FI62292C - Foerfarande foer framstaellning av optiskt aktiva laegre-alkyl-1-(1-fenyletyl)-1h-imidazol-5-karboxylater - Google Patents
Foerfarande foer framstaellning av optiskt aktiva laegre-alkyl-1-(1-fenyletyl)-1h-imidazol-5-karboxylater Download PDFInfo
- Publication number
- FI62292C FI62292C FI760601A FI760601A FI62292C FI 62292 C FI62292 C FI 62292C FI 760601 A FI760601 A FI 760601A FI 760601 A FI760601 A FI 760601A FI 62292 C FI62292 C FI 62292C
- Authority
- FI
- Finland
- Prior art keywords
- imidazole
- carboxylate
- alkyl
- phenylethyl
- phenyl
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title description 2
- 235000013399 edible fruits Nutrition 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RGYCCBLTSWHXIS-UHFFFAOYSA-N 3-(1-phenylethyl)imidazole-4-carboxylic acid Chemical compound C1=NC=C(C(O)=O)N1C(C)C1=CC=CC=C1 RGYCCBLTSWHXIS-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003326 hypnotic agent Substances 0.000 description 2
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- LKGPZAQFNYKISK-UHFFFAOYSA-N propoxate Chemical compound CCCOC(=O)C1=CN=CN1C(C)C1=CC=CC=C1 LKGPZAQFNYKISK-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 1
- NKWCGTOZTHZDHB-UHFFFAOYSA-M 1h-imidazole-5-carboxylate Chemical compound [O-]C(=O)C1=CN=CN1 NKWCGTOZTHZDHB-UHFFFAOYSA-M 0.000 description 1
- BYNPANNGSUKJAH-UHFFFAOYSA-N 3-(2-phenylethyl)imidazole-4-carboxylic acid Chemical compound OC(=O)C1=CN=CN1CCC1=CC=CC=C1 BYNPANNGSUKJAH-UHFFFAOYSA-N 0.000 description 1
- DNJHKDQBFMIVNV-CQSZACIVSA-N C(C)[C@](C1=CC=CC=C1)(N1C=NC(=C1)C(=O)O)C Chemical compound C(C)[C@](C1=CC=CC=C1)(N1C=NC(=C1)C(=O)O)C DNJHKDQBFMIVNV-CQSZACIVSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- -1 alkyl 1- (1-phenylethyl) -1H-imidazole-5-carboxylates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229950005930 propoxate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55719475A | 1975-03-10 | 1975-03-10 | |
| US55719475 | 1975-03-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760601A7 FI760601A7 (da) | 1976-09-11 |
| FI62292B FI62292B (fi) | 1982-08-31 |
| FI62292C true FI62292C (fi) | 1982-12-10 |
Family
ID=24224401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760601A FI62292C (fi) | 1975-03-10 | 1976-03-09 | Foerfarande foer framstaellning av optiskt aktiva laegre-alkyl-1-(1-fenyletyl)-1h-imidazol-5-karboxylater |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS51115473A (da) |
| AT (1) | AT353262B (da) |
| AU (1) | AU503733B2 (da) |
| BE (1) | BE839120A (da) |
| BG (1) | BG24806A3 (da) |
| CA (1) | CA1066709A (da) |
| CH (1) | CH629192A5 (da) |
| CS (1) | CS203116B2 (da) |
| DE (1) | DE2609573A1 (da) |
| DK (1) | DK99376A (da) |
| ES (1) | ES445450A1 (da) |
| FI (1) | FI62292C (da) |
| FR (1) | FR2318159A1 (da) |
| GB (1) | GB1535566A (da) |
| HU (1) | HU172026B (da) |
| IE (1) | IE42652B1 (da) |
| IL (1) | IL49190A (da) |
| IT (1) | IT1057941B (da) |
| LU (1) | LU74503A1 (da) |
| NL (1) | NL7602444A (da) |
| NO (1) | NO144884C (da) |
| PL (1) | PL99926B1 (da) |
| PT (1) | PT64879B (da) |
| SE (1) | SE7601959L (da) |
| SU (1) | SU677656A3 (da) |
| YU (1) | YU60876A (da) |
| ZA (1) | ZA761427B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE871675A (fr) * | 1977-12-02 | 1979-04-30 | Smithkline Corp | Procede de preparation de derives de l'imidazole |
| JPS5671073A (en) | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | Imidazole derivative |
| JPS5671074A (en) | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative |
| JPS58157768A (ja) * | 1982-03-16 | 1983-09-19 | Takeda Chem Ind Ltd | ４−クロロ−２−フエニルイミダゾ−ル−５−酢酸誘導体 |
| PL149675B1 (pl) * | 1986-03-10 | 1990-03-31 | Sposób wytwarzania nowych pochodnych kwasu 1-metyl0-1h-imidaz0l0karb0ksyl0weg0-5 | |
| RU2144022C1 (ru) * | 1995-10-30 | 2000-01-10 | Такеда Кемикал Индастриз, Лтд. | Эфиры n-(бифенилметил)аминобензойной кислоты и способ их получения |
| EP3210976A1 (en) | 2008-03-31 | 2017-08-30 | The General Hospital Corporation | Etomidate analogues with improved pharmacokinetic and pharmacodynamic properties |
| SI2802325T1 (sl) | 2012-01-13 | 2017-04-26 | The General Hospital Corporation | Anestetične spojine in pripadajoči postopki za uporabo |
-
1976
- 1976-02-13 CA CA245,697A patent/CA1066709A/en not_active Expired
- 1976-02-18 GB GB6339/76A patent/GB1535566A/en not_active Expired
- 1976-02-19 SE SE7601959A patent/SE7601959L/xx not_active Application Discontinuation
- 1976-02-23 ES ES445450A patent/ES445450A1/es not_active Expired
- 1976-03-01 FR FR7605762A patent/FR2318159A1/fr active Granted
- 1976-03-03 BE BE164793A patent/BE839120A/xx not_active IP Right Cessation
- 1976-03-05 CH CH280676A patent/CH629192A5/de not_active IP Right Cessation
- 1976-03-08 LU LU74503A patent/LU74503A1/xx unknown
- 1976-03-08 DE DE19762609573 patent/DE2609573A1/de not_active Withdrawn
- 1976-03-08 DK DK99376*#A patent/DK99376A/da not_active Application Discontinuation
- 1976-03-08 IT IT48460/76A patent/IT1057941B/it active
- 1976-03-08 JP JP51024280A patent/JPS51115473A/ja active Pending
- 1976-03-08 NO NO760790A patent/NO144884C/no unknown
- 1976-03-08 CS CS761495A patent/CS203116B2/cs unknown
- 1976-03-09 AT AT171776A patent/AT353262B/de not_active IP Right Cessation
- 1976-03-09 YU YU00608/76A patent/YU60876A/xx unknown
- 1976-03-09 HU HU76JA00000750A patent/HU172026B/hu unknown
- 1976-03-09 PT PT64879A patent/PT64879B/pt unknown
- 1976-03-09 IE IE482/76A patent/IE42652B1/en unknown
- 1976-03-09 NL NL7602444A patent/NL7602444A/xx not_active Application Discontinuation
- 1976-03-09 ZA ZA761427A patent/ZA761427B/xx unknown
- 1976-03-09 AU AU11806/76A patent/AU503733B2/en not_active Expired
- 1976-03-09 FI FI760601A patent/FI62292C/fi not_active IP Right Cessation
- 1976-03-10 IL IL49190A patent/IL49190A/xx unknown
- 1976-03-10 BG BG032575A patent/BG24806A3/xx unknown
- 1976-03-10 SU SU762329945A patent/SU677656A3/ru active
- 1976-03-10 PL PL1976187827A patent/PL99926B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU503733B2 (en) | 1979-09-20 |
| BE839120A (nl) | 1976-09-03 |
| CH629192A5 (en) | 1982-04-15 |
| IT1057941B (it) | 1982-03-30 |
| GB1535566A (en) | 1978-12-13 |
| HU172026B (hu) | 1978-05-28 |
| BG24806A3 (bg) | 1978-05-12 |
| SU677656A3 (ru) | 1979-07-30 |
| PL99926B1 (pl) | 1978-08-31 |
| NO144884B (no) | 1981-08-24 |
| NL7602444A (nl) | 1976-09-14 |
| NO760790L (da) | 1976-09-13 |
| AU1180676A (en) | 1977-09-15 |
| IE42652L (en) | 1976-09-10 |
| FR2318159B1 (da) | 1979-07-27 |
| CA1066709A (en) | 1979-11-20 |
| ATA171776A (de) | 1979-04-15 |
| FR2318159A1 (fr) | 1977-02-11 |
| IE42652B1 (en) | 1980-09-24 |
| IL49190A0 (en) | 1976-05-31 |
| LU74503A1 (da) | 1976-09-01 |
| AT353262B (de) | 1979-11-12 |
| FI62292B (fi) | 1982-08-31 |
| PT64879A (en) | 1976-04-01 |
| YU60876A (en) | 1983-01-21 |
| FI760601A7 (da) | 1976-09-11 |
| PT64879B (en) | 1978-02-06 |
| DE2609573A1 (de) | 1976-09-30 |
| ES445450A1 (es) | 1977-10-16 |
| NO144884C (no) | 1981-12-02 |
| DK99376A (da) | 1976-09-11 |
| IL49190A (en) | 1980-07-31 |
| SE7601959L (sv) | 1976-09-13 |
| ZA761427B (en) | 1977-10-26 |
| JPS51115473A (en) | 1976-10-12 |
| CS203116B2 (en) | 1981-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: JANSSEN PHARMACEUTICA N.V. |