JPH0455193B2 - - Google Patents
Info
- Publication number
- JPH0455193B2 JPH0455193B2 JP59235364A JP23536484A JPH0455193B2 JP H0455193 B2 JPH0455193 B2 JP H0455193B2 JP 59235364 A JP59235364 A JP 59235364A JP 23536484 A JP23536484 A JP 23536484A JP H0455193 B2 JPH0455193 B2 JP H0455193B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyrimidine
- hydroxyethyl
- amino
- general formula
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 hydroxyethyl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 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 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 claims 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 7
- NWCVGIMEZSWINX-UHFFFAOYSA-N 2-[[5-(diethylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-hexylamino]ethanol Chemical compound CCCCCCN(CCO)C1=CC(N(CC)CC)=NC2=NC=NN12 NWCVGIMEZSWINX-UHFFFAOYSA-N 0.000 claims 3
- KAZRDYSBBJYXOQ-UHFFFAOYSA-N 2-[[5-(diethylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-pentylamino]ethanol Chemical compound CCCCCN(CCO)C1=CC(N(CC)CC)=NC2=NC=NN12 KAZRDYSBBJYXOQ-UHFFFAOYSA-N 0.000 claims 3
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 claims 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 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- JANOITYENFDMAC-UHFFFAOYSA-N 2-[pentyl-(5-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound N=1C2=NC=NN2C(N(CCO)CCCCC)=CC=1N1CCCCC1 JANOITYENFDMAC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 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 16
- 239000000203 mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229960000363 trapidil Drugs 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000002776 aggregation Effects 0.000 description 9
- 238000004220 aggregation Methods 0.000 description 8
- 229940114079 arachidonic acid Drugs 0.000 description 8
- 235000021342 arachidonic acid Nutrition 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 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 6
- 210000004623 platelet-rich plasma Anatomy 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 5
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 230000001746 atrial effect Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000011533 pre-incubation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- DDMGAAYEUNWXSI-XVSDJDOKSA-M sodium;(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate Chemical compound [Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O DDMGAAYEUNWXSI-XVSDJDOKSA-M 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000004520 agglutination Effects 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 230000003185 calcium uptake Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000010253 intravenous injection 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
- 238000005259 measurement Methods 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LEYYLQKYOZYCRF-UHFFFAOYSA-N 1-(hexylamino)ethanol Chemical compound CCCCCCNC(C)O LEYYLQKYOZYCRF-UHFFFAOYSA-N 0.000 description 1
- RUDUVMFDZBMVPE-UHFFFAOYSA-N 2-(2-ethoxyethylamino)ethanol Chemical compound CCOCCNCCO RUDUVMFDZBMVPE-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
- 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
- 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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- 206010003497 Asphyxia Diseases 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
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- 241000283690 Bos taurus Species 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000001321 subclavian vein Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 210000003462 vein Anatomy 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD84262043A DD228811A1 (de) | 1984-04-17 | 1984-04-17 | Verfahren zur herstellung von neuen triazolopyrimidinen |
| DD07D/262043-8 | 1984-04-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60224692A JPS60224692A (ja) | 1985-11-09 |
| JPH0455193B2 true JPH0455193B2 (da) | 1992-09-02 |
Family
ID=5556238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59235364A Granted 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 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS60224692A (da) |
| AT (1) | AT391866B (da) |
| BE (2) | BE902218A (da) |
| CH (1) | CH669196A5 (da) |
| DD (1) | DD228811A1 (da) |
| DE (1) | DE3512629C2 (da) |
| ES (1) | ES8706682A1 (da) |
| FR (1) | FR2562895B1 (da) |
| GB (1) | GB2157684B (da) |
| LT (1) | LT2594B (da) |
| MD (1) | MD59C2 (da) |
| NL (1) | NL8501111A (da) |
| SE (1) | SE466104B (da) |
| SU (1) | SU1468423A3 (da) |
| YU (1) | YU47167B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| EP0757984B1 (en) * | 1995-08-08 | 2002-10-30 | Ono Pharmaceutical Co., Ltd. | Hydroxamic acid derivatives useful for inhibiting gelatinase |
| JP2001322933A (ja) | 2000-05-15 | 2001-11-20 | Ucb Sa | Ｃｄ４０シグナル遮断剤 |
| 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 |
| CA3056909A1 (en) | 2017-03-24 | 2018-09-27 | Nanosyn, Inc. | Fused triazolo-pyrimidine compounds having useful pharmaceutical application |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD61269A (da) * | ||||
| 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 ES ES542269A patent/ES8706682A1/es not_active Expired
- 1985-04-16 NL NL8501111A patent/NL8501111A/nl active Search and Examination
- 1985-04-16 SU SU853884102A patent/SU1468423A3/ru active
- 1985-04-16 YU YU64185A patent/YU47167B/sh unknown
- 1985-04-16 CH CH1624/85A patent/CH669196A5/de not_active IP Right Cessation
- 1985-04-17 FR FR8505831A patent/FR2562895B1/fr not_active Expired
- 1985-04-17 BE BE0/214861A patent/BE902218A/fr not_active IP Right Cessation
- 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 |
|---|---|
| FR2562895A1 (fr) | 1985-10-18 |
| MD59C2 (ro) | 1995-01-31 |
| LT2594B (lt) | 1994-03-25 |
| BE902218A (fr) | 1985-08-16 |
| GB2157684B (en) | 1987-11-11 |
| SU1468423A3 (ru) | 1989-03-23 |
| SE8501835D0 (sv) | 1985-04-15 |
| SE466104B (sv) | 1991-12-16 |
| FR2562895B1 (fr) | 1988-10-07 |
| AT391866B (de) | 1990-12-10 |
| MD59B1 (ro) | 1994-08-31 |
| DE3512629C2 (de) | 1995-07-06 |
| JPS60224692A (ja) | 1985-11-09 |
| GB8509561D0 (en) | 1985-05-22 |
| BE903828R (fr) | 1986-04-01 |
| YU47167B (sh) | 1995-01-31 |
| ES8706682A1 (es) | 1987-07-01 |
| NL8501111A (nl) | 1985-11-18 |
| GB2157684A (en) | 1985-10-30 |
| SE8501835L (sv) | 1985-10-18 |
| CH669196A5 (de) | 1989-02-28 |
| DE3512629A1 (de) | 1986-10-09 |
| DD228811A1 (de) | 1985-10-23 |
| ATA105085A (de) | 1990-06-15 |
| YU64185A (sh) | 1992-09-07 |
| ES542269A0 (es) | 1987-07-01 |
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