RU2009106169A - Получение 3-[(1r,2r)-3-(димитиламино)-1-этил-2-метилпропил]-фенола - Google Patents
Получение 3-[(1r,2r)-3-(димитиламино)-1-этил-2-метилпропил]-фенола Download PDFInfo
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- RU2009106169A RU2009106169A RU2009106169/04A RU2009106169A RU2009106169A RU 2009106169 A RU2009106169 A RU 2009106169A RU 2009106169/04 A RU2009106169/04 A RU 2009106169/04A RU 2009106169 A RU2009106169 A RU 2009106169A RU 2009106169 A RU2009106169 A RU 2009106169A
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 claims 1
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 claims 1
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 claims 1
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- -1 benzoic acid chloride anhydride Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 claims 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- ZELFLGGRLLOERW-YECZQDJWSA-N 3-[(2r,3r)-1-(dimethylamino)-2-methylpentan-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 ZELFLGGRLLOERW-YECZQDJWSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/20—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C219/22—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
1. Способ получения соединения формулы (VIII), или его соли присоединения кислоты, который характеризуется следующими стадиями ! a) ацилирование соединения формулы (VI), где R означает C1-6алкил, C3-8циклоалкил, C1-3алкилкарбонил, тетрагидропиранил, или C1-3алкил, замещенный фенил или нафтил при условии, что R - метил исключается, ! ! ацилирующим агентом; ! b) гидрогенолиз полученного таким образом соединения (VII) ! ! при использовании подходящего катализатора в реакционном инертном растворителе в присутствии водорода с образованием продукта VIII с R1=R или H: ! ! c) необязательно снятие защитной группы R1 формулы VIII в случае R1≠H и ! d) необязательно конвертирование полученного незащищенного продукта в соль присоединения кислоты. ! 2. Способ по п.1, в котором ацилирующий агент стадии а) является органическим ацилхлоридом или ангидридом органической кислоты. ! 3. Способ по п.2, в котором органический ацилхлорид или ангидрид органической кислоты выбран из уксусного ангидрида, ацетилхлорида, трифторуксусного ангидрида, хлоруксусного ангидрида, хлорацетилхлорида, дихлоруксусного ангидрида, трихлоруксусного ангидрида, бензойного ангидрида, бензоилхлорида, фталевого ангидрида, фтолоилдихлорида, терефталоилдихлорида, янтарного ангидрида, сукцинилхлорида, этилоксалилхлорида, метилоксалилхлорида, кислоты Мельдрума, этилхлороформата, метилхлороформата, или ацетилсалицилоилхлорида. ! 4. Способ по п.3, в котором ангидридом кислоты является трифторуксусный ангидрид. ! 5. Способ по любому из пп.1-4, в котором катализатор стадии b) выбран из никеля Реннея, палладия, палладия на угле, платины, платины на угле, рутения или родия на угле, или люб�
Claims (15)
1. Способ получения соединения формулы (VIII), или его соли присоединения кислоты, который характеризуется следующими стадиями
a) ацилирование соединения формулы (VI), где R означает C1-6алкил, C3-8циклоалкил, C1-3алкилкарбонил, тетрагидропиранил, или C1-3алкил, замещенный фенил или нафтил при условии, что R - метил исключается,
ацилирующим агентом;
b) гидрогенолиз полученного таким образом соединения (VII)
при использовании подходящего катализатора в реакционном инертном растворителе в присутствии водорода с образованием продукта VIII с R1=R или H:
c) необязательно снятие защитной группы R1 формулы VIII в случае R1≠H и
d) необязательно конвертирование полученного незащищенного продукта в соль присоединения кислоты.
2. Способ по п.1, в котором ацилирующий агент стадии а) является органическим ацилхлоридом или ангидридом органической кислоты.
3. Способ по п.2, в котором органический ацилхлорид или ангидрид органической кислоты выбран из уксусного ангидрида, ацетилхлорида, трифторуксусного ангидрида, хлоруксусного ангидрида, хлорацетилхлорида, дихлоруксусного ангидрида, трихлоруксусного ангидрида, бензойного ангидрида, бензоилхлорида, фталевого ангидрида, фтолоилдихлорида, терефталоилдихлорида, янтарного ангидрида, сукцинилхлорида, этилоксалилхлорида, метилоксалилхлорида, кислоты Мельдрума, этилхлороформата, метилхлороформата, или ацетилсалицилоилхлорида.
4. Способ по п.3, в котором ангидридом кислоты является трифторуксусный ангидрид.
5. Способ по любому из пп.1-4, в котором катализатор стадии b) выбран из никеля Реннея, палладия, палладия на угле, платины, платины на угле, рутения или родия на угле, или любого другого подходящего катализатора.
6. Способ по п.5, в котором катализатором является палладий на угле.
7. Способ по п.1, в котором реакционно-инертный растворитель стадии b) выбран из диэтилового эфира, тетрагидрофурана, 2-метилтетрагидрофурана или их смесей.
8. Способ по п.1, в котором R означает этил, н-пропил, изопропил, н-бутил, изобутил, трет-бутил, н-пентил, н-гексил, циклопропил, циклобутил, циклобутил, циклопентил, циклогексил, циклогептил, бензил, фенилэтил, тетрагидропиранил, -(C=O)-CH3, -(C=O)-CH2CH3, или -(C=O)-C(CH3)3.
9. Способ по п.8, в котором R означает бензил.
10. Способ по п.9, в котором (2R,3R)-3-(3-гидроксифенил)-N,N,2-триметилпентанамин превращают в его соответствующую хлористо-водородную соль присоединения кислоты.
11. Способ по п.1, в котором стадии a) и b) проводятся как однореакторный процесс.
12. Соединение формулы (VII), в котором R означает C1-6алкил, C3-8циклоалкил, C1-6алкилкарбонил, тетрагидропиранил, или C1-3-алкил, замещенный фенилом или нафтилом при условии, что R - метил исключается,
13. Соединение формулы (VII) по п.12, в котором ацил означает CH3-CO-, CF3-CO-, CH2Cl-CO-, CHCl2-CO-, CCl3-CO, CH3O-CO-, CH3CH2O-CO-, CH3O-CO-CO-, CH3CH2O-CO-CO-, фенил-CO-, или мета-CH3COO-фенил-CO-
14. Соединение формулы (VII) по п.13, в котором R означает этил, н-пропил, изопропил, н-бутил, изобутил, трет-бутил, н-пентил, н-гексил, циклопропил, циклобутил, циклобутил, циклопентил, циклогексил, циклогептил, бензил, фенилэтил, тетрагидропиранил, -(C=O)-CH3, -(C=O)-CH2CH3, или -(C=O)-C(CH3)3.
15. Соединение формулы (VII) по п.14, в котором ацил означает CF3-CO- и R означает бензил.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06015317.8 | 2006-07-24 | ||
| EP06015317 | 2006-07-24 |
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| Publication Number | Publication Date |
|---|---|
| RU2009106169A true RU2009106169A (ru) | 2010-08-27 |
| RU2463290C2 RU2463290C2 (ru) | 2012-10-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2009106169/04A RU2463290C2 (ru) | 2006-07-24 | 2007-07-23 | Получение 3-[(1r,2r)-3-(диметиламино)-1-этил-2-метилпропил]-фенола |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8263809B2 (ru) |
| EP (1) | EP2049464B1 (ru) |
| JP (1) | JP5357756B2 (ru) |
| KR (1) | KR101433685B1 (ru) |
| CN (1) | CN101495446B (ru) |
| AT (1) | ATE515491T1 (ru) |
| AU (1) | AU2007278463B2 (ru) |
| BR (1) | BRPI0714648B8 (ru) |
| CA (1) | CA2658648C (ru) |
| CY (1) | CY1111829T1 (ru) |
| DK (1) | DK2049464T3 (ru) |
| ES (1) | ES2366390T3 (ru) |
| HR (1) | HRP20110572T1 (ru) |
| IL (1) | IL196626A (ru) |
| MX (1) | MX2008016380A (ru) |
| NO (1) | NO341683B1 (ru) |
| NZ (1) | NZ573906A (ru) |
| PL (1) | PL2049464T3 (ru) |
| RU (1) | RU2463290C2 (ru) |
| SI (1) | SI2049464T1 (ru) |
| TW (1) | TWI401237B (ru) |
| WO (1) | WO2008012046A1 (ru) |
| ZA (1) | ZA200901279B (ru) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2656696C (en) * | 2006-07-24 | 2013-06-11 | Janssen Pharmaceutica N.V. | Preparation of (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentanamine |
| JP5706825B2 (ja) | 2008-10-17 | 2015-04-22 | シグネーチャー セラピューティクス, インク.Signature Therapeutics, Inc. | フェノール性オピオイドの放出が減弱された医薬組成物 |
| CN102002065B (zh) * | 2009-09-02 | 2014-09-10 | 上海特化医药科技有限公司 | 他喷他多的制备方法及其中间体 |
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| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
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| DE19805370A1 (de) * | 1997-03-14 | 1998-09-17 | Gruenenthal Gmbh | Substituierte Aminoverbindungen und ihre Verwendung als analgetisch wirksame Substanzen |
| US6399828B1 (en) * | 2001-10-29 | 2002-06-04 | Boehringer Ingelheim Chemicals, Inc. | Preparation of amphetamines from phenylpropanolamines |
| DE10326097A1 (de) | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
| DE10328316A1 (de) | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| CA2656696C (en) * | 2006-07-24 | 2013-06-11 | Janssen Pharmaceutica N.V. | Preparation of (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentanamine |
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