JP2019526576A5 - - Google Patents
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- Publication number
- JP2019526576A5 JP2019526576A5 JP2019511909A JP2019511909A JP2019526576A5 JP 2019526576 A5 JP2019526576 A5 JP 2019526576A5 JP 2019511909 A JP2019511909 A JP 2019511909A JP 2019511909 A JP2019511909 A JP 2019511909A JP 2019526576 A5 JP2019526576 A5 JP 2019526576A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclic monophosphate
- guanosine
- formula
- phenyl
- thio
- 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
Links
- -1 o-nitro-benzyl Chemical group 0.000 claims 161
- 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 claims 90
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 16
- 229910052794 bromium Inorganic materials 0.000 claims 15
- 229910052801 chlorine Inorganic materials 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 15
- 229910004013 NO 2 Inorganic materials 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 239000000178 monomer Substances 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 229920001223 polyethylene glycol Polymers 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 239000002202 Polyethylene glycol Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229910052740 iodine Inorganic materials 0.000 claims 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 239000000975 dye Substances 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 230000008878 coupling Effects 0.000 claims 8
- 238000010168 coupling process Methods 0.000 claims 8
- 238000005859 coupling reaction Methods 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000000524 functional group Chemical group 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000005647 linker group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 239000002243 precursor Substances 0.000 claims 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 5
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims 5
- 150000001721 carbon Chemical class 0.000 claims 5
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000004712 monophosphates Chemical class 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 2
- 208000016604 Lyme disease Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- VRDSRXVCRBMZOD-UHFFFAOYSA-N 1-benzyltriazole Chemical compound C1=CN=NN1CC1=CC=CC=C1 VRDSRXVCRBMZOD-UHFFFAOYSA-N 0.000 claims 1
- AYKMXKNVEUMLFQ-UHFFFAOYSA-N 2-(1,8-naphthyridin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=CC=N2)C2=N1 AYKMXKNVEUMLFQ-UHFFFAOYSA-N 0.000 claims 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- YUFCOOWNNHGGOD-UMMCILCDSA-N 8-bromo-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=C1Br YUFCOOWNNHGGOD-UMMCILCDSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000000230 African Trypanosomiasis Diseases 0.000 claims 1
- 239000012099 Alexa Fluor family Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 241000589968 Borrelia Species 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 208000001204 Hashimoto Disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 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 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000026072 Motor neurone disease Diseases 0.000 claims 1
- 208000009525 Myocarditis Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000030852 Parasitic disease Diseases 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 208000000474 Poliomyelitis Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 208000032319 Primary lateral sclerosis Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- 241000223104 Trypanosoma Species 0.000 claims 1
- 206010046298 Upper motor neurone lesion Diseases 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229960002685 biotin Drugs 0.000 claims 1
- 235000020958 biotin Nutrition 0.000 claims 1
- 239000011616 biotin Substances 0.000 claims 1
- 229940006460 bromide ion Drugs 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 125000005131 dialkylammonium group Chemical group 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 239000007850 fluorescent dye Substances 0.000 claims 1
- 102000034287 fluorescent proteins Human genes 0.000 claims 1
- 108091006047 fluorescent proteins Proteins 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 208000029080 human African trypanosomiasis Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- 229940006461 iodide ion Drugs 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000000715 neuromuscular junction Anatomy 0.000 claims 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-O octylazanium Chemical compound CCCCCCCC[NH3+] IOQPZZOEVPZRBK-UHFFFAOYSA-O 0.000 claims 1
- 230000001769 paralizing effect Effects 0.000 claims 1
- 230000006320 pegylation Effects 0.000 claims 1
- WWBGWPHHLRSTFI-UHFFFAOYSA-N phenalen-1-one Chemical compound C1=CC(C(=O)C=C2)=C3C2=CC=CC3=C1 WWBGWPHHLRSTFI-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229940085991 phosphate ion Drugs 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 239000002096 quantum dot Substances 0.000 claims 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 201000002612 sleeping sickness Diseases 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 125000006850 spacer group Chemical group 0.000 claims 1
- 230000003977 synaptic function Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023010090A JP2023102288A (ja) | 2016-08-31 | 2023-01-26 | グアノシン－３’，５’－環状一リン酸の新たなポリマー結合マルチマー |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16186700.7 | 2016-08-31 | ||
| EP16186700 | 2016-08-31 | ||
| PCT/EP2017/071859 WO2018041942A1 (en) | 2016-08-31 | 2017-08-31 | New polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023010090A Division JP2023102288A (ja) | 2016-08-31 | 2023-01-26 | グアノシン－３’，５’－環状一リン酸の新たなポリマー結合マルチマー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019526576A JP2019526576A (ja) | 2019-09-19 |
| JP2019526576A5 true JP2019526576A5 (enExample) | 2020-10-08 |
| JP7298048B2 JP7298048B2 (ja) | 2023-06-27 |
Family
ID=56990226
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019511909A Active JP7298048B2 (ja) | 2016-08-31 | 2017-08-31 | グアノシン－３’，５’－環状一リン酸の新たなポリマー結合マルチマー |
| JP2023010090A Pending JP2023102288A (ja) | 2016-08-31 | 2023-01-26 | グアノシン－３’，５’－環状一リン酸の新たなポリマー結合マルチマー |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023010090A Pending JP2023102288A (ja) | 2016-08-31 | 2023-01-26 | グアノシン－３’，５’－環状一リン酸の新たなポリマー結合マルチマー |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US20210317156A1 (enExample) |
| EP (1) | EP3507295A1 (enExample) |
| JP (2) | JP7298048B2 (enExample) |
| WO (1) | WO2018041942A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7161760B2 (ja) * | 2017-02-03 | 2022-10-27 | 国立大学法人東北大学 | 複素環化合物 |
| CA3267932A1 (en) | 2022-10-05 | 2024-04-11 | Mireca Medicines Gmbh | MICROPARCEL AND IMPLANT FORMULATIONS FOR ANALOGUE CGMP THERAPY |
| CN117946407B (zh) * | 2023-12-18 | 2025-11-18 | 浙江大学 | 基于Zn-MOFs构建的双模式光学探针及制备与对HOCl和H2O2的检测方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5625056A (en) | 1992-05-26 | 1997-04-29 | Biolog Life Science Institute | Derivatives of cyclic guanosine-3',5'-monophosphorothioate |
| WO1999025384A2 (en) | 1997-11-17 | 1999-05-27 | University Of Miami | Multimeric tethered ligands and their use in receptor-ligand interactions |
| EP2125027A2 (en) | 2007-03-12 | 2009-12-02 | Nektar Therapeutics | De novo synthesis of conjugates |
| WO2012130829A1 (en) | 2011-03-29 | 2012-10-04 | Biolog Life Science Institute Forschungslabor Und Biochemica-Vertrieb Gmbh | New boranophosphate analogues of cyclic nucleotides |
| MX379365B (es) | 2014-06-30 | 2025-03-11 | Tarveda Therapeutics Inc | Conjugados y partículas direccionados y formulaciones de estos. |
| SG11201705913UA (en) | 2015-01-23 | 2017-08-30 | Dynavax Tech Corp | Branched and linear chimeric compounds, polynucleotides, uses and methods for preparation thereof |
| CA3069586A1 (en) * | 2016-07-11 | 2018-01-18 | Mireca Medicines Gmbh | New equatorially modified polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
-
2017
- 2017-08-31 WO PCT/EP2017/071859 patent/WO2018041942A1/en not_active Ceased
- 2017-08-31 US US16/329,031 patent/US20210317156A1/en not_active Abandoned
- 2017-08-31 JP JP2019511909A patent/JP7298048B2/ja active Active
- 2017-08-31 EP EP17758198.0A patent/EP3507295A1/en active Pending
-
2022
- 2022-09-01 US US17/901,771 patent/US12384813B2/en active Active
-
2023
- 2023-01-26 JP JP2023010090A patent/JP2023102288A/ja active Pending
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