IL36983A - N-(p-beta-(8-quinolinylcarboxamidoethyl)-benzenesulphonyl)-ureas and process for their manufacture - Google Patents
N-(p-beta-(8-quinolinylcarboxamidoethyl)-benzenesulphonyl)-ureas and process for their manufactureInfo
- Publication number
- IL36983A IL36983A IL36983A IL3698371A IL36983A IL 36983 A IL36983 A IL 36983A IL 36983 A IL36983 A IL 36983A IL 3698371 A IL3698371 A IL 3698371A IL 36983 A IL36983 A IL 36983A
- Authority
- IL
- Israel
- Prior art keywords
- group
- benzenesulphonyl
- substituted
- urea
- carbon atoms
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (2)
1. HOE 70/F Q96K we claim is : Benzenesulphonyl urea derivatives of the formula in which X represents a hydrogen, chlorine or "bromine atom, a methoxy or methyl group, Y represents -CH(CH5)-CH2-, -CH2-CH(CH5)- or preferably R represents a) an alkyl group of 3 to 6 carbon atoms, b) a cycloalkyl group of 5 to 8 carbon atoms, which may be substituted by 1 or 2 alkyl groups of up to 3 carbon atoms in total or by a chlorine atom, c) a cycloalkenyl group of 5 to 8 carbon, atoms, which may be substituted by 1 or 2 alkyl groups of 3 carbon atoms in total, d) a bicycloalkyl or bicycloalkenyl group of 7 or 8 carbon atoms, e) a nortricyclyl group, fjg) an alkylene-imino radical of 3 to 7 carbon atoms in the ring, which may be unoaturatod or substituted by 1 or 2 methyl groups or a lower alkyl group or a methoxy group, 36983/2 . ·» Z represents a hydrogen atom or a methylene or dlmethylene group, which forms together with Y a 5- or 6- membe ed ring* and the salts thereof.
2. ) N^^*6*ohloro»quinolino-8*oarboxamido-ethyl)-benzene-sulphonyl/- *•cyclohexyl*«rea. sulphonyl^-N'·(4»methyl cyclohexyl)-urea. 8) -^5-(p»6^ohloro-quinolino-8-carboxamido-ethyl)-benzene- sulphonyl/*!*1*(3*methyl^pentamethylene)«·semicarbazide. HOE 70/F Q96K 9) 4-/ -( B-6-chloro-quinolino-8-carboxamido-ethyl)-benzene- sulphonyl/-l,l-pentamethylene-semicarbazide. 10) 4- 4-( B-6-chloro-quinolino-8-carboxamido-ethyl)-benzene- sulphony1/-1 ,1-hexamethylene-semicarbazide . 11) 4- -( B-6-chloro-quinolino-8-carboxamido-ethyl)-benzene- 8ulphonyl7~l , 1-( 3-ethy1-pentamethylene )-semicarbazide . 12) 4-/4-(β-6-bromo-quinolino-8-carboxamido-ethyl)-benzene- sulphonyl7~l , i-hexamethylene-semicarbazide . 13). A process for the manufacture of benzenesulphonyl-ureas as claimed in claim 1, which comprises introducing, optionall stepwise, into a compound containing the grouping I of the formula in which n is 0,1 or 2. a radical II of the formula and a radical III of the formula - CO - NH - R III radicals I and III being linlced by means of a NH- group contained either in radical I or in radical III, . ": optionally oxidizing the reaction products subsequently and treating them, where required, with alkaline agents or physiologically tolerable inorganic or organic acids, for salt formation. HOE 70/P 096K 14) A process for the manufacture of benzenesulphony1-ureas of the formula in which X represents a hydrogen, chlorine or "bromine atom, a methoxy or methyl group, Ϊ represents -CH(0H5)-CH2-f- -CH2-CH(CH5)- or preferably -CH2-CH2~ , R represents a) an alkyl group, of 3 to 6 carbon atoms, b) a cycloalkyl group of 5 to 8 carbon atoms, which may be substituted by 1 or 2 alkyl groups of up to 3 carbon atoms in total or by a chlorine atom, c) a cycloalkenyl group of 5 to 8 carbon atoms, which may be substituted by 1 or 2 alkyl groups of 3 carbon atoms in total, d) a bicycloalkyl or bicycloalkenyl group of 7 or 8 carbon atoms, e) a nortricyclyl group, . f) a opiro 2,fl7"heptyl grou ?. Mffaytfie cr et 'meM /en represents a hydrogen atom or a h^4^-ea- ¾-G?i^ r€-al—oLJl—c - Or oa-rbon a-e-m-e-, which forms together with Y a 5- or 6-raembered ring, and the salts thereof, as claimed in Claim 13, which comprises a) reacting a benzenesulphonyl-isocyanate , benzenesul- phonyl-carbamic acid ester, benzenesulphon 1-thiolcar- bamic acid ester, benzenesulphonyl-urea, benzenesulphonyl- HOE 70/F Q96K with an amine R-NHg or Bait thereof, or reacting a sul-phonamide of the formula or a salt thereof with a R^-substituted isocyanate, car-baDiic acid ester, thiolcarbamic acid ester, carbamic acid halide or urea; saponifying or hydrolysing a correspondingly substituted benzenesulphonyl-isourea ether, benzenesulphonyl-isourea ester, benzenesulphonyl- isothiourea ether, benzenesul" phonyl-isothiourea ether , benzenesulphonyl-parabanic acid or benzenesulphonyl- haloformic acid amidine or a compound of the formula wherein U stands for cocygon^lower-a-3rrey-i , sul hur-1pwe-κ- al½yl or halogen (preferably chlorine) ; replacing in a correspondingly substituted benzenesul- phony1-thiourea or thioamido-alk l-benzenesulphonyl- urea or -thiourea, the sulphur atom or sulphur atoms of the thio-urea and/or thio-amido group by an oxygen atom or oxygen atoms , or adding' ater to a correspondingly substituted carbodiimide ; Oxidizin a corres ondin l substituted benzenesul hin l V e) introducing the group "by acylation optionally in one or more steps, into a benzenesulphony1-urea of ■ he - formula reacting a correspondingly substituted benzenesulphonyl- halide v/ith a R-substituted urea or an alkali metal salt thereof; or reacting a correspondingly substituted benzene sulphinic acid halide or, in the presence of an acid condensation agent, even a correspondingly substituted sulphinic acid or alkali metal salt thereof with N-R-N' -hydroxy-urea ; and, where required, treating the reaction product so obtained with an alkaline agent or with a physiologically acceptable inorganic or organic acid, for salt formation. A process for the manufacture of benzenesulphonyl-ureas in which X represents a hydrogen, chlorine or bromine atom, or a methyl or methoxy group, Y represents Z represents -carbon a ome, which forms together with Ϊ a 5- or 6- an alkylene-imino radical of 3 to 7 carbon atoms in the ring, which may be unsaturated or substituted by 1 or 2. methyl groups or a lower alkyl group or a methoxy group, a pentamethylene-imino radical which is substituted by an endoalkylene group of 1 to 3 carbon atoms, a hexamethylene-imino radical which is substituted by an endoethylene group in β-ε-positbn, or a tetrahydro-isoindoline, a 4 , 7~endoalkylene-hexa-hydro- or -tetrahydro-isoindoline radical, the endoalkylene group containing 1 or 2 carbon atoms and the double bond of the tetrahydro compound being in 5,6- position, and the salts thereof, as claimed in claim 13, which comprises reacting a benzenesulphonamide of the formula or a salt thereof, with an imino-carbamic acid ester, imino-thiocarbamic acid ester or imino-urea containing as the imino group the group R-, reacting an amine of the formula RNH2 or a salt thereof with a benzenesulphonyl-isocyanate , benzensul-phonyl-carbamic acid ester, benzenesulphonyl-thiol-carbamic acid ester, benzenesulphonyl-carbamic acid halide or benzene-sulphonyl-urea, substituted in3-position by the group Z and in 4-position by the group reacting a benzenesulphochloride of the formula with a R-substituted urea, hydrolizing a benzenesulphonyl-isourea ether, ben-zenesulphonyl-isothiourea ether or benzene-sul hon 1 imino-parabahic acid derivative substituted by R, Z and replacing in a benzenesulphonylr-thiourea of the formula the sulphur atom by an oxygen atom, or introducing the radical 36933/2 v optionally step by step, into a benzene sulphonyl- urea of the formula Π 2Ν " Y 5 C) 'J- ~ NH " C0 ~ HH ~ U and, where required, treating the reaction product for salt formation with an alkaline agent or a ph siologically acceptable inorganic or organic acid. 16) Λ process for the manufacture of pharmaceutical preparations for oral administration and lowering the blood sugar level in the treatment of diabetes mellitus, which comprises bringing a benzenesulphonyl-urea of the formula specified in claim 1 or a salt thereof, optionally in admixture or conjunction with a suitable carrier, into a pharmaceutically suitable dosage unit form. 17) Pharmaceutical preparations for oral administration and lov/ering the blood sugar level in the treatment of diabetes mellitus, which comprise a content of a benzenesulphonyl-urea defined in claim 1 or a salt thereof.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702027950 DE2027950A1 (en) | 1970-06-06 | 1970-06-06 | Benzenesulfonylureas and process for their preparation |
DE19712120266 DE2120266A1 (en) | 1971-04-26 | 1971-04-26 | Benzenesulfonyl semicarbazides and processes for their preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
IL36983A0 IL36983A0 (en) | 1971-08-25 |
IL36983A true IL36983A (en) | 1976-03-31 |
Family
ID=25759238
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL36983A IL36983A (en) | 1970-06-06 | 1971-06-04 | N-(p-beta-(8-quinolinylcarboxamidoethyl)-benzenesulphonyl)-ureas and process for their manufacture |
Country Status (15)
Country | Link |
---|---|
BE (1) | BE768135A (en) |
BG (1) | BG19796A3 (en) |
CA (1) | CA986114A (en) |
CH (12) | CH576972A5 (en) |
DK (1) | DK138793C (en) |
ES (3) | ES391792A1 (en) |
FI (1) | FI50792C (en) |
FR (1) | FR2100731A1 (en) |
HU (1) | HU166708B (en) |
IE (1) | IE35332B1 (en) |
IL (1) | IL36983A (en) |
IT (1) | IT1037032B (en) |
NL (1) | NL7107502A (en) |
RO (1) | RO58731A (en) |
SE (1) | SE361038B (en) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1294957B (en) * | 1966-07-02 | 1969-05-14 | Boehringer & Soehne Gmbh | Process for the preparation of hydrindene sulphonylureas and sulphonyl semicarbazides |
-
1971
- 1971-05-31 ES ES391792A patent/ES391792A1/en not_active Expired
- 1971-06-01 NL NL7107502A patent/NL7107502A/xx unknown
- 1971-06-01 BG BG17705A patent/BG19796A3/xx unknown
- 1971-06-03 RO RO70340A patent/RO58731A/ro unknown
- 1971-06-03 FI FI711544A patent/FI50792C/en active
- 1971-06-03 IE IE719/71A patent/IE35332B1/en unknown
- 1971-06-04 IL IL36983A patent/IL36983A/en unknown
- 1971-06-04 CH CH1021875A patent/CH576972A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1022175A patent/CH576971A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021975A patent/CH577498A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1022075A patent/CH576973A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021775A patent/CH586219A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021575A patent/CH586203A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021375A patent/CH577974A5/xx not_active IP Right Cessation
- 1971-06-04 CA CA114,786A patent/CA986114A/en not_active Expired
- 1971-06-04 CH CH815771A patent/CH568291A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021275A patent/CH577478A5/xx not_active IP Right Cessation
- 1971-06-04 SE SE07223/71A patent/SE361038B/xx unknown
- 1971-06-04 BE BE768135A patent/BE768135A/en unknown
- 1971-06-04 IT IT25459/71A patent/IT1037032B/en active
- 1971-06-04 DK DK273471A patent/DK138793C/en active
- 1971-06-04 CH CH1021475A patent/CH576965A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021675A patent/CH577479A5/xx not_active IP Right Cessation
- 1971-06-04 HU HUHO1381A patent/HU166708B/hu unknown
- 1971-06-07 FR FR7120494A patent/FR2100731A1/en active Granted
-
1973
- 1973-08-22 ES ES418120A patent/ES418120A1/en not_active Expired
-
1976
- 1976-01-31 ES ES444834A patent/ES444834A1/en not_active Expired
- 1976-03-25 CH CH815771A patent/CH580593A5/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
RO58731A (en) | 1975-12-15 |
DK138793B (en) | 1978-10-30 |
DK138793C (en) | 1979-03-26 |
CH576971A5 (en) | 1976-06-30 |
CH580593A5 (en) | 1976-10-15 |
CH577479A5 (en) | 1976-07-15 |
ES418120A1 (en) | 1976-09-01 |
CH576972A5 (en) | 1976-06-30 |
CH576973A5 (en) | 1976-06-30 |
ES444834A1 (en) | 1977-05-01 |
CA986114A (en) | 1976-03-23 |
SE361038B (en) | 1973-10-15 |
FI50792C (en) | 1976-07-12 |
IL36983A0 (en) | 1971-08-25 |
CH568291A5 (en) | 1975-10-31 |
BG19796A3 (en) | 1975-10-10 |
CH577974A5 (en) | 1976-07-30 |
CH586203A5 (en) | 1977-03-31 |
CH577478A5 (en) | 1976-07-15 |
IE35332L (en) | 1971-12-06 |
CH586219A5 (en) | 1977-03-31 |
BE768135A (en) | 1971-12-06 |
CH576965A5 (en) | 1976-06-30 |
ES391792A1 (en) | 1974-08-01 |
NL7107502A (en) | 1971-12-08 |
CH577498A5 (en) | 1976-07-15 |
HU166708B (en) | 1975-05-28 |
IE35332B1 (en) | 1976-01-21 |
FR2100731A1 (en) | 1972-03-24 |
IT1037032B (en) | 1979-11-10 |
FI50792B (en) | 1976-03-31 |
FR2100731B1 (en) | 1974-09-06 |
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