GB951989A - A new imidazoline derivative and its acid addition salts and processes for their manufacture - Google Patents
A new imidazoline derivative and its acid addition salts and processes for their manufactureInfo
- Publication number
- GB951989A GB951989A GB41815/61A GB4181561A GB951989A GB 951989 A GB951989 A GB 951989A GB 41815/61 A GB41815/61 A GB 41815/61A GB 4181561 A GB4181561 A GB 4181561A GB 951989 A GB951989 A GB 951989A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylbenzothienyl
- ethylene diamine
- processes
- addition salts
- acid
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000002462 imidazolines Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- BLZKSRBAQDZAIX-UHFFFAOYSA-N 2-methyl-1-benzothiophene Chemical compound C1=CC=C2SC(C)=CC2=C1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- DYXSRRSEVMRNPQ-UHFFFAOYSA-N 3-(chloromethyl)-2-methyl-1-benzothiophene Chemical compound C1=CC=C2C(CCl)=C(C)SC2=C1 DYXSRRSEVMRNPQ-UHFFFAOYSA-N 0.000 abstract 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000001802 infusion Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000002504 physiological saline solution Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by 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 |
|---|---|---|---|
| DEM47194A DE1121054B (de) | 1960-11-23 | 1960-11-23 | Verfahren zur Herstellung eines neuen Imidazolinderivates und dessen Saeureadditionssalzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB951989A true GB951989A (en) | 1964-03-11 |
Family
ID=7305839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41815/61A Expired GB951989A (en) | 1960-11-23 | 1961-11-22 | A new imidazoline derivative and its acid addition salts and processes for their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3161653A (https=) |
| CH (1) | CH446353A (https=) |
| DE (1) | DE1121054B (https=) |
| FR (1) | FR1614M (https=) |
| GB (1) | GB951989A (https=) |
| SE (1) | SE305877B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438995A (en) * | 1968-01-08 | 1969-04-15 | Melville Sahyun | Diazaheterocyclic substituted benz-oxaheterocyclic compounds |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595234A1 (de) * | 1965-04-27 | 1970-03-05 | Roehm & Haas Gmbh | Verfahren zur Herstellung oligomerer bzw. polymerer Amine |
| GB1333471A (en) * | 1971-01-27 | 1973-10-10 | Labaz | Imidazoline derivatives and process for preparing the same |
| US4978332A (en) * | 1987-09-28 | 1990-12-18 | Matrix Pharmaceutical, Inc. | Treatments employing vasoconstrictive substances in combination with cytotoxic agents for introduction into cellular lesion areas |
| EP0767675A4 (en) * | 1995-04-10 | 1998-08-05 | Baxter Int | USE OF CROSS-LINKED HEMOGLOBIN IN THE TREATMENT OF SUBARACHNOIDAL BLEEDING |
| EP0924209B1 (en) * | 1997-12-19 | 2003-05-02 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| CA2637312A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of substituted 2-imidazole of imidazoline derivatives |
| RU2009112496A (ru) * | 2006-10-19 | 2010-11-27 | Ф. Хоффманн-Ля Рош Аг (Ch) | Аминометил-4-имидазолы |
| AU2007312389B2 (en) * | 2006-10-19 | 2012-02-23 | F. Hoffmann-La Roche Ag | Aminomethyl-2-imidazoles with affinity with the trace amine associated receptors |
| CA2668454A1 (en) * | 2006-11-02 | 2008-05-08 | F. Hoffmann-La Roche Ag | Substituted 2-imidazoles |
| JP2010510184A (ja) * | 2006-11-16 | 2010-04-02 | エフ．ホフマン−ラ ロシュ アーゲー | 置換４−イミダゾール類 |
| CA2672617A1 (en) * | 2006-12-13 | 2008-06-19 | F. Hoffmann-La Roche Ag | Novel 2-imidazoles as ligands for trace amine associated receptors (taar) |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| CN101600700B (zh) * | 2007-02-02 | 2013-08-21 | 弗·哈夫曼-拉罗切有限公司 | 作为taar1配体用于cns病症的新的2-氨基噁唑啉 |
| 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 |
| CA2691704A1 (en) * | 2007-07-03 | 2009-01-08 | F. Hoffmann-La Roche Ag | 4-imidazolines and their use as antidepressants |
| CA2694362A1 (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 |
| JP5341084B2 (ja) * | 2007-08-03 | 2013-11-13 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
| 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 |
| CN108713019B (zh) | 2016-03-17 | 2021-06-15 | 豪夫迈·罗氏有限公司 | 具有作为taar的激动剂的活性的5-乙基-4-甲基-吡唑-3-甲酰胺衍生物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965648A (en) * | 1960-12-20 | Certain i-alkenyl benzimidazoles | ||
| DE1049387B (de) * | 1959-01-29 | Ciba Aktiengesellschaft, Basel (Schweiz) | Verfahren zur Herstellung eines neuen Imidazolins | |
| US2441867A (en) * | 1943-11-19 | 1948-05-18 | Recip Ab | Methods of producing 2-(alpha-naphthylmethyl)-imidazoline |
| US2457047A (en) * | 1946-02-13 | 1948-12-21 | Monsanto Chemicals | 2-(2'-thenyl)-4, 5-dihydroimidazoles and process for making the same |
| US2780577A (en) * | 1951-05-26 | 1957-02-05 | Burroughs Wellcome Co | Inhibiting polymethylene diquaternary curariform activity by alpha-stilbazoline derivatives |
| US2744909A (en) * | 1955-06-27 | 1956-05-08 | Bristol Lab Inc | 2-(ortho-phenylbenzyl) imidazoline and acid addition salts |
| US3024248A (en) * | 1956-09-18 | 1962-03-06 | Ciba Pharm Prod Inc | Organic sulfur compounds and method for producing same |
| US2955073A (en) * | 1958-06-02 | 1960-10-04 | Burroughs Wellcome Co | Method of treating febrile convulsions |
| NL106045C (https=) * | 1958-09-02 | |||
| US3010972A (en) * | 1960-03-18 | 1961-11-28 | Smith Kline French Lab | Condensed cyclopropyl amine derivatives |
| US3042674A (en) * | 1960-07-12 | 1962-07-03 | Sahyun | Xanthene and thiaxanthene cyclic amidines |
-
1960
- 1960-11-23 DE DEM47194A patent/DE1121054B/de active Pending
-
1961
- 1961-10-25 CH CH1232461A patent/CH446353A/de unknown
- 1961-11-21 US US154053A patent/US3161653A/en not_active Expired - Lifetime
- 1961-11-22 FR FR879728A patent/FR1614M/fr active Active
- 1961-11-22 GB GB41815/61A patent/GB951989A/en not_active Expired
- 1961-11-22 SE SE11615/61A patent/SE305877B/xx unknown
-
1964
- 1964-09-09 US US395280A patent/US3238101A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438995A (en) * | 1968-01-08 | 1969-04-15 | Melville Sahyun | Diazaheterocyclic substituted benz-oxaheterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| SE305877B (https=) | 1968-11-11 |
| FR1614M (fr) | 1962-12-17 |
| US3238101A (en) | 1966-03-01 |
| US3161653A (en) | 1964-12-15 |
| DE1121054B (de) | 1962-01-04 |
| CH446353A (de) | 1967-11-15 |
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