DE1445583A1 - Process for the preparation of derivatives of 5-chloromethyl-oxazolidine - Google Patents
Process for the preparation of derivatives of 5-chloromethyl-oxazolidineInfo
- Publication number
- DE1445583A1 DE1445583A1 DE19631445583 DE1445583A DE1445583A1 DE 1445583 A1 DE1445583 A1 DE 1445583A1 DE 19631445583 DE19631445583 DE 19631445583 DE 1445583 A DE1445583 A DE 1445583A DE 1445583 A1 DE1445583 A1 DE 1445583A1
- Authority
- DE
- Germany
- Prior art keywords
- chloromethyl
- oxazolidine
- parts
- formula
- derivatives
- 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
Links
- 238000000034 method Methods 0.000 title claims description 6
- NQJMAAZEBNLAJX-UHFFFAOYSA-N 5-(chloromethyl)-1,3-oxazolidine Chemical class ClCC1CNCO1 NQJMAAZEBNLAJX-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- ILLXLIKVXGHEOL-UHFFFAOYSA-N 5-(chloromethyl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound NC1=NCC(CCl)O1 ILLXLIKVXGHEOL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000001773 anti-convulsant effect Effects 0.000 description 5
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UMURLIQHQSKULR-UHFFFAOYSA-N 1,3-oxazolidine-2-thione Chemical class S=C1NCCO1 UMURLIQHQSKULR-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- -1 m-chloroanilino Chemical group 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
"Verfahren zur Herstellung von Deri vaten des 5-Chlormethyloxazolidins" Zusatz zu Patent. ......... (Anmeldung C 22 520 IVb/12p) Es ist bekannt 5-Chlormethyl-oxazolidin-2-anilinothioformyl imid oder -allylaminothiorormylimid duroh Kochen einer alkoholischen Lösung von 5-Chlormethyl-oxazolidin-2-imid mit einer äquivalenten Menge Phenylisothiocyanat oder Allylisothiocyanat unter flUckfluß herzustellen. Die gleichen Verbindungen erhält man, wenn man die Umsetzung bei Raumtemperatur durchführt und das Reaktionsprodukt aus Alkohol umkristallisiert bzw. einige Zeit darin unter Rückfluß kocht."Process for the preparation of derivatives of 5-chloromethyloxazolidine" Addendum to patent. ......... (Application C 22 520 IVb / 12p) It is known 5-chloromethyl-oxazolidine-2-anilinothioformyl imide or allylaminothiorormylimide by boiling an alcoholic solution of 5-chloromethyl-oxazolidine-2-imide with an equivalent amount of phenyl isothiocyanate or to prepare allyl isothiocyanate under reflux. The same connections are obtained if the reaction is carried out at room temperature and the reaction product recrystallized from alcohol or refluxed in it for some time.
Gegenstand des Patentes ........ (Anmeldung C 22 520 IVb/12p} ist ein Verfahren zur Herstellung eines Derivates des 5-Chlormethyloxazolidins, das dadurch gekennzeichnet ist, daß 2-Imino-5-chlormethyl-oxazolidin mit einer äquimolekularen Menge Phenylisocyanat bei Temperaturen Uber etwa 40°C, gegebenenfalls in gegenwart eines Uber etwa 4Oc siedenden inerten Lösungsmittels umgesetzt wird.The subject of the patent ........ (Application C 22 520 IVb / 12p} is a process for the preparation of a derivative of 5-chloromethyl oxazolidine which is characterized in that 2-imino-5-chloromethyl-oxazolidine with an equimolecular Amount of phenyl isocyanate at temperatures above about 40 ° C, possibly in the presence an inert solvent boiling above about 40C is implemented.
In weiterer Ausbildung dieses Verfahrens wurde nun gefunden, daß man Derivate des 5-Chlormethyl-oxazolidins der Formel daurch herstellen kann, daß man 5-Chlormethyl-oxazolidinimid der Formel mit Verbindungen der Formel R - N C - Y, indder R einen mit Alkyl oder mit Halogen substituierten Phenylrest und Y.-Schwefel eder Sauerstoff bedeuten, bei Temperaturen über etwa 40°C, gegebenenfalls in Gegenwart eines über etwa 4o0c siedenden Lösungsmittels umsetzt.In a further development of this process it has now been found that derivatives of 5-chloromethyl-oxazolidine of the formula can thereby be prepared that 5-chloromethyl-oxazolidinimide of the formula with compounds of the formula R - NC - Y, indder R is an alkyl or halogen substituted phenyl radical and Y.-sulfur or oxygen, at temperatures above about 40 ° C, optionally in the presence of a solvent boiling above about 40 ° C.
Sofern die isocyanate flüssig sind, können die beiden Komponenten ohne Lösungsmittel miteinander vermischt und unter Feuchtigkeitsausschluß umgesetzt werden andernfalls arbeitet man mit einem inerten, über etwa 40°C siedenden Lösungsmittel, beispielsweise Benzol. Die Ausbeuten sind gut, mitunter quantitativ.Unless the isocyanate are liquid, the two components can be mixed with one another without a solvent and reacted with the exclusion of moisture, otherwise an inert solvent boiling above about 40 ° C., for example benzene, is used. The yields are good, sometimes quantitative.
Nach einer weiteren Ausführungsform des Verfahrens ist es möglich, die Umsetzung bei Raumtemperatur durchzuführen und dann das Reaktionsprodukt entweder aus einem Lösungsmittel oberhalb 40-C umzukristallisieren oder für sich auf Temperaturen über 4OC zu erwärmen. ~~ Die erfindungsgemäß hergestellten Verbindungen sind z.B. als Wachstumsregulatoren für P@lanzen verwendbar ; außerdem sind sie antikonvulsiv @irksam.According to a further embodiment of the method, it is possible carry out the reaction at room temperature and then either the reaction product recrystallize from a solvent above 40-C or by itself to temperatures to heat above 4OC. ~~ The compounds prepared according to the invention are e.g. can be used as growth regulators for plants; they are also anticonvulsant @effective.
Bo ist zwar bekannt, daß 2-Oxazolidone der Formel So ist die nach Beispiel 1 erhältliche Substanz bei geringerer Toxizität wesentlich wirksamer als (das relativ verwandte Trimetnadion. Der therapeutische Index DL50/DE50 ist; sogar wesentlich gUnstiger sls der des zur Zeit beztwirkenden Mittels, des Phenobarbitale.Bo is known that 2-oxazolidones of the formula The substance obtainable according to Example 1 is much more effective than (the relatively related trimetnadione. The therapeutic index DL50 / DE50 is; even significantly more favorable than that of the currently active agent, the phenobarbital, with lower toxicity.
Es ist zwar bekannt, daß 2-Oxazolidone der Formel in denen R einen gesättigten aliphatischen Substituenten bedeutet, antikonvulaiv wirken. Es ist auoh bekannt, daß bestimmte Oxazolidone, nämlich solche, die in 5-Stellung Aryloxymethylreste oder in 4-Stellung oder 5-Stellung aromatische Substituenten enthalten, antikonvulsiv wirksam sind. (Journal American Chemical 80o., Band 82 (1960), 166-1171, und Bend 73 (1951), 95 - 98). An der letztgenannten Stelle ist auch angegeben, daß die antikonvulsive Wirkung durch eine Carmabylierung gesteigert wird. Dabei ist jedoch die Natur der Substituenten in 4- und 5-Stellung von erheblicher Bedeiutung; das Vorhandensein von einer Phenylgruppe in 5-Stellung hat sich für die antikonvulsive Wirksamkeit als notwendig erwiesen. Schon die Gegenw@@ einer zweiten Phenylgruppe bewirkt, daB die Verbindung völlig unwirksam wird. Da an der letztgenannten Stelle (Seite 96) ausdrücklich angegeben wird, daß Verbindungen, die in 4-Stellung und/oder 5-Stellung aliphatische Suibstituenten enthalten, z.B. den 5-Chlormethylrest, entweder inaktive oder sehr wenig wirksam sind, ist die Tatsache, daß erfindungsgemäß erhaltene Verbindungen eine gute antikonvulsive Wirkung zeigen, in hohem Maße überraschend.It is known that 2-oxazolidones of the formula in which R is a saturated aliphatic substituent, have an anticonvulant effect. It is also known that certain oxazolidones, namely those which contain aryloxymethyl radicals in the 5-position or aromatic substituents in the 4-position or 5-position, are anticonvulsant. (Journal American Chemical 80o., Vol. 82 (1960), 166-1171, and Bend 73 (1951), 95-98). At the last-mentioned point it is also stated that the anticonvulsant effect is increased by carmabylation. However, the nature of the substituents in the 4- and 5-positions is of considerable importance; the presence of a phenyl group in the 5-position has been shown to be necessary for anticonvulsant effectiveness. Even the presence of a second phenyl group renders the compound completely ineffective. Since at the last-mentioned point (page 96) it is expressly stated that compounds which contain aliphatic substituents in the 4-position and / or 5-position, for example the 5-chloromethyl radical, are either inactive or very inactive, the fact is that Compounds obtained according to the invention show a good anticonvulsant effect, to a high degree surprisingly.
Es ist ferner bekannt, daß Oxazolidin-2-thione als Entblätterungs- -mittel und halogenfreie Oxazolidine als Pflanzenwachstumsregulatoren geeignet sind. Die Eignung der erfindungsgemäß als Wachstumsregulatoren vorgeschlagenen halogenhaltigen Produkte konnte daraus nicht hergeleitet werden.It is also known that oxazolidine-2-thiones are used as defoliation agents and halogen-free oxazolidines are suitable as plant growth regulators. The suitability of the halogen-containing substances proposed according to the invention as growth regulators Products could not be derived from it.
In den folgenden Beispielen sind Teile Gewichtsteile.In the following examples, parts are parts by weight.
Beispiel 1 12 Teile 5-Chlormethyl-2-imino-oxazolidin werden in 90 Teilen Toluol gelöst und in diese Lösung eine Mischung von 13, 35 Teilen m-Tolylisocyanat in 10 Teilen Toluol innerhalb von 5 Minuten zugetropft. Anschließend wird 3 Stunden auf dem Wasserbad erhitzt.Example 1 12 parts of 5-chloromethyl-2-imino-oxazolidine are used in 90 Parts of toluene dissolved and in this solution a mixture of 13.35 parts of m-tolyl isocyanate added dropwise in 10 parts of toluene within 5 minutes. Then 3 hours heated on the water bath.
Nach dem AbkUhlen wird diese Lösung von den am Kolben hartenden sirupösen Verunreinigungen durch Filtration befreit. Schon nach kurzer Zeit kristallisiert der N-(m-Tolyl)-N c-2-(5-ohlormethyloxazolidinyl)-harnstoff in Form weißer Nadeln aus. Nach der Umkristallisation aus Methanol schmilzt diese Verbindung von 144,5 - 145°C. Ausbeute 18,3 Teile, d.s. 75% der Theorie.After cooling, this solution becomes syrupy from the hardening on the flask Freed impurities by filtration. Crystallizes after a short time the N- (m-Tolyl) -N c-2- (5-chloromethyloxazolidinyl) -urea in the form of white needles the end. After recrystallization from methanol, this compound of 144.5 melts - 145 ° C. Yield 18.3 parts, d.s. 75% of theory.
Beispiel 2 4 Teile 2-Imino-5-chlormethyl-oxazolidin werden mit 4, 45 Teilen p-Tolylisocyanat vermischt und unter Feuchtigkeitsausschluß einige Stunden bei Zimmertemperatur. stehen gelassen. Dabei scheidet sich 2-(p-Toluidine-)-formylimid-9-ohlormethy-oxazolidin in Form einer festen Masse ab, die aus Aethanol umkristallisiert wird. F = 185°C.Example 2 4 parts of 2-imino-5-chloromethyl-oxazolidine are mixed with 4, 45 parts of p-tolyl isocyanate mixed and with exclusion of moisture for a few hours at room temperature. ditched. 2- (p-Toluidine -) - formylimide-9-chloromethy-oxazolidine separates in the form of a solid mass which is recrystallized from ethanol. F = 185 ° C.
Beispiel 3 4 Teile 2-Imino-5-chlormethyl-oxazolidin werden in 10 Teilen Toluol suspendiert und mit einer Lösung von 4,55 Teilen m-Chlorphenylisocyanat in 25 Teilen Toluol versetzt. Nach 20 Stunden wird das Lösungsmittel im Vakuum abgedampft und der feste Rückstand aus Aethanol umkristallisiert. Man erhält 6,1 Teile 2 (m-Chloranilino-) formylimld-5-ahlormethyl-OXazolidin in Form feiner, weiter Nadeln, F - 1610c.Example 3 4 parts of 2-imino-5-chloromethyl-oxazolidine are in 10 parts Suspended toluene and with a solution of 4.55 parts of m-chlorophenyl isocyanate in 25 parts of toluene are added. After 20 hours the solvent is evaporated off in vacuo and the solid residue is recrystallized from ethanol. 6.1 parts of 2 (m-chloroanilino) are obtained formylimld-5-ahlormethyl-OXazolidin in the form of fine, wide needles, F - 1610c.
Beispiel 4 4 Teile 2-Imino-5-chlormethyl-oxazolidin werden in 100 Teilen Toluol suspendiert und unter Kühlung 4,55 teile p-Chlorphenylisocyanat zugetropft. Nach einer Stunde wird mit Petroläther versetzt, wodruch daß Reaktionsprodukt ausfällt. Wird dieses Produkt erwärmt, so tritt bei 92 - 94°C Schmelzfluß ein.Example 4 4 parts of 2-imino-5-chloromethyl-oxazolidine are in 100 Parts of toluene are suspended and 4.55 parts of p-chlorophenyl isocyanate are added dropwise with cooling. After one hour, petroleum ether is added, causing the reaction product to precipitate. If this product is heated, melt flow occurs at 92-94 ° C.
Bei weiterem Erwärmen erstarrt es wieder, um bei 1940C endgültig zu schmelzen. Das 80 erhaltene 2-(p-Chloranilino-formuylimid)-5-chlormethyloxazolidin Bann aus Aethanol umkristallisiert werden.If heated further, it solidifies again, finally closing at 1940C melt. The 2- (p-chloroanilino-formuylimide) -5-chloromethyloxazolidine obtained Can be recrystallized from ethanol.
Claims (3)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0022520 | 1960-10-13 | ||
| DEC0022771 | 1960-11-19 | ||
| DEC0029097 | 1963-02-06 | ||
| DEC0029098 | 1963-02-06 | ||
| DEC0029096 | 1963-02-06 | ||
| DEC29099A DE1247318B (en) | 1960-10-13 | 1963-02-06 | Process for the preparation of N- [5-chloromethyloxazolinyl- (2)] thiourea derivatives |
| GB2988/64A GB1023386A (en) | 1960-10-13 | 1964-01-23 | Derivatives of 5-methyl-oxazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445583A1 true DE1445583A1 (en) | 1969-06-04 |
Family
ID=27561626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631445583 Pending DE1445583A1 (en) | 1960-10-13 | 1963-02-06 | Process for the preparation of derivatives of 5-chloromethyl-oxazolidine |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1445583A1 (en) |
| FR (1) | FR3206M (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2550198B2 (en) * | 1983-08-04 | 1985-10-11 | Cortial | NO- N (AMINOMETHYL-5 OXAZOLIN-2YL-2) N'-PHENYLUREES, THEIR PREPARATION METHOD AND THEIR THERAPEUTIC APPLICATION |
| FR2533923A1 (en) * | 1982-10-05 | 1984-04-06 | Cortial | New N-(5-aminomethyl-2-oxazolin-2-yl)-N'-phenylureas, method for preparing them and their therapeutic application |
| PT77429B (en) * | 1982-10-05 | 1986-02-27 | Cortial | PROCESS FOR THE PREPARATION OF NOVEL N- (AMINO-METHYL-5-OXAZOLIN-2-YL) -N-PHENYLUREES AND COMPOSITIONS CONTAINING SAME |
-
1963
- 1963-02-06 DE DE19631445583 patent/DE1445583A1/en active Pending
-
1964
- 1964-02-05 FR FR962708A patent/FR3206M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR3206M (en) | 1965-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |