JP6892916B2 - Saicarの蓄積を減少させる化合物及び使用 - Google Patents
Saicarの蓄積を減少させる化合物及び使用 Download PDFInfo
- Publication number
- JP6892916B2 JP6892916B2 JP2019516529A JP2019516529A JP6892916B2 JP 6892916 B2 JP6892916 B2 JP 6892916B2 JP 2019516529 A JP2019516529 A JP 2019516529A JP 2019516529 A JP2019516529 A JP 2019516529A JP 6892916 B2 JP6892916 B2 JP 6892916B2
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- Japan
- Prior art keywords
- acid
- amino
- methyl
- sulfonate
- hydroxy
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims description 33
- NAQGHJTUZRHGAC-ZZZDFHIKSA-N SAICAR Chemical compound NC1=C(C(=O)N[C@@H](CC(O)=O)C(O)=O)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 NAQGHJTUZRHGAC-ZZZDFHIKSA-N 0.000 title claims description 23
- 238000009825 accumulation Methods 0.000 title description 6
- -1 (+)-L-lactates Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 23
- 108700037034 Adenylosuccinate lyase deficiency Proteins 0.000 claims description 19
- 230000007812 deficiency Effects 0.000 claims description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 14
- 102100027330 Phosphoribosylaminoimidazole carboxylase Human genes 0.000 claims description 13
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims description 13
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- SKGAVCHIFDRDTK-UHFFFAOYSA-N 1-guanidinium-7-aminoheptane Chemical compound NCCCCCCCNC(N)N SKGAVCHIFDRDTK-UHFFFAOYSA-N 0.000 claims description 7
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 7
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 claims description 5
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 5
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 5
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
- OFBHPPMPBOJXRT-VWJPMABRSA-N adenylosuccinic acid Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C2=NC=NC(N[C@@H](CC(O)=O)C(O)=O)=C2N=C1 OFBHPPMPBOJXRT-VWJPMABRSA-N 0.000 claims description 5
- 235000010443 alginic acid Nutrition 0.000 claims description 5
- 229920000615 alginic acid Polymers 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 235000010323 ascorbic acid Nutrition 0.000 claims description 5
- 239000011668 ascorbic acid Substances 0.000 claims description 5
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 5
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 5
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 5
- 235000001968 nicotinic acid Nutrition 0.000 claims description 5
- 239000011664 nicotinic acid Substances 0.000 claims description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- 108010035774 phosphoribosylaminoimidazole carboxylase Proteins 0.000 claims description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 4
- 229940043264 dodecyl sulfate Drugs 0.000 claims description 4
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 230000002452 interceptive effect Effects 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- 229960004274 stearic acid Drugs 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- QGWRMTHFAZVWAM-WDSKDSINSA-N (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfopropan-2-yl]amino]-5-oxopentanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS(O)(=O)=O)C(=O)NCC(O)=O QGWRMTHFAZVWAM-WDSKDSINSA-N 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- ZDGJAHTZVHVLOT-YUMQZZPRSA-N L-saccharopine Chemical compound OC(=O)[C@@H](N)CCCCN[C@H](C(O)=O)CCC(O)=O ZDGJAHTZVHVLOT-YUMQZZPRSA-N 0.000 claims description 3
- PIUSLWSYOYFRFR-BQBZGAKWSA-N S-(hydroxymethyl)glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O PIUSLWSYOYFRFR-BQBZGAKWSA-N 0.000 claims description 3
- QTQDDTSVRVWHMO-BQBZGAKWSA-N S-methylglutathione Chemical compound OC(=O)CNC(=O)[C@H](CSC)NC(=O)CC[C@H](N)C(O)=O QTQDDTSVRVWHMO-BQBZGAKWSA-N 0.000 claims description 3
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical class OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 3
- FCIHAQFHXJOLIF-YFKPBYRVSA-N n-(phosphonoacetyl)-l-ornithine Chemical compound OC(=O)[C@@H](N)CCCNC(=O)CP(O)(O)=O FCIHAQFHXJOLIF-YFKPBYRVSA-N 0.000 claims description 3
- SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N SYJXFKPQNSDJLI-HKEUSBCWSA-N 0.000 claims description 3
- XINFXVVRMYBFMI-YFKPBYRVSA-N nz-(dicarboxymethyl)lysine Chemical compound OC(=O)[C@@H](N)CCCCNC(C(O)=O)C(O)=O XINFXVVRMYBFMI-YFKPBYRVSA-N 0.000 claims description 3
- 108090000434 Phosphoribosylaminoimidazolesuccinocarboxamide synthases Proteins 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- DMAPAHUEYHXRFI-WDSKDSINSA-N glutathione sulfinate Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](C[S@](O)=O)C(=O)NCC(O)=O DMAPAHUEYHXRFI-WDSKDSINSA-N 0.000 claims description 2
- ZFYULDAPZWEGGQ-UHFFFAOYSA-N n-ethyl-n'-[3-(propylamino)propyl]propane-1,3-diamine Chemical compound CCCNCCCNCCCNCC ZFYULDAPZWEGGQ-UHFFFAOYSA-N 0.000 claims description 2
- BFPIKGKMRKBBBF-GRIPGOBMSA-N puromycin aminonucleoside-5'-monophosphate Chemical compound C1=NC=2C(N(C)C)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](N)[C@H]1O BFPIKGKMRKBBBF-GRIPGOBMSA-N 0.000 claims description 2
- MVFPGTZTOAHVBP-HXYLPHSESA-N tetrahedral intermediate of blasticidin s Chemical compound O1[C@H](C(O)=O)[C@@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@@H]1N1C(=O)N[C@](N)(O)C=C1 MVFPGTZTOAHVBP-HXYLPHSESA-N 0.000 claims description 2
- 229940063673 spermidine Drugs 0.000 claims 6
- 229910019142 PO4 Inorganic materials 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 3
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 108090000856 Lyases Proteins 0.000 claims 3
- 102000004317 Lyases Human genes 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
- 229920002253 Tannate Polymers 0.000 claims 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 3
- 229940072056 alginate Drugs 0.000 claims 3
- 229940072107 ascorbate Drugs 0.000 claims 3
- 229940077388 benzenesulfonate Drugs 0.000 claims 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 3
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-M dichloroacetate Chemical compound [O-]C(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-M 0.000 claims 3
- 125000005612 glucoheptonate group Chemical group 0.000 claims 3
- 150000002306 glutamic acid derivatives Chemical class 0.000 claims 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 3
- 229940049920 malate Drugs 0.000 claims 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 3
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 claims 3
- 229940049964 oleate Drugs 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 3
- 229960001860 salicylate Drugs 0.000 claims 3
- 229940116351 sebacate Drugs 0.000 claims 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 3
- 150000007971 urates Chemical class 0.000 claims 3
- LMXOHSDXUQEUSF-UHFFFAOYSA-N 2,5-diamino-6-[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid Chemical compound OC1C(O)C(CC(CCC(N)C(O)=O)N)OC1N1C2=NC=NC(N)=C2N=C1 LMXOHSDXUQEUSF-UHFFFAOYSA-N 0.000 claims 2
- FFRUQSUMDFNBLG-UHFFFAOYSA-N 2-(2,4,5-trichlorophenoxy)ethyl 2,2,2-trichloroacetate Chemical compound ClC1=CC(Cl)=C(OCCOC(=O)C(Cl)(Cl)Cl)C=C1Cl FFRUQSUMDFNBLG-UHFFFAOYSA-N 0.000 claims 2
- IVHKZCSZELZKSJ-UHFFFAOYSA-N 2-hydroxyethyl sulfonate Chemical compound OCCOS(=O)=O IVHKZCSZELZKSJ-UHFFFAOYSA-N 0.000 claims 2
- AZUQIXJQZOMXAS-IUCAKERBSA-N 2-oxy-4-hydroxy-5-(2-hydrazinopyridine)phenylalanine Chemical compound OC1=CC(=O)[C@@H](C[C@H](N)C(O)=O)C=C1NNC1=CC=CC=N1 AZUQIXJQZOMXAS-IUCAKERBSA-N 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- VWXQFHJBQHTHMK-LURJTMIESA-M N(2)-succinyl-L-ornithinate(1-) Chemical compound [NH3+]CCC[C@@H](C([O-])=O)NC(=O)CCC([O-])=O VWXQFHJBQHTHMK-LURJTMIESA-M 0.000 claims 2
- JMRKOGDJNHPMHS-SNVBAGLBSA-N N-Pyridoxyl-D-glutamic acid-5'-monophosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(CN[C@H](CCC(O)=O)C(O)=O)=C1O JMRKOGDJNHPMHS-SNVBAGLBSA-N 0.000 claims 2
- QTQDDTSVRVWHMO-UHFFFAOYSA-N S-Methylglutathione Natural products OC(=O)CNC(=O)C(CSC)NC(=O)CCC(N)C(O)=O QTQDDTSVRVWHMO-UHFFFAOYSA-N 0.000 claims 2
- 108700021085 S-hydroxymethylglutathione Proteins 0.000 claims 2
- 108700024212 S-methyl glutathione Proteins 0.000 claims 2
- QPBSGQWTJLPZNF-OQIRQZMPSA-N aspartyl-adenosine-5'-monophosphate Chemical compound O[C@@H]1[C@@H](O)[C@H](CO[P@](O)(=O)OC(=O)[C@H](CC(O)=O)N)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QPBSGQWTJLPZNF-OQIRQZMPSA-N 0.000 claims 2
- 229940050390 benzoate Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims 2
- 150000003840 hydrochlorides Chemical class 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims 2
- AHWSFXKKIDTZBI-QWHCGFSZSA-N s-(3-iodobenzyl)glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](C(=O)NCC(O)=O)CSCC1=CC=CC(I)=C1 AHWSFXKKIDTZBI-QWHCGFSZSA-N 0.000 claims 2
- OAWORKDPTSAMBZ-QWHCGFSZSA-N s-(p-nitrobenzyl)glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](C(=O)NCC(O)=O)CSCC1=CC=C([N+]([O-])=O)C=C1 OAWORKDPTSAMBZ-QWHCGFSZSA-N 0.000 claims 2
- 150000003890 succinate salts Chemical class 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 claims 2
- BNBLIPPJYHOAER-YNAXYJCJSA-N (1s)-1(9-deazahypoxanthin-9yl)1,4-dideoxy-1,4-imino-d-ribitol-5-phosphate Chemical compound O[C@@H]1[C@@H](O)[C@H](COP(O)(O)=O)N[C@H]1C1=CN=C2C(=O)NC=N[C]12 BNBLIPPJYHOAER-YNAXYJCJSA-N 0.000 claims 1
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
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- C07D213/65—One oxygen atom attached in position 3 or 5
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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Description
Claims (8)
SAICAR合成酵素はホスホリボシルアミノイミダゾールサクシノカルボキサミド合成酵素/ホスホリボシルアミノイミダゾールカルボキシラーゼ(PAICS)である、SAICAR合成酵素妨害剤又は抑制剤。
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CN201610865163.5 | 2016-09-29 | ||
CN201610865163 | 2016-09-29 | ||
PCT/CN2017/103408 WO2018059396A1 (zh) | 2016-09-29 | 2017-09-26 | 一类减少saicar累积的化合物及应用 |
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JP6892916B2 true JP6892916B2 (ja) | 2021-06-23 |
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EP (1) | EP3524614A4 (ja) |
JP (1) | JP6892916B2 (ja) |
WO (5) | WO2018059216A1 (ja) |
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WO2018059216A1 (zh) * | 2016-09-29 | 2018-04-05 | 广州君赫生物科技有限公司 | 降低saicar合成酶活性的化合物及应用 |
CN110678452B (zh) | 2017-04-20 | 2023-02-28 | 广州君赫生物科技有限公司 | 亚精胺及其衍生物的应用 |
WO2018192318A1 (zh) * | 2017-04-20 | 2018-10-25 | 广州君赫生物科技有限公司 | 干扰saicar合成酶活性化合物的应用 |
WO2018192293A1 (zh) | 2017-04-20 | 2018-10-25 | 广州君赫生物科技有限公司 | 精胺及其衍生物在制备抗肿瘤药物中的应用 |
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CH430712A (fr) * | 1965-06-09 | 1967-02-28 | Kogerim Ets | Procédé de préparation de formes stables et biologiquement actives des co-enzymes pyridoxiniques |
JPS5998015A (ja) * | 1982-11-27 | 1984-06-06 | Microbial Chem Res Found | 免疫賦活剤 |
CA1305425C (en) * | 1986-12-02 | 1992-07-21 | Raymond J. Bergeron | Anti-neoplastic spermine derivative |
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US8198334B2 (en) | 1997-10-27 | 2012-06-12 | Pathologica Llc | Methods for modulating macrophage proliferation in ocular disease using polyamine analogs |
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EP1492564A2 (en) * | 2001-10-31 | 2005-01-05 | Université Libre de Bruxelles | Amp-kinase agonists or adenosine pro-drugs as immuno-stimulating agents |
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EP2726480A4 (en) * | 2011-06-29 | 2014-11-19 | Oregon State | DETECTION OF ANALYTES USING FLUOROPHORES IN THE NEAR INFRARED |
FR2980709B1 (fr) | 2011-09-29 | 2013-10-25 | Nutrialys Medical Nutrition Sa | Compositions contenant de la spermine et compositions pharmaceutiques les contenant |
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WO2014067038A1 (zh) * | 2012-10-29 | 2014-05-08 | 广州百赫医疗信息科技有限公司 | 治疗人类adsl缺陷症的靶点、制剂及方法 |
CN104918611A (zh) | 2012-11-14 | 2015-09-16 | 百奥马克科技有限公司 | 用作抗癌药物化合物的亚精胺/精胺n1-乙酰基转移酶底物 |
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FR3054963B1 (fr) * | 2016-08-10 | 2018-09-14 | Assistance Publique-Hopitaux De Paris (Ap-Hp) | Utilisation d'un inhibiteur de la synthese de novo des purines, dans le traitement du deficit en adenylosuccinate lyase |
CN106399380A (zh) | 2016-09-13 | 2017-02-15 | 上海云舜生物技术有限公司 | 含抗pd‑1基因和聚亚精胺的复合物及其在治疗肿瘤中的应用 |
JP6870077B2 (ja) | 2016-09-29 | 2021-05-12 | 広州君赫生物科技有限公司 | スペルミン及びその誘導体の新たな使用 |
WO2018059216A1 (zh) | 2016-09-29 | 2018-04-05 | 广州君赫生物科技有限公司 | 降低saicar合成酶活性的化合物及应用 |
CN110678452B (zh) | 2017-04-20 | 2023-02-28 | 广州君赫生物科技有限公司 | 亚精胺及其衍生物的应用 |
WO2018192293A1 (zh) | 2017-04-20 | 2018-10-25 | 广州君赫生物科技有限公司 | 精胺及其衍生物在制备抗肿瘤药物中的应用 |
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JP2020503242A (ja) | 2020-01-30 |
WO2018059214A1 (zh) | 2018-04-05 |
EP3524614A1 (en) | 2019-08-14 |
WO2018059216A1 (zh) | 2018-04-05 |
US11766412B2 (en) | 2023-09-26 |
EP3524614A4 (en) | 2020-06-10 |
WO2018059395A1 (zh) | 2018-04-05 |
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