IL30223A - Lipid-normalizing 4'-phenoxy alkanesulfonanilides - Google Patents

Lipid-normalizing 4'-phenoxy alkanesulfonanilides

Info

Publication number
IL30223A
IL30223A IL30223A IL3022368A IL30223A IL 30223 A IL30223 A IL 30223A IL 30223 A IL30223 A IL 30223A IL 3022368 A IL3022368 A IL 3022368A IL 30223 A IL30223 A IL 30223A
Authority
IL
Israel
Prior art keywords
inclusive
carbon atoms
value
ide
zero
Prior art date
Application number
IL30223A
Other languages
Hebrew (he)
Other versions
IL30223A0 (en
Original Assignee
Upjohn Co
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
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of IL30223A0 publication Critical patent/IL30223A0/en
Publication of IL30223A publication Critical patent/IL30223A/en

Links

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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl

Landscapes

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

Description

LIP ID-HOB MA LIZ IN G « -PHBNOXYA LKANESUL O ILIDES Abstract of the Disclosure Disclosed are 1 ipid-normal izing 1 -phenoxyal kanesulfon-anil ides which are derived f rom £-phenoxyani 1 i nes .
Background of the Invention It is known that relatively high serum chplesterol and triglyceride levels are injurious to arterial tissue, and that such injuries may be one of the causes of coronary heart disease and atherosclerosis. It has now been found that the serum 1 ip id level in a mammal , and in particular the cholesterol and the triglyceride levels, can be lowered by administering to the mammal an effective amount of a compound of the present i nvent ion.
Summary of the Invention The compounds of this invention are '-phenoxyal kanesul-fon-anilides which can be represented by the formula wherein X can be h carbon atoms inclusive, or alkoxy containing from 1 to carbon atoms, inclusive; Y can be halo; R1 can be hydrogen, alkyl contain ing. f rom 1 to 4 carbon atoms, inclusive, J-piperidinopropyl, 2-piperi-dinoethyl , .5-(l-pyrr.o1 idinyl )propyl, 2- (1-pyrrol idinyl )ethyl J-morphol inopropyl , 2-morphol inoethyl and dial kylaminoalkyl of the formu la where R and R can be alike or. different and are al k l contain containing from 1 to 6 carbon atoms inclusive. The subscript are f zero to re useful a is inclusive, la where R2 has the same meaning as above, and "Halogen" preferably is chlorine or b romi ne.
In Formulas I and I I illustrative halo radicals are fluoro, chloro, bromo, and ipdo.
Illustrative of the alkyl radicals contemplated herein are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.^butyl, tert. -butyl, the pentyls, and the hexyls. 111 ust rat i e al koxy radicals are methoxy, ethoxy, propoxy, isoprppoxy, butoxy, isobutoxy, sec.-butoxy, and tert . T-butoxy.
The phenoxyan i 1 i nes represented by Formula I I are a known group of compounds, some of which are commercial ly available. ; Ί Illustrati e phenoxyan! lines (I I) are £- (£-chlorophenoxy )-an! 1 ! ne, £- (o-ch lorophenoxy )an i 1 ine, 5" chloro- - phenoxyan i .1 i ne, ani 1 ine, p.- (2,5-dichlot^/fienoxy)anI 1 Ine, £- (2,4-dibromophenoxy)-ani 1 ine, 3,5-di iodo-4-phenoxyan i ine, £- (£-b romophenoxy ) an i 1 ine, £- (£-iodop henoxy) ani l ine, £- (o- iodophenoxy)ani 1 i ne, 3-iodo-4-phenoxyani 1 ine, £- (m- b romophenoxy ),a n i l ine, £- (2,4,5- tri chloro-phenoxy)ani 1 ine, £- (2,4,6- trIch1orophenoxy)ani 1 ine, £-(£-tert.-butyl phenoxy) an ί 1 ine, N-methyl-£- phenoxyani 1 i ne, £- (£- tol yl oxy )-an i 1 Ine, £- (3, -xyl yl oxy) ani 1 ine, £-.(£- me thoxyphenoxy) an i 1 i ne, £- (m- met hoxy phenoxy) ani 1 ine, £- (3, 5~ dime thoxyphenoxy) an 11 ine, £- (6-bromo-2, -xyl yloxy )ani 1 ine, 3,5-di iodo- - (£-methoxyphenoxy )-ani 1 ine, .£- (2,.6-dimethoxyphenoxy)-N- Isopropylani 1 ine, N-sec-butyl-£- (£-methoxyphenoxy)an 11 ine, £-phenoxyani 1 ine, and the like.
The alkanesul fonyl halides of Formula I I I are also a known class of compounds, . and some are commercially available.
Methods of preparation can be found in J. Am. Chem. Soc. 58. 13 8 (1936); J. Am. Chem.. Soc, 1837 2439 (1937); and J.
Am. Chem. Soc. 60, i486 (1938).
Illustrative al kanesul fonyl hal ides (I I I ) are methane-sul fonyl chloride, ethanesul fonyl chloride, butanesu 1 fonyl chlo'ride.j propanesul fonyl chloride, i-methylethanesul onyl chloride, sec. -butanesul fonyl chloride, i sobutanesu 1 fonyl chloride, pentanesul fonyl chloride, hexanesu 1 fonyl chloride, etc.
The reaction betwpen a phenoxyani 1 ine ( I I) and an alkane-sulfonyl hal ide (I I I) can be carried out by admix! ng one or more equivalents of the al kanesul fonyl hal ide with the phenoxyani line in a suitable reaction medium which is also an acid acceptor for the hydrogen hal ide formed during the reaction, such as pyridine, the al kyl-substi tuted pyridines, N,N-dImethyl -anil ine, the tertiary alkylamines such as tr iethylami ne, trl-methylamine, etc.,; with or w i thout ' inert cosolvents typified , 2312 0° C. to: about 6o° C. Room temperature is preferred, however.
.The reaction product from the foregoing reaction is the des i red . ' ~ phenoxya 1 kanesu 1 onan M ide (l) in which R1 is hydrogen or alkyl. The reaction product can be isolated from . the reaction mixture i n. conventional manner, e.g., by filtration or extract i on ; i nto a water- immi scible solvent, fol lowed by washing and drying of the recovered product. If necessary, the product can be puri fied further by crystal lization or b high vacuum distillation. .· A ' - phenoxya 1 kanesu 1 fonan il i de (I) where R1 is hydrogen can be alkylated by treatment, in an inert organic solvent such as benzene^ tetrahydrof uran, or ,d ioxane, wi th an alkylating agent which can be an alkyl halide or a sec.rami noal ky 1 hal i de. . The a lkyl at ion takes place in the presence of a base, for example, an alkali metal alkoxide such as potassium tert.-butoxide, or an alkali metal hydride such as sodium hydride or potassium hydride. Reaction temperature for the al kylation reaction can range from about 0° C. to about 100° C. When the alkylating agent is a primary alkyl iodide, room temperature is the preferred reaction temperature; however, for alkyl chlorides o o a temperature from about 50 , C. to.about 100 C. is preferred When. sec. -ami hoa l kyl . ha 1 ides in. the form of a hydrohal i de sal t are. employed as the alkylating agent, sufficient base is added to the reaction mixture to 1 iberate the free sec. -ami noa lkyl halide and to form the su!fonani 1 i de al kal i metal salt. 11 lustrative alkyl halides which can be used as alkylating agents are methyl iodide, ethyl iodide, propyl iodide, butyl iodide, methyl bromide, ethyl chloride, propyl bromide, . butyl chloride, secrbutyl bromide, and the like. .111 us t rati ve sec. -ami noal kyl hal ides sui table as al kylati ng agents are N,N-diethyl-2-chloroethy lamiirie, , N,,N-dibutyl-2-chloro 312 ethyl amine, N,N-diethyl-3-chloropropy1amine hydrochloride, N-methyl-N-propyl-3-bromopropylamine hydrochloride, N-ethyl-N-butyl-2-bromoethylamine, N- (2- chloroethy 1 )p i per ί d i ne, N- (3-chloropropyl )pi peri dine, . N- (2-chloroethyl ) pyrrol i dine, N- (3-chloropropyl ) pyrrol idine, N- (2-chloroethyl )morphol ine, N- (3- ch loropropy 1 )morphol i ne, and the like.
The compounds of the present invention where 1 is sec. -aminoalkyl are amines which can exist either -in the noh-protonated or free-base form, or in the protonated or acid addition salt form, depending on the pH of the environment.
Stable, pharmaceutically acceptable protonates can be formed on neutral izat ion. of the free-base . form wi th sui table acids such as hydrogen c l or ide,, hydrogen bromide, sulfuric acid, phosphoric acid, .ace tic . acid, ' and the- like..
The compounds of this invention have 1 i pid-normal i zi ng activity and thus are useful as hypocholesterolemic agents and as hypotriglyceridemic agents , in mammals.
For purposes of administration, the compounds of thi s invention can be combined with, solid or liquid pharmaceutical carriers and formulated in the form of tablets, powder packets, or capsules, using starch or similar excipients. The instant compounds can also be dissolved or suspended in suitable solvents or vehicles for oral or parenteral administration. If desired, the present active ingredients can also be admixed with food .
. The amount of the active ingredient that is to be administered depends on the age, weight, and condition of the recipient, and also on factors such as the frequency and route of administration.
, The dai ly dose range can be from about 0.1 mill igram per kilogram of body weight to about 50 mill igrams per ki logram of 2312 The present invention is further i 11 ustrated by the fol 1 owing examples.
EXAMPLE I : Preparation of 4'-phenoxymethanesul fonani 1 ide £-Phenoxyani 1 ine (about 37 grams) was dissolved in pyridine (about 100 mill il iters). The resulting solution was chil led to about 5° C. and methanesulfonyl chloride (about 15 mill il iters) was added thereto.
The resulting admixture was st i rred at about room temperature for about 4 hours, then diluted with water and ice. A * p red pi tate' was observed to form and was recovered by filtration.
Upon recry-stal 1 ization from methanol , about 35 grams of a pro- o -O duct melting at "125 C. to 126 C, and about 9 grams of the same product melting at 124° C. to 126° C. was obtained. , An _ o o analytical sample melting at 126.5 C. to 127.5 C. was obtained after two additional recrysta 11 i zat ions, using charcoal once. < The product was identified as 4'-phenoxymethanesulfonani 1 ide, obtained in about 83 percent yield.
Analysis for C13H13NO3S: Calc'd. : C, 59-30; H,.4.98; S, 12.18.
Found: . C 59.22; H, 4.76; S, 12.09.
In a manner similar, to Example I, but using ethanesul fonyl chloride as one of the reactants., the corresponding 4'-phenoxy-ethanesul fonani 1 ide can be prepared; using propanesul fony 1 chloride the corresponding 4'-phenoxy- propanesul fonani 1 ide can be prepared; using butanesul fonyl bromide the corresponding ^'-phenoxy-butanesul fonani 1 i de can be prepared; using pentanesu 1 fonyl chloride the corresponding ' - phenoxypentanesu 1 fonani 1 i de can be prepared; using hexanesul fonyl chloride the corresponding 4'-phenoxy- hexanesul fonani 1 ide can' be prepared; etc.
Similarly, react i ng £- (£-chlorophenoxy)ani 1 ine wi th methane- sulfonyl chloride the correspond! ng 4'- (4-chlorophenoxy)methane-sul fonani 1 ide is produced; react i ng 3-chl oro-4-phenoxyan i line with ethanesul fonyl chloride the corresponding ' 3,~chlorb-4l -phenoxyethanesulfon-anilide is produced; react i ng 4- (£-chlorophenoxy)-3,5-di iodoan i 1 i ne wi th propane siil'fonyl chloride the corresponding 4·- (4;-chlorpphenoxy)-5l >5'- * di iodoprppanesu 1 fonani 1 ide is produced; react i ng £- (2,4,5- tri chlorophenoxy)an i 1 i ne wi th butane-sulfonyl chloride the corresponding 4'- (2,4,5- tr ichlorophenoxy)-butanesul fonani 1 i de is produced; reacting £-(£-tert. -buty1phenoxy)ani line with methane-sulfonyl chloride the corresponding 4'- (4- tert.-butylphenoxy)-methanesu 1 fonan i 1 i de is produced; reacti ng N-methyl -£-phenoxyani li he wi th methanesu 1 fonyl chloride the corresponding N-methyl -4'-phenoxymethanesul fonani 1 ide is produced; reacting N-buty 1 -4- (2,4, 6- tr imethyl phenoxy)an i 1 i ne w i th ethanesul fonyl chloride the corresponding N-butyl-41 - (2,4, 6-tr imethyl phenoxy)ethanesu 1 fonan i 1 i de is produced; reacting N-ethyl-4- (2,4,6-trimethylphenoxy)-3,5-di iodo-ani line with propanesul fonyl chloride the corresponding N- ethyl -4" - (2,4, 6- tr imethy 1 phenoxy)-J 1 , 1 "d i iodopropanesul fonan i 1 i de i s produced; reacting 3,5-di iodo-4- (2-methoxyphenoxy)anil ine with butanes ul fonyl chloride the correspond! ng, 31 ,5'-di iodo-4'- (2-methoxyphenoxy)butanesu 1 fonan i 1 ide is produced; reacting 3, -dibromo-4- (3-butoxyphenoxy)ahi 1 ine with methanesu 1 fonyl chloride the corresponding 31 ,51 -d i b rorno-4 ' -(3-butoxyphenoxy )methanesul fonan il i de is produced; etc. 2312 EXAMPLE I I: Preparation of N-methy 1 -4 ' - phenoxymet.hane- sulfonan? 1 ide 4'-Phenoxymethanesulfonarii 1 ide (about 10 grams) was dissolved in dry tetrahydro uran (about 100 millil iters). To the resulting solution was added potassium tert.-butoxi de (about .5 grams) and methyl iodide (about 15 mi 11 i 1 i ters) , and the produced admixture was st i rred for about 4 hours, and then the tetrahydrof uran was removed by evaporation in vacuo. The obtained residue was dissolved in methylene chloride-water, and the produced organic layer was separated. The organic layer was washed well with dilute aqueous sodium hydroxide and water, and then dried over magnesium sulfate. The dried organic layer was evaporated i n vacuo and the produced solids recrystal 1 i zed from ethyl acetate-mixed hexanes. About 7.7 grams of crystals o o melting at 112 C. to 113 C. was obtained. The crystals were identified as N-methyl - ^ - phenoxymethanesul fonan i 1 i de, obtained in about 73 percent yield. -Analysis for Ci4Hi5N03S: Calc'd.: C, 60.63; H, 5.45; N, 5.05; S, .11.56.
Found:. C, 60.56; H, 5.68; N, 5.17; S, 11.45.
EXAMPLE I II: Preparation of N- [2- (diethylamino)ethyi]-4'- - phenoxymethanesul fonan i 1 ide - 41 - Phenoxymethanesu 1 fonani 1 ide (about 16.75 grams), potassium tert. -butox ide (about 23.5 grams), N, N-diethyl -2-chloroethylamine hydrochloride (about 22 grams), and dry tetra-hydrofuran (about 200 mi 11 i 1 i ters) were admixed, stirred at about room temperature for about 4 hours, and then heated under reflux for about 30 hours.
Thereafter, the tetrahydrof uran was removed by evaporation in vacuo, and the produced residue dissolved in methylene chloride-water.. The obtained organic layer was separated and 231 washed well with di 1 ute aqueous sodium hydroxide and water, and then dried over sodi urn sul fate. The dried organic layer was evaporated in vacuo and the residue therefrom crystallized from ethyl al cohol -water . o o About 10.6 grams of crystals melting at 71 C. to 75 C. . - o o and resolidif ing and melting at 8 C. to 86 C. was~obtained.
One recrysta'l 1 i zation from ethyl alcohol yielded crystals melting at 71° C. to 75° C. and reso 1 i d i f y i ng and melting at o ° 86 C. to 87 C. The crystals were identified as N-[-2- (diethyl- _ ami no)ethyl ]- '-phenoxyme thanes ul fonani 1 ide,, obta i ned in about 6. percent yield.
Analysis for CigHaeNsOaS: Calc'd.: C, 62.95; H, 7-25; N, 7-75'; S, 8.85...
Found: C, 62.92; H, 7-21; N, 7.73; S, 8.82.
In a manner similar to Example I I I but using N, N-d ibuty 1 2-chloroethylamine hydrochloride in 1 ieu of N, N- diethyl -2-chloroethy lamine hydrochloride the correspond! ng N- [2- (dibutyl-ami no)ethyl J-^'-phenoxymethanesul fonani 1 ide can be prepared; using Ν,Ν-diethyl -jj-chloropropy lamine hydrochloride the correspond! ng N- [3- (d i ethy 1 ami no)propy 1 ] - 1 -phenoxymethane-sul fonan i 1 i de can be prepared; using N-methyl-N-propyl-J-chloropropylamine hydrochloride the corresponding N-[j5~ (N-methy 1-N-propy lamino)propyl ]- ·-phenoxymethanesulfonani 1 ide can be prepared; using N- (2-chloroethyl )piperidine the corresponding N- (2-piperidinoethyl )- '-phenoxymethanesulfonani 1 ide can be prepared; using N- (3-chloropropyl )piperidine the corresponding N- (3~ piperidinopropyl )- '-phenoxymethanesu1 fonani 1 ide can be prepared; using N- (2-chloroeth l pyrrolidine the correspond! ng N- [2-(1-pyrrol idinyl )ethyl ]- 4-phenoxymethanesulfonani 1 ide can be prepared; using N- (j-chloropropyl )pyrrol idine the Corresponding N-[J- (1-pyrrol idinyl )propyl ] - '- phenoxymethanesu lfonani 1 ide can be prepared; using N- (2-ch loroethyl )morphol i ne the corresponding N- (2-mo hoi inoethyl ) -4 ·- phenoxymethanesu Ifonan i 1 ide can. be prepared; usi ng N- (3~chloropropyl )morphol ine the corresponding N-(3-morphol i nop ropy 1 )- ' -phenoxymethanesu 1 fonan i 1 ide can be prepared; etc.

Claims (1)

1. A 4' -phenoxyalkanesulfonani lide represented by the formula wherein X is a g of halo, alky/I containing from 1 to carbon atoms, inclusive, and alkoxy containing from 1 to carbon atoms, , i ncl us ive; Y is halo; 1 is a member of the grouping consisting of hydrogen, al kyl con-taining from ! to 4 carbon atoms, inclusive, 2-piperidinoethyl , 3-piperidinopropyl, 2- (1-pyrrol i di ny )ethy 1 , .3- (1-pyrrol idihyl )-propyl, 2-morpholi noethy 1 , 3-morphol i noprppy 1 , and dial kyl ami no-alkyl of the formula where R and R4 are alkyl containing from 1 to 4 carbon atoms, inclusive; R2 is alkyl containing f rom 1 to 6 carbon atoms, inclusive; m is an integer having a value of zero to 3, inclusive; n is an integer having a value of zero to 2, inclusive; and k is an integer having a value of 2 to 3* inclusive; and the corresponding acid addition salts. ' ■ , ' ' - -2- The 4 '-phenoxyal kanesul fonani l ide i n accordance with clair 1 wherein Rl is hydrogen, R2 is methyl, and m and n have a · val ue of zero. -3- '' ■·■. ' The 4 '-phenoxyal kanesul fonani 1 ide in accordance with claim 1 wherein Rl and Ra are methyl , and m and n have a value of zero. -4- The 4'-phenoxyalkanesu1foriani 1 ide in accordance with claim ! wherein R1 i s dial kylaminoal ky 1 wi th R3 and R4 both ethyl and k has a value of 2, R2 is methyl, and m and n have a value of zero. '.. -5- . - . A method for producing a ^'-phenoxyalkanesulfonani 1 ide represented by the formula wherein X is a member of the grouping consisting of halo, alkyl containing from 1 to 4 carbon atoms, inclusive, and alkoxy containing from 1 to 4 carbon atoms, inclusive; Y is halo; R5 is a member of the grouping consisting of hydrogen and alkyl containing from 1 to 4 carbon atoms, inclusi e; R2 is alkyl containing from 1 to 6 carbon atoms, inclusive; m is an integer having a value of zero to 3* inclusive; n is an integer having a value of zero to 2, inclusive; and k is an integer having a value of 2 to 5, inclusive; which comprises reacting a phenoxy-ani 1 ine represented by the formula wherein X, Y, R , m, and n have the same meaning as above, with an al kanesul fonyl hal ide represented by the formula Halogen -S02-R2 2 wherein R has the same meaning as above, at a temperature in the range from about 0° C. to about 60° C. A method for producing represented by the formula •wherein X is a member of the group ng consisting of halo, alkyl containing from 1 to 4 carbon atoms, inclusive, and alkoxy containing from 1 to 4 carbon. atoms > inclusive; Y is halo; R is alkyl containing from 1 to 6 carbon atoms, Inclusive; Re is a member of the grouping consisting of alkyl containing from 1 to 4 carbon atoms, inclusive, 2-piperidinoethyl, 3-piperldinopropyl , 2- .(1- yrrol idinyl )ethyl, 3- (1-pyrrol idinyl )-. propyl, 2-morphol inoethyl, 3-
IL30223A 1967-07-18 1968-06-21 Lipid-normalizing 4'-phenoxy alkanesulfonanilides IL30223A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US65406467A 1967-07-18 1967-07-18

Publications (2)

Publication Number Publication Date
IL30223A0 IL30223A0 (en) 1968-08-22
IL30223A true IL30223A (en) 1971-08-25

Family

ID=24623305

Family Applications (1)

Application Number Title Priority Date Filing Date
IL30223A IL30223A (en) 1967-07-18 1968-06-21 Lipid-normalizing 4'-phenoxy alkanesulfonanilides

Country Status (5)

Country Link
US (1) US3531522A (en)
BE (1) BE718228A (en)
FR (1) FR1586894A (en)
GB (1) GB1204946A (en)
IL (1) IL30223A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1914367A1 (en) * 1969-03-21 1970-10-01 Bayer Ag 2,2 ', 4,4'-tetrachloro-5,5'-diamino-diphenyl ether
DE2845996A1 (en) * 1978-10-23 1980-04-30 Bayer Ag HERBICIDAL AGENTS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING WEEDS
PT86407B (en) * 1986-12-31 1990-11-20 Fujisawa Pharmaceutical Co METHOD FOR PREPARING NEW ALCANO-SULFONANILIDA DERIVATIVES, AND OF PHARMACEUTICAL COMPOSITIONS UNDERSTANDING THE SAME
DE4300696A1 (en) * 1993-01-13 1994-07-14 Roemmers Sa Substituted N-aminoalkyl methanesulfanilides as antispasmodics

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL279361A (en) * 1961-06-07 1900-01-01

Also Published As

Publication number Publication date
FR1586894A (en) 1970-03-06
IL30223A0 (en) 1968-08-22
GB1204946A (en) 1970-09-09
US3531522A (en) 1970-09-29
BE718228A (en) 1969-01-20

Similar Documents

Publication Publication Date Title
CZ222392A3 (en) Amino substituted piperazine derivatives
EP0109562A1 (en) Succinimide derivatives and their production
DK159420B (en) N- (PIPERIDINYL-ALKYL) CARBOXAMIDES AND SALTS THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS, AND THE USE OF THE COMPOUNDS FOR THE PREPARATION OF ANTI-CYPOTIC PHARMACEUTICAL PREPARATIONS
DK161075B (en) 10-SUBSTITUTED 1,8-DIHYDROXY-9 ANTHRONS AND THEIR USE IN COSMETICS
SU1628854A3 (en) Method for preparing quaternary organic ammonium compounds or their pharmaceutically acceptable salts
CS271469B2 (en) Method of phenoxyalkylcarboxyl acid&#39;s derivatives production
AU609359B2 (en) New indolylpropanols, processes for their preparation and their use, and preparations containing the compounds
JPH0745474B2 (en) Method for producing 1-hydroxy-2-pyridone
IL30223A (en) Lipid-normalizing 4&#39;-phenoxy alkanesulfonanilides
KR20030024919A (en) N-(3,5-dichloro-2-methoxyphenyl)-4-methoxy-3-piperazin-1-yl-benzenesulfonamide
EP0170460B1 (en) Derivatives of N-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]amine
JP3053418B2 (en) Novel substituted alkylpiperidines and their use as cholesterol synthesis inhibitors
US4271188A (en) Compounds having hypolipidaemic activity
US3531523A (en) N-(phenoxyphenyl)sulfamides
EP0230020A2 (en) 1,2,3,4,4a,9b-Hexahydro-4a-aminoalkyldibenzofurans, a process for their preparation and their use as medicaments
US4198509A (en) Mercaptoacylpiperazine carboxylic acid compounds
EP0101951A1 (en) 1,3-Dioxolo(4,5-g)quinolines and preparation thereof
US4259334A (en) Piperazines and therapeutic utility
US4010280A (en) Phenoxyalkylamine derivatives and preparation thereof
US4272536A (en) Novel tricycloundecane aminoacid amide
US3988371A (en) Meta-[2-(benzylamino)-ethyl] benzoic acid amides
DK149889B (en) METHOD OF ANALOGUE FOR THE PREPARATION OF DIBENZO (D, G) (1,3,6) DIOXAZOCINE DERIVATIVES OR ACID ADDITION SALTS THEREOF
KR940005959B1 (en) Method for preparing aminobenzamide derivatives
EP0301549A1 (en) 1-[2-(Phenylmethyl)phenyl]-piperazine compounds, a process for preparing them and pharmaceutical compostions containing them
US4709026A (en) Ketosultams