DE2220246A1 - 1,2,4 Tnazol Nukleoside - Google Patents
1,2,4 Tnazol NukleosideInfo
- Publication number
- DE2220246A1 DE2220246A1 DE19722220246 DE2220246A DE2220246A1 DE 2220246 A1 DE2220246 A1 DE 2220246A1 DE 19722220246 DE19722220246 DE 19722220246 DE 2220246 A DE2220246 A DE 2220246A DE 2220246 A1 DE2220246 A1 DE 2220246A1
- Authority
- DE
- Germany
- Prior art keywords
- triazole
- compound
- ribofuranosyl
- phosphate
- carboxamide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 239000002777 nucleoside Substances 0.000 title description 14
- 125000003835 nucleoside group Chemical group 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910019142 PO4 Inorganic materials 0.000 claims description 32
- 239000010452 phosphate Substances 0.000 claims description 20
- 235000021317 phosphate Nutrition 0.000 claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UQSPFUMMCXCDLF-AFCXAGJDSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carbothioamide Chemical compound N1=C(C(=S)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 UQSPFUMMCXCDLF-AFCXAGJDSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 230000017105 transposition Effects 0.000 claims description 3
- UZAZHIXEGDBPKD-TXICZTDVSA-N 5-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-1,2,4-triazole-3-carboxamide Chemical compound N1C(C(=O)N)=NC([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 UZAZHIXEGDBPKD-TXICZTDVSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- IWUCXVSUMQZMFG-GUMKFJOWSA-N 1-[(2r,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-GUMKFJOWSA-N 0.000 claims 1
- PIGYMBULXKLTCJ-UHSSARMYSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboximidamide;hydrochloride Chemical compound Cl.N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 PIGYMBULXKLTCJ-UHSSARMYSA-N 0.000 claims 1
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 14
- 230000000840 anti-viral effect Effects 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000006188 syrup Substances 0.000 description 11
- 235000020357 syrup Nutrition 0.000 description 11
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 241000700605 Viruses Species 0.000 description 7
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QMPFMODFBNEYJH-UHFFFAOYSA-N methyl 1h-1,2,4-triazole-5-carboxylate Chemical compound COC(=O)C1=NC=NN1 QMPFMODFBNEYJH-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- -1 thiocarboxamido Chemical group 0.000 description 6
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003443 antiviral agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000004440 column chromatography Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000006884 silylation reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GUQHFZFTGHNVDG-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carbonitrile Chemical compound N#CC1=NC=NN1 GUQHFZFTGHNVDG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 238000007098 aminolysis reaction Methods 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- MHSVUSZEHNVFKW-UHFFFAOYSA-N bis-4-nitrophenyl phosphate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OP(=O)(O)OC1=CC=C([N+]([O-])=O)C=C1 MHSVUSZEHNVFKW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
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- 239000002773 nucleotide Substances 0.000 description 3
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- 230000026731 phosphorylation Effects 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YBBDIXWREGHZRM-DYXQDRAXSA-N (3s,4r,5r)-2-chloro-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane Chemical compound C([C@H]1OC([C@H]([C@@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)Cl)OCC1=CC=CC=C1 YBBDIXWREGHZRM-DYXQDRAXSA-N 0.000 description 2
- SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-UHFFFAOYSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- RFJYLFZDYHCYNF-UAKXSSHOSA-N methyl 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RFJYLFZDYHCYNF-UAKXSSHOSA-N 0.000 description 2
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- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
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- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- PUHIETBGRWTVIS-PMHJDTQVSA-N methyl 1-[(2r,3r,4r,5r)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1[C@H]1[C@H](OC(=O)C=2C=CC=CC=2)[C@H](OC(=O)C=2C=CC=CC=2)[C@@H](COC(=O)C=2C=CC=CC=2)O1 PUHIETBGRWTVIS-PMHJDTQVSA-N 0.000 description 1
- LLSQCRXJNSSQPO-UHFFFAOYSA-N methyl triazole-1-carboxylate Chemical compound COC(=O)N1C=CN=N1 LLSQCRXJNSSQPO-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XESARGFCSKSFID-FLLFQEBCSA-N pirazofurin Chemical compound OC1=C(C(=O)N)NN=C1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 XESARGFCSKSFID-FLLFQEBCSA-N 0.000 description 1
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- 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
- C07H19/056—Triazole or tetrazole radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14901771A | 1971-06-01 | 1971-06-01 | |
| US24025272A | 1972-03-31 | 1972-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2220246A1 true DE2220246A1 (de) | 1972-12-14 |
Family
ID=26846393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722220246 Withdrawn DE2220246A1 (de) | 1971-06-01 | 1972-04-25 | 1,2,4 Tnazol Nukleoside |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3798209A (enExample) |
| JP (5) | JPS5527076B1 (enExample) |
| AR (1) | AR199463A1 (enExample) |
| AU (1) | AU461900B2 (enExample) |
| BE (1) | BE784195A (enExample) |
| BG (1) | BG22827A3 (enExample) |
| CA (1) | CA997756A (enExample) |
| CH (1) | CH614452A5 (enExample) |
| DD (1) | DD99791A5 (enExample) |
| DE (1) | DE2220246A1 (enExample) |
| DK (2) | DK143069C (enExample) |
| EG (1) | EG11406A (enExample) |
| ES (1) | ES403142A1 (enExample) |
| FR (1) | FR2140126B1 (enExample) |
| GB (1) | GB1353565A (enExample) |
| HK (1) | HK23876A (enExample) |
| HU (1) | HU167614B (enExample) |
| IE (1) | IE36478B1 (enExample) |
| IL (1) | IL39416A (enExample) |
| IN (1) | IN142290B (enExample) |
| IS (1) | IS913B6 (enExample) |
| LU (1) | LU65446A1 (enExample) |
| MC (1) | MC921A1 (enExample) |
| MY (1) | MY7600203A (enExample) |
| NL (1) | NL7207156A (enExample) |
| NO (1) | NO138805C (enExample) |
| RO (1) | RO62435A (enExample) |
| SE (3) | SE405604B (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2511829A1 (de) * | 1974-03-18 | 1975-09-25 | Icn Pharmaceuticals | N-substituierte 1,2,4-triazole |
| DE2511828A1 (de) * | 1974-03-18 | 1975-10-02 | Icn Pharmaceuticals | 1-(beta-d-ribofuranosyl)-1,2,4-triazolsaeureester |
| US10508117B2 (en) | 2014-09-16 | 2019-12-17 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| US11110091B2 (en) | 2008-12-09 | 2021-09-07 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
| US11116774B2 (en) | 2014-07-11 | 2021-09-14 | Gilead Sciences, Inc. | Modulators of toll-like receptors for the treatment of HIV |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| US12611453B2 (en) | 2019-05-22 | 2026-04-28 | Gilead Sciences, Inc. | Method of inducing an HIV-1-specific immune response using a chimpanzee adenovirus vector encoding an hivacat t-cell immunogen and TLR7 agonist |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984396A (en) * | 1971-06-01 | 1976-10-05 | Icn Pharmaceuticals, Inc. | 1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters |
| DE2401449A1 (de) * | 1973-01-16 | 1974-07-25 | Voorhees | Pharmazeutische zusammensetzung zur linderung von hautproliferationserkrankungen |
| US3888843A (en) * | 1973-06-12 | 1975-06-10 | Toyo Jozo Kk | 4-carbamoyl-1-' -d-ribofuranosylimidazolium-5-olate |
| US3960836A (en) * | 1974-07-22 | 1976-06-01 | Eli Lilly And Company | Acylated derivatives of pyrazofurin and process for their preparation |
| US4007198A (en) * | 1975-05-01 | 1977-02-08 | American Cyanamid Company | Substituted 1,2,4-triazole carboxamide |
| US4138547A (en) * | 1977-12-22 | 1979-02-06 | Icn Pharmaceuticals, Inc. | Process for preparing 1,2,4-triazole nucleosides |
| JPS57146593A (en) * | 1981-03-09 | 1982-09-10 | Ajinomoto Co Inc | Preparation of ribofuranosyltriazole derivative |
| US4451648A (en) * | 1981-08-19 | 1984-05-29 | The United States Of America As Represented By The Department Of Health And Human Services | Process for the production of 2-β-D-ribofuranosylthiazole-4-carboxamide |
| US4531001A (en) * | 1982-03-23 | 1985-07-23 | Brigham Young University | 2-β-D-ribofuranosylselenazole-4-carboxamide compounds |
| US4446315A (en) * | 1982-09-24 | 1984-05-01 | The United States Of America As Represented By The Department Of Health And Human Services | Adenosine 5'-triphosphate-4-carboxamide-ribofuranosylthiazole |
| JPS5964648U (ja) * | 1982-10-22 | 1984-04-28 | 阿波野 政晴 | 日覆用骨格 |
| BE902199A (fr) * | 1984-10-29 | 1985-07-31 | Vira Tek Inc | Procede de traitement medical de maladies virales utilisant le 1-beta-d-ribofurannosyl-1, 2,4-triazole-3-carboxamide. |
| NZ213370A (en) * | 1985-01-16 | 1989-03-29 | Vira Tek Inc | Method of treating viral infections of selected trees and field crops using ribavirin (1-b-d-ribofuranosyl-1,2,4-triazole-3-carboxamide) or the 2,3,5-triacetyl or 5'-butyryl derivative thereof |
| DE3606634A1 (de) * | 1986-02-28 | 1987-09-03 | Mack Chem Pharm | Isohexid-nucleoside, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| ATE135914T1 (de) * | 1986-03-27 | 1996-04-15 | Gensia Inc | Aica riboside zur prophylaktischen behandlung von krankheiten mit einer verminderten durchblutung. |
| US4925930A (en) * | 1988-11-02 | 1990-05-15 | Nucleic Acid Research Institute | Synthesis and anti-leukemic activity of alkyl-1-(β-D-ribofuranosyl)[1,2,4]triazole-3-carboximidates |
| US5438131A (en) * | 1992-09-16 | 1995-08-01 | Bergstrom; Donald E. | 3-nitropyrrole nucleoside |
| HK1049944A1 (zh) * | 1999-12-23 | 2003-06-06 | Icn Pharmaceuticals, Inc. | L-核苷、l-核苷酸及其类似物的组合物和治疗方法 |
| US6455508B1 (en) | 2000-02-15 | 2002-09-24 | Kanda S. Ramasamy | Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides |
| US6495677B1 (en) | 2000-02-15 | 2002-12-17 | Kanda S. Ramasamy | Nucleoside compounds |
| US7638496B2 (en) * | 2000-02-15 | 2009-12-29 | Valeant Pharmaceuticals North America | Nucleoside analogs with carboxamidine modified monocyclic base |
| PY0111577A (es) * | 2000-05-23 | 2017-01-02 | Idenix Cayman Ltd | Métodos y composiciones para el tratamiento del virus de la hepatitis c |
| AP2006003708A0 (en) | 2000-05-26 | 2006-08-31 | Idenix Cayman Ltd | Methods and compositions for treating flavivirusesand pestiviruses |
| US6815542B2 (en) * | 2000-06-16 | 2004-11-09 | Ribapharm, Inc. | Nucleoside compounds and uses thereof |
| JP2004518618A (ja) * | 2000-08-22 | 2004-06-24 | リバフアーム・インコーポレーテツド | 疾患の治療における改善特異性 |
| WO2002044717A1 (en) * | 2000-12-01 | 2002-06-06 | Cornell Research Foundation | Animal model for flaviviridae infection |
| US20040014696A1 (en) * | 2000-12-07 | 2004-01-22 | Johnson Lau | Specificity in treatment of diseases |
| US6720000B2 (en) * | 2001-03-19 | 2004-04-13 | Three Rivers Pharmaceutical, Llc | Process for producing wet ribavirin pellets |
| DE60101056T2 (de) * | 2001-07-30 | 2004-05-19 | Clariant Life Science Molecules (Italia) S.P.A., Origgio | Verfahren zur Herstellung von Ribavirin |
| AU2002330154A1 (en) * | 2001-09-28 | 2003-04-07 | Centre National De La Recherche Scientifique | Methods and compositions for treating hepatitis c virus using 4'-modified nucleosides |
| AU2002350082B9 (en) * | 2001-11-02 | 2006-08-31 | Sandoz Inc. | Process for preparing quick dissolving, high loading ribavirin compositions |
| KR100411398B1 (ko) | 2001-12-06 | 2003-12-18 | 주식회사유한양행 | 베타-디-리보푸라노즈 유도체의 제조방법 |
| CN1678326A (zh) * | 2002-06-28 | 2005-10-05 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2'－c－甲基－3'－o－l－缬氨酸酯核糖呋喃基胞苷 |
| CN101172993A (zh) * | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷 |
| PT1523489E (pt) | 2002-06-28 | 2014-06-24 | Centre Nat Rech Scient | Profármacos de nucleósido modificado em 2' e 3' para tratamento de infecções por flaviridae |
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-
1972
- 1972-03-31 US US00240252A patent/US3798209A/en not_active Expired - Lifetime
- 1972-04-25 DE DE19722220246 patent/DE2220246A1/de not_active Withdrawn
- 1972-05-11 IL IL39416A patent/IL39416A/xx unknown
- 1972-05-11 AU AU42157/72A patent/AU461900B2/en not_active Expired
- 1972-05-12 IE IE638/72A patent/IE36478B1/en unknown
- 1972-05-12 DK DK237072A patent/DK143069C/da not_active IP Right Cessation
- 1972-05-13 GB GB2241972A patent/GB1353565A/en not_active Expired
- 1972-05-13 JP JP4760172A patent/JPS5527076B1/ja active Pending
- 1972-05-15 IS IS2075A patent/IS913B6/is unknown
- 1972-05-20 EG EG203/72A patent/EG11406A/xx active
- 1972-05-24 ES ES403142A patent/ES403142A1/es not_active Expired
- 1972-05-25 CH CH776572A patent/CH614452A5/xx not_active IP Right Cessation
- 1972-05-26 NL NL7207156A patent/NL7207156A/xx not_active Application Discontinuation
- 1972-05-26 NO NO1858/72A patent/NO138805C/no unknown
- 1972-05-29 DD DD163262A patent/DD99791A5/xx unknown
- 1972-05-30 AR AR242262A patent/AR199463A1/es active
- 1972-05-31 SE SE7207131A patent/SE405604B/xx unknown
- 1972-05-31 BE BE784195A patent/BE784195A/xx unknown
- 1972-05-31 FR FR7219501A patent/FR2140126B1/fr not_active Expired
- 1972-05-31 BG BG020615A patent/BG22827A3/xx unknown
- 1972-05-31 MC MC995A patent/MC921A1/fr unknown
- 1972-05-31 CA CA143,816A patent/CA997756A/en not_active Expired
- 1972-05-31 HU HUIE507A patent/HU167614B/hu unknown
- 1972-06-01 RO RO7200071105A patent/RO62435A/ro unknown
- 1972-06-01 LU LU65446D patent/LU65446A1/xx unknown
-
1974
- 1974-05-09 IN IN1026/CAL/1974A patent/IN142290B/en unknown
-
1976
- 1976-04-22 HK HK238/76*UA patent/HK23876A/xx unknown
- 1976-11-12 DK DK509876A patent/DK509876A/da unknown
- 1976-12-30 MY MY203/76A patent/MY7600203A/xx unknown
-
1978
- 1978-01-13 JP JP326178A patent/JPS53108973A/ja active Pending
- 1978-01-13 JP JP326078A patent/JPS53124271A/ja active Pending
- 1978-01-13 JP JP325978A patent/JPS5387356A/ja active Granted
- 1978-01-13 JP JP325878A patent/JPS5395974A/ja active Granted
- 1978-02-20 SE SE7801925A patent/SE7801925L/xx unknown
- 1978-02-20 SE SE7801926A patent/SE7801926L/xx unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2511829A1 (de) * | 1974-03-18 | 1975-09-25 | Icn Pharmaceuticals | N-substituierte 1,2,4-triazole |
| DE2511828A1 (de) * | 1974-03-18 | 1975-10-02 | Icn Pharmaceuticals | 1-(beta-d-ribofuranosyl)-1,2,4-triazolsaeureester |
| DE2560551C2 (enExample) * | 1974-03-18 | 1989-02-23 | Viratek, Inc., Covina, Calif., Us | |
| US11110091B2 (en) | 2008-12-09 | 2021-09-07 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
| US11116774B2 (en) | 2014-07-11 | 2021-09-14 | Gilead Sciences, Inc. | Modulators of toll-like receptors for the treatment of HIV |
| US10508117B2 (en) | 2014-09-16 | 2019-12-17 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| US11072615B2 (en) | 2014-09-16 | 2021-07-27 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| US11773098B2 (en) | 2014-09-16 | 2023-10-03 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| US12486271B2 (en) | 2014-09-16 | 2025-12-02 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| US12611453B2 (en) | 2019-05-22 | 2026-04-28 | Gilead Sciences, Inc. | Method of inducing an HIV-1-specific immune response using a chimpanzee adenovirus vector encoding an hivacat t-cell immunogen and TLR7 agonist |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
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