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US20080119661A1 - Process for the preparation of N-monosubstituted beta-amino alcohols - Google Patents

Process for the preparation of N-monosubstituted beta-amino alcohols Download PDF

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Publication number
US20080119661A1
US20080119661A1 US12/003,752 US375207A US2008119661A1 US 20080119661 A1 US20080119661 A1 US 20080119661A1 US 375207 A US375207 A US 375207A US 2008119661 A1 US2008119661 A1 US 2008119661A1
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United States
Prior art keywords
acid
formula
alkyl
group
thienyl
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.)
Abandoned
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US12/003,752
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English (en)
Inventor
Dominique Michel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lonza AG
Original Assignee
Lonza AG
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=30011063&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20080119661(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from US10/520,362 external-priority patent/US20050256318A1/en
Application filed by Lonza AG filed Critical Lonza AG
Priority to US12/003,752 priority Critical patent/US20080119661A1/en
Publication of US20080119661A1 publication Critical patent/US20080119661A1/en
Priority to US12/801,231 priority patent/US20100240911A1/en
Assigned to LONZA AG reassignment LONZA AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MICHEL, DOMINIQUE
Priority to US13/950,412 priority patent/US8962865B2/en
Priority to US14/580,577 priority patent/US20150112086A1/en
Priority to US14/836,357 priority patent/US20150361064A1/en
Priority to US15/698,935 priority patent/US20170369467A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • 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
    • 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
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms

Definitions

  • the invention relates to a process for the preparation of N-monosubstituted ⁇ -amino alcohols of formula and/or an addition salt of a proton acid via direct synthesis of N-monosubstituted ⁇ -keto amines of formula and/or an addition salt of a proton acid.
  • amine or “amines” include their corresponding addition salts of proton acids.
  • EP-A 457 559 and EP-A 650 965 disclose the preparation of N,N-dimethyl ⁇ -amino alcohols via Mannich-type reactions of methyl ketones with paraformaldehyde and dimethylamine followed by reduction of the carbonyl group. After reaction of the hydroxyl group affording alkyl or aryl ether derivatives one methyl radical is removed to obtain N-monosubstituted compounds which requires delicate and expensive reactions.
  • R 1 represents furanyl or thienyl.
  • R 2 represents linear or branched C 1-8 alkyl. More particularly preferred R 2 represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl.
  • the compound of formula V is present in an amount at least equimolar to that of the compound of formula IV.
  • the molar ratio of the compound of formula V to the compound of formula IV is between 1 and 2.
  • the solvent comprises water, an aliphatic or cycloaliphatic alcohol or a mixture thereof.
  • Particularly preferred alcohols are linear or branched aliphatic C 1-12 alcohols, cycloaliphatic C 5-8 alcohols, di- and/or trimeric ethylene glycols or mono C 1-4 alkyl or acetyl derivatives thereof, each of said alcohols containing 1 to 3 hydroxy groups.
  • Examples for said alcohols are methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutanol, tert-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 1-hexanol, 2-hexanol, cyclopentanol, cyclohexanol, 1,2-ethanediol, 1,2-propanediol, 1,2-butanediol, 2,3-butanediol, 1,4-butanediol, 1,2,3-propanetriol, 1,2,6-hexanetriol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoacetate, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl
  • the present invention also provides a compound of formula and its addition salts of proton acids, wherein R 4 represents methyl, ethyl, isobutyl and tert-butyl.
  • the present invention also provides a compound of formula and its addition salts of proton acids.
  • the present invention also provides a compound of formula and its addition salts of proton acids.
  • the present invention also provides a process for the preparation of a compound of formula and/or an addition salt of a proton acid, wherein R 1 and R 2 independently represent alkyl, cycloalkyl, aryl or aralkyl, each being optionally further substituted with alkyl, alkoxy and/or halogen, which process comprises reacting a mixture comprising
  • the compound of formula V can be used as a free amine and/or an addition salt of a proton acid thereof.
  • Particularly preferred are free amines, formates, acetates, oxalates, hydrochlorides, hydrobromides or mixtures thereof. More particularly preferred are free amines and/or hydrochlorides.
  • the compound of formula V is present in an amount at least equimolar to that of the compound of formula IV.
  • the molar ratio of the compound of formula V to the compound of formula IV is between 1 and 2.
  • Examples for said alcohols are methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutanol, tert-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 1-hexanol, 2-hexanol, cyclopentanol, cyclohexanol, 1,2-ethanediol, 1,2-propanediol, 1,2-butanediol, 2,3-butanediol, 1,4-butanediol, 1,2,3-propanetriol, 1,2,6-hexanetriol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoacetate, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl
  • said alcohol is ethanol, propanol, isopropyl alcohol, butanol, isobutanol, tert-butanol, diethylene glycol or triethylene glycol.
  • the proton acid is selected from the group consisting of formic acid, acetic acid, propionic acid, oxalic acid, HCl and HBr, more preferably it is selected from the group consisting of formic acid, acetic acid, HCl and HBr.
  • the pressure during the reaction is above 1.5 bar, more preferably in the range of 1.5 to 10 bar and particularly preferred in the range of 1.5 to 5 bar.
  • 2-Acetylthiophene (6.3 g, 50 mmol); isobutylamine hydrochloride (8.3 g, 75 mmol, 1.5 eq); paraformaldehyde (2.1 g, 75 mmol, 1.5 eq); HCl conc. (0.3 g); ethanol (35 mL); 110° C. for 9 hours; ca. 2 to 2.5 bar; removing of ethanol (35 mL) in vacuo; addition of ethyl acetate (50 mL); ca. 56% yield.
  • 2-Acetylthiophene (12.6 g, 100 mmol); isobutylamine hydrochloride (16.5 g, 150 mmol, 1.5 eq); paraformaldehyde (4.1 g, 140 mmol, 1.4 eq); HCl conc. (0.5 g); butanol (70 mL); heating under reflux (108° C.) for 7 hours; addition of ethyl acetate (100 mL); ca. 40% yield.
  • 2-Acetylfuran (7.5 g, 68 mmol); methylamine hydrochloride (6.9 g, 102 mmol, 1.5 eq); paraformaldehyde (3.1 g, 102 mmol, 1.5 eq); HCl conc. (1.15 g); ethanol (35 mL); 110° C. for 8 hours; ca. 2 to 2.5 bar; removing of ethanol (30 mL) in vacuo; addition of ethyl acetate (50 mL); ca. 64% yield.
  • 2-Acetophenone (21.0 g, 175 mmol); methylamine hydrochloride (17.5 g, 263 mmol, 1.5 eq); paraformaldehyde (7.9 g, 263 mmol, 1.5 eq); HCl conc. (1.1 g); ethanol (130 mL); 115° C. for 24 hours; ca. 2 to 2.5 bar; addition of ethyl acetate (170 mL); ca. 52% yield.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
US12/003,752 2002-06-09 2007-12-31 Process for the preparation of N-monosubstituted beta-amino alcohols Abandoned US20080119661A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US12/003,752 US20080119661A1 (en) 2002-07-09 2007-12-31 Process for the preparation of N-monosubstituted beta-amino alcohols
US12/801,231 US20100240911A1 (en) 2002-06-09 2010-05-28 Process for the preparation of N-monosubstituted beta-amino alcohols
US13/950,412 US8962865B2 (en) 2002-07-09 2013-07-25 Process for the preparation of N-monosubstituted β-amino alcohols
US14/580,577 US20150112086A1 (en) 2002-07-09 2014-12-23 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US14/836,357 US20150361064A1 (en) 2002-07-09 2015-08-26 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US15/698,935 US20170369467A1 (en) 2002-07-09 2017-09-08 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP02015229 2002-07-09
EP02015229.4 2002-07-09
PCT/EP2003/007411 WO2004005239A1 (en) 2002-07-09 2003-07-09 PROCESS FOR THE PREPARATION OF N-MONOSUBSTITUTED β-AMINO ALCOHOLS
US10/520,362 US20050256318A1 (en) 2002-07-09 2003-07-09 Process for the preparation of n-monosubstituted beta-amino alcohols
US12/003,752 US20080119661A1 (en) 2002-07-09 2007-12-31 Process for the preparation of N-monosubstituted beta-amino alcohols

Related Parent Applications (3)

Application Number Title Priority Date Filing Date
US10/520,362 Division US20050256318A1 (en) 2002-06-09 2003-07-09 Process for the preparation of n-monosubstituted beta-amino alcohols
PCT/EP2003/007411 Division WO2004005239A1 (en) 2002-06-09 2003-07-09 PROCESS FOR THE PREPARATION OF N-MONOSUBSTITUTED β-AMINO ALCOHOLS
US11/520,362 Division US7813503B2 (en) 2006-09-13 2006-09-13 Method and system for generation of cryptographic keys for use in cryptographic systems

Related Child Applications (4)

Application Number Title Priority Date Filing Date
US10/520,362 Continuation US20050256318A1 (en) 2002-06-09 2003-07-09 Process for the preparation of n-monosubstituted beta-amino alcohols
PCT/EP2003/007411 Continuation WO2004005239A1 (en) 2002-06-09 2003-07-09 PROCESS FOR THE PREPARATION OF N-MONOSUBSTITUTED β-AMINO ALCOHOLS
US13/950,412 Continuation US8962865B2 (en) 2002-07-09 2013-07-25 Process for the preparation of N-monosubstituted β-amino alcohols
US15/698,935 Continuation US20170369467A1 (en) 2002-07-09 2017-09-08 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols

Publications (1)

Publication Number Publication Date
US20080119661A1 true US20080119661A1 (en) 2008-05-22

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ID=30011063

Family Applications (7)

Application Number Title Priority Date Filing Date
US12/003,752 Abandoned US20080119661A1 (en) 2002-06-09 2007-12-31 Process for the preparation of N-monosubstituted beta-amino alcohols
US12/801,231 Abandoned US20100240911A1 (en) 2002-06-09 2010-05-28 Process for the preparation of N-monosubstituted beta-amino alcohols
US12/868,419 Expired - Fee Related US8558014B2 (en) 2002-07-09 2010-08-25 Process for the preparation of N-monosubstituted β-amino alcohols
US13/950,412 Expired - Lifetime US8962865B2 (en) 2002-07-09 2013-07-25 Process for the preparation of N-monosubstituted β-amino alcohols
US14/580,577 Abandoned US20150112086A1 (en) 2002-07-09 2014-12-23 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US14/836,357 Abandoned US20150361064A1 (en) 2002-07-09 2015-08-26 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US15/698,935 Abandoned US20170369467A1 (en) 2002-07-09 2017-09-08 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols

Family Applications After (6)

Application Number Title Priority Date Filing Date
US12/801,231 Abandoned US20100240911A1 (en) 2002-06-09 2010-05-28 Process for the preparation of N-monosubstituted beta-amino alcohols
US12/868,419 Expired - Fee Related US8558014B2 (en) 2002-07-09 2010-08-25 Process for the preparation of N-monosubstituted β-amino alcohols
US13/950,412 Expired - Lifetime US8962865B2 (en) 2002-07-09 2013-07-25 Process for the preparation of N-monosubstituted β-amino alcohols
US14/580,577 Abandoned US20150112086A1 (en) 2002-07-09 2014-12-23 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US14/836,357 Abandoned US20150361064A1 (en) 2002-07-09 2015-08-26 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols
US15/698,935 Abandoned US20170369467A1 (en) 2002-07-09 2017-09-08 Process for the Preparation of N-Monosubstituted beta-Amino Alcohols

Country Status (19)

Country Link
US (7) US20080119661A1 (de)
JP (1) JP4546242B2 (de)
KR (2) KR101021460B1 (de)
CN (4) CN1891683A (de)
AT (2) ATE444949T1 (de)
AU (1) AU2010201850B2 (de)
BR (1) BR0312651B1 (de)
CA (1) CA2491472C (de)
CY (1) CY1109691T1 (de)
DE (2) DE60316698T2 (de)
DK (1) DK1539673T3 (de)
EA (1) EA009394B1 (de)
ES (2) ES2334397T3 (de)
IL (1) IL166107A (de)
NO (2) NO329267B1 (de)
NZ (1) NZ537567A (de)
PT (2) PT1852415E (de)
SI (1) SI1852415T1 (de)
WO (1) WO2004005239A1 (de)

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DE10302595A1 (de) * 2003-01-22 2004-07-29 Basf Ag 3-Methylamino-1-(2-thienyl)-1-proganon, seine Herstellung und Verwendung
EP1566383A1 (de) * 2004-02-19 2005-08-24 Lonza AG Verfahren zur Herstellung von enantiomerenreinen 1-substituierten 3-Aminoalkoholen
KR101160502B1 (ko) * 2004-02-19 2012-06-28 론자 아게 거울상 이성질체적으로 순수한 1-치환된-3-아미노알콜의제조 방법
DE102004021434A1 (de) 2004-04-30 2005-11-24 Basf Ag Schnelle schaumarme Netzer für hydrophobe Oberflächen
EA200701613A1 (ru) 2005-02-21 2008-02-28 Лонца Аг Способ получения энантиомерно чистых 1-замещенных 3-аминоспиртов
CZ299270B6 (cs) 2006-01-04 2008-06-04 Zentiva, A. S. Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu
US20100280093A1 (en) 2006-07-03 2010-11-04 Ranbaxy Laboratories Limited Process for the preparation enantiomerically pure salts of n-methyl-3-(1-naphthaleneoxy)-3-(2-thienyl)propanamine
ATE552250T1 (de) 2006-12-22 2012-04-15 Synthon Bv Verfahren zur herstellung von duloxetin und verwandten verbindungen
US8288141B2 (en) 2008-08-27 2012-10-16 Codexis, Inc. Ketoreductase polypeptides for the production of 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
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