DE2614738C2 - Diuretisch wirkende Arzneimittel - Google Patents
Diuretisch wirkende ArzneimittelInfo
- Publication number
- DE2614738C2 DE2614738C2 DE2614738A DE2614738A DE2614738C2 DE 2614738 C2 DE2614738 C2 DE 2614738C2 DE 2614738 A DE2614738 A DE 2614738A DE 2614738 A DE2614738 A DE 2614738A DE 2614738 C2 DE2614738 C2 DE 2614738C2
- Authority
- DE
- Germany
- Prior art keywords
- triamterene
- sulfuric acid
- triamino
- pteridine
- hydroxyphenyl
- 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
- 230000001882 diuretic effect Effects 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims 6
- 229940079593 drug Drugs 0.000 title claims 4
- 239000002934 diuretic Substances 0.000 title claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 36
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims description 31
- 229960001288 triamterene Drugs 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 19
- QNJVMSASTUDLGC-UHFFFAOYSA-N 4-(2,4,7-triaminopteridin-6-yl)phenol Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=C(O)C=C1 QNJVMSASTUDLGC-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 230000032258 transport Effects 0.000 claims description 8
- 208000004880 Polyuria Diseases 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- 230000028327 secretion Effects 0.000 claims description 6
- -1 sulfuric acid ester Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 230000010412 perfusion Effects 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 230000008033 biological extinction Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims description 2
- 230000009103 reabsorption Effects 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000001447 alkali salts Chemical class 0.000 claims 3
- 239000002207 metabolite Substances 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 210000004907 gland Anatomy 0.000 claims 2
- 239000002808 molecular sieve Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 2
- 208000000913 Kidney Calculi Diseases 0.000 claims 1
- 206010029148 Nephrolithiasis Diseases 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 230000009471 action Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 210000001038 distal kidney tubule Anatomy 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- 210000000981 epithelium Anatomy 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 230000004941 influx Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 238000000691 measurement method Methods 0.000 claims 1
- 230000010534 mechanism of action Effects 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- 239000003286 potassium sparing diuretic agent Substances 0.000 claims 1
- 229940097241 potassium-sparing diuretic Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 210000003079 salivary gland Anatomy 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000011734 sodium Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000003804 effect on potassium Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 210000001581 salivary duct Anatomy 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (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)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2614738A DE2614738C2 (de) | 1976-04-06 | 1976-04-06 | Diuretisch wirkende Arzneimittel |
| FR7709307A FR2347043A1 (fr) | 1976-04-06 | 1977-03-29 | Medicament diuretique |
| US05/783,386 US4118492A (en) | 1976-04-06 | 1977-03-31 | Diuretic pharmaceutical compositions and method of use containing the sulfuric acid half-ester of 2,4,7-triamino-6p-hydroxyphenyl pteridine |
| GB13747/77A GB1582014A (en) | 1976-04-06 | 1977-03-31 | Pteridine compounds |
| JP3938477A JPS52122618A (en) | 1976-04-06 | 1977-04-06 | Hydragogue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2614738A DE2614738C2 (de) | 1976-04-06 | 1976-04-06 | Diuretisch wirkende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2614738A1 DE2614738A1 (de) | 1977-10-27 |
| DE2614738C2 true DE2614738C2 (de) | 1985-01-31 |
Family
ID=5974527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2614738A Expired DE2614738C2 (de) | 1976-04-06 | 1976-04-06 | Diuretisch wirkende Arzneimittel |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4118492A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS52122618A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2614738C2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2347043A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1582014A (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252809A (en) * | 1977-01-03 | 1981-02-24 | Rohm Pharma Gmbh | Substituted pteridine compounds and pharmaceutical compositions containing the same |
| DE2815442A1 (de) | 1978-04-10 | 1979-10-18 | Roehm Pharma Gmbh | Rasch wirksame diuretika |
| US4425346A (en) | 1980-08-01 | 1984-01-10 | Smith And Nephew Associated Companies Limited | Pharmaceutical compositions |
| DE3448490C2 (de) * | 1984-04-05 | 1995-04-27 | Roehm Pharma Gmbh | Verwendung von Pteridinderivaten zur Behandlung von Herzarrhythmien |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3081230A (en) * | 1960-09-08 | 1963-03-12 | Smith Kline French Lab | Diuretic and antihypertensive triaminoarylpteridines |
-
1976
- 1976-04-06 DE DE2614738A patent/DE2614738C2/de not_active Expired
-
1977
- 1977-03-29 FR FR7709307A patent/FR2347043A1/fr active Granted
- 1977-03-31 US US05/783,386 patent/US4118492A/en not_active Expired - Lifetime
- 1977-03-31 GB GB13747/77A patent/GB1582014A/en not_active Expired
- 1977-04-06 JP JP3938477A patent/JPS52122618A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52122618A (en) | 1977-10-15 |
| FR2347043B1 (cg-RX-API-DMAC7.html) | 1979-03-02 |
| US4118492A (en) | 1978-10-03 |
| FR2347043A1 (fr) | 1977-11-04 |
| GB1582014A (en) | 1980-12-31 |
| DE2614738A1 (de) | 1977-10-27 |
| JPS6143329B2 (cg-RX-API-DMAC7.html) | 1986-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |