US3875205A - Cyanoalkyl substituted-3-oxo-alkamidines - Google Patents

Cyanoalkyl substituted-3-oxo-alkamidines Download PDF

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Publication number
US3875205A
US3875205A US366681A US36668173A US3875205A US 3875205 A US3875205 A US 3875205A US 366681 A US366681 A US 366681A US 36668173 A US36668173 A US 36668173A US 3875205 A US3875205 A US 3875205A
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methyl
carbon atoms
alkyl
bromide
ethyl
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US366681A
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English (en)
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Wilhelm Heffe
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Sandoz AG
Sandoz Wander Inc
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Sandoz AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms

Definitions

  • R is alkyl of 1 to 4 carbon atoms, phenyl or substituted phenyl,
  • R is alkyl of l to 4 carbon atoms
  • R and R together are (Cl-1 wherein n is an integer from 2 to 7, and
  • R is alkyl of 1 to 4 carbon atoms
  • R R and R together with the carbon atom to which they are bound form the adamantyl radical
  • R is alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof, cyanoalkyl wherein the alkyl radical is of 1 to 5 carbon atoms, or a group of formula wherein R and R are the same or different and each is alkyl of l to 4 carbon atoms, and
  • R,-, and R are the same or different and each is alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof or cyanoalkyl wherein the alkyl is of l to 5 carbon atoms, or one of R R and R is phenyl or substituted phenyl and the others of R R and, R are as defined above, provided at least one of,R R and R is cyanoalkyl wherein the alkyl is of 1 to 5 carbon atoms.
  • R is alkyl of 1 to 4 carbon atoms
  • R is alkyl of l to 4 carbon atoms
  • R and R together are -(CI-I wherein n is an integer from 2 to 7,
  • R is alkyl of l to 4 carbon atoms
  • R R and R together with the carbon atom to which they are bound form the adamantyl radical
  • R is alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof, cyanoalkyl wherein the alkyl radical is of l to 5 carbon atoms, or a group of formula phenyl or substiwherein R, and R are the same or different and each is alkyl of l to 4 carbon atoms, or
  • R and R together with the nitrogen atom are a heterocyclic ring, or a heterocyclic ring having a ring oxygen atom, and
  • R and R are the same or different and each is alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof or cyanoalkyl wherein the alkyl is of l to 5 carbon atoms, or one of R R and R is phenyl or substituted phenyl and the others of R R and R are as defined above.
  • the substituted phenyl group preferably is alkylphenyL'the alkyl radical having from 1 to 4 carbon atoms, especially methylphenyl, the alkyl substituent being preferably in the p position, or halophenyl, especially chlorophenyl, the.
  • halo substituent being preferably in the p position.
  • R and R together with the nitrogen atom are a heterocyclic ring, this is preferably a five or six membered heterocyclic ring, preferably saturated e.g. morpholine, pyrrolidine or piperazine.
  • a compound of formula I may be obtained by a process comprising desulphurizing a compound of formula II,
  • the process according to the invention may be effected in the presence of a desulphurizing agent, preferably triaryl derivatives, trialkyl derivatives or mixed alkyl/triaryl derivatives wherein each of the alkyl groups preferably is of 1 to 4 carbon atoms, of phosphorous, arsenic, antimony or bismuth, especially, however, of phosphorous or arsenic. Especially preferred are the phosphorus derivatives.
  • a desulphurizing agent preferably triaryl derivatives, trialkyl derivatives or mixed alkyl/triaryl derivatives wherein each of the alkyl groups preferably is of 1 to 4 carbon atoms, of phosphorous, arsenic, antimony or bismuth, especially, however, of phosphorous or arsenic.
  • phosphorus derivatives Especially preferred are the phosphorus derivatives.
  • Preferred examples of desulphurizing agents are triphenylphosphine or arsine and triethyl-phosphite.
  • the process according to the invention may be effected in the absence of a solvent or in an inert organic solvent, e.g. dimethyl formamide, dioxane or dimethyl acetamide.
  • the reaction is preferably effected in the absence of a solvent.
  • the reaction temperature may be from to C.
  • the reaction mixture may be acidified, e.g. with an acid capable of forming a water-soluble acid addition form of the compound of formula I, e.g. hydrobromic acid, the residue is conveniently filtered off and the resulting acid addition salt form of the compound of formula I is conveniently isolated from the resulting reaction mixture in known manner, e.g. by concentrating by evaporation, and may be purified, e.g. by recrystallization.
  • Free base forms of compounds of formula I may be converted into acid addition salt form in conventional manner, and vice versa.
  • suitable acids for acid addition salt formation are the hydrohalic acids such as hydrochloric and hydrobromic acid, or perchloric acid, and organic acids such as oxalic acid and maleic acid.
  • the compounds of formula 11, used as starting materials in the above process may be obtained by reacting a reactive ester of an alcohol of formula Ill,
  • Suitable reactive esters of the alcohol of formula III include esters of hydrohalic acids, e.g. hydrobromic or hydrochloric acid, or the tosylate.
  • the reaction may be effected either in the absence of a solvent or in an inert organic solvent, e.g. a lower alcohol of l to 6 carbon atoms, acetone, or a cyclic or straight chain ether such as dioxane, tetrahydrofuran or diisopropyl ether.
  • the reaction temperature conveniently is from 20 to 100C.
  • Free base forms of the resulting compounds of formula II are liberated from the acid addition salt forms in known manner, e.g. by treatment with an aqueous alkali metal hydroxide solution.
  • the compounds of formulae III and IV, used as starting materials in the above process, are either known or may be produced in known manner from known starting materials, for example a compound of formula IV wherein R R and R are alkyl may be obtained by reacting an alkvlisothiocyanate with a dialkyl amine in conventional manner.
  • the compounds of formula I are useful because they possess pharmacological activity in animals.
  • the compounds are useful as hypoglycaemic agents as indicated by a lowering of the blood sugar content in the blood of rats on p.o. administration of from 100 to 300 mg/kg animal body weight, of the compounds, in accordance with the following test:
  • the compound to be tested is administered in increasing doses to groups of 5 to 10 animals. 2 hours after administration, a blood sample is taken from each animal, and the glucose content in the blood serum is established using the ferric cyanide test. The blood sugar lowering effect is determined by a comparison with a control group of 5 to 10 animals to which is administered a physiological common salt solution.
  • the dosage will, of course, vary depending on the compounds employed, mode of administration and condition to be treated. However, in general, satisfactory results are obtained when administered at a daily dosage of from 1.5 mg to about 300 mg per kg animal body weight, conveniently given in divided doses 2 to 4 times a day or in sustained release form.
  • the total daily dosage is in the range from about 100 to about 1000 mg, and dosage forms suitable for oral administration comprise from about 25 mg to about 500 mg of the compounds admixed with a solid or liquid pharmaceutical carrier or diluent.
  • the compounds of formula I are usually oily at room temperature, the compounds are conveniently administered in pharmaceutically acceptable acid addition salt forms which have the same order of activity as the free base forms, and which are readily prepared in conventional manner.
  • Representative acid addition salt forms include organic acid salt forms such as the hydrogen maleate, fumarate, tartrate and methane sulphonate and mineral acid salt forms H IV;
  • a pharmacetical composition may comprise a compound of formula I, in free base form or in pharmaceutically acceptable acid addition salt form, in association with a pharmaceutical carrier or diluent.
  • Such compositions may be prepared by conventional techniques to be in the form of, for example, capsules, tablets, suppositories, suspensions or solutions, for enteral or parenteral administration.
  • these pharmaceutical compositions may contain suitable preserving, stabilizing, wetting, solubilizing, sweetening, flavouring or colouring agents.
  • An example of a tablet composition comprises 136 mg of N-butyl-N ,N -diallyl-4,4-dimethyl-3-oxopentanamidine hydrobromide, 1 mg of magnesium stearate, 4 mg of polyvinyl pyrrolidone, 0.5 mg of dimethyl silicone oil, 5 mg of talc, 10 mg of maize starch, 137.8 mg of lactose and 1.5 mg of polyethylene glycol 6000.
  • the tablets are produced in conventional manner and are provided with a double slit.
  • R R and R are independently alkyl, R, is alkyl, alkenyl, phenyl, or substituted phenyl and R and R are, independently, alkyl, alkenyl, alkoxyalkyl or cyanoalkyl. More especially R R and R are alkyl, especially methyl, and R R and R are independently alkenyl especially of 3 to 4 carbon atoms or especially alkyl of l to 4 carbon atoms.
  • R is phenyl or substituted phenyl and R is alkyl, or R and R together are -(CH and R is alkyl, or R R and R together with the carbon atom to which they are bound form the adamantyl radical, R is a group of formula;
  • R, and R are the same or different and each is alkyl of l to 4 carbon atoms, or
  • R and R together with the nitrogen atom are a het- EXAMPLE 1 N ,N -triethyl-4,4-dimethyl-3-oxo-pentanamidine a. N,N -triethyl-5,5-dimethyl-4-oxo-2- thiahexanamidine A mixture of 14.3 g of bromopinacoline, 12.8 g of N,N-triethyl thiourea and 120 cc of acetone is heated to the boil at reflux for 8 hours. The reaction mixture is subsequently concentrated by evaporation in a vacuum.
  • N ,N -triethyl- 5,5-dimethyl-4-oxo-2-thiahexanamidine is obtained as hexanamidine hydrobromide i 19.5 g of N ,N -di-isobutyl-N -methyl thiourea are dissolved in. 100 cc of acetone, and 17.3 g of bromopinacoline are added to the solution. The resultoily residue. 5 ing mixture is allowed to stand at 20for 12 hours.
  • N,N -trlethyl-4,4-dimethyl-3-oxo-pentanamidine mixture is subsequently heated to the boil for 4 hours, g 0f the y thyl-5,5-dimethy1-4-0xois subsequently cooled, and the resulting precipitate is 2-thiahexanamidine obtained in section a) are mixed filtered off.
  • the reaction mixture is subc. N ,N -di-isobutyl-N,4,4-trimethyl-3-oxosequently cooled and triturated with 1 N hydrobromic pentanamidine acid until the acid reaction is maintained.
  • the resulting melted material is neutralized with from 2 parts by volume of isopropanol/g of compound, 1 N hydrobromic acid (about 28 cc).
  • the aqueous soor from 4.5 parts by volume of acetone/g of compound, lution is poured off and cold alcohol is added to the the resulting N,N -triethyl-4,4-dimethyl-3-oxosmeary crystalline product until the solid components pentanamidine hydrobromide has a M.P. of 138-140. are filterable. Filtration is subsequently effected.
  • the aqueous soor from 4.5 parts by volume of acetone/g of compound, lution is poured off and cold alcohol is added to the the resulting N,N -triethyl-4,4-dimethyl-3-oxosmeary crystalline product until the solid components pentanamidine hydrobromide has a M.P. of 138-140. are filterable. Filtration is subsequently
  • Treatment of the hydrobromide with an aqueous 2 N filter residue contains about 11.6 g of a mixture of trisodium hydroxide solution, extraction of the alkaline phenyl arsine and triphenyl arsine sulphide.
  • the filtrate solution with diethyl ether and concentration by evapois extracted with 100 cc of diethyl ether, and the aqueration of the ethereal mixture yields oily N ,N -triethyl- 0115 ution is concentrated by evaporation in a vac- 4,4-dimethyl-3-oxo-pentanamidine. uum.
  • N ,N -di-isobutyl-N-methyl thiourea ing Tables are obtained by using the processes exem- A solution of 7.3 g of methyl isothiocyanate in 20 cc plified in the above Examples 1 and 2 and the correof benzene is added to a solution of 12.9 g of disponding starting materials.
  • the indicated melting isobutylamine in cc of benzene, and the resulting points refer to the corresponding salt forms.
  • the free mixture is allowed to stand at 20 for 4 days.
  • the mixbase forms of the compounds of formula 1 are obtained ture is subsequently concentrated by evaporation, and from the salt forms in known manner, e.g.
  • Methyl Methyl Methyl Allyl lsobutyl lsobutyl 148-149 Bromide 36 Methyl Methyl Methyl Allyl All 1 All 1 93-94 Oxalate 37 Methyl Methyl Methyl Butyl Met yl Me't yl 113-1 14 Bromide 38 Methyl Methyl Methyl Butyl Ethyl Ethyl 1l7-l 18 Bromide 39 Methyl Methyl Methyl Butyl Propyl Propyl 79-80" Bromide 40 Methyl Methyl Methyl Butyl lsopropyl lsopropyl 130-1 32 Bromide 41 Methyl Methyl Methyl Butyl Butyl Butyl Butyl Butyl 78-8 2 Bromide 42 Methyl Methyl Methyl Butyl Allyl Allyl Ally
  • R is alkyl of l to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof, cyanoalkyl wherein the alkyl radical is of l to 5 carbon atoms, or a group of formula wherein R-, and R, are the same or different and each is alkyl of l to 4 carbon atoms, and
  • R, and R are the same or different and each is alkyl of 1 to 8 carbon atoms, alkenyl of 2'to 8 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms in the aggregate thereof or cyanoalkyl wherein the alkyl is of 1 to 5 carbon atoms, or one of R,, R, and R, is phenyl or phenyl substituted with alkyl of 1 to 4 carbon atoms or halo and the others of R,, R, and R, are as defined above, provided at least one of R,, R, and R, is cyanolkyl wherein the alkyl is of i to 5 carbons.
  • R or one of R,, R, and R, is, when substituted phenyl, alkylphenyl, the alkyl radical thereof having 1 to 4 carbon atoms, or halophenyl.
  • R is alkyl of 1 to 4 carbon atoms, phenyl or phenyl substituted with alkyl of l to 4 carbon atoms or chloro, and
  • R is alkyl of 1 to 4 carbon atoms, or
  • R, and R together are (CH,),,, wherein n is an integer from 2 to 7, and
  • R is alkyl of 1 to 4 carbon atoms, or
  • R is alkyl of l to 8 carbon atoms, alkenyl of 3 to 4 carbon atoms, methoxyethyl or cyanoethyl or a group of formula wherein R, and R, are the same or different and each is alkyl of l to 4 carbon atoms, and
  • R, and R are the same or different and each is alkyl of i to 8 carbon atoms, alkenyl of 3 to 4 carbonatoms, methoxyethyl or cyanoethyl, or one of R,, R, and R, is phenyl or phenyl substituted with alkyl of 1 to 4 carbon atoms or chloro and the others of- R,, R, and R, are as defined above,
  • R, R, and R is cyanoethyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US366681A 1972-06-07 1973-06-04 Cyanoalkyl substituted-3-oxo-alkamidines Expired - Lifetime US3875205A (en)

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US426714A US3884974A (en) 1972-06-07 1973-12-13 2-Ketoamidines

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CH844372 1972-06-07
CH291773 1973-02-28

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JP (1) JPS4975528A (is")
AU (1) AU5668973A (is")
DD (1) DD107443A5 (is")
DE (1) DE2328341A1 (is")
FR (1) FR2187339A1 (is")
IL (1) IL42434A0 (is")
NL (1) NL7307651A (is")

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2850521A (en) * 1956-11-29 1958-09-02 Du Pont Nu-(2, 2-dicyanovinyl) imido compounds and their preparation
US3055883A (en) * 1960-03-10 1962-09-25 Ciba Geigy Corp Benzo-alkylenimino-lower guanidines
US3093632A (en) * 1961-02-02 1963-06-11 Ciba Geigy Corp Dibenzpolymethylenimino-alkylene-guanidines
US3119735A (en) * 1961-08-18 1964-01-28 Geigy Ag J R Method for combatting plant-parasitic nematodes
US3202710A (en) * 1962-12-06 1965-08-24 Rexall Drug Chemical 1-(2-cycloalkyl-2-dilower alkylamino-ethyl) guanidines
US3203988A (en) * 1962-11-23 1965-08-31 Parke Davis & Co Cycloalkyloxyalkyl guanidine compounds
US3234266A (en) * 1963-08-13 1966-02-08 Du Pont N-hydrocarbyloxyiminomalononitriles and process for preparing them
US3270054A (en) * 1964-07-31 1966-08-30 Geigy Chem Corp Adamant-1-yl-and homoadamant-1-yl-oxy-, -thio-and amino guanidine derivatives
US3283003A (en) * 1960-12-23 1966-11-01 Smith Kline French Lab 2-(n-lower alkyl-n-cycloheptyl- and cyclooctylamino) ethyl guanidines

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2850521A (en) * 1956-11-29 1958-09-02 Du Pont Nu-(2, 2-dicyanovinyl) imido compounds and their preparation
US3055883A (en) * 1960-03-10 1962-09-25 Ciba Geigy Corp Benzo-alkylenimino-lower guanidines
US3283003A (en) * 1960-12-23 1966-11-01 Smith Kline French Lab 2-(n-lower alkyl-n-cycloheptyl- and cyclooctylamino) ethyl guanidines
US3093632A (en) * 1961-02-02 1963-06-11 Ciba Geigy Corp Dibenzpolymethylenimino-alkylene-guanidines
US3119735A (en) * 1961-08-18 1964-01-28 Geigy Ag J R Method for combatting plant-parasitic nematodes
US3203988A (en) * 1962-11-23 1965-08-31 Parke Davis & Co Cycloalkyloxyalkyl guanidine compounds
US3202710A (en) * 1962-12-06 1965-08-24 Rexall Drug Chemical 1-(2-cycloalkyl-2-dilower alkylamino-ethyl) guanidines
US3234266A (en) * 1963-08-13 1966-02-08 Du Pont N-hydrocarbyloxyiminomalononitriles and process for preparing them
US3270054A (en) * 1964-07-31 1966-08-30 Geigy Chem Corp Adamant-1-yl-and homoadamant-1-yl-oxy-, -thio-and amino guanidine derivatives

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NL7307651A (is") 1973-12-11
DD107443A5 (is") 1974-08-05
FR2187339A1 (is") 1974-01-18
JPS4975528A (is") 1974-07-20
DE2328341A1 (de) 1974-01-03
IL42434A0 (en) 1973-08-29
AU5668973A (en) 1974-12-12

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