JP2019529523A5 - - Google Patents
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- JP2019529523A5 JP2019529523A5 JP2019523168A JP2019523168A JP2019529523A5 JP 2019529523 A5 JP2019529523 A5 JP 2019529523A5 JP 2019523168 A JP2019523168 A JP 2019523168A JP 2019523168 A JP2019523168 A JP 2019523168A JP 2019529523 A5 JP2019529523 A5 JP 2019529523A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- thio
- aryl
- aralkyl
- cyclic monophosphorothioate
- 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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- -1 1-(o-nitrophenyl)-ethylidene, 4,5-dimethoxy-2-nitro-benzyl Chemical group 0.000 claims description 148
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000002202 Polyethylene glycol Substances 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 23
- 239000000975 dye Substances 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical class 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 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 description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 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 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000012099 Alexa Fluor family Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 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 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 235000020958 biotin Nutrition 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000021615 conjugation Effects 0.000 claims description 2
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims description 2
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 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 description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 102000034287 fluorescent proteins Human genes 0.000 claims description 2
- 108091006047 fluorescent proteins Proteins 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-O octylazanium Chemical compound CCCCCCCC[NH3+] IOQPZZOEVPZRBK-UHFFFAOYSA-O 0.000 claims description 2
- 230000006320 pegylation Effects 0.000 claims description 2
- WWBGWPHHLRSTFI-UHFFFAOYSA-N phenalen-1-one Chemical compound C1=CC(C(=O)C=C2)=C3C2=CC=CC3=C1 WWBGWPHHLRSTFI-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000002096 quantum dot Substances 0.000 claims description 2
- 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 description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 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 description 2
- 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 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- KBIVNMNCTHXFAZ-PHDIDXHHSA-N 2-amino-9-[(2r,5r)-5-(dihydroxyphosphinothioyloxymethyl)-4-hydroxy-2,5-dihydrofuran-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=S)C(O)=C1 KBIVNMNCTHXFAZ-PHDIDXHHSA-N 0.000 claims 35
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 19
- 229910004013 NO 2 Inorganic materials 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 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 9
- 239000000178 monomer Substances 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 208000017442 Retinal disease Diseases 0.000 claims 5
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 239000002243 precursor Substances 0.000 claims 4
- 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 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 3
- OGPGXHCVHUKIGS-ZMOGYAJESA-N fluoresceinylthioureido Chemical group OC(=O)C1=CC(=N/C=[S]/NCC)/C=CC1=C1C2=CC=C(O)C=C2OC2=CC(O)=CC=C21 OGPGXHCVHUKIGS-ZMOGYAJESA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 150000002430 hydrocarbons Chemical group 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 2
- 238000010276 construction Methods 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ASUCSHXLTWZYBA-UMMCILCDSA-N 8-Bromoguanosine Chemical compound C1=2NC(N)=NC(=O)C=2N=C(Br)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ASUCSHXLTWZYBA-UMMCILCDSA-N 0.000 claims 1
- 208000000230 African Trypanosomiasis Diseases 0.000 claims 1
- 206010001935 American trypanosomiasis Diseases 0.000 claims 1
- 206010002653 Anosmia Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000024699 Chagas disease Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy 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
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Natural products COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 241000243985 Onchocerca volvulus Species 0.000 claims 1
- 208000030852 Parasitic disease Diseases 0.000 claims 1
- 208000002367 Retinal Perforations Diseases 0.000 claims 1
- 206010038848 Retinal detachment Diseases 0.000 claims 1
- 201000000582 Retinoblastoma Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 241000223105 Trypanosoma brucei Species 0.000 claims 1
- 241000223109 Trypanosoma cruzi Species 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 235000019558 anosmia Nutrition 0.000 claims 1
- 230000003376 axonal effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 208000024519 eye neoplasm Diseases 0.000 claims 1
- 208000029080 human African trypanosomiasis Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 208000029233 macular holes Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 229940102398 methyl anthranilate Drugs 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 208000003177 ocular onchocerciasis Diseases 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 210000001525 retina Anatomy 0.000 claims 1
- 230000004264 retinal detachment Effects 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 201000002612 sleeping sickness Diseases 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 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 claims 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022107321A JP7672368B2 (ja) | 2016-07-11 | 2022-07-01 | ３’，５’－環状グアノシン一リン酸の新規エクアトリアル修飾ポリマー連結マルチマー |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16178924 | 2016-07-11 | ||
| EP16178924.3 | 2016-07-11 | ||
| PCT/EP2017/066113 WO2018010965A1 (en) | 2016-07-11 | 2017-06-29 | New equatorially modified polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022107321A Division JP7672368B2 (ja) | 2016-07-11 | 2022-07-01 | ３’，５’－環状グアノシン一リン酸の新規エクアトリアル修飾ポリマー連結マルチマー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019529523A JP2019529523A (ja) | 2019-10-17 |
| JP2019529523A5 true JP2019529523A5 (enExample) | 2020-08-06 |
| JP7113409B2 JP7113409B2 (ja) | 2022-08-05 |
Family
ID=56411445
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019523168A Active JP7113409B2 (ja) | 2016-07-11 | 2017-06-29 | ３’，５’－環状グアノシン一リン酸の新規エクアトリアル修飾ポリマー連結マルチマー |
| JP2022107321A Active JP7672368B2 (ja) | 2016-07-11 | 2022-07-01 | ３’，５’－環状グアノシン一リン酸の新規エクアトリアル修飾ポリマー連結マルチマー |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022107321A Active JP7672368B2 (ja) | 2016-07-11 | 2022-07-01 | ３’，５’－環状グアノシン一リン酸の新規エクアトリアル修飾ポリマー連結マルチマー |
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| CA3069586A1 (en) | 2016-07-11 | 2018-01-18 | Mireca Medicines Gmbh | New equatorially modified polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
| WO2018041942A1 (en) * | 2016-08-31 | 2018-03-08 | Biolog Life Science Institute Forschungslabor Und Biochemica-Vertrieb Gmbh | New polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
| JP7161760B2 (ja) * | 2017-02-03 | 2022-10-27 | 国立大学法人東北大学 | 複素環化合物 |
| EP3679935A4 (en) * | 2017-07-10 | 2021-04-21 | Tohoku University | REMOVAL AGENT WITH AUTOPHAGIC MECHANISM OF DAMAGED MITOCHONDRIA |
| 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 |
| CA3267932A1 (en) | 2022-10-05 | 2024-04-11 | Mireca Medicines Gmbh | MICROPARCEL AND IMPLANT FORMULATIONS FOR ANALOGUE CGMP THERAPY |
| EP4598580A1 (en) | 2022-10-06 | 2025-08-13 | Mireca Medicines GmbH | Conjugates for neuroretinal drug delivery |
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| WO1989007108A1 (en) | 1988-02-01 | 1989-08-10 | Bernd Jastorff | Process for producing nucleoside-3',5'-cyclophosphates and nucleoside-3',5'-cyclothiophosphates |
| 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 |
| MX2008006550A (es) | 2005-11-23 | 2008-09-23 | Ironwood Pharmaceuticals Inc | Metodos y composiciones para el tratamiento de trastornos gastrointestinales. |
| EP2125027A2 (en) | 2007-03-12 | 2009-12-02 | Nektar Therapeutics | De novo synthesis of conjugates |
| WO2009026697A1 (en) | 2007-08-28 | 2009-03-05 | University Of Manitoba | A method of reducing a vasodilatory response using a guanylate cyclase pathway inhibitor or an h2o2 reducing agent |
| TR201908314T4 (tr) | 2009-02-20 | 2019-06-21 | 2 Bbb Medicines B V | Glutatyon bazlı ilaç dağıtım sistemi. |
| WO2012130829A1 (en) | 2011-03-29 | 2012-10-04 | Biolog Life Science Institute Forschungslabor Und Biochemica-Vertrieb Gmbh | New boranophosphate analogues of cyclic nucleotides |
| SG11201705913UA (en) | 2015-01-23 | 2017-08-30 | Dynavax Tech Corp | Branched and linear chimeric compounds, polynucleotides, uses and methods for preparation thereof |
| US10322087B2 (en) | 2015-03-16 | 2019-06-18 | Mireca Medicines Gmbh | Targeted liposomal delivery of cGMP analogues |
| WO2018009587A1 (en) | 2016-07-05 | 2018-01-11 | Orbis Wheels, Inc. | Multi-wheel transmission |
| CA3069586A1 (en) | 2016-07-11 | 2018-01-18 | Mireca Medicines Gmbh | New equatorially modified polymer linked multimers of guanosine-3', 5'-cyclic monophosphates |
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2017
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- 2017-06-29 WO PCT/EP2017/066113 patent/WO2018010965A1/en not_active Ceased
- 2017-06-29 JP JP2019523168A patent/JP7113409B2/ja active Active
- 2017-06-29 EP EP17736619.2A patent/EP3481842A1/en active Pending
- 2017-06-29 US US16/316,934 patent/US11407781B2/en active Active
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2022
- 2022-07-01 JP JP2022107321A patent/JP7672368B2/ja active Active
- 2022-08-08 US US17/883,398 patent/US12583882B2/en active Active
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