KR840005103A - 1-아릴옥시-2,3,4,5-테트라하이드로-3-벤즈아제핀의제조방법 - Google Patents
1-아릴옥시-2,3,4,5-테트라하이드로-3-벤즈아제핀의제조방법 Download PDFInfo
- Publication number
- KR840005103A KR840005103A KR1019830002597A KR830002597A KR840005103A KR 840005103 A KR840005103 A KR 840005103A KR 1019830002597 A KR1019830002597 A KR 1019830002597A KR 830002597 A KR830002597 A KR 830002597A KR 840005103 A KR840005103 A KR 840005103A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- hydrogen
- lower alkyl
- alkylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- -1 alkenyl cyanide Chemical compound 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000007344 nucleophilic reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- R'가 수소, 토실 또는 메실그룹인 일반식(Ⅲ/Ⅳ)의 화합물을 일반식(Ⅴ)의 할라이드 또는 일반식(Ⅷ)의 페놀과 반응시켜 R1가 수소, 또는 토실 또는 메실그룹인 일반식(Ⅵ/Ⅶ)의 화합물을 생성되고, 수득된 화합물을 (R1가 토실 또는 메실그룹이다) 알칼리금속, 또는 보론 또는 알루미늄 수소화물의 복합체로 환원하면, R1가 수소인 일반식(Ⅵ-Ⅶ)의 화합물이 생성되고, 임의 일반식(Ⅵ)의 화합물을 시판친핵성반응조건하에서 일반식 Hal-R3(Hal은 할로겐이다)의 할라이드와 반응시켜 일반식(Ⅰ)의 화합물을 생성되고, 임의 R이인 일반식(Ⅰ)의 화합물을 환원시켜, R이 저급알킬 또는 아릴저급알킬인 일반식(Ⅰ)의 화합물을 생성되고, 임의 R가저급알킬인 일반식(Ⅰ)의 화합물을 환원하면 R이 메틸인 일반식(Ⅰ)의 화합물을 생성되고, 임의 일반식(Ⅵ)의 화합물을 알킬렌부분이 탄소수 1 내지 5인 일반식-알케닐-CN의 측쇄 또는 직쇄알케닐 시아나이드와 반응시켜 일반식(XIⅤ)의 중간 생성화합물이 생성되고, 임의 일반식(XIⅤ)의 화합물을 환원하면, R이-알킬렌-CH2-NH2(알킬렌부분은 탄소수 1 내지 5이다)인 일반식(Ⅰ)의 화합물을 생성하거나, 임의로 R이-알킬렌(알킬렌 부분이 탄소수 1 내지 6이고, 적어도 R1은 수소이다)인 일반식(Ⅰ)을 저급알킬 할라이드와 반응시키면, 적어도 모노치환된 이의 N- 알킬 유도체가 생성되고, 알킬 할로포르메이트와 반응시키고, 뒤에 생성된 혼합물을 환원하면, 적어도 모노 치환된 N-메틸윧ㅎ체가 생성되고, 임의 통상적인 방법으로 이의 약학적으로 허용될 수 있는 산부가염을 제조함을 포함하는 일반식(I)의 화합물 및 약학적으로 허용될 수 있는 이의 산부가염을 제조하는 방법.상기식에서, Y1및 Y2는 같거나 다르고, 수소 또는 저급알콕시이며, X는 수소, 할로겐, 저급알킬, 저급알콕시, CF3, CN, NO2또는 NH2이고, R은 수소, 저급알킬, 시클로알킬저급알킬,일반식-알킬렌(여기에서, Z는 수소, 할로겐, 저급알킬, 저급알콕시, CF3, NO2와NH2)의 아릴저급알킬 또는 일반식 -알킬렌( R1및 R2는 같거나 다르며, 수소 또는 저급알킬이며며, 알킬렌부분의 탄소수는 1 내지 6이다)의 알킬렌아민이고, R3는 저급알킬, 시클로알킬저급-알킬, 일반식알킬렌(여기에서, 알킬렌부분의 탄소수는 1 내지 6이고, Z는 수소, 할로겐, 저급알킬, 저급알콕시, CF3, NO2, 또는 NH2이다),(R4는 탄소수 1 내지 5의 알킬이다)또는 -알킬렌(알킬렌부분의 탄소수는 1 내지 5이고, Z는 상기 정의한 바와 같다), -알킬렌-CN( 알킬렌부분의 탄소수는 1 내지 6이다), R1과 R2는 같거나 다르며, 수소 또는 저급알킬이다), 또는 R3가-알킬렌(알킬렌부분의 탄소수는 1 내지 5이다)이다.
- 화합물(Ⅰ)의 화합물 및/또는 이의 생리적으로 허용되는 산부가염중 하나를 적어도 하나의 고체, 액체 또는 반-액체 부형제 또는 보조제 및 임의로 추가의 활성성분과 함께 적당한 제형으로 제형화함을 특징으로 하는 약제학적 조성물의 제조방법.
- 일반식(Ⅰ)의 화합물 및/또는 이의 약제학적으로 허용되는 산부가염중 하나를 포함하는 약학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US387,916 | 1982-06-14 | ||
| US06/387,916 US4988690A (en) | 1982-06-14 | 1982-06-14 | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof |
| US389,916 | 1995-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840005103A true KR840005103A (ko) | 1984-11-03 |
| KR900001214B1 KR900001214B1 (ko) | 1990-02-28 |
Family
ID=23531838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830002597A KR900001214B1 (ko) | 1982-06-14 | 1983-06-11 | 1-아릴옥시-2,3,4,5-테트라하이드로-3-벤즈아제핀의 제조방법 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4988690A (ko) |
| EP (1) | EP0096838B1 (ko) |
| JP (1) | JPS595165A (ko) |
| KR (1) | KR900001214B1 (ko) |
| AT (1) | ATE26263T1 (ko) |
| AU (1) | AU570920B2 (ko) |
| CA (1) | CA1214460A (ko) |
| DE (1) | DE3370621D1 (ko) |
| DK (1) | DK270983A (ko) |
| ES (1) | ES523191A0 (ko) |
| FI (1) | FI78473C (ko) |
| GR (1) | GR78291B (ko) |
| HU (1) | HU190902B (ko) |
| IE (1) | IE55404B1 (ko) |
| IL (1) | IL68964A (ko) |
| PT (1) | PT76864B (ko) |
| ZA (1) | ZA834309B (ko) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA882080B (en) * | 1987-03-27 | 1989-04-26 | Schering Corp | Substituted benzazepines,their preparation and pharmaceutical compositions containing them |
| US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| ZA885824B (en) * | 1987-08-14 | 1989-04-26 | Merrell Dow Pharma | Novel antidepressants |
| US5202319A (en) * | 1991-09-23 | 1993-04-13 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 3-amino-2,3,4,5-tetrahydro-1-aryloxy-3-benzazepines |
| US5639482A (en) * | 1993-11-10 | 1997-06-17 | Crary; Ely J. | Composition for control and prevention of diabetic retinopathy |
| AU2002228725A1 (en) * | 2000-11-30 | 2002-06-11 | Advanced Research And Technology Institute, Inc. | Nucleophilic approach for preparing radiolabeled imaging agents and associated compounds |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| EP2332919A3 (en) * | 2003-06-17 | 2011-10-19 | Arena Pharmaceuticals, Inc. | Processes for preparing 3-benzazepines |
| 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 |
| US20070275949A1 (en) * | 2003-10-22 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases |
| WO2005042491A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| DK1838677T3 (da) | 2004-12-21 | 2010-01-11 | Arena Pharm Inc | Krystallinske former af (R)-8-chlor-1.methyl-2,3,4,5-tetrahydro-1H-3-benzazepinhydrochlorid |
| CN102627607A (zh) * | 2004-12-23 | 2012-08-08 | 艾尼纳制药公司 | 5HT2c受体调节剂组合物和使用方法 |
| CA2646044A1 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| WO2008070111A2 (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 |
| KR20100017767A (ko) * | 2007-05-10 | 2010-02-16 | 에이엠알 테크놀로지, 인크. | 아릴옥시- 및 헤테로 아릴옥시-치환된 테트라히드로벤즈아제핀 및 도파민 및 세로토닌의 재흡수를 차단하기 위한 이의 용도 |
| 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 |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| SG10201506874UA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| US9365521B2 (en) | 2010-09-01 | 2016-06-14 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-HT2C agonists |
| JP2013539470A (ja) | 2010-09-01 | 2013-10-24 | 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 | ロルカセリンと光学活性な酸との塩 |
| KR20180094131A (ko) | 2010-09-01 | 2018-08-22 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 신장 손상을 갖는 개체에 대한 로카세린의 투여 |
| MX2015004532A (es) | 2012-10-09 | 2016-01-20 | Arena Pharm Inc | Metodo de control del peso. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5233687A (en) * | 1975-09-11 | 1977-03-14 | Shionogi & Co Ltd | Process for preparation of 1,5-dihydro-2h-1,4-benzodiazepine-2-on deri vatives |
| JPS5481290A (en) * | 1977-11-17 | 1979-06-28 | Smithkline Corp | Benzazepin compound |
-
1982
- 1982-06-14 US US06/387,916 patent/US4988690A/en not_active Expired - Fee Related
-
1983
- 1983-06-08 AT AT83105610T patent/ATE26263T1/de not_active IP Right Cessation
- 1983-06-08 DE DE8383105610T patent/DE3370621D1/de not_active Expired
- 1983-06-08 EP EP83105610A patent/EP0096838B1/en not_active Expired
- 1983-06-10 FI FI832092A patent/FI78473C/fi not_active IP Right Cessation
- 1983-06-11 KR KR1019830002597A patent/KR900001214B1/ko active IP Right Grant
- 1983-06-13 GR GR71648A patent/GR78291B/el unknown
- 1983-06-13 DK DK270983A patent/DK270983A/da not_active Application Discontinuation
- 1983-06-13 ES ES523191A patent/ES523191A0/es active Granted
- 1983-06-13 CA CA000430280A patent/CA1214460A/en not_active Expired
- 1983-06-13 IL IL68964A patent/IL68964A/xx unknown
- 1983-06-13 JP JP58104343A patent/JPS595165A/ja active Granted
- 1983-06-13 ZA ZA834309A patent/ZA834309B/xx unknown
- 1983-06-13 IE IE1384/83A patent/IE55404B1/en unknown
- 1983-06-13 HU HU832096A patent/HU190902B/hu not_active IP Right Cessation
- 1983-06-14 PT PT76864A patent/PT76864B/pt unknown
- 1983-06-14 AU AU15764/83A patent/AU570920B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| FI78473C (fi) | 1989-08-10 |
| DK270983D0 (da) | 1983-06-13 |
| CA1214460A (en) | 1986-11-25 |
| GR78291B (ko) | 1984-09-26 |
| IE831384L (en) | 1983-12-14 |
| PT76864A (en) | 1983-07-01 |
| JPS595165A (ja) | 1984-01-12 |
| US4988690A (en) | 1991-01-29 |
| IE55404B1 (en) | 1990-09-12 |
| PT76864B (en) | 1986-02-27 |
| JPH0365342B2 (ko) | 1991-10-11 |
| EP0096838B1 (en) | 1987-04-01 |
| DE3370621D1 (en) | 1987-05-07 |
| AU1576483A (en) | 1983-12-22 |
| ES8503666A1 (es) | 1985-03-01 |
| HU190902B (en) | 1986-12-28 |
| FI78473B (fi) | 1989-04-28 |
| FI832092L (fi) | 1983-12-15 |
| IL68964A (en) | 1988-03-31 |
| KR900001214B1 (ko) | 1990-02-28 |
| ATE26263T1 (de) | 1987-04-15 |
| EP0096838A1 (en) | 1983-12-28 |
| IL68964A0 (en) | 1983-10-31 |
| ES523191A0 (es) | 1985-03-01 |
| ZA834309B (en) | 1984-03-28 |
| DK270983A (da) | 1983-12-15 |
| AU570920B2 (en) | 1988-03-31 |
| FI832092A0 (fi) | 1983-06-10 |
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