JP2017536086A5 - - Google Patents

Info

Publication number

JP2017536086A5

JP2017536086A5 JP2017515766A JP2017515766A JP2017536086A5 JP 2017536086 A5 JP2017536086 A5 JP 2017536086A5 JP 2017515766 A JP2017515766 A JP 2017515766A JP 2017515766 A JP2017515766 A JP 2017515766A JP 2017536086 A5 JP2017536086 A5 JP 2017536086A5

Authority

JP

Japan

Prior art keywords

formula

compound

ergothioneine

converting

benzyl

Prior art date

2015-09-22

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

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 claims 22
• 150000001875 compounds Chemical class 0.000 claims 11
• SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 claims 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
• 229940093497 ergothioneine Drugs 0.000 claims 6
• 150000002596 lactones Chemical class 0.000 claims 4
• 150000003462 sulfoxides Chemical class 0.000 claims 4
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 3
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 3
• 108090000790 Enzymes Proteins 0.000 claims 2
• 102000004190 Enzymes Human genes 0.000 claims 2
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 2
• 229960002885 histidine Drugs 0.000 claims 2
• 239000000543 intermediate Substances 0.000 claims 2
• NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims 2
• 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 claims 2
• 239000011589 pyridoxal 5'-phosphate Substances 0.000 claims 2
• 229960001327 pyridoxal phosphate Drugs 0.000 claims 2
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
• RAKGGEXKAWATLR-AWEZNQCLSA-N C(C1=CC=CC=C1)N1C=NC(=C1)C[C@@H](C(=O)O)N(C)C Chemical compound C(C1=CC=CC=C1)N1C=NC(=C1)C[C@@H](C(=O)O)N(C)C RAKGGEXKAWATLR-AWEZNQCLSA-N 0.000 claims 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
• 229940125797 compound 12 Drugs 0.000 claims 1
• 229940126543 compound 14 Drugs 0.000 claims 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
• 235000018417 cysteine Nutrition 0.000 claims 1
• 229910052805 deuterium Inorganic materials 0.000 claims 1
• 101150067489 egtE gene Proteins 0.000 claims 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 claims 1
• 238000005580 one pot reaction Methods 0.000 claims 1
• KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims 1
• 239000012048 reactive intermediate Substances 0.000 claims 1
• 150000003839 salts Chemical class 0.000 claims 1
• 150000003457 sulfones Chemical class 0.000 claims 1
• 230000002194 synthesizing effect Effects 0.000 claims 1
• -1 β-amino-β-carboxyethyl Chemical group 0.000 claims 1