DE1545988C3 - - Google Patents
Info
- Publication number
- DE1545988C3 DE1545988C3 DE19651545988 DE1545988A DE1545988C3 DE 1545988 C3 DE1545988 C3 DE 1545988C3 DE 19651545988 DE19651545988 DE 19651545988 DE 1545988 A DE1545988 A DE 1545988A DE 1545988 C3 DE1545988 C3 DE 1545988C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- imidazole
- filtered
- added
- ethyl
- 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
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1H-imidazol-1-ium-4-carboxylate Chemical class OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- -1 imidazole-5-carboxylic acid halide Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1H-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-Phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1H-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WXWUKJOVARUSTN-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydroimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CNC(=S)N1 WXWUKJOVARUSTN-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N Pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- DVLGIQNHKLWSRU-UHFFFAOYSA-N methyl 1H-imidazole-5-carboxylate Chemical compound COC(=O)C1=CN=CN1 DVLGIQNHKLWSRU-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000006748 scratching Methods 0.000 description 2
- 230000002393 scratching Effects 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229940025084 Amphetamine Drugs 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N Ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229940005535 HYPNOTICS AND SEDATIVES Drugs 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010028334 Muscle spasms Diseases 0.000 description 1
- 241000283898 Ovis Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 229940066715 Pentylenetetrazole Drugs 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M Potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039911 Seizure Diseases 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229960002734 amfetamine Drugs 0.000 description 1
- 230000003042 antagnostic Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 230000000147 hypnotic Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035812 respiration Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 229940066769 systemic antihistamines Substituted alkylamines Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US360441A US3354173A (en) | 1964-04-16 | 1964-04-16 | Imidazole carboxylates |
| US36044164 | 1964-04-16 | ||
| DEJ0027907 | 1965-04-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1545988A1 DE1545988A1 (de) | 1970-01-29 |
| DE1545988B2 DE1545988B2 (de) | 1976-01-29 |
| DE1545988C3 true DE1545988C3 (es) | 1976-09-16 |
Family
ID=23417963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545988 Granted DE1545988B2 (de) | 1964-04-16 | 1965-04-14 | 5-imidazolcarbonsaeureester und verfahren zu ihrer herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3354173A (es) |
| BE (1) | BE662474A (es) |
| DE (1) | DE1545988B2 (es) |
| FR (2) | FR1604115A (es) |
| GB (1) | GB1064531A (es) |
| SE (1) | SE327708B (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1475271A (en) * | 1975-04-30 | 1977-06-01 | Pfizer Ltd | 1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents |
| DE2732531A1 (de) * | 1977-07-19 | 1979-02-01 | Hoechst Ag | Imidazolcarbonsaeuren und deren derivate |
| JPS54148788A (en) * | 1978-05-15 | 1979-11-21 | Takeda Chem Ind Ltd | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation |
| GR64915B (en) * | 1978-09-14 | 1980-06-09 | Janssen Pharmaceutica Nv | Improved etomidate-containing compositions |
| JPS5671073A (en) * | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | Imidazole derivative |
| US4770689A (en) * | 1986-03-10 | 1988-09-13 | Janssen Pharmaceutica N.V. | Herbicidal imidazole-5-carboxylic acid derivatives |
| GB8631020D0 (en) * | 1986-12-30 | 1987-02-04 | Janssen Pharmaceutica Nv | 1-methyl-1h-imidazole-5-carboxylic acid derivatives |
| US6878735B2 (en) * | 2002-05-31 | 2005-04-12 | Board Of Trustees Of Michigan State University | Multi-substituted imidazolines and method of use thereof |
| EP2149550A4 (en) | 2007-04-27 | 2010-08-11 | Takeda Pharmaceutical | HETEROCYCLIC COMPOUND WITH FIVE NITROGEN CHAINS |
| AU2013242865B2 (en) * | 2008-03-31 | 2016-05-26 | The General Hospital Corporation | Etomidate analogues with improved pharmacokinetic and pharmacodynamic properties |
| MX2010010675A (es) * | 2008-03-31 | 2010-11-25 | Gen Hospital Corp | Analogos de etomidato con propiedades farmacocineticas y farmacodinamicas mejoradas. |
| CN102548964B (zh) | 2009-07-10 | 2014-09-24 | 通用医疗公司 | 不抑制肾上腺皮质类固醇合成的依托咪酯类似物 |
| DK2802325T3 (en) | 2012-01-13 | 2017-03-13 | Massachusetts Gen Hospital | ANESTHETIC RELATIONS AND RELATED APPLICATIONS THEREOF |
| CN103739553B (zh) * | 2013-12-23 | 2014-11-12 | 四川大学华西医院 | 含有醚侧链的n-取代咪唑羧酸酯手性化合物、制备方法和用途 |
| CN109776512A (zh) * | 2018-01-30 | 2019-05-21 | 成都安诺晨创医药科技有限公司 | 一种n-取代咪唑甲酸酯类衍生物及其用途 |
| CN112375039B (zh) * | 2020-11-20 | 2022-03-08 | 燃点(南京)生物医药科技有限公司 | (r)-(+)-1-(1-苯乙基)-2-巯基咪唑-5-羧酸乙酯新晶型a及制备方法 |
| CN113563266A (zh) * | 2021-07-28 | 2021-10-29 | 江西汇和化工有限公司 | 一种连续化合成咪鲜胺及其原药中间酰化物的工艺 |
| CN114292236A (zh) * | 2021-12-24 | 2022-04-08 | 江苏慈星药业有限公司 | 一种依托咪酯中间体的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1184709A (fr) * | 1957-09-21 | 1959-07-24 | Cfmc | Nouveaux dérivés imidazoliques, utilisables comme agents de protection contre les rayons ultra-violets et leurs procédés de fabrication |
-
1964
- 1964-04-16 US US360441A patent/US3354173A/en not_active Expired - Lifetime
-
1965
- 1965-03-25 GB GB12665/65A patent/GB1064531A/en not_active Expired
- 1965-04-14 DE DE19651545988 patent/DE1545988B2/de active Granted
- 1965-04-14 BE BE662474D patent/BE662474A/xx unknown
- 1965-04-14 SE SE04963/65A patent/SE327708B/xx unknown
- 1965-04-15 FR FR1604115D patent/FR1604115A/fr not_active Expired
- 1965-07-12 FR FR24367A patent/FR4499M/fr not_active Expired
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