JPS60174766A - ピロ−ル誘導体 - Google Patents
ピロ−ル誘導体Info
- Publication number
- JPS60174766A JPS60174766A JP3125884A JP3125884A JPS60174766A JP S60174766 A JPS60174766 A JP S60174766A JP 3125884 A JP3125884 A JP 3125884A JP 3125884 A JP3125884 A JP 3125884A JP S60174766 A JPS60174766 A JP S60174766A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- compound
- ethyl
- compound shown
- 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
- 150000003233 pyrroles Chemical class 0.000 title abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 29
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 241000124008 Mammalia Species 0.000 abstract description 3
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 208000000718 duodenal ulcer Diseases 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract description 2
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 201000005917 gastric ulcer Diseases 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- -1 cyclic acid anhydride Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical class CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-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
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RIEVLFARERLSRN-UHFFFAOYSA-N O=C1CCC(=O)N1CCC1=CC=CN1 Chemical compound O=C1CCC(=O)N1CCC1=CC=CN1 RIEVLFARERLSRN-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- MFSHZGFPADYOTO-UHFFFAOYSA-N chloromethyl methyl carbonate Chemical compound COC(=O)OCCl MFSHZGFPADYOTO-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 210000000554 iris Anatomy 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3125884A JPS60174766A (ja) | 1984-02-20 | 1984-02-20 | ピロ−ル誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3125884A JPS60174766A (ja) | 1984-02-20 | 1984-02-20 | ピロ−ル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60174766A true JPS60174766A (ja) | 1985-09-09 |
| JPH0447666B2 JPH0447666B2 (https=) | 1992-08-04 |
Family
ID=12326323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3125884A Granted JPS60174766A (ja) | 1984-02-20 | 1984-02-20 | ピロ−ル誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60174766A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01503627A (ja) * | 1987-06-25 | 1989-12-07 | ビーピー ケミカルズ （アディティブス） リミテッド | 新規なカルバメート、その製造および燃料添加剤としてのその使用 |
-
1984
- 1984-02-20 JP JP3125884A patent/JPS60174766A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01503627A (ja) * | 1987-06-25 | 1989-12-07 | ビーピー ケミカルズ （アディティブス） リミテッド | 新規なカルバメート、その製造および燃料添加剤としてのその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0447666B2 (https=) | 1992-08-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1129102A (zh) | 用作肿瘤坏死因子释放抑制剂的儿茶酚二醚化合物 | |
| LU84157A1 (fr) | Nouvelles 1,2-diaminocyclobutene-3,4-diones,leur procede de preparation et composition pharmaceutique les contenant | |
| LU82613A1 (fr) | Amides antihypertensives | |
| EP0371876A1 (fr) | Composés isoxazoles et isoxazolines à activité anticonvulsivante, procédé de préparation et compositions thérapeutiques les contenant | |
| FR2542312A1 (fr) | Composes de sulfonium, leur preparation et compositions pharmaceutiques contenant ces composes | |
| CA1212380A (fr) | Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole | |
| JP4961357B2 (ja) | イソオキサゾリン誘導体及びその製造方法 | |
| JPS6212788B2 (https=) | ||
| CN102317256B (zh) | 制备消旋卡多曲的方法 | |
| JPS60174766A (ja) | ピロ−ル誘導体 | |
| CA2034673A1 (en) | 1-phenylalkyl-3-phenylurea derivative | |
| JPS6399057A (ja) | グリシン誘導体 | |
| JP2006500409A5 (https=) | ||
| JPS6044304B2 (ja) | フエニルプロピオン酸誘導体の製造方法 | |
| CH619951A5 (en) | Process for the preparation of condensed pyrimidines | |
| JP2526811B2 (ja) | フェネチルアミン誘導体及びその製法 | |
| JPH02502728A (ja) | アルドースレダクターゼ抑制剤としてのｎ―ナフトイルグリシン | |
| JPS5910563A (ja) | α−（Ｎ−ピロリル）−フエニル酢酸誘導体およびその製造方法 | |
| JPH078853B2 (ja) | ドーパミン誘導体の製法 | |
| FR2505329A1 (fr) | Esters 2-methoxyphenyliques d'amino-acides n-substitues, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| JPS6026386B2 (ja) | 新規イソインド−ル化合物 | |
| CH618977A5 (https=) | ||
| FR2584722A1 (fr) | Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent | |
| CA1088074A (fr) | Procede d'obtention de nouveaux dispirodecanes et les produits en resultant | |
| JPH02502727A (ja) | アルドースレダクターゼ抑制剤としてのｎ‐アシル‐ｎ‐ナフトイルグリシン |