JPS60222481A - 新規なジフエニルピロリルチアゾ−ル誘導体、その製造法およびそれを有効成分とする医薬組成物 - Google Patents
新規なジフエニルピロリルチアゾ−ル誘導体、その製造法およびそれを有効成分とする医薬組成物Info
- Publication number
- JPS60222481A JPS60222481A JP7992484A JP7992484A JPS60222481A JP S60222481 A JPS60222481 A JP S60222481A JP 7992484 A JP7992484 A JP 7992484A JP 7992484 A JP7992484 A JP 7992484A JP S60222481 A JPS60222481 A JP S60222481A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- following formula
- group
- bis
- methoxyphenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
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- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
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- VBZYZJWZVXYEHS-UHFFFAOYSA-N 2-(1-ethylpyrrol-2-yl)-4,5-bis(4-methoxyphenyl)-1,3-thiazole Chemical compound CCN1C=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=C(C=2C=CC(OC)=CC=2)S1 VBZYZJWZVXYEHS-UHFFFAOYSA-N 0.000 abstract description 2
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- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- DDMGAAYEUNWXSI-XVSDJDOKSA-M sodium;(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate Chemical compound [Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O DDMGAAYEUNWXSI-XVSDJDOKSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7992484A JPS60222481A (ja) | 1984-04-19 | 1984-04-19 | 新規なジフエニルピロリルチアゾ−ル誘導体、その製造法およびそれを有効成分とする医薬組成物 |
| US06/722,322 US4659726A (en) | 1984-04-19 | 1985-04-12 | Novel 4,5-Bis (4-methoxyphenyl)-2-(pyrrol-2-yl) thiazoles and pharmaceutical composition containing the same |
| AT85104786T ATE40890T1 (de) | 1984-04-19 | 1985-04-19 | 4,5-bis-(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten. |
| DE8585104786T DE3568333D1 (en) | 1984-04-19 | 1985-04-19 | Novel 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazoles, process for the preparation thereof and pharmaceutical composition containing the same |
| EP85104786A EP0159677B1 (en) | 1984-04-19 | 1985-04-19 | Novel 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazoles, process for the preparation thereof and pharmaceutical composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7992484A JPS60222481A (ja) | 1984-04-19 | 1984-04-19 | 新規なジフエニルピロリルチアゾ−ル誘導体、その製造法およびそれを有効成分とする医薬組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60222481A true JPS60222481A (ja) | 1985-11-07 |
| JPH0512350B2 JPH0512350B2 (enrdf_load_stackoverflow) | 1993-02-17 |
Family
ID=13703850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7992484A Granted JPS60222481A (ja) | 1984-04-19 | 1984-04-19 | 新規なジフエニルピロリルチアゾ−ル誘導体、その製造法およびそれを有効成分とする医薬組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60222481A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643932A (en) * | 1990-11-30 | 1997-07-01 | Otsuka Pharmaceutical Co., Ltd. | Superoxide radical inhibitor |
| US8354439B2 (en) | 1996-09-30 | 2013-01-15 | Otsuka Pharmaceutical Co., Ltd. | Agent for inhibition of cytokine production and agent for inhibition of cell adhesion |
-
1984
- 1984-04-19 JP JP7992484A patent/JPS60222481A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643932A (en) * | 1990-11-30 | 1997-07-01 | Otsuka Pharmaceutical Co., Ltd. | Superoxide radical inhibitor |
| US5677319A (en) * | 1990-11-30 | 1997-10-14 | Otsuka Pharmaceutical Co., Ltd. | Superoxide radical inhibitor |
| US6080764A (en) * | 1990-11-30 | 2000-06-27 | Otsuka Pharmaceutical Co., Ltd. | Superoxide radical inhibitor |
| USRE37556E1 (en) | 1990-11-30 | 2002-02-19 | Otsuka Pharmaceutical Co., Ltd. | Superoxide radical inhibitor |
| US8354439B2 (en) | 1996-09-30 | 2013-01-15 | Otsuka Pharmaceutical Co., Ltd. | Agent for inhibition of cytokine production and agent for inhibition of cell adhesion |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0512350B2 (enrdf_load_stackoverflow) | 1993-02-17 |
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