JP2019515906A5 - - Google Patents

Info

Publication number

JP2019515906A5

JP2019515906A5 JP2018554539A JP2018554539A JP2019515906A5 JP 2019515906 A5 JP2019515906 A5 JP 2019515906A5 JP 2018554539 A JP2018554539 A JP 2018554539A JP 2018554539 A JP2018554539 A JP 2018554539A JP 2019515906 A5 JP2019515906 A5 JP 2019515906A5

Authority

JP

Japan

Prior art keywords

compound

ethanol

vol

water

item

Prior art date

2017-04-18

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 claims description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
• 150000001875 compounds Chemical class 0.000 claims description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
• 229940126214 compound 3 Drugs 0.000 claims description 10
• 229940125782 compound 2 Drugs 0.000 claims description 9
• ZXERDUOLZKYMJM-ZWECCWDJSA-N obeticholic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(O)=O)CC[C@H]21 ZXERDUOLZKYMJM-ZWECCWDJSA-N 0.000 claims description 9
• 229960001601 obeticholic acid Drugs 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 8
• 229940125898 compound 5 Drugs 0.000 claims description 8
• 239000000203 mixture Substances 0.000 claims description 8
• -1 sodium triacetoxyborohydride Chemical compound 0.000 claims description 8
• 239000002904 solvent Substances 0.000 claims description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
• 229910000000 metal hydroxide Inorganic materials 0.000 claims description 6
• 150000004692 metal hydroxides Chemical class 0.000 claims description 6
• DXOCDBGWDZAYRQ-UHFFFAOYSA-N (3alpha,5beta)-3-Hydroxy-7-oxocholan-24 -oic acid Natural products C1CC(O)CC2CC(=O)C3C4CCC(C(CCC(O)=O)C)C4(C)CCC3C21C DXOCDBGWDZAYRQ-UHFFFAOYSA-N 0.000 claims description 4
• DXOCDBGWDZAYRQ-AURDAFMXSA-N 7-oxolithocholic acid Chemical compound C1C[C@@H](O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)CC[C@@H]3[C@]21C DXOCDBGWDZAYRQ-AURDAFMXSA-N 0.000 claims description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
• 229940125904 compound 1 Drugs 0.000 claims description 4
• 125000000468 ketone group Chemical group 0.000 claims description 4
• 150000001413 amino acids Chemical class 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 150000004703 alkoxides Chemical class 0.000 claims description 2
• 229910052987 metal hydride Inorganic materials 0.000 claims description 2
• 150000004681 metal hydrides Chemical class 0.000 claims description 2
• 229910052763 palladium Inorganic materials 0.000 claims description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
• 239000012279 sodium borohydride Substances 0.000 claims description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 2
• SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims 2
• 229960003868 paraldehyde Drugs 0.000 claims 2
• ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 229940125773 compound 10 Drugs 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
• 125000005103 alkyl silyl group Chemical group 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1