions containing the same as an active ingredient |
| CA000395217A CA1187505A (en) | 1981-02-05 | 1982-01-29 | 3,5-di-tert-butylstyrene derivatives, salts thereof, and pharmaceutical compositions containing the same as an active ingredient |
| DE8282100661T DE3270202D1 (en) | 1981-02-05 | 1982-01-30 | 3,5-di-tert-butylstyrene derivatives, processes for their preparations, and pharmaceutical compositions containing them |
| EP82100661A EP0057882B1 (en) | 1981-02-05 | 1982-01-30 | 3,5-di-tert-butylstyrene derivatives, processes for their preparations, and pharmaceutical compositions containing them |
| AT82100661T ATE18907T1 (de) | 1981-02-05 | 1982-01-30 | 3,5-di-tert-butylstyrenderivate, verfahren zu ihrer herstellung und pharmazeutische zusammenstellungen, die sie enthalten. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17994881A JPS5879944A (ja) | 1981-11-09 | 1981-11-09 | ３，５−ジ・タ−シヤリ−・ブチルスチレン誘導体及び抗炎症、鎮痛、解熱剤並びに血小板凝集阻害剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5879944A true JPS5879944A (ja) | 1983-05-13 |
| JPS6324498B2 JPS6324498B2 (en, 2012) | 1988-05-20 |
Family
ID=16074740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17994881A Granted JPS5879944A (ja) | 1981-02-05 | 1981-11-09 | ３，５−ジ・タ−シヤリ−・ブチルスチレン誘導体及び抗炎症、鎮痛、解熱剤並びに血小板凝集阻害剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5879944A (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6157553A (ja) * | 1984-08-28 | 1986-03-24 | Kanegafuchi Chem Ind Co Ltd | 新規３，５−ジタ−シヤリ−ブチルフエニル誘導体 |
| JPS61257967A (ja) * | 1985-05-09 | 1986-11-15 | Eisai Co Ltd | ２−ピロリドン誘導体 |
| JPS6229570A (ja) * | 1985-07-29 | 1987-02-07 | Kanegafuchi Chem Ind Co Ltd | ３，５−ジイソプロピルベンジリデン複素環式化合物 |
| JPS6242977A (ja) * | 1985-08-09 | 1987-02-24 | イ−ライ・リリ−・アンド・カンパニ− | ジ−ｔ−ブチルフエノ−ル化合物 |
| WO1992012966A1 (fr) * | 1991-01-21 | 1992-08-06 | Shionogi Seiyaku Kabushiki Kaisha | Analogue de 3-benzylidene-1-carbamoyl-2-pyrrolidone |
-
1981
- 1981-11-09 JP JP17994881A patent/JPS5879944A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6157553A (ja) * | 1984-08-28 | 1986-03-24 | Kanegafuchi Chem Ind Co Ltd | 新規３，５−ジタ−シヤリ−ブチルフエニル誘導体 |
| JPS61257967A (ja) * | 1985-05-09 | 1986-11-15 | Eisai Co Ltd | ２−ピロリドン誘導体 |
| JPS6229570A (ja) * | 1985-07-29 | 1987-02-07 | Kanegafuchi Chem Ind Co Ltd | ３，５−ジイソプロピルベンジリデン複素環式化合物 |
| JPS6242977A (ja) * | 1985-08-09 | 1987-02-24 | イ−ライ・リリ−・アンド・カンパニ− | ジ−ｔ−ブチルフエノ−ル化合物 |
| WO1992012966A1 (fr) * | 1991-01-21 | 1992-08-06 | Shionogi Seiyaku Kabushiki Kaisha | Analogue de 3-benzylidene-1-carbamoyl-2-pyrrolidone |
| US5319099A (en) * | 1991-01-21 | 1994-06-07 | Shionogi Seiyaku Kabushiki Kaisha | 3-benzylidene-1-carbamoyl-2-pyrrolidone compounds useful as antiinflammatory agents |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6324498B2 (en, 2012) | 1988-05-20 |
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