NO854050L - Fremgangsm¨te for fremstilling av purinderivater. - Google Patents
Fremgangsm¨te for fremstilling av purinderivater.Info
- Publication number
- NO854050L NO854050L NO854050A NO854050A NO854050L NO 854050 L NO854050 L NO 854050L NO 854050 A NO854050 A NO 854050A NO 854050 A NO854050 A NO 854050A NO 854050 L NO854050 L NO 854050L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- amino
- methyl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000003212 purines Chemical class 0.000 title claims description 5
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 101
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 22
- 238000010992 reflux Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- -1 alkanoyl halide Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- 235000019253 formic acid Nutrition 0.000 claims description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- HANOSGYMKMNFON-UHFFFAOYSA-N 2,8-diamino-9-(thiophen-2-ylmethyl)-3h-purin-6-one Chemical compound NC1=NC(C(N=C(N)N2)=O)=C2N1CC1=CC=CS1 HANOSGYMKMNFON-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 101100134925 Gallus gallus COR6 gene Chemical group 0.000 claims description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- HJXJNSKEOFNHCU-UHFFFAOYSA-N thiohypobromous acid Chemical compound BrS HJXJNSKEOFNHCU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 125000001072 heteroaryl group Chemical group 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000538 analytical sample Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 5
- UTTPUMOOQSNOHH-UHFFFAOYSA-N 2-amino-6-chloro-5-nitro-1h-pyrimidin-4-one Chemical compound NC1=NC(=O)C([N+]([O-])=O)=C(Cl)N1 UTTPUMOOQSNOHH-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002832 nitroso derivatives Chemical class 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VBWACOJLJYUFKJ-UHFFFAOYSA-N 2-amino-6-chloro-1h-pyrimidin-4-one Chemical compound NC1=NC(O)=CC(Cl)=N1 VBWACOJLJYUFKJ-UHFFFAOYSA-N 0.000 description 3
- KBQIJULVUFJCMD-UHFFFAOYSA-N 2-amino-6-chloro-1h-pyrimidin-4-one;hydrate Chemical compound O.NC1=NC(=O)C=C(Cl)N1 KBQIJULVUFJCMD-UHFFFAOYSA-N 0.000 description 3
- RTFXTKZURZECQR-UHFFFAOYSA-N 2-amino-8-bromo-9-(thiophen-2-ylmethyl)-3h-purin-6-one Chemical compound BrC1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=CS1 RTFXTKZURZECQR-UHFFFAOYSA-N 0.000 description 3
- XGUKQMNJZJKOAB-UHFFFAOYSA-N 2-amino-9-(thiophen-2-ylmethyl)-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=CS1 XGUKQMNJZJKOAB-UHFFFAOYSA-N 0.000 description 3
- FLFZMCJIHCDWKG-UHFFFAOYSA-N 2-nitrosopyrimidine Chemical compound O=NC1=NC=CC=N1 FLFZMCJIHCDWKG-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 description 2
- RRHCYHMIRJNBBE-UHFFFAOYSA-N 2,5-diamino-6-(thiophen-2-ylmethylamino)-1h-pyrimidin-4-one Chemical compound NC1=NC(O)=C(N)C(NCC=2SC=CC=2)=N1 RRHCYHMIRJNBBE-UHFFFAOYSA-N 0.000 description 2
- DPDYTYOWSIRPMB-UHFFFAOYSA-N 2,8-diamino-9-benzyl-3h-purin-6-one Chemical compound NC1=NC(C(N=C(N)N2)=O)=C2N1CC1=CC=CC=C1 DPDYTYOWSIRPMB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- FWGSCBXLUQAPSJ-UHFFFAOYSA-N 2-amino-9-(pyridin-3-ylmethyl)-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=CN=C1 FWGSCBXLUQAPSJ-UHFFFAOYSA-N 0.000 description 2
- IZJOIOLODSTRKQ-UHFFFAOYSA-N 2-amino-9-(thiophen-3-ylmethyl)-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1CC=1C=CSC=1 IZJOIOLODSTRKQ-UHFFFAOYSA-N 0.000 description 2
- UQOKRDJILZMZKU-UHFFFAOYSA-N 2-nitropyrimidine Chemical compound [O-][N+](=O)C1=NC=CC=N1 UQOKRDJILZMZKU-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- UUYYBUQXUBNWBO-UHFFFAOYSA-N 6-chloro-9-[(2,5-dimethylthiophen-3-yl)methyl]purin-2-amine Chemical compound S1C(C)=CC(CN2C3=NC(N)=NC(Cl)=C3N=C2)=C1C UUYYBUQXUBNWBO-UHFFFAOYSA-N 0.000 description 2
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- 241001432959 Chernes Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- GXHYIFCRBFLFJV-UHFFFAOYSA-N n-[2-amino-4-oxo-6-(thiophen-2-ylmethylamino)-1h-pyrimidin-5-yl]formamide Chemical compound NC1=NC(O)=C(NC=O)C(NCC=2SC=CC=2)=N1 GXHYIFCRBFLFJV-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- UVCDLICHQNGTDQ-UHFFFAOYSA-N (2-methylthiophen-3-yl)methanamine Chemical compound CC=1SC=CC=1CN UVCDLICHQNGTDQ-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SWZNXCABBUKIPZ-UHFFFAOYSA-N (3-methylthiophen-2-yl)methanamine Chemical compound CC=1C=CSC=1CN SWZNXCABBUKIPZ-UHFFFAOYSA-N 0.000 description 1
- CKQHNKAVFNDGMK-UHFFFAOYSA-N (4-methylthiophen-2-yl)methanamine Chemical compound CC1=CSC(CN)=C1 CKQHNKAVFNDGMK-UHFFFAOYSA-N 0.000 description 1
- NUOZTFAOKMVNAU-UHFFFAOYSA-N (4-methylthiophen-3-yl)methanamine Chemical compound CC1=CSC=C1CN NUOZTFAOKMVNAU-UHFFFAOYSA-N 0.000 description 1
- XCBYYXLOEBELSB-UHFFFAOYSA-N (5-methylthiophen-2-yl)methanamine Chemical compound CC1=CC=C(CN)S1 XCBYYXLOEBELSB-UHFFFAOYSA-N 0.000 description 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- YFEQTUUFQKDATK-UHFFFAOYSA-N 1,3-thiazol-4-ylmethanamine Chemical class NCC1=CSC=N1 YFEQTUUFQKDATK-UHFFFAOYSA-N 0.000 description 1
- WHTPXNOFEHTZAD-UHFFFAOYSA-N 1-benzothiophen-3-ylmethanamine Chemical compound C1=CC=C2C(CN)=CSC2=C1 WHTPXNOFEHTZAD-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO892780A NO892780D0 (no) | 1984-10-12 | 1989-07-05 | Nye (oksazolo(5,4-d)pyrimidin-2-yl)karbamater. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66015284A | 1984-10-12 | 1984-10-12 | |
| US06/767,202 US4772606A (en) | 1985-08-22 | 1985-08-22 | Purine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO854050L true NO854050L (no) | 1986-04-14 |
Family
ID=27097992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO854050A NO854050L (no) | 1984-10-12 | 1985-10-11 | Fremgangsm¨te for fremstilling av purinderivater. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0178178A3 (da) |
| KR (1) | KR860003255A (da) |
| AU (1) | AU584126B2 (da) |
| CA (1) | CA1260934A (da) |
| DK (1) | DK458485A (da) |
| ES (2) | ES8609328A1 (da) |
| FI (1) | FI853891L (da) |
| GR (1) | GR852468B (da) |
| HU (1) | HU197747B (da) |
| IL (1) | IL76546A (da) |
| NO (1) | NO854050L (da) |
| NZ (1) | NZ213798A (da) |
| OA (1) | OA08120A (da) |
| PH (1) | PH22811A (da) |
| PT (1) | PT81293B (da) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ228645A (en) * | 1988-04-11 | 1991-09-25 | Iaf Biochem Int | 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections |
| DK0460116T3 (da) * | 1989-02-27 | 1998-03-30 | Biocryst Pharm Inc | 9-substitueret-8-usubstitueret-9-deazaguaniner |
| US4939252A (en) * | 1989-04-20 | 1990-07-03 | Hoffmann-La Roche Inc. | Novel intermediates for the preparation of Carbovir |
| IL94390A (en) * | 1989-05-30 | 1996-03-31 | Merck & Co Inc | The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them |
| US5217983A (en) * | 1992-03-27 | 1993-06-08 | Du Pont Merck Pharmaceutical Company | (N-benzyl) acetaldehyde bicyclic heterocycles useful as topical antiinflammatories |
| US5272169A (en) * | 1992-03-27 | 1993-12-21 | The Dupont Merck Pharmaceutical Company | (N-benzyl) acetaldehyde bicyclic heterocycles useful as topical antiinflammatories |
| EP0784624A1 (en) * | 1994-10-05 | 1997-07-23 | Chiroscience Limited | Purine and guanine compounds as inhibitors of pnp |
| DE19501482A1 (de) * | 1995-01-19 | 1996-07-25 | Bayer Ag | 2,9-disubstituierte Purin-6-one |
| GB9520364D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compouundds |
| GB9520363D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compounds |
| DE19541264A1 (de) * | 1995-11-06 | 1997-05-07 | Bayer Ag | Purin-6-on-derivate |
| US7241890B2 (en) | 2001-10-30 | 2007-07-10 | Conforma Therapeutics Corporation | Purine analogs having HSP90-inhibiting activity |
| WO2005028434A2 (en) | 2003-09-18 | 2005-03-31 | Conforma Therapeutics Corporation | Novel heterocyclic compounds as hsp90-inhibitors |
| CA2602257A1 (en) | 2005-03-30 | 2006-10-05 | Conforma Therapeutics Corporation | Alkynyl pyrrolopyrimidines and related analogs as hsp90-inhibitors |
| WO2013066729A1 (en) | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2844578A (en) * | 1955-09-14 | 1958-07-22 | Du Pont | Pyrimidine derivatives |
-
1985
- 1985-10-02 IL IL76546A patent/IL76546A/xx unknown
- 1985-10-04 AU AU48292/85A patent/AU584126B2/en not_active Ceased
- 1985-10-07 FI FI853891A patent/FI853891L/fi not_active Application Discontinuation
- 1985-10-08 DK DK458485A patent/DK458485A/da not_active Application Discontinuation
- 1985-10-10 CA CA000492727A patent/CA1260934A/en not_active Expired
- 1985-10-10 PH PH32916A patent/PH22811A/en unknown
- 1985-10-11 GR GR852468A patent/GR852468B/el unknown
- 1985-10-11 EP EP85307283A patent/EP0178178A3/en not_active Withdrawn
- 1985-10-11 HU HU853956A patent/HU197747B/hu not_active IP Right Cessation
- 1985-10-11 NO NO854050A patent/NO854050L/no unknown
- 1985-10-11 NZ NZ213798A patent/NZ213798A/xx unknown
- 1985-10-11 PT PT81293A patent/PT81293B/pt not_active IP Right Cessation
- 1985-10-11 ES ES547805A patent/ES8609328A1/es not_active Expired
- 1985-10-11 OA OA58702A patent/OA08120A/xx unknown
- 1985-10-12 KR KR1019850007507A patent/KR860003255A/ko not_active IP Right Cessation
-
1986
- 1986-04-01 ES ES553606A patent/ES8801273A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8609328A1 (es) | 1986-09-01 |
| OA08120A (fr) | 1987-03-31 |
| NZ213798A (en) | 1989-01-06 |
| KR860003255A (ko) | 1986-05-21 |
| FI853891A0 (fi) | 1985-10-07 |
| EP0178178A2 (en) | 1986-04-16 |
| PT81293B (pt) | 1988-02-17 |
| DK458485D0 (da) | 1985-10-08 |
| ES8801273A1 (es) | 1987-12-16 |
| AU4829285A (en) | 1986-04-17 |
| PT81293A (en) | 1985-11-01 |
| FI853891L (fi) | 1986-04-13 |
| GR852468B (da) | 1986-02-12 |
| IL76546A0 (en) | 1986-02-28 |
| PH22811A (en) | 1988-12-27 |
| HUT40131A (en) | 1986-11-28 |
| ES553606A0 (es) | 1987-12-16 |
| ES547805A0 (es) | 1986-09-01 |
| DK458485A (da) | 1986-04-13 |
| CA1260934A (en) | 1989-09-26 |
| AU584126B2 (en) | 1989-05-18 |
| HU197747B (en) | 1989-05-29 |
| IL76546A (en) | 1988-12-30 |
| EP0178178A3 (en) | 1987-08-12 |
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