GB1222397A - Process for the preparation of phenethylamine salts - Google Patents
Process for the preparation of phenethylamine saltsInfo
- Publication number
- GB1222397A GB1222397A GB7600/68A GB760068A GB1222397A GB 1222397 A GB1222397 A GB 1222397A GB 7600/68 A GB7600/68 A GB 7600/68A GB 760068 A GB760068 A GB 760068A GB 1222397 A GB1222397 A GB 1222397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydrochloride
- hydrogen
- chloroethyl
- phenethylamine
- 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
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 title abstract 3
- -1 3- to 7- membered cycloalkyl radical Chemical class 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001541 aziridines Chemical class 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Chemical group 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 229940048346 phenethylamine hydrochloride Drugs 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- WIBADEXUNPVVIP-UHFFFAOYSA-N n-methyl-2-phenylethanamine;hydrochloride Chemical compound Cl.CNCCC1=CC=CC=C1 WIBADEXUNPVVIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Drawers Of Furniture (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238667A CH481110A (de) | 1967-02-17 | 1967-02-17 | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| CH1167167A CH488705A (de) | 1967-02-17 | 1967-08-18 | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1222397A true GB1222397A (en) | 1971-02-10 |
Family
ID=25690322
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7601/68A Expired GB1221324A (en) | 1967-02-17 | 1968-02-16 | New processes for the production of benzazepine derivatives |
| GB7600/68A Expired GB1222397A (en) | 1967-02-17 | 1968-02-16 | Process for the preparation of phenethylamine salts |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7601/68A Expired GB1221324A (en) | 1967-02-17 | 1968-02-16 | New processes for the production of benzazepine derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3652543A (enExample) |
| AT (1) | AT275533B (enExample) |
| BE (1) | BE710872A (enExample) |
| CH (2) | CH481110A (enExample) |
| DE (2) | DE1695124A1 (enExample) |
| DK (1) | DK115473B (enExample) |
| ES (1) | ES350574A1 (enExample) |
| FR (2) | FR1561479A (enExample) |
| GB (2) | GB1221324A (enExample) |
| IL (1) | IL29485A (enExample) |
| NL (1) | NL6802257A (enExample) |
| NO (1) | NO124369B (enExample) |
| SE (1) | SE342043B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT289812B (de) * | 1968-08-09 | 1971-05-10 | Geigy Ag J R | Verfahren zur Herstellung des neuen 2-Methyl-7-chlor-2,3,4,5-tetrahydro-1H-3-benzazepins sowie seiner Säureadditionssalze |
| DE2016136A1 (de) * | 1970-04-04 | 1971-10-14 | C H Boehnnger Sohn, 6507 Ingel heim | Neue 7 Acyl 1,2,4,5 tetrahydro (3H) 3 benzazepine |
| DE2143204C3 (de) * | 1971-08-28 | 1979-09-27 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | N-Fluoralkyl-phenylisopropylamin-Derivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis |
| DE2207430C3 (de) * | 1972-02-14 | 1982-05-13 | Pennwalt Corp., 19102 Philadelphia, Pa. | 1,2,4,5-Tetrahydro-3H-3-benzazepin, ein Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Mittel |
| DE3272044D1 (de) * | 1981-11-27 | 1986-08-21 | Smithkline Beckman Corp | 3-benzazepines as alpha-2 antagonists |
| US4541954A (en) * | 1984-09-05 | 1985-09-17 | Smithkline Beckman Corporation | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| WO1987004430A2 (en) * | 1986-01-16 | 1987-07-30 | Schering Corporation | Fused benzazepines |
| US4973586A (en) * | 1986-01-16 | 1990-11-27 | Schering Corporation | Fused benzazepines, compositions of, and medical use thereof |
| US5302716A (en) * | 1986-01-16 | 1994-04-12 | Schering Corporation | Fused benzazepines |
| US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| ATE78467T1 (de) * | 1987-07-15 | 1992-08-15 | Schering Corp | Kondensierte benzazepine. |
| EP0513174B1 (en) * | 1990-02-02 | 1995-08-16 | Schering Corporation | 4,5-cycloalkano-3-benzazepin-7-ol-derivatives and their use |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| US20030220661A1 (en) * | 2002-05-21 | 2003-11-27 | Heartstent Corporation | Transmyocardial implant delivery system |
| CN1805938B (zh) * | 2003-06-17 | 2010-06-16 | 艾尼纳制药公司 | 用于治疗5ht2c受体相关疾病的苯并氮杂卓衍生物 |
| EP2332921B1 (en) | 2003-06-17 | 2016-03-02 | Arena Pharmaceuticals, Inc. | 8-Chloro-1 -methyl-2,3,4,5-tetrahydro-1 H-3benzazapine Hydrochloride |
| WO2005042491A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| WO2005042490A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| NZ589756A (en) | 2004-12-21 | 2012-05-25 | Arena Pharm Inc | Method for the preparation of crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| WO2006071740A2 (en) | 2004-12-23 | 2006-07-06 | Arena Pharmaceuticals, Inc. | 5ht2c receptor modulator compositions and methods of use |
| CN101466684B (zh) | 2006-04-03 | 2012-06-20 | 艾尼纳制药公司 | 8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的制备工艺和其相关中间体 |
| CA2670285A1 (en) * | 2006-12-05 | 2008-06-12 | Arena Pharmaceuticals, Inc. | Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof |
| EP2288585A1 (en) * | 2008-03-04 | 2011-03-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| EP2443080A2 (en) | 2009-06-18 | 2012-04-25 | Arena Pharmaceuticals, Inc. | Process for the preparation of 5-ht2c receptor agonists |
| EP2510949A4 (en) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| EP2611433A2 (en) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-ht2c agonists |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| WO2012030939A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| EP3485878A1 (en) | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| JP2015534563A (ja) | 2012-10-09 | 2015-12-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 体重管理の方法 |
-
1967
- 1967-02-17 CH CH238667A patent/CH481110A/de not_active IP Right Cessation
- 1967-08-18 CH CH1167167A patent/CH488705A/de not_active IP Right Cessation
-
1968
- 1968-02-15 US US705612A patent/US3652543A/en not_active Expired - Lifetime
- 1968-02-16 GB GB7601/68A patent/GB1221324A/en not_active Expired
- 1968-02-16 FR FR1561479D patent/FR1561479A/fr not_active Expired
- 1968-02-16 DE DE19681695124 patent/DE1695124A1/de active Pending
- 1968-02-16 GB GB7600/68A patent/GB1222397A/en not_active Expired
- 1968-02-16 FR FR1560654D patent/FR1560654A/fr not_active Expired
- 1968-02-16 AT AT148868A patent/AT275533B/de active
- 1968-02-16 DK DK63068AA patent/DK115473B/da unknown
- 1968-02-16 NO NO0598/68A patent/NO124369B/no unknown
- 1968-02-16 SE SE2047/68A patent/SE342043B/xx unknown
- 1968-02-16 IL IL29485A patent/IL29485A/xx unknown
- 1968-02-16 BE BE710872D patent/BE710872A/xx unknown
- 1968-02-16 ES ES350574A patent/ES350574A1/es not_active Expired
- 1968-02-16 DE DE19681668915 patent/DE1668915A1/de active Pending
- 1968-02-16 NL NL6802257A patent/NL6802257A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1560654A (enExample) | 1969-03-21 |
| AT275533B (de) | 1969-10-27 |
| GB1221324A (en) | 1971-02-03 |
| ES350574A1 (es) | 1969-11-16 |
| DE1695124A1 (de) | 1970-08-20 |
| CH488705A (de) | 1970-04-15 |
| IL29485A (en) | 1971-07-28 |
| NO124369B (enExample) | 1972-04-10 |
| FR1561479A (enExample) | 1969-03-28 |
| DE1668915A1 (de) | 1972-03-09 |
| NL6802257A (enExample) | 1968-08-19 |
| DK115473B (da) | 1969-10-13 |
| US3652543A (en) | 1972-03-28 |
| SE342043B (enExample) | 1972-01-24 |
| CH481110A (de) | 1969-11-15 |
| BE710872A (enExample) | 1968-08-16 |
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