WO1987003583A1 - Synthese d'aryloxypropanolamines et d'arylethanolamines - Google Patents

Synthese d'aryloxypropanolamines et d'arylethanolamines Download PDF

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Publication number
WO1987003583A1
WO1987003583A1 PCT/US1986/002406 US8602406W WO8703583A1 WO 1987003583 A1 WO1987003583 A1 WO 1987003583A1 US 8602406 W US8602406 W US 8602406W WO 8703583 A1 WO8703583 A1 WO 8703583A1
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WO
WIPO (PCT)
Prior art keywords
aryl
alkyl
metal
propoxy
chiral
Prior art date
Application number
PCT/US1986/002406
Other languages
English (en)
Inventor
Ghanshyam Patil
Khuong H. X. Mai
William L. Matier
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1987003583A1 publication Critical patent/WO1987003583A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • Aryloxypropanolamines and arylethanolamines are widely used therapeuttc agents, particularly those compounds possessing potent betaadrenergic receptor blocking activity. These beta-adrenergic blocking agents are widely used for a number of cardiovascular therapeutic indications, such as hypertension, angina pectoris, cardiac arrhythmias, myocardial infarction and more recently in the treatment of glaucoma.
  • certain ary loxypropanolamines possess potent beta-adrenergic stimulating properties and such compounds are used as cardiac stimulants.
  • the R isomers are less active or essentially devoid of beta-blocking activity as compared to their counterpart S isomers.
  • the R-isomer beta-agonists are more potent agents than their S-isomer counterparts.
  • p-TsCI p-toluenesufonyI chloride
  • R Ms or Ts
  • R 1 H 4b
  • Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is -NR 2 COR 3 , -NR 2 CONR 3 R 4 , -NR 2 SO 2 R 3 , -NR 2 SO 2 NR 3 R 4 , or -NR 2 COOR 5 , where R 2 , R 3 , R 4 , and R 5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R 3 and R 5 are not hydrogen when B is -NR 2 SO 2 R 3 or -NR 2 COOR 5 , or R 3 and R 4 may together with N form a 5- to 7-member
  • the method involves the utilization of trisubstituted phosphonlum hal ides such as R 3 P/CCI 4 as selective chlorinating agents to provide the monochloro derivative 5.
  • the chlorohydrin 5 is then converted into the aryloxypropanolamine 2 in the same reaction vessel or in separate steps as desired. It is noted that the undesirable dichloro intermediate 6 is not formed or formed in insignificant amounts in this reaction.
  • the method does not cause racemization of the optically active intermediate or final product and produces high purity chiral products. No complex separation steps are required to isolate a particular isomer. the three consecutive steps in the process may be performed in a single reaction vessel if desired. This makes the process much more efficient. Moreover, the method allows the use of economical starting materials.
  • Ar is aryl, substituted aryl, heteroaryl or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W ts a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B represents -NR 2 COR 3 , -NR 2 CONR 3 R 4 , -NR 2 SO 2 R 3 , -NR 2 SO 2 NR 3 R 4 , or -NR 2 COOR 5 wherein R 2 , R 3 , R 4 and R 5 may be the same or different and may be hydrogen, alkyl of from 1 to about 10 carbon atoms and preferably from 1 to about 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to about 10 carbon atoms and preferably fron 1 to about 6 carbon atoms; cycloalkyl of from 3 to about 8 carbon atoms, alkenyl of from 3 to about 10 carbon atoms
  • aryl represents a phenyl or naphthyl group which may be unsubstituted or substituted with alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halo, acetamido, amino, amido, nitro, alkyIamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or aryIalkoxy wherein the alkyl group contains form 1 to about 6 carbon atoms and the aryl group is substituted or unsubstituted phenyl.
  • heteroaryI represents pyridine, pyrazine, pyrrole, pyrazole, piperazine, thiophene, benzothiophene, furan, benzofuran, Imldazole, oxazole, indole, carbazole, thiazole, thiadiazole, benzothiadiazole, triazole, tetrazole, azepine, 1, 2-diazepine, or 1,4-thiazepine.
  • the heteroaryl is selected from the group consisting of pyridine, pyrazine, thiophene, benzothfophene, benzofuran, indole, carbazole, thiadiazole or benzothiadiazole, with the most preferred being pyrazine, indole, 1,2, 5-thiadiazole, or benzofuran.
  • heterocyclic as used herein represents pyrrolidine, piperidine, morphol ine, or thiomorphol ine.
  • the alkyl group contains from about 1 to about 6 carbon atoms and the aryl group represents substituted or unsubstltuted monocyclic or polycyclic aromatic or heterocycl ic ring systems of from 5 to about 10 carbon atoms, such as benzyl, phenethyl, 3,4-dimethoxyphenethyl, 1,1-dimethyl-2-(3-indolyl)-ethyI and the l ike.
  • Aromatic (Ar) substituents may include lower alkyl of from 1 to about 10 carbons atoms, alkenyl of from 2 to about 10 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 10 carbon atoms, halo, acetamido, amino, nitro, alkyIamino of from 1 to about 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 10 carbon atoms, cyano, aryIalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms and the aryl group represents substituted or unsubstituted phenyl and groups of the formula
  • R 4 -O-C-A wherein R 4 is lower alkyl, aryl or aralkyl and A is a direct bond, alkylene of from 1 to about 10 carbon atoms or alkenylene of from 2 to about 10 carbon atoms.
  • cycloalkyl refers to cycl ic saturated al iphatic radicals containing 3 to 6 carbon atoms in the ring, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyI.
  • the method involves the utilization of trisubstituted phosphonium hal ide, namely the R 3 P/CX 4 complex as selective halogenating agents, an example being the use of Ph 3 P/CCl 4 as selective chlorinating agents to provide the monochloro derivative, which is then converted into the aryloxypropanolamine.
  • the complete process can be performed in one reaction vessel to avoid having to isolate and purify intermediates, or can be performed stepwise.
  • the method can be used in the synthesis of beta agonists or beta-bIockers or any halohydrin intermediate.
  • R represents alkyl, aryl, cycloalkyl, alkylamino, aminoalkyl, cycloalkyl, amino or amino cycloakyl.
  • X represents halo, namely chloro, bromo or iodo.
  • the arylethanolamines can be prepared as follows, all in a single reaction vessel.
  • Aryl 1,2-ethanediol can be converted to the corresponding chlorohydrln by reacting it with Ph 3 P and CCI 4 in acetonitriIe.
  • the resulting chlorohydrin then can be cycl ized to an epoxide by treating it with one equivalent of sodium methoxlde.
  • the aryiethanolamine can then be obtained by treating the epoxide with one equivalent of amine.
  • the racemic, the (R)-(+) or S-(-) 3-(aryloxy)-1,2- propanediol (1) can be made by known methods.
  • the S-enantiomer can be prepared readily by reacting an appropriate phenoxide with R-(-)-2,2-dimethyl-4-(hydroxymethyl)-1,3- dioxolane methanesulfonate or p-toluene-sulfonate, followed by acid hydrolysis of the ketal.
  • the aryloxypropanolamine (4) can be made by mixing in the same reaction vessel, in the following named order, the 3-(aryloxy)-1,2- propanediol (1) with a trisubstituted phosphonium hal ide to prepare the aryl substituted halohydrin (2) which, unless desired, need not be isolated. A suitable base is then added to prepare the epoxide which, likewise, need not be isolated. A selected amine is then added to prepare the desired aryloxypropanolamine.
  • a suitable base for reaction with the halohydrin would be a metal alkoxide, metal hydroxide, metal hydride, metal carbonate or metal bicarbonate wherein the metal is sodium, potassium or calcium, or an ammonium hydroxide or a suitable organic base.
  • Preferred organic bases are pyridine, dlmethylaminopyridine, dimethylaniI ine, quinol ine,
  • DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene
  • DBN 1,5-Diazabicyclo[4,3.0]non- 5-ene
  • Preferred bases are sodium or potassium methoxide, ethoxide or t-butoxide or a tertiary alkyl amine.
  • beta-adrenergic blocking agents beta-agonists and partial agonists are representative of the compounds that can be made using the described process:
  • the solid was recrystaiIized from methyl ethyl ketone (MEK)/ether (200 mL/35 mL) to give white crystalline product (28.6 g, 29.7%), mp 91-94° C, -19.1 (C 1, MeOH).
  • MEK methyl ethyl ketone
  • the resulting mixture was diluted with 100 mL ethanol and treated with isopropylamine (10 mL, 2.4 equiv.) and refluxed for 2 hours.
  • the reaction mixture was evaporated to dryness.
  • the oily residue was taken up with ether (200 mL) and washed with water (2 x 200 mL) and then extracted with 1N hydrochloric acid (1 x 500 mL).
  • the ethereal layers were combined and acidified with hydrogen chloride until a pH of 2 was obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Procédé de préparation d'aryloxypropanolamine (1) ou d'aryléthanolamine (2) racémiques ou chirales de formule (1) ou (2) où Ar représente aryle, aryle substitué, hétéroaryle, ou aralkyle et R représente alkyle, alkyle substitué, aralkyle, ou WB, où W est un alkylène à chaîne droite ou ramifiée comportant de 1 à 6 atomes de carbone environ et où B est -NR2COR3, -NR2CONR3R4, -NR2SO2R3, -NR2SO2NR3R4, ou -NR2COOR5, où R2, R3, R4 et R5 peuvent être identiques ou différents et peuvent représenter hydrogène, alkyle, alkoxyalkyle, alcoxyaryle, cycloalkyle, alkényle, alkynyle, aryle, hétéroaryle ou aralkyle, à condition que R3 et R5 ne soient pas hydrogène lorsque B représente -NR2SO2R3 ou -NR2COOR5, ou alors R3 et R4 peuvent former en combinaison avec N un groupe hétérocyclique comportant de 5 à 7 membres. Ce procédé peut être utilisé pour préparer des agents béta-bloquants, utiles dans le traitement des troubles cardiaques.
PCT/US1986/002406 1985-12-04 1986-11-14 Synthese d'aryloxypropanolamines et d'arylethanolamines WO1987003583A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US80440685A 1985-12-04 1985-12-04
US804,406 1985-12-04

Publications (1)

Publication Number Publication Date
WO1987003583A1 true WO1987003583A1 (fr) 1987-06-18

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EP (1) EP0248879A4 (fr)
JP (1) JPS63502585A (fr)
AU (2) AU604005B2 (fr)
CA (1) CA1282787C (fr)
WO (1) WO1987003583A1 (fr)
ZA (1) ZA868713B (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368071A1 (fr) * 1988-10-26 1990-05-16 G.D. Searle & Co. Méthode de préparation de diastéréoisomères R et S de n6-[(2-hydroxypropyl)aryl]adénosine
EP0369209A1 (fr) * 1988-10-26 1990-05-23 G.D. Searle & Co. R-diastéréomères de N6-[(alpha-hydroxypropyl)aryl]adénosines
EP0374425A1 (fr) * 1988-10-26 1990-06-27 G.D. Searle & Co. S-Diastéréomères de n6-[(2-hydroxy-propyl)aryl]adénosine
DE3844410A1 (de) * 1988-12-30 1990-07-19 Lindner Wolfgang Inversion der alkohol-konfiguration in alpha-aminoalkoholen ueber intramolekulare substitution der sulfonsaeureester
US5629345A (en) * 1993-07-23 1997-05-13 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
WO1998034930A1 (fr) * 1997-02-07 1998-08-13 Shell Internationale Research Maatschappij B.V. Procede de preparation de composes epoxidiques
US5965620A (en) * 1993-07-23 1999-10-12 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
CN102408285A (zh) * 2011-09-15 2012-04-11 东北师范大学 一种甲苯衍生物的苄基碳氢直接胺化方法
US20120277309A1 (en) * 2011-01-27 2012-11-01 Baxter Healthcare S.A. Methods of controlling venous irritation associated with the treatment of a cardiac disorder
US20120302637A1 (en) * 2011-01-27 2012-11-29 Baxter Healthcare S.A. Methods of Treating Tachycardia and/or Controlling Heart Rate While Minimizing and/or Controlling Hypotension

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4990668A (en) * 1985-12-04 1991-02-05 E. I. Du Pont De Nemours And Company Optically active aryloxypropanolamines and arylethanolamines
SE8801518D0 (sv) * 1988-04-22 1988-04-22 Astra Pharma Prod A novel process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4202978A (en) * 1978-02-08 1980-05-13 Hoffmann-La Roche Inc. (S)-1-[2-(4-(2-Hydroxy-s-(1-alkylaminopropoxy)phenylalkyl]-4-phenylpiperazines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4990668A (en) * 1985-12-04 1991-02-05 E. I. Du Pont De Nemours And Company Optically active aryloxypropanolamines and arylethanolamines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4202978A (en) * 1978-02-08 1980-05-13 Hoffmann-La Roche Inc. (S)-1-[2-(4-(2-Hydroxy-s-(1-alkylaminopropoxy)phenylalkyl]-4-phenylpiperazines

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Agric. Biol. Chem., issued May 1982, SHINOBU IRIUCHIJIMA et al., Asymmetric Hydrolysis of (+-)-1,2-Diacetoxy-3-Chloropropane and its Related Compounds with Lipase. Synthesis of Optically Pure (S)-Propranolol, Vol. 46, No. 5, pages 1153-1157. See pages 1153-54 and 1156. *
FIESER et al., Reagents for Organic Synthesis, issued 1969, 1974, A Wiley-Interscience Publication, Vol. 2, page 445 and Vol. 4, pages 551-552, Respectively *
See also references of EP0248879A4 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368071A1 (fr) * 1988-10-26 1990-05-16 G.D. Searle & Co. Méthode de préparation de diastéréoisomères R et S de n6-[(2-hydroxypropyl)aryl]adénosine
EP0369209A1 (fr) * 1988-10-26 1990-05-23 G.D. Searle & Co. R-diastéréomères de N6-[(alpha-hydroxypropyl)aryl]adénosines
EP0374425A1 (fr) * 1988-10-26 1990-06-27 G.D. Searle & Co. S-Diastéréomères de n6-[(2-hydroxy-propyl)aryl]adénosine
DE3844410A1 (de) * 1988-12-30 1990-07-19 Lindner Wolfgang Inversion der alkohol-konfiguration in alpha-aminoalkoholen ueber intramolekulare substitution der sulfonsaeureester
US5965620A (en) * 1993-07-23 1999-10-12 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
US5629345A (en) * 1993-07-23 1997-05-13 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
WO1998034930A1 (fr) * 1997-02-07 1998-08-13 Shell Internationale Research Maatschappij B.V. Procede de preparation de composes epoxidiques
US6001954A (en) * 1997-02-07 1999-12-14 Shell Oil Company Process for the manufacture of epoxy compounds
US6235870B1 (en) 1997-02-07 2001-05-22 Shell Oil Company Dehydrohalogenation of poly (phenylhalo-b-hydroxypropyl ether) to form polyepoxide
US20120277309A1 (en) * 2011-01-27 2012-11-01 Baxter Healthcare S.A. Methods of controlling venous irritation associated with the treatment of a cardiac disorder
US20120302637A1 (en) * 2011-01-27 2012-11-29 Baxter Healthcare S.A. Methods of Treating Tachycardia and/or Controlling Heart Rate While Minimizing and/or Controlling Hypotension
US8686036B2 (en) * 2011-01-27 2014-04-01 Baxter International Inc. Methods of controlling heart rate while minimizing and/or controlling hypotension
US8829047B2 (en) 2011-01-27 2014-09-09 Baxter International Inc. Methods of controlling venous irritation associated with the treatment of a cardiac disorder
US9084763B2 (en) 2011-01-27 2015-07-21 Baxter International Inc. Methods for treating tachycardia and/or controlling heart rate while minimizing and/or controlling hypotension
CN102408285A (zh) * 2011-09-15 2012-04-11 东北师范大学 一种甲苯衍生物的苄基碳氢直接胺化方法

Also Published As

Publication number Publication date
EP0248879A4 (fr) 1990-02-26
AU604005B2 (en) 1990-12-06
CA1282787C (fr) 1991-04-09
AU631433B2 (en) 1992-11-26
ZA868713B (en) 1987-06-24
EP0248879A1 (fr) 1987-12-16
AU5756290A (en) 1990-10-11
JPS63502585A (ja) 1988-09-29
AU6774987A (en) 1987-06-30

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