DE1280873B - 3-sulfanilamido-4-methyl-isoxazole and process for its preparation - Google Patents

3-sulfanilamido-4-methyl-isoxazole and process for its preparation

Info

Publication number
DE1280873B
DE1280873B DEH53243A DEH0053243A DE1280873B DE 1280873 B DE1280873 B DE 1280873B DE H53243 A DEH53243 A DE H53243A DE H0053243 A DEH0053243 A DE H0053243A DE 1280873 B DE1280873 B DE 1280873B
Authority
DE
Germany
Prior art keywords
isoxazole
methyl
sulfanilamido
known per
manner known
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.)
Pending
Application number
DEH53243A
Other languages
German (de)
Inventor
Dr Hermann Bretschneider
Egon Fritz
Dr Wilhelm Kloetzer
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Priority claimed from CH970663A external-priority patent/CH421963A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of DE1280873B publication Critical patent/DE1280873B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/04—Preparatory processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
    • B01J10/02—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor of the thin-film type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B01J19/20—Stationary reactors having moving elements inside in the form of helices, e.g. screw reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B04—CENTRIFUGAL APPARATUS OR MACHINES FOR CARRYING-OUT PHYSICAL OR CHEMICAL PROCESSES
    • B04C—APPARATUS USING FREE VORTEX FLOW, e.g. CYCLONES
    • B04C5/00—Apparatus in which the axial direction of the vortex is reversed
    • B04C5/08—Vortex chamber constructions
    • B04C5/081—Shapes or dimensions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/14—Nitrogen atoms
    • C07D261/16—Benzene-sulfonamido isoxazoles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00094—Jackets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00168—Controlling or regulating processes controlling the viscosity

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Geometry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Polyamides (AREA)
  • Polymerisation Methods In General (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. CL:Int. CL:

Deutsche KL:German KL:

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

C07dC07d

A61kA61k

12p-3
30 h-2/3612p-3
30 h-2/36

P 12 80 873.0-44 (H 53243)P 12 80 873.0-44 (H 53243)

13. Juli 1964July 13, 1964

24. Oktober 1968October 24, 1968

Die Erfindung betrifft die Herstellung von 3-Sulfanilamido-4-methyl-isoxazol der Formel IThe invention relates to the production of 3-sulfanilamido-4-methyl-isoxazole of formula I.

sowie von dessen Salzen.as well as its salts.

Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß man 3-Amino-4-methyl-isoxazol der Formel IIThe process according to the invention is characterized in that 3-amino-4-methyl-isoxazole of formula II

H.C-C.
HCHC-C.
HC

-C-NH1 -C-NH 1

(H)(H)

Halogen — SO2 —* VHalogen - SO 2 - * V

(III)(III)

in an sich bekannter Weise mit einem Benzolsulfohalogenid der allgemeinen Formel IIIin a manner known per se with a benzenesulfohalide of the general formula III

in der R eine Acylamino-, Carbalkoxyamino-, Nitro- oder Azogruppe bedeutet, umsetzt und anschließend den Rest R in an sich bekannter Weise durch Hydrolyse oder Reduktion in die Aminogruppe umwandelt und das erhaltene 3-Sulfanilamido-4-methyl-isoxazol erwi.;;ischtcnfalls in an sich bekannter Weise mit ;mer basisch reagierenden Verbindung in ein Salz überführt.in which R is an acylamino, carbalkoxyamino, nitro or azo group, reacted and then converts the radical R into the amino group in a manner known per se by hydrolysis or reduction and the 3-sulfanilamido-4-methyl-isoxazole obtained exp. ;; is not included in a manner known per se ; mer basic reacting compound converted into a salt.

Die Umsetzung des 3-Amino-4-methyl-isoxazols mit dem Benzolsulfohalogenid kann z. B. in Pyridin bei Temperaturen im Bereich von etwa 0 bis 5O0C vorgenommen werden.The reaction of the 3-amino-4-methyl-isoxazole with the benzenesulfohalide can, for. B. in pyridine is carried out at temperatures ranging from about 0 to 5O 0 C.

Die Salzbildung kann beispielsweise mit anorganischen oder stärkeren organischen Basen, wie Alkali- oder Erdalkalihydroxyden oder -carbonaten. bzw. mit Aminen, wie Äthanolamin oder Diäthanoiamin, vorgenommen werden.The salt formation can, for example, with inorganic or stronger organic bases such as alkali or alkaline earth hydroxides or carbonates. or with amines such as ethanolamine or diethanoiamine.

Das erfindungsgemäß erhältliche 3-Sulfanilamido-4-methyl-isoxazol der Formel I zeichnet sich durch hohe chemotherapeutische Aktivität gegen die verschiedensten Infektionserreger aus, wie Escheriechia coil, Pneumokokken, Streptokokken, Staphylokokken und Salmonellen. So ist das 3-Sulfanilamido-4-methyl-isoxazol dem z. B. aus der deutschen Auslegeschrift 1 059 459 bekannten, isomeren 3-Sulfanilamido-5-methyJ-isoxazol chemotherapeutisch insofern überlegen, als es. bei vergleichbarer Toxizität. gegen Salmonella typhi murium dreimal aktiver ist.The 3-sulfanilamido-4-methyl-isoxazole obtainable according to the invention of formula I is characterized by high chemotherapeutic activity against the most diverse Infectious agents such as Escheriechia coil, pneumococci, streptococci, staphylococci and salmonella. So is the 3-sulfanilamido-4-methyl-isoxazole the z. B. from the German Auslegeschrift 1,059,459 known, isomeric 3-sulfanilamido-5-methyJ-isoxazole chemotherapeutically superior in that it is. with comparable toxicity. is three times more active against Salmonella typhi murium.

3-Sulfanilamido-4-methyl-isoxazol
und Verfahren zu seiner Herstellung3-sulfanilamido-4-methyl-isoxazole
and its method of manufacture

Anmelder:Applicant:

F. Hoffmann-La Roche & Co. Aktiengesellschaft, Basel (Schweiz)F. Hoffmann-La Roche & Co. Aktiengesellschaft, Basel (Switzerland)

Vertreter:Representative:

Dr. G. Schmitt, Rechtsanwalt,Dr. G. Schmitt, lawyer,

7850 Lörrach, Friedrichstr. 37850 Loerrach, Friedrichstr. 3

Als Erfinder benannt:Named as inventor:

Dr. Hermann Bretschneider, Innsbruck-Arzl;Dr. Hermann Bretschneider, Innsbruck-Arzl;

Egon Fritz,Egon Fritz,

Dr. Wilhelm Klötzer, Innsbruck (Österreich)Dr. Wilhelm Klötzer, Innsbruck (Austria)

Beanspruchte Priorität:Claimed priority:

Schweiz vom 6. August 1963 (9706)Switzerland of 6 August 1963 (9706)

Beispielexample

9,8 g (0,1 Mol) 3-Amino-4-methyl-isoxazol werden in 80 ml absolutem Pyridin gelöst. Zur Lösung gibt man 25,7 g p-Acetamino-benzolsulfochlorid. Man läßt dabei die Temperatur nicht über 450C steigen. Nach einer Stunde wird das Gemisch in 400 ml Eiswasser gegossen. Man erhält so das 3-(N-Acetylsulfanilamido)-4-methyl-isoxazol vom Schmelzpunkt 235° C. Dieses wird mit 10%iger Natronlauge auf dem siedenden Wasserbad verseift. Aus der filtrierten Lösung fällt das 3-Sulfanilamido-4-methyl-isoxazol reinweiß und kristallin aus. Ausbeute 15,7 g; Schmelzpunkt 182 bis 183 C (aus Methanol).9.8 g (0.1 mol) of 3-amino-4-methyl-isoxazole are dissolved in 80 ml of absolute pyridine. 25.7 g of p-acetaminobenzenesulfochloride are added to the solution. The temperature is not allowed to rise above 45 ° C. in the process. After one hour, the mixture is poured into 400 ml of ice water. This gives 3- (N-acetylsulfanilamido) -4-methyl-isoxazole with a melting point of 235 ° C. This is saponified with 10% strength sodium hydroxide solution on a boiling water bath. The 3-sulfanilamido-4-methyl-isoxazole precipitates in pure white and crystalline form from the filtered solution. Yield 15.7g; Melting point 182 to 183 ° C (from methanol).

Claims (2)

Patentansprüche:Patent claims: 1. 3-Sulfanilamido-4-methyl-isoxazol der Formel 1. 3-sulfanilamido-4-methyl-isoxazole of the formula 2. Verfahren zur Herstellung von 3-Sulfanilamido-4-methyl-isoxazol sowie von dessen Salzen,2. Process for the preparation of 3-sulfanilamido-4-methyl-isoxazole as well as its salts, IN 628/1675IN 628/1675 dadurch gekennzeichnet, daß. man 3 - Amino-4-methyl-isoxazol der Formel IIcharacterized in that. one 3 - amino-4-methyl-isoxazole of formula II H3C-C-HC H 3 CC-HC -C-NH3 N-C-NH 3 N (H)(H) in an sich bekannter Weise mit einem Benzolsulfohalogenid der allgemeinen Formel IIIin a manner known per se with a benzenesulfohalide of the general formula III IOIO Halogen —SQ2-Halogen —SQ 2 - (III) in der R eine Acylamino-, Carbalkoxyamino-, Nitro- oder Azogruppe bedeutet, umsetzt und anschließend den Rest R in an sich bekannter Weise durch Hydrolyse oder Reduktion in die Aminogruppe umwandelt und das erhaltene 3-Sulfanilamido-4-methyl-isoxazol erwünschtenfalls in an sich bekannter Weise mit einer basisch reagierenden Verbindung in ein Salz überführt.(III) in which R is an acylamino, carbalkoxyamino, nitro or azo group, converts and then the radical R in a manner known per se by hydrolysis or reduction into the Amino group and the resulting 3-sulfanilamido-4-methyl-isoxazole, if desired converted into a salt in a manner known per se with a basic compound. In Betracht gezogene Druckschriften:
Deutsche Auslegeschrift Nr. 1059 459;
R. C. Elderfield, Heterocyclic Compounds, Bd. 5 (1957), S. 473.Considered publications:
German Auslegeschrift No. 1059 459;
RC Elderfield, Heterocyclic Compounds, 5, 473 (1957). Bei der Bekanntmachung der Anmeldung ist ein Versuchsbericht ausgelegt worden.A test report was displayed when the registration was announced.
DEH53243A 1962-08-24 1964-07-13 3-sulfanilamido-4-methyl-isoxazole and process for its preparation Pending DE1280873B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US21932462A 1962-08-24 1962-08-24
CH970663A CH421963A (en) 1963-08-06 1963-08-06 Process for the preparation of aminoisoxazoles

Publications (1)

Publication Number Publication Date
DE1280873B true DE1280873B (en) 1968-10-24

Family

ID=25705221

Family Applications (3)

Application Number Title Priority Date Filing Date
DE19631520327 Pending DE1520327A1 (en) 1962-08-24 1963-08-21 Apparatus and process for the production of polycarbonamides
DE19641445902 Withdrawn DE1445902A1 (en) 1962-08-24 1964-07-03 Process for the preparation of aminoisoxazoles
DEH53243A Pending DE1280873B (en) 1962-08-24 1964-07-13 3-sulfanilamido-4-methyl-isoxazole and process for its preparation

Family Applications Before (2)

Application Number Title Priority Date Filing Date
DE19631520327 Pending DE1520327A1 (en) 1962-08-24 1963-08-21 Apparatus and process for the production of polycarbonamides
DE19641445902 Withdrawn DE1445902A1 (en) 1962-08-24 1964-07-03 Process for the preparation of aminoisoxazoles

Country Status (12)

Country Link
BE (3) BE651386A (en)
BR (2) BR6461413D0 (en)
CH (1) CH443229A (en)
DE (3) DE1520327A1 (en)
DK (1) DK113321B (en)
FR (2) FR1410207A (en)
GB (3) GB1011849A (en)
LU (1) LU44311A1 (en)
NL (4) NL144279B (en)
NO (1) NO115360B (en)
OA (1) OA00939A (en)
SE (3) SE321092B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4442260A (en) * 1983-03-14 1984-04-10 E. I. Du Pont De Nemours & Company Preparation of salt solution useful for making nylon
IL80260A0 (en) * 1986-10-09 1987-01-30 Bromine Compounds Ltd Process for the manufacture of 3-amino-5-methylisoxazole
GB2390314A (en) * 2002-07-02 2004-01-07 Protensive Ltd Reactor with rotating spiral member, and heat transfer member
DE10331952A1 (en) * 2003-07-15 2005-02-10 Degussa Ag Apparatus and process for discontinuous polycondensation
CN104829586B (en) * 2015-04-13 2018-06-15 泰兴市沃特尔化工有限公司 A kind of method and its cracker prepared by glycolide

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1059459B (en) * 1956-09-04 1959-06-18 Shionogi & Co Process for the preparation of the therapeutically useful 3-sulfanilamido-5-methylisoxazole

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1059459B (en) * 1956-09-04 1959-06-18 Shionogi & Co Process for the preparation of the therapeutically useful 3-sulfanilamido-5-methylisoxazole

Also Published As

Publication number Publication date
DK113321B (en) 1969-03-10
SE320368B (en) 1970-02-09
NL6408283A (en) 1965-02-08
FR3957M (en) 1966-02-28
BE651386A (en) 1965-02-04
SE321092B (en) 1970-02-23
BE636533A (en)
LU44311A1 (en) 1964-02-22
BE651387A (en) 1965-02-04
BR6461413D0 (en) 1973-08-09
NO115360B (en) 1968-09-23
DE1445902A1 (en) 1968-12-19
CH443229A (en) 1967-09-15
NL6408919A (en) 1965-02-08
BR6461412D0 (en) 1973-07-17
GB1050453A (en)
GB1011849A (en) 1965-12-01
NL132128C (en)
NL144279B (en) 1974-12-16
OA00939A (en) 1968-03-22
DE1520327A1 (en) 1969-05-22
NL297048A (en)
GB1011850A (en) 1965-12-01
SE300986B (en) 1968-05-20
FR1410207A (en) 1965-09-10

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