DE1219036B - Process for the preparation of N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans or -tetrahydropyrans - Google Patents
Process for the preparation of N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans or -tetrahydropyransInfo
- Publication number
- DE1219036B DE1219036B DEK50880A DEK0050880A DE1219036B DE 1219036 B DE1219036 B DE 1219036B DE K50880 A DEK50880 A DE K50880A DE K0050880 A DEK0050880 A DE K0050880A DE 1219036 B DE1219036 B DE 1219036B
- Authority
- DE
- Germany
- Prior art keywords
- aminomethyl
- tetrahydropyrans
- trimethoxybenzoyl
- preparation
- methyl
- 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
- -1 N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003527 tetrahydropyrans Chemical class 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- CINJIXGRSTYIHP-UHFFFAOYSA-N oxolan-3-ylmethanamine Chemical class NCC1CCOC1 CINJIXGRSTYIHP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000126 substance Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GAZNVVBKELWTBC-UHFFFAOYSA-N 2,3,4-trimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1OC GAZNVVBKELWTBC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000002908 adrenolytic effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ALGAPMXFTBJIPJ-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(oxolan-2-ylmethyl)benzamide Chemical group COC1=C(OC)C(OC)=CC(C(=O)NCC2OCCC2)=C1 ALGAPMXFTBJIPJ-UHFFFAOYSA-N 0.000 description 1
- SVNBLYILNKAFQM-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione;sodium Chemical compound [Na].O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 SVNBLYILNKAFQM-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Description
Verfahren zur Herstellung von N-(3',4',5'-Trimethoxybenzoyl)-3-aminomethyl-tetrahydrofuranen bzw. -tetrahydropyranen Die Erfindung betrifft ein Verfahren zur Herstellung von N-(3',4',5'-Trimethoxybenzoyl)-3-aminomethyl-tetrahydrofuranen bzw. -tetrahydropyranen der allgemeinen Formel in der R1 und R2 einen niederen Alkylrest mit 1 bis 4 Kohlenstoffatomen, den Phenyl- oder Benzylrest oder ein Wasserstoffatom bedeuten, Ra ein Wasserstoffatom oder eine Methylgruppe bedeutet und n die Zahl 1 oder 2 darstellt.Process for the production of N- (3 ', 4', 5'-trimethoxybenzoyl) -3-aminomethyl-tetrahydrofurans or -tetrahydropyrans The invention relates to a process for the production of N- (3 ', 4', 5'-trimethoxybenzoyl) -3-aminomethyl-tetrahydrofurans or tetrahydropyrans of the general formula in which R1 and R2 represent a lower alkyl radical with 1 to 4 carbon atoms, the phenyl or benzyl radical or a hydrogen atom, Ra represents a hydrogen atom or a methyl group and n represents the number 1 or 2.
Es wurde gefunden, daß diese Verbindungen starke Wirkungen auf das zentrale und vegetative Nervensystem besitzen. Die Wirkungen auf das zentrale Nervensystem sind dämpfender Natur, und sie wurden gegenüber bekannten Verbindungen im Barbituratpotenzierungstest nach der von H 0 lt e n und L a r s e n in »Acta pharmacologica et toxicologica«, 12 (1956), S. 346 bis 363, beschriebenen Methode ermittelt. Hierbei wurde die zu prüfende Substanz in einer Dosis von 5010 der DL50 an weiße Mäuse subcutan verabreicht, nach einer halben Stunde den Tieren 100 mg 5-(cyclohexen-1-yl)-5-methyl-N-methylbarbitursaures Natrium appliziert und im Vergleich zu mit der Prüfsubstanz nicht vorbehandelten Tieren die Dauer des Schlafes gemessen. It has been found that these compounds have potent effects on the central and autonomic nervous systems. The effects on the central nervous system are of a depressant nature and were tested against known compounds in the barbiturate potentiation test according to that of H 0 lt e n and L a r s e n in "Acta pharmacologica et toxicologica", 12 (1956), pp. 346 to 363, described method determined. This became the test substance administered subcutaneously to white mice in a dose of 5010 of the DL50, after half an hour the animals received 100 mg of 5- (cyclohexen-1-yl) -5-methyl-N-methylbarbituric acid Sodium applied and compared to that which had not been pretreated with the test substance Animals measured the duration of sleep.
Die erhaltenen Ergebnisse sind in der folgenden Tabelle 1 zusammengestellt.
Tabelle 1
II = 3 - (3',4',5'-Trimethoxybenzoylaminomethyl)-3- äthyl-6-methyl-tetrahydropyran (Beispiel 2). II = 3 - (3 ', 4', 5'-trimethoxybenzoylaminomethyl) -3-ethyl-6-methyl-tetrahydropyran (Example 2).
III = 3-N- [3',4',5'-Trimethoxybenzoyl-(N-äthyl)-aminomethyl]-3-benzyl-5-methyl-tetrahydrofuran (Beispiel 3). III = 3-N- [3 ', 4', 5'-trimethoxybenzoyl- (N-ethyl) aminomethyl] -3-benzyl-5-methyl-tetrahydrofuran (Example 3).
IV = 3-N- [3',4',5'-Trimethoxybenzoyl-(N-benzyl)-aminomethyl]-3-butyl-5,5-dimethyl-tetrahydrofuran (Beispiel 4). IV = 3-N- [3 ', 4', 5'-trimethoxybenzoyl- (N-benzyl) aminomethyl] -3-butyl-5,5-dimethyl-tetrahydrofuran (Example 4).
V = N - (1etrahydro - furfuryl) -3,4,5- trimethoxybenzamid (bekannt aus der USA.-Patentschrift 3072650, Beispiel 3). V = N - (1etrahydro - furfuryl) -3,4,5-trimethoxybenzamide (known from U.S. Patent 3072650, Example 3).
VI = N- (2- Tetrahydropyranylmethyl)- 3,4,5- trimethoxybenzamid (bekannt aus der USA.-Patentschrift 3 072 650, Beispiel 1). VI = N- (2-tetrahydropyranylmethyl) - 3,4,5-trimethoxybenzamide (known from U.S. Patent 3,072,650, Example 1).
Aus den gefundenen Werten, wobei die positiven Zahlen eine Schlafverlängerung und die negative Zahl eine Schlafverkürzung bedeuten, geht hervor, daß die geprüften Verfahrensprodukte eine wesentlich bessere dämpfende Wirkung besitzen als die bekannten Verbindungen. From the values found, the positive numbers being a sleep extension and the negative number means a reduction in sleep, it can be seen that the tested Process products have a much better dampening effect than the known ones Links.
Außerdem zeigen beispielsweise die Substanzen II und III im Gegensatz zu den aus der USA.-Patentschrift 3 072650 bekannten Verbindungen einen beachtlichen adrenolytischen Effekt. Die adrenolytischen Werte wurden im Magnus-Bad an der isolierten Meerschweinchen-Samenblase gemessen (Methode von J. B r ü g g e r in »Helvetica physiologica acta«, 3, S. 117 bis 134 [1945], beschrieben) und als EDso-Werte graphisch ermittelt. Hierbei bedeutet der EDso-Wert diejenige Menge Substanz, welche die an der isolierten Meerschweinchen-S amenblase durch 1,6 y Adrenalin pro Kubikzentimeter Bad ausgelöste Kontraktion um 50°/o herabsetzt. In addition, for example, the substances II and III show in contrast to the compounds known from US Pat. No. 3,072,650 adrenolytic effect. The adrenolytic values were measured in the Magnus bath on the isolated Guinea pig seminal vesicle measured (method by J. B rü g ge r in »Helvetica physiologica acta «, 3, pp. 117 to 134 [1945]) and as ED 50 values determined graphically. The ED 50 value means the amount of substance which the isolated guinea pig semen vesicle by 1.6 y adrenaline per Cubic centimeter bath reduces the induced contraction by 50 per cent.
Die erhaltenen Ergebnisse sind in der Tabelle 2 zusammengestellt. The results obtained are shown in Table 2.
Tabelle 2
III = 3-N- [3',4',5'-Trirnethoxybenzoyl-(N-äthyl)-aminomethylj-3-benzyl-5-methyl-tetrahydrofuran (Beispiel 3). III = 3-N- [3 ', 4', 5'-trimethoxybenzoyl- (N-ethyl) -aminomethylj-3-benzyl-5-methyl-tetrahydrofuran (Example 3).
V = N - (Tetrahydro - furfuryl) - 3,4,5 - trimethoxybenzamid (bekannt aus der USA.-Patentschrift 3072650, Beispiel 3). V = N - (tetrahydrofurfuryl) - 3,4,5 - trimethoxybenzamide (known from U.S. Patent 3072650, Example 3).
VI = N- (2-Tetrahydropyranylmethyl)- 3,4,5- trimethoxybenzamid (bekannt aus der USA.-Patentschnft 3 072 650, Beispiel 1). VI = N- (2-tetrahydropyranylmethyl) - 3,4,5-trimethoxybenzamide (known from U.S. Patent 3,072,650, Example 1).
Die Verbindungen der oben angegebenen allgemeinen Formel werden erfindungsgemäß dadurch hergestellt, daß man 3,4,5-Trimethoxybenzoylchlorid in an sich bekannter Weise mit 3-Aminomethyltetrahydrofuranen bzw. -tetrahydropyranen der allgemeinen Formel in der R1, R2, R3 und n die oben angegebene Bedeutung besitzen, in Gegenwart von säurebindenden Mitteln umsetzt.The compounds of the general formula given above are prepared according to the invention by reacting 3,4,5-trimethoxybenzoyl chloride in a manner known per se with 3-aminomethyltetrahydrofurans or tetrahydropyrans of the general formula in which R1, R2, R3 and n have the meaning given above, is reacted in the presence of acid-binding agents.
Beispiel 1 Zu einer gekühlten und kräftig gerührten Mischung, die aus einer Lösung von 2,2 g Natriumhydroxyd in 50 ccm Wasser und einer Lösung von 7,15 g 5- Methyl -3- äthyl -3- aminomethyl - tetrahydrofuran in 100 ccm Äther besteht, wird eine Lösung von 11,5 g 3,4,5-Trimethoxybenzoylchlorid in 150 ccm Äther hinzugetropft. Das Ganze wird 2 Stunden gerührt, dann die ätherische Phase abgetrennt, diese mit Salzsäure und Wasser ausgeschüttelt, hierauf eingedampft und der erhaltene Rückstandv zweimal im Hochvakuum destilliert. Example 1 To a cooled and vigorously stirred mixture which from a solution of 2.2 g of sodium hydroxide in 50 ccm of water and a solution of 7.15 g of 5- methyl -3- ethyl -3- aminomethyl-tetrahydrofuran in 100 ccm of ether, a solution of 11.5 g of 3,4,5-trimethoxybenzoyl chloride in 150 cc of ether is added dropwise. The whole thing is stirred for 2 hours, then the ethereal phase is separated off, this with Extracted hydrochloric acid and water, then evaporated and the residue obtained v distilled twice in a high vacuum.
Das 3- (3',4',5' - Trimethoxybenzoylaminomethyl)-3-äthyl-5-methyl-tetrahydrofuran geht beim Kr.0,004 198 bis 200"C über. Die Verbindung konnte nicht kristallin erhalten werden; sie stellt ein glasig-zähes Produkt dar. Die Ausbeute beträgt 480/0 der Theorie. 3- (3 ', 4', 5 '- trimethoxybenzoylaminomethyl) -3-ethyl-5-methyl-tetrahydrofuran goes from 198 to 200 "C at Kr.0.004. The compound could not get crystalline will; it is a glassy, viscous product. The yield is 480/0 Theory.
Beispiel 2 Unter Rühren und Kühlung wird zu einer Mischung, bestehend aus einer Lösung von 8,8 g 2- Methyl -5- aminomethyl -5-äthyl - tetrahydropyran in 50 ccm Äther und einer Lösung von 2,2 g Natriumhydroxyd in 50 ccm Wasser, langsam eine Lösung von 12 g Trimethoxybenzoylchlorid in 70 com Äther hinzugetropft. Nach lstündigem Rühren wird die Ätherschicht abgetrennt, getrocknet, eingedampft und der erhaltene Rückstand destilliert. Es werden 12 g (610/0 der Theorie) 3-(3',4',5'-Trimethoxybenzoylaminomethyl)-3 -äthyl-6-methyl-tetrahydropyran vom Kp.o,03 207"C in Form eines harten, glasigen Produktes erhalten. Example 2 With stirring and cooling, a mixture is formed from a solution of 8.8 g of 2-methyl -5-aminomethyl -5-ethyl - tetrahydropyran in 50 cc of ether and a solution of 2.2 g of sodium hydroxide in 50 cc of water, slowly a solution of 12 g of trimethoxybenzoyl chloride in 70 com ether was added dropwise. To After stirring for 1 hour, the ether layer is separated off, dried, evaporated and the residue obtained is distilled. There are 12 g (610/0 of theory) 3- (3 ', 4', 5'-trimethoxybenzoylaminomethyl) -3 -äthyl-6-methyl-tetrahydropyran from Kp.o, 03 207 "C in the form of a hard, glassy Product received.
Beispiel 3 Unter Rühren und Kühlung wird zu einer Mischung, die aus einer Lösung von 1,4 g Natriumhydroxyd in 20 ccm Wasser und einer Lösung aus 8 g 2 - Methyl - 4 - (N - äthyl - aminomethyl) - 4 - benzyltetrahydrofuran in 50ccm Äther besteht, langsam eine Lösung von 8 g Trimethyloxybenzoylchlorid in 100 ccm Äther hinzugetropft. Nach einer SLt.unde wird die Ätherschicht abgetrennt, getrocknet, eingedampft und der erhaltene Rückstand destilliert. Es werden 9 g (610/0 der Theorie) 3-N-[3',4',5'-Trimethoxybenzoyl-(N-äthyl)-aminomethyl]-3-benzyl-5 -methyltetrahydrofuran vom Kp.o,1 240°C in Form eines harten, glasigen Produktes erhalten. Example 3 With stirring and cooling, a mixture consisting of a solution of 1.4 g of sodium hydroxide in 20 cc of water and a solution of 8 g 2 - methyl - 4 - (N - ethyl - aminomethyl) - 4 - benzyltetrahydrofuran in 50ccm Ether, slowly a solution of 8 g of trimethyloxybenzoyl chloride in 100 cc Ether added dropwise. After one hour the ethereal layer is separated, dried, evaporated and the residue obtained is distilled. It will be 9 g (610/0 of theory) 3-N- [3 ', 4', 5'-trimethoxybenzoyl- (N-ethyl) aminomethyl] -3-benzyl-5-methyltetrahydrofuran obtained from b.p., 1 240 ° C in the form of a hard, glassy product.
Beispiel 4 27,5 g 2,2- Dimethyl - 4 - (N - benzylaminomethyl)-4-butyl-tetrahydrofuran werden in 100 ccm Äther gelöst, die Lösung wird mit einer Lösung von 3,1 g Natriumhydroxyd in 50 ccm Wasser unterschichtet und das Ganze tropfenweise mit einer Lösung von 23 g Trimethoxybenzoylchlorid in 200 ccm Äther versetzt. Die Mischung wird 30 Minuten gerührt, dann die Ätherschicht abdekantiert, diese mit verdünnter Salzsäure ausgeschüttelt, getrocknet und hierauf eingedampft. Der erhaltene Rückstand wird dann destilliert. Das beim Kp.o,ool 210 bis 213"C übergehende Destillat wird anschließend aus siedendem Petroläther (50 bis 70"C) umkristallisiert. Es werden 23 g (500/0 der Theorie) 3-(N-[3',4',5'-Trimethoxybenzoyl] - N - benzylaminomethyl) -3- butyl-5,5-dimethyl-tetrahydrofuran vom F. 80 bis 81°C als weißes kristallines Produkt erhalten. Example 4 27.5 g of 2,2-dimethyl-4 - (N-benzylaminomethyl) -4-butyl-tetrahydrofuran are dissolved in 100 cc of ether, the solution is made with a solution of 3.1 g of sodium hydroxide layered in 50 ccm of water and the whole thing drop by drop with a solution of 23 g of trimethoxybenzoyl chloride were added to 200 cc of ether. The mixture is 30 minutes stirred, then decanted off the ether layer, shaken it out with dilute hydrochloric acid, dried and then evaporated. The residue obtained is then distilled. The distillate passing over at bp 210 to 213 ° C. is then made from boiling Petroleum ether (50 to 70 "C) recrystallized. 23 g (500/0 of theory) 3- (N- [3 ', 4', 5'-trimethoxybenzoyl] - N - benzylaminomethyl) -3-butyl-5,5-dimethyl-tetrahydrofuran with a melting point of 80 to 81 ° C obtained as a white crystalline product.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK50880A DE1219036B (en) | 1963-09-20 | 1963-09-20 | Process for the preparation of N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans or -tetrahydropyrans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK50880A DE1219036B (en) | 1963-09-20 | 1963-09-20 | Process for the preparation of N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans or -tetrahydropyrans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1219036B true DE1219036B (en) | 1966-06-16 |
Family
ID=7225791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK50880A Pending DE1219036B (en) | 1963-09-20 | 1963-09-20 | Process for the preparation of N- (3 ', 4', 5'-tri-methoxybenzoyl) -3-aminomethyl-tetrahydro-furans or -tetrahydropyrans |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1219036B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015505301A (en) * | 2011-11-29 | 2015-02-19 | ビボゾン インコーポレイテッド | Novel benzamide derivatives and uses thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072650A (en) * | 1961-02-17 | 1963-01-08 | American Cyanamid Co | Amides of 2-(aminomethyl)-oxacycloalkanes |
-
1963
- 1963-09-20 DE DEK50880A patent/DE1219036B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072650A (en) * | 1961-02-17 | 1963-01-08 | American Cyanamid Co | Amides of 2-(aminomethyl)-oxacycloalkanes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015505301A (en) * | 2011-11-29 | 2015-02-19 | ビボゾン インコーポレイテッド | Novel benzamide derivatives and uses thereof |
| EP2786986B1 (en) * | 2011-11-29 | 2018-02-28 | Vivozon, Inc. | Novel benzamide derivative and use thereof |
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