ES418120A1 - Procedure for the preparation of sulfonil-ureas. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the preparation of sulfonil-ureas. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES418120A1 ES418120A1 ES418120A ES418120A ES418120A1 ES 418120 A1 ES418120 A1 ES 418120A1 ES 418120 A ES418120 A ES 418120A ES 418120 A ES418120 A ES 418120A ES 418120 A1 ES418120 A1 ES 418120A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- benzenesulfonyl
- formula
- salts
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 5
- -1 spiro [2,4] -heptyl Chemical group 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 235000013877 carbamide Nutrition 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 abstract 2
- 150000003672 ureas Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229940100389 Sulfonylurea Drugs 0.000 abstract 1
- AODMIOGGMWOSDI-UHFFFAOYSA-N [3-(benzenesulfonyl)thiophen-2-yl]carbamic acid Chemical class S1C=CC(S(=O)(=O)C=2C=CC=CC=2)=C1NC(=O)O AODMIOGGMWOSDI-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001409 amidines Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzene seleninic acid Natural products O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 abstract 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005293 bicycloalkoxy group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229960001330 hydroxycarbamide Drugs 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 150000003455 sulfinic acids Chemical class 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 abstract 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (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)
Abstract
Procedure for the preparation of sulfonylureas of the formula **(See formula)** where X means hydrogen, chlorine, bromine, methoxy or methyl, Y means -CH (CH3) -CH2-, -CH2-CH (CH3) - or, preferably, -CH2-CH2-, R means, a) alcohol with 3 to 6 carbon atoms, b) cycloalkyl with 5 to 8 carbon atoms, which may be optionally substituted by 1 or 2 alcohol groups with a total of 3 carbon atoms or chlorine, c) cycloalkenyl with 5 to 8 carbon atoms which may optionally be replaced by a total of 3 carbon atoms, d) bicycloalkoxy or bicycloalkenyl with 7 to 8 carbon atoms, e) nortricicycl, f) spiro [2,4] -heptyl, and z means hydrogen or a hydrocarbon radical with 1 or 2 carbon atoms that form with Y a 5- or 6-membered ring and its salts, characterized in that a) benzenesulfonyl-isocyanates, benzenesulfonyl-carbamic acid esters, benzenesulfonyl-thiolcarbamic acid esters, benzenesulfonylureas are reacted, - semicarbazides or -semicarbazones substituted in position 4 with the group **(See formula)** or in position 3 with group Z with an amine R-NH2 or its salts, or sulfonamides of the formula are reacted **(See formula)** or its salts, with isocyanates, esters of carbamic acid, esters of thiolcarbamic acid, halides of carbamic acid or ureas, E-substituted; or b) suitably substituted benzenesulfonyl iso-urea-ethers, -isourea-esters, -isothiourea-ethers, benzenesulfonylparabanic acids or benzenesulfonyl-haloformic acid amidines, or compounds of the formula **(See formula)** wherein U means low molecular weight O-alcohol, low molecular weight S-alcohol or halogen (preferably chlorine); or c) in suitably substituted benzenesulfonyl-thiorureas, thioamidoalcohyl-benzenesulfonylureas or thioamidoaleohyl-benzenesulphonylthioureas, the sulfur atom or the sulfur atoms of the thiourea group and/or of the thioamido group is replaced by an oxygen atom or or suitably substituted carbodiimides are subjected to addition with water, or d) suitable benzenesulfinylureas or benzenesulfenylureas are oxidized, or e) in benzenesulfonylureas of the formula **(See formula)** the radical is introduced by acylation, optionally in stages. f) suitably substituted benzenesulfonyl halides are reacted with R-substituted ureas or their alkali metal salts, or suitably substituted benzenesulfinic acid halides or, in the presence of acidic condensing agents, also suitably substituted sulfinic acids or their salts are reacted of alkali metals, with NR-N'-hydroxy-urea; and the reaction products are optionally treated with alkaline agents for the formation of salts. (Machine-translation by Google Translate, not legally binding)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ES418120A1 true ES418120A1 (en) | 1976-09-01 |
Family
ID=25759238
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES391792A Expired ES391792A1 (en) | 1970-06-06 | 1971-05-31 | Procedure for the preparation of bencenosulfonilureas. (Machine-translation by Google Translate, not legally binding) |
| ES418120A Expired ES418120A1 (en) | 1970-06-06 | 1973-08-22 | Procedure for the preparation of sulfonil-ureas. (Machine-translation by Google Translate, not legally binding) |
| ES444834A Expired ES444834A1 (en) | 1970-06-06 | 1976-01-31 | Procedure for the preparation of semicarbazides. (Machine-translation by Google Translate, not legally binding) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES391792A Expired ES391792A1 (en) | 1970-06-06 | 1971-05-31 | Procedure for the preparation of bencenosulfonilureas. (Machine-translation by Google Translate, not legally binding) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES444834A Expired ES444834A1 (en) | 1970-06-06 | 1976-01-31 | Procedure for the preparation of semicarbazides. (Machine-translation by Google Translate, not legally binding) |
Country Status (15)
| Country | Link |
|---|---|
| BE (1) | BE768135A (en) |
| BG (1) | BG19796A3 (en) |
| CA (1) | CA986114A (en) |
| CH (12) | CH586219A5 (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 BG017705A patent/BG19796A3/en unknown
- 1971-06-03 FI FI711544A patent/FI50792C/en active
- 1971-06-03 IE IE719/71A patent/IE35332B1/en unknown
- 1971-06-03 RO RO70340A patent/RO58731A/ro unknown
- 1971-06-04 CH CH1021775A patent/CH586219A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021275A patent/CH577478A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021475A patent/CH576965A5/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 CH1021975A patent/CH577498A5/xx not_active IP Right Cessation
- 1971-06-04 SE SE07223/71A patent/SE361038B/xx unknown
- 1971-06-04 CH CH1022075A patent/CH576973A5/xx not_active IP Right Cessation
- 1971-06-04 DK DK273471A patent/DK138793C/en active
- 1971-06-04 HU HUHO1381A patent/HU166708B/hu unknown
- 1971-06-04 CH CH1021675A patent/CH577479A5/xx not_active IP Right Cessation
- 1971-06-04 BE BE768135A patent/BE768135A/en unknown
- 1971-06-04 CH CH1022175A patent/CH576971A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021575A patent/CH586203A5/xx not_active IP Right Cessation
- 1971-06-04 CH CH1021875A patent/CH576972A5/xx not_active IP Right Cessation
- 1971-06-04 IT IT25459/71A patent/IT1037032B/en active
- 1971-06-04 CH CH815771A patent/CH568291A5/xx not_active IP Right Cessation
- 1971-06-04 IL IL36983A patent/IL36983A/en 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 |
|---|---|
| CH577478A5 (en) | 1976-07-15 |
| NL7107502A (en) | 1971-12-08 |
| CH576972A5 (en) | 1976-06-30 |
| FI50792C (en) | 1976-07-12 |
| FR2100731B1 (en) | 1974-09-06 |
| BG19796A3 (en) | 1975-10-10 |
| RO58731A (en) | 1975-12-15 |
| HU166708B (en) | 1975-05-28 |
| DK138793C (en) | 1979-03-26 |
| CH576971A5 (en) | 1976-06-30 |
| IL36983A (en) | 1976-03-31 |
| IE35332L (en) | 1971-12-06 |
| SE361038B (en) | 1973-10-15 |
| BE768135A (en) | 1971-12-06 |
| IL36983A0 (en) | 1971-08-25 |
| ES444834A1 (en) | 1977-05-01 |
| CH580593A5 (en) | 1976-10-15 |
| FI50792B (en) | 1976-03-31 |
| CH586219A5 (en) | 1977-03-31 |
| DK138793B (en) | 1978-10-30 |
| FR2100731A1 (en) | 1972-03-24 |
| ES391792A1 (en) | 1974-08-01 |
| CH577498A5 (en) | 1976-07-15 |
| CH586203A5 (en) | 1977-03-31 |
| CA986114A (en) | 1976-03-23 |
| CH577479A5 (en) | 1976-07-15 |
| CH576965A5 (en) | 1976-06-30 |
| CH577974A5 (en) | 1976-07-30 |
| IE35332B1 (en) | 1976-01-21 |
| IT1037032B (en) | 1979-11-10 |
| CH576973A5 (en) | 1976-06-30 |
| CH568291A5 (en) | 1975-10-31 |
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