IL30458A - 6-chloro-2,3,4,5-tetrahydro-1h-3-benzazepine,its preparation and compositions containing it - Google Patents
6-chloro-2,3,4,5-tetrahydro-1h-3-benzazepine,its preparation and compositions containing itInfo
- Publication number
- IL30458A IL30458A IL30458A IL3045868A IL30458A IL 30458 A IL30458 A IL 30458A IL 30458 A IL30458 A IL 30458A IL 3045868 A IL3045868 A IL 3045868A IL 30458 A IL30458 A IL 30458A
- Authority
- IL
- Israel
- Prior art keywords
- tetrahydro
- benzazepine
- acid
- chloro
- salt
- Prior art date
Links
- KGJFKHNSLOSGMN-UHFFFAOYSA-N 6-chloro-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=C1C=CC=C2Cl KGJFKHNSLOSGMN-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XLZSZONYZUXOLD-UHFFFAOYSA-N 6-chloro-2,3,4,5-tetrahydro-1h-3-benzazepine;hydrochloride Chemical compound Cl.C1CNCCC2=C1C=CC=C2Cl XLZSZONYZUXOLD-UHFFFAOYSA-N 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical class C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- SWLJJEFSPJCUBD-UHFFFAOYSA-N tellurium tetrachloride Chemical compound Cl[Te](Cl)(Cl)Cl SWLJJEFSPJCUBD-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH197668A CH498122A (de) | 1968-02-09 | 1968-02-09 | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30458A0 IL30458A0 (en) | 1968-09-26 |
| IL30458A true IL30458A (en) | 1972-03-28 |
Family
ID=4223010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30458A IL30458A (en) | 1968-02-09 | 1968-07-29 | 6-chloro-2,3,4,5-tetrahydro-1h-3-benzazepine,its preparation and compositions containing it |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT277257B (en, 2012) |
| BE (1) | BE719631A (en, 2012) |
| CH (1) | CH498122A (en, 2012) |
| DE (1) | DE1795132A1 (en, 2012) |
| DK (1) | DK123526B (en, 2012) |
| ES (1) | ES357247A1 (en, 2012) |
| FR (1) | FR1598948A (en, 2012) |
| GB (1) | GB1225053A (en, 2012) |
| IL (1) | IL30458A (en, 2012) |
| NL (1) | NL6811311A (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4197297A (en) * | 1976-11-17 | 1980-04-08 | Smithkline Corporation | 6-Halo-7,8-dihydroxy-1-(hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US4160765A (en) * | 1976-11-17 | 1979-07-10 | Smithkline Corporation | Method for 6-bromination of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds |
| US4171359A (en) * | 1978-04-12 | 1979-10-16 | Smithkline Corporation | Benz-tetrasubstituted 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| CA2529401C (en) | 2003-06-17 | 2015-04-28 | Arena Pharmaceuticals, Inc. | Processes for preparing 3-benzazepines |
| EP1633720A1 (en) | 2003-06-17 | 2006-03-15 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases |
| TW200510324A (en) * | 2003-08-11 | 2005-03-16 | Lilly Co Eli | 6-(2,2,2-trifluoroethylamino)-7-chiloro-2, 3, 4, 5-tetrahydro-1h-benzo[d]azepine as a 5-ht2c receptor agonist |
| NZ555981A (en) | 2004-12-21 | 2011-01-28 | Arena Pharm Inc | Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| PT1833473E (pt) | 2004-12-23 | 2009-12-17 | Arena Pharm Inc | Composições de modulador de receptor 5ht2c e métodos de utilização |
| EP2471779A1 (en) | 2006-04-03 | 2012-07-04 | Arena Pharmaceuticals, Inc. | Process for the resolution of a mixture of (R)- and (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| JP5404414B2 (ja) | 2006-12-05 | 2014-01-29 | 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−ベンゾアゼピンおよびその中間体を調製するための方法 |
| US8822727B2 (en) | 2008-03-04 | 2014-09-02 | 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 |
| US8952197B2 (en) | 2009-06-18 | 2015-02-10 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| KR20130112848A (ko) | 2010-06-02 | 2013-10-14 | 아레나 파마슈티칼스, 인크. | 5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법 |
| JP6272695B2 (ja) | 2010-09-01 | 2018-01-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| SG188361A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| EP2939677A1 (en) | 2010-09-01 | 2015-11-04 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to indviduals with renal impairment |
| AU2011296014A1 (en) | 2010-09-01 | 2013-04-04 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| AR088670A1 (es) | 2012-10-09 | 2014-06-25 | Arena Pharm Inc | Metodo de control del peso |
-
1968
- 1968-02-09 CH CH197668A patent/CH498122A/de not_active IP Right Cessation
- 1968-07-29 IL IL30458A patent/IL30458A/en unknown
- 1968-08-08 NL NL6811311A patent/NL6811311A/xx unknown
- 1968-08-08 DK DK383268AA patent/DK123526B/da unknown
- 1968-08-14 AT AT797568A patent/AT277257B/de not_active IP Right Cessation
- 1968-08-14 FR FR1598948D patent/FR1598948A/fr not_active Expired
- 1968-08-14 ES ES357247A patent/ES357247A1/es not_active Expired
- 1968-08-14 DE DE19681795132 patent/DE1795132A1/de active Pending
- 1968-08-14 GB GB38772/68A patent/GB1225053A/en not_active Expired
- 1968-08-16 BE BE719631D patent/BE719631A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1795132A1 (de) | 1972-01-05 |
| GB1225053A (en) | 1971-03-17 |
| AT277257B (de) | 1969-12-29 |
| BE719631A (en, 2012) | 1969-02-17 |
| NL6811311A (en, 2012) | 1969-08-12 |
| IL30458A0 (en) | 1968-09-26 |
| FR1598948A (en, 2012) | 1970-07-15 |
| ES357247A1 (es) | 1970-03-01 |
| DK123526B (da) | 1972-07-03 |
| CH498122A (de) | 1970-10-31 |
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