SI9600033B - Substituted tiophensulfonyl ureas and thioureas, process for the preparation thereof, use thereof as medicine or as diagnostic as well as medicine containing them - Google Patents
Substituted tiophensulfonyl ureas and thioureas, process for the preparation thereof, use thereof as medicine or as diagnostic as well as medicine containing them Download PDFInfo
- Publication number
- SI9600033B SI9600033B SI9600033A SI9600033A SI9600033B SI 9600033 B SI9600033 B SI 9600033B SI 9600033 A SI9600033 A SI 9600033A SI 9600033 A SI9600033 A SI 9600033A SI 9600033 B SI9600033 B SI 9600033B
- Authority
- SI
- Slovenia
- Prior art keywords
- compound
- formula
- carbon atoms
- preparation
- hydrogen
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 8
- 238000000034 method Methods 0.000 title claims 7
- 150000003672 ureas Chemical class 0.000 title claims 2
- 235000013877 carbamide Nutrition 0.000 title 1
- 150000003585 thioureas Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229940125890 compound Ia Drugs 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- -1 aromatic sulfonamide Chemical class 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- KLPPUPBECAHKEF-UHFFFAOYSA-N thiophen-2-ylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CS1 KLPPUPBECAHKEF-UHFFFAOYSA-N 0.000 claims 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- ARDGWQBDKKYVBM-UHFFFAOYSA-N thiophen-2-ylsulfonylthiourea Chemical compound NC(=S)NS(=O)(=O)C1=CC=CS1 ARDGWQBDKKYVBM-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical class OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 102000016924 KATP Channels Human genes 0.000 claims 1
- 108010053914 KATP Channels Proteins 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 206010049418 Sudden Cardiac Death Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 238000006477 desulfuration reaction Methods 0.000 claims 1
- 230000023556 desulfurization Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000004217 heart function Effects 0.000 claims 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- JBPHCEHVHVSGEP-UHFFFAOYSA-N n-(oxomethylidene)thiophene-2-sulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CS1 JBPHCEHVHVSGEP-UHFFFAOYSA-N 0.000 claims 1
- GBAVRWCYORZZKO-UHFFFAOYSA-N n-(sulfanylidenemethylidene)thiophene-2-sulfonamide Chemical compound S=C=NS(=O)(=O)C1=CC=CS1 GBAVRWCYORZZKO-UHFFFAOYSA-N 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 230000033764 rhythmic process Effects 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- UVVUGWBBCDFNSD-UHFFFAOYSA-N tetraisocyanatosilane Chemical compound O=C=N[Si](N=C=O)(N=C=O)N=C=O UVVUGWBBCDFNSD-UHFFFAOYSA-N 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- MRNIIOROBHKDQQ-UHFFFAOYSA-N n-[2-[2-(carbamoylsulfamoyl)thiophen-3-yl]ethyl]benzamide Chemical compound S1C=CC(CCNC(=O)C=2C=CC=CC=2)=C1S(=O)(=O)NC(=O)N MRNIIOROBHKDQQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19503136A DE19503136A1 (de) | 1995-02-01 | 1995-02-01 | Substituierte Thiophenylsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9600033A SI9600033A (en) | 1996-10-31 |
| SI9600033B true SI9600033B (en) | 2001-12-31 |
Family
ID=7752837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9600033A SI9600033B (en) | 1995-02-01 | 1996-02-01 | Substituted tiophensulfonyl ureas and thioureas, process for the preparation thereof, use thereof as medicine or as diagnostic as well as medicine containing them |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5792788A (cs) |
| EP (1) | EP0729954B1 (cs) |
| JP (1) | JP4021949B2 (cs) |
| KR (1) | KR100449192B1 (cs) |
| CN (1) | CN1071752C (cs) |
| AR (1) | AR002026A1 (cs) |
| AT (1) | ATE248829T1 (cs) |
| AU (1) | AU700884B2 (cs) |
| BR (1) | BR9600290A (cs) |
| CA (1) | CA2168517C (cs) |
| CZ (1) | CZ290738B6 (cs) |
| DE (2) | DE19503136A1 (cs) |
| DK (1) | DK0729954T3 (cs) |
| ES (1) | ES2206525T3 (cs) |
| FI (1) | FI120768B (cs) |
| HR (1) | HRP960042B1 (cs) |
| HU (1) | HU226121B1 (cs) |
| IL (1) | IL116980A (cs) |
| MY (1) | MY113423A (cs) |
| NO (1) | NO315160B1 (cs) |
| NZ (1) | NZ280890A (cs) |
| PL (1) | PL183561B1 (cs) |
| PT (1) | PT729954E (cs) |
| RU (1) | RU2164916C2 (cs) |
| SI (1) | SI9600033B (cs) |
| SK (1) | SK284325B6 (cs) |
| TR (1) | TR199600079A2 (cs) |
| TW (1) | TW355184B (cs) |
| ZA (1) | ZA96720B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004061017A1 (de) * | 2004-12-18 | 2006-06-22 | Sanofi-Aventis Deutschland Gmbh | Piperidinsulfonylharnstoffe und -thioharnstoffe, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| CN115703730A (zh) * | 2021-08-16 | 2023-02-17 | 中国科学院上海药物研究所 | 磺酰脲化合物、制备方法及其应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124597A (en) * | 1964-03-10 | |||
| DE1493672C3 (de) * | 1964-08-01 | 1974-05-02 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DE1518874C3 (de) * | 1964-10-07 | 1975-03-13 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung |
| BE754588A (fr) * | 1969-08-07 | 1971-02-08 | Hoechst Ag | Thiophene-sulfonyl-urees et les medicaments qui contiennent cessubstances |
| DE2413514C3 (de) * | 1974-03-21 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | N-Acylaminoathylbenzolsulfonyl-N'-methylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
| ZA813332B (en) * | 1980-06-21 | 1982-05-26 | Pfizer | Larvicides and isecticides |
| ZA871109B (en) * | 1986-02-19 | 1987-10-28 | Duphar Int Res | New thio compounds having fungicidal activity |
| GB9012252D0 (en) * | 1990-06-01 | 1990-07-18 | Lilly Industries Ltd | Pharmaceutical compounds |
| ES2098069T3 (es) * | 1993-02-23 | 1997-04-16 | Hoechst Ag | Bencenosulfonil-ureas y -tioureas sustituidas, procedimiento para su preparacion y su utilizacion como agentes farmaceuticos. |
| DE4341655A1 (de) * | 1993-12-07 | 1995-06-08 | Hoechst Ag | Aminosubstituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika |
| DE4344957A1 (de) * | 1993-12-30 | 1995-07-06 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Herstellungsverfahren und Verwendungsmöglichkeiten pharmazeutischer Präparate auf Basis dieser Verbindungen |
-
1995
- 1995-02-01 DE DE19503136A patent/DE19503136A1/de not_active Withdrawn
-
1996
- 1996-01-26 PT PT96101096T patent/PT729954E/pt unknown
- 1996-01-26 DK DK96101096T patent/DK0729954T3/da active
- 1996-01-26 AT AT96101096T patent/ATE248829T1/de active
- 1996-01-26 DE DE59610691T patent/DE59610691D1/de not_active Expired - Lifetime
- 1996-01-26 NZ NZ280890A patent/NZ280890A/en not_active IP Right Cessation
- 1996-01-26 EP EP96101096A patent/EP0729954B1/de not_active Expired - Lifetime
- 1996-01-26 ES ES96101096T patent/ES2206525T3/es not_active Expired - Lifetime
- 1996-01-29 HR HR960042A patent/HRP960042B1/xx not_active IP Right Cessation
- 1996-01-29 TW TW085101042A patent/TW355184B/zh not_active IP Right Cessation
- 1996-01-29 PL PL96312532A patent/PL183561B1/pl not_active IP Right Cessation
- 1996-01-30 SK SK134-96A patent/SK284325B6/sk not_active IP Right Cessation
- 1996-01-30 US US08/593,621 patent/US5792788A/en not_active Expired - Lifetime
- 1996-01-30 CN CN96101109A patent/CN1071752C/zh not_active Expired - Fee Related
- 1996-01-30 AU AU42246/96A patent/AU700884B2/en not_active Ceased
- 1996-01-30 AR ARP960101212A patent/AR002026A1/es active IP Right Grant
- 1996-01-30 CZ CZ1996280A patent/CZ290738B6/cs not_active IP Right Cessation
- 1996-01-30 TR TR96/00079A patent/TR199600079A2/xx unknown
- 1996-01-30 MY MYPI96000343A patent/MY113423A/en unknown
- 1996-01-30 FI FI960430A patent/FI120768B/fi not_active IP Right Cessation
- 1996-01-31 IL IL11698096A patent/IL116980A/en not_active IP Right Cessation
- 1996-01-31 RU RU96101797/04A patent/RU2164916C2/ru not_active IP Right Cessation
- 1996-01-31 ZA ZA96720A patent/ZA96720B/xx unknown
- 1996-01-31 JP JP01575996A patent/JP4021949B2/ja not_active Expired - Lifetime
- 1996-01-31 HU HU9600218A patent/HU226121B1/hu not_active IP Right Cessation
- 1996-01-31 CA CA002168517A patent/CA2168517C/en not_active Expired - Fee Related
- 1996-01-31 NO NO19960411A patent/NO315160B1/no not_active IP Right Cessation
- 1996-01-31 BR BR9600290A patent/BR9600290A/pt not_active IP Right Cessation
- 1996-02-01 KR KR1019960002405A patent/KR100449192B1/ko not_active Expired - Fee Related
- 1996-02-01 SI SI9600033A patent/SI9600033B/sl not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20121129 |