AP101A - Therapeutic Nucleosides - Google Patents
Therapeutic Nucleosides Download PDFInfo
- Publication number
- AP101A AP101A APAP/P/1989/000129A AP8900129A AP101A AP 101 A AP101 A AP 101A AP 8900129 A AP8900129 A AP 8900129A AP 101 A AP101 A AP 101A
- Authority
- AP
- ARIPO
- Prior art keywords
- alkyl
- substituted
- amino
- methanol
- compound
- Prior art date
Links
- 239000002777 nucleoside Substances 0.000 title abstract description 5
- 125000003835 nucleoside group Chemical group 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 208000015181 infectious disease Diseases 0.000 claims abstract description 12
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000013160 medical therapy Methods 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000004480 active ingredient Substances 0.000 claims description 45
- -1 imidazolylthio group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000004149 thio group Chemical group *S* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 208000031886 HIV Infections Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- PWFXLXMPGSLEOZ-UHFFFAOYSA-N precursor Z Chemical group O1C2COP(O)(=O)OC2C(=O)C2C1NC(N=C(NC1=O)N)=C1N2 PWFXLXMPGSLEOZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 126
- 239000000243 solution Substances 0.000 description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 61
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- 239000000741 silica gel Substances 0.000 description 54
- 229910002027 silica gel Inorganic materials 0.000 description 54
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 44
- 238000009472 formulation Methods 0.000 description 40
- 239000000843 powder Substances 0.000 description 38
- 229910001868 water Inorganic materials 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 239000003921 oil Substances 0.000 description 28
- 238000002425 crystallisation Methods 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- IHEDZPMXLKYPSA-RQJHMYQMSA-N [(1s,4r)-4-(2-amino-6-chloropurin-9-yl)cyclopent-2-en-1-yl]methanol Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1[C@@H]1C[C@H](CO)C=C1 IHEDZPMXLKYPSA-RQJHMYQMSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000010828 elution Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 208000030507 AIDS Diseases 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 241000700721 Hepatitis B virus Species 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
- 241000725303 Human immunodeficiency virus Species 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 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 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229940069328 povidone Drugs 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000002026 chloroform extract Substances 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000004533 oil dispersion Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 6
- 229940073584 methylene chloride Drugs 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 5
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- 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
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
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- 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
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB888815265A GB8815265D0 (en) | 1988-06-27 | 1988-06-27 | Therapeutic nucleosides |
Publications (2)
Publication Number | Publication Date |
---|---|
AP8900129A0 AP8900129A0 (en) | 1989-07-31 |
AP101A true AP101A (en) | 1990-10-23 |
Family
ID=10639435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1989/000129A AP101A (en) | 1988-06-27 | 1989-06-26 | Therapeutic Nucleosides |
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US (5) | US5034394A (cs) |
EP (1) | EP0349242B1 (cs) |
JP (3) | JP2875814B2 (cs) |
KR (1) | KR0140532B1 (cs) |
AP (1) | AP101A (cs) |
AT (1) | ATE120194T1 (cs) |
AU (1) | AU636108B2 (cs) |
CA (1) | CA1340589C (cs) |
CY (1) | CY2018A (cs) |
CZ (1) | CZ283786B6 (cs) |
DE (1) | DE68921798T2 (cs) |
DK (1) | DK174668B1 (cs) |
ES (1) | ES2069582T3 (cs) |
FI (2) | FI893113A (cs) |
GB (1) | GB8815265D0 (cs) |
GR (1) | GR3015966T3 (cs) |
HK (1) | HK85897A (cs) |
HU (2) | HU206353B (cs) |
IE (1) | IE68038B1 (cs) |
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LV (1) | LV5781B4 (cs) |
MY (1) | MY104043A (cs) |
NZ (1) | NZ229716A (cs) |
PT (1) | PT90973B (cs) |
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ZA (1) | ZA894837B (cs) |
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DE3148363A1 (de) * | 1980-12-12 | 1982-09-16 | Toyo Jozo K.K., Shizuoka | Neplanocin a-derivate |
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 |
PT83201A (en) * | 1985-08-16 | 1986-09-01 | Glaxo Group Ltd | Guanine derivatives |
JPS62177234A (ja) * | 1986-01-30 | 1987-08-04 | Mitsubishi Heavy Ind Ltd | 遠心紡糸によるカ−ボン繊維の製造装置 |
IN164556B (cs) * | 1986-03-06 | 1989-04-08 | Takeda Chemical Industries Ltd | |
US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
JPS6422853A (en) * | 1987-07-17 | 1989-01-25 | Asahi Glass Co Ltd | Nucleoside analog |
US4916224A (en) * | 1988-01-20 | 1990-04-10 | Regents Of The University Of Minnesota | Dideoxycarbocyclic nucleosides |
US4950758A (en) * | 1988-01-20 | 1990-08-21 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
IT1229531B (it) * | 1988-01-20 | 1991-09-04 | Univ Minnesota | Composti nucleosidi dideossidideidrocarbociclici e formulazione farmaceutica che li contiene |
US4787554A (en) * | 1988-02-01 | 1988-11-29 | Honeywell Inc. | Firing rate control system for a fuel burner |
GB8808458D0 (en) * | 1988-04-11 | 1988-05-11 | Metal Box Plc | Food containers |
NZ229453A (en) * | 1988-06-10 | 1991-08-27 | Univ Minnesota & Southern Rese | A pharmaceutical composition containing purine derivatives with nucleosides such as azt, as antiviral agents |
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 |
DE69016739T2 (de) * | 1989-10-16 | 1995-06-14 | Chiroscience Ltd | Chirale Azabicycloheptanone und Verfahren zu ihrer Herstellung. |
US5126452A (en) * | 1990-04-06 | 1992-06-30 | Glaxo Inc. | Synthesis of purine substituted cyclopentene derivatives |
-
1988
- 1988-06-27 GB GB888815265A patent/GB8815265D0/en active Pending
-
1989
- 1989-06-23 CA CA000603768A patent/CA1340589C/en not_active Expired - Lifetime
- 1989-06-26 IE IE206189A patent/IE68038B1/en not_active IP Right Cessation
- 1989-06-26 AU AU37025/89A patent/AU636108B2/en not_active Expired
- 1989-06-26 AT AT89306467T patent/ATE120194T1/de not_active IP Right Cessation
- 1989-06-26 JP JP1163629A patent/JP2875814B2/ja not_active Expired - Lifetime
- 1989-06-26 EP EP89306467A patent/EP0349242B1/en not_active Expired - Lifetime
- 1989-06-26 MY MYPI89000860A patent/MY104043A/en unknown
- 1989-06-26 DE DE68921798T patent/DE68921798T2/de not_active Expired - Lifetime
- 1989-06-26 FI FI893113A patent/FI893113A/fi not_active Application Discontinuation
- 1989-06-26 HU HU893215A patent/HU206353B/hu unknown
- 1989-06-26 IL IL9075289A patent/IL90752A/en not_active IP Right Cessation
- 1989-06-26 ZA ZA894837A patent/ZA894837B/xx unknown
- 1989-06-26 AP APAP/P/1989/000129A patent/AP101A/en active
- 1989-06-26 ES ES89306467T patent/ES2069582T3/es not_active Expired - Lifetime
- 1989-06-26 PT PT90973A patent/PT90973B/pt not_active IP Right Cessation
- 1989-06-26 NZ NZ229716A patent/NZ229716A/en unknown
- 1989-06-26 DK DK198903156A patent/DK174668B1/da not_active IP Right Cessation
- 1989-09-26 KR KR1019890013812A patent/KR0140532B1/ko not_active IP Right Cessation
- 1989-09-26 FI FI894545A patent/FI102680B1/fi active IP Right Grant
- 1989-12-22 US US07/455,201 patent/US5034394A/en not_active Expired - Lifetime
- 1989-12-22 US US07/455,538 patent/US5049671A/en not_active Expired - Lifetime
-
1990
- 1990-12-19 US US07/630,129 patent/US5087697A/en not_active Expired - Lifetime
- 1990-12-21 JP JP2419050A patent/JP2963775B2/ja not_active Expired - Lifetime
- 1990-12-21 CZ CS922470A patent/CZ283786B6/cs not_active IP Right Cessation
- 1990-12-21 UA UA5011830A patent/UA29382C2/uk unknown
-
1991
- 1991-05-08 US US07/697,260 patent/US5089500A/en not_active Expired - Lifetime
- 1991-09-27 US US07/767,134 patent/US5206435A/en not_active Expired - Lifetime
-
1995
- 1995-04-28 GR GR950401089T patent/GR3015966T3/el unknown
- 1995-06-20 HU HU95P/P00288P patent/HU211537A9/hu unknown
-
1996
- 1996-07-16 LV LV960240A patent/LV5781B4/xx unknown
-
1997
- 1997-06-19 HK HK85897A patent/HK85897A/xx not_active IP Right Cessation
-
1998
- 1998-02-20 CY CY201898A patent/CY2018A/xx unknown
- 1998-09-14 JP JP10259574A patent/JPH11139976A/ja active Pending
Patent Citations (4)
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US4859677A (en) * | 1987-04-17 | 1989-08-22 | University Of Kansas | Nucleoside analogues having antiviral activity |
EP0325460A1 (en) * | 1988-01-20 | 1989-07-26 | The Regents Of The University Of Minnesota | Dideoxydidehydrocarbocyclic nucleosides |
EP0338842A1 (en) * | 1988-04-22 | 1989-10-25 | Schering Corporation | Cyclopentyl purine derivatives, intermediates and processes for preparation |
EP0347852A2 (en) * | 1988-06-20 | 1989-12-27 | Merrell Dow Pharmaceuticals Inc. | Novel neplanocin derivatives |
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