JPS6141354B2 - - Google Patents
Info
- Publication number
- JPS6141354B2 JPS6141354B2 JP53000662A JP66278A JPS6141354B2 JP S6141354 B2 JPS6141354 B2 JP S6141354B2 JP 53000662 A JP53000662 A JP 53000662A JP 66278 A JP66278 A JP 66278A JP S6141354 B2 JPS6141354 B2 JP S6141354B2
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- general formula
- group
- acetic acid
- carbamoyl
- 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 Imide esters Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000002460 imidazoles Chemical class 0.000 claims description 7
- GFQBSQXXHYLABK-UHFFFAOYSA-N 2-aminopropanediamide Chemical compound NC(=O)C(N)C(N)=O GFQBSQXXHYLABK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006136 alcoholysis reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002463 imidates Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- WUJUYHMGDPTLMG-UHFFFAOYSA-N imidazol-2-ylacetic acid Chemical class OC(=O)CC1=NC=CN1 WUJUYHMGDPTLMG-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- PKVIDZFYUHJCTC-UHFFFAOYSA-N ethyl 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetate Chemical compound CCOC(=O)CC1=NC(C(N)=O)=C(O)N1 PKVIDZFYUHJCTC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 description 1
- BJSNFBRLXFJQBY-UHFFFAOYSA-N 1-o-ethyl 3-o-(2-iminoethyl) propanedioate;hydrochloride Chemical compound Cl.CCOC(=O)CC(=O)OCC=N BJSNFBRLXFJQBY-UHFFFAOYSA-N 0.000 description 1
- MAIUPBMVDKBWRE-UHFFFAOYSA-N 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetic acid Chemical compound NC(=O)C=1N=C(CC(O)=O)NC=1O MAIUPBMVDKBWRE-UHFFFAOYSA-N 0.000 description 1
- QGONUCJYLPRUMN-UHFFFAOYSA-N 2-methylpropyl 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetate Chemical compound CC(C)COC(=O)CC1=NC(C(N)=O)=C(O)N1 QGONUCJYLPRUMN-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- TXVAYNGMYQXJAA-UHFFFAOYSA-N butyl 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetate Chemical compound CCCCOC(=O)CC1=NC(C(N)=O)=C(O)N1 TXVAYNGMYQXJAA-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000004727 humoral immunity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002766 immunoenhancing effect Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JVGUHIFSHFRADI-UHFFFAOYSA-N methyl 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetate Chemical compound COC(=O)CC1=NC(C(N)=O)=C(O)N1 JVGUHIFSHFRADI-UHFFFAOYSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- TVARAGDCMHFKIQ-UHFFFAOYSA-N propyl 2-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)acetate Chemical compound CCCOC(=O)CC1=NC(C(N)=O)=C(O)N1 TVARAGDCMHFKIQ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP66278A JPS5495568A (en) | 1978-01-06 | 1978-01-06 | Novel imidazoleacetic acid derivative |
| US05/971,826 US4209525A (en) | 1978-01-06 | 1978-12-19 | Imidazole acetic acid derivatives |
| AU42944/78A AU518254B2 (en) | 1978-01-06 | 1978-12-28 | Imidazole acetic acid derivatives |
| DE7878300921T DE2861682D1 (en) | 1978-01-06 | 1978-12-29 | Immunostimulatory imidazole derivatives, their preparation and their pharmaceutical compositions |
| EP78300921A EP0003265B1 (en) | 1978-01-06 | 1978-12-29 | Immunostimulatory imidazole derivatives, their preparation and their pharmaceutical compositions |
| CA319,147A CA1102814A (en) | 1978-01-06 | 1979-01-04 | Imidazole acetic acid derivatives |
| AT0010679A AT367751B (de) | 1978-01-06 | 1979-01-05 | Verfahren zur herstellung von neuen imidazolderivaten und von deren salzen |
| HU79SU1003A HU180958B (en) | 1978-01-06 | 1979-01-05 | Process for preparing imidazol-acetic acid derivatives |
| DK005879A DK154075C (da) | 1978-01-06 | 1979-01-05 | Analogifremgangsmaade til fremstilling af 4-carbamoyl-5-hydroxy-imidazolderivater eller farmaceutisk acceptable salte deraf |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP66278A JPS5495568A (en) | 1978-01-06 | 1978-01-06 | Novel imidazoleacetic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5495568A JPS5495568A (en) | 1979-07-28 |
| JPS6141354B2 true JPS6141354B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-09-13 |
Family
ID=11479927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP66278A Granted JPS5495568A (en) | 1978-01-06 | 1978-01-06 | Novel imidazoleacetic acid derivative |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59167515A (ja) * | 1983-03-15 | 1984-09-21 | Ajinomoto Co Inc | 免疫機能増強剤 |
| JPS60193997A (ja) * | 1984-03-14 | 1985-10-02 | Sumitomo Chem Co Ltd | 新規シアノイミダゾ−ルリボヌクレオシド誘導体およびその製造法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5188965A (en) * | 1975-01-29 | 1976-08-04 | 55 hidorokishi imidazooru 44 karubokisaamidonoshinkinaseizoho | |
| AU502122B2 (en) * | 1976-07-02 | 1979-07-12 | Sumitomo Chemical Company, Limited | 5-0-acylated-imidazole-4-carboxamide derivatives |
| JPS604802B2 (ja) * | 1976-09-07 | 1985-02-06 | 住友化学工業株式会社 | 制癌剤 |
| US4140788A (en) * | 1976-11-10 | 1979-02-20 | Sumitomo Chemical Company, Limited | N-Substituted imidazolecarboxamide derivatives |
-
1978
- 1978-01-06 JP JP66278A patent/JPS5495568A/ja active Granted
- 1978-12-19 US US05/971,826 patent/US4209525A/en not_active Expired - Lifetime
- 1978-12-28 AU AU42944/78A patent/AU518254B2/en not_active Expired
- 1978-12-29 DE DE7878300921T patent/DE2861682D1/de not_active Expired
- 1978-12-29 EP EP78300921A patent/EP0003265B1/en not_active Expired
-
1979
- 1979-01-04 CA CA319,147A patent/CA1102814A/en not_active Expired
- 1979-01-05 HU HU79SU1003A patent/HU180958B/hu unknown
- 1979-01-05 DK DK005879A patent/DK154075C/da active
- 1979-01-05 AT AT0010679A patent/AT367751B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4209525A (en) | 1980-06-24 |
| DK154075C (da) | 1989-07-03 |
| HU180958B (en) | 1983-05-30 |
| AU518254B2 (en) | 1981-09-24 |
| DE2861682D1 (en) | 1982-04-15 |
| JPS5495568A (en) | 1979-07-28 |
| CA1102814A (en) | 1981-06-09 |
| AT367751B (de) | 1982-07-26 |
| DK5879A (da) | 1979-07-07 |
| DK154075B (da) | 1988-10-10 |
| EP0003265A1 (en) | 1979-08-08 |
| EP0003265B1 (en) | 1982-03-17 |
| ATA10679A (de) | 1981-12-15 |
| AU4294478A (en) | 1979-07-12 |
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