ES482276A1 - Un procedimiento para la preparacion de 2,3,4,5-tetrahidro- 1h-3-benzazepinas mercapto substituidas. - Google Patents
Un procedimiento para la preparacion de 2,3,4,5-tetrahidro- 1h-3-benzazepinas mercapto substituidas.Info
- Publication number
- ES482276A1 ES482276A1 ES482276A ES482276A ES482276A1 ES 482276 A1 ES482276 A1 ES 482276A1 ES 482276 A ES482276 A ES 482276A ES 482276 A ES482276 A ES 482276A ES 482276 A1 ES482276 A1 ES 482276A1
- Authority
- ES
- Spain
- Prior art keywords
- benzazepines
- tetrahydro
- production
- pharmaceutical compositions
- alkanoyloxy
- 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
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical class C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 title abstract 2
- 102000015554 Dopamine receptor Human genes 0.000 title abstract 2
- 108050004812 Dopamine receptor Proteins 0.000 title abstract 2
- 230000000903 blocking effect Effects 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- -1 beta -hydroxyethyl Chemical group 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 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
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 abstract 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Neurology (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- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Un procedimiento para la preparación de 2,3,4,5- tetrahidro-1H-3-benzazepinas mercapto-subsistidas representadas por la fórmula **(Fórmula-01)** en donde R1 es fenilo, fenilo m- ó p-sustituido, el sustituyente siendo trifluorometilo, cloro, metoxi, metilo, flúor, nitro o hidroxi, ciclohexilo, tienilo, tienilmetilo, furilo o furilmetilo; ambos grupos R2 son metoxi, alcanoiloxi, la porción alcanoílica teniendo de 2 a 6 átomos de carbono, o hidroxi, y R''3 es hidrógeno, bromo, flúor, o trifluorometilo; o una sal ácida de adición farmacéuticamente aceptable, no tóxica del mismo, caracterizado porque comprende hacer reaccionar una diona representada por la fórmula **(Fórmula-02)** en donde R''3 es como se definió anteriormente, con un mercaptano, R1SH, en donde R1 es como se definió anteriormente, excepto por fenilo hidroxi- sustituido; tratar opcionalmente un producto fenílico metoxi-sustituido, con tribromuro de boro para dar el correspondiente derivado hidroxi- sustituido; hacer reaccionar opcionalmente el producto 7,8-dihidroxílico con diazometano o un halogenuro de alcanoílo para dar el correspondiente derivado dimetoxílico y dialcanoiloxílico, respectivamente; y formar opcionalmente una sal ácida de adición del compuesto obtenido como antes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92261378A | 1978-07-07 | 1978-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES482276A1 true ES482276A1 (es) | 1980-04-01 |
Family
ID=25447325
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES482276A Expired ES482276A1 (es) | 1978-07-07 | 1979-07-06 | Un procedimiento para la preparacion de 2,3,4,5-tetrahidro- 1h-3-benzazepinas mercapto substituidas. |
| ES482281A Expired ES482281A1 (es) | 1978-07-07 | 1979-07-06 | Un procedimiento para la prepracion de 2,3,4,5-tetrahidro- 1h-37benzazepinas mercapto-substituidas. |
| ES482282A Expired ES482282A1 (es) | 1978-07-07 | 1979-07-06 | Un procedimiento para la preparacion de 2,3,4,5-tetrahidro- 1h-3-benzazepinas mercapto-substituidas. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES482281A Expired ES482281A1 (es) | 1978-07-07 | 1979-07-06 | Un procedimiento para la prepracion de 2,3,4,5-tetrahidro- 1h-37benzazepinas mercapto-substituidas. |
| ES482282A Expired ES482282A1 (es) | 1978-07-07 | 1979-07-06 | Un procedimiento para la preparacion de 2,3,4,5-tetrahidro- 1h-3-benzazepinas mercapto-substituidas. |
Country Status (24)
| Country | Link |
|---|---|
| EP (2) | EP0007070B1 (es) |
| JP (1) | JPS5511584A (es) |
| AR (1) | AR222828A1 (es) |
| AU (1) | AU525789B2 (es) |
| CA (1) | CA1115271A (es) |
| CS (1) | CS213381B2 (es) |
| DD (1) | DD147355A5 (es) |
| DE (1) | DE2964530D1 (es) |
| DK (1) | DK156001C (es) |
| ES (3) | ES482276A1 (es) |
| FI (1) | FI67215C (es) |
| GR (1) | GR69675B (es) |
| HU (1) | HU179315B (es) |
| IE (1) | IE48654B1 (es) |
| IL (1) | IL57532A (es) |
| IT (1) | IT1193190B (es) |
| JO (1) | JO1273B1 (es) |
| NO (1) | NO152213C (es) |
| NZ (1) | NZ190745A (es) |
| PH (1) | PH15754A (es) |
| PL (1) | PL216908A1 (es) |
| PT (1) | PT69855A (es) |
| SU (1) | SU1029827A3 (es) |
| ZA (1) | ZA792785B (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3119874A1 (de) | 1981-05-19 | 1982-12-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
| US4469634A (en) * | 1982-07-29 | 1984-09-04 | Smithkline Beckman Corporation | Allyloxy- and allylthio-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US4652642A (en) * | 1984-08-23 | 1987-03-24 | Smithkline Beckman Corporation | Azidobenzazepines |
| US4683229A (en) * | 1986-03-17 | 1987-07-28 | Smithkline Beckman Corporation | 6-halo-9-alkenyleneoxy-3-alkyl-2,3,4,5-tetrahydro-(1H-3)-benzazepines and their use as selective alpha-adrenergic receptor antagonists |
| US5942250A (en) * | 1986-12-23 | 1999-08-24 | Tristrata Technology, Inc. | Compositions and methods for enhancing the topical effects of sunscreen agents |
| US6384079B1 (en) | 1986-12-23 | 2002-05-07 | Tristrata Technology, Incorporated | Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging |
| GB9119467D0 (en) * | 1991-09-12 | 1991-10-23 | Smithkline Beecham Corp | Chemical compounds |
| GB9708805D0 (en) | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| CO5140073A1 (es) | 1998-10-08 | 2002-03-22 | Smithkline Beecham Plc | Derivados de 2,3,4,5-tetrahidro-1h-3-benzapina |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| DE60305519T2 (de) * | 2002-10-07 | 2006-11-23 | Glaxo Group Ltd., Greenford | Sulfonamidderivate als antipsychotische mittel |
| HUE028976T2 (en) | 2003-06-17 | 2017-02-28 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| 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 |
| CN102329267A (zh) * | 2004-02-25 | 2012-01-25 | 伊莱利利公司 | 作为5-HT2C受体激动剂的6-取代的2,3,4,5-四氢-1H-苯并［d］氮杂䓬 |
| SI1838677T1 (sl) | 2004-12-21 | 2010-01-29 | Arena Pharm Inc | Kristalne oblike (R)-8-kloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzazepin hidroklorida |
| SG158168A1 (en) | 2004-12-23 | 2010-01-29 | Arena Pharm Inc | 5ht2c receptor modulator compositions and methods of use |
| 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 |
| US8299241B2 (en) | 2006-12-05 | 2012-10-30 | Arena Pharmaceuticals, Inc. | Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates thereof |
| CN102015591B (zh) | 2008-03-04 | 2014-01-29 | 艾尼纳制药公司 | 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法 |
| 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 |
| JP2013536859A (ja) | 2010-09-01 | 2013-09-26 | 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アゴニストの非吸湿性塩 |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| EP3485878A1 (en) | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| KR20140091458A (ko) | 2010-09-01 | 2014-07-21 | 아레나 파마슈티칼스, 인크. | 신장 손상을 갖는 개체에 대한 로카세린의 투여 |
| WO2014058441A1 (en) | 2012-10-09 | 2014-04-17 | Arena Pharmaceuticals, Inc. | Method of weight management |
| CN116655892B (zh) * | 2023-05-18 | 2026-03-31 | 常州大学 | 一种交联聚合物有机电极材料及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520264A (en) * | 1947-08-26 | 1950-08-29 | Maltbie Lab Inc | Substituted 3, 1-benz-2, 3, 4, 5-tetrahydroazepines |
| US3483185A (en) | 1966-08-16 | 1969-12-09 | American Home Prod | N-substituted 2,3,4,5-tetrahydro-1h-3-benzazepines |
| CA974989A (en) * | 1968-03-11 | 1975-09-23 | Wallace And Tiernan Inc. | Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby |
| US3671519A (en) | 1969-07-14 | 1972-06-20 | American Home Prod | N-substituted 2,3,4,5,-tetrahydro-1h-3-benzazepines |
| US3752892A (en) | 1970-03-11 | 1973-08-14 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepine derivative method and composition thereof |
| US3716639A (en) | 1970-03-11 | 1973-02-13 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepines |
| US4111957A (en) * | 1977-02-02 | 1978-09-05 | Smithkline Corporation | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds |
| US4108989A (en) * | 1977-04-01 | 1978-08-22 | Smithkline Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones |
-
1979
- 1979-06-05 ZA ZA792785A patent/ZA792785B/xx unknown
- 1979-06-11 IL IL57532A patent/IL57532A/xx unknown
- 1979-06-15 NZ NZ190745A patent/NZ190745A/xx unknown
- 1979-06-28 JP JP8252779A patent/JPS5511584A/ja active Granted
- 1979-07-02 PT PT69855A patent/PT69855A/pt unknown
- 1979-07-02 PH PH22728A patent/PH15754A/en unknown
- 1979-07-02 DK DK278379A patent/DK156001C/da not_active IP Right Cessation
- 1979-07-02 CS CS794635A patent/CS213381B2/cs unknown
- 1979-07-03 CA CA331,022A patent/CA1115271A/en not_active Expired
- 1979-07-03 AU AU48613/79A patent/AU525789B2/en not_active Ceased
- 1979-07-03 GR GR59498A patent/GR69675B/el unknown
- 1979-07-04 EP EP79102279A patent/EP0007070B1/en not_active Expired
- 1979-07-04 DE DE7979102279T patent/DE2964530D1/de not_active Expired
- 1979-07-04 EP EP82105188A patent/EP0080012B1/en not_active Expired
- 1979-07-05 FI FI792125A patent/FI67215C/fi not_active IP Right Cessation
- 1979-07-05 HU HU79SI1705A patent/HU179315B/hu unknown
- 1979-07-06 NO NO792267A patent/NO152213C/no unknown
- 1979-07-06 ES ES482276A patent/ES482276A1/es not_active Expired
- 1979-07-06 IT IT24165/79A patent/IT1193190B/it active
- 1979-07-06 SU SU792783746A patent/SU1029827A3/ru active
- 1979-07-06 ES ES482281A patent/ES482281A1/es not_active Expired
- 1979-07-06 DD DD79214179A patent/DD147355A5/de unknown
- 1979-07-06 AR AR277218A patent/AR222828A1/es active
- 1979-07-06 ES ES482282A patent/ES482282A1/es not_active Expired
- 1979-07-06 PL PL21690879A patent/PL216908A1/xx unknown
- 1979-07-07 JO JO19791273A patent/JO1273B1/en active
- 1979-08-08 IE IE1276/79A patent/IE48654B1/en unknown
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