AU2005254790B2 - Purine nucleotide derivatives - Google Patents
Purine nucleotide derivatives Download PDFInfo
- Publication number
- AU2005254790B2 AU2005254790B2 AU2005254790A AU2005254790A AU2005254790B2 AU 2005254790 B2 AU2005254790 B2 AU 2005254790B2 AU 2005254790 A AU2005254790 A AU 2005254790A AU 2005254790 A AU2005254790 A AU 2005254790A AU 2005254790 B2 AU2005254790 B2 AU 2005254790B2
- Authority
- AU
- Australia
- Prior art keywords
- camps
- mmol
- adenosine
- cyclic
- camp
- 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.)
- Ceased
Links
- 239000002213 purine nucleotide Substances 0.000 title description 6
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 64
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims description 101
- OIRDTQYFTABQOQ-KQYNXXCUSA-N Adenosine Natural products C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 63
- 239000005557 antagonist Substances 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000002904 solvent Substances 0.000 claims description 54
- 238000003556 assay Methods 0.000 claims description 52
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 46
- 229960005305 adenosine Drugs 0.000 claims description 46
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 41
- 230000000694 effects Effects 0.000 claims description 34
- 230000027455 binding Effects 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 24
- 239000000556 agonist Substances 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 5
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 5
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
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- FPHJJCBLRAPJQJ-CRKDRTNXSA-N (2s,3r,4s,5r)-2-amino-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical group C1=NC=2C(N)=NC=NC=2N1[C@]1(N)O[C@H](CO)[C@@H](O)[C@H]1O FPHJJCBLRAPJQJ-CRKDRTNXSA-N 0.000 claims 1
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- 102100030313 Signal peptidase complex subunit 1 Human genes 0.000 claims 1
- DVKQVRZMKBDMDH-UUOKFMHZSA-N 8-Br-cAMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1Br DVKQVRZMKBDMDH-UUOKFMHZSA-N 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 4
- SMPNJFHAPJOHPP-JOILOJCLSA-N Adenosine, cyclic 3',5'-[hydrogen [p(s)]-phosphorothioate] Chemical compound C([C@H]1O2)OP(O)(=S)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 SMPNJFHAPJOHPP-JOILOJCLSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 246
- 239000000243 solution Substances 0.000 description 132
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 114
- 238000005481 NMR spectroscopy Methods 0.000 description 112
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 90
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 79
- MHDLAWFYLQAULB-UHFFFAOYSA-N anilinophosphonic acid Chemical compound OP(O)(=O)NC1=CC=CC=C1 MHDLAWFYLQAULB-UHFFFAOYSA-N 0.000 description 67
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- 238000003818 flash chromatography Methods 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000741 silica gel Substances 0.000 description 59
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- -1 purine cyclic monophosphates Chemical class 0.000 description 58
- 230000002829 reductive effect Effects 0.000 description 53
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- 229910052786 argon Inorganic materials 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 44
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 39
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- RBORURQQJIQWBS-UHFFFAOYSA-N 6-(6-amino-8-bromopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol Chemical compound O1C2COP(O)(=S)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1Br RBORURQQJIQWBS-UHFFFAOYSA-N 0.000 description 23
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- CIQOJSYBTXSKSO-UHFFFAOYSA-N tributylazanium thiophosphate Chemical compound [O-]P([O-])([O-])=S.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC CIQOJSYBTXSKSO-UHFFFAOYSA-N 0.000 description 22
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- SMPNJFHAPJOHPP-PUHOFUEYSA-N (Rp)-cAMPS Chemical class C([C@H]1O2)O[P@](S)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 SMPNJFHAPJOHPP-PUHOFUEYSA-N 0.000 description 19
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 19
- 229910052698 phosphorus Inorganic materials 0.000 description 19
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
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- IVTHSFJXIARUFL-UHFFFAOYSA-N triazanium;thiophosphate Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=S IVTHSFJXIARUFL-UHFFFAOYSA-N 0.000 description 18
- ZJDYSLGODIRURM-UHFFFAOYSA-N (benzylamino)phosphonic acid Chemical compound OP(O)(=O)NCC1=CC=CC=C1 ZJDYSLGODIRURM-UHFFFAOYSA-N 0.000 description 17
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- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 15
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 14
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000005731 phosphitylation reaction Methods 0.000 description 1
- 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
- DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000009696 proliferative response Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002212 purine nucleoside Substances 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229940083045 riax Drugs 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- ILHHHOJPVCBSBI-GLVVJEGASA-M sodium;(4ar,6r,7r,7as)-6-(6-amino-8-piperidin-1-ylpurin-9-yl)-2-oxido-2-sulfanylidene-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol Chemical compound [Na+].N=1C=2C(N)=NC=NC=2N([C@H]2[C@@H]([C@@H]3OP([O-])(=S)OC[C@H]3O2)O)C=1N1CCCCC1 ILHHHOJPVCBSBI-GLVVJEGASA-M 0.000 description 1
- AWXMSJRRXLCVMW-JVSRKQJHSA-M sodium;(4ar,6r,7r,7as)-6-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-2-oxido-2-sulfanylidene-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol Chemical compound [Na+].N=1C=2C(N)=NC=NC=2N([C@H]2[C@@H]([C@@H]3OP([O-])(=S)OC[C@H]3O2)O)C=1SC1=CC=C(Cl)C=C1 AWXMSJRRXLCVMW-JVSRKQJHSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000006863 thiophosphorylation reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011277 treatment modality Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- WUOFQGMXQCSPPV-UHFFFAOYSA-N tributyl(1,3-thiazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CS1 WUOFQGMXQCSPPV-UHFFFAOYSA-N 0.000 description 1
- SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 1
- CFQJBWKKHCMCGJ-UHFFFAOYSA-N tributyl(pyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=C1 CFQJBWKKHCMCGJ-UHFFFAOYSA-N 0.000 description 1
- FLPKMHDTSOPPOJ-UHFFFAOYSA-N tributyl-(4-fluorophenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(F)C=C1 FLPKMHDTSOPPOJ-UHFFFAOYSA-N 0.000 description 1
- LIILCIIZVMZTSC-UHFFFAOYSA-N tributyl-(4-methoxyphenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OC)C=C1 LIILCIIZVMZTSC-UHFFFAOYSA-N 0.000 description 1
- MMGRHYVTTLMZJQ-UHFFFAOYSA-N tributyl-(5-methoxyfuran-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OC)O1 MMGRHYVTTLMZJQ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HPQUOZITTSKGPY-UHFFFAOYSA-M zinc;2h-thiophen-2-ide;chloride Chemical compound [Zn+]Cl.C=1C=[C-]SC=1 HPQUOZITTSKGPY-UHFFFAOYSA-M 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H19/213—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids containing cyclic phosphate
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0413726.1 | 2004-06-18 | ||
| GBGB0413726.1A GB0413726D0 (en) | 2004-06-18 | 2004-06-18 | Compounds |
| PCT/GB2005/002418 WO2005123755A2 (en) | 2004-06-18 | 2005-06-20 | Purine nucleotide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005254790A1 AU2005254790A1 (en) | 2005-12-29 |
| AU2005254790B2 true AU2005254790B2 (en) | 2012-02-23 |
Family
ID=32750205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005254790A Ceased AU2005254790B2 (en) | 2004-06-18 | 2005-06-20 | Purine nucleotide derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8153609B2 (enExample) |
| EP (1) | EP1765844B1 (enExample) |
| JP (1) | JP5044750B2 (enExample) |
| CN (1) | CN101001865A (enExample) |
| AU (1) | AU2005254790B2 (enExample) |
| CA (1) | CA2568907C (enExample) |
| DK (1) | DK1765844T3 (enExample) |
| ES (1) | ES2496946T3 (enExample) |
| GB (1) | GB0413726D0 (enExample) |
| WO (1) | WO2005123755A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007006544A2 (en) * | 2005-07-12 | 2007-01-18 | Vrije Universiteit Brussel | Cyclic adenosine monophosphate compounds for the treatment of immune-related disorders |
| GB0618235D0 (en) * | 2006-09-15 | 2006-10-25 | Lauras As | Process |
| WO2011001366A1 (en) * | 2009-06-29 | 2011-01-06 | Bioartic Neuroscience Ab | N-terminal truncated amyloid beta protofibrils/ oligomers for use in therapeutic and diagnostic methods for alzheimer's disease |
| WO2012040127A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US8772474B2 (en) | 2010-12-22 | 2014-07-08 | Alios Biopharma, Inc. | Cyclic nucleotide analogs |
| CA2860234A1 (en) | 2011-12-22 | 2013-06-27 | Alios Biopharma, Inc. | Substituted phosphorothioate nucleotide analogs |
| HUE041509T2 (hu) | 2011-12-22 | 2019-05-28 | Janssen Biopharma Inc | Szubsztituált nukleozidok, nukleotidok és ezek analógjai |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| HK1206362A1 (zh) | 2012-03-21 | 2016-01-08 | Alios Biopharma, Inc. | 硫代氨基磷酸酯核苷酸前藥的固體形式 |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| NZ630805A (en) | 2012-03-22 | 2016-01-29 | Alios Biopharma Inc | Pharmaceutical combinations comprising a thionucleotide analog |
| US20240182511A1 (en) * | 2021-04-09 | 2024-06-06 | Merck Sharp & Dohme Llc | Novel forms of cyclic dinucleotide compounds |
| EP4399215A1 (en) | 2021-09-06 | 2024-07-17 | Mireca Medicines GmbH | Improved methods for production of cyclic guanosine-monophosphate analogues |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003104250A1 (en) * | 2002-06-07 | 2003-12-18 | Kylix, B. V. | New compounds for modulating the activity of exchange proteins directly activated by camp (epacs) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968101A (en) * | 1974-12-20 | 1976-07-06 | Icn Pharmaceuticals, Inc. | 8-Substituted cyclic nucleotides by free radical alkylation and acylation |
| WO1989007108A1 (en) | 1988-02-01 | 1989-08-10 | Bernd Jastorff | Process for producing nucleoside-3',5'-cyclophosphates and nucleoside-3',5'-cyclothiophosphates |
| WO1993021929A1 (en) | 1992-05-01 | 1993-11-11 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Phosphorothioate derivatives of cyclic amp analogues |
| US5625056A (en) * | 1992-05-26 | 1997-04-29 | Biolog Life Science Institute | Derivatives of cyclic guanosine-3',5'-monophosphorothioate |
| NO971997D0 (no) | 1997-04-29 | 1997-04-29 | Kjetil Tasken | Bruk av immunmodulerende midler |
-
2004
- 2004-06-18 GB GBGB0413726.1A patent/GB0413726D0/en not_active Ceased
-
2005
- 2005-06-20 EP EP05755520.3A patent/EP1765844B1/en not_active Expired - Lifetime
- 2005-06-20 ES ES05755520.3T patent/ES2496946T3/es not_active Expired - Lifetime
- 2005-06-20 CN CNA2005800259528A patent/CN101001865A/zh active Pending
- 2005-06-20 JP JP2007516050A patent/JP5044750B2/ja not_active Expired - Fee Related
- 2005-06-20 DK DK05755520.3T patent/DK1765844T3/da active
- 2005-06-20 AU AU2005254790A patent/AU2005254790B2/en not_active Ceased
- 2005-06-20 CA CA2568907A patent/CA2568907C/en not_active Expired - Fee Related
- 2005-06-20 WO PCT/GB2005/002418 patent/WO2005123755A2/en not_active Ceased
- 2005-06-20 US US11/629,908 patent/US8153609B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003104250A1 (en) * | 2002-06-07 | 2003-12-18 | Kylix, B. V. | New compounds for modulating the activity of exchange proteins directly activated by camp (epacs) |
Non-Patent Citations (2)
| Title |
|---|
| Clayden, J. et al., "Organic Chemistry", Oxford University Press, Oxford, 2001, chapter 48, pages 1324-1332. * |
| X-B. Tian et al., Progress in Natural Science, 1994, 4 (6), 726-731. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1765844B1 (en) | 2014-07-30 |
| DK1765844T3 (da) | 2014-09-01 |
| CA2568907A1 (en) | 2005-12-29 |
| WO2005123755A2 (en) | 2005-12-29 |
| EP1765844A2 (en) | 2007-03-28 |
| US20080293665A1 (en) | 2008-11-27 |
| US8153609B2 (en) | 2012-04-10 |
| CN101001865A (zh) | 2007-07-18 |
| CA2568907C (en) | 2015-06-09 |
| AU2005254790A1 (en) | 2005-12-29 |
| JP5044750B2 (ja) | 2012-10-10 |
| GB0413726D0 (en) | 2004-07-21 |
| WO2005123755A3 (en) | 2006-04-06 |
| ES2496946T3 (es) | 2014-09-22 |
| JP2008502673A (ja) | 2008-01-31 |
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