DE2200499A1 - 2-phenyl-5-amino-imidazole, ihre pharmakologisch vertraeglichen salze, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende antiphlogistische arzneipraeparate - Google Patents
2-phenyl-5-amino-imidazole, ihre pharmakologisch vertraeglichen salze, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende antiphlogistische arzneipraeparateInfo
- Publication number
- DE2200499A1 DE2200499A1 DE19722200499 DE2200499A DE2200499A1 DE 2200499 A1 DE2200499 A1 DE 2200499A1 DE 19722200499 DE19722200499 DE 19722200499 DE 2200499 A DE2200499 A DE 2200499A DE 2200499 A1 DE2200499 A1 DE 2200499A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- imidazole
- methyl
- hydrogen
- amino
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- MOJYDLJMKAMQDC-UHFFFAOYSA-N 2-phenyl-1h-imidazol-5-amine Chemical compound N1C(N)=CN=C1C1=CC=CC=C1 MOJYDLJMKAMQDC-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 230000001741 anti-phlogistic effect Effects 0.000 title 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 106
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- -1 nitro, methyl Chemical group 0.000 claims description 15
- 150000002460 imidazoles Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- GTIYLLQEFVPNTN-UHFFFAOYSA-N 2-(4-fluorophenyl)-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1=NC=CN1 GTIYLLQEFVPNTN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 150000003857 carboxamides Chemical class 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 206010061218 Inflammation Diseases 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- CAJDUBMUXJAMBC-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-phenyl-1H-imidazole Chemical compound FC1=CC=C(C=C1)C=1NC=C(N=1)C1=CC=CC=C1 CAJDUBMUXJAMBC-UHFFFAOYSA-N 0.000 description 1
- DUDHBDTXXSEUDX-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)-1h-imidazole Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1C1=NC=CN1 DUDHBDTXXSEUDX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241001390674 Gnaphalium uliginosum Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241000656145 Thyrsites atun Species 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- JWSVYLWYZNJFJQ-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-1h-imidazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CN=C1C1=CC=C(F)C=C1 JWSVYLWYZNJFJQ-UHFFFAOYSA-N 0.000 description 1
- REHWUNLYJRAKRU-UHFFFAOYSA-N ethyl 4-amino-2-(4-fluorophenyl)-1H-imidazole-5-carboxylate Chemical compound NC1=C(N=C(N1)C1=CC=C(C=C1)F)C(=O)OCC REHWUNLYJRAKRU-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3871671A GB1378381A (en) | 1971-08-18 | 1971-08-18 | Imidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2200499A1 true DE2200499A1 (de) | 1973-03-08 |
Family
ID=10405251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722200499 Pending DE2200499A1 (de) | 1971-08-18 | 1972-01-05 | 2-phenyl-5-amino-imidazole, ihre pharmakologisch vertraeglichen salze, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende antiphlogistische arzneipraeparate |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4829771A (https=) |
| BE (1) | BE777738A (https=) |
| CH (1) | CH584203A5 (https=) |
| DE (1) | DE2200499A1 (https=) |
| ES (1) | ES398587A1 (https=) |
| FR (1) | FR2149329B1 (https=) |
| GB (1) | GB1378381A (https=) |
| IL (1) | IL38357A (https=) |
| NL (1) | NL7200080A (https=) |
| SE (1) | SE376418B (https=) |
| ZA (1) | ZA7238B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4197596A1 (en) * | 2021-12-15 | 2023-06-21 | Eberhard Karls Universität Tübingen Medizinische Fakultät | Imidazole derivatives for the treatment and prophylaxis of infectious diseases |
-
1971
- 1971-08-18 GB GB3871671A patent/GB1378381A/en not_active Expired
- 1971-12-14 IL IL38357A patent/IL38357A/en unknown
- 1971-12-16 SE SE7116177A patent/SE376418B/xx unknown
- 1971-12-31 JP JP47004138A patent/JPS4829771A/ja active Pending
-
1972
- 1972-01-04 ES ES398587A patent/ES398587A1/es not_active Expired
- 1972-01-04 NL NL7200080A patent/NL7200080A/xx unknown
- 1972-01-04 FR FR7200104A patent/FR2149329B1/fr not_active Expired
- 1972-01-04 ZA ZA720038A patent/ZA7238B/xx unknown
- 1972-01-05 DE DE19722200499 patent/DE2200499A1/de active Pending
- 1972-01-05 BE BE777738A patent/BE777738A/xx unknown
- 1972-01-05 CH CH13772A patent/CH584203A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1378381A (en) | 1974-12-27 |
| CH584203A5 (https=) | 1977-01-31 |
| ZA7238B (en) | 1972-09-27 |
| NL7200080A (https=) | 1973-02-20 |
| JPS4829771A (https=) | 1973-04-19 |
| SE376418B (https=) | 1975-05-26 |
| BE777738A (fr) | 1972-07-05 |
| ES398587A1 (es) | 1974-09-16 |
| FR2149329A1 (https=) | 1973-03-30 |
| IL38357A (en) | 1976-08-31 |
| FR2149329B1 (https=) | 1975-12-26 |
| IL38357A0 (en) | 1972-02-29 |
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