NO853255L - Fremgangsmaate for fremstilling av 6-klor-n-metyl-2,3,4,5-tetrahydro-1h-3-benzazepin. - Google Patents
Fremgangsmaate for fremstilling av 6-klor-n-metyl-2,3,4,5-tetrahydro-1h-3-benzazepin.Info
- Publication number
- NO853255L NO853255L NO853255A NO853255A NO853255L NO 853255 L NO853255 L NO 853255L NO 853255 A NO853255 A NO 853255A NO 853255 A NO853255 A NO 853255A NO 853255 L NO853255 L NO 853255L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- benzazepine
- tetrahydro
- approx
- trichlorobenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 22
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 6
- RSRUDTPYRBLHEO-UHFFFAOYSA-N Benalfocin Chemical compound C1CN(C)CCC2=CC=CC(Cl)=C21 RSRUDTPYRBLHEO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000012071 phase Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AZYXRMVCBUOJSZ-UHFFFAOYSA-N 6-chloro-1-methyl-1-benzazepine;hydrochloride Chemical compound Cl.CN1C=CC=CC2=C(Cl)C=CC=C12 AZYXRMVCBUOJSZ-UHFFFAOYSA-N 0.000 description 1
- JKQKVNMNAIFCFS-UHFFFAOYSA-N 6-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepine;hydrochloride Chemical compound Cl.C1CN(C)CCC2=CC=CC(Cl)=C21 JKQKVNMNAIFCFS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 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
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/647,552 US4541954A (en) | 1984-09-05 | 1984-09-05 | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO853255L true NO853255L (no) | 1986-03-06 |
Family
ID=24597406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO853255A NO853255L (no) | 1984-09-05 | 1985-08-19 | Fremgangsmaate for fremstilling av 6-klor-n-metyl-2,3,4,5-tetrahydro-1h-3-benzazepin. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4541954A (fi) |
| EP (1) | EP0174118A3 (fi) |
| JP (1) | JPS6168469A (fi) |
| KR (1) | KR860002470A (fi) |
| AU (1) | AU581918B2 (fi) |
| CA (1) | CA1244017A (fi) |
| DK (1) | DK379985A (fi) |
| EG (1) | EG17149A (fi) |
| ES (1) | ES8609266A1 (fi) |
| FI (1) | FI853255L (fi) |
| GR (1) | GR852041B (fi) |
| HU (1) | HU194181B (fi) |
| IL (1) | IL76100A0 (fi) |
| NO (1) | NO853255L (fi) |
| NZ (1) | NZ213141A (fi) |
| PH (1) | PH20796A (fi) |
| PT (1) | PT81018B (fi) |
| ZA (1) | ZA856268B (fi) |
| ZW (1) | ZW13385A1 (fi) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993000811A1 (en) * | 1991-07-01 | 1993-01-21 | The General Hospital Corporation | Invertebrate phenylethanolamine transporter and the use thereof |
| CA2100678A1 (en) * | 1991-12-06 | 1993-06-07 | Hiroshi Kagawa | Film type battery and layer-built film type battery |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| HUE028976T2 (en) * | 2003-06-17 | 2017-02-28 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| EA016558B1 (ru) | 2003-06-17 | 2012-05-30 | Арена Фармасьютикалз, Инк. | Производные бензазепина, используемые для лечения заболеваний, ассоциированных с 5-ht-рецептором |
| JP5270167B2 (ja) | 2004-12-21 | 2013-08-21 | 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 | （ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンザゼピン塩酸塩の結晶形 |
| CN102631349A (zh) | 2004-12-23 | 2012-08-15 | 艾尼纳制药公司 | 5HT2c受体调节剂组合物和使用方法 |
| JP5199997B2 (ja) | 2006-04-03 | 2013-05-15 | 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 | ８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス |
| CN101547892B (zh) * | 2006-12-05 | 2014-08-20 | 艾尼纳制药公司 | 制备(r)-8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的方法和其中间体 |
| JP5491421B2 (ja) * | 2008-03-04 | 2014-05-14 | 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 | ５−ｈｔ２ｃアゴニストである（ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンに関連する中間体の調製のためのプロセス |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| WO2011153206A1 (en) | 2010-06-02 | 2011-12-08 | 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 |
| SG10201506870PA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Salts of lorcaserin with optically active acids |
| SG188362A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| US8999970B2 (en) | 2010-09-01 | 2015-04-07 | Arena Pharmaceuticals, Inc. | Administration of an anti-obesity compound to individuals with renal impairment |
| KR20150070249A (ko) | 2012-10-09 | 2015-06-24 | 아레나 파마슈티칼스, 인크. | 체중 관리 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1118688A (en) * | 1967-02-17 | 1968-07-03 | Scherico Ltd | Novel benzazepines and process for making same |
| CH481110A (de) * | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| US4251660A (en) * | 1978-08-10 | 1981-02-17 | Smithkline Corporation | Method for preparing tetrahydroisoquinolines |
| US4200754A (en) * | 1979-02-02 | 1980-04-29 | Smithkline Corporation | Method for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline |
| ZA827887B (en) * | 1981-11-27 | 1983-11-30 | Smithkline Beckman Corp | Pharmaceutical compositions and method of producing alpha2 antagonism |
| DE3272044D1 (de) * | 1981-11-27 | 1986-08-21 | Smithkline Beckman Corp | 3-benzazepines as alpha-2 antagonists |
| IE53962B1 (en) * | 1981-11-27 | 1989-04-26 | Smithkline Beckman Corp | 3-benzazepines as alpha-2 antagonists |
-
1984
- 1984-09-05 US US06/647,552 patent/US4541954A/en not_active Expired - Fee Related
-
1985
- 1985-08-14 EP EP85305780A patent/EP0174118A3/en not_active Ceased
- 1985-08-15 IL IL76100A patent/IL76100A0/xx unknown
- 1985-08-19 NZ NZ213141A patent/NZ213141A/xx unknown
- 1985-08-19 PH PH32660A patent/PH20796A/en unknown
- 1985-08-19 NO NO853255A patent/NO853255L/no unknown
- 1985-08-19 CA CA000488976A patent/CA1244017A/en not_active Expired
- 1985-08-19 ZA ZA856268A patent/ZA856268B/xx unknown
- 1985-08-20 ZW ZW133/85A patent/ZW13385A1/xx unknown
- 1985-08-20 ES ES546285A patent/ES8609266A1/es not_active Expired
- 1985-08-20 JP JP60183788A patent/JPS6168469A/ja active Pending
- 1985-08-21 HU HU853190A patent/HU194181B/hu unknown
- 1985-08-21 DK DK379985A patent/DK379985A/da not_active Application Discontinuation
- 1985-08-21 AU AU46481/85A patent/AU581918B2/en not_active Ceased
- 1985-08-22 GR GR852041A patent/GR852041B/el unknown
- 1985-08-22 KR KR1019850006061A patent/KR860002470A/ko not_active Application Discontinuation
- 1985-08-23 PT PT81018A patent/PT81018B/pt unknown
- 1985-08-23 FI FI853255A patent/FI853255L/fi not_active Application Discontinuation
- 1985-09-04 EG EG545/85A patent/EG17149A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0174118A2 (en) | 1986-03-12 |
| PT81018A (en) | 1985-09-01 |
| AU581918B2 (en) | 1989-03-09 |
| ZA856268B (en) | 1986-07-30 |
| ES8609266A1 (es) | 1986-09-01 |
| HU194181B (en) | 1988-01-28 |
| ES546285A0 (es) | 1986-09-01 |
| IL76100A0 (en) | 1985-12-31 |
| ZW13385A1 (en) | 1985-11-20 |
| GR852041B (fi) | 1985-12-19 |
| PH20796A (en) | 1987-04-14 |
| NZ213141A (en) | 1988-07-28 |
| DK379985A (da) | 1986-03-06 |
| EG17149A (en) | 1989-06-30 |
| FI853255A0 (fi) | 1985-08-23 |
| KR860002470A (ko) | 1986-04-26 |
| HUT38617A (en) | 1986-06-30 |
| US4541954A (en) | 1985-09-17 |
| FI853255L (fi) | 1986-03-06 |
| CA1244017A (en) | 1988-11-01 |
| PT81018B (en) | 1987-06-24 |
| EP0174118A3 (en) | 1986-12-30 |
| JPS6168469A (ja) | 1986-04-08 |
| DK379985D0 (da) | 1985-08-21 |
| AU4648185A (en) | 1986-03-13 |
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