IE35084L - Diaryl sulphonyl ureas - Google Patents
Diaryl sulphonyl ureasInfo
- Publication number
- IE35084L IE35084L IE111970A IE111970A IE35084L IE 35084 L IE35084 L IE 35084L IE 111970 A IE111970 A IE 111970A IE 111970 A IE111970 A IE 111970A IE 35084 L IE35084 L IE 35084L
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- hydrogen
- halogen
- formula
- methyl
- Prior art date
Links
- -1 Diaryl sulphonyl ureas Chemical class 0.000 title abstract 2
- 235000013877 carbamide Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract 2
- 206010002383 Angina Pectoris Diseases 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229940125890 compound Ia Drugs 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 229940101209 mercuric oxide Drugs 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910001923 silver oxide Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 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 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
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- 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
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1308210 Benzenesulphonyl urea compounds SCHERICO Ltd 26 Aug 1970 [27 Aug 1969 14 Nov 1969 19 Dec 1969] 41106/70 Heading C2C Novel compounds of the Formula I their d- or l-isomers or racemates and pharmaceutically acceptable salts thereof, wherein X and X<SP>1</SP> are hydrogen, methyl, methoxy or halogen, Y is C 1-6 alkyl, hydroxy, C 1-6 alkoxyl or halogen and Y<SP>1</SP> is hydrogen, C 1-6 alkyl or alkoxy, hydroxy or halogen and R is hydrogen or methyl may be prepared by (a) reacting a reactive derivative including isocyanates of a carbamic acid, E<SP>1</SP>:NCOOH, with an amino compound E<SP>2</SP>:NH or a reactive derivative thereof, wherein one of E<SP>1</SP> and E<SP>2</SP> is and the other is (b) reacting a reactive derivative of an acid and a urea wherein p is 1 or 2; (c) reducing a compound of the Formula IA wherein W<SP>1</SP> and W<SP>2</SP> are hydrogen, halogen or diazonium, R<SP>2</SP> is a group removable by hydrogenolysis to give R 2 =H, n is 0 or 1 and M is one of the following groups wherein R<SP>1</SP> is hydrogen, methyl or a group removable by hydrogenolysis to give R<SP>1</SP> = H and L is a methylene or a group CHBH or C = B where B is oxygen or sulphur, wherein compound IA differs from compound I in at least one structural feature; (d) oxidizing a compound of the Formula XV wherein m is 0 or 1; (e) subjecting a compound XVI (i) to hydrolysis when A is imino or iminolether or (ii) reaction with mercuric oxide or silver oxide when A is sulphur; (f) modifying the substituents on the benzene rings to form X,X<SP>1</SP>, Y, Y<SP>1</SP> components as in Formula I. Pharmaceutical compositions of the compounds I with the usual excipients show antiarrhythmic and anti-angina activity when administered orally or parenterally.
[GB1308210A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85350469A | 1969-08-27 | 1969-08-27 | |
| US87700069A | 1969-11-14 | 1969-11-14 | |
| BR21539369A BR6915393D0 (en) | 1969-08-27 | 1969-12-19 | PROCESS FOR THE PREPARATION OF NEW COMPOUNDS OF BENZENE SULFONYL-UREA |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35084L true IE35084L (en) | 1971-02-27 |
| IE35084B1 IE35084B1 (en) | 1975-11-12 |
Family
ID=27160209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE111970A IE35084B1 (en) | 1969-08-27 | 1970-08-26 | Benzenesulfonyl urea compounds |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4911383B1 (en) |
| AT (1) | AT321930B (en) |
| BE (1) | BE755382A (en) |
| CA (1) | CA976188A (en) |
| CH (1) | CH582136A5 (en) |
| DE (1) | DE2042230A1 (en) |
| ES (1) | ES383043A1 (en) |
| FR (1) | FR2068521B1 (en) |
| GB (1) | GB1308210A (en) |
| IE (1) | IE35084B1 (en) |
| IL (1) | IL35170A (en) |
| NL (1) | NL7012544A (en) |
| NO (1) | NO135286C (en) |
| PL (1) | PL82799B1 (en) |
| SE (1) | SE385582B (en) |
| SU (1) | SU464108A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579964A (en) * | 1983-03-31 | 1986-04-01 | Union Carbide Corporation | Alkoxysilyl functional silicones |
-
0
- BE BE755382D patent/BE755382A/en unknown
-
1969
- 1969-08-27 SU SU691471980D patent/SU464108A3/en active
-
1970
- 1970-08-25 CH CH1270970A patent/CH582136A5/xx not_active IP Right Cessation
- 1970-08-25 NL NL7012544A patent/NL7012544A/xx unknown
- 1970-08-26 AT AT773670A patent/AT321930B/en not_active IP Right Cessation
- 1970-08-26 FR FR7031187A patent/FR2068521B1/fr not_active Expired
- 1970-08-26 ES ES383043A patent/ES383043A1/en not_active Expired
- 1970-08-26 NO NO324070A patent/NO135286C/no unknown
- 1970-08-26 CA CA091,692A patent/CA976188A/en not_active Expired
- 1970-08-26 IE IE111970A patent/IE35084B1/en unknown
- 1970-08-26 JP JP7433970A patent/JPS4911383B1/ja active Pending
- 1970-08-26 IL IL3517070A patent/IL35170A/en unknown
- 1970-08-26 SE SE1161070A patent/SE385582B/en unknown
- 1970-08-26 PL PL14289370A patent/PL82799B1/en unknown
- 1970-08-26 GB GB4110670A patent/GB1308210A/en not_active Expired
- 1970-08-26 DE DE19702042230 patent/DE2042230A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SU464108A3 (en) | 1975-03-15 |
| NL7012544A (en) | 1971-03-02 |
| BE755382A (en) | 1971-03-01 |
| DE2042230A1 (en) | 1971-03-04 |
| CH582136A5 (en) | 1976-11-30 |
| FR2068521B1 (en) | 1974-08-30 |
| NO135286B (en) | 1976-12-06 |
| JPS4911383B1 (en) | 1974-03-16 |
| FR2068521A1 (en) | 1971-08-27 |
| IE35084B1 (en) | 1975-11-12 |
| PL82799B1 (en) | 1975-10-31 |
| IL35170A (en) | 1974-11-29 |
| SE385582B (en) | 1976-07-12 |
| NO135286C (en) | 1977-03-16 |
| ES383043A1 (en) | 1972-12-16 |
| CA976188A (en) | 1975-10-14 |
| AT321930B (en) | 1975-04-25 |
| GB1308210A (en) | 1973-02-21 |
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