PT99042A - Processo para a preparacao de purinas substituidas e de composicoes farmaceeuticas que as contem - Google Patents

Processo para a preparacao de purinas substituidas e de composicoes farmaceeuticas que as contem Download PDF

Info

Publication number: PT99042A
Authority: PT; Portugal
Prior art keywords: group; radical; compound; formula; oxo
Prior art date: 1990-09-26

Application number

PT99042A

Other languages

English (en)

Portuguese (pt)

Inventor

James Leroy Kelley

James Andrew Linneed Williams

Original Assignee

Wellcome Found

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.)

1990-09-26

Filing date

1991-09-25

Publication date

1992-08-31

1991-09-25 Application filed by Wellcome Found filed Critical Wellcome Found

1992-08-31 Publication of PT99042A publication Critical patent/PT99042A/pt

Links

238000002360 preparation method Methods 0.000 title claims description 71
238000000034 method Methods 0.000 title claims description 63
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 101
-1 (3 - ((2-amino-1,6-dihydro-6-oxo-9 H -purin-9-yl) -ethyl) -benzyl) -methyl-phosphonic acid Chemical compound 0.000 claims description 86
239000004480 active ingredient Substances 0.000 claims description 26
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000004043 oxo group Chemical group O=* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 3
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 309
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 258
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 157
239000000203 mixture Substances 0.000 description 72
239000003921 oil Substances 0.000 description 64
239000000243 solution Substances 0.000 description 64
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
235000019198 oils Nutrition 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
239000007787 solid Substances 0.000 description 43
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 36
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
238000009472 formulation Methods 0.000 description 28
150000003254 radicals Chemical class 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
238000002390 rotary evaporation Methods 0.000 description 20
239000000872 buffer Substances 0.000 description 18
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000000706 filtrate Substances 0.000 description 16
239000000460 chlorine Substances 0.000 description 15
238000005342 ion exchange Methods 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 12
102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 10
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 10
101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 9
239000002585 base Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
229920002554 vinyl polymer Polymers 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
230000036961 partial effect Effects 0.000 description 7
239000012258 stirred mixture Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000000356 contaminant Substances 0.000 description 6
239000006071 cream Substances 0.000 description 6
239000008367 deionised water Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000003039 volatile agent Substances 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000003925 fat Substances 0.000 description 5
235000019197 fats Nutrition 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000003826 tablet Substances 0.000 description 5
SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
101001066878 Homo sapiens Polyribonucleotide nucleotidyltransferase 1, mitochondrial Proteins 0.000 description 4
102100034410 Polyribonucleotide nucleotidyltransferase 1, mitochondrial Human genes 0.000 description 4
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000013256 coordination polymer Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
UAXIBJPHBMEGSP-UHFFFAOYSA-N di(propan-2-yloxy)phosphorylmethanol Chemical compound CC(C)OP(=O)(CO)OC(C)C UAXIBJPHBMEGSP-UHFFFAOYSA-N 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
239000008215 water for injection Substances 0.000 description 4
DREPONDJUKIQLX-UHFFFAOYSA-N 1-[ethenyl(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(=O)(C=C)OCC DREPONDJUKIQLX-UHFFFAOYSA-N 0.000 description 3
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
PSDUSPXRURGFFD-UHFFFAOYSA-N 9-[[3-(chloromethyl)phenyl]methyl]-6-(2-methoxyethoxy)purin-2-amine Chemical compound C1=NC=2C(OCCOC)=NC(N)=NC=2N1CC1=CC=CC(CCl)=C1 PSDUSPXRURGFFD-UHFFFAOYSA-N 0.000 description 3
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
201000005569 Gout Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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239000006227 byproduct Substances 0.000 description 3
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238000000465 moulding Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000012265 solid product Substances 0.000 description 3
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125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
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PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229940078545 isocetyl stearate Drugs 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
229940074928 isopropyl myristate Drugs 0.000 description 1
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
230000000366 juvenile effect Effects 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
DWHMMGGJCLDORC-UHFFFAOYSA-N methoxy(methyl)phosphinic acid Chemical compound COP(C)(O)=O DWHMMGGJCLDORC-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
235000019837 monoammonium phosphate Nutrition 0.000 description 1
229940043348 myristyl alcohol Drugs 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
QVZZOQYGVUGLSI-UHFFFAOYSA-N n,n-dimethylformamide;formamide Chemical compound NC=O.CN(C)C=O QVZZOQYGVUGLSI-UHFFFAOYSA-N 0.000 description 1
QSKQXHZJLUADLL-UHFFFAOYSA-N n-[3-[(2-amino-6-chloropurin-9-yl)methyl]phenyl]-2-di(propan-2-yloxy)phosphorylacetamide Chemical compound CC(C)OP(=O)(OC(C)C)CC(=O)NC1=CC=CC(CN2C3=NC(N)=NC(Cl)=C3N=C2)=C1 QSKQXHZJLUADLL-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
210000002445 nipple Anatomy 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
GUWZGMWHDAJAOC-UHFFFAOYSA-N oxoplatinum;hydrate Chemical compound O.[Pt]=O GUWZGMWHDAJAOC-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000008251 pharmaceutical emulsion Substances 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
208000001917 purine nucleoside phosphorylase deficiency Diseases 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
RLEILGCPRGJZND-UHFFFAOYSA-N s-(bromomethyl) ethanethioate Chemical compound CC(=O)SCBr RLEILGCPRGJZND-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
159000000000 sodium salts Chemical class 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960004016 sucrose syrup Drugs 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Obesity (AREA)
Biochemistry (AREA)
Hematology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PT99042A 1990-09-26 1991-09-25 Processo para a preparacao de purinas substituidas e de composicoes farmaceeuticas que as contem PT99042A (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909020931A GB9020931D0 (en)	1990-09-26	1990-09-26	Heterocyclic compounds

Publications (1)

Publication Number	Publication Date
PT99042A true PT99042A (pt)	1992-08-31

Family

ID=10682771

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT99042A PT99042A (pt)	1990-09-26	1991-09-25	Processo para a preparacao de purinas substituidas e de composicoes farmaceeuticas que as contem

Country Status (9)

Country	Link
EP (1)	EP0550574A1 (ja)
JP (1)	JPH06501253A (ja)
AU (1)	AU8542991A (ja)
GB (1)	GB9020931D0 (ja)
IE (1)	IE913360A1 (ja)
IL (1)	IL99561A0 (ja)
PT (1)	PT99042A (ja)
WO (1)	WO1992005180A1 (ja)
ZA (1)	ZA917666B (ja)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5502187A (en) *	1992-04-03	1996-03-26	The Upjohn Company	Pharmaceutically active bicyclic-heterocyclic amines
US5663175A (en) *	1994-12-09	1997-09-02	Merck & Co. Inc.	Prodrugs of herpes TK inhibitors
US6020475A (en) *	1998-02-10	2000-02-01	Isis Pharmeuticals, Inc.	Process for the synthesis of oligomeric compounds
WO2003037860A2 (en)	2001-10-30	2003-05-08	Conforma Therapeutics Corporation	Purine analogs having hsp90-inhibiting activity
MXPA06002997A (es)	2003-09-18	2007-02-08	Conforma Therapeutics Corp	Novedosos compuestos heterociclicos como inhibidores- hsp90.
WO2006115509A2 (en)	2004-06-24	2006-11-02	Novartis Vaccines And Diagnostics Inc.	Small molecule immunopotentiators and assays for their detection
AU2006230447A1 (en)	2005-03-30	2006-10-05	Conforma Therapeutics Corporation	Alkynyl pyrrolopyrimidines and related analogs as HSP90-inhibitors
US20080008682A1 (en)	2006-07-07	2008-01-10	Chong Lee S	Modulators of toll-like receptor 7
HRP20210927T1 (hr) *	2014-08-15	2021-09-03	Chia Tai Tianqing Pharmaceutical Group Co., Ltd.	Spojevi pirolopirimidina koje se koriste kao agonist tlr7
ES2960987T3 (es)	2019-04-12	2024-03-07	Riboscience Llc	Derivados de heteroarilo bicíclicos como inhibidores de la ectonucleótido pirofosfatasa fosfodiesterasa 1

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3148363A1 (de) *	1980-12-12	1982-09-16	Toyo Jozo K.K., Shizuoka	Neplanocin a-derivate
EP0338887B1 (en) *	1988-04-19	1993-12-08	Merrell Dow Pharmaceuticals Inc.	Phosphonoalkylpurine derivatives

1990
- 1990-09-26 GB GB909020931A patent/GB9020931D0/en active Pending
1991
- 1991-09-25 AU AU85429/91A patent/AU8542991A/en not_active Abandoned
- 1991-09-25 IE IE336091A patent/IE913360A1/en unknown
- 1991-09-25 ZA ZA917666A patent/ZA917666B/xx unknown
- 1991-09-25 PT PT99042A patent/PT99042A/pt not_active Application Discontinuation
- 1991-09-25 JP JP3515547A patent/JPH06501253A/ja active Pending
- 1991-09-25 WO PCT/GB1991/001647 patent/WO1992005180A1/en not_active Ceased
- 1991-09-25 EP EP91917241A patent/EP0550574A1/en not_active Withdrawn
- 1991-09-25 IL IL99561A patent/IL99561A0/xx unknown

Also Published As

Publication number	Publication date
IL99561A0 (en)	1992-08-18
EP0550574A1 (en)	1993-07-14
ZA917666B (en)	1993-03-25
JPH06501253A (ja)	1994-02-10
IE913360A1 (en)	1992-04-08
GB9020931D0 (en)	1990-11-07
AU8542991A (en)	1992-04-15
WO1992005180A1 (en)	1992-04-02

Legal Events

Date	Code	Title	Description
1992-08-31	BB1A	Laying open of patent application	Effective date: 19920408
1999-02-26	FC3A	Refusal	Effective date: 19981111

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