GB1598668A - Indolyloxymethyl-2-oxazolidinone derivatives and their use in the preparation of 1-amino-3-(indolyloxy)-2-propanols - Google Patents

Indolyloxymethyl-2-oxazolidinone derivatives and their use in the preparation of 1-amino-3-(indolyloxy)-2-propanols Download PDF

Info

Publication number
GB1598668A
GB1598668A GB20036/80A GB2003680A GB1598668A GB 1598668 A GB1598668 A GB 1598668A GB 20036/80 A GB20036/80 A GB 20036/80A GB 2003680 A GB2003680 A GB 2003680A GB 1598668 A GB1598668 A GB 1598668A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
process according
produced
group
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
Application number
GB20036/80A
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.)
Sandoz AG
Original Assignee
Sandoz 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
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1598668A publication Critical patent/GB1598668A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero 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
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/38—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • 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
    • C07D317/10—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 not condensed with other rings
    • C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms

Description

PATENT SPECIFICATION
Application No 20036/80 ( 22) Filed 21 March 1978 Divided out of No 1598667 Convention Application No 3754/77 Filed 24 March 1977 in Switzerland (CH) Complete Specification published 23 Sept 1981
INT CL 3 C 07 D 263/24 263/16 Index at acceptance C 2 C 1343 1371 213 215 247 250 251 255 25 Y 28 X 305 30 Y 351 352 360 361 364 36 Y 388 624 625 652 672 761 768 AA TX ( 72) Inventor EDOUARD LIER ( 54) NOVEL INDOLYLOXYMETHYL-2-OXAZOLIDINONE DERIVATIVES, AND THEIR USE IN THE PREPARATION OF l-AMINO-3(INDOLYLOXY)-2-PROPANOLS.
( 71) We, SANDOZ LTD, of 35 Lichtstrasse, 4002 Basle Switzerland, a Swiss Body Corporate, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:-
The invention provides a process for the o 10 production of a compound of formula I Ar-OCH 2 CH(OH)CH 2 NH-Rl I wherein Ar is indol-4-yl or 2-methylinol-4-yl and R, is isopropyl or tert-butyl and esters thereof, which comprises splitting off the group \ C=X / from a corresponding compound of formula II Ar O-CH 2-CH H 2 O c N-R 1 Ix X II wherein Ar and R, are as defined above and X is oxygen or sulfur and, if desired, esterifying the hydroxy group of the resultant compound of formula I.
The compounds of formula I are in general known The compounds of formula I and esters thereof are pharmacteutically active, possessing 5-blocking activity.
The compounds of formula I or an ester thereof may be in optically active (R) or (S) form or in racemic form.
The above process is applicable not only to the production of racemic compounds, but also, and preferably, to the production of optically active compounds in R or S form, because the configuration of the 2carbon of the propyl moiety is maintained in the above reaction and in the reactions described hereinafter.
The process is particularly useful for the production of optically active compounds.
Thus 2 S-isomers, which in general are the more active optical as regards beta-blocking activity, may be produced, in which case the intermediates have the following configuration:H O -OCH 2 C CH N 2 2 \ The process according to the invention may be effected in conventional manner, e.g under basic conditions, e g with an alkali metal hydroxide Alternatively strong acidic or reductive conditions, where appropriate, may be used.
An advantage of the process is that it may be effected under a wide range of conditions, e g acidic, basic or reductive conditions.
If desired the hydroxy group of the resultant compound of formula I may be esterified, e g by an aryl carboxylic acid, an aliphatic carboxylic acid or an alicyclic carboxylic acid of, e g up to 10 carbon atoms.
A compound of formula II may be produced by a process comprising condensing a compound of formula III Ar OH III wherein Ar is as defined above with a compound of formula IV, ( 21) ( 62) ( 31) ( 32) ( 33) ( 44) ( 51) ( 52) ( 11) 1 598 668 V-CH 2 _CH CH 2 II X N-R X IV wherein X and R, are as defined above and Z' is a leaving group.
This reaction may be effected in conventional manner The compound of formula IV may be obtained by introducing a leaving group Z' into a compound of formula V R 0.CHCH CH 2 \ N-R 1 X V wherein X and R 1 are as defined above.
The introduction of a leaving group Z' may be effected in conventional manner It is to be appreciated that Z' will be appropriately chosen bearing in mind the nature of the compounds Z' may be, for example, chloro, bromo or iodo or especially mesyloxy or tosyloxy.
A compound of formula V may be produced by a process comprising intramolecularly cyclizing a compound of formula VI.
HOCH 2-CH(OH-CH 2-NR,-C(X)R 2 VI wherein X and R, are as defined above and R 2 is a leaving group.
The process may be effected in conventional manner for such intromolecular cyclizations, e g of urethanes Conveniently X is oxygen R 2 is conveniently alkoxy (C 1 _ 4), haloalkoxy (C,4), phenoxy or benzyloxy unsubstituted or substituted by halogen, alkyl (C,_ 4) or alkoxy (C 1 _ 4) (halogen is preferably fluorine, bromine or especially chlorine) Preferred examples of R 2 include 2,2,2-trichloroethoxy, and especially methoxy, ethoxy, and unsubstituted benzyloxy or phenoxy The reaction is conveniently effected under basic conditions, e g in the presence of sodium hydroxide, pyridine or triethylamine Suitable reaction temperatures may be from O to 50 C, e g.
room temperature Suitable solvents include tetrahydrofuran, dioxane, ethanol or methanol, or water.
A compound of formula VI may be produced by a process comprising splitting off the protecting group A from a compound of formula VII H 2-CH-CH 2-N Rc -C (X) -R 2 VII 0 O A wherein R, R 2 and X are as defined above 50 and A is a protecting group.
The reaction may be effected in conventional manner for deprotecting a 1,2diol without splitting off the moiety 55 C(=X) R 2 The protecting group A is conviently a hydrophobic group and may, as will be appreciated from the reactions described hereinafter, for example be a base-stable group For example A may be 60 alkylidene, e g of I to 5 carbon atoms, which is preferably symmetrical, e g.
methylene or preferably isopropylidene.
Alternatively A may be a cycloalkylidene, e.g such as cyclohexylidene or 65 cyclopentylidene, or a benzylidene group which may be substituted in the ring, e g by nitro The reaction may be effected with an organic acid, e g aqueous acetic acid, or preferably with a mineral acid such as 70 aqueous hydrochloric acid An appropriate solvent such as methanol may be present.
Suitable temperatures are between O and C, e g 10 C It is to be appreciated that the resultant compound of formula VI may 75 be further converted into a compound of formula III directly without purification.
A compound of formula VII may be produced by a process comprising reacting a compound of formula VIII 80 CH 2 CH CH 2NHR O N.
VIII wherein A and R, are as defined above, with a compound of formula IX Y.C(=X) R 2 IX 85 wherein R 2 and X are as defined above and Y is a group capable of being split off with the hydrogen of an amine.
The reaction may be effected in conventional manner, e g for a SchottenBaumann reaction Y is, for example, chlorine Alternatively Y may be alkoxy (which may conveniently be the same as R, when this is alkoxy) The reaction may be effected at a temperature of from O to C.
A compound of formula VIII may be obtained by reductively aminating a compound of formula X H 2 CH CHO o O A/ 1, X 100 wherein A is as defined above The above process steps, in general, may lead to high yields of optically active or racemic products with the formation of few side products, or side products which may 105 be easily removed using conventional 1,598 668 1,598,668 purification procedures, e g crystallization, chromatography or distillation.
Naturally two or more of the above steps may be effected without isolating and/or purifying the intermediate product(s).
A particular advantage of this process as a whole is that when A is a hydrophobic group, then the intermediates of formulae VII and VIII are less water soluble than the corresponding diols with the result that working up of the reaction mixtures using extraction of aqueous solutions with organic solvents or washing of organic solutions with aqueous solvents is more efficient than with the corresponding diols Such an advantage is particularly useful when the intermediates of formulae VII and VIII are oils at room temperatures.
Insofar as the production of any compound is not particularly described, then this is known or may be prepared according to conventional methods.
The compounds of formula VII, their production and use as described above are described and claimed in Application No.
11113/78 (Patent Specification No.
1598667).
In the following examples all temperatures are in degree Centigrade and are uncorrected Unless otherwise mentioned all optical rotations are expressed as a 1 % (w/v) solution in methanol.
EXAMPLE 1 ( 2 S) I (Indol 4 yloxy) 3isopropylamino 2 propanol A suspension of 19 5 g of ( 55) 5 (indol 4 yloxy methyl) 3 isopropyl 2 oxazolidinone, 200 ml of ethanol and 180 ml of 4 N Na OH are heated at reflux overnight, the solvent is distilled off and the residue is taken up in methylene choride/water The aqueous phase is extracted with methylene chloride The combined organic phases are washed neutral with water, dried over Na 25 O 4 and concentrated by evaporation The residue is crystallized from benzene The title compound is obtained (M P 939450) li 120-7 8 ( 1 % CHCI 3) la 120 o 4 80 ( 1 %/ methanol).
The starting material may be obtained as follows:
a) ( 4 S) 4 Isopropylaminomethyl 2,2 dimethyl 1,3 dioxolane (Compound of formula VIII) 52.5 g of ( 4 R) 2,2 dimethyl 1,3 dioxolane 4 carbaldehyde in 400 ml methanol lobtained by treating 1,2,5,6diiso propylidene D mannitol with lead tetracetatel are added dropwise to a suspension of 5 25 g of 10 / palladium-oncharcoal in 150 ml of methanol and 86 ml of isopropylamine in the presence of hydrogen over 2 hours The mixture is hydrogenated overnight at I atmosphere.
The catalyst is filtered off and the methanol is distilled off The residue is stirred for 5 minutes with a solution of 95 g of Na 2 CO 3 in 500 ml of water and is extracted thrice with methylene chloride The organic phases are dried with Na 2 SO 4 and the filtrate is concentrated by evaporation.
The yellowish oil is subsequently distilled at 42 ( 0 1 mm Hg) to give the heading compound lcalo -7 2 ( 2 % methanol).
b) N l 4 S) 2,2 Dimethyl 1,3dioxolan 4 ylmethyll N isopropyl carbamic acid ethyl ester (Compound of formula VII) g of ( 4 S) 4 isopropylaminomethyl 2,2 dimethyl 1,3 dioxolane are dissolved in 1 5 1 of methylene chloride and are cooled to 0 To this solution there are added dropwise during the course of one hour simultaneously 92 ml of ethyl chloroformate and 240 ml of 4 N sodium hydroxide and the suspension is thoroughly stirred for 30 minutes at 0 The suspension is then made acid with cold 10 % tartaric acid, the phases are separated and the aqueous phase is extracted thrice with methylene chloride The combined organic phases are shaken twice with cold 2 N Na OH, washed with water, dried over Na 2 SO 4 and concentrated by evaporation.
Distillation of the residue yields pure N l( 4 S)2,2 dimethyl 1,3 dioxolan 4 ylmethyll N isopropylcarbamic acid ethyl ester of B P 96 ( 0 6 mm Hg), (a)J O -19 20.
c) ( 2 S)N ( 2,3 Dihydroxypropyl) N isopropylcarbamic acid ethyl ester (Compound of formula VI) 7 g of N l( 4 S) 2,2 dimethyl 1,3 dioxolan 4 ylmethyll N isopropylcarbamic acid ethyl ester are stirred in 500 ml of methanol and 115 ml of 4 N HCI for two hours at 10 and are concentrated by evaporation in a vacuum.
( 2 S) N ( 2,3 dihydroxypropyl) Nisopropyl carbamic acid ethyl ester is obtained, lal 20-19 9 %Y, which is further reacted in crude form.
d) ( 5 S) 5 Hydroxymethyl 3 isopropyl 2 oxazolidinone (Compound of formula V) 4 N Na OH are added to 98 7 g of crude ( 2 S) N ( 2,3 dihydroxypropyl) N-isopropylcarbamic acid ethyl ester until the p H is 13 The mixture is allowed to stand for 2 hours at 20 and then extracted thrice with methylene chloride The organic phases are washed with 6 M Na CI, dried 1,598,668 over Na 2 SO 4 and the solvent is distilled off.
The title compound is obtained (M P 5659 -from methylene chloride/ether).
lt 12 + 49 1 0.
Instead of ethyl chloroformate, either benzyl chloroformate or phenyl chloroformate may be used in step b) to produce the corresponding benzyl ester of formula VII B P 130-133 ( 0 03 mm Hg) lal -20 1 ( 2 % methanol) or phenyl ester of formula VII B P 123-125 ( 0 1 mm Hg) la 20 _ 33 7 , respectively, which may be further reacted according to steps c) and d) to produce ( 5 S) 5 hydroxymethyl 3 isopropyl 2 oxazolidinone.
e) ( 5 S) 3 isopropyl 5 tosyloxymethyl 2 oxazolidinone (Compound of formula IV) 32.8 g of p-toluenesulfonyl chloride are added over 30 minutes to a solution of 24 8 g of ( 5 S) 5 hydroxymethyl 3 isopropyl 2 oxazolidinone in 60 ml of pyridine at -5 and are kept overnight at 00.
The mixture is poured onto ice, the oil is extracted with methylene chloride and the organic phases are washed with 2 N HCI and water After the phases have been dried over Na SO 4 the methylene chloride is removed and the residue is crystallized from methylene chloride/ether ( 5 S) 3 Isopropyl 5 tosyloxymethyl 2oxazolidinone is obtained (M P 77-79 ) la 1 l 20 + 51 8 f) ( 5 S)5 (indol 4 yloxymethyl) 3 isopropyl 2 oxazolidinone (Compound of formula II) A solution of 17 4 g of 4 hydroxyindole in ml of N,N dimethylformamide is added dropwise during one hour to a suspension of 6 3 g of sodium hydride ( 50 % dispersion) and 50 ml of N,N dimethylformamide under argon The temperature is kept below 35 The suspension is stirred for 1.5 hours at room temperature, 41 g of ( 5 S) 3 isopropyl 5 tosyloxymethyl 2 oxazolidinone in 50 ml of N,N-dimethylformamide are added dropwise and stirred at 80 overnight under argon.
The suspension is poured onto ice and shaken with methylene chloride The organic phases are washed with 2 N Na OH and water, dried over Na 2 SO 4 and concentrated by evaporation The residue is crystallized from methylene chloride/ether ( 5 S) 5 (Indol 4 yloxymethyl) 3 isopropyl 2 oxazolidinone is obtained (M P 139142 -from CH 2 CI 2/ether) lal 20 + 56 7 .
EXAMPLE 2
In analogous manner to that described in Example 1, racemic 2,2 dimethy 1,3 dioxolane 4 carbaldehyde may be converted into racemic I (indol 4yloxy) 3 isopropylamino 2 propanol.
M.P 171-173 (from ethanol).
EXAMPLE 3
In analogous manner to that described in Example 1, 4 S 2,2 dimethyl 1,3 dioxolane 4 carbaldehyde may be converted into ( 2 R) I (indol 4yloxy) 3 isopropylamino 2 propanol.
M.P 93-95 O la 1 46 + 77 ( 1 % CHCI 3).
lal 546 + 4 8 ( 1 % methanol).

Claims (17)

  1. WHAT WE CLAIM IS:-
    I A process for the production of a compound of formula I Ar-OCH 2 CH(OH)CH 2 NH-R, I wherein Ar is indol 4 yl or 2 methylindol 4 yl and R, is isopropyl or tert-butyl, and esters thereof, which comprises splitting off the group C=X / from a corresponding compound of formula II Ar O-CH 2-CH HH 2 O O CN-R x X II wherein Ar and R 1 are as defined above and X is oxygen or sulfur, and, if desired, esterifying the hydroxy group of the resultant compound of formula I.
  2. 2 A process according to claim I wherein X is 0.
  3. 3 A process according to claim I wherein the compound of formula II is produced by condensing a compound of formula III Ar OH III wherein Ar is as defined in claim 1 with a compound of formula IV :-% l CH CH 2 c N-R 1 11 1 IIX X IV wherein X and R, are as defined in claim I and Z' is a leaving group.
  4. 4 A process according to claim 3 wherein 100 Z' is mesyloxy or tosyloxy and X is 0.
  5. A process according to claim 3 wherein Z' is chloro, bromo or iodo and X is 0 and wherein the subsequent oxazolidone ring opening step is effected in the presence of 105 an alkali metal hydroxide.
  6. 6 A process according to any one of claims 3, 4 or 5 wherein the compound of 1,598,668 5 formula IV is produced by introducing a group Z' into a compound of formula V HO.CH 2 CH CH 2 1, N-R 1 II X V wherein X and R, are as defined in claim 1.
  7. 7 A process according to claim 6, wherein the compound of formula V is produced by a process comprising intramolecularly cyclising a compound of formula VI HOCH 2-CH(OH)-CH 2 N Ri C(=X)-R 2 VI wherein R 1 and X are as defined in claim 1 and R 2 is a leaving group.
  8. 8 A process according to claim 7, wherein the compound of formula VI is produced by a process comprising splitting off the protecting group A from a compound of formula VII H 2-CH-CH 2-NR 1-C (=X) -R 2 0 \ O A VII wherein R, and X are as defined in claim 3, R 2 is a leaving group and A is a protecting group.
  9. 9 A process according to claim 8, wherein X is O and A is isopropylidene.
  10. A process as claimed in claim 1 substantially as hereinbefore described with reference to any one of the Examples.
  11. 11 A process according to any one of claims 1 to 10, wherein the compound produced is in racemic form.
  12. 12 A process according to any one of claims 1 to 10 wherein the compound produced is in S optically active form.
  13. 13 A process according to any one of claims 1 to 12, wherein the compound produced is in free base form.
  14. 14 A compound of formula I as defined in claim 1 or an ester thereof, whenever obtained by a process of any one of claims 1 to 13.
  15. A compound of formula I, wherein Ar is indol 4 yl and R 2 is isopropyl, whenever produced by a process of any one of claims 1 to 13.
  16. 16 A compound of formula II as defined in claim 1 in optically active or racemic form.
  17. 17 A compound of formula I as stated in claim 1, whenever produced by a process as claimed in claim 8.
    B A YORKE & CO, Chartered Patent Agents, 98 The Centre, Feltham, Middlesex TW 13 4 EP Agents for the applicants.
    Printed for Her Majesty's Stationery Office, by the Courier Press, Leamington Spa, 1981 Published by The Patent Office, 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
    1,598,668
GB20036/80A 1977-03-24 1978-03-21 Indolyloxymethyl-2-oxazolidinone derivatives and their use in the preparation of 1-amino-3-(indolyloxy)-2-propanols Expired GB1598668A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH375477A CH635573A5 (en) 1977-03-24 1977-03-24 Process for preparing novel 1,2-dihydroxypropane derivatives

Publications (1)

Publication Number Publication Date
GB1598668A true GB1598668A (en) 1981-09-23

Family

ID=4262769

Family Applications (2)

Application Number Title Priority Date Filing Date
GB11113/78A Expired GB1598667A (en) 1977-03-24 1978-03-21 1,3-dioxolane derivatives and their use in the preparation of 1-amino-3-aryloxy-2-propanols
GB20036/80A Expired GB1598668A (en) 1977-03-24 1978-03-21 Indolyloxymethyl-2-oxazolidinone derivatives and their use in the preparation of 1-amino-3-(indolyloxy)-2-propanols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB11113/78A Expired GB1598667A (en) 1977-03-24 1978-03-21 1,3-dioxolane derivatives and their use in the preparation of 1-amino-3-aryloxy-2-propanols

Country Status (8)

Country Link
JP (3) JPS53119824A (en)
BE (1) BE865201A (en)
CH (4) CH635573A5 (en)
DE (1) DE2810732A1 (en)
FR (1) FR2401148A1 (en)
GB (2) GB1598667A (en)
IT (1) IT1104182B (en)
NL (1) NL7802986A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070265451A1 (en) * 2001-10-18 2007-11-15 Board Of Trustees Of Michigan State University Process for the preparation of oxazolidinones and method of use thereof

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS577465A (en) * 1980-06-13 1982-01-14 Paamakemu Asia:Kk Preparation of indole derivative
JPS574969A (en) * 1980-06-13 1982-01-11 Paamakemu Asia:Kk Preparation of indole derivative
JPS5973223U (en) * 1982-11-06 1984-05-18 ブラザー工業株式会社 Jusa
JPS59227238A (en) * 1983-06-06 1984-12-20 Tetsuya Nishikura Rot-proof paste food and its preparation
DE3330005A1 (en) * 1983-08-19 1985-02-28 Wolfgang Dr. Graz Lindner TONIC ACID MONOESTERS OF OPTICALLY ACTIVE ALKANOLAMINES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE
JPS60261586A (en) * 1984-06-09 1985-12-24 Fuiruton Internatl Kk Method for removing metal, metallic ion, and organic chlorine from water
SE8404073D0 (en) * 1984-08-13 1984-08-13 Haessle Ab METHOD FOR THE SYNTHESIS OF PHARMACOLOGICALLY ACITVE COMPOUNDS AND INTERMEDIATES FOR SUCH SYNTHESIS
JPS61192268A (en) * 1985-02-19 1986-08-26 Yagira Suisan:Kk Preparation of boiled fish paste having taste and flavor of sushi
CH674843A5 (en) * 1988-01-26 1990-07-31 Lonza Ag
SE8801518D0 (en) * 1988-04-22 1988-04-22 Astra Pharma Prod A NOVEL PROCESS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH572924A5 (en) * 1972-04-19 1976-02-27 Frosst & Co Charles E Thiadiazole derivs - for treating angina pectoris
GB1435276A (en) * 1974-04-10 1976-05-12 Pfizer Ltd Oxazolidines and conversion to propanolamines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070265451A1 (en) * 2001-10-18 2007-11-15 Board Of Trustees Of Michigan State University Process for the preparation of oxazolidinones and method of use thereof

Also Published As

Publication number Publication date
CH640212A5 (en) 1983-12-30
JPS5716853A (en) 1982-01-28
CH635573A5 (en) 1983-04-15
JPS579781A (en) 1982-01-19
FR2401148B1 (en) 1983-01-28
GB1598667A (en) 1981-09-23
DE2810732A1 (en) 1978-09-28
CH639953A5 (en) 1983-12-15
JPS5730113B2 (en) 1982-06-26
IT7848559A0 (en) 1978-03-23
FR2401148A1 (en) 1979-03-23
CH642646A5 (en) 1984-04-30
BE865201A (en) 1978-09-22
IT1104182B (en) 1985-10-21
NL7802986A (en) 1978-09-26
JPS53119824A (en) 1978-10-19

Similar Documents

Publication Publication Date Title
FR2629819A1 (en) PROCESS FOR THE PREPARATION OF BACCATIN III AND DESACETYL 10 BACCATIN III DERIVATIVES
GB1598668A (en) Indolyloxymethyl-2-oxazolidinone derivatives and their use in the preparation of 1-amino-3-(indolyloxy)-2-propanols
EP0198348B1 (en) Process for preparing (+)s-2-hydroxy-2-methyl-hexanoic acid
US4403096A (en) Optically active imidazolidin-2-one derivatives
HU205116B (en) Process for producing 1,4-diazabicyclo/3.2.2./nonane
PT86258B (en) PREPARATION PROCESS OF IMIDAZOLE DERIVATIVES
EP0819112B1 (en) Oxidative process for preparing narwedine derivatives
JPH02188589A (en) Production of tri-lower alkanoyloxyboron
EP0006355B1 (en) Mixed anhydride steroid intermediate and process for preparing steroid intermediates
US4668822A (en) Method for preparing (+)S-2--hydroxy-2-methyl-hexanoic acid
KR950008971B1 (en) Preparation of alpha-n-chypoxanthin-9-yl)-pentyloxy(carbonyl)-arginine
US6407263B1 (en) Preparation of sulfo-N-hydroxy succinimide salts
US5202443A (en) Process for preparing 1-(2s)-3-mercapto-methyl-1-oxopropyl)-l-proline
US4170596A (en) Novel monoesters of cis-cyclopentenediol, process for preparation thereof, and process for preparation of lactones from the monoesters
US4238622A (en) D,L-2-Amino-4-(2-aminoethoxy)-trans-but-3-enoic acid derivatives
KR100209298B1 (en) Novel amino-cyclic compound
EP1015428B1 (en) Sulfo-n-hydroxy succinimide and method of preparation
SU461510A3 (en) Method for preparing alkylsulfonic acid esters of 1,3,2-oxazaphosphacyclic compounds
CA1162543A (en) Process for the preparation of apovincaminic acid esters
KR0141657B1 (en) Optically active 1-phenylpyrrolidone derivatives
US4217284A (en) Process for preparation of optically pure lactones from monoesters of cis-cyclopentenediol
US4459415A (en) Process for the preparation of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid
KR860001393B1 (en) Process for the preparation of 1-alkyl-2-oxo-4-acyl-1,2,3,4-tetrahydropyrazines
KR100196462B1 (en) Novel pyrrolidine derivatives and process for the preparations thereof
KR100684081B1 (en) Preparation of optically active 3,4-dihydrobenzoxazine derivative

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee