US3255207A - Quaternary ammonium salts containing anilido groups - Google Patents

Quaternary ammonium salts containing anilido groups Download PDF

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US3255207A
US3255207A US172077A US17207762A US3255207A US 3255207 A US3255207 A US 3255207A US 172077 A US172077 A US 172077A US 17207762 A US17207762 A US 17207762A US 3255207 A US3255207 A US 3255207A
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compound
anilide
compounds
formula
quaternary ammonium
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US172077A
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Aldo P Truant
Dahlbom Johan Richard
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AstraZeneca AB
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Astra AB
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Definitions

  • One object of the invention is to provide a new class of compounds which will control heart arrhythmias for relatively prolonged times.
  • Another object of the invention is to provide a new class of compounds which will control heart arrhythmias without producing undesirable side effects.
  • Still another object of this invention is to provide a new method of treating heart arrythmia.
  • Additional objects of this invention are to provide a method of synthesizing the compounds of this invention and new intermediate compounds useful in such synthesis.
  • the compounds hereinafter described are effective against arrhythmias. These new compounds are particularly valuable because they are effective for a relatively long duration, and they have an insignificant stimulating efiect on the nervous system.
  • the compounds of the present invention have the general formula:
  • a and B are the same or diiferent, straight or branched alkylene groups containing from 1 to 4 carbon atoms;
  • R and R are the same or difierent lower alkyl or, lower alkoxy groups.
  • n and m are integers from 0 to 3, inclusive.
  • Z is selected from the class consisting of C H3 ea Q0 ONE-C H2CH2-I: ⁇ T-C H C H2NHC o-@ 01 C H3 C Ha 69(1) Ha I @NELO 0.0 HzI' TC mo 0 .NH@ Br CHz.CHz.OCH3 I C H3 (B) C H3 C H;
  • the compounds of this invention may be manufactured where R, and R are the same or difierent alkyl groups 3,255,207 Patented June 7, 1966 having from 1 to 3 carbon atoms, and R is an alkylene group containing from 1 to 4 carbon atoms; and
  • X is the anion of a physiologically acceptable acid such as and the like.
  • lower alkyl and lower alkoxy groups are meant groups which contain no more than 5 carbon atoms.
  • Suitable compounds within the scope of the present invention are the following:
  • EXAMPLE 1 11.7 g. of diethylaminoaceto-Z,6-dimethyl anilide and 9.9 g. of chloroaceto-2,6-dimethyl anilide are dissolved in 25 ml. of xylene to which is added 0.1 g. of potassium iodide.
  • reaction product has a melting point of 224- 225 C. (decomposition). It is of the following formula CH CH3 a; I e NH-CO-CHrIf-OHz-CO-NH- 01 CzHs I CH3 CH3 (I)
  • EXAMPLE 2 A solution of 10.3 g. dimethylaminoaceto-2,6-dimethyl anilide and 9.9 g. of chloraceto-2,6-dimethyl anilide in 25 ml. of xylene to which is added 0.15 g.
  • EXAMPLE 3 In an analogous way 12 g. of dimethylaminoaceto-Zfidimethyl anilide and 9.9 g. of chloraceto anilide are reacted in 25 ml. of xylene. The reaction product is purified by recrystallization from ethanol-ether. The substance melts at 143144 C. under decomposition and has the following formula I CH3 6 I @NHCOCHzlTICHzCO-NH- 01 on. CH3
  • the quaternary salt formed has the following formula C H3 0 H3 I C Ha ea I @NH-CO-C H2-IIIC H-C own-Q 01 C Ha (V) EXAMPLE 6
  • the following compound is prepared I CH3 CH C H3 (VH1) This compound melts at 2142l6 C. under decomposition.
  • the crystal mass precipitated on cooling is purified by recrystallization from ethanol-ether, leaving a product with the melt- 6 ing point 210-211 C. under decomposition and has the followingformula usefulness of the compounds thus prepared, tests have been made on their antiarrhythmia action in dogs accord ing to Harris (A. S. Harris, Circulation I (1950), 1318).
  • column (a) gives the dose necessary for the elimination of arrhythmias of the sinus rhythm in unanesthetized coronary dogs
  • column (b) gives the dose which produces a prolongation of the duration of the electrocardiographically determined PQRS-complex, which means the dose .that diminishes the impulse conduction velocity within the heart and thereby reduces the risk of ventricular fibrillation
  • column (c) gives the dose which produces a lowering of the blood pressure.
  • column (d) gives the dose necessary for alowering of the heart frequency in anesthetized vagotomized and thoracotomized dogs and cats;
  • column (2) gives the dose which causes a prolongation of the duration of the PQRS-complex and thereby prevents or shortens the auricular flutter caused by the application of an acetylcholine moistened cotton wad on the wall of the right auricle;
  • column (f) gives the amount of the particular compounds necessary fora lowering of the blood pressure.
  • the new compounds synthesized according to the prescut invention are valuable for the treatment of different CH3 kinds of heart arrhythmias arising from the auricular as CH3 Well as the ventricular part of the heart and may be ad- 8.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

United States Patent This invention relates to new compounds which are particularly useful for the treatment of heart arrhythmias. Previously it has been proposed to use procaine or procaineamide for the treatment of heart arrhythmias (D. L. Burstein, Anesthesiology 7 (1946), p. 113, and K. Berry et al., Am. J. Med. 11 (1951), p. 431). It
has, however, now been shown that those compounds are effective for only a short duration and that in case of overdosage they cause an undesired stimulation of the central nervous system combined with an undesired depressive action on the respiration and the cardiovascular system.
One object of the invention, therefore, is to provide a new class of compounds which will control heart arrhythmias for relatively prolonged times.
Another object of the invention is to provide a new class of compounds which will control heart arrhythmias without producing undesirable side effects.
Still another object of this invention is to provide a new method of treating heart arrythmia.
Additional objects of this invention are to provide a method of synthesizing the compounds of this invention and new intermediate compounds useful in such synthesis.
Other objects and advantages of the invention will become apparent from the following description.
According to the present invention, it has been discovered that the compounds hereinafter described are effective against arrhythmias. These new compounds are particularly valuable because they are effective for a relatively long duration, and they have an insignificant stimulating efiect on the nervous system.
The compounds of the present invention have the general formula:
where:
A and B are the same or diiferent, straight or branched alkylene groups containing from 1 to 4 carbon atoms;
R and R are the same or difierent lower alkyl or, lower alkoxy groups.
n and m are integers from 0 to 3, inclusive.
Z is selected from the class consisting of C H3 ea Q0 ONE-C H2CH2-I:\T-C H C H2NHC o-@ 01 C H3 C Ha 69(1) Ha I @NELO 0.0 HzI' TC mo 0 .NH@ Br CHz.CHz.OCH3 I C H3 (B) C H3 C H;
| omocoom @nnooemruo rnconn. 01
Cl Ha C H3 e @NELG 0.0 HzN--C H10 0 .NH.@
| 019 0 H3 C H3 G3(|J1':ia @NELC o .o HzN-C H 0 .NH@
CH3 CH3 on, on; I
I e| e NC 0.0 Hr-If-C 112-0 0 .NH 01 C Ha I o H; o H3 63 e CHrNH-G o-oHzJ -oHrc O.NH Cl C Ha i The compounds of this invention may be manufactured where R, and R are the same or difierent alkyl groups 3,255,207 Patented June 7, 1966 having from 1 to 3 carbon atoms, and R is an alkylene group containing from 1 to 4 carbon atoms; and
X is the anion of a physiologically acceptable acid such as and the like.
By lower alkyl and lower alkoxy groups are meant groups which contain no more than 5 carbon atoms.
Suitable compounds within the scope of the present invention are the following:
by means of a quatemization reaction either by reacting a compound of the formula:
with a compound of the formula:
or by reacting a compound of the formula:
I'M CAN-BD (B4) (1 1a)m (4) with a compound of the formula R X where R is either H or R Either of these reactions will form a compound of the generic formula 11 (R in The symbols are as hereinabove defined. When Z includes a heterocyclic ring the reaction between intermediates (2) and (3) must be used.
In addition, according to the present invention, certain intermediate compounds have been discovered. These compounds are secondary and tertiary amines having the same formula:
The symbols in the above formula are herein defined. These intermediates are particularly useful where a compound in which the substituents R and R on the quaternary nitrogen are different radicals. An illustrative compound within this class is N-bis-(2,6-dimethylphenylcarbamoylmethyl)-ethylamine having the general formula:
I CH3 The invention is illustrated by but not limited to the following examples.
EXAMPLE 1 11.7 g. of diethylaminoaceto-Z,6-dimethyl anilide and 9.9 g. of chloroaceto-2,6-dimethyl anilide are dissolved in 25 ml. of xylene to which is added 0.1 g. of potassium iodide.
The reaction mixture is refluxed for hours. After cooling, the precipitated crystal mass is suctioned off and washed with ether. After recrystallization from ethanolether, the reaction product has a melting point of 224- 225 C. (decomposition). It is of the following formula CH CH3 a; I e NH-CO-CHrIf-OHz-CO-NH- 01 CzHs I CH3 CH3 (I) EXAMPLE 2 A solution of 10.3 g. dimethylaminoaceto-2,6-dimethyl anilide and 9.9 g. of chloraceto-2,6-dimethyl anilide in 25 ml. of xylene to which is added 0.15 g. of potassium iodide is refluxed on oil bath for 7 hours. After cooling to room temperature the xylene is decanted off and the remaining semicrystalline substance is dissolved in ethanol. Through addition of dry ether the reaction product is precipitated in crystalline form and is further purified by a recrystallization from ethanol-ether. The product melts at 217- 218 C. under decomposition and has the formula given below 69 I QNH-CO-G m-l -o m-c0NH- 0 1 0 E3 H; on: 11)
EXAMPLE 3 In an analogous way 12 g. of dimethylaminoaceto-Zfidimethyl anilide and 9.9 g. of chloraceto anilide are reacted in 25 ml. of xylene. The reaction product is purified by recrystallization from ethanol-ether. The substance melts at 143144 C. under decomposition and has the following formula I CH3 6 I @NHCOCHzlTICHzCO-NH- 01 on. CH3
(III) EXAMPLE 4 19 g. of dimethylaminoaceto anilide and 17.8 g. of chloroaceto anilide are dissolved in 50 ml. of xylene and to this is added about 0.2 g. of potassium iodide. The reaction mixture is refluxed for 45 minutes. The crystal mass :formed is filtered off on the following day and is recrystallized from ethanol-ether. The pure substance melts at 172-173 C. under decomposition. The quaternary salt formed has the following formula C H3 0 H3 I C Ha ea I @NH-CO-C H2-IIIC H-C own-Q 01 C Ha (V) EXAMPLE 6 In an analogous Way, by reacting u-dimethylaminopropio-2,6-dimethyl anilide and chloroaceto-2,6-dimethy1 anilide, the following compound is prepared I CH3 CH C H3 (VH1) This compound melts at 2142l6 C. under decomposition.
EXAMPLE 7 Starting from dimethylaminoaceto-Z,G-dimethyl anilide and chloroaceto-2,4-dimethyl anilide, the compound S CH CH8? I CH3 CH3 e! a 0113 V 5 NHCOCHzNCHz-CO-NH o1 NHCOCH2I'\I-CH2-CONH CH3 01 I 4111:
(13H OCH: OCH: has 3 1X (XIV) is prepared. Its melting point is 177-178 C. under de- 10 EXAMPLE 12 composition after a recrystallization from ethanol-ether. To a solution of 1&0 g of N bis 6 dimethylpheny1 EXAMPLE 8 carbamoylmethyl)-ethylamine in 90 ml. of acetone is Starting from di-methylaminoaceto-2,4,6-t.rimethyl aniadded! 1111- Of a lution 0t methylbromide in acetone lide and chloroaceto-2,6-dimethyl anilide, the compound 15 .contammg of methvlhromlde P CH CH The reaction mixture is left at room temperature for 3 CH3 3 5 days during which time the reaction product is crystal- 6B! 'lized. The substance is filtered off and urified b 6 P Y Te CO CHHII CHTCO NH @0113 O1 crystallization in ethanol-ether. The pure product melts CH 0 CH3 3 Cl"H3 (X) at 194-195 C. under decomposition and is of the follow mg formula is prepared. The melting point is 183-184 C. under decomposition after a recrystallization from ethanol-ether. CH3 CH3 EXAMPLE 9 I 9 19.2 g. of dimethyl aminoaceto-2-rnethyl anilide and NH 0Q CH2 III CH"C()NH B19 18.8 g. of chloroaceto-2,6-dimethyl anilide are dissolved I 02H; 1 in 50 ml. of acetonitrile and then 0.2 g. of KI is added, CH3 CH3 (XV) and the mixture is boiled for 2.5 hours. The crystal mass which is precipitated on cooling is recrystallized in MPLE 13 ethanol-ether. The substance melts at 182184 C. under decomposition and is of the following structure 2 0f acdlmethylflm1I10b11tYY0-2,6-d1methy1 anilide and 8.5 g. of chloroaceto anilide are dissolved in 50 ml. (3H3 CH3 CH3 of xylene. To this is added 0.2 g. of KI and the mixture a; 1 e is reflux boiled for 1 hour. There is gradually separated T C1 an oil which crystallizes in the course of a day. The CH3 1 crystal mass formed is recrystallized in a mixture of dry OHa ethanol and dry ether. The product melts at 133-135 C.
(XI) and is of the formula CH; ar NHC OCHz-I;IC ran-o H. c1n o O-NH (:1
CH: (XVI) EXAMPLE 10 For an illustration of the pharmacological action and In an analogous way, starting from pyrrolidinoaceto- 2,6-dimethyl anilide and chloroaceto-2,6-dimethyl anilide, the following compound is prepared (XIII) To a solution of 11.9 g. of dimethylaminoaceto-Z,6-dimethoxy anilide and 11.5 gQof chloroaceto-2,6-dimethoxy anilide in ml. of xylene is added 0.2 g. of KI and the mixture is boiled under reflux for 1.5 hours. The crystal mass precipitated on cooling is purified by recrystallization from ethanol-ether, leaving a product with the melt- 6 ing point 210-211 C. under decomposition and has the followingformula usefulness of the compounds thus prepared, tests have been made on their antiarrhythmia action in dogs accord ing to Harris (A. S. Harris, Circulation I (1950), 1318). In Table I below, column (a) gives the dose necessary for the elimination of arrhythmias of the sinus rhythm in unanesthetized coronary dogs, column (b) gives the dose which produces a prolongation of the duration of the electrocardiographically determined PQRS-complex, which means the dose .that diminishes the impulse conduction velocity within the heart and thereby reduces the risk of ventricular fibrillation; and finally, column (c) gives the dose which produces a lowering of the blood pressure. In the same table, column (d) gives the dose necessary for alowering of the heart frequency in anesthetized vagotomized and thoracotomized dogs and cats; column (2) gives the dose which causes a prolongation of the duration of the PQRS-complex and thereby prevents or shortens the auricular flutter caused by the application of an acetylcholine moistened cotton wad on the wall of the right auricle; and finally column (f) gives the amount of the particular compounds necessary fora lowering of the blood pressure.
G9 NII-CO-C nrr r-om-co-rusr-{Don Table I Effective dose in mg/kg. (not Effective dose in mglkg.
anesthetized "cor. dogs) (anesthetized cats and/or dogs) Compound Number of Normaliz- Prolongu- Lowering Number Lowering Prolon- Lowering No. coronary ing of the tion of of the of cats of the gation of the dogs sinus the blood and/or heart Ire of the blood rhythm PQRS- pressure dogs quency PQRS- pressure cornpl. compl.
a b c d e f 1 If nothing else is mentioned this means cumulative doses administered within 4 to 7 hours. 2 Alterations in the magnitude amounting to at least 50% as compared to the controls. 3 Significant alterations could not be observed at the doses tested. 4 Single dose.
Some of the compounds synthetized have been tested 2. The compound to determine their toxicity. The results obtained are CH3 shown in Table II. I CH5 Table 11 Q a LD in mgJkg. body weight 0 H3 3. The compound Compound No. Mouse Rat Rabbit CH3 I CH 1v 11 11 1v Q I CH 5-7 12-25 7 4 h H3 50 125 100 17 T e compound 8 H; 2H0 Q IV=intravenously. H3 IP =intraperitoneally. LD 0=t11e dose that kills of the test animals. 5. The compound Investigations carried out show that these new comr- CH3 pounds neither block nor potentiate the action of sub- 9 stances afiecting the autonomic nervous system when administered in a dosage suflicient to suspend or prevent CH3 heart arrhythmias. Experiments carried out prove that 6 Th d the cardiovascular effects initiated by the quarternary 50 6 compoun compounds of the present invention are specific to heart CH: C C and peripheral blood vessels. I H3 For an evaluation of the importance of the length of the application time, compound No. IV was tested in CH3 coronary dogs. It appears from this that the injection a in the course of a five minute period of 8 to 10 mg./kg. 7 Th d body weight procured a considerable lowering of the e compoun blood pressure While this elfect did not .come forth if the 3 CH application time was prolonged to 35 to 45 minutes. 3
The new compounds synthesized according to the prescut invention are valuable for the treatment of different CH3 kinds of heart arrhythmias arising from the auricular as CH3 Well as the ventricular part of the heart and may be ad- 8. The compound ministered according to generally used methods in the 4 CH3 form of different preparation forms, as for instance, gran- I OH; ulates, capsules, tablets, suppositories, aerosols and solua tions and suspensions intended for parenteral as well as peroral use. CH3
We claim: 1. The compound 9. The compound CH3 CH3 CH3 ?2H5 I I CH -NH-c OCH -lTICHz-C ONH- 01 I 2 s I CH3 CH3 CHa ClHa 9 10. The compound l CH 11. The compound I C 2H5 C H3 13. The compound I CH 14. A compound having the formula wherein A and B are selected from the group consisting of straight and branched alkylenes having 1 to 4 carbon atoms; R and R are selected from the group consisting of lower alkyl, and lower alkoxy; n and m are integers from 0 to 3; Z is selected from the group consisting of 6 N and wherein R and R are alkyl having from 1 to 3 carbon atoms, and R is alkylene having from 1 to 4 carbon atoms; and X is the anion of a physiologically acceptable acid.
References Cited by the Examiner UNITED STATES PATENTS 2/1944 Martin et al 260562 9/1946 Kaplan 260-2472 X 6/1956 Sahyun et a1 260 -559 6/ 1956 Martin 260558 8/1959 Speeter et a1 260-558 10/ 1960 De Beer l67-65 5/1961 Topliss et a1. 16765 FOREIGN PATENTS 8/1948 Denmark.
NICHOLAS s. RIZZO, Primary Examiner. ROBERT L. PRICE, JOSE TOVAR, Assistant Examiners.

Claims (2)

10. THE COMPOUND
14. A COMPOUND HAVING THE FORMULA
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4051254A4 (en) * 2019-10-30 2023-12-13 Children's Medical Center Corporation Local anesthetics with selective-sensory nerve blockade
WO2025093589A1 (en) 2023-11-02 2025-05-08 Chiesi Farmaceutici S.P.A. Heteroaryl amide derivatives as sodium channel inhibitors
WO2025093590A1 (en) 2023-11-02 2025-05-08 Chiesi Farmaceutici S.P.A. Heteroaryl ester derivatives as sodium channel inhibitors

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2343071A (en) * 1937-07-14 1944-02-29 Firm Of J R Geigy A G Amino fatty acid derivatives and their manufacture
US2407703A (en) * 1942-04-10 1946-09-17 Onyx Oil & Chemical Company Amino amide compounds
US2751412A (en) * 1954-04-09 1956-06-19 Cutter Lab Nu-(hydroxyalkyl)-3-phenylsalicylamides
US2752393A (en) * 1950-04-21 1956-06-26 Variapat Ag Trifluoromethyl-imino-bisacetanilide ammonium salts
US2901507A (en) * 1955-04-18 1959-08-25 Upjohn Co Alkylaminoalkyl 2,4,6-trimethylbenzamide
US2955073A (en) * 1958-06-02 1960-10-04 Burroughs Wellcome Co Method of treating febrile convulsions
US2986573A (en) * 1961-01-18 1961-05-30 Schering Corp Method for the treatment of hypertension

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2343071A (en) * 1937-07-14 1944-02-29 Firm Of J R Geigy A G Amino fatty acid derivatives and their manufacture
US2407703A (en) * 1942-04-10 1946-09-17 Onyx Oil & Chemical Company Amino amide compounds
US2752393A (en) * 1950-04-21 1956-06-26 Variapat Ag Trifluoromethyl-imino-bisacetanilide ammonium salts
US2751412A (en) * 1954-04-09 1956-06-19 Cutter Lab Nu-(hydroxyalkyl)-3-phenylsalicylamides
US2901507A (en) * 1955-04-18 1959-08-25 Upjohn Co Alkylaminoalkyl 2,4,6-trimethylbenzamide
US2955073A (en) * 1958-06-02 1960-10-04 Burroughs Wellcome Co Method of treating febrile convulsions
US2986573A (en) * 1961-01-18 1961-05-30 Schering Corp Method for the treatment of hypertension

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4051254A4 (en) * 2019-10-30 2023-12-13 Children's Medical Center Corporation Local anesthetics with selective-sensory nerve blockade
US12454509B2 (en) 2019-10-30 2025-10-28 Children's Medical Center Corporation Local anesthetics with selective-sensory nerve blockade
WO2025093589A1 (en) 2023-11-02 2025-05-08 Chiesi Farmaceutici S.P.A. Heteroaryl amide derivatives as sodium channel inhibitors
WO2025093590A1 (en) 2023-11-02 2025-05-08 Chiesi Farmaceutici S.P.A. Heteroaryl ester derivatives as sodium channel inhibitors

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