PH27154A - Substituted 9H-purines - Google Patents

Substituted 9H-purines Download PDF

Info

Publication number: PH27154A
Authority: PH; Philippines
Prior art keywords: alkylamino; amino; purine; compound according; acceptable salt
Prior art date: 1988-10-06

Application number

PH39332A

Other languages

English (en)

Inventor

Hans Allgeier

Original Assignee

Ciba Geigy Ag

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.)

1988-10-06

Filing date

1989-10-04

Publication date

1993-04-02

1989-10-04 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1993-04-02 Publication of PH27154A publication Critical patent/PH27154A/en

Links

KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title claims description 33
150000001875 compounds Chemical class 0.000 claims description 104
150000003839 salts Chemical class 0.000 claims description 70
238000000034 method Methods 0.000 claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
125000003282 alkyl amino group Chemical group 0.000 claims description 40
-1 2,6-difluorophenyl Chemical group 0.000 claims description 37
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 12
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 3
230000036461 convulsion Effects 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
206010015037 epilepsy Diseases 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
101000841210 Xenopus laevis Endothelin-3 receptor Proteins 0.000 claims 1
230000002082 anti-convulsion Effects 0.000 claims 1
125000004212 difluorophenyl group Chemical group 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
238000000675 plasmon resonance energy transfer Methods 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 38
239000002253 acid Substances 0.000 description 37
125000000217 alkyl group Chemical group 0.000 description 34
230000008569 process Effects 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
239000000460 chlorine Substances 0.000 description 19
150000001412 amines Chemical class 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 18
238000010438 heat treatment Methods 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
229910052801 chlorine Inorganic materials 0.000 description 16
125000003545 alkoxy group Chemical group 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
125000004356 hydroxy functional group Chemical group O* 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
125000002252 acyl group Chemical group 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000003701 inert diluent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000003826 tablet Substances 0.000 description 6
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 5
150000007513 acids Chemical class 0.000 description 5
150000003973 alkyl amines Chemical class 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000001841 imino group Chemical group [H]N=* 0.000 description 5
239000008101 lactose Substances 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
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 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000009471 action Effects 0.000 description 4
125000005236 alkanoylamino group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
102000006835 Lamins Human genes 0.000 description 3
108010047294 Lamins Proteins 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
210000005053 lamin Anatomy 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
241001214257 Mene Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000007941 film coated tablet Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
125000004175 fluorobenzyl group Chemical group 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000004576 sand Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 description 1
YDIKCZBMBPOGFT-DIONPBRTSA-N (2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride Chemical compound [Cl-].COC1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 YDIKCZBMBPOGFT-DIONPBRTSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 1
PUXJKAXYRIPWJM-UHFFFAOYSA-N 2,9-dichloropurine Chemical compound ClN1C2=NC(=NC=C2N=C1)Cl PUXJKAXYRIPWJM-UHFFFAOYSA-N 0.000 description 1
SZCDZAJCELOECB-UHFFFAOYSA-N 2-chloro-9-[(2-chlorophenyl)methyl]purine Chemical compound ClC1=CC=CC=C1CN1C2=NC(Cl)=NC=C2N=C1 SZCDZAJCELOECB-UHFFFAOYSA-N 0.000 description 1
BJAYANZFEQNNDV-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-7h-purin-6-amine Chemical compound CN(C)C1=NC(Cl)=NC2=C1NC=N2 BJAYANZFEQNNDV-UHFFFAOYSA-N 0.000 description 1
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150000003624 transition metals Chemical class 0.000 description 1
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
239000005052 trichlorosilane Substances 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
238000009736 wetting Methods 0.000 description 1
229940075420 xanthine Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

PH39332A 1988-10-06 1989-10-04 Substituted 9H-purines PH27154A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH373188		1988-10-06

Publications (1)

Publication Number	Publication Date
PH27154A true PH27154A (en)	1993-04-02

Family

ID=4262288

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39332A PH27154A (en)	1988-10-06	1989-10-04	Substituted 9H-purines

Country Status (17)

Country	Link
US (1)	US5110818A (fr)
EP (1)	EP0363320A3 (fr)
JP (1)	JPH02157279A (fr)
KR (1)	KR900006337A (fr)
AU (1)	AU632763B2 (fr)
CA (1)	CA2000154A1 (fr)
DD (1)	DD297820A5 (fr)
DK (1)	DK491389A (fr)
FI (1)	FI894707A7 (fr)
HU (1)	HUT52502A (fr)
IL (1)	IL91818A (fr)
MX (1)	MX17846A (fr)
NO (1)	NO172986C (fr)
NZ (1)	NZ230898A (fr)
PH (1)	PH27154A (fr)
PT (1)	PT91895B (fr)
ZA (1)	ZA897587B (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5391739A (en) *	1989-03-29	1995-02-21	Merrell Dow Pharmaceuticals Inc.	Selective adenosine receptor agents
US5387684A (en) *	1992-03-25	1995-02-07	The Green Cross Corporation	Isoindazole compound
FR2699176B1 (fr) *	1992-12-11	1995-03-03	Adir	Nouveaux composés bicycliques de pyrimidine, leur procédé de préparation et les compositions pharmaceutiques les renfermant.
GB9312853D0 (en) *	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5994361A (en) *	1994-06-22	1999-11-30	Biochem Pharma	Substituted purinyl derivatives with immunomodulating activity
US5591776A (en) *	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5922751A (en) *	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
DE19535504A1 (de) *	1995-09-25	1997-03-27	Bayer Ag	Substituierte Xanthine
US6166041A (en) *	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
FR2741881B1 (fr) *	1995-12-01	1999-07-30	Centre Nat Rech Scient	Nouveaux derives de purine possedant notamment des prorietes anti-proliferatives et leurs applications biologiques
US6075016A (en) *	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US6294541B1 (en)	1996-06-06	2001-09-25	Euro-Celtique S.A.	Purine derivatives having phosphodiesterase IV inhibition activity
US5864037A (en)	1996-06-06	1999-01-26	Euro-Celtique, S.A.	Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
CN1294590A (zh)	1997-12-12	2001-05-09	欧罗赛铁克股份有限公司	通过2－硫代黄嘌呤制备3－取代腺嘌呤的方法
US6319928B1 (en)	1998-11-30	2001-11-20	Euro-Celtique, S.A.	Purine derivatives having phosphodiesterase IV inhibition activity
CA2367143A1 (fr)	1999-04-02	2000-10-12	Euro-Celtique S.A.	Derives de purine possedant une activite d'inhibition de la phosphodiesterase iv
US7439359B2 (en) *	2000-11-02	2008-10-21	Sloan-Kettering Institute For Cancer Research	Small molecule compositions for binding to hsp90
WO2003037860A2 (fr) *	2001-10-30	2003-05-08	Conforma Therapeutics Corporation	Analogues de purine presentant une activite inhibitrice de hsp90
US20070129334A1 (en) *	2001-10-30	2007-06-07	Conforma Therapeutics Corporation	Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
MXPA06002997A (es) *	2003-09-18	2007-02-08	Conforma Therapeutics Corp	Novedosos compuestos heterociclicos como inhibidores- hsp90.
AU2006230447A1 (en)	2005-03-30	2006-10-05	Conforma Therapeutics Corporation	Alkynyl pyrrolopyrimidines and related analogs as HSP90-inhibitors
WO2007035963A2 (fr) *	2005-09-23	2007-03-29	Conforma Therapeutics Corporation	Methodes antitumorales dans lesquelles sont utilises des inhibiteurs de hsp90 de synthese independants de la multiresistance aux medicaments
WO2009034386A1 (fr) *	2007-09-13	2009-03-19	Astrazeneca Ab	Dérivés de l'adénine et de la 8-aza-adénine et leurs utilisations

Family Cites Families (10)

* Cited by examiner, † Cited by third party
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
GB1534163A (en) *	1976-07-28	1978-11-29	Merck & Co Inc	Adenine derivatives
USRE31429E (en) *	1977-02-14	1983-10-25	Merck & Co., Inc.	Process for preparation of 9-(dihalobenzyl)adenines
GB1547214A (en) *	1977-08-09	1979-06-06	Merck & Co Inc	Purine derivatives
US4189485A (en) *	1977-08-23	1980-02-19	Takeda Chemical Industries, Ltd.	Purine derivatives
US4361699A (en) *	1981-09-28	1982-11-30	Merck & Co., Inc.	Novel process for the preparation of N6 -alkyl-arprinocid
EP0108285B1 (fr) *	1982-10-14	1988-04-20	The Wellcome Foundation Limited	Dérivés de purine antiviraux
US4748177A (en) *	1984-03-26	1988-05-31	Warner-Lambert Company	Guanine derivatives
GB8408615D0 (en) *	1984-04-04	1984-05-16	Wellcome Found	Heterocyclic compounds
KR910700253A (ko) *	1989-01-31	1991-03-14	로버트 제이, 바란	N_6-치환-9-메틸아데닌: 신규한 부류의 아데노신 수용체 길항질

1989
- 1989-09-26 EP EP19890810731 patent/EP0363320A3/fr not_active Withdrawn
- 1989-09-28 IL IL9181889A patent/IL91818A/en not_active IP Right Cessation
- 1989-10-04 DD DD89333303A patent/DD297820A5/de not_active IP Right Cessation
- 1989-10-04 PT PT91895A patent/PT91895B/pt not_active IP Right Cessation
- 1989-10-04 PH PH39332A patent/PH27154A/en unknown
- 1989-10-04 NZ NZ230898A patent/NZ230898A/xx unknown
- 1989-10-04 CA CA002000154A patent/CA2000154A1/fr not_active Abandoned
- 1989-10-04 FI FI894707A patent/FI894707A7/fi not_active IP Right Cessation
- 1989-10-05 ZA ZA897587A patent/ZA897587B/xx unknown
- 1989-10-05 DK DK491389A patent/DK491389A/da not_active Application Discontinuation
- 1989-10-05 MX MX17846A patent/MX17846A/es unknown
- 1989-10-05 AU AU42612/89A patent/AU632763B2/en not_active Ceased
- 1989-10-05 JP JP1258944A patent/JPH02157279A/ja active Pending
- 1989-10-05 HU HU895224A patent/HUT52502A/hu unknown
- 1989-10-05 NO NO893965A patent/NO172986C/no unknown
- 1989-10-06 KR KR1019890014356A patent/KR900006337A/ko not_active Withdrawn
1990
- 1990-12-19 US US07/630,401 patent/US5110818A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL91818A0 (en)	1990-06-10
CA2000154A1 (fr)	1990-04-06
EP0363320A3 (fr)	1991-11-21
JPH02157279A (ja)	1990-06-18
IL91818A (en)	1994-08-26
PT91895A (pt)	1990-04-30
DK491389D0 (da)	1989-10-05
FI894707A0 (fi)	1989-10-04
DK491389A (da)	1990-04-07
PT91895B (pt)	1995-05-31
NO893965D0 (no)	1989-10-05
NO893965L (no)	1990-04-09
AU632763B2 (en)	1993-01-14
KR900006337A (ko)	1990-05-07
FI894707A7 (fi)	1990-04-07
NZ230898A (en)	1992-12-23
ZA897587B (en)	1990-05-30
MX17846A (es)	1994-03-31
NO172986B (no)	1993-06-28
US5110818A (en)	1992-05-05
AU4261289A (en)	1990-04-12
DD297820A5 (de)	1992-01-23
HUT52502A (en)	1990-07-28
NO172986C (no)	1993-10-06
EP0363320A2 (fr)	1990-04-11

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