DK150851B - OXAZOLIDON- (2) COMPOUNDS FOR USING INTERMEDIATES FOR THE PREPARATION OF 4-AMINO-3,5-DIHALOGEN-PHENYLETHANOLAMINES - Google Patents
OXAZOLIDON- (2) COMPOUNDS FOR USING INTERMEDIATES FOR THE PREPARATION OF 4-AMINO-3,5-DIHALOGEN-PHENYLETHANOLAMINES Download PDFInfo
- Publication number
- DK150851B DK150851B DK086574AA DK86574A DK150851B DK 150851 B DK150851 B DK 150851B DK 086574A A DK086574A A DK 086574AA DK 86574 A DK86574 A DK 86574A DK 150851 B DK150851 B DK 150851B
- Authority
- DK
- Denmark
- Prior art keywords
- amino
- phenyl
- compounds
- oxazolidone
- preparation
- Prior art date
Links
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
150851150851
Opfindelsen angår hidtil ukendte oxazolidon-(2)-forbindelser til anvendelse som mellemprodukter til fremstilling af 4-amino-3,5-dihalogen-phenyletha-nolaminer med den i kravet angivne almene formel I, hvori Hal er ens og betegner et chloratom eller et bromatom, og R betegner et hydrogenatom eller en alkylgruppe med 1-5 carbonatomer, fortrinsvis methyl, ethyl, propyl, tert. butyl eller iso-pentyl, hvilke forbindelser er ejendommelige ved, at de har den i kravet angivne almene formel II, hvori Hal og R har den ovenfor angivne betydning.The invention relates to novel oxazolidone (2) compounds for use as intermediates in the preparation of 4-amino-3,5-dihalo-phenylethanolamines of the general formula I as claimed in which Hal is the same and represents a chlorine atom or a and R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably methyl, ethyl, propyl, tert. butyl or iso-pentyl, which compounds are characterized in that they have the general formula II as claimed, wherein Hal and R are as defined above.
Forbindelserne med formlen I er kendte forbindelser med farmaceutisk værdifulde egenskaber. Således har f.eks. N-alkyl-l-(4-amino-3,5-dihalogen-phenyl)ethanolaminerne, hvori alkylgruppen er methyl eller ethyl, analgetiske egenskaber, og de forbindelser, hvori alkylgruppen er tert. butyl eller iso- 2 150851 pentyl, har broneholytiske egenskaber.The compounds of formula I are known compounds having pharmaceutically valuable properties. Thus, e.g. The N-alkyl-1- (4-amino-3,5-dihalo-phenyl) ethanolamines wherein the alkyl group is methyl or ethyl, analgesic properties, and the compounds in which the alkyl group is tert. butyl or iso-pentyl, has broneholytic properties.
De hidtil ukendte forbindelser med den almene formel II kan fås ved halo-The novel compounds of general formula II can be obtained by halo-
genering af en oxazolidon med den almene formel IIIgenerating an oxazolidone of the general formula III
00
IIII
O N—RO N-R
HH2-™IIIHH2- ™ III
hvori R har den ovenfor angivne betydning, eller syreadditionssalte heraf i et opløsningsmiddel med mindst 2 mol brom eller chlor.wherein R has the meaning given above, or acid addition salts thereof, in a solvent having at least 2 moles of bromine or chlorine.
Halogeneringen kan udføres i et opløsningsmiddel såsom 50-100%'s eddikesyre eller i et halogeneret carbonhydrid,såsom chloroform,eller i en alkohol, såsom ethanol,og fortrinsvis ved temperaturer mellem 0 og 50°C.The halogenation may be carried out in a solvent such as 50-100% acetic acid or in a halogenated hydrocarbon such as chloroform or in an alcohol such as ethanol, and preferably at temperatures between 0 and 50 ° C.
De som udgangsmaterialer anvendte forbindelser med den almene formel III kan f.eks. opnås udfra de tilsvarende 4-nitrophenyl-ethanolaminer ved omsætning med phosgen og påfølgende reduktion af nitrogruppen.The compounds of general formula III used as starting materials may, for example, is obtained from the corresponding 4-nitrophenyl-ethanolamines by reaction with phosgene and subsequent reduction of the nitro group.
Udfra de omhandlede mellemprodukter fremstilles ethanolaminerne • med formel I ved sur eller alkalisk hydrolyse. Denne fremstilling er beskrevet i beskrivelsen til dansk patentansøgning nr. -5713/72.From the present intermediates, the ethanolamines of formula I are prepared by acidic or alkaline hydrolysis. This preparation is described in the specification for Danish Patent Application No. -5713/72.
Fra beskrivelsen til dansk patentansøgning nr. 4016/69, specielt Eksempel 9 deri, er det ganske vist kendt at fremstille substituerede phenyl-alkanolaminer, der er beslægtede med de her omhandlede slutprodukter med formlen I, ved sur eller alkalisk hydrolyse af de tilsvarende oxazolidon-(2)-forbindelser. I nævnte eksempel 9 beskrives fremstillingen af (-)-erythro-a-(l-aminoethyl)-m-(p-chlorbenzyloxy)-benzylalkohol ved alkalisk hydrolyse af optisk aktiv cis-5-(m-[p-chlorbenzyloxy]-4-methyl-2-oxazolidon, uden nogen udbytteangivelser. På denne baggrund kunne det imidlertid ikke forudses, at de her omhandlede oxazolidoner med formlen II kunne benyttes som mellemprodukter til ved sur eller alkalisk hydrolyse at fremstille 4-amino-3,5-dihalo-gen-phenylethanolaminer med formlen I, og at der herved ville opnås overordentlig gode udbytter, som tilfældet er, jf. nedenstående eksempel 2. Det er inden for kemien ikke muligt a priori simpelt hen at overføre en bestemt reaktion, som man ved forløber inden for en vis forbindelsesklasse, til en anden forbindelsesklasse, da andre substituenter, f.eks. i aromater, helt kan ændre totalmolekylets reaktivitet. I den nævnte ansøgning nr. 4016/69 er der tale om anvendelse af et aromat, der i m-stilling er substitueret med en p-chlorbenzyloxygruppe, medens der i det foreliggende tilfælde er tale om et mellemprodukt, der er substitueret med en aminogruppe i 4-stilling og med halogenatomer i 3- og 5-stillingerne. Fra litteraturen er det imidlertid kendt (se f.eks. Fieser og Fieser, side 625, 626 og 629), at der i det mindste 3 150851 ved alkalisk hydrolyse af aromater substitueret med halogenatomer må regnes med en dehalogenering. Fagmanden kunne derfor ikke vente, at de her omhandlede oxazolidoner i alkalisk miljø kunne hydrolyseres i næsten kvantitativt udbytte til 1~(4-amino-3,5-dihalogenphenyl)-ethanolaminer,Of course, from the specification of Danish Patent Application No. 4016/69, in particular Example 9 therein, it is known to prepare substituted phenyl-alkanolamines which are related to the end-products of formula I, by acidic or alkaline hydrolysis of the corresponding oxazolidone compounds. (2) compounds. In said Example 9, the preparation of (-) - erythro-α- (1-aminoethyl) -m- (p-chlorobenzyloxy) benzyl alcohol is described by alkaline hydrolysis of optically active cis-5- (m- [p-chlorobenzyloxy] -4 however, it could not be foreseen that the oxazolidones of formula II herein can be used as intermediates to produce 4-amino-3,5-dihalo by acid or alkaline hydrolysis. gene phenylethanolamines of formula I, and thus would achieve extremely good yields, as is the case, cf. Example 2 below. In chemistry, it is not possible simply to transfer a specific reaction, which is carried out in the course of a certain compound class, to another compound class, since other substituents, for example in aromatics, can completely change the reactivity of the total molecule. In said application No. 4016/69 there is the use of an aromatase which is in m position substituted with a p-chlorobenzyloxy group while they r in the present case is an intermediate substituted with an amino group at the 4-position and with halogen atoms at the 3- and 5-positions. However, from the literature it is known (see, for example, Fieser and Fieser, pages 625, 626 and 629) that at least 3 150851 by alkaline hydrolysis of aromatics substituted by halogen atoms a dehalogenation must be counted. Therefore, the person skilled in the art could not expect that the oxazolidones of this invention could be hydrolyzed in an almost quantitative yield to 1- (4-amino-3,5-dihalogenphenyl) ethanolamines,
Fremstillingen af mellemprodukterne med formel II og deres anvendelse til fremstilling af slutforbindelserne med formlen I belyses nærmere gennem henholdsvis de følgende eksempler 1 og 2.The preparation of the intermediates of formula II and their use in the preparation of the final compounds of formula I are elucidated by the following Examples 1 and 2, respectively.
Eksempel 1 5-(4-Amino-3,5-dibrom-phenyl)-3-tert. butyl-oxazolidon-(2).Example 1 5- (4-Amino-3,5-dibromo-phenyl) -3-tert. butyl oxazolidon- (2).
2,8 g 5-(4-amino-phenyl)-3-tert. butyl-oxazolidon-(2) (smeltepunkt 102-104°C) opløses i 50 ml iseddike og 2 ml vand, og under omrøring tilsættes dråbevis indenfor få minutter en opløsning af 3,9 g brom i 10 ml iseddike. Efter 15 minutter fortyndes reaktionsblandingen med 250 ml vand, der ekstraheres to gange med chloroform, og den organiske fase udrystes med vand, tørres med natriumsulfat og inddampes. Den tilbageværende rest opløses i en smule eddikeester, og 5-(4-amino-3,5-dibrom-phenyl)-3-tert. butyl-oxazolidon-(2) bringes til krystallisation ved tilsætning af petroleumsether.2.8 g of 5- (4-amino-phenyl) -3-tert. butyl-oxazolidone (2) (mp 102-104 ° C) is dissolved in 50 ml of glacial acetic acid and 2 ml of water and, with stirring, a solution of 3.9 g of bromine in 10 ml of glacial acetic acid is added dropwise within minutes. After 15 minutes, the reaction mixture is diluted with 250 ml of water extracted twice with chloroform and the organic phase is shaken with water, dried over sodium sulfate and evaporated. The residue is dissolved in a little vinegar ester and 5- (4-amino-3,5-dibromo-phenyl) -3-tert. butyl oxazolidone (2) is crystallized by the addition of petroleum ether.
Smeltepunkt 118,5-120°C.Melting point 118.5-120 ° C.
På samme måde opnås følgende yderligere forbindelser ved chlorering eller bromering: a) 5-(4-Amino-3,5-dichlor-phenyl)-3-tert. buty1-oxazolidon-(2).Similarly, the following additional compounds are obtained by chlorination or bromination: a) 5- (4-Amino-3,5-dichloro-phenyl) -3-tert. buty1-oxazolidon- (2).
Fremstillet ved chlorering af 5-(4-amino-phenyl)-3-tert. butyl-oxazoli-don-(2).Prepared by chlorination of 5- (4-amino-phenyl) -3-tert. butyl-oxazolidinone and jacking points (2).
Smeltepunkt 109-111°C.Mp 109-111 ° C.
b) 3-Ethyl-5-(4-amino-3,5-dibrom-phenyl)-oxazolidon-(2).b) 3-Ethyl-5- (4-amino-3,5-dibromo-phenyl) -oxazolidone- (2).
Fremstillet ved bromering af 3-ethyl-5-(4-amino-phenyl)-oxazolidon-(2), Smeltepunkt 112-113°C.Prepared by bromination of 3-ethyl-5- (4-amino-phenyl) -oxazolidone- (2), mp 112-113 ° C.
c) 5-(4-Amino-3,5-dibrom-phenyl)-3-methyl-oxazolidon-(2).c) 5- (4-Amino-3,5-dibromo-phenyl) -3-methyl-oxazolidone- (2).
Fremstillet ved bromering af 5-(4-amino-phenyl)-3-methyl-oxazolidon-(2). Smeltepunkt 95-97°C.Prepared by bromination of 5- (4-amino-phenyl) -3-methyl-oxazolidone- (2). Melting point 95-97 ° C.
d) 5-(4-Amino-3,5-dibrom-phenyl)-oxazolidon-(2).d) 5- (4-Amino-3,5-dibromo-phenyl) -oxazolidone- (2).
Fremstillet ved bromering af 5-(4-amino-phenyl)-oxazolidon-(2). Smeltepunkt 167-169,5°C.Prepared by bromination of 5- (4-amino-phenyl) -oxazolidone- (2). Melting point 167-169.5 ° C.
e) 5-(4-Amino-3,5-dichlor-phenyl)-oxazolidon-(2).e) 5- (4-Amino-3,5-dichloro-phenyl) -oxazolidone- (2).
Fremstillet ved chlorering af 5-(4-amino-phenyl)-oxazolidon-(2). Smeltepunkt 157-159¾.Prepared by chlorination of 5- (4-amino-phenyl) -oxazolidone- (2). Melting point 157-159¾.
150851 4150851 4
Eksempel 2 1-(4-Amino-3,5-dichlor-phenyl)-2-tert. butylamino-ethanol.Example 2 1- (4-Amino-3,5-dichloro-phenyl) -2-tert. butylamino-ethanol.
1 g (0,0033 mol) 5-(4-amino-3,5-dichlor-phenyl)-3-tert. buty1-oxazolidon- (2) opløses i 20 ml 2-propanol, og der tilsættes 2 ml vand og 2 g kaliumhydroxid. Den opstående tofasede opløsning koges 24 timer under tilbagesvaling, og derpå bringes l-(4-amino-3,5-dichlor-phenyl)-2-tert. butylamino-ethanol . til krystallisation ved tilsætning af noget ethanol og vand.1 g (0.0033 mol) 5- (4-amino-3,5-dichloro-phenyl) -3-tert. butyl 1-oxazolidone (2) is dissolved in 20 ml of 2-propanol and 2 ml of water and 2 g of potassium hydroxide are added. The resulting two-phase solution is refluxed for 24 hours, and then 1- (4-amino-3,5-dichloro-phenyl) -2-tert is brought. butylamino-ethanol. for crystallization by the addition of some ethanol and water.
Udbytte: 0,80 g (87,4% af det teoretiske).Yield: 0.80 g (87.4% of theory).
Smeltepunkt 116-119°C.Melting point 116-119 ° C.
Molekylvægt: 277,20 (C^H^Cl^O)Molecular Weight: 277.20 (C
Beregnet : G 52,01 H 6,55 N 10,10 Cl 25,57Calculated: G 52.01 H 6.55 N 10.10 Cl 25.57
Fundet : 51,70 6,40 9,85 25,00 På samme måde fremstilledes følgende forbindelser med den almene formel I ved hjælp af sur eller alkalisk hydrolyse af de tilsvarende oxazolidoner: a) 1-(4-Amino-3,5-dibrom-phenyl)-2-tert.-butylamino-ethanol.Found: 51.70 6.40 9.85 25.00 Similarly, the following compounds of general formula I were prepared by acidic or alkaline hydrolysis of the corresponding oxazolidones: a) 1- (4-Amino-3,5- dibromo-phenyl) -2-tert.-butylamino-ethanol.
Smeltepunkt af hydrochloridet 219,5-220°C (sønderdeling).Melting point of hydrochloride 219.5-220 ° C (decomposition).
Fremstillet ved alkalisk hydrolyse af 5-(4-amino-3,5-dibrom-phenyl)-3-tert. butyl-oxazolidon-(2).Prepared by alkaline hydrolysis of 5- (4-amino-3,5-dibromo-phenyl) -3-tert. butyl oxazolidon- (2).
v b) 2-Ethylamino-l-(4-amino-3,5-dibrom-phenyl)-ethanol.v b) 2-Ethylamino-1- (4-amino-3,5-dibromo-phenyl) -ethanol.
Smeltepunkt af hydrochloridet 174-175°C (sønderdeling).Melting point of the hydrochloride 174-175 ° C (dec.).
Fremstillet ved sur hydrolyse af 3-ethyl-5-(4-amino-3,5-dibrom-phenyl)-oxazo-lidon-(2).Prepared by acidic hydrolysis of 3-ethyl-5- (4-amino-3,5-dibromo-phenyl) -oxazo-lidone- (2).
c) 1-(4-Amino-3,5-dibrom-phenyl)-2-methylamino-ethanol.c) 1- (4-Amino-3,5-dibromo-phenyl) -2-methylamino-ethanol.
Smeltepunkt af hydrochloridet 210-216°C (sønderdeling).Melting point of hydrochloride 210-216 ° C (decomposition).
Fremstillet ved sur hydrolyse af 5-(4-amino-3,5-dibrom-phenyl)-3-methyl-oxazo-lidon-(2).Prepared by acidic hydrolysis of 5- (4-amino-3,5-dibromo-phenyl) -3-methyl-oxazo-lidone- (2).
d) 2-Amino-l-(4-amino-3,5-dibrom-phenyl)-ethanol.d) 2-Amino-1- (4-amino-3,5-dibromo-phenyl) -ethanol.
Smeltepunkt af hydrochloridet 214-216°C (sønderdeling).Melting point of hydrochloride 214-216 ° C (dec.).
Fremstillet ved alkalisk hydrolyse af 5-(4-amino-3,5-dibrom-phenyl)-oxazoli-don-(2).Prepared by alkaline hydrolysis of 5- (4-amino-3,5-dibromo-phenyl) -oxazolone- (2).
e) 2-Amino-l-(4-amino-3,5-dichlor-phenyl)-ethanol.e) 2-Amino-1- (4-amino-3,5-dichloro-phenyl) -ethanol.
Smeltepunkt af hydrochloridet 199-204°C (sønderdeling).Melting point of the hydrochloride 199-204 ° C (dec.).
Fremstillet ved alkalisk hydrolyse af 5-(4-amino-3,5-dichlor-phenyl)-oxazoli-don-(2).Prepared by alkaline hydrolysis of 5- (4-amino-3,5-dichloro-phenyl) -oxazoli-don- (2).
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2157040 | 1971-11-17 | ||
DE2157040A DE2157040A1 (en) | 1971-11-17 | 1971-11-17 | 4-amino-3,5-dihalophenylethanolamines prepn - by hydrolysis of 5-(4-amino-3,5-dihalo-phenyl)-2-oxazolidones |
Publications (1)
Publication Number | Publication Date |
---|---|
DK150851B true DK150851B (en) | 1987-07-06 |
Family
ID=5825380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK086574AA DK150851B (en) | 1971-11-17 | 1974-02-18 | OXAZOLIDON- (2) COMPOUNDS FOR USING INTERMEDIATES FOR THE PREPARATION OF 4-AMINO-3,5-DIHALOGEN-PHENYLETHANOLAMINES |
Country Status (16)
Country | Link |
---|---|
JP (2) | JPS5512893B2 (en) |
AT (2) | AT320618B (en) |
BG (1) | BG20337A3 (en) |
CA (1) | CA987685A (en) |
CH (1) | CH574903A5 (en) |
CS (1) | CS170454B2 (en) |
DD (2) | DD108297A5 (en) |
DE (1) | DE2157040A1 (en) |
DK (1) | DK150851B (en) |
ES (1) | ES408615A1 (en) |
HU (2) | HU164697B (en) |
PL (1) | PL79757B1 (en) |
RO (1) | RO68219A (en) |
SE (1) | SE405854B (en) |
SU (1) | SU468398A3 (en) |
YU (2) | YU35870B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2354961C2 (en) * | 1973-11-02 | 1983-02-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Process for the preparation of aminophenylethanolamines |
US5169633A (en) * | 1985-07-29 | 1992-12-08 | American Cyanamid Company | Continuous release phenylethanolamine derivative compositions |
US5059422A (en) * | 1985-07-29 | 1991-10-22 | American Cyanamid Company | Continuous release phenylethanolamine derivative compositions |
US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
WO2024153813A1 (en) | 2023-01-20 | 2024-07-25 | Atrogi Ab | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE704213A (en) * | 1966-09-22 | 1968-03-22 |
-
1971
- 1971-11-17 DE DE2157040A patent/DE2157040A1/en active Pending
- 1971-12-22 JP JP10453671A patent/JPS5512893B2/ja not_active Expired
-
1972
- 1972-11-07 AT AT943572A patent/AT320618B/en not_active IP Right Cessation
- 1972-11-07 AT AT1038373A patent/AT320642B/en not_active IP Right Cessation
- 1972-11-14 SU SU1847357A patent/SU468398A3/en active
- 1972-11-14 YU YU2815/72A patent/YU35870B/en unknown
- 1972-11-14 CH CH1654972A patent/CH574903A5/xx not_active IP Right Cessation
- 1972-11-15 DD DD174171*A patent/DD108297A5/xx unknown
- 1972-11-15 RO RO7272820A patent/RO68219A/en unknown
- 1972-11-15 HU HUTO893A patent/HU164697B/hu unknown
- 1972-11-15 DD DD166875A patent/DD103640A5/xx unknown
- 1972-11-15 HU HUTO936A patent/HU166034B/hu unknown
- 1972-11-15 BG BG021865A patent/BG20337A3/en unknown
- 1972-11-15 ES ES408615A patent/ES408615A1/en not_active Expired
- 1972-11-15 CS CS7736A patent/CS170454B2/cs unknown
- 1972-11-16 CA CA156,600A patent/CA987685A/en not_active Expired
- 1972-11-16 PL PL1972158883A patent/PL79757B1/pl unknown
-
1974
- 1974-02-18 DK DK086574AA patent/DK150851B/en not_active Application Discontinuation
-
1975
- 1975-05-14 SE SE7505550A patent/SE405854B/en not_active IP Right Cessation
-
1976
- 1976-10-14 JP JP12337176A patent/JPS5293767A/en active Granted
-
1979
- 1979-10-17 YU YU2525/79A patent/YU40763B/en unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE704213A (en) * | 1966-09-22 | 1968-03-22 |
Also Published As
Publication number | Publication date |
---|---|
RO68219A (en) | 1980-03-15 |
YU35870B (en) | 1981-08-31 |
SE405854B (en) | 1979-01-08 |
JPS5293767A (en) | 1977-08-06 |
JPS5422977B2 (en) | 1979-08-10 |
SE7505550L (en) | 1975-05-14 |
DD108297A5 (en) | 1974-09-12 |
JPS5512893B2 (en) | 1980-04-04 |
HU164697B (en) | 1974-03-28 |
YU252579A (en) | 1983-01-21 |
CH574903A5 (en) | 1976-04-30 |
SU468398A3 (en) | 1975-04-25 |
PL79757B1 (en) | 1975-06-30 |
ES408615A1 (en) | 1975-10-01 |
CA987685A (en) | 1976-04-20 |
JPS4857941A (en) | 1973-08-14 |
DE2157040A1 (en) | 1973-05-24 |
BG20337A3 (en) | 1975-11-05 |
HU166034B (en) | 1974-12-28 |
YU281572A (en) | 1981-02-28 |
AT320618B (en) | 1975-02-25 |
DD103640A5 (en) | 1974-02-05 |
YU40763B (en) | 1986-06-30 |
AT320642B (en) | 1975-02-25 |
CS170454B2 (en) | 1976-08-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DK150851B (en) | OXAZOLIDON- (2) COMPOUNDS FOR USING INTERMEDIATES FOR THE PREPARATION OF 4-AMINO-3,5-DIHALOGEN-PHENYLETHANOLAMINES | |
US9464063B2 (en) | Benzo [B] [1,4] oxazin derivatives as calcium sensing receptor modulators | |
CH627444A5 (en) | Method for producing new cyanessigsaeureanilid derivatives. | |
US2940969A (en) | 1-substituted-4-[3-(9-xanthylidene)-propyl] piperazines and 1-substituted-4-[3-(10-thiaxanthylidene) propyl]-piperazines | |
DK146006B (en) | PROCEDURE FOR PREPARING THE 2-AND-6 POSITION OF THE PHENYL RING SUBSTITUTED 2-PHENYLAMINO-2-IMIDAZOLINE DERIVATIVES OR SALTS THEREOF | |
JPS6296479A (en) | Polyfluoroalkylisoxazolylamine | |
DK154949B (en) | PROCEDURE FOR THE PREPARATION OF TRIFLUORMETHYLPHENOLS | |
JPS58219169A (en) | Oxazoleacetic acid derivative | |
NO144704B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 1-ALKYL-2- (PHENOXYMETHYL) -5-NITRO-IMIDAZOLES | |
US2679501A (en) | Amino derivatives of 2-substituted-4-tert. butylphenol ethers | |
US3331850A (en) | 5-(aryloxymethyl)-2-oxazolidinethiones | |
Musser et al. | N-[(arylmethoxy) phenyl] and N-[(arylmethoxy) naphthyl] sulfonamides: Potent orally active leukotriene D4 antagonists of novel structure | |
US4287348A (en) | Preparation of sulphoalkyl quaternary salts | |
JPS6044307B2 (en) | Novel O-alkylated oximes and their use as pharmaceuticals | |
Surrey et al. | New Amebacides. II. The Preparation of Some N-Alkyl-N-benzylhaloacetamides | |
DK145378B (en) | METHOD OF PREPARING 2,1,3-THIADIAZIN-4-ON-2,2-DIOXIDE DERIVATIVES | |
DK147707B (en) | 3-SUBSTITUTED 5- (2-HALOGENETHYL) -2-OXAZOLIDINONES USED AS INTERMEDIATES IN THE PREPARATION OF 5-SUBSTITUTED 2-OXAZOLIDINONES AND PROCEDURES FOR THE PREPARATION OF PREPARATION | |
DK173906B1 (en) | Phenylhydrazine intermediates and process for preparing them | |
US2532547A (en) | Z-aminoalkyl-glyoxaline derivatives | |
JP4161367B2 (en) | Process for producing 5-substituted oxazole compound and 5-substituted imidazole compound | |
DK145225B (en) | METHOD OF ANALOGUE FOR THE PREPARATION OF 1- (3-TRIMETHOXYPHENOXY-2-HYDROXY-PROPYL) -4-PHENYL-PIPERAZINE DERIVATIVES OR ACID ADDITION SALTS. | |
Kreling et al. | AMINO NITRILES: III. REACTION OF AMINO NITRILES WITH ISOTHIURONIUM SALTS | |
NO742960L (en) | ||
Brazier et al. | CCXLVIII.—The condensation of α-keto-β-anilino-αβ-diphenylethane and its homologues with phenylcarbimide and with phenylthiocarbimide | |
JPH05255271A (en) | Production of 3-hydroxymethyl-1-propargylimidazolidine-2,4-dione |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PHB | Application deemed withdrawn due to non-payment or other reasons |