DE1231690B - Process for the preparation of N, N-dibenzyl sulfamides - Google Patents

Process for the preparation of N, N-dibenzyl sulfamides

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Publication number
DE1231690B
DE1231690B DES95069A DES0095069A DE1231690B DE 1231690 B DE1231690 B DE 1231690B DE S95069 A DES95069 A DE S95069A DE S0095069 A DES0095069 A DE S0095069A DE 1231690 B DE1231690 B DE 1231690B
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Prior art keywords
sulfamide
general formula
mol
benzyl
preparation
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Pending
Application number
DES95069A
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German (de)
Inventor
Dr William J Houlihan
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
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Publication date
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Publication of DE1231690B publication Critical patent/DE1231690B/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

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

C07cC07c

Deutsche KL: 12 ο-23/03 German KL: 12 ο -23/03

1231 690
S95069IVb/12o
19. Januar 1965
5. Januar 19671231 690
S95069IVb / 12o
January 19, 1965
5th January 1967

Die Erfindung betrifft Verfahren zur Herstellung von Ν,Ν-Dibenzylsulfamiden der allgemeinen For-The invention relates to a process for the preparation of Ν, Ν-dibenzyl sulfamides of the general formula

mel1 R R mel1 RR

N-SO2-NH2 IN-SO 2 -NH 2 I.

IOIO

RHRH

worin der Rest wahlweise für Wasserstoff oder Chlor stehen kann, und ist dadurch gekennzeichnet, daß man in an sich bekannter Weise
a) ein Ν,Ν-Dibenzylamin der allgemeinen Formelllwherein the remainder can optionally stand for hydrogen or chlorine, and is characterized in that one in a manner known per se
a) a Ν, Ν-dibenzylamine of the general formula

R RR R

2525th

NHNH

R HR H

mit Sulfamid umsetzt oderreacts with sulfamide or

b) ein Ν,Ν-Dibenzylamin der Formel II zuerst mit Sulfurylchlorid und die so erhaltene Verbindung der allgemeinen Formel IIIb) a Ν, Ν-dibenzylamine of the formula II first with sulfuryl chloride and the compound thus obtained of the general formula III

R RR R

Verfahren zur Herstellung von
Ν,Ν-DibenzylsulfamidenProcess for the production of
Ν, Ν-dibenzyl sulfamides

Anmelder:Applicant:

Sandoz A. G., Basel (Schweiz)Sandoz A. G., Basel (Switzerland)

Vertreter:Representative:

Dr. W. Schalk, Dipl.-Ing. P. Wirth,Dr. W. Schalk, Dipl.-Ing. P. Wirth,

Dipl.-Ing. G. E. M. DannenbergDipl.-Ing. G. E. M. Dannenberg

und Dr. V. Schmied-Kowarzik, Patentanwälte,and Dr. V. Schmied-Kowarzik, patent attorneys,

Frankfurt/M., Große Eschenheimer Str. 39Frankfurt / M., Große Eschenheimer Str. 39

Als Erfinder benannt:
Dr. William J. Houlihan,
Mountain Lakes, N. J. (V. St. A.)Named as inventor:
Dr. William J. Houlihan,
Mountain Lakes, NJ (V. St. A.)

Beanspruchte Priorität:Claimed priority:

V. St. v. Amerika vom 22. Januar 1964 (339 354),V. St. v. America January 22, 1964 (339 354),

vom 8. Dezember 1964dated December 8, 1964

(416 907)(416 907)

c) mindestens
Formel IVc) at least
Formula IV

Mol einerMole one

Verbindung derConnection of

R RR R

NH2 NH 2

N-SO2-Cl IIIN-SO 2 -Cl III

R RR R

R HR H

mit Ammoniak umsetzt, oderreacts with ammonia, or

als freie Base oder in Form eines Salzes mit 1 Mol Sulfamid in Gegenwart von Pyridin umsetzt. as a free base or in the form of a salt with 1 mol of sulfamide in the presence of pyridine.

Beim Verfahren gemäß Ausführungsform c) werden symmetrische Verbindungen erhalten, d. h. solche, in denen beide Benzylreste in einem Molekül gleich sind.In the method according to embodiment c) symmetrical connections are obtained, d. H. such, in which both benzyl radicals in one molecule are the same.

Eine Ausführungsform des erfindungsgemäßen Verfahrens besteht darin, daß man eine Verbindung der allgemeinen Formel II mit Sulfamid in Gegenwart eines tertiären Amins als Lösungsmittel auf Temperaturen zwischen 50 und 2500C, vorteilhafterweise zwischen 55 und 1250C, z. B. Rückflußtemperatur des Reaktionsgemisches,'erhitzt.One embodiment of the process according to the invention consists in that a compound of the general formula II with sulfamide in the presence of a tertiary amine as solvent is heated to temperatures between 50 and 250 ° C., advantageously between 55 and 125 ° C., e.g. B. reflux temperature of the reaction mixture 'heated.

Als tertiäre Amine können erfindungsgemäß beispielsweise Trialkylamine, Monoaryldialkylamine oderAccording to the invention, for example trialkylamines, monoaryldialkylamines or

609 750/430609 750/430

basische, stickstoffhaltige Heterocyclen, wie z. B. Pyridine, Chinoline und N-nied. Alkyl-pyrrole, verwendet werden.basic, nitrogen-containing heterocycles, such as. B. pyridines, quinolines and N-nied. Alkyl pyrroles are used will.

Die Ausgangsprodukte der allgemeinen Formel II sind entweder bekannt oder können so hergestellt werden, daß man Verbindungen der allgemeinen Formel IV (s. oben) mit Verbindungen der allgemeinen Formel VThe starting products of the general formula II are either known or can be prepared in this way be that one compounds of the general formula IV (see above) with compounds of the general Formula V

R RR R

J V J V

CH2 — ClCH 2 - Cl

R HR H

worin R die obige Bedeutung besitzt, in einem inerten organischen Lösungsmittel und in Gegenwart eines säurebindenden Agens umsetzt. Als säurebindendes Agens kann auch die Verbindung der allgemeinen Formel IV im Überschuß verwendet werden.wherein R has the above meaning, in an inert organic solvent and in the presence of one acid-binding agent converts. The compound of the general Formula IV can be used in excess.

Die erfindungsgemäß hergestellten Verbindungen der allgemeinen Formel I zeichnen sich durch einen primär stimulierenden Effekt auf das Zentralnervensystem aus, und zwar besonders das N,N-Dibenzylsulfamid. Diejenigen erfindungsgemäß hergestellten Verbindungen, deren Phenylreste durch mindestens 1 Chloratom substituiert sind, besitzen außerdem krampflösende und blutdrucksenkende Wirkung.The compounds of the general formula I prepared according to the invention are distinguished by a primary stimulating effect on the central nervous system, especially the N, N-dibenzylsulfamide. Those compounds prepared according to the invention whose phenyl radicals are at least 1 chlorine atom are substituted, also have antispasmodic and antihypertensive effects.

Die erfindungsgemäß hergestellten Verbindungen der allgemeinen Formel I, vor allem das N,N-Dibenzylsulfamid, sollen daher in der Therapie als Antidepressiva verwendet werden, die chlorsubstituierten Ν,Ν-Dibenzylsulfamide als Anticonvulsiva und das N-l^-Dichlorbenzyl-N-benzylsulfamid als blutdrucksenkendes Mittel. Die mittlere tägliche Dosis beträgt für das Ν,Ν-Dibenzylsulfamid zwischen 35 und 42 mg, für die anderen Verbindungen zwischen 200 und 350 mg.The compounds of general formula I prepared according to the invention, especially N, N-dibenzylsulfamide, should therefore be used in therapy as antidepressants that are chlorine-substituted Ν, Ν-dibenzylsulfamide as anticonvulsants and the N-l ^ -dichlorobenzyl-N-benzylsulfamide as antihypertensive agent. The mean daily dose for the Ν, Ν-dibenzylsulfamide is between 35 and 42 mg, for the other compounds between 200 and 350 mg.

In den nachfolgenden Beispielen, die die Ausführungen des Verfahrens erläutern, erfolgen alle Temperaturangaben in Celsiusgraden und sind unkorrigiert. In the following examples, which explain the implementation of the process, all are carried out Temperatures in degrees Celsius and are uncorrected.

Beispiel 1
Ν,Ν-Dibenzylsulfamidexample 1
Ν, Ν-dibenzylsulfamide

Eine Lösung von 21,7 g (0,11 Mol) Dibenzylamin und 9,6 g (0,1 Mol) Sulfamid in 40 ecm Pyridin wird unter Rühren am Rückfluß so lange erhitzt, bis keine Gasentwicklung mehr festzustellen ist. Das Lösungsmittel wird im Vakuum am Rotationsverdampfer entfernt und der viskose Rückstand aus Methanol— Wasser umkristallisiert. Das dabei erhaltene Ν,Ν-Dibenzylsulfamid hat einen Schmp. von 71,5 bis 74°.A solution of 21.7 g (0.11 mol) of dibenzylamine and 9.6 g (0.1 mol) of sulfamide in 40 ecm of pyridine becomes heated under reflux with stirring until no more gas evolution can be detected. The solvent is removed in vacuo on a rotary evaporator and the viscous residue from methanol- Recrystallized water. The Ν, Ν-dibenzylsulfamide obtained has a melting point of 71.5 to 74 °.

Beispiel 2
N-Benzyl-N-3,4-dichlorbenzylsulfamidExample 2
N-Benzyl-N-3,4-dichlorobenzylsulfamide

a) N-Benzyl-3,4-dichlorbenzylamina) N-Benzyl-3,4-dichlorobenzylamine

Eine Mischung, bestehend aus 107 g (1,0 Mol) Benzylamin, 78 g (0,4 Mol) <x,3,4-Trichlortoluol und 400 ecm absolutem Toluol, wird während 15 Stunden unter Rühren am Rückfluß erhitzt. Nach Abkühlung auf Raumtemperatur wird das ausgefallene Benzylamin-hydrochlorid abfiltriert. Das Filtrat wird im Vakuum am Rotationsverdampfer eingeengt und derA mixture consisting of 107 g (1.0 mol) of benzylamine, 78 g (0.4 mol) of <x, 3,4-trichlorotoluene and 400 ecm of absolute toluene is refluxed for 15 hours with stirring. After cooling down the precipitated benzylamine hydrochloride is filtered off to room temperature. The filtrate is in Vacuum concentrated on a rotary evaporator and the

Rückstand destilliert. Dabei erhält man das N-Benzyl-N-3,4-dichlorbenzylamin vom Sdp. 177 bis 1797 1,75 mm, n%° = 1,5935.Distilled residue. This gives N-benzyl-N-3,4-dichlorobenzylamine with a bp 177 to 1797 1.75 mm, n% ° = 1.5935.

b) N-Benzyl-N-3,4-dichlorbenzylsulfamidb) N-Benzyl-N-3,4-dichlorobenzylsulfamide

Eine Lösung von 13,2 g (0,05 Mol) N-Benzyl-N-3,4-dichlorbenzylamin und 7,0 g (0,07 Mol) Sulfamid in 100 ecm Pyridin wird unter Rühren so lange am Rückfluß erhitzt, bis keine Gasentwicklung mehr auftritt. Anschließend wird das Lösungsmittel am Rotationsverdampfer im Vakuum entfernt und der viskose Rückstand aus Methanol—Wasser umkristallisiert. Dabei erhält man das N-Benzyl-N-3,4-dichlorbenzylsulfamid vom Schmp. 95 bis 96°.A solution of 13.2 g (0.05 mol) of N-benzyl-N-3,4-dichlorobenzylamine and 7.0 g (0.07 mol) of sulfamide in 100 ecm of pyridine is stirred for so long heated under reflux until no more gas evolution occurs. Then the solvent is on The rotary evaporator was removed in vacuo and the viscous residue was recrystallized from methanol-water. This gives N-benzyl-N-3,4-dichlorobenzylsulfamide from m.p. 95 to 96 °.

Beispiel 3
N-Benzyl-N-2,4-dichlorbenzylsulfamidExample 3
N-Benzyl-N-2,4-dichlorobenzylsulfamide

a) N-Benzyl-N-2,4-dichlorbenzylamina) N-Benzyl-N-2,4-dichlorobenzylamine

Eine Mischung, bestehend aus 53,5 g (0,5 Mol) Benzylamin, 39 g (0,2 Mol) a,2,4-Trichlortoluol und 200 ecm Toluol, wird, wie im Beispiel 2, a) beschrieben, umgesetzt und aufgearbeitet. Das dabei erhaltene N-Benzyl-N-2,4-dichlorbenzylamin hat einen Sdp. von 178 bis 18170,4 mm, nf = 1,5930.A mixture consisting of 53.5 g (0.5 mol) of benzylamine, 39 g (0.2 mol) of a, 2,4-trichlorotoluene and 200 ecm of toluene is, as described in Example 2, a), reacted and worked up. The N-benzyl-N-2,4-dichlorobenzylamine obtained in this way has a boiling point of 178 to 18,170.4 mm, nf = 1.5930.

b) N-Benzyl-N-2,4-dichlorbenzylsuIfamidb) N-Benzyl-N-2,4-dichlorobenzyl sulfamide

Eine Lösung von 13,2 g (0,05 Mol) N-Benzyl-2,4-dichlorbenzylamin und 7,0 g (0,07 Mol) Sulfamid in 40 ecm Pyridin wird unter Rühren am Rückfluß so lange erhitzt, bis keine Gasentwicklung mehr zu beobachten ist. Anschließend wird das Lösungsmittel am Rotationsverdampfer im Vakuum entfernt und der viskose Rückstand aus Methanol—Wasser umkristallisiert. Das dabei erhaltene N-Benzyl-N-2,4-dichlorbenzylsulfamid hat einen Schmp. von 95,5 bis 97°A solution of 13.2 g (0.05 mol) of N-benzyl-2,4-dichlorobenzylamine and 7.0 g (0.07 mol) of sulfamide in 40 ecm of pyridine is refluxed with stirring Heated until no more gas evolution can be observed. Then the solvent removed on a rotary evaporator in vacuo and the viscous residue was recrystallized from methanol-water. The N-benzyl-N-2,4-dichlorobenzylsulfamide obtained has a melting point of 95.5 to 97 °

Beispiel 4
N,N-Bis-(2,4-dichlorbenzyl)-suIfamidExample 4
N, N-bis (2,4-dichlorobenzyl) sulfamide

Eine Lösung von 36,6 g (0,11 Mol) Bis-(2,4-dichlorbenzyl)-amin und 9,6 g (0,10 Mol) Sulfamid in 40 ecm Pyridin wird unter Rühren am Rückfluß so lange erhitzt, bis keine Gasentwicklung mehr zu beobachten ist. Anschließend wird das Lösungsmittel am Rotationsverdampfer im Vakuum entfernt, der viskose Rückstand aus Methanol—Wasser umkristallisiert und dabei das N,N-Bis-(2,4-dichlorbenzyl)-sulfamid erhalten. Schmp. 123 bis 124°.A solution of 36.6 g (0.11 mol) bis (2,4-dichlorobenzyl) amine and 9.6 g (0.10 mol) of sulfamide in 40 ecm of pyridine is refluxed with stirring heated for a long time until no more gas evolution can be observed. Then the solvent removed on a rotary evaporator in vacuo, the viscous residue recrystallized from methanol-water and thereby the N, N-bis (2,4-dichlorobenzyl) sulfamide obtained. 123 to 124 °.

Beispiel 5Example 5

N,N-Bis-(2,4-dichlorbenzyl)-sulfamidN, N-bis (2,4-dichlorobenzyl) sulfamide

Eine Mischung, bestehend aus 21,3 g (0,1 Mol) salzsaurem Salz von 2,4-Dichlorbenzylamin, 11,2 g (0,11 Mol) Triäthylamin, 4,8 g (0,05 Mol) Sulfamid und 150 ecm Pyridin, wird während 8 Stunden unter Rühren am Rückflußkühler erhitzt. Das Lösungsmittel wird anschließend am Rotationsverdampfer entfernt und der Rückstand mit 350 ecm Wasser gewaschen. Das wasserunlösliche Material wird aus Isopropanol umkristallisiert, das dabei erhaltene N,N - Bis - (2,4 - dichlorbenzyl) - sulfamid hat einen Schmp. von 123 bis 124° C.A mixture consisting of 21.3 g (0.1 mol) of the hydrochloric acid salt of 2,4-dichlorobenzylamine, 11.2 g (0.11 mol) of triethylamine, 4.8 g (0.05 mol) of sulfamide and 150 ecm of pyridine is under for 8 hours Stirring heated on the reflux condenser. The solvent is then used on a rotary evaporator removed and the residue washed with 350 ecm of water. The water-insoluble material is made from Isopropanol recrystallized, the N, N - bis (2,4 - dichlorobenzyl) sulfamide obtained has a Mp. From 123 to 124 ° C.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von N,N-Dibenzylsulfamiden der allgemeinen Formel I R RProcess for the preparation of N, N-dibenzylsulfamides of the general formula I. R R N-SO2-NH2 IN-SO 2 -NH 2 I. R HR H worin der Rest R wahlweise für Wasserstoff oder Chlor stehen kann, dadurch gekennzeichnet^ daß man in an sich bekannter Weisewherein the radical R can optionally stand for hydrogen or chlorine, characterized in ^ that one in a known manner a) ein Ν,Ν-Dibenzylamin der allgemeinen Formelll a) a Ν, Ν-dibenzylamine of the general formula NHNH IIII 3030th R HR H mit Sulfamid umsetzt oderreacts with sulfamide or 3535 b) ein Ν,Ν-Dibenzylamin der Formel II zuerst mit Sulfurylchlorid und die so erhaltene Verbindung der allgemeinen Formel IIIb) a Ν, Ν-dibenzylamine of the formula II first with sulfuryl chloride and the compound thus obtained of the general formula III N-SO2-Cl IIIN-SO 2 -Cl III R HR H mit Ammoniak umsetzt oderreacts with ammonia or c) mindestens 2 Mol eines Benzylamins der Formel IVc) at least 2 moles of a benzylamine of the formula IV R RR R CH2 — NH2 CH 2 - NH 2 R HR H als freie Base oder in Form eines Salzes mit 1 Mol Sulfamid in Gegenwart von Pyridin umsetzt.as a free base or in the form of a salt with 1 mole of sulfamide in the presence of pyridine implements. Bei der Bekanntmachung der Anmeldung ist ein Vergleichsversuch ausgelegt worden.When the application was announced, a comparison experiment was laid out.
DES95069A 1964-01-22 1965-01-19 Process for the preparation of N, N-dibenzyl sulfamides Pending DE1231690B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33935464A 1964-01-22 1964-01-22
US416907A US3318952A (en) 1964-01-22 1964-12-08 Dibenzylsulfamides

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US (1) US3318952A (en)
DE (1) DE1231690B (en)
ES (1) ES308359A1 (en)
FR (2) FR1451245A (en)
GB (1) GB1087601A (en)

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US5763569A (en) * 1991-08-23 1998-06-09 The Brigham And Women's Hospital, Inc Calcium receptor-active molecules
US5858684A (en) * 1991-08-23 1999-01-12 The Brigham And Women's Hospital, Inc. Method of screening calcium receptor-active molecules
US5962314A (en) * 1993-02-23 1999-10-05 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5981599A (en) * 1996-05-01 1999-11-09 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds
US6001884A (en) * 1991-08-23 1999-12-14 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6011068A (en) * 1991-08-23 2000-01-04 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6031003A (en) * 1991-08-23 2000-02-29 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
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US6031003A (en) * 1991-08-23 2000-02-29 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5763569A (en) * 1991-08-23 1998-06-09 The Brigham And Women's Hospital, Inc Calcium receptor-active molecules
US5858684A (en) * 1991-08-23 1999-01-12 The Brigham And Women's Hospital, Inc. Method of screening calcium receptor-active molecules
US6011068A (en) * 1991-08-23 2000-01-04 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6313146B1 (en) 1991-08-23 2001-11-06 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5962314A (en) * 1993-02-23 1999-10-05 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
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US6057346A (en) * 1994-12-12 2000-05-02 The United States Of America As Represented By The Department Of Health And Human Services Inhibition of retroviral LTR promoters by calcium response modifiers
US6342532B1 (en) 1996-05-01 2002-01-29 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds
US6710088B2 (en) 1996-05-01 2004-03-23 Nps Pharmaceuticals, Inc. Inorganic ion receptor-active compounds
US5981599A (en) * 1996-05-01 1999-11-09 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds

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Publication number Publication date
ES308359A1 (en) 1965-06-01
FR1451245A (en) 1966-01-07
US3318952A (en) 1967-05-09
FR4380M (en) 1966-08-29
GB1087601A (en) 1967-10-18

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