CA1214776A - Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilides - Google Patents

Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilides

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Publication number
CA1214776A
CA1214776A CA000435457A CA435457A CA1214776A CA 1214776 A CA1214776 A CA 1214776A CA 000435457 A CA000435457 A CA 000435457A CA 435457 A CA435457 A CA 435457A CA 1214776 A CA1214776 A CA 1214776A
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Prior art keywords
acetanilide
methyl
chloro
produced
process according
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French (fr)
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Edith Rudinger
Xavier Perlia
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Pharmaton SA
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Pharmaton SA
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    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • 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
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

The present invention provides basic acetanilides of the formula III

III

Description

77~

The present inverltion rela-tes to nove~ hasic ace-tani.li.des, to a process for their preparation and to a phar-maceutica1 composition con-taining these novel acetanilides.

The present invention provides novel compounds which e.g. may be used as local anaesthesia and antiarrhythmic active agents, and which show a lower toxicity and an improved effectiveness over the compounds known in the ar-t.

The presen-t invention also provides processes for preparing the novel compounds, which are easy to carry out and which are economical.

According to the present invention there are pro-vided basic acetanilides having the formula III

/ Rl /j ~ I]:I
/ ----Nll-C~-C112-~5 o R~

"~

~214776 WhC`I-eill 1~1 is l~ydrogerl or a lower allcyl ~1roup, a1~d 1~4 is 1~alo9e1l, a lower alkoxy, a nitro, amino, propiony1 or trl-halomethyl, particularly a trifluoromethyl group and R5 is a basic group selected from di lower alkyl amino, lower cyclo alkyl amino, or a 6-membered heterocyclic group having at least one nitrogen atom in the ring and their pharmacologi-cally useful salts.

The process of the present invention Eor preparing thc 1~ovel basic acetanilides of the formula III

~_ - ~214776 Nl-l -C -C~ R5 :[ I I

~

wherein R~ 4 and R5 are defined above, and their pharma-cologically useful salts, is characterized in that an lQ aniline of the formula I

_~ 1 /~ \ ~ I
N1~2 1~ ~'~< ' ,.

wherein Rl and R4 are defined above, is reacted under cool-ing or at room temperature in a solvent and in the presence of a base with a halogen compound of formula II
X-CO-CH2-Hal II

wherein X is a hydroxyl group, an ester group, a halide, an amide group or an anhydride group, and Hal is a halogen atom to yield a compound of formula IV

~ l-l-co-c~l2-llal IV

wherein Rl, R4 and Hal are defined above, and that then these compounds are reacted in an inert solvent at elevated temperature with an amine delivering the group R5, and that the obtained compounds may be transformed into their phar-g - 3 -77~

macoloqically ~Iseful salts.

The interrnediates of formula IV are prepared in such a way that halogen fatty acids or other suitable derivatives, such as esters, halides (e.g. acid chloride or bromide), amides or anhydrides, are contacted with an aniline under cooling or at room temperature in a solvent, e.~. acetone, acetic acid, acetic acid ethylester, chloro-form, in the presence of a base, such as sodiu~ carbonate, lo potassium carbonate, sodium bicarbonate or potassium bi-carbonate, sodium acetate, or in an aqueous sodium acetate buffer. The halogen acetanilides of the general formula IV
are reacted with an amine in an inert solvent, preferably benzene, at an elevated temperature.
The acetanilides of the general formula III may also be prepared without isolation of the intermediate of the formula IV, in that after the halogen alkanoylization the corresponding amine is added to the reaction mixture in a higher boiling inert solvent, e.g. toluene or xylene, followed by heating this mixture.

The compounds of the general formula III, wherein R4 is amino, may be prepared from the corresponding ace-tanilides of the formula III, wherein R4 is nitro, by reduc-tion.

The acetanilides of formula III, wherein R4 is halogen, may be prepared either from the corresponding anilines, as described above, or from the acetanilides, wherein R4 is amino, with the Sandmeyer reaction.

The process of this invention may also be effected in the presence of catalysts. A person skilled in the art may easily determine the suitable reaction tempe~ratules and reaction times~ Usually one works at standard pressur., whereby also excess pressure and under pressure (vacuum) are not excluded.

The administration of the novel compounds of formula III according to this invention is realized in a conventional way, as this is known in the prior art for the known compounds.

The preferred embodiments are illustrated in the set of Examples, wherein also some nove~ starting materials and intermediates are described and where the temperatures are in C

A. With isolation of the intermediate of the ~ormula ~V

Example 1 To a mixture of 53 g (0.35 mol) 2-ethoxy-6-methyl-aniline in 525 ml absolute acetone and 70 g sodium bicarbonate are added drop by drop under cooling with ice during one hour 46 g (0.4 mol) chloroacetyl chloride, and then this mixture is stirred for one hour at room tempera-ture. The inorganic salt is filtered with suction and washed with acetone. The filtrate is evaporated in the vacuum of a water jet pump, to the residue water is added, and the precipitated crystals of 2-chloro-2'-ethoxy-6'-methyl-acetanilides, mp. 148-149, are filtered with suction.
Example 2 As described in Example 1, 2-chloro-2'-methyl-6'-nitro-acetanilide is obtained, mp 140-141.5 when 2-methyl-6-nitro-aniline is used instead of 2-ethoxy-6-methyl-ani-line.

Alnillat.io .Ex am~ :1. e _ _ To 10.25 ~ (0.0~5 mol) 2-chloro-2'-ethoxy-6'-methyl-acetarlilide in 10 ml benzene are added to 10 g (0.136 mol) diethylamine and this mixture is refluxed for 6 hours.
After cooling the precipitated die-thylamine hydrochloride is filtered with suction, washed with benzene! and the filtrate is evaporated in the vacuum of the water jet pump. To the residue is added water and ether, the base is extracted from the ether layer with 5% hydrochloric acid, the aqueous aci-dic solution is rendered alkaline,and extracted with ether.
After drying and evaporation the ether the resiude is dis-solved in ethanol, and under cooling, ethereal hydrochloricacid is added drop by drop, and the hydrochloride of 2-diethyl amino-2'-ethoxy-6'-methyl-acetanilide, mp. 107-109 , is obtained.

Example 2 As described in Example 1, 2-piperidino-2~-ethoxy-6'-methyl-acetanilide, mp. 79-80, is obtained, and the base is reacted to the hydrochloride, mp. 192-193, when piperi-dine is used instead of diethylamine.

Example 3 When pyrrolidine is used instead of diethylamine, as described in Example 1, 2-pvrro]idino-2'-ethoxy-6'-methyl-acetanilide, mp. 60.5-62 is obtained, which is reacted to the hydrochloride, mp~. 180~181.5.

xample As described in Example 1, 2-diethyla~ o-2'-.~ \ 6 ~

methyl-6'-llitro-acetanilide, mp. 60~-61, is obtained from
2-chloro-2'-methyl-6'-nitro-acetanilide and diethylamine, as well as its hydrochloride, mp. 166-168 .

Example 5 When piperidine is used instead of diethylamine~
as described in Example 4, 2-piperidino-2'-methyl-6'-nitro-acetanilide, mp. 72-73, and its hydrochloride, mp. 192-194, is obtained.

Example 6 As described in Example 1, the hydrochloride of 2-diethylamino-2'-trifluoromethyl-acetanilide, mp. 160.1, is prepared, when 2-chloro-2'-trifluoromethyl-acetanilide and diethylamine is used.

Example 7 When pyrrolidine is used instead of diethylamine, as described in Example 6, the hydrochloride of 2-pyrroli-dino-2'-trifluoromethyl-acetanilide, mp. 229.4, is obtai-ned.

Example 8 As described in Example 1, the hydrochloride of 2-pyrrolidino-2'-propionyl-acetanilide is prepared, when 2-chloro-2'-propionyl-acetanilide and pyrrolidine are used.

Example 9 As described in Example 1, the hydrocllloride of 2-35 pyrrolidino-2'-methyl-6'-propionyl-acetanilide, mp. 192.6, is prepared when 2-chloro-2'-methyl-6'-propionyl-acetallilide ~r f~ - 7 -1~:14776 and pyrrolidine are used.

Tlle 2-methyl-6-propionyl-aniline, which is used as startin~ material, is prepared as follows from 2-amino-3-methyl-benzonitrile:

From 6.3 g (0.26 mol) magnesium and 25.5 g ethyl-bromide in 130 ml absolute ether the ethyl magnesium-bromide is prepared which is heated for 30 minutes on the water bath. A solution of 6.65 (0.05 mol) 2-amino-3-methyl-benzonitrile in 100 ml absolute ether is then added slowly drop by drop, and the mixture is refluxed under stirring for 15 hours. After cooling the mixture is poured on 110 g ice and the solution of 15.6 g ammonium-chloride in 67 ml water is added. The ether layer is separated, and the aqueous layer is extracted wi-th ether. From the combined ether layer the ether is distilled off, and the residue is re-fluxed with 9.5 ml water and 11.2 m] concentrated hydro-chloric acid for 30 minutes. After cooling the mixture is extracted with ether, the aqueous layer is rendered alkaline and extra~cted with ether. After drying and evaporating the ether the 2-methyl-6-propionyl-aniline is obtained, which was characterized as hydrochloride, mp. 191.2.

Example 10 .

To 10.9 g (0~.05 mol) 2-chloro-2'-chloro-6'-methyl-ace-tanilide in 30 ml absolute toluene are added 12.75 g (0.15~mol) cyclopentylamine in 50 ml toluene, and this mixture is refluxed for 6 hours. After cooling the pre-cipitated cyclopentylamine-hydrochloride is filtered with suction, the filtrate is evaporated and to the residue is added water and ether. The ether is e~tracted with 5~
hydrochloric acid solution, wherefrom the hydrochloride of 2-cyclopentylamine-2'-chloro-6'-methyl-acetanilide crys-tallizes, mp. 20~.7.

\

` ~214776 From 1 g of the hydrochloride the base was pre-pared, mp. 76.8 .

Example 11 When cyclopropylamine in benzene is added to 2-chloro-2'-chloro-6'-methyl-acetanilide and when this mixture is heated in an autoclave having a glass insertion for 10 hours at a temperature of 100, and when after cooling the prescription of Example 1 is followed, then the hydrochlo-ride of 2-cyclopropylamine-2'-chloro-6'-methyl-acetanilide, mp. 257, is obtainéd.

B. Without isolation of the intermediate of formula IV

Example 1 To 18.6 g (0.1 mol) 2-bromo-6-methyl-aniline in 150 ml absolute acetone and 20 g sodium bicarbonate are added drop by drop under cooling with ice during one hour 12 g (0.11 mol) chloroacetyl chloride and then this mixture is stirred at room temperature for 30 minutes. To the mixture are added 22 g (0.3 mol) diethylamine in 50 ml toluene, and this mixture is refluxed for 6 hours. The further treatment is the same as described in section A in Example 1.

The hydrochloride of the 2-diethylamino-2'-bromo-6'-methyl-acetanilide, mp. 172-174, is obtained.
a) The same 2-diethylamino-2'-bromo-6'-methyl-acetanilide can be prepared according to the Sandmeyer reaction from 2-diethylamino-2'-amino-6'-methyl-acetanilide as follows:
11.75 g (0.05 mol) 2-diethylamino-2'-amino-6`-~' ~214776 methyl-acetanilide in 30 ml 48go hydrobromic acid are cooled in an ice bath, and at a temperature of -5 this mixture is diazotized with 3.45 g sodium nitrite in 20 ml water during 30 minu~es (iodo-starch paper test) and then this mixture is stirred for 40 minutes at a temperature of -5. This sus-pension is added slowly to a mixture having a temperature of 70 of 4 g CuBr in 20 ml 48% hydrobromic acid, and this mixture is stirred for 2 hours at this temperature. After cooling this mixture is extracted with ether, the acidic solution is rendered alkaline and ex-tracted with ether.
After drying and evaporating the ether the residue is dis-solved in ethanol and transformed into the hydrochloride with ethereal hydrochloric acid, which is identical with the product, mp. 172-174, described in Example 1.
Reduction of the 2-diethylamino- and 2-piperidino-2'-methyl-6'nitro-acetanilide.

Example 1 a) To 25 g (0.094 mol) 2-diethylamino-2'-methyl-6'-nitro-acetanilide in 500 ml concentrated hydrochloric acid are added under stirring during one hour 100 g tin (II)-chl~oride. The mixture is heated for 30 minutes on a boiling water bath, after cooling with ice this mixture is rendered alkaline with 35% sodium hydroxide solution, followed by an extraction with ether. After washing, drying and evaporating the ether the 2-diethylamino-2'-amino-6'-methyl-acetanilide, mp. 105-106.5, is obtained, which is transformed into its dihydrochloride, mp. 182-184, with ethereal hydr,ochloric acid.

b) The same 2-diethylamino-2'-amino-6'-methyl-acetanilide is also obtained as follows:

To a mixture of 300 ml Pd/C in 60 ml water under ~-- 10 --1~14776 nitrogen are added 4.8 c; sodium borohydride in 90 ml water.
Thell the solutioll of 15.9 g~(0.06 mol) 2-diethylamirlo-2'-methyl-6'-llitro-acetallilide in 150 ml Methanol is added drop by drop during 30 minutes, and this mixture is filtra-ted, the filtrate is evaporated in -the vacuum of a water jet pump, water is added and the precipitated crystals are filtered with suction. Mp. 105-106.5 .

Example 2 1~
As described in Example l b), 2-piperidino-2'-amino-6'-methylacetanilide, mp. 169-170, is prepared with -the difference, that the mixture is heated before the filtration, because -the product is lit-tle soluble in cold methanol. The base is dissolved in ethanol and transfor-med with an etheric hydrochloric acid into -the dihydro-chloride. MP. 25g-260C.

~ -- 11 --

Claims (30)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN
EXCLUSIVE PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS
FOLLOWS:
1. A process for preparing a basic acetanilide of the formula III

III
wherein R1 is hydrogen or lower alkyl, and R4 is halogen, lower alkoxy, nitro, amino or propionyl or trihalomethyl, and R5 is a basic group selected from di lower alkyl amino, lower cyclo alkyl amino; or a 6-membered heterocyclic group having at least one nitrogen atom in the ring which comprises reacting a compound of formula IV.

IV

wherein R1 and R4 are defined above and Hal is a halogen atom in an inert solvent at elevated temperature with an amine delivering the group R5 as defined above, and, when required, converting the obtained compound into a pharma-cologically useful salt.
2. A process according to claim 1, in which the compound of formula IV is prepared by reacting an aniline of the formula I

I

wherein R1 and R4 are defined above under cooling or at room temperature in a solvent and in the presence of a base with a halogen compound of formula II

X-CO-CH2-Hal (II) wherein X is a hydroxyl group, an ester group, a halide, an amide group or an anhydride group and Hal is a halogen atom.
3. A process of claim 2, in which the compound of formula II is an acid chloride or acid bromide.
4. A basic acetanilide of formula III

III
wherein R1 is hydrogen or lower alkyl, and R4 is halogen, lower alkoxy, nitro, amino, propionyl or trihalomethyl, and R5 in a basic group selected from di lower alkyl amino, lower cyclo alkyl amino; or a 6-membered heterocyclic group having at least one nitrogen atom in the ring or a pharmacologically useful salt thereof whenever prepared or produced by the pro-cess claimed in claim 1, 2 or 3.
5. A process according to claim 1, in which R1 is hydrogen or methyl, R4 is chlorine, bromine, trihalomethyl, ethoxy, nitro, amino or propionyl and R5 is diethylamino, piperidino, pyrrolidino, cyclopropylamino or cyclopentylamino.
6. A process according to claim 5, in which the free acid is converted into a salt selected from the hydro-chlorides, hydrobromides, fumarates, maleates, hydrogen fumarates and hydrogen maleates.
7. A basic acetanilides of formula III given in claim 1 or a pharmacologically useful salt thereof where R1, R4 and R5 are as in claim 5 whenever prepared or produced by the process claimed in claim 5 or an obvious chemical equivalent thereof.
8. A salt of a basic acetanilide of formula III
given in claim 1, where R1, R4 and R5 are as in claim 5 when-ever prepared or produced by the process claimed in claim 6 or an obvious chemical equivalent thereof.
9. A process according to claim 1 which comprises refluxing 2-chloro-2'-ethoxy-6'-methyl-acetanilide in ben-zene and with diethylamine.
10. 2-diethylamino-2'-ethoxy-6'-methyl-acetanilide whenever prepared or produced by the process claimed in claim 9 or an obvious chemical equivalent thereof.
11. A process according to claim 1 which comprises refluxing 2-chloro-2'-ethoxy-6'lmethyl-acetanilide in ben-zene and with piperidine.
12. 2-piperidino-2'-ethoxy-6'-methyl-acetanilide whenever prepared or produced by the process claimed in claim 11 or an obvious chemical equivalent thereof.
13. A process according to claim 1 which comprises refluxing 2-chloro-2'-ethoxy-6'-methyl-acetanilide in ben-zene and with pyrrolidine.
14. 2-pyrrolidono-2'-ethoxy-6'-methylacetanilide whenever prepared or produced by the process claimed in claim 13 or an obvious chemical equivalent thereof.
15. A process according to claim 1 which comprises refluxing 2-chloro-2'-methyl-6'-nitro-acetanilide in benzene and with diethylamine.
16. 2-diethylamino-2'-methyl-6'-nitro-acetanilide whenever prepared or produced by the process claimed in claim 15 or an obvious chemical equivalent thereof.
17. A process according to claim 1 which comprises refluxing 2-chloro-2'-methyl-6'-nitro-acetanilide in benzene and with piperidine.
18. 2-piperidino-2'-methyl-6'-nitro-acetanilide whenever prepared or produced by the process claimed in claim 17 or an obvious chemical equivalent thereof.
19. A process according to claim 1 which comprises refluxing 2-chloro-2'-trifluoromethyl-acetanilide in benzene and with diethylamine.
20. 2-diethylamino-2'-trifluoromethyl-acetanilide whenever prepared or produced by the process claimed in claim 19 or an obvious chemical equivalent thereof.
21. A process according to claim 1 which comprises refluxing 2-chloro-2'-trifluoromethyl-acetanilide in benzene and with pyrrolidine.
22. 2-pyrrolidine-2'-trifluoromethyl-acetanilide whenever prepared or produced by the process claimed in claim 21 or an obvious chemical equivalent thereof.
23. A process according to claim 1 which comprises refluxing 2-chloro-2'-propionyl-acetanilide in benzene and with pyrrolidine.
24. 2-pyrrolidino-2'-propionyl-acetanilide whenever prepared or produced by the process claimed in claim 23 or an obvious chemical equivalent thereof.
25. A process according to claim 1 which comprises refluxing 2-chloro-2'-methyl-6'-propionyl-acetanilide in ben-zene and with pyrrolidine.
26. 2-pyrrolidino-2'-methyl-6'-propionyl-acetanilide whenever prepared or produced by the process claimed in claim 25 or an obvious chemical equivalent thereof.
27. A process according to claim 1 which comprises refluxing 2-chloro-2'-chloro-6'-methyl-acetanilide in absolute toluene with cyclopentylamine.
28. 2-cyclopentylamino-2'-chloro-6'-methyl-acetanilide whenever prepared or produced by the process claimed in claim 27 or an obvious chemical equivalent thereof.
29. A process according to claim 1 which comprises heating a mixture of 2-chloro-2'-chloro-6'-methyl-acetanilide and cyclopropylamine in a autoclave at 100°C.
30. 2-cyclopropylamino-2'-chloro-6'-methyl-acetanilide whenever prepared or produced by the process claimed in claim 29 or an obvious chemical equivalent thereof.
CA000435457A 1982-08-27 1983-08-26 Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilides Expired CA1214776A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH5116/82A CH650768A5 (en) 1982-08-27 1982-08-27 BASIC ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE ACETANILIDES.
CH5116/82-8 1982-08-27

Publications (1)

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CA1214776A true CA1214776A (en) 1986-12-02

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CH (1) CH650768A5 (en)
DE (1) DE3328186A1 (en)
FR (1) FR2532306B1 (en)
GB (1) GB2129424B (en)
IT (1) IT1168212B (en)
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CS195321B2 (en) * 1975-12-23 1980-01-31 Ciba Geigy Ag Plant growth suppressing agents
GB1514151A (en) * 1977-01-24 1978-06-14 Gallardo Antonio Sa Piperidine derivatives

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FR2532306A1 (en) 1984-03-02
GB2129424B (en) 1986-07-09
DE3328186A1 (en) 1984-03-01
JPS59130250A (en) 1984-07-26
SE8304456D0 (en) 1983-08-17
IT8348886A0 (en) 1983-08-26
FR2532306B1 (en) 1989-03-10
CH650768A5 (en) 1985-08-15
GB8321953D0 (en) 1983-09-14
GB2129424A (en) 1984-05-16
SE8304456L (en) 1984-02-28
IT1168212B (en) 1987-05-20

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