UA86883C2 - Пара-метоксианилиды 4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоновых кислот, которые проявляют диуретическую активность - Google Patents
Пара-метоксианилиды 4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоновых кислот, которые проявляют диуретическую активность Download PDFInfo
- Publication number
- UA86883C2 UA86883C2 UAA200711723A UAA200711723A UA86883C2 UA 86883 C2 UA86883 C2 UA 86883C2 UA A200711723 A UAA200711723 A UA A200711723A UA A200711723 A UAA200711723 A UA A200711723A UA 86883 C2 UA86883 C2 UA 86883C2
- Authority
- UA
- Ukraine
- Prior art keywords
- hydroxy
- para
- oxo
- dihydroquinoline
- compounds
- Prior art date
Links
- 230000001882 diuretic effect Effects 0.000 title claims abstract description 13
- JEBJIWLJHQOTIA-UHFFFAOYSA-N 2-hydroxy-4-quinolone-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=C(O)C2=C1 JEBJIWLJHQOTIA-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000001747 exhibiting effect Effects 0.000 title abstract 2
- 239000000126 substance Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 17
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000002934 diuretic Substances 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 8
- 229940030606 diuretics Drugs 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 210000002700 urine Anatomy 0.000 claims description 3
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- 230000002077 kaliuretic effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 230000007721 medicinal effect Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 229910001414 potassium ion Inorganic materials 0.000 claims 1
- -1 sodium tetraphenylborate Chemical compound 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 231100000167 toxic agent Toxicity 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000000975 bioactive effect Effects 0.000 abstract 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- NDCFBPDNHOZORS-UHFFFAOYSA-N 1,2-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2NCC(C(=O)O)=CC2=C1 NDCFBPDNHOZORS-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 241000208202 Linaceae Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 206010006440 Bronchial obstruction Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000019025 Hypokalemia Diseases 0.000 description 1
- 208000032912 Local swelling Diseases 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030124 Oedema peripheral Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000269799 Perca fluviatilis Species 0.000 description 1
- 241000514450 Podocarpus latifolius Species 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 241000159610 Roya <green alga> Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 201000010064 diabetes insipidus Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 208000024896 potassium deficiency disease Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Изобретение относится к химико-фармацевтической промышленности и касается биологически активных веществ, в частности производных хинолин-3-карбоновой кислоты, общей формулы І: EMBED ISISServer , где R = -СН2СН2СООН, R' = Н, или R = Ph, R' = H, или R = Н, R' = 6-Сl, или R'+R = 8-СН2СН2-, которые проявляют высокую диуретическую активность.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| UAA200711723A UA86883C2 (ru) | 2007-10-23 | 2007-10-23 | Пара-метоксианилиды 4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоновых кислот, которые проявляют диуретическую активность |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| UAA200711723A UA86883C2 (ru) | 2007-10-23 | 2007-10-23 | Пара-метоксианилиды 4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоновых кислот, которые проявляют диуретическую активность |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA86883C2 true UA86883C2 (ru) | 2009-05-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200711723A UA86883C2 (ru) | 2007-10-23 | 2007-10-23 | Пара-метоксианилиды 4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоновых кислот, которые проявляют диуретическую активность |
Country Status (1)
| Country | Link |
|---|---|
| UA (1) | UA86883C2 (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2480468C1 (ru) * | 2012-02-16 | 2013-04-27 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | КРИСТАЛЛИЧЕСКАЯ МОДИФИКАЦИЯ ПАРА-МЕТОКСИАНИЛИДА 6-ГИДРОКСИ-4-ОКСО-2,4-ДИГИДРО-1Н-ПИРРОЛО[3,2,1-ij]ХИНОЛИН-5-КАРБОНОВОЙ КИСЛОТЫ |
-
2007
- 2007-10-23 UA UAA200711723A patent/UA86883C2/ru unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2480468C1 (ru) * | 2012-02-16 | 2013-04-27 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | КРИСТАЛЛИЧЕСКАЯ МОДИФИКАЦИЯ ПАРА-МЕТОКСИАНИЛИДА 6-ГИДРОКСИ-4-ОКСО-2,4-ДИГИДРО-1Н-ПИРРОЛО[3,2,1-ij]ХИНОЛИН-5-КАРБОНОВОЙ КИСЛОТЫ |
| WO2013122509A1 (ru) * | 2012-02-16 | 2013-08-22 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | Кристаллическая модификация пара-метоксианилида 6-гидрокси-4-оксо-2,4-дигидро-1н-пирроло[3,2,1-ijхинолин-5-карбоновой кислоты |
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