GEP19970835B - Process for obtaining 3-(methyltio, methylsulphinyl or methylsulphonyl)-4-quinolone - Google Patents
Process for obtaining 3-(methyltio, methylsulphinyl or methylsulphonyl)-4-quinoloneInfo
- Publication number
- GEP19970835B GEP19970835B GEAP19942162A GEAP1994002162A GEP19970835B GE P19970835 B GEP19970835 B GE P19970835B GE AP19942162 A GEAP19942162 A GE AP19942162A GE AP1994002162 A GEAP1994002162 A GE AP1994002162A GE P19970835 B GEP19970835 B GE P19970835B
- Authority
- GE
- Georgia
- Prior art keywords
- lower alkyl
- sulphonamide
- dihydroquinoline
- oxo
- quinolones
- Prior art date
Links
- -1 methylsulphinyl Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000007660 quinolones Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- CKMRUFDOPVYNHH-UHFFFAOYSA-N 1-methyl-4-oxoquinoline-3-sulfonamide Chemical compound C1=CC=C2N(C)C=C(S(N)(=O)=O)C(=O)C2=C1 CKMRUFDOPVYNHH-UHFFFAOYSA-N 0.000 abstract 1
- XZMQFGBEPTUAQS-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-4-oxoquinoline-3-sulfonamide Chemical compound CN1C=C(S(N)(=O)=O)C(=O)C2=C1C=C(OC)C(OC)=C2 XZMQFGBEPTUAQS-UHFFFAOYSA-N 0.000 abstract 1
- 206010019280 Heart failures Diseases 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 208000031225 myocardial ischemia Diseases 0.000 abstract 1
- UMBKNZYONDDZAF-UHFFFAOYSA-N n,1-dimethyl-4-oxoquinoline-3-sulfonamide Chemical compound C1=CC=C2C(=O)C(S(=O)(=O)NC)=CN(C)C2=C1 UMBKNZYONDDZAF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D215/36—Sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Quinolones with antihypertensive activity have the general formula I, I wherein X is the residue of an optionally substituted benzene ring; R is lower alkyl; R3 is hydrogen or lower alkyl; R1 and R2, which may be the same or different, are hydrogen, lower alkyl, or, together with the nitrogen atom to which they are attached, form a 5 to 7 membered saturated heterocyclic ring optionally containing an additional hetero atom selected from nitrogen, oxygen and sulphur and optionally substituted by 1 or more lower alkyl groups; and the dotted line between positions 2 and 3 of the quinolone nucleus represents an optional bond. The compounds are useful as antihypertensive agents. They are also indicated for use in treating heart failure and ischaemic heart disease. With the exception of the three compounds 1-methyl-4-oxo-1,4-dihydroquinoline-3-sulphonamide, 1,N-dimethyl-4-oxo-1,4-dihydroquinoline-3-sulphonamide and 6,7-dimethoxyl-methyl-4-oxo-1,4-dihydroquinoline-3-sulphonamide, the quinolones of formula I are novel. Pharmaceutical compositions containing the compounds of formula I are described. Processes for preparing the novel quinolones are also described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910558 | 1979-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GEP19970835B true GEP19970835B (en) | 1997-02-10 |
Family
ID=10504143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GEAP19942162A GEP19970835B (en) | 1979-03-27 | 1994-09-07 | Process for obtaining 3-(methyltio, methylsulphinyl or methylsulphonyl)-4-quinolone |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS55130960A (en) |
| BE (1) | BE882443A (en) |
| CY (1) | CY1343A (en) |
| ES (1) | ES8104232A1 (en) |
| GB (1) | GB2047691B (en) |
| GE (1) | GEP19970835B (en) |
| JO (1) | JO1072B1 (en) |
| MX (1) | MX5950A (en) |
| SU (1) | SU1124886A3 (en) |
| ZA (1) | ZA801575B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
| IE51542B1 (en) * | 1980-09-26 | 1987-01-07 | Boots Co Ltd | Therapeutic agents |
| DE68917024D1 (en) * | 1988-05-24 | 1994-09-01 | Kirin Brewery | 4 (1H) quinolone derivatives. |
| US8697674B2 (en) | 2004-12-29 | 2014-04-15 | Naturon, Inc. | Xanthurenic acid derivative pharmaceutical compositions and methods related thereto |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
-
1980
- 1980-03-18 ZA ZA00801575A patent/ZA801575B/en unknown
- 1980-03-25 GB GB8010075A patent/GB2047691B/en not_active Expired
- 1980-03-25 CY CY1343A patent/CY1343A/en unknown
- 1980-03-26 BE BE0/199956A patent/BE882443A/en not_active IP Right Cessation
- 1980-03-26 JO JO19801072A patent/JO1072B1/en active
- 1980-03-26 ES ES489929A patent/ES8104232A1/en not_active Expired
- 1980-03-27 JP JP3961080A patent/JPS55130960A/en active Granted
-
1981
- 1981-01-19 SU SU802897803A patent/SU1124886A3/en active
-
1985
- 1985-01-09 MX MX595085A patent/MX5950A/en unknown
-
1986
- 1986-12-24 JP JP61316048A patent/JPS62215526A/en active Granted
-
1994
- 1994-09-07 GE GEAP19942162A patent/GEP19970835B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE882443A (en) | 1980-09-26 |
| JPS62215526A (en) | 1987-09-22 |
| CY1343A (en) | 1987-01-16 |
| JPH0114224B2 (en) | 1989-03-10 |
| ES489929A0 (en) | 1981-04-16 |
| ES8104232A1 (en) | 1981-04-16 |
| JO1072B1 (en) | 1982-07-10 |
| JPS55130960A (en) | 1980-10-11 |
| GB2047691A (en) | 1980-12-03 |
| GB2047691B (en) | 1983-07-20 |
| SU1124886A3 (en) | 1984-11-15 |
| MX5950A (en) | 1993-11-01 |
| ZA801575B (en) | 1981-03-25 |
| JPH0250086B2 (en) | 1990-11-01 |
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