JP2008502673A5 - - Google Patents
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- Publication number
- JP2008502673A5 JP2008502673A5 JP2007516050A JP2007516050A JP2008502673A5 JP 2008502673 A5 JP2008502673 A5 JP 2008502673A5 JP 2007516050 A JP2007516050 A JP 2007516050A JP 2007516050 A JP2007516050 A JP 2007516050A JP 2008502673 A5 JP2008502673 A5 JP 2008502673A5
- Authority
- JP
- Japan
- Prior art keywords
- carbyl
- cyclic
- camps
- group
- substituted
- 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.)
- Granted
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- 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 18
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 13
- 229960005305 adenosine Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- -1 amino, carboxy Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 3
- 150000003536 tetrazoles Chemical class 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- 150000003852 triazoles Chemical class 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 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
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- SUEGWIXYCHISPX-UHFFFAOYSA-N sulfane trihydroxy(sulfanylidene)-lambda5-phosphane Chemical compound OP(O)(O)=S.S SUEGWIXYCHISPX-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- FPUGCISOLXNPPC-IOSLPCCCSA-N cordysinin B Chemical compound CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 FPUGCISOLXNPPC-IOSLPCCCSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- SMPNJFHAPJOHPP-PUHOFUEYSA-N (Rp)-cAMPS Chemical compound 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 1
- FPUGCISOLXNPPC-UHFFFAOYSA-N 2'-O-Methyladenosine Natural products COC1C(O)C(CO)OC1N1C2=NC=NC(N)=C2N=C1 FPUGCISOLXNPPC-UHFFFAOYSA-N 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- 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 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JVRGLGIDPIOAFN-UHFFFAOYSA-N methoxyphosphane Chemical compound COP JVRGLGIDPIOAFN-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000002743 phosphorus functional group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0413726.1A GB0413726D0 (en) | 2004-06-18 | 2004-06-18 | Compounds |
| GB0413726.1 | 2004-06-18 | ||
| PCT/GB2005/002418 WO2005123755A2 (en) | 2004-06-18 | 2005-06-20 | Purine nucleotide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008502673A JP2008502673A (ja) | 2008-01-31 |
| JP2008502673A5 true JP2008502673A5 (https=) | 2012-02-02 |
| JP5044750B2 JP5044750B2 (ja) | 2012-10-10 |
Family
ID=32750205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007516050A Expired - Fee Related JP5044750B2 (ja) | 2004-06-18 | 2005-06-20 | プリンヌクレオチド誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8153609B2 (https=) |
| EP (1) | EP1765844B1 (https=) |
| JP (1) | JP5044750B2 (https=) |
| CN (1) | CN101001865A (https=) |
| AU (1) | AU2005254790B2 (https=) |
| CA (1) | CA2568907C (https=) |
| DK (1) | DK1765844T3 (https=) |
| ES (1) | ES2496946T3 (https=) |
| GB (1) | GB0413726D0 (https=) |
| WO (1) | WO2005123755A2 (https=) |
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 |
| LT2448968T (lt) * | 2009-06-29 | 2021-05-10 | Bioarctic Ab | Antikūnai, atpažįstantys n gale sutrumpintas amiloido protofibriles/oligomerus |
| NZ607996A (en) | 2010-09-22 | 2014-07-25 | Alios Biopharma Inc | Substituted nucleotide analogs |
| CA2819041A1 (en) * | 2010-12-22 | 2012-06-28 | Alios Biopharma, Inc. | Cyclic nucleotide analogs |
| CA2860234A1 (en) | 2011-12-22 | 2013-06-27 | Alios Biopharma, Inc. | Substituted phosphorothioate nucleotide analogs |
| SG10201913554YA (en) | 2011-12-22 | 2020-03-30 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| 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 |
| WO2013142157A1 (en) | 2012-03-22 | 2013-09-26 | 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 |
| CN117999269A (zh) | 2021-09-06 | 2024-05-07 | 米雷卡医药有限公司 | 用于生产环状鸟苷-单磷酸酯类似物的改进方法 |
Family Cites Families (6)
| 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 |
| JP4902958B2 (ja) * | 2002-06-07 | 2012-03-21 | ユニバーシテール・メディッシュ・セントラム・ユトレヒト | ｃＡＭＰによって直接活性化される交換タンパク質（Ｅｐａｃ）の活性をモジュレートするための新規な化合物 |
-
2004
- 2004-06-18 GB GBGB0413726.1A patent/GB0413726D0/en not_active Ceased
-
2005
- 2005-06-20 CA CA2568907A patent/CA2568907C/en not_active Expired - Fee Related
- 2005-06-20 DK DK05755520.3T patent/DK1765844T3/da active
- 2005-06-20 ES ES05755520.3T patent/ES2496946T3/es not_active Expired - Lifetime
- 2005-06-20 US US11/629,908 patent/US8153609B2/en not_active Expired - Fee Related
- 2005-06-20 AU AU2005254790A patent/AU2005254790B2/en not_active Ceased
- 2005-06-20 WO PCT/GB2005/002418 patent/WO2005123755A2/en not_active Ceased
- 2005-06-20 JP JP2007516050A patent/JP5044750B2/ja not_active Expired - Fee Related
- 2005-06-20 CN CNA2005800259528A patent/CN101001865A/zh active Pending
- 2005-06-20 EP EP05755520.3A patent/EP1765844B1/en not_active Expired - Lifetime
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