SE436203B - Analogiforfarande for framstellning av 6-(substituerad fenyl)-2,4,7-triamino-pteridiner - Google Patents
Analogiforfarande for framstellning av 6-(substituerad fenyl)-2,4,7-triamino-pteridinerInfo
- Publication number
- SE436203B SE436203B SE7800048A SE7800048A SE436203B SE 436203 B SE436203 B SE 436203B SE 7800048 A SE7800048 A SE 7800048A SE 7800048 A SE7800048 A SE 7800048A SE 436203 B SE436203 B SE 436203B
- Authority
- SE
- Sweden
- Prior art keywords
- triamino
- pteridine
- hydrogen
- phenyl
- prepared
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 chloro-substituted phenyl Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 230000001882 diuretic effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 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 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- LNMQRZRWVQDPIB-UHFFFAOYSA-N [4-(2,4,7-triaminopteridin-6-yl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N LNMQRZRWVQDPIB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- IUHCATHBKLBCRH-UHFFFAOYSA-N 3-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]propane-1,2-diol Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=C(OCC(O)CO)C=C1 IUHCATHBKLBCRH-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- RFBACHVOZKQPJR-UHFFFAOYSA-N 2-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]ethanol Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=C(OCCO)C=C1 RFBACHVOZKQPJR-UHFFFAOYSA-N 0.000 claims 1
- XXFIGLAYTZCDPY-UHFFFAOYSA-N 6-(4-methoxyphenyl)pteridine-2,4,7-triamine Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N XXFIGLAYTZCDPY-UHFFFAOYSA-N 0.000 claims 1
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- 238000005917 acylation reaction Methods 0.000 claims 1
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- 239000002244 precipitate Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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- 229960001288 triamterene Drugs 0.000 description 10
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- ZVEKWQJEZUFXHU-UHFFFAOYSA-N [4-(cyanomethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(CC#N)C=C1 ZVEKWQJEZUFXHU-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000002340 alkalosis Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960002576 amiloride Drugs 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 150000007962 benzene acetonitriles Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- DXYNDDQQWQTPJH-UHFFFAOYSA-N butan-2-one;propan-2-one;hydrate Chemical compound O.CC(C)=O.CCC(C)=O DXYNDDQQWQTPJH-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 210000001038 distal kidney tubule Anatomy 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000000705 hypocalcaemia Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 238000011294 monotherapeutic Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HXJMTEWBOIGJHZ-UHFFFAOYSA-N propyl [4-(2,4,7-triaminopteridin-6-yl)phenyl] carbonate Chemical compound C1=CC(OC(=O)OCCC)=CC=C1C1=NC2=C(N)N=C(N)N=C2N=C1N HXJMTEWBOIGJHZ-UHFFFAOYSA-N 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012113 quantitative test Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000001913 submandibular gland Anatomy 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 1
- 210000005239 tubule Anatomy 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Springs (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772700073 DE2700073A1 (de) | 1977-01-03 | 1977-01-03 | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7800048L SE7800048L (sv) | 1978-07-04 |
| SE436203B true SE436203B (sv) | 1984-11-19 |
Family
ID=5998070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7800048A SE436203B (sv) | 1977-01-03 | 1978-01-02 | Analogiforfarande for framstellning av 6-(substituerad fenyl)-2,4,7-triamino-pteridiner |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5384993A (en, 2012) |
| AT (1) | AT353798B (en, 2012) |
| AU (1) | AU515140B2 (en, 2012) |
| CA (1) | CA1099714A (en, 2012) |
| CH (2) | CH633962A5 (en, 2012) |
| DD (1) | DD136837A5 (en, 2012) |
| DE (1) | DE2700073A1 (en, 2012) |
| ES (1) | ES465578A1 (en, 2012) |
| FR (2) | FR2420345B1 (en, 2012) |
| GB (2) | GB1597882A (en, 2012) |
| NL (1) | NL190573C (en, 2012) |
| SE (1) | SE436203B (en, 2012) |
| ZA (1) | ZA7812B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815442A1 (de) * | 1978-04-10 | 1979-10-18 | Roehm Pharma Gmbh | Rasch wirksame diuretika |
| DE3407695A1 (de) * | 1984-03-02 | 1985-09-12 | Röhm Pharma GmbH, 6108 Weiterstadt | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
| DE3505253C2 (de) * | 1985-02-15 | 1995-04-27 | Seitz Enzinger Noll Masch | Flaschenverteilstation zum Umformen eines angeförderten einspurigen Flaschenstroms zu einem abzufördernden breiten Flaschenstrom |
| HU214331B (hu) * | 1992-06-17 | 1998-03-02 | Gyógyszerkutató Intézet Kft. | Eljárás piperazin- és homopiperazinszármazékok és ezeket tartalmazó gyógyszerkészítmények előállítására |
| CN118019482A (zh) | 2021-09-28 | 2024-05-10 | 安布股份有限公司 | 内窥镜 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3081230A (en) | 1960-09-08 | 1963-03-12 | Smith Kline French Lab | Diuretic and antihypertensive triaminoarylpteridines |
| FR1014M (fr) * | 1960-11-05 | 1961-12-26 | Smith Kline French Lab | Compositions médicinales a base de 6-aryl-2,4,7-triaminoptéridine. |
-
1977
- 1977-01-03 DE DE19772700073 patent/DE2700073A1/de active Granted
- 1977-10-20 AT AT748877A patent/AT353798B/de not_active IP Right Cessation
- 1977-12-28 JP JP15864777A patent/JPS5384993A/ja active Granted
- 1977-12-29 DD DD77203010A patent/DD136837A5/xx unknown
- 1977-12-29 ES ES465578A patent/ES465578A1/es not_active Expired
- 1977-12-30 FR FR7739798A patent/FR2420345B1/fr not_active Expired
-
1978
- 1978-01-01 CH CH1359977A patent/CH633962A5/de not_active IP Right Cessation
- 1978-01-02 SE SE7800048A patent/SE436203B/sv not_active IP Right Cessation
- 1978-01-03 GB GB26630/80A patent/GB1597882A/en not_active Expired
- 1978-01-03 ZA ZA00780012A patent/ZA7812B/xx unknown
- 1978-01-03 NL NL7800067A patent/NL190573C/xx not_active IP Right Cessation
- 1978-01-03 AU AU32140/78A patent/AU515140B2/en not_active Expired
- 1978-01-03 GB GB67/78A patent/GB1597881A/en not_active Expired
- 1978-01-03 CA CA294,246A patent/CA1099714A/en not_active Expired
-
1980
- 1980-02-14 FR FR8003308A patent/FR2445331A1/fr active Granted
-
1982
- 1982-09-06 CH CH528882A patent/CH639663A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7800067A (nl) | 1978-07-05 |
| FR2420345A1 (en, 2012) | 1979-10-19 |
| GB1597882A (en) | 1981-09-16 |
| GB1597881A (en) | 1981-09-16 |
| DE2700073C2 (en, 2012) | 1991-03-21 |
| ES465578A1 (es) | 1979-01-01 |
| JPS5384993A (en) | 1978-07-26 |
| CH633962A5 (en) | 1983-01-14 |
| ATA748877A (de) | 1979-05-15 |
| ZA7812B (en) | 1978-10-25 |
| FR2420345B1 (en, 2012) | 1983-01-28 |
| NL190573B (nl) | 1993-12-01 |
| JPS631314B2 (en, 2012) | 1988-01-12 |
| AU515140B2 (en) | 1981-03-19 |
| CH639663A5 (en) | 1983-11-30 |
| CA1099714A (en) | 1981-04-21 |
| AT353798B (de) | 1979-12-10 |
| FR2445331A1 (fr) | 1980-07-25 |
| FR2445331B1 (en, 2012) | 1983-01-28 |
| SE7800048L (sv) | 1978-07-04 |
| DD136837A5 (de) | 1979-08-01 |
| AU3214078A (en) | 1979-07-12 |
| DE2700073A1 (de) | 1978-07-13 |
| NL190573C (nl) | 1994-05-02 |
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