CS51592A3 - 1,2,4-triazolo(1,5-a)pyrimidine derivatives - Google Patents
1,2,4-triazolo(1,5-a)pyrimidine derivatives Download PDFInfo
- Publication number
- CS51592A3 CS51592A3 CS92515A CS51592A CS51592A3 CS 51592 A3 CS51592 A3 CS 51592A3 CS 92515 A CS92515 A CS 92515A CS 51592 A CS51592 A CS 51592A CS 51592 A3 CS51592 A3 CS 51592A3
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- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- carbon atoms
- triazolo
- mol
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- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 title description 2
- -1 hydroxy, carboxy, amino, morpholinocarbonyl Chemical group 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 202
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 69
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- 230000003257 anti-anginal effect Effects 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000009090 positive inotropic effect Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 241001674048 Phthiraptera Species 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
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- 230000008025 crystallization Effects 0.000 description 87
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- 239000000243 solution Substances 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 40
- 239000000203 mixture Substances 0.000 description 37
- 239000013078 crystal Substances 0.000 description 34
- 238000010992 reflux Methods 0.000 description 32
- 238000001816 cooling Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 22
- 238000012360 testing method Methods 0.000 description 21
- 239000000725 suspension Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
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- 241001465754 Metazoa Species 0.000 description 11
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
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- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 150000003573 thiols Chemical class 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU91587A HU208693B (en) | 1991-02-22 | 1991-02-22 | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS51592A3 true CS51592A3 (en) | 1992-10-14 |
Family
ID=10950293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS92515A CS51592A3 (en) | 1991-02-22 | 1992-02-21 | 1,2,4-triazolo(1,5-a)pyrimidine derivatives |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0500136B1 (de) |
| JP (1) | JPH05148267A (de) |
| KR (1) | KR920016456A (de) |
| CN (1) | CN1033585C (de) |
| AT (1) | ATE138067T1 (de) |
| AU (1) | AU642073B2 (de) |
| CA (1) | CA2061629A1 (de) |
| CS (1) | CS51592A3 (de) |
| DE (1) | DE69210647T2 (de) |
| ES (1) | ES2089258T3 (de) |
| FI (1) | FI100401B (de) |
| GB (1) | GB2254611B (de) |
| HU (1) | HU208693B (de) |
| IL (1) | IL101033A (de) |
| PL (1) | PL170050B1 (de) |
| RU (1) | RU2097382C1 (de) |
| TW (1) | TW213462B (de) |
| YU (1) | YU17592A (de) |
| ZA (1) | ZA921269B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW224044B (de) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| TW258648B (de) * | 1993-03-04 | 1995-10-01 | Shell Internat Res Schappej Bv | |
| EP0628559B1 (de) * | 1993-06-10 | 2002-04-03 | Beiersdorf-Lilly GmbH | Pyrimidinverbindungen und ihre Verwendung als Pharmazeutika |
| US5571813A (en) * | 1993-06-10 | 1996-11-05 | Beiersdorf-Lilly Gmbh | Fused pyrimidine compounds and their use as pharmaceuticals |
| US8508469B1 (en) | 1995-12-01 | 2013-08-13 | Immersion Corporation | Networked applications including haptic feedback |
| US6448253B1 (en) * | 1998-09-16 | 2002-09-10 | King Pharmaceuticals Research And Development, Inc. | Adenosine A3 receptor modulators |
| US6514989B1 (en) * | 2001-07-20 | 2003-02-04 | Hoffmann-La Roche Inc. | Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives |
| WO2003030904A1 (en) * | 2001-10-08 | 2003-04-17 | F. Hoffmann-La Roche Ag | 8-amino-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide |
| CA2542290A1 (en) * | 2003-10-17 | 2005-04-28 | Nippon Kayaku Kabushiki Kaisha | Substituted 2-amino-[1,2,4]triazolo[1,5-a]pyrimidine derivative and use thereof |
| RU2378278C2 (ru) * | 2008-01-24 | 2010-01-10 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |
| CA2775354C (en) | 2009-09-29 | 2019-01-15 | Margaret Phillips | Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase |
| MA50375A (fr) * | 2014-04-23 | 2021-05-26 | Dart Neuroscience Cayman Ltd | Compositions contenant des composés substitués de [1,2,4]triazolo[1,5-a]pyrimidine-7-yl utilisés en tant qu'inhibiteurs pde2 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1792811C2 (de) * | 1966-10-03 | 1982-12-30 | VEB Deutsches Hydrierwerk Rodleben, DDR 4530 Roßlau | "Arzneimittel mit koronargefäßerweiternder Wirkung" |
| DE2327133A1 (de) * | 1972-06-07 | 1974-01-03 | Icn Pharmaceuticals | 2-subst.-thio-s-triazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine |
| US4497814A (en) * | 1982-08-16 | 1985-02-05 | Schering Corporation | 2-(Pyridinyl)-1,2,4-triazolo[1,5-a]pyrimidines and derivatives useful in increasing cardiac contractility |
| DD280111A1 (de) * | 1986-01-09 | 1990-06-27 | Hydrierwerk Rodleben Veb | Verfahren zur herstellung neuer triazolo-pyrimidine |
-
1991
- 1991-02-22 HU HU91587A patent/HU208693B/hu not_active IP Right Cessation
-
1992
- 1992-02-21 FI FI920776A patent/FI100401B/fi active
- 1992-02-21 CS CS92515A patent/CS51592A3/cs unknown
- 1992-02-21 PL PL92293564A patent/PL170050B1/pl unknown
- 1992-02-21 RU SU925011062A patent/RU2097382C1/ru active
- 1992-02-21 KR KR1019920002616A patent/KR920016456A/ko not_active Abandoned
- 1992-02-21 YU YU17592A patent/YU17592A/sh unknown
- 1992-02-21 ZA ZA921269A patent/ZA921269B/xx unknown
- 1992-02-21 CA CA002061629A patent/CA2061629A1/en not_active Abandoned
- 1992-02-21 JP JP4070092A patent/JPH05148267A/ja active Pending
- 1992-02-21 GB GB9203736A patent/GB2254611B/en not_active Expired - Fee Related
- 1992-02-21 AU AU11175/92A patent/AU642073B2/en not_active Ceased
- 1992-02-21 IL IL10103392A patent/IL101033A/en not_active IP Right Cessation
- 1992-02-22 CN CN92101158A patent/CN1033585C/zh not_active Expired - Fee Related
- 1992-02-24 EP EP92102981A patent/EP0500136B1/de not_active Expired - Lifetime
- 1992-02-24 DE DE69210647T patent/DE69210647T2/de not_active Expired - Fee Related
- 1992-02-24 AT AT92102981T patent/ATE138067T1/de not_active IP Right Cessation
- 1992-02-24 ES ES92102981T patent/ES2089258T3/es not_active Expired - Lifetime
- 1992-04-09 TW TW081102762A patent/TW213462B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| YU17592A (sh) | 1995-03-27 |
| GB2254611A (en) | 1992-10-14 |
| AU1117592A (en) | 1992-08-27 |
| PL293564A1 (en) | 1992-11-02 |
| IL101033A (en) | 1996-07-23 |
| FI920776A0 (fi) | 1992-02-21 |
| FI920776A7 (fi) | 1992-08-23 |
| KR920016456A (ko) | 1992-09-24 |
| PL170050B1 (pl) | 1996-10-31 |
| ES2089258T3 (es) | 1996-10-01 |
| CN1033585C (zh) | 1996-12-18 |
| HU208693B (en) | 1993-12-28 |
| ATE138067T1 (de) | 1996-06-15 |
| CN1064277A (zh) | 1992-09-09 |
| FI100401B (fi) | 1997-11-28 |
| ZA921269B (en) | 1993-08-26 |
| HU910587D0 (en) | 1991-09-30 |
| GB2254611B (en) | 1995-04-26 |
| DE69210647T2 (de) | 1997-01-09 |
| IL101033A0 (en) | 1992-11-15 |
| EP0500136B1 (de) | 1996-05-15 |
| DE69210647D1 (de) | 1996-06-20 |
| HUT61308A (en) | 1992-12-28 |
| EP0500136A1 (de) | 1992-08-26 |
| RU2097382C1 (ru) | 1997-11-27 |
| TW213462B (de) | 1993-09-21 |
| AU642073B2 (en) | 1993-10-07 |
| GB9203736D0 (en) | 1992-04-08 |
| CA2061629A1 (en) | 1992-08-23 |
| JPH05148267A (ja) | 1993-06-15 |
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