DD228811A1 - Verfahren zur herstellung von neuen triazolopyrimidinen - Google Patents
Verfahren zur herstellung von neuen triazolopyrimidinen Download PDFInfo
- Publication number
- DD228811A1 DD228811A1 DD84262043A DD26204384A DD228811A1 DD 228811 A1 DD228811 A1 DD 228811A1 DD 84262043 A DD84262043 A DD 84262043A DD 26204384 A DD26204384 A DD 26204384A DD 228811 A1 DD228811 A1 DD 228811A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- chain length
- substituted
- alkyl group
- hydroxyethyl
- atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 hydroxypropyl group Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VORWEBDHEQSMJM-UHFFFAOYSA-N 2-[2-ethoxyethyl-(5-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound N=1C2=NC=NN2C(N(CCO)CCOCC)=CC=1N1CCCCC1 VORWEBDHEQSMJM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- LEYYLQKYOZYCRF-UHFFFAOYSA-N 1-(hexylamino)ethanol Chemical compound CCCCCCNC(C)O LEYYLQKYOZYCRF-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- KISUXSFXQRSZSR-UHFFFAOYSA-N 2-[butyl-(5-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound N=1C2=NC=NN2C(N(CCO)CCCC)=CC=1N1CCOCC1 KISUXSFXQRSZSR-UHFFFAOYSA-N 0.000 description 1
- CAUSJFJJYRCTPJ-UHFFFAOYSA-N 2-[hexyl-(5-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound N=1C2=NC=NN2C(N(CCO)CCCCCC)=CC=1N1CCCCC1 CAUSJFJJYRCTPJ-UHFFFAOYSA-N 0.000 description 1
- NKQANONWHOLZSH-UHFFFAOYSA-N 2-[pentyl-(2-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound N1(CCCCC1)C1=NN2C(N=CC=C2N(CCO)CCCCC)=N1 NKQANONWHOLZSH-UHFFFAOYSA-N 0.000 description 1
- LQKFTGMXROMIGG-UHFFFAOYSA-N 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=C(Cl)C=C(Cl)N2N=CN=C21 LQKFTGMXROMIGG-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002727 hyperosmolar Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003815 prostacyclins Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 229960000363 trapidil Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD84262043A DD228811A1 (de) | 1984-04-17 | 1984-04-17 | Verfahren zur herstellung von neuen triazolopyrimidinen |
| JP59235364A JPS60224692A (ja) | 1984-04-17 | 1984-11-09 | 新規なトリアゾロピリミジンおよびその製造法 |
| AT0105085A AT391866B (de) | 1984-04-17 | 1985-04-05 | Verfahren zur herstellung neuer s-triazolo (1,5-a) pyrimidine |
| DE3512629A DE3512629C2 (de) | 1984-04-17 | 1985-04-06 | s-Triazolo[1,5-a]pyrimidine und Verfahren zu ihrer Herstellung |
| SE8501835A SE466104B (sv) | 1984-04-17 | 1985-04-15 | Nya triazolpyrimidiner och foerfarande foer deras framstaellning |
| GB08509561A GB2157684B (en) | 1984-04-17 | 1985-04-15 | Triazolopyrimidines their preparation and use in medicine |
| CH1624/85A CH669196A5 (de) | 1984-04-17 | 1985-04-16 | Triazolopyrimidine und verfahren zu ihrer herstellung. |
| ES542269A ES8706682A1 (es) | 1984-04-17 | 1985-04-16 | Metodo para la fabricacion de nuevas triazolopirimidinas. |
| NL8501111A NL8501111A (nl) | 1984-04-17 | 1985-04-16 | Nieuwe triazolopyrimidine-verbindingen en werkwijze voor de bereiding daarvan. |
| SI8510641A SI8510641A (sl) | 1984-04-17 | 1985-04-16 | Novi triazolopirimidini in postopek za njihovo pridobivanje |
| SU853884102A SU1468423A3 (ru) | 1984-04-17 | 1985-04-16 | Способ получени 5-пиперидино-7- @ N-(н-пентил)-N-( @ -оксиэтил)-амино @ -S-триазоло (1,5- @ ) пиримидина |
| YU64185A YU47167B (sh) | 1984-04-17 | 1985-04-16 | Postupak za dobijanje novih s-triazolo(1,5-a)pirimidina |
| FR8505831A FR2562895B1 (fr) | 1984-04-17 | 1985-04-17 | Triazolopyridimidines nouvelles et procede pour leur fabrication |
| BE0/214861A BE902218A (fr) | 1984-04-17 | 1985-04-17 | Triazolopyrimidines, et leur procede de preparation. |
| CN 85103646 CN1013037B (zh) | 1984-04-17 | 1985-05-20 | 制造新型的三唑并嘧啶的方法 |
| BE0/215989A BE903828R (fr) | 1984-04-17 | 1985-12-10 | Triazolopyrimidines et leur procede de preparation. |
| LV930976A LV5512A3 (lv) | 1984-04-17 | 1993-06-30 | 5-Piperidino-7-ÚN-(n-pentil)-N-(beta-oksietil)-amino¾-S-triazol(1,5-a)pirimidina iegusanas panemeis |
| HR931017A HRP931017A2 (en) | 1984-04-17 | 1993-07-01 | New triazolopyrimidines and a process for their preparation |
| LTRP1203A LT2594B (lt) | 1984-04-17 | 1993-09-28 | 5-piperidino-7-(n-(n-peptil)-n-(beta-oksietil)-amino)-s-triazolo(1,5-a)pirimidino gavimo budas |
| MD94-0068A MD59C2 (ro) | 1984-04-17 | 1994-02-15 | Procedeu de obţinere a 5-piperidino-7-I N-(n-pentil)-N-(-oxietil)-aminoI-S-triazolo(1,5-a) pirimidinei |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD84262043A DD228811A1 (de) | 1984-04-17 | 1984-04-17 | Verfahren zur herstellung von neuen triazolopyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD228811A1 true DD228811A1 (de) | 1985-10-23 |
Family
ID=5556238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84262043A DD228811A1 (de) | 1984-04-17 | 1984-04-17 | Verfahren zur herstellung von neuen triazolopyrimidinen |
Country Status (15)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2149162C1 (ru) * | 1994-09-16 | 2000-05-20 | Ново Нордиск А/С | Производные [1,2,4] триазоло [4,3-а]хиноксалинона или их фармацевтически приемлемые соли, способ их получения, фармацевтическая композиция и способ ингибирования рецепторов амра |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| PT757984E (pt) * | 1995-08-08 | 2003-02-28 | Ono Pharmaceutical Co | Derivados de acido hidroxamico uteis para inibir a gelatinase |
| JP2001322933A (ja) | 2000-05-15 | 2001-11-20 | Ucb Sa | Ｃｄ４０シグナル遮断剤 |
| RU2401268C2 (ru) * | 2005-08-24 | 2010-10-10 | Пфайзер Инк. | КРИСТАЛЛИЧЕСКАЯ ФОРМА (R)-6-ЦИКЛОПЕНТИЛ-6-(2-(2,6-ДИЭТИЛПИРИДИН-4-ИЛ)ЭТИЛ)-3-((5,7-ДИМЕТИЛ-[1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИН-2-ИЛ)МЕТИЛ)-4-ГИДРОКСИ-5,6-ДИГИДРОПИРАН-2-ОНА, ЕЕ ПРИМЕНЕНИЕ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СОДЕРЖАЩАЯ ЕЕ |
| US8186931B2 (en) | 2006-08-17 | 2012-05-29 | Steven Borntrager | Powered hand truck |
| MD4246C1 (ro) * | 2012-03-12 | 2014-03-31 | Иван ПРИДА | Butoi pentru maturarea produselor alcoolice |
| AU2018237598B2 (en) | 2017-03-24 | 2023-12-14 | Piksci Inc. | Fused triazolo-pyrimidine compounds having useful pharmaceutical application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE61269C (de) * | 1891-04-01 | 1892-03-23 | J. NEWBURG in Berlin O., Am Schlesischen Bahnhof Nr. 5 | Waschmaschine |
| CH569734A5 (en) * | 1967-07-01 | 1975-11-28 | Hydrierwerk Rodleben Veb | 5-and 7-basically subst s-triazolo 1 5-a pyrimidines |
| DE1720004A1 (de) * | 1968-03-08 | 1971-05-19 | Hydrierwerk Rodleben Veb | Verfahren zur Herstellung von s-Triazolo(1.5-a)pyrimidinen,die in 5- und 7-Stellung durch basische Gruppen substituiert sind |
-
1984
- 1984-04-17 DD DD84262043A patent/DD228811A1/de not_active IP Right Cessation
- 1984-11-09 JP JP59235364A patent/JPS60224692A/ja active Granted
-
1985
- 1985-04-05 AT AT0105085A patent/AT391866B/de not_active IP Right Cessation
- 1985-04-06 DE DE3512629A patent/DE3512629C2/de not_active Expired - Fee Related
- 1985-04-15 GB GB08509561A patent/GB2157684B/en not_active Expired
- 1985-04-15 SE SE8501835A patent/SE466104B/sv not_active IP Right Cessation
- 1985-04-16 CH CH1624/85A patent/CH669196A5/de not_active IP Right Cessation
- 1985-04-16 ES ES542269A patent/ES8706682A1/es not_active Expired
- 1985-04-16 SU SU853884102A patent/SU1468423A3/ru active
- 1985-04-16 NL NL8501111A patent/NL8501111A/nl active Search and Examination
- 1985-04-16 YU YU64185A patent/YU47167B/sh unknown
- 1985-04-17 BE BE0/214861A patent/BE902218A/fr not_active IP Right Cessation
- 1985-04-17 FR FR8505831A patent/FR2562895B1/fr not_active Expired
- 1985-12-10 BE BE0/215989A patent/BE903828R/fr not_active IP Right Cessation
-
1993
- 1993-09-28 LT LTRP1203A patent/LT2594B/xx not_active IP Right Cessation
-
1994
- 1994-02-15 MD MD94-0068A patent/MD59C2/ro not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE466104B (sv) | 1991-12-16 |
| GB8509561D0 (en) | 1985-05-22 |
| SE8501835D0 (sv) | 1985-04-15 |
| BE903828R (fr) | 1986-04-01 |
| DE3512629A1 (de) | 1986-10-09 |
| JPS60224692A (ja) | 1985-11-09 |
| DE3512629C2 (de) | 1995-07-06 |
| SE8501835L (sv) | 1985-10-18 |
| FR2562895B1 (fr) | 1988-10-07 |
| JPH0455193B2 (enrdf_load_stackoverflow) | 1992-09-02 |
| YU47167B (sh) | 1995-01-31 |
| MD59B1 (ro) | 1994-08-31 |
| ES8706682A1 (es) | 1987-07-01 |
| GB2157684A (en) | 1985-10-30 |
| YU64185A (sh) | 1992-09-07 |
| FR2562895A1 (fr) | 1985-10-18 |
| MD59C2 (ro) | 1995-01-31 |
| ATA105085A (de) | 1990-06-15 |
| AT391866B (de) | 1990-12-10 |
| LT2594B (lt) | 1994-03-25 |
| CH669196A5 (de) | 1989-02-28 |
| BE902218A (fr) | 1985-08-16 |
| ES542269A0 (es) | 1987-07-01 |
| NL8501111A (nl) | 1985-11-18 |
| GB2157684B (en) | 1987-11-11 |
| SU1468423A3 (ru) | 1989-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RPI | Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act) | ||
| RPV | Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |