NO863309L - Guaninderivater. - Google Patents

Guaninderivater.

Info

Publication number: NO863309L
Authority: NO; Norway
Prior art keywords: formula; compound; salt; group; hydroxy
Prior art date: 1985-08-16

Application number

NO863309A

Other languages

English (en)

Norwegian (no)

Other versions

NO863309D0 (no

Inventor

Alan David Brothwick

Barrie Edward Kirk

Derek Norman Evans

Keith Biggadike

Leslie Stephenson

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

1985-08-16

Filing date

1986-08-15

Publication date

1987-02-17

1985-08-16 Priority claimed from GB858520553A external-priority patent/GB8520553D0/en

1986-06-13 Priority claimed from GB868614395A external-priority patent/GB8614395D0/en

1986-08-15 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1986-08-15 Publication of NO863309D0 publication Critical patent/NO863309D0/no

1987-02-17 Publication of NO863309L publication Critical patent/NO863309L/no

Links

UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 132
150000003839 salts Chemical class 0.000 claims description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
238000000034 method Methods 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 26
125000006239 protecting group Chemical group 0.000 claims description 23
239000000047 product Substances 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
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 4
125000000217 alkyl group Chemical group 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
150000004675 formic acid derivatives Chemical class 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
239000012954 diazonium Substances 0.000 claims description 2
150000001989 diazonium salts Chemical class 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
150000003212 purines Chemical class 0.000 claims description 2
239000012467 final product Substances 0.000 claims 3
229960002944 cyclofenil Drugs 0.000 claims 1
238000006193 diazotization reaction Methods 0.000 claims 1
230000000865 phosphorylative effect Effects 0.000 claims 1
150000003461 sulfonyl halides Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 48
239000002904 solvent Substances 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000543 intermediate Substances 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
239000007787 solid Substances 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
239000002585 base Substances 0.000 description 20
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
-1 glutaconates Chemical class 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
150000004712 monophosphates Chemical class 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000001914 filtration Methods 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
239000013067 intermediate product Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000006188 syrup Substances 0.000 description 6
235000020357 syrup Nutrition 0.000 description 6
238000011282 treatment Methods 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
102000006601 Thymidine Kinase Human genes 0.000 description 5
108020004440 Thymidine kinase Proteins 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
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 4
102100022464 5'-nucleotidase Human genes 0.000 description 4
102000002260 Alkaline Phosphatase Human genes 0.000 description 4
108020004774 Alkaline Phosphatase Proteins 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
229940099112 cornstarch Drugs 0.000 description 4
239000013078 crystal Substances 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000007888 film coating Substances 0.000 description 4
238000009501 film coating Methods 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum 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
239000000375 suspending agent Substances 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
208000009889 Herpes Simplex Diseases 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
241000700605 Viruses Species 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000012025 fluorinating agent Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002777 nucleoside Substances 0.000 description 3
108010028584 nucleotidase Proteins 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229940056211 paraffin Drugs 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
108010043671 prostatic acid phosphatase Proteins 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000008109 sodium starch glycolate Substances 0.000 description 3
229940079832 sodium starch glycolate Drugs 0.000 description 3
229920003109 sodium starch glycolate Polymers 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000011200 topical administration Methods 0.000 description 3
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 2
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700584 Simplexvirus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
208000036142 Viral infection Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
229940063655 aluminum stearate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
239000008365 aqueous carrier Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-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
230000015572 biosynthetic process Effects 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
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230000008569 process Effects 0.000 description 1
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235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
206010037844 rash Diseases 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
238000005245 sintering Methods 0.000 description 1
206010040872 skin infection Diseases 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002435 venom Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
231100000611 venom Toxicity 0.000 description 1
210000003501 vero cell Anatomy 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO863309A 1985-08-16 1986-08-15 Guaninderivater. NO863309L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB858520553A GB8520553D0 (en)	1985-08-16	1985-08-16	Chemical compound
GB868614395A GB8614395D0 (en)	1986-06-13	1986-06-13	Chemical compounds

Publications (2)

Publication Number	Publication Date
NO863309D0 NO863309D0 (no)	1986-08-15
NO863309L true NO863309L (no)	1987-02-17

Family

ID=26289669

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO863309A NO863309L (no)	1985-08-16	1986-08-15	Guaninderivater.

Country Status (16)

Country	Link
US (1)	US4857531A (pt)
EP (1)	EP0212956B1 (pt)
KR (1)	KR870002141A (pt)
CN (1)	CN86106214A (pt)
AU (1)	AU597266B2 (pt)
CA (1)	CA1266863A (pt)
DE (1)	DE3675846D1 (pt)
DK (1)	DK390986A (pt)
ES (1)	ES2001094A6 (pt)
FI (1)	FI863322A7 (pt)
GB (1)	GB2179349A (pt)
GR (1)	GR862141B (pt)
IL (1)	IL79727A (pt)
NO (1)	NO863309L (pt)
NZ (1)	NZ217220A (pt)
PT (1)	PT83201A (pt)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0277599A3 (en) *	1987-01-30	1990-05-09	Asahi Glass Company Ltd.	Fluorine containing cyclopentane derivatives and processes for their production
US4855466A (en) *	1987-12-28	1989-08-08	E. R. Squibb & Sons, Inc.	Purinyl cyclobutanes
GB8813148D0 (en) *	1988-06-03	1988-07-06	Glaxo Group Ltd	Chemical compounds
US5155112A (en) *	1988-06-03	1992-10-13	Glaxo Group Limited	Cyclopentane derivatives
GB8815265D0 (en) *	1988-06-27	1988-08-03	Wellcome Found	Therapeutic nucleosides
US4939252A (en) *	1989-04-20	1990-07-03	Hoffmann-La Roche Inc.	Novel intermediates for the preparation of Carbovir
EP0410660A1 (en) *	1989-07-24	1991-01-30	Glaxo Group Limited	Cyclopentane derivatives
US6001840A (en) *	1990-03-06	1999-12-14	Southern Research Institute	Methods of treatment of viral infections using carbocyclic deoxyguanosine analogs
JPH04505768A (ja) *	1990-03-06	1992-10-08	ヴィラケム・インコーポレーテッド	サイトメガロウイルス感染の予防および治療のための方法および組成物
CA2042931A1 (en) *	1990-05-24	1991-11-25	Robert Zahler	Fluorinated bis (hydroxymethyl) cyclobutyl purines and pyrimidines
GB9108376D0 (en) *	1991-04-19	1991-06-05	Enzymatix Ltd	Cyclopentenes
JPH08505835A (ja) *	1992-04-21	1996-06-25	カイロサイエンス・リミテッド	キラルシクロペンテン誘導体及びそれらの製造
US5840923A (en) *	1992-04-21	1998-11-24	Chiroscience Limited	Chiral cyclopentene derivatives and their preparation
US8441214B2 (en) *	2009-03-11	2013-05-14	Deloren E. Anderson	Light array maintenance system and method
US9700560B2 (en) *	2009-11-16	2017-07-11	University Of Georgia Research Foundation, Inc.	2′-fluoro-6′-methylene carbocyclic nucleosides and methods of treating viral infections

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4383114A (en) *	1977-02-09	1983-05-10	Regents Of The University Of Minnesota	Adenosine deaminase resistant antiviral purine arabinonucleosides
SE8203855D0 (sv) *	1982-06-21	1982-06-21	Astra Laekemedel Ab	Novel derivatives of guanine i
ATE36325T1 (de) *	1982-09-17	1988-08-15	Glaxo Group Ltd	Derivate von 5-halovinyl-2'-deoxyuridin.
EP0138683A3 (en) *	1983-09-30	1988-01-20	Merck & Co. Inc.	Purine derivatives, their application in anti-viral compositions
US4728736A (en) *	1984-03-28	1988-03-01	Southern Research Institute	Carbocyclic analogs of purine ribofuranosides
US4543255A (en) *	1984-05-10	1985-09-24	Southern Research Institute	Carbocyclic analogs of purine 2'-deoxyribofuranosides
US4605659A (en) *	1985-04-30	1986-08-12	Syntex (U.S.A.) Inc.	Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals
IL78643A0 (en) *	1985-05-02	1986-08-31	Wellcome Found	Purine derivatives,their preparation and pharmaceutical compositions containing them

1986
- 1986-08-14 GR GR862141A patent/GR862141B/el unknown
- 1986-08-14 KR KR1019860006686A patent/KR870002141A/ko not_active Withdrawn
- 1986-08-14 ES ES8601152A patent/ES2001094A6/es not_active Expired
- 1986-08-14 PT PT83201A patent/PT83201A/pt unknown
- 1986-08-15 DE DE8686306318T patent/DE3675846D1/de not_active Expired - Fee Related
- 1986-08-15 US US06/896,957 patent/US4857531A/en not_active Expired - Fee Related
- 1986-08-15 GB GB08619957A patent/GB2179349A/en not_active Withdrawn
- 1986-08-15 EP EP86306318A patent/EP0212956B1/en not_active Expired - Lifetime
- 1986-08-15 DK DK390986A patent/DK390986A/da not_active Application Discontinuation
- 1986-08-15 FI FI863322A patent/FI863322A7/fi not_active Application Discontinuation
- 1986-08-15 NZ NZ217220A patent/NZ217220A/xx unknown
- 1986-08-15 NO NO863309A patent/NO863309L/no unknown
- 1986-08-15 AU AU61503/86A patent/AU597266B2/en not_active Expired - Fee Related
- 1986-08-15 CN CN198686106214A patent/CN86106214A/zh active Pending
- 1986-08-15 IL IL79727A patent/IL79727A/xx unknown
- 1986-08-15 CA CA000516012A patent/CA1266863A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NZ217220A (en)	1989-10-27
NO863309D0 (no)	1986-08-15
EP0212956A1 (en)	1987-03-04
GB2179349A (en)	1987-03-04
ES2001094A6 (es)	1988-04-16
AU597266B2 (en)	1990-05-31
GR862141B (en)	1986-12-23
EP0212956B1 (en)	1990-11-28
GB8619957D0 (en)	1986-09-24
CA1266863A (en)	1990-03-20
FI863322L (fi)	1987-02-17
AU6150386A (en)	1987-02-19
DK390986D0 (da)	1986-08-15
DK390986A (da)	1987-02-17
FI863322A0 (fi)	1986-08-15
IL79727A (en)	1991-06-10
FI863322A7 (fi)	1987-02-17
PT83201A (en)	1986-09-01
CN86106214A (zh)	1987-04-22
DE3675846D1 (de)	1991-01-10
US4857531A (en)	1989-08-15
KR870002141A (ko)	1987-03-30

Publication	Publication Date	Title
NO863309L (no)	1987-02-17	Guaninderivater.
US5736549A (en)	1998-04-07	Hypoxanthine and guanine compounds
EP0159264B1 (en)	1991-07-24	Antiviral compounds
TW200843779A (en)	2008-11-16	Compounds
IL114492A (en)	2002-05-23	Benzimidazole derivatives, their preparation and pharmaceutical compositions containing them
JPS63297381A (ja)	1988-12-05	９−〔２−（ヒドロキシメチル）シクロアルキルメチル〕グアニン類
NO161116B (no)	1989-03-28	Analogifremgangsmaate for fremstilling av antiviralt virksomme purinderivater.
DE3901502A1 (de)	1989-07-27	Didesoxydehydrocarbocyclische nucleoside
NO172986B (no)	1993-06-28	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte 9h-puriner
SK14052003A3 (sk)	2004-07-07	Použitie derivátov adenozínu na prípravu liečiva na liečenie syndrómu inzulínovej rezistencie a diabetu
EP0366385B1 (en)	1993-06-09	Guanine derivatives having antiviral activity and their pharmaceutically acceptable salts
WO1999012927A1 (en)	1999-03-18	Purine acyclonucleosides as antiviral agents
EP0361831A1 (en)	1990-04-04	Antiviral nucleoside combination
OA10706A (en)	2001-05-08	2-Amino-5,6-dichlorobenzimidazole derivatives having antiviral activity.
CZ402791A3 (en)	1993-07-14	Cyclopentane derivatives and pharmaceutical composition in which they are comprised
US6306847B1 (en)	2001-10-23	Condensed purine derivatives
IE43780B1 (en)	1981-05-20	Piperidinoalkyl derivatives of purines
EP0521463A2 (de)	1993-01-07	Cyclisch substituierte Cycloalkyltriole, Verfahren und Zwischenprodukte zu ihrer Herstellung sowie ihre Verwendung als antivirale und antiparasitäre Mittel
US5100896A (en)	1992-03-31	Carbocyclic analogues of 7H-1,2,3-triazolo [4,5-d]pyrimidine furanosides
US4935427A (en)	1990-06-19	Pyrimidine and purine 1,2-butadiene-4-ols as anti-retroviral agents
DE3606634A1 (de)	1987-09-03	Isohexid-nucleoside, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5155112A (en)	1992-10-13	Cyclopentane derivatives
DE69122437T2 (de)	1997-03-13	Purinyl und Pyrimidinyltetrahydrofurane
JPS6284086A (ja)	1987-04-17	グアニン誘導体
WO1990009998A1 (de)	1990-09-07	Neue acyclische nucleosid-analoga, verfahren zu ihrer herstellung und verwendung dieser verbindungen als antivirale arzneimittel