NO844371L - Analogifremgangsmaate for fremstilling av terapeutisk aktive purinderivater - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive purinderivaterInfo
- Publication number
- NO844371L NO844371L NO844371A NO844371A NO844371L NO 844371 L NO844371 L NO 844371L NO 844371 A NO844371 A NO 844371A NO 844371 A NO844371 A NO 844371A NO 844371 L NO844371 L NO 844371L
- Authority
- NO
- Norway
- Prior art keywords
- group
- general formula
- purine
- compound
- carbon atoms
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 8
- 150000003212 purines Chemical class 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 imino, sulfinyl Chemical group 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000012954 diazonium Substances 0.000 claims description 7
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- BBNKJGGCTNJDNI-UHFFFAOYSA-N 2-[3-methoxy-4-(7h-purin-8-yl)phenoxy]acetonitrile Chemical compound COC1=CC(OCC#N)=CC=C1C1=NC2=NC=NC=C2N1 BBNKJGGCTNJDNI-UHFFFAOYSA-N 0.000 claims description 3
- SAHZVUJIPRNYSV-UHFFFAOYSA-N 8-(2-methoxy-4-prop-2-ynoxyphenyl)-7h-purine Chemical compound COC1=CC(OCC#C)=CC=C1C1=NC2=NC=NC=C2N1 SAHZVUJIPRNYSV-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 230000036772 blood pressure Effects 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 230000009090 positive inotropic effect Effects 0.000 abstract description 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PPAULTVPKLVLII-UHFFFAOYSA-N 4,5-diaminopyrimidine Chemical compound NC1=CN=CN=C1N PPAULTVPKLVLII-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LGULZVMCNFWRHN-UHFFFAOYSA-N 2-[3-(cyanomethoxy)-4-(7h-purin-8-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC(OCC#N)=CC=C1C1=NC2=NC=NC=C2N1 LGULZVMCNFWRHN-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VJADEILCDRNMHJ-UHFFFAOYSA-N 3-n,3-n-dimethyl-4-(7h-purin-8-yl)benzene-1,3-diamine Chemical compound CN(C)C1=CC(N)=CC=C1C1=NC2=NC=NC=C2N1 VJADEILCDRNMHJ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PUTAXVMTHGJIDE-UHFFFAOYSA-N 8-(2-methoxy-4-prop-2-ynylsulfanylphenyl)-7h-purine Chemical compound COC1=CC(SCC#C)=CC=C1C1=NC2=NC=NC=C2N1 PUTAXVMTHGJIDE-UHFFFAOYSA-N 0.000 description 2
- XCLIATCXCZEVOG-UHFFFAOYSA-N 8-(2-methoxy-4-prop-2-ynylsulfonylphenyl)-7h-purine Chemical compound COC1=CC(S(=O)(=O)CC#C)=CC=C1C1=NC2=NC=NC=C2N1 XCLIATCXCZEVOG-UHFFFAOYSA-N 0.000 description 2
- XEYUPXYHVYEKCV-UHFFFAOYSA-N 8-[2,4-bis(prop-2-ynoxy)phenyl]-7h-purine Chemical compound C#CCOC1=CC(OCC#C)=CC=C1C1=NC2=NC=NC=C2N1 XEYUPXYHVYEKCV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- RIZQKJHWYJFKAP-UHFFFAOYSA-N 2-methoxy-4-prop-2-ynoxybenzoic acid Chemical compound COC1=CC(OCC#C)=CC=C1C(O)=O RIZQKJHWYJFKAP-UHFFFAOYSA-N 0.000 description 1
- QAAUAQMYDAVGAE-UHFFFAOYSA-N 2-methoxy-n-prop-2-ynyl-3-(7h-purin-8-yl)aniline Chemical compound COC1=C(NCC#C)C=CC=C1C1=NC2=NC=NC=C2N1 QAAUAQMYDAVGAE-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
- CLRDKRKWKIWCTR-UHFFFAOYSA-N 3-methoxy-4-(7H-purin-8-yl)phenol Chemical compound COC1=CC(O)=CC=C1C1=NC2=NC=NC=C2N1 CLRDKRKWKIWCTR-UHFFFAOYSA-N 0.000 description 1
- ZCLHLRUTLYSBLV-UHFFFAOYSA-N 3-methoxy-4-(7h-purin-8-yl)aniline Chemical compound COC1=CC(N)=CC=C1C1=NC2=NC=NC=C2N1 ZCLHLRUTLYSBLV-UHFFFAOYSA-N 0.000 description 1
- IDEFVFYTENHFRA-UHFFFAOYSA-N 3-methoxy-n-prop-2-ynyl-4-(7h-purin-8-yl)aniline Chemical compound COC1=CC(NCC#C)=CC=C1C1=NC2=NC=NC=C2N1 IDEFVFYTENHFRA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PJRDDSLCSGMJDA-UHFFFAOYSA-N 8-(2-ethoxy-4-prop-2-ynoxyphenyl)-7h-purine Chemical compound CCOC1=CC(OCC#C)=CC=C1C1=NC2=NC=NC=C2N1 PJRDDSLCSGMJDA-UHFFFAOYSA-N 0.000 description 1
- JSGQLNIRGRCNCH-UHFFFAOYSA-N 8-(2-methoxy-3-prop-2-ynoxyphenyl)-7h-purine Chemical compound COC1=C(OCC#C)C=CC=C1C1=NC2=NC=NC=C2N1 JSGQLNIRGRCNCH-UHFFFAOYSA-N 0.000 description 1
- XZPSRQHCPBAOFB-UHFFFAOYSA-N 8-(2-methoxy-5-prop-2-ynoxyphenyl)-7h-purine Chemical compound COC1=CC=C(OCC#C)C=C1C1=NC2=NC=NC=C2N1 XZPSRQHCPBAOFB-UHFFFAOYSA-N 0.000 description 1
- QQAVLQRPZJVPKQ-UHFFFAOYSA-N 8-[2,3-bis(prop-2-ynoxy)phenyl]-7h-purine Chemical compound C#CCOC1=CC=CC(C=2NC3=CN=CN=C3N=2)=C1OCC#C QQAVLQRPZJVPKQ-UHFFFAOYSA-N 0.000 description 1
- RBMHQRGXBZFYFY-UHFFFAOYSA-N 8-[2,5-bis(prop-2-ynoxy)phenyl]-7h-purine Chemical compound C#CCOC1=CC=C(OCC#C)C(C=2NC3=CN=CN=C3N=2)=C1 RBMHQRGXBZFYFY-UHFFFAOYSA-N 0.000 description 1
- JONVGXPYJPBXLF-UHFFFAOYSA-N 8-[3,4-bis(prop-2-ynoxy)phenyl]-7h-purine Chemical compound C1=C(OCC#C)C(OCC#C)=CC=C1C1=NC2=NC=NC=C2N1 JONVGXPYJPBXLF-UHFFFAOYSA-N 0.000 description 1
- VCKBLRUDDSFNTC-UHFFFAOYSA-N 8-[3,5-bis(prop-2-ynoxy)phenyl]-7h-purine Chemical compound C#CCOC1=CC(OCC#C)=CC(C=2NC3=CN=CN=C3N=2)=C1 VCKBLRUDDSFNTC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 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
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 210000005242 cardiac chamber Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- FHOQDZJLDBXRRX-UHFFFAOYSA-N methyl 2-[3-methoxy-4-(7h-purin-8-yl)anilino]acetate Chemical compound COC1=CC(NCC(=O)OC)=CC=C1C1=NC2=NC=NC=C2N1 FHOQDZJLDBXRRX-UHFFFAOYSA-N 0.000 description 1
- SLWCHNPJIWQNCR-UHFFFAOYSA-N methyl 2-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate Chemical compound COC(=O)COC1=CC=C(C(=O)OC)C(OC)=C1 SLWCHNPJIWQNCR-UHFFFAOYSA-N 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- ZMBYIAFIFOKSHF-UHFFFAOYSA-N n,n-dimethyl-5-prop-2-ynoxy-2-(7h-purin-8-yl)aniline Chemical compound CN(C)C1=CC(OCC#C)=CC=C1C1=NC2=NC=NC=C2N1 ZMBYIAFIFOKSHF-UHFFFAOYSA-N 0.000 description 1
- YARVZZAGDKUJQH-UHFFFAOYSA-N n,n-dimethyl-5-prop-2-ynylsulfanyl-2-(7h-purin-8-yl)aniline Chemical compound CN(C)C1=CC(SCC#C)=CC=C1C1=NC2=NC=NC=C2N1 YARVZZAGDKUJQH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000500 noncardiotoxic Toxicity 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HXBNENHPZIJFTQ-UHFFFAOYSA-N pyrimidine-4,5-diamine;hydrochloride Chemical compound Cl.NC1=CN=CN=C1N HXBNENHPZIJFTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833340076 DE3340076A1 (de) | 1983-11-05 | 1983-11-05 | Neue purinderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO844371L true NO844371L (no) | 1985-05-06 |
Family
ID=6213571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO844371A NO844371L (no) | 1983-11-05 | 1984-11-02 | Analogifremgangsmaate for fremstilling av terapeutisk aktive purinderivater |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0142075A2 (fi) |
| JP (1) | JPS60115583A (fi) |
| KR (1) | KR850003536A (fi) |
| AU (1) | AU3495984A (fi) |
| DD (1) | DD229701A5 (fi) |
| DE (1) | DE3340076A1 (fi) |
| DK (1) | DK523584A (fi) |
| ES (3) | ES537317A0 (fi) |
| FI (1) | FI844302L (fi) |
| GR (1) | GR80845B (fi) |
| HU (1) | HUT36121A (fi) |
| IL (1) | IL73407A0 (fi) |
| NO (1) | NO844371L (fi) |
| PT (1) | PT79446B (fi) |
| ZA (1) | ZA848565B (fi) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3522230A1 (de) * | 1985-06-21 | 1987-01-02 | Thomae Gmbh Dr K | Neue 2-arylimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
-
1983
- 1983-11-05 DE DE19833340076 patent/DE3340076A1/de not_active Withdrawn
-
1984
- 1984-10-23 EP EP84112738A patent/EP0142075A2/de not_active Withdrawn
- 1984-11-02 AU AU34959/84A patent/AU3495984A/en not_active Abandoned
- 1984-11-02 NO NO844371A patent/NO844371L/no unknown
- 1984-11-02 FI FI844302A patent/FI844302L/fi not_active Application Discontinuation
- 1984-11-02 JP JP59230520A patent/JPS60115583A/ja active Pending
- 1984-11-02 IL IL73407A patent/IL73407A0/xx unknown
- 1984-11-02 ES ES537317A patent/ES537317A0/es active Granted
- 1984-11-02 DD DD84269059A patent/DD229701A5/de unknown
- 1984-11-02 PT PT79446A patent/PT79446B/pt unknown
- 1984-11-02 ZA ZA848565A patent/ZA848565B/xx unknown
- 1984-11-02 DK DK523584A patent/DK523584A/da unknown
- 1984-11-03 KR KR1019840006898A patent/KR850003536A/ko not_active Application Discontinuation
- 1984-11-05 HU HU844099A patent/HUT36121A/hu unknown
- 1984-11-05 GR GR80845A patent/GR80845B/el unknown
-
1985
- 1985-03-07 ES ES541027A patent/ES541027A0/es active Granted
- 1985-03-07 ES ES541026A patent/ES541026A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DD229701A5 (de) | 1985-11-13 |
| DK523584A (da) | 1985-05-06 |
| HUT36121A (en) | 1985-08-28 |
| FI844302A0 (fi) | 1984-11-02 |
| ES8601203A1 (es) | 1985-10-16 |
| GR80845B (en) | 1985-03-04 |
| PT79446B (de) | 1986-11-13 |
| IL73407A0 (en) | 1985-02-28 |
| FI844302L (fi) | 1985-05-06 |
| EP0142075A2 (de) | 1985-05-22 |
| ES537317A0 (es) | 1985-10-16 |
| DE3340076A1 (de) | 1985-05-15 |
| DK523584D0 (da) | 1984-11-02 |
| ES8707534A1 (es) | 1985-12-01 |
| ES8707954A1 (es) | 1985-12-01 |
| PT79446A (de) | 1984-12-01 |
| ES541027A0 (es) | 1985-12-01 |
| AU3495984A (en) | 1985-05-09 |
| ZA848565B (en) | 1986-07-30 |
| JPS60115583A (ja) | 1985-06-22 |
| ES541026A0 (es) | 1985-12-01 |
| KR850003536A (ko) | 1985-06-20 |
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