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WO1996039133A1 - Nouvelles 2-amino-3'-4'-methylene-dioxypropiophenones n-substituees - Google Patents

Nouvelles 2-amino-3'-4'-methylene-dioxypropiophenones n-substituees Download PDF

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Publication number
WO1996039133A1
WO1996039133A1 PCT/US1996/009603 US9609603W WO9639133A1 WO 1996039133 A1 WO1996039133 A1 WO 1996039133A1 US 9609603 W US9609603 W US 9609603W WO 9639133 A1 WO9639133 A1 WO 9639133A1
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WO
WIPO (PCT)
Prior art keywords
formula
acid
butyl
compound
compounds
Prior art date
Application number
PCT/US1996/009603
Other languages
English (en)
Inventor
Peyton Jacob, Iii
Alexander T. Shulgin
Original Assignee
Neurobiological Technologies, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Neurobiological Technologies, Inc. filed Critical Neurobiological Technologies, Inc.
Priority to AU61041/96A priority Critical patent/AU6104196A/en
Publication of WO1996039133A1 publication Critical patent/WO1996039133A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention generally relates to substituted araIky1amines, and more particularly to 2- alkylamino-3' ,4 '-methylenedioxypropiophenones with bio ⁇ logical activity such as central nervous system pharma ⁇ cological activity.
  • R is H, normal alkyl C_ to C 6 , isopropyl, isobutyl, sec-butyl, t-butyl, allyl, propargyl, or cyclopropyl, and R 2 is H.
  • a preferred embodiment is the compound where R x is a methyl group and R 2 is H:
  • the carbon atom of 2-methylamino-3 ' ,4 '- methylenedioxypropiophenone that is beta to the carbonyl function is chiral, so that this target compound can exist in either of two optical forms, although the racemic mixture can be used.
  • Acute therapeutic levels of the Formula II embodiments are expected to be between about 100 and 150 mg for oral administration.
  • the compounds have central nervous system activity, particularly anti-depressant and anti-Parkinson properties, and are also useful in vitro for diagnostic and assay applications, such as measuring serotonin or dopamine uptake sites.
  • a preferred embodiment is the compound where Rj is a methyl group and R 2 is H:
  • Compounds of Formula I bind to the serotonin uptake site. They also bind to the dopamine uptake site. Compounds of Formula I and their physiologically acceptable acid addition salts can, therefore, be used as biologically active compounds and also as intermediate products for the preparation of other biologically active compounds.
  • Acid addition salts may be formed by reaction with either inorganic or organic acids.
  • inorganic acids for example sulfuric acid, hydrogen halide acids, such as hydrochloric acid or hydrobromic acid, phosphoric acids, such as ortho- phosphoric acid, nitric acid, or sulfamic acid, and also organic acids, in particular aliphatic, alicyclic, araliphatic, aromatic, or heterocyclic monobasic or polybasic carboxylic, sulfonic or sulfuric acids, such as formic acid, acetic acid, propionic acid, pivalic acid, diethylacetic acid, malonic acid, succinic acid, pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, malic acid, benzoic acid, salicyclic acid, 2- phenylpropionic acid, citric acid, gluconic acid, ascorbic acid, nicotinic acid, isonicotinic acid, methanesulf
  • the invention further relates to the use of the compounds of Formula I and their physiologically acceptable salts for the preparation of pharmaceutical formulations.
  • they can be brought into a suitable dosage form together with at least one excipient or adjuvant and, if appropriate, in combination with one or more other active compound(s) .
  • an "agonist” is a chemical compound that mimics the action of the endogenous neurotransmitter at receptors.
  • serotonin agonists are chemical substances that bind to and mimic the action of serotonin on serotonin receptors (when direct-acting) .
  • uses for serotonin receptor agonists are as research and diagnostic tools.
  • the inventive compounds can be used to measure serotonin and dopamine uptake sites in a sample, for example, by radiolabelling as is known to the art.
  • the formulations can further include excipients, particularly when formulating for pharmaceutical uses.
  • Suitable excipients are organic or inorganic substances which are suitable for enteral (for example oral) or parenteral administration or for local application, and which do not react with the new compounds, for example water, vegetable oils, benzyl alcohols, polyethylene glycols, gelatins, carbohydrates, such as lactose or starch, magnesium stearate, talc or petroleum jelly.
  • Tablets, dragees, capsules, syrups, elixirs, drops or suppositories are especially used for enteral administration; solutions, preferably oily or aqueous solutions, and also suspensions, emulsions or implants are especially used for parenteral administration.
  • compositions of this invention are water soluble salts, isotonic and sterile solutions can readily be made and used, for example, for the preparation of solutions suitable for injection.
  • the formulations indicated can be sterilized and/or can contain adjuvants, such as lubricants, preservatives, stabilizing agents and/or wetting agents, emulsifiers, salts for regulating the osmotic pressure, buffer substances, colorants, flavoring substances and/or aroma generating substances. If desired, they can also contain one or more additional active compounds, for example one or more vitamins or mineral supplements.
  • the invention further relates to the use of the compounds of Formula I and their physiologically acceptable acid addition salts in combating diseases, particularly depressions of various etiologies and symptomatologies, and to their use in the therapeutic treatment of the human or animal body.
  • the substances of this invention are generally administered in a manner analogous to that of known psychopharmacological agents which are commercially available (for example Imipramine), in dosages generally ranging from about 2-500 mg, particularly of 10-50 mg, per dosage unit.
  • the daily dosage is preferably about 0.05 to 10 mg/kg of body weight.
  • the particular dose for each specific patient depends, however, on a very wide variety of factors, for example on the activity of the particular compound employed, on the age, body weight, general state of health, sex, and diet of the patient, on the time and route of administration, on the excretion rate and combination of medicaments and on the severity of the particular disease to which the therapy applies. Oral administration is preferred.
  • a TLC analysis (silica gel, methylene chloride/hexane) showed the distilled product to be largely carbinol, with two impurities that had Rf's greater than that of the product.
  • a solution was made of 10 g potassium dichromate in 65 mL water containing 7 mL concentrated sulfuric acid. This was vigorously stirred, and cooled with an external water bath. A total of 11.7 g of l-(3,4- methylenedioxyphenyl)-l-propanol was added without solvent, dropwise, over the course of 0.5 h, then heated on the steambath for an additional hour. The reaction mixture was poured into 2 L water, acidified with hydrochloric acid, and extracted with 3x100 mL methylene chloride.
  • the reaction mixture was clarified by filtration and the inorganic solids washed with additional methylene chloride.
  • the deep green combined filtrate and washings were filtered through a methylene chloride wetted bed of silica gel yielding a nearly colorless clear filtrate. This was stripped of solvent under vacuum, and the residue, 47.4 g, was distilled bulb-to-bulb.
  • the product distilled at 100-140°C at 0.15 mm/Hg yielding 42.87 g of 2-bromo-3' ,4'-methylenedioxypropiophenone as a pale amber oil that set up to a crystalline solid.
  • the GC-MS analysis showed the desired ketone as the major product (parent peaks, 256-258; major fragment 147, methylene- dioxybenzoyl; 121, methylenedioxyphenyl, confirming the chain bromination of the propiophenone).
  • a minor impurity was 2-chloro-3' ,4 '-methylenedioxypropiophenone, seen with parent peaks at 212/214, and the major peaks again at 149 and 121. It probably arose from the methylene chloride solvent, and does not interfere in any way with the subsequent aminative reaction.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention se rapporte à de nouveaux composés représentés par la formule générale (I), où R1 représente H, alkyle normal C1 à C6, isopropyle, isobutyle, sec-butyle, t-butyle, allyle, propargyle ou cyclopropyle et des sels de ceux-ci, et R2 représente H.
PCT/US1996/009603 1995-06-06 1996-06-06 Nouvelles 2-amino-3'-4'-methylene-dioxypropiophenones n-substituees WO1996039133A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU61041/96A AU6104196A (en) 1995-06-06 1996-06-06 Novel n-substituted-2-amino-3',4'-methylene-dioxypropiopheno nes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46740695A 1995-06-06 1995-06-06
US08/467,406 1995-06-06

Publications (1)

Publication Number Publication Date
WO1996039133A1 true WO1996039133A1 (fr) 1996-12-12

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Application Number Title Priority Date Filing Date
PCT/US1996/009603 WO1996039133A1 (fr) 1995-06-06 1996-06-06 Nouvelles 2-amino-3'-4'-methylene-dioxypropiophenones n-substituees

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AU (1) AU6104196A (fr)
WO (1) WO1996039133A1 (fr)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999038504A1 (fr) * 1998-01-29 1999-08-05 Sepracor Inc. Utilisations pharmaceutiques de (-)-bupropion optiquement pur
WO1999038502A1 (fr) * 1998-01-29 1999-08-05 Sepracor Inc. Utilisations pharmaceutiques de (+)-bupropion optiquement pur
US6337328B1 (en) 1999-03-01 2002-01-08 Sepracor, Inc. Bupropion metabolites and methods of use
US6342496B1 (en) 1999-03-01 2002-01-29 Sepracor Inc. Bupropion metabolites and methods of use
US6458374B1 (en) 1998-01-29 2002-10-01 Sepracor, Inc. Methods and compositions for treating chronic disorders using optically pure (+)-bupropion
US6734213B2 (en) 1999-01-20 2004-05-11 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6855820B2 (en) 1999-01-20 2005-02-15 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6998400B2 (en) 1998-01-22 2006-02-14 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US7098206B2 (en) 1998-01-21 2006-08-29 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US7189753B1 (en) 1997-11-06 2007-03-13 Cady Roger K Preemptive prophylaxis of migraine
WO2012110470A1 (fr) * 2011-02-17 2012-08-23 F. Hoffmann-La Roche Ag Nouvelles benzodioxolepipérazines
CN101659650B (zh) * 2009-09-24 2012-09-05 上海力智生化科技有限公司 一锅法制备洋茉莉醛的方法
WO2012117001A1 (fr) * 2011-03-03 2012-09-07 F. Hoffmann-La Roche Ag Nouveaux composés benzodioxole pipéridine
WO2018150230A1 (fr) 2017-02-14 2018-08-23 Anthea Aromatics Private Limited Procédé de préparation de dérivés alcényle et alkyle d'alkylènedioxybenzène
CN114544798A (zh) * 2022-01-05 2022-05-27 湖南恒生制药股份有限公司 盐酸多巴胺中间体1,3-苯并二氧戊烷的检测方法
WO2023081897A1 (fr) 2021-11-05 2023-05-11 Terran Biosciences, Inc. 3,4-méthylènedioxy-n-éthylamphétamine (mde) à enrichissement isotopique et stéréo-isomères associés
WO2023081403A1 (fr) * 2021-11-05 2023-05-11 Terran Biosciences Inc. Isotopologues, sels, formes cristallines, stéréoisomères, de méthylone et d'éthylone et leurs procédés d'utilisation
US11707446B2 (en) 2021-08-06 2023-07-25 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
WO2023191952A1 (fr) * 2022-03-31 2023-10-05 Transcend Therapeutics, Inc. Médicaments psychoactifs et leur utilisation pour le traitement de pathologies et de troubles psychiatriques et neurologiques
WO2024039599A1 (fr) * 2022-08-17 2024-02-22 Transcend Therapeutics, Inc. Précurseurs de phénéthylamines et de cathinones
US11958821B2 (en) 2021-11-17 2024-04-16 Terran Biosciences Inc. Phenethylamine compounds salts, polymorphic forms and methods of use thereof
WO2024086218A1 (fr) * 2022-10-20 2024-04-25 Transcend Therapeutics, Inc. Préparation de phénéthylamines et de cathinones, leurs stéreoisomeres et leurs précurseurs
US12295937B2 (en) 2021-08-06 2025-05-13 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
US12343326B2 (en) 2021-08-06 2025-07-01 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3523954A (en) * 1968-03-07 1970-08-11 Boehringer Sohn Ingelheim Novel alpha-amino-substituted (3,4-methylenedioxy - phenyl) - alkanones and salts thereof

Patent Citations (1)

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US3523954A (en) * 1968-03-07 1970-08-11 Boehringer Sohn Ingelheim Novel alpha-amino-substituted (3,4-methylenedioxy - phenyl) - alkanones and salts thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 54, No. 5, 10 March 1960, (Columbus, Ohio, USA), Abstract No. 4475i, SATODA I. et al., "Synthesis of Beta-(2,5-Dimethoxyphenyl)-beta-Hydroxyisopropylamine"; & YAKUGAKI ZASSHI, 1959, 79, 989-992. *

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7189753B1 (en) 1997-11-06 2007-03-13 Cady Roger K Preemptive prophylaxis of migraine
US7098206B2 (en) 1998-01-21 2006-08-29 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6998400B2 (en) 1998-01-22 2006-02-14 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6369113B2 (en) 1998-01-29 2002-04-09 Sepracor, Inc. Method for treating depression using optically pure (−)-bupropion
WO1999038504A1 (fr) * 1998-01-29 1999-08-05 Sepracor Inc. Utilisations pharmaceutiques de (-)-bupropion optiquement pur
US6277887B1 (en) 1998-01-29 2001-08-21 Sepracor, Inc. Methods for treating Parkinson's disease using optically pure (−)-bupropion
US6110973A (en) * 1998-01-29 2000-08-29 Sepracor Methods for treating obesity and weight gain using optically pure (-)-bupropion
US6451860B1 (en) 1998-01-29 2002-09-17 Sepracor, Inc. Methods for treating depression and other disorders using optically pure (−)-bupropion
US6458374B1 (en) 1998-01-29 2002-10-01 Sepracor, Inc. Methods and compositions for treating chronic disorders using optically pure (+)-bupropion
US6495605B2 (en) 1998-01-29 2002-12-17 Sepracor Inc. Methods and compositions for aiding in smoking cessation and for treating pain and other disorders using optically pure (+)-bupropion
WO1999038502A1 (fr) * 1998-01-29 1999-08-05 Sepracor Inc. Utilisations pharmaceutiques de (+)-bupropion optiquement pur
US6734213B2 (en) 1999-01-20 2004-05-11 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6855820B2 (en) 1999-01-20 2005-02-15 Smithkline Beecham Corporation Pharmaceutically active morpholinol
US6342496B1 (en) 1999-03-01 2002-01-29 Sepracor Inc. Bupropion metabolites and methods of use
US6337328B1 (en) 1999-03-01 2002-01-08 Sepracor, Inc. Bupropion metabolites and methods of use
CN101659650B (zh) * 2009-09-24 2012-09-05 上海力智生化科技有限公司 一锅法制备洋茉莉醛的方法
JP2014505715A (ja) * 2011-02-17 2014-03-06 エフ．ホフマン−ラ ロシュ アーゲー 新規なベンゾジオキソールピペラジン化合物
WO2012110470A1 (fr) * 2011-02-17 2012-08-23 F. Hoffmann-La Roche Ag Nouvelles benzodioxolepipérazines
US8722683B2 (en) 2011-02-17 2014-05-13 Hoffmann La-Roche Inc. Benzodioxole piperazine compounds
CN103380122A (zh) * 2011-02-17 2013-10-30 霍夫曼-拉罗奇有限公司 新苯并间二氧杂环戊烯哌嗪化合物
JP2014506905A (ja) * 2011-03-03 2014-03-20 エフ．ホフマン−ラ ロシュ アーゲー 新規なベンゾジオキソールピペリジン化合物
US8598357B2 (en) 2011-03-03 2013-12-03 Hoffmann-La Roche Inc. Benzodioxole piperidine compounds
CN103402511A (zh) * 2011-03-03 2013-11-20 霍夫曼-拉罗奇有限公司 新的苯并间二氧杂环戊烯哌啶化合物
WO2012117001A1 (fr) * 2011-03-03 2012-09-07 F. Hoffmann-La Roche Ag Nouveaux composés benzodioxole pipéridine
CN103402511B (zh) * 2011-03-03 2015-11-25 霍夫曼-拉罗奇有限公司 新的苯并间二氧杂环戊烯哌啶化合物
WO2018150230A1 (fr) 2017-02-14 2018-08-23 Anthea Aromatics Private Limited Procédé de préparation de dérivés alcényle et alkyle d'alkylènedioxybenzène
US11707446B2 (en) 2021-08-06 2023-07-25 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
US12233046B2 (en) * 2021-08-06 2025-02-25 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
EP4380588A4 (fr) * 2021-08-06 2025-10-08 Transcend Therapeutics Inc Médicaments psychoactifs et leur utilisation pour le traitement d'états pathologiques et de troubles psychiatriques et neurologiques
US12343326B2 (en) 2021-08-06 2025-07-01 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
US12295937B2 (en) 2021-08-06 2025-05-13 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
US11969407B2 (en) 2021-08-06 2024-04-30 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
US12059402B2 (en) 2021-08-06 2024-08-13 Transcend Therapeutics, Inc. Psychoactive medicines and their use for treating psychiatric and neurological conditions and disorders
WO2023081897A1 (fr) 2021-11-05 2023-05-11 Terran Biosciences, Inc. 3,4-méthylènedioxy-n-éthylamphétamine (mde) à enrichissement isotopique et stéréo-isomères associés
WO2023081403A1 (fr) * 2021-11-05 2023-05-11 Terran Biosciences Inc. Isotopologues, sels, formes cristallines, stéréoisomères, de méthylone et d'éthylone et leurs procédés d'utilisation
US12234216B2 (en) 2021-11-05 2025-02-25 Terran Biosciences Inc. Isotopologues salts, crystalline forms, stereoisomers, of methylone and ethylone and methods of use thereof
US11958821B2 (en) 2021-11-17 2024-04-16 Terran Biosciences Inc. Phenethylamine compounds salts, polymorphic forms and methods of use thereof
CN114544798A (zh) * 2022-01-05 2022-05-27 湖南恒生制药股份有限公司 盐酸多巴胺中间体1,3-苯并二氧戊烷的检测方法
CN114544798B (zh) * 2022-01-05 2023-08-08 湖南恒生制药股份有限公司 盐酸多巴胺中间体1,3-苯并二氧戊烷的检测方法
WO2023191952A1 (fr) * 2022-03-31 2023-10-05 Transcend Therapeutics, Inc. Médicaments psychoactifs et leur utilisation pour le traitement de pathologies et de troubles psychiatriques et neurologiques
WO2024039599A1 (fr) * 2022-08-17 2024-02-22 Transcend Therapeutics, Inc. Précurseurs de phénéthylamines et de cathinones
US12297220B2 (en) 2022-08-17 2025-05-13 Transcend Therapeutics, Inc. Phenethylamines and cathinones precursors
US20240327372A1 (en) * 2022-10-20 2024-10-03 Transcend Therapeutics, Inc. Preparation of phenethylamines and cathinones and stereoisomers thereof and precursors thereof
WO2024086218A1 (fr) * 2022-10-20 2024-04-25 Transcend Therapeutics, Inc. Préparation de phénéthylamines et de cathinones, leurs stéreoisomeres et leurs précurseurs

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