DE1668146B2 - N-substituierte S.S-Diphenyl-sulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung - Google Patents

N-substituierte S.S-Diphenyl-sulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung

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Publication number
DE1668146B2
DE1668146B2 DE1668146A DE1668146A DE1668146B2 DE 1668146 B2 DE1668146 B2 DE 1668146B2 DE 1668146 A DE1668146 A DE 1668146A DE 1668146 A DE1668146 A DE 1668146A DE 1668146 B2 DE1668146 B2 DE 1668146B2
Authority
DE
Germany
Prior art keywords
diphenyl
salts
substituted
sulfoximines
processes
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.)
Granted
Application number
DE1668146A
Other languages
English (en)
Other versions
DE1668146A1 (de
DE1668146C3 (de
Inventor
Gerhard Dr. 7803 Gundelfingen Satzinger
Peter Dipl.-Chem. Dr. 7802 Wildtal Stoss
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.)
GOEDECKE AG 1000 BERLIN
Original Assignee
GOEDECKE AG 1000 BERLIN
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 to DE1568734A priority Critical patent/DE1568734C3/de
Application filed by GOEDECKE AG 1000 BERLIN filed Critical GOEDECKE AG 1000 BERLIN
Priority to DE1668146A priority patent/DE1668146C3/de
Publication of DE1668146A1 publication Critical patent/DE1668146A1/de
Publication of DE1668146B2 publication Critical patent/DE1668146B2/de
Application granted granted Critical
Publication of DE1668146C3 publication Critical patent/DE1668146C3/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/56—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)

Description

Gegenstand des Hauptpatents 1568 734 sind N-DJaUcyl-aminoaUiyl-S^-dipbenyJsulfoxiranje und ihre Salze der allgemeinen Formel
QH5 R. Ra
= S = N-(CH2I-CH-N-R3
'5 1
C6H5
worin R1 und R2 Wasserstoff, Metbyi ader Äthyl, R3 und R4 Methyl oder Äthyl darstellen oder gemeinsam mit dem Stickstoffatom einen Piperidin-, Mmpholin- oder Pyrrolidinring bilden, η 1 oder 2 beden tet und X ein anorganisches oder organisches Anmü einer physiologisch verträglichen Säure darstellt, ins besondere das N-(2-DiäthyIaminoäthyl)-S,S-diphem i sulfoximinoxalat.
Ein weiterer Gegenstand des Hauptpaten! 1568 734 ist ein Verfahren zur Herstellung %.«:, N-substituierten Aminoalkyl - S,S - diphenyl - sul!.\ iminen sowie Salzen derselben der allgemeinen Fo-mel
QH5 Ri R2
i = S = N — (CH2Jn — CH — N — Rj QH5 R4
HX eine organische oder anorganische, pharmazeutisch verträgliche Säure darstellt.
2. Verfahren zur Herstellung von N-substituierlen S,S-Diphenyl-sulfoximinen und ihren Salzen der Formel
QH5
O«-S-»N — R-HX QH5
in weiterer Ausgestaltung des Patents 1 568 734, dadurch gekennzeichnet, daß man eine Suspension einer Diphenyl-sulfoximin-Alkalimetall· Verbindung in einem aromatischen Kohlenwasserstoff mit einem entsprechenden N-substituierten Aminohalogenalkan kondensiert und gegebenenfalls die Umsetzungsprodukte in üblicher Weise worin R, und R2 Wasserstoff oder einen niedernu.iekularen Alkylrcst bedeutet, R3 und R4 Alkyl·,..;c darstellen oder zusammen mit dem Stickstoffatom einen gesättigten, 5- oder 6gliedrigen heterocyclischen Ring bilden, π die ganze Zahl 1 oder 2 bedeutet und X ein anorganisches oder organisches Anion darstellt, das dadurch gekennzeichnet ist, daß man eine Suspension einer Diphenylsulfoximin-Alkali-Verbindung in einem aromatischen Kohlenwassersloff mit einem N-substituierten Aminohalogenalkan der Formel
HaI-(CH2Jn-CHR1-NR3R4
kondensiert und gegebenenfalls die Umsetzungsprodukte in üblicher Weise in ihre Salze oder in ihre Ammoniumsalze überführt. Das Verfahren des Häuptpatents I 568 734 ist weiterhin dadurch gekennzeichnet, daß man die Umsetzung vorzugsweise bei 110 bis 140" C durchführt.
Die Erfindung betrifft den in den Ansprüchen definierten Gegenstand. HX in der Formel verkör-
pert dabei eine organische oder anorganische, pharmazeutisch verträgliche Säure, wie z. B. Chlorwasserstoffsäure, Phosphorsäure, Schwefelsäure, Essigsäure, Zitronensäure, Weinsäure, Oxalsäure, Naphthalin-1,5-disulfonsäure.
Die erfindungsgemäßen Verbindungen !besitzen wertvolle pharmakologische Eigenschaften. Insbesondere besitzen sie eine im Versuchsbericht dargelegte hohe antispasmodische Aktivität.
AntispaemodHcbe Aktivität von
1 888 148
Versuchsbericht O
C6Hs-S=N-R-HX C6H5
R (CH2J2AnJ HX Musku-
Iotrope
spasrool.
Aktivität
a)		 AtUi-
Wst-
aroio-
Aktivität
a)		 Broncho-
spasmol.
Aktivität
b)		 ld»
(mg/kg)
ι
CH3 		Ha _ 40 3 400
CH2 C6H5
(CH2J2-N
CH3
(CH2J2-N N-CH2-C6H5 (HOOC-J2 1 10 400
Papaverin
Chloropyramin (HOOC-J2 — 2 — 450
HCl 1 1 1 500
HCl 45
Die Resultate nach a) wurden entsprechend der Methode von Magnus am isolierten Meerschweinchen-Ileum (Magnus in Ther. Grundlagen der Experimentellen Arzneimittelforschung, Wiss. Verlagsgesellschaft Stuttgart, 1965, S. 241), die nach b) entsprechend der Methode von K ο η ζ e 11 und Roessler, Arch. exp. Path. Phaimak. 195, 71 (1940), gewonnen. Verglcichssubstanzcn waren Papaverin und Chloropyramin (= Synpen).
Die folgenden Beispiele sollen die Erfindung weiter veranschaulichen.
Beispiel !
N-(3-Diäthylamino-2,2-dimethyl-propyI)-S,S-diphenyl-sulfoximin-naphthalin-l,5-disulfonat
0,1 Mol Diphenyl-sulfoximin-kalium werden mit 0,12 Mol l-Chlor-3-diäthylamino-2,2-dimethyl-propan in wasserfreiem Xylol gemäß dem Hauptpatent (Beispiel 4) umgesetzt. Reaktionszeit 16 Stunden.
Ausbeute: 22,2g Base, Kp.O4: 207 bis 2100C.
Durch Vereinigen einer Lösung der Base in Isopropanol mit einer Lösung von Naphthalin-1,5-disulfonsaure in dem gleichen Lösungsmittel gewinnt man das Naphthalin-l,5-disulfonat. Dieses wird durch Umkristallisieren aus Methanol gereinigt. Schmp. 232 bis 233° C.
Analyse: C31H38N2O7S3 (646,8).
Berechnet ... C 57,56, H 5,92, N 4,33, S 14,87;
gefunden .... C 57,58, H 5,89, N 4,40, S 14,64.
Beispiel 2
N-[2-( 1 -Methyl-2-piperidyl)-äthyl]-S,S-diphenylsulfoximin-naphthalin-l,5-disu!fonat
Die Darstellung erfolgt gemäß dem Hauptpatent (Beispiel 4) aus 0,1 Mol Diphenyl-sulfoximin-kalium und 0,15 Mol l-Methyl-2-(2-chloräthyl)-piperidin in wasserfreiem Xylol. Reaktionszeit 4 Stunden.
Ausbeute: 28 g Base, Kp.,,,,: 180 bis 2O5°C.
Auf üblichem Weg wird das Naphthalin-l,5-disulfonat bereitet und dieses aus n-Propanol/Wasser umkristallisiert. Die farblosen Blättchen schmelzen bei 185" C unter Umwandlung in farblose Nadeln. Diese zeigen einen Schmp. von 300C.
Analyse: C30H34N2O7S3 (630,8).
Berechnet ... C 57,12, H 5,43, N 4,45, S 15,25;
gefunden .... C 57,44, H 5,48, N 4,31, S 14,94.
Beispiel 3
N-[2-( 1 -Methyl-z-pyrrolidinylHthyO-^S-diphenylsulfoximin*naphthalin-l,5-disulfonat · H2O
Durch Umsetzung von 0,1 Mol Diphenyl-sulfox-
imin-natrium mit 0,1 Mol 1-Methyl-2-chloräthylpyrrolidin in wasserfreiem Xylol gemäß dem Haupt-
patent (Beispiel 1) (24 Stunden Reaktionszeit) gewinnt
man 23,4 g Base. Kp.002: 185 bis 2050C.
Das auf übliche Weise hergestellte Naphthalin-1,5-disulfonat wird aus Äthanol/Wasser umkristalli-
eiert. Ee enthalt I Mol Kristallwasser. Scbmp. 154 C/ IQO11C.
Analyse: Cj9H34N2O8S3 (634,8).
Berechnet ... C54.87, H 5,40. N4,41. S 15.15; gefonden .... C 54,96. H 5,57. N 4,59, S 15,20.
Beispiel 4
N-( 1 -Äthyl-3-piperidy l)-S,S-dipbenylsuKoximin-oxalat
0,1 MoI Dipbenyl-sulfoximin-natriu&j werden gemäß dem Hauptpatent (Beispiel 1) mit 0,12 Mol l-Äthyl-3-diIorpipendin in wasserfreiem Xylol umgesetzt. Reaktionszeit 5 Stunden.
Ausbeute: 22,5 g Base, Kp^1: 170 bis 190° C.
Das saure Oxalat wird wie üblich bereitet und aus Essigsäureäthylester/lsopropanol urakristallisierl. Schmp. 129,5 bis 130,5" C.
Analyse: C21H26N2O5S (418,5).
Berechnet ... C 60,26, H 6,26. N 6,69, S 7.66:
gefunden C 60.39, H 6,24, N 6,55. S 7.6S.
Beispiel 5
N-(l,3-Bis-dimethylamino-2-propyl)-S.S diphenylsulfoximin-dioxalat
0,1 Mol Diphenyl-sulfoximin-kalium werden mit 0,12 Mol !,S-Bis-dimethylamino^-chlorpropan in
wasserfreiem Xylol gemäß dem Hauptpatent (Beispiel 4) umgesetzt.
Ausbeute: 9,6 g Base, Kp^: J80 bis 190"C.
D&s auf übliche Weise bereitete Di-oxalat wird s aus Isopropanol umkristallisiert. Schmp. 155 bis 156 C.
Analyse: C23H31N3O9S.
Berechnet ... C 52.56, H 5,5 <, N 8,00. S 6.10;
,o gefunden .... C 52,52. H 5,71, N 8.02, S 6.25.
Beispiel 6
N-[2'(3-Azabicyclo[3^2]nonyl)-ätbyO-S.S-diphenyl-suIfoximin-hydrocblorid
0,1 MoI Diphenyl-sulfoximin-kalium werden mit 0,15 Mol 2-(3-Azabicyclo[3A2]nonylJ-äthyl-chJorid in wasserfreiem Xylol gemäß dem Hauptpatent (Beispiel 4) umgesetzt. Reaktionszeit 5 Stunden.
Die bei Kp^j: 195 bis 230" C destillierende Base (27,5 g) erstarrt in der Vorlage und wird aus Di'isopropyläther umkristallisiert. Schmp. 112'C.
Das Hydrochlorid win; wie üblich bereitet und aus Äthyl-methylketon umknstallisiert. Schmp. 215 bis 216CC.
Analyse: C22H29ClN2OS (405,0).
Berechnet:
C 65,24, H 7,22, Cl 8.75, N 6,92. S 7,92; *
gefunden:
C 65,21. H 7,20, Cl 8,89, N 7,06. S 8,19.

Claims (1)

1 666
Patentansprüche:
QH8
O*-S->N — R-HX QH5
worin R einen der folgenden Reste
CH3
— CH3 — C — CH2 — N(C2H5),
CH3
-(CH2J2-CH CH2
H3C — N CH2 CH2-CH2
-(CH2J2-CH CH2
CH3-N
^Γΐ2 ^Γΐ2
-CH-CH2 CH2 CH2
H3C — CH2 — N CH2
— CH — [CH2 — N(CH3J2],
/CH2-CH-— (CH2J2 — N
(CH2J2 \ jn ihre Safe» oder ihre quaternSren Ammoniumsalze TOh
I, N-substituierte S,S- Diphenyl -sulfoximine und ihre Salze der Formel s
DE1668146A 1966-12-22 1967-10-26 N-substituierte S,S-Diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung Expired DE1668146C3 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE1568734A DE1568734C3 (de) 1966-12-22 1966-12-22 N-Dialkyl-aminoalkyl-S-diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung
DE1668146A DE1668146C3 (de) 1966-12-22 1967-10-26 N-substituierte S,S-Diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEG0048828 1966-12-22
DE1668146A DE1668146C3 (de) 1966-12-22 1967-10-26 N-substituierte S,S-Diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung

Publications (3)

Publication Number Publication Date
DE1668146A1 DE1668146A1 (de) 1973-07-05
DE1668146B2 true DE1668146B2 (de) 1974-08-29
DE1668146C3 DE1668146C3 (de) 1975-06-19

Family

ID=32928441

Family Applications (2)

Application Number Title Priority Date Filing Date
DE1568734A Expired DE1568734C3 (de) 1966-12-22 1966-12-22 N-Dialkyl-aminoalkyl-S-diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung
DE1668146A Expired DE1668146C3 (de) 1966-12-22 1967-10-26 N-substituierte S,S-Diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE1568734A Expired DE1568734C3 (de) 1966-12-22 1966-12-22 N-Dialkyl-aminoalkyl-S-diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung

Country Status (1)

Country Link
DE (2) DE1568734C3 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2758613C2 (de) * 1977-12-29 1982-07-15 Gödecke AG, 1000 Berlin Sulfoximide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
GB9000303D0 (en) * 1990-01-06 1990-03-07 Pfizer Ltd Therapeutic agents

Also Published As

Publication number Publication date
DE1668146A1 (de) 1973-07-05
DE1568734C3 (de) 1974-03-28
DE1568734B2 (de) 1973-08-02
DE1568734A1 (de) 1970-03-05
DE1668146C3 (de) 1975-06-19

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