LU87894A1 - Didesoxyinosine par desamination enzymatique de la didesoxyadenosine - Google Patents

Didesoxyinosine par desamination enzymatique de la didesoxyadenosine Download PDF

Info

Publication number: LU87894A1
Authority: LU; Luxembourg
Prior art keywords: radical; stage; formula; mixture; hydroxy
Prior art date: 1990-02-28

Application number

LU87894A

Other languages

English (en)

French (fr)

Inventor

Farina Vittorio

Daniel A Benigni

Paul R Brodfuehrer

Original Assignee

Squibb Bristol Myers Co

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.)

1990-02-28

Filing date

1991-02-27

Publication date

1991-12-16

1991-02-27 Application filed by Squibb Bristol Myers Co filed Critical Squibb Bristol Myers Co

1991-12-16 Publication of LU87894A1 publication Critical patent/LU87894A1/fr

Links

230000009615 deamination Effects 0.000 title claims description 10
238000006481 deamination reaction Methods 0.000 title claims description 10
230000002255 enzymatic effect Effects 0.000 title description 5
238000000034 method Methods 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
102000055025 Adenosine deaminases Human genes 0.000 claims description 20
230000008569 process Effects 0.000 claims description 16
101710169336 5'-deoxyadenosine deaminase Proteins 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 7
WVXRAFOPTSTNLL-RNFRBKRXSA-N [(2r,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@H](CO)O1 WVXRAFOPTSTNLL-RNFRBKRXSA-N 0.000 claims description 4
229960002656 didanosine Drugs 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
238000012544 monitoring process Methods 0.000 claims 1
150000003254 radicals Chemical class 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
-1 carbonyl radical Chemical class 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 9
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 5
229930010555 Inosine Natural products 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
229960003786 inosine Drugs 0.000 description 5
239000003921 oil Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
229930024421 Adenine Natural products 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229960000643 adenine Drugs 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000002126 C01EB10 - Adenosine Substances 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
229960005305 adenosine Drugs 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
HXJFQNUWPUICNY-UHFFFAOYSA-N disiamylborane Chemical compound CC(C)C(C)BC(C)C(C)C HXJFQNUWPUICNY-UHFFFAOYSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
229910010082 LiAlH Inorganic materials 0.000 description 2
IJJVVYKWKYVQFW-UHFFFAOYSA-N N,N-disilyl-7H-purin-6-amine Chemical compound [SiH3]N(C1=C2NC=NC2=NC=N1)[SiH3] IJJVVYKWKYVQFW-UHFFFAOYSA-N 0.000 description 2
101710110363 Putative adenosine/adenine deaminase Proteins 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
239000012190 activator Substances 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004691 alkyl thio carbonyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000005129 aryl carbonyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 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
239000012267 brine Substances 0.000 description 2
244000309466 calf Species 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
125000003835 nucleoside group Chemical group 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
150000003212 purines Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
210000000952 spleen Anatomy 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
QVADRSWDTZDDGR-GSVOUGTGSA-N (2r)-5-oxooxolane-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCC(=O)O1 QVADRSWDTZDDGR-GSVOUGTGSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
FCZOVUJWOBSMSS-UHFFFAOYSA-N 5-[(6-aminopurin-9-yl)methyl]-5-methyl-3-methylideneoxolan-2-one Chemical class C1=NC2=C(N)N=CN=C2N1CC1(C)CC(=C)C(=O)O1 FCZOVUJWOBSMSS-UHFFFAOYSA-N 0.000 description 1
QVADRSWDTZDDGR-UHFFFAOYSA-N 5-oxotetrahydrofuran-2-carboxylic acid Chemical compound OC(=O)C1CCC(=O)O1 QVADRSWDTZDDGR-UHFFFAOYSA-N 0.000 description 1
BXZVVICBKDXVGW-RNFRBKRXSA-N 9-[(2r,5r)-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound O1[C@@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-RNFRBKRXSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HNESBGWMHRLOIO-QWHCGFSZSA-N [(2s,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate Chemical compound C([C@@H]1CC[C@@H](O1)N1C=2N=CN=C(C=2N=C1)N)OC(=O)C1=CC=CC=C1 HNESBGWMHRLOIO-QWHCGFSZSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000006480 benzoylation reaction Methods 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
238000006206 glycosylation reaction Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical class O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000006225 natural substrate Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
238000005192 partition Methods 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
125000005106 triarylsilyl group Chemical group 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Zoology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU87894A 1990-02-28 1991-02-27 Didesoxyinosine par desamination enzymatique de la didesoxyadenosine LU87894A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US48670190		1990-02-28
US07/486,701 US5011774A (en)	1987-07-17	1990-02-28	Dideoxyinosine by enzymatic deamination of dideoxyadenosine

Publications (1)

Publication Number	Publication Date
LU87894A1 true LU87894A1 (fr)	1991-12-16

Family

ID=23932926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87894A LU87894A1 (fr)	1990-02-28	1991-02-27	Didesoxyinosine par desamination enzymatique de la didesoxyadenosine

Country Status (3)

Country	Link
US (1)	US5011774A (de)
AT (1)	AT400576B (de)
LU (1)	LU87894A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5827727A (en) *	1990-02-01	1998-10-27	Emory University	Method of resolution of 1,3-oxathiolane nucleoside enantiomers
US5204466A (en) *	1990-02-01	1993-04-20	Emory University	Method and compositions for the synthesis of bch-189 and related compounds
US5914331A (en) *	1990-02-01	1999-06-22	Emory University	Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US5276151A (en) *	1990-02-01	1994-01-04	Emory University	Method of synthesis of 1,3-dioxolane nucleosides
US5444063A (en) *	1990-12-05	1995-08-22	Emory University	Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
US5925643A (en) *	1990-12-05	1999-07-20	Emory University	Enantiomerically pure β-D-dioxolane-nucleosides
US6391859B1 (en)	1995-01-27	2002-05-21	Emory University	[5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides
US5703058A (en) *	1995-01-27	1997-12-30	Emory University	Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent
US20040175804A1 (en) *	2003-03-04	2004-09-09	Skonezny Paul M.	Process for preparing dideoxyinosine using adenosine deaminase enzyme
DE102013008875B4 (de) *	2013-05-27	2019-07-11	Asa Spezialenzyme Gmbh	Verfahren zum enzymatischen Purinabbau

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1058209B (de) *	1957-11-18	1959-05-27	It Prodotti Schering Soc	Verfahren zur Herstellung von reinem Inosin aus Adenosin mittels Adenosindeaminase
NZ216172A (en) *	1985-05-15	1989-08-29	Wellcome Found	Nucleosides and pharmaceutical compositions
US4835104A (en) *	1987-06-16	1989-05-30	Ajinomoto Co., Inc., Patent & Licensing Department	Process for producing and purifying 2',3'-dideoxynucleosides, and process for producing 2',3'-dideoxy-2',3'-didehydronucleosides

1990
- 1990-02-28 US US07/486,701 patent/US5011774A/en not_active Expired - Lifetime
1991
- 1991-02-27 AT AT0041091A patent/AT400576B/de not_active IP Right Cessation
- 1991-02-27 LU LU87894A patent/LU87894A1/fr unknown

Also Published As

Publication number	Publication date
ATA41091A (de)	1995-06-15
US5011774A (en)	1991-04-30
AT400576B (de)	1996-01-25

Publication	Publication Date	Title
EP0051023B1 (de)	1984-05-30	Derivate der Benzoyl- und alpha-Hydroxybenzyl-phenyl-osid-Familie, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0290321B1 (de)	1991-10-02	Beta-D-Phenyl-Thioxyloside, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
LU87894A1 (fr)	1991-12-16	Didesoxyinosine par desamination enzymatique de la didesoxyadenosine
EP0057491B1 (de)	1984-08-01	Halogenierte Derivate des 5-Hydroxy-tetrahydro-2-furanons
LU85841A1 (fr)	1985-12-16	Procede stereospecifique de preparation d'une acetoxyazetidinone
FR2474503A1 (fr)	1981-07-31	Composes intermediaires utiles pour l'obtention de la spectinomycine et de ses analogues ainsi que l'utilisation de ces produits
BE875054A (fr)	1979-07-16	Composes analogues aux cephalosporines
EP1252171B1 (de)	2007-08-15	Verfahren zur herstellung von funktionalisierten beta-(1,3)-glucanderivaten
LU87280A1 (fr)	1989-03-08	Didesoxyinosine par desamination enzymatique de la didesoxyadenosine
JPH0217199A (ja)	1990-01-22	２’−デオキシ−β−アデノシンの製造方法
EP1071692B1 (de)	2002-07-31	Verfahren zur synthese von laminaribiose
EP0082793B1 (de)	1989-05-10	Derivate mit einer Glucurolsäure-Struktur, ihre Herstellung und ihre biologischen Verwendungen
CH670825A5 (de)	1989-07-14
EP0153212B1 (de)	1988-07-13	4,4-Dimethyl-Tetrahydro-2H-Pyran-2-on-Derivate, Verfahren zu deren Herstellung und deren Verwendung für die Synthese von cyclopropanischen Derivaten
BE887456R (fr)	1981-08-10	Procede de production de composes intermediaires pour l'obtention de la spectinomycine et de ses analogues et produits de ce procede
CA2196102A1 (fr)	1996-02-15	Derives de streptogramine, leur preparation et les compositions pharmaceutiques qui les contiennent
US20030153745A1 (en)	2003-08-14	Process for producing nucleic acid derivative
CA1084907A (fr)	1980-09-02	Derives de la cephalosporine, leur preparation et les compositions qui les contiennent
EP1165582B1 (de)	2003-01-15	Neues verfahren zur herstellung von etoposid
BE892370A (fr)	1982-07-01	Nouveau procede de preparation de derives de la penicilline et de la cephalosporine
FR2460953A1 (fr)	1981-01-30	Nouveau procede de preparation d'anomeres et de melanges asteriques de nouveaux analogues de spectinomycine
EP1165581B1 (de)	2003-01-15	Verfahren zur herstellung von epipodophyllotoxine-4'-demethyl-4'-phosphat-2",3"-bis pentafluorphenoxyacetyl-4",6"-ethyliden- beta-d-glucosid und seine salzen
EP0270124A2 (de)	1988-06-08	Cycloalkanderivate und diese enthaltende Antimagengeschwürzusammensetzungen
BE634644A (de)
FR2616431A1 (fr)	1988-12-16	Procede de preparation de derives de la (trans)-4-phenyl-l-proline