DE2804723A1 - 9-(2,6-dihalogenbenzyl)-adenine und verfahren zu ihrer herstellung und reinigung - Google Patents
9-(2,6-dihalogenbenzyl)-adenine und verfahren zu ihrer herstellung und reinigungInfo
- Publication number
- DE2804723A1 DE2804723A1 DE19782804723 DE2804723A DE2804723A1 DE 2804723 A1 DE2804723 A1 DE 2804723A1 DE 19782804723 DE19782804723 DE 19782804723 DE 2804723 A DE2804723 A DE 2804723A DE 2804723 A1 DE2804723 A1 DE 2804723A1
- Authority
- DE
- Germany
- Prior art keywords
- adenine
- chloro
- fluorobenzyl
- liquid
- isomer
- 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.)
- Granted
Links
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 title claims description 99
- 229960000643 adenine Drugs 0.000 title claims description 59
- 229930024421 Adenine Natural products 0.000 title claims description 56
- 238000000034 method Methods 0.000 title claims description 39
- 238000004140 cleaning Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- -1 alkaline earth metal salt Chemical class 0.000 claims description 68
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 44
- 239000007788 liquid Substances 0.000 claims description 38
- NAPNOSFRRMHNBJ-UHFFFAOYSA-N Arprinocid Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=C(F)C=CC=C1Cl NAPNOSFRRMHNBJ-UHFFFAOYSA-N 0.000 claims description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 33
- 230000029936 alkylation Effects 0.000 claims description 29
- 238000005804 alkylation reaction Methods 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000012071 phase Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 23
- 239000007791 liquid phase Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 20
- 239000003444 phase transfer catalyst Substances 0.000 claims description 20
- 229910052708 sodium Inorganic materials 0.000 claims description 18
- 239000011734 sodium Substances 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000008096 xylene Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- MJGOLNNLNQQIHR-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1CCl MJGOLNNLNQQIHR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- 238000010555 transalkylation reaction Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000007790 solid phase Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 150000003738 xylenes Chemical class 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
- BVIVTIQQPSNGIK-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methyl]-7h-purin-6-amine Chemical class N=1C=2N=CNC=2C(N)=NC=1CC1=C(F)C=CC=C1Cl BVIVTIQQPSNGIK-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- IZCBDBAVZPTJIH-UHFFFAOYSA-N 9-[(2,6-dichlorophenyl)methyl]purin-6-amine Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=C(Cl)C=CC=C1Cl IZCBDBAVZPTJIH-UHFFFAOYSA-N 0.000 claims description 3
- 150000005224 alkoxybenzenes Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- UFWMNRZVXATFAY-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]-7h-purin-6-amine Chemical class N=1C=2N=CNC=2C(N)=NC=1CC1=C(Cl)C=CC=C1Cl UFWMNRZVXATFAY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
- 239000000047 product Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 25
- 238000004811 liquid chromatography Methods 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- UZYYBZNZSSNYSA-UHFFFAOYSA-N 1,2,4-trichloro-3-methylbenzene Chemical compound CC1=C(Cl)C=CC(Cl)=C1Cl UZYYBZNZSSNYSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 208000003495 Coccidiosis Diseases 0.000 description 3
- 206010023076 Isosporiasis Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
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- 150000003230 pyrimidines Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003613 toluenes Chemical class 0.000 description 3
- GVULSXIBCHPJEH-UHFFFAOYSA-N (2-chloro-6-fluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1Cl GVULSXIBCHPJEH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000027954 Poultry disease Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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- 238000002835 absorbance Methods 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
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- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
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- 125000005517 carbenium group Chemical group 0.000 description 1
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- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/766,326 US4100159A (en) | 1977-02-07 | 1977-02-07 | Process for preparation of 9-(2,6-dihalobenzyl)adenines |
| US05/768,235 US4098787A (en) | 1977-02-14 | 1977-02-14 | Process for preparation of 9-(dihalobenzyl) adenines |
| US84391977A | 1977-10-20 | 1977-10-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2804723A1 true DE2804723A1 (de) | 1978-08-10 |
| DE2804723C2 DE2804723C2 (en, 2012) | 1990-11-29 |
Family
ID=27419624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782804723 Granted DE2804723A1 (de) | 1977-02-07 | 1978-02-03 | 9-(2,6-dihalogenbenzyl)-adenine und verfahren zu ihrer herstellung und reinigung |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS53124294A (en, 2012) |
| AR (1) | AR225000A1 (en, 2012) |
| AT (1) | AT361008B (en, 2012) |
| CH (1) | CH636614A5 (en, 2012) |
| DD (1) | DD136744A5 (en, 2012) |
| DE (1) | DE2804723A1 (en, 2012) |
| DK (1) | DK36078A (en, 2012) |
| EG (1) | EG13333A (en, 2012) |
| ES (1) | ES466647A1 (en, 2012) |
| FI (1) | FI64596C (en, 2012) |
| FR (1) | FR2379536A1 (en, 2012) |
| GB (1) | GB1586537A (en, 2012) |
| GR (1) | GR64457B (en, 2012) |
| IE (1) | IE46399B1 (en, 2012) |
| IL (1) | IL53922A (en, 2012) |
| IT (1) | IT1105174B (en, 2012) |
| NL (1) | NL7800896A (en, 2012) |
| NO (1) | NO148374C (en, 2012) |
| NZ (1) | NZ186357A (en, 2012) |
| PL (1) | PL118655B1 (en, 2012) |
| PT (1) | PT67606B (en, 2012) |
| SE (1) | SE440355B (en, 2012) |
| YU (1) | YU27778A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089618A (en) * | 1989-08-01 | 1992-02-18 | Lonza Ltd. | Process for the purification of adenine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900826A (en) * | 1981-09-24 | 1990-02-13 | Kohjin Co., Ltd. | Process for preparing N6,9-disubstituted adenine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846426A (en) * | 1971-03-03 | 1974-11-05 | Int Minerals & Chem Corp | 6-amino-9-(substituted benzyl) purines and their n{11 oxides |
-
1978
- 1978-01-23 FI FI780200A patent/FI64596C/fi not_active IP Right Cessation
- 1978-01-25 DK DK36078A patent/DK36078A/da not_active Application Discontinuation
- 1978-01-25 NL NL7800896A patent/NL7800896A/xx not_active Application Discontinuation
- 1978-01-26 NO NO780284A patent/NO148374C/no unknown
- 1978-01-26 SE SE7800977A patent/SE440355B/sv not_active IP Right Cessation
- 1978-01-30 IL IL53922A patent/IL53922A/xx unknown
- 1978-01-31 NZ NZ186357A patent/NZ186357A/xx unknown
- 1978-01-31 AR AR270912A patent/AR225000A1/es active
- 1978-02-02 GR GR55327A patent/GR64457B/el unknown
- 1978-02-02 PT PT67606A patent/PT67606B/pt unknown
- 1978-02-03 DE DE19782804723 patent/DE2804723A1/de active Granted
- 1978-02-03 FR FR7803115A patent/FR2379536A1/fr active Granted
- 1978-02-03 DD DD78203555A patent/DD136744A5/xx unknown
- 1978-02-03 CH CH124478A patent/CH636614A5/de not_active IP Right Cessation
- 1978-02-03 ES ES466647A patent/ES466647A1/es not_active Expired
- 1978-02-04 PL PL1978204447A patent/PL118655B1/pl unknown
- 1978-02-06 GB GB4691/78A patent/GB1586537A/en not_active Expired
- 1978-02-06 EG EG76/78A patent/EG13333A/xx active
- 1978-02-06 YU YU00277/78A patent/YU27778A/xx unknown
- 1978-02-06 IE IE253/78A patent/IE46399B1/en unknown
- 1978-02-06 IT IT47941/78A patent/IT1105174B/it active
- 1978-02-06 AT AT79778A patent/AT361008B/de not_active IP Right Cessation
- 1978-02-07 JP JP1290178A patent/JPS53124294A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846426A (en) * | 1971-03-03 | 1974-11-05 | Int Minerals & Chem Corp | 6-amino-9-(substituted benzyl) purines and their n{11 oxides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089618A (en) * | 1989-08-01 | 1992-02-18 | Lonza Ltd. | Process for the purification of adenine |
Also Published As
| Publication number | Publication date |
|---|---|
| IL53922A (en) | 1981-02-27 |
| NO780284L (no) | 1978-08-08 |
| GB1586537A (en) | 1981-03-18 |
| GR64457B (en) | 1980-03-24 |
| ATA79778A (de) | 1980-07-15 |
| YU27778A (en) | 1983-12-31 |
| FI64596C (fi) | 1983-12-12 |
| ES466647A1 (es) | 1980-12-16 |
| IE46399B1 (en) | 1983-06-01 |
| DE2804723C2 (en, 2012) | 1990-11-29 |
| IT1105174B (it) | 1985-10-28 |
| PL204447A1 (pl) | 1979-06-04 |
| IE780253L (en) | 1978-08-07 |
| DD136744A5 (de) | 1979-07-25 |
| PL118655B1 (en) | 1981-10-31 |
| NZ186357A (en) | 1981-03-16 |
| NO148374B (no) | 1983-06-20 |
| FI64596B (fi) | 1983-08-31 |
| IT7847941A0 (it) | 1978-02-06 |
| SE7800977L (sv) | 1978-08-08 |
| PT67606A (en) | 1978-03-01 |
| FR2379536B1 (en, 2012) | 1983-10-07 |
| DK36078A (da) | 1978-08-08 |
| IL53922A0 (en) | 1978-04-30 |
| AT361008B (de) | 1981-02-10 |
| NL7800896A (nl) | 1978-08-09 |
| NO148374C (no) | 1983-09-28 |
| AR225000A1 (es) | 1982-02-15 |
| FR2379536A1 (fr) | 1978-09-01 |
| SE440355B (sv) | 1985-07-29 |
| PT67606B (en) | 1980-03-03 |
| JPS53124294A (en) | 1978-10-30 |
| EG13333A (en) | 1981-06-30 |
| FI780200A7 (fi) | 1978-08-08 |
| CH636614A5 (en) | 1983-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |