MX2011008409A - Análogos de carba-nucléosido para tratamiento antiviral. - Google Patents
Análogos de carba-nucléosido para tratamiento antiviral.Info
- Publication number
- MX2011008409A MX2011008409A MX2011008409A MX2011008409A MX2011008409A MX 2011008409 A MX2011008409 A MX 2011008409A MX 2011008409 A MX2011008409 A MX 2011008409A MX 2011008409 A MX2011008409 A MX 2011008409A MX 2011008409 A MX2011008409 A MX 2011008409A
- Authority
- MX
- Mexico
- Prior art keywords
- substituted
- alkyl
- compound
- independently
- formula
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 26
- 239000002777 nucleoside Substances 0.000 title claims description 32
- 230000000840 anti-viral effect Effects 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 322
- -1 furo[3,4-d]pyrimidin-7-yl ribosides Chemical class 0.000 claims abstract description 177
- 239000000203 mixture Substances 0.000 claims abstract description 175
- 238000000034 method Methods 0.000 claims abstract description 124
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- 125000000217 alkyl group Chemical group 0.000 claims description 269
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 89
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- 150000002367 halogens Chemical class 0.000 claims description 55
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 150000001721 carbon Chemical group 0.000 claims description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
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- 150000002148 esters Chemical class 0.000 claims description 38
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 37
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- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 32
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- 229940124597 therapeutic agent Drugs 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
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- 125000003545 alkoxy group Chemical group 0.000 claims description 25
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 24
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- 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 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
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- 229910052731 fluorine Inorganic materials 0.000 claims description 18
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- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 15
- 241000700605 Viruses Species 0.000 claims description 15
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- 229940047124 interferons Drugs 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 229960000329 ribavirin Drugs 0.000 claims description 9
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 9
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- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 7
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 claims description 4
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 4
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 4
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- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 241000710771 Tick-borne encephalitis virus Species 0.000 claims description 3
- 241000907316 Zika virus Species 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 241000725619 Dengue virus Species 0.000 claims description 2
- 241000710908 Murray Valley encephalitis virus Species 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229940051021 yellow-fever virus Drugs 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 241000710912 Kunjin virus Species 0.000 claims 1
- 208000011448 Omsk hemorrhagic fever Diseases 0.000 claims 1
- 241000710888 St. Louis encephalitis virus Species 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 abstract description 32
- 239000000651 prodrug Substances 0.000 abstract description 32
- 238000002360 preparation method Methods 0.000 abstract description 14
- 239000000543 intermediate Substances 0.000 abstract description 11
- 229910019142 PO4 Inorganic materials 0.000 abstract description 4
- 235000021317 phosphate Nutrition 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 229
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- 238000006243 chemical reaction Methods 0.000 description 94
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 79
- 239000000243 solution Substances 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
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- 125000001424 substituent group Chemical group 0.000 description 60
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- 235000019439 ethyl acetate Nutrition 0.000 description 41
- 239000002253 acid Substances 0.000 description 40
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- 238000009472 formulation Methods 0.000 description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 150000002900 organolithium compounds Chemical class 0.000 description 35
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 22
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
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- 239000002585 base Substances 0.000 description 18
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- 229940125904 compound 1 Drugs 0.000 description 17
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- 239000012453 solvate Substances 0.000 description 16
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 238000007792 addition Methods 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
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- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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
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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
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- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
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- A61P31/14—Antivirals for RNA viruses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
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- 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
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- 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
- C07H19/048—Pyridine radicals
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- 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
- C07H19/06—Pyrimidine radicals
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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