SU474145A3 - Способ получени производных имидазолина - Google Patents
Способ получени производных имидазолинаInfo
- Publication number
- SU474145A3 SU474145A3 SU1742351A SU1742351A SU474145A3 SU 474145 A3 SU474145 A3 SU 474145A3 SU 1742351 A SU1742351 A SU 1742351A SU 1742351 A SU1742351 A SU 1742351A SU 474145 A3 SU474145 A3 SU 474145A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- furan
- salt
- methyl
- alkyl
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000002462 imidazolines Chemical class 0.000 title 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 241001415513 Salpida Species 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- TVMUHOAONWHJBV-UHFFFAOYSA-M dehydroglycinate Chemical compound [O-]C(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB332771 | 1971-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU474145A3 true SU474145A3 (ru) | 1975-06-14 |
Family
ID=9756227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1742351A SU474145A3 (ru) | 1971-01-27 | 1972-01-27 | Способ получени производных имидазолина |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3818035A (enExample) |
| JP (1) | JPS4938273B1 (enExample) |
| AT (1) | AT311336B (enExample) |
| BE (1) | BE777689A (enExample) |
| CA (1) | CA962273A (enExample) |
| CH (1) | CH535254A (enExample) |
| DE (1) | DE2203373C3 (enExample) |
| DK (1) | DK138496B (enExample) |
| FI (1) | FI55841C (enExample) |
| GB (1) | GB1333471A (enExample) |
| HU (1) | HU162823B (enExample) |
| NL (1) | NL150454B (enExample) |
| NO (1) | NO134115C (enExample) |
| SE (1) | SE378426B (enExample) |
| SU (1) | SU474145A3 (enExample) |
| YU (1) | YU34694B (enExample) |
| ZA (1) | ZA72286B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927023A (en) * | 1974-05-24 | 1975-12-16 | Warner Lambert Co | Imidazolyl benzofurans |
| DE3049542A1 (de) * | 1980-12-31 | 1982-07-29 | Basf Ag, 6700 Ludwigshafen | Azolylalkyl-2,3-dihydrobenzofurane, diese enthaltende fungizide und verfahren zu ihrer herstellung |
| ZA825413B (en) * | 1981-08-26 | 1983-06-29 | Pfizer | Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them |
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| WO1999032482A1 (en) * | 1997-12-19 | 1999-07-01 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| US7777035B2 (en) * | 2005-06-22 | 2010-08-17 | Chemocentryx, Inc. | Azaindazole compounds and methods of use |
| CA2637312A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of substituted 2-imidazole of imidazoline derivatives |
| CA2666762C (en) * | 2006-10-19 | 2014-12-30 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| WO2008046756A1 (en) * | 2006-10-19 | 2008-04-24 | F. Hoffmann-La Roche Ag | Aminomethyl-2-imidazoles with affinity with the trace amine associated receptors |
| EP2086959B1 (en) * | 2006-11-02 | 2011-11-16 | F. Hoffmann-La Roche AG | Substituted 2-imidazoles as modulators of the trace amine associated receptors |
| MX2009005047A (es) * | 2006-11-16 | 2009-05-25 | Hoffmann La Roche | 4-imidazoles sustituidos. |
| MX2009005920A (es) * | 2006-12-13 | 2009-06-16 | Hoffmann La Roche | Nuevos 2-imidazoles como ligandos para receptores asociados con trazas de amina. |
| US20080146523A1 (en) | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| MX2009008255A (es) * | 2007-02-02 | 2009-08-12 | Hoffmann La Roche | Nuevas 2-aminooxazolinas como ligandos taar1. |
| KR101222412B1 (ko) * | 2007-02-15 | 2013-01-15 | 에프. 호프만-라 로슈 아게 | Ｔａａｒ1 리간드로서의 2-아미노옥사졸린 |
| CN101687812A (zh) | 2007-07-02 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | 对痕量胺相关受体(taar)具有良好亲和性的2-咪唑啉化合物 |
| WO2009003867A1 (en) * | 2007-07-03 | 2009-01-08 | F. Hoffmann-La Roche Ag | 4-imidazolines and their use as antidepressants |
| WO2009016048A1 (en) * | 2007-07-27 | 2009-02-05 | F. Hoffmann-La Roche Ag | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
| CN101765425A (zh) * | 2007-08-02 | 2010-06-30 | 弗·哈夫曼-拉罗切有限公司 | 苯甲酰胺衍生物用于治疗cns障碍的用途 |
| BRPI0814758A2 (pt) * | 2007-08-03 | 2015-03-03 | Hoffmann La Roche | Piridinacarboxamida e derivados de benzamida como ligantes taar1 |
| CN102083805A (zh) * | 2008-07-24 | 2011-06-01 | 弗·哈夫曼-拉罗切有限公司 | 4,5-二氢-唑-2-基衍生物 |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| US20100311798A1 (en) * | 2009-06-05 | 2010-12-09 | Decoret Guillaume | 2-aminooxazolines as taar1 ligands |
| US8354441B2 (en) * | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| JP6814814B2 (ja) | 2016-03-17 | 2021-01-20 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｔａａｒのアゴニストとしての活性を有する５−エチル−４−メチル−ピラゾール−３−カルボキサミド誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1121054B (de) * | 1960-11-23 | 1962-01-04 | Merck Ag E | Verfahren zur Herstellung eines neuen Imidazolinderivates und dessen Saeureadditionssalzen |
-
1971
- 1971-01-27 GB GB332771A patent/GB1333471A/en not_active Expired
-
1972
- 1972-01-05 BE BE777689A patent/BE777689A/xx not_active IP Right Cessation
- 1972-01-06 CH CH17272A patent/CH535254A/fr not_active IP Right Cessation
- 1972-01-10 US US00216795A patent/US3818035A/en not_active Expired - Lifetime
- 1972-01-17 ZA ZA720286A patent/ZA72286B/xx unknown
- 1972-01-25 DE DE2203373A patent/DE2203373C3/de not_active Expired
- 1972-01-26 DK DK34572AA patent/DK138496B/da unknown
- 1972-01-26 HU HULA791A patent/HU162823B/hu not_active IP Right Cessation
- 1972-01-26 NO NO192/72A patent/NO134115C/no unknown
- 1972-01-26 SE SE7200867A patent/SE378426B/xx unknown
- 1972-01-26 YU YU181/72A patent/YU34694B/xx unknown
- 1972-01-27 CA CA133,337A patent/CA962273A/en not_active Expired
- 1972-01-27 FI FI219/72A patent/FI55841C/fi active
- 1972-01-27 NL NL727201121A patent/NL150454B/xx not_active IP Right Cessation
- 1972-01-27 SU SU1742351A patent/SU474145A3/ru active
- 1972-01-27 JP JP47010207A patent/JPS4938273B1/ja active Pending
- 1972-01-27 AT AT64772A patent/AT311336B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE777689A (fr) | 1972-07-05 |
| ZA72286B (en) | 1972-09-27 |
| JPS4938273B1 (enExample) | 1974-10-16 |
| AU3817772A (en) | 1973-07-26 |
| YU34694B (en) | 1979-12-31 |
| SE378426B (enExample) | 1975-09-01 |
| YU18172A (en) | 1979-07-10 |
| AT311336B (de) | 1973-11-12 |
| NL7201121A (enExample) | 1972-07-31 |
| NO134115B (enExample) | 1976-05-10 |
| DK138496B (da) | 1978-09-18 |
| DE2203373A1 (de) | 1972-08-17 |
| NL150454B (nl) | 1976-08-16 |
| NO134115C (enExample) | 1976-08-18 |
| DE2203373C3 (de) | 1978-04-13 |
| GB1333471A (en) | 1973-10-10 |
| DK138496C (enExample) | 1979-02-26 |
| DE2203373B2 (de) | 1977-08-11 |
| US3818035A (en) | 1974-06-18 |
| FI55841B (fi) | 1979-06-29 |
| HU162823B (enExample) | 1973-04-28 |
| FI55841C (fi) | 1979-10-10 |
| CA962273A (en) | 1975-02-04 |
| CH535254A (fr) | 1973-03-31 |
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