ES459976A1 - Esters of nitroxoline with (poly)carboxylic or (poly)sulphonic acids - useful as antibacterials and antifungals - Google Patents
Esters of nitroxoline with (poly)carboxylic or (poly)sulphonic acids - useful as antibacterials and antifungalsInfo
- Publication number
- ES459976A1 ES459976A1 ES459976A ES459976A ES459976A1 ES 459976 A1 ES459976 A1 ES 459976A1 ES 459976 A ES459976 A ES 459976A ES 459976 A ES459976 A ES 459976A ES 459976 A1 ES459976 A1 ES 459976A1
- Authority
- ES
- Spain
- Prior art keywords
- poly
- nitroxoline
- antifungals
- carboxylic
- esters
- 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
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 title abstract 5
- 239000002253 acid Substances 0.000 title abstract 3
- 229960005131 nitroxoline Drugs 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 229940121375 antifungal agent Drugs 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- -1 5-nitroquinolin-8-yl Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 241000700159 Rattus Species 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Esters of nitroxoline with mono- or poly-carboxylic or sulphonic acids, esp. of formula (I), are new cpds. (where X is CO or SO2 R is =17C opt. unsatd., (branched) hydrocarbyl, aryl or aralkyl in which each phenyl ring can be substd. by >=1.1-4C alkyl, F, Cl, Br, NO2 or CN, a gp.-AXOY, or adamantyl A is 2-20C opt. unsatd. hydrocarbyl Y is H, 1-4C alkyl or 5-nitroquinolin-8-yl). (I) are prepd. by reacting nitroxoline (II) with the appropriate acid or its deriv. (I) are useful antibacterials and antifungals at least as effective as (II) but with a longer-lasting effect and better oil solubility. Toxicity is low e.g. the LDo=>=1.1g/kg orally in rats. Specific cpd. is 5-nitroquinolin-8-yl undecylinate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2639176 | 1976-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES459976A1 true ES459976A1 (en) | 1978-05-01 |
Family
ID=10242908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES459976A Expired ES459976A1 (en) | 1976-06-24 | 1977-06-21 | Esters of nitroxoline with (poly)carboxylic or (poly)sulphonic acids - useful as antibacterials and antifungals |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE855851A (en) |
| DE (1) | DE2728248A1 (en) |
| ES (1) | ES459976A1 (en) |
| FR (1) | FR2355829A1 (en) |
| ZA (1) | ZA773797B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001524468A (en) * | 1997-11-21 | 2001-12-04 | エヌピーエス ファーマシューティカルズ インコーポレーテッド | Metabotropic glutamate receptor antagonists for treating central nervous system disorders |
| US6429207B1 (en) | 1997-11-21 | 2002-08-06 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| AU2019351494B2 (en) * | 2018-09-29 | 2025-03-13 | Jiangsu Yahong Meditech Co., Ltd. | Nitroxoline prodrug and use thereof |
| TWI874355B (en) * | 2020-02-14 | 2025-03-01 | 中國大陸商江蘇亞虹醫藥科技股份有限公司 | Prodrug of nitroxoline and use thereof |
| CN111514142B (en) * | 2020-05-29 | 2021-04-06 | 江苏亚虹医药科技股份有限公司 | Pharmaceutical composition containing nitroxoline prodrug and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2237903A1 (en) * | 1972-08-02 | 1974-03-28 | Basf Ag | 8-Acyloxyquinoline derivs prepn - with antibacterial and antifungal activity |
-
1977
- 1977-06-07 FR FR7717431A patent/FR2355829A1/en not_active Withdrawn
- 1977-06-20 BE BE2056010A patent/BE855851A/en unknown
- 1977-06-21 ES ES459976A patent/ES459976A1/en not_active Expired
- 1977-06-23 DE DE19772728248 patent/DE2728248A1/en active Pending
- 1977-06-24 ZA ZA00773797A patent/ZA773797B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE855851A (en) | 1977-12-20 |
| ZA773797B (en) | 1978-05-30 |
| FR2355829A1 (en) | 1978-01-20 |
| DE2728248A1 (en) | 1978-01-05 |
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