TWI829686B - 氧基取代化合物 - Google Patents
氧基取代化合物 Download PDFInfo
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- TWI829686B TWI829686B TW108114791A TW108114791A TWI829686B TW I829686 B TWI829686 B TW I829686B TW 108114791 A TW108114791 A TW 108114791A TW 108114791 A TW108114791 A TW 108114791A TW I829686 B TWI829686 B TW I829686B
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- TW
- Taiwan
- Prior art keywords
- oxy
- azetidin
- carboxylic acid
- hydroxy
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 632
- 150000003839 salts Chemical class 0.000 claims abstract description 215
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 494
- -1 -NR 18a R 18b Chemical group 0.000 claims description 246
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 221
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 198
- 101150047356 dec-1 gene Proteins 0.000 claims description 171
- UOQACRNTVQWTFF-UHFFFAOYSA-N decane-1,10-dithiol Chemical compound SCCCCCCCCCCS UOQACRNTVQWTFF-UHFFFAOYSA-N 0.000 claims description 158
- 125000002723 alicyclic group Chemical group 0.000 claims description 143
- 125000003118 aryl group Chemical group 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 136
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 132
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 100
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 229960004889 salicylic acid Drugs 0.000 claims description 86
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 229960004365 benzoic acid Drugs 0.000 claims description 61
- 239000005711 Benzoic acid Substances 0.000 claims description 58
- 235000010233 benzoic acid Nutrition 0.000 claims description 58
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 52
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 51
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 229910052796 boron Inorganic materials 0.000 claims description 42
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 125000004434 sulfur atom Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 16
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 229960003151 mercaptamine Drugs 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004149 thio group Chemical group *S* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 5
- DSLBDPPHINVUID-REOHCLBHSA-N (2s)-2-aminobutanediamide Chemical compound NC(=O)[C@@H](N)CC(N)=O DSLBDPPHINVUID-REOHCLBHSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- QSBRWBREBJGWIL-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(hydroxycarbamoyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(NO)=O)O QSBRWBREBJGWIL-UHFFFAOYSA-N 0.000 claims description 3
- XDBSEIDWCSYJSR-GFCCVEGCSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2R)-pyrrolidine-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@@H]1NCCC1)=O)O XDBSEIDWCSYJSR-GFCCVEGCSA-N 0.000 claims description 3
- BXXZNIPVDNUBDO-CQSZACIVSA-N 6-[1-[(2R)-2-amino-3-methylbutanoyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@H](N)C(C)C)=O)O BXXZNIPVDNUBDO-CQSZACIVSA-N 0.000 claims description 3
- PENUHZNBZVQRDH-UHFFFAOYSA-N 6-[1-[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC=1SC=C(N=1)C(C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)=NOC PENUHZNBZVQRDH-UHFFFAOYSA-N 0.000 claims description 3
- XAGVLCQFHHGATR-UHFFFAOYSA-N 6-[1-[2-[4-(2-aminoethyl)imidazol-1-yl]acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NCCC=1N=CN(C=1)CC(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O XAGVLCQFHHGATR-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000001975 deuterium Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 229960003732 tyramine Drugs 0.000 claims description 3
- NBPKEQHNTPKWAD-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperidin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1NCCCC1)=O)O NBPKEQHNTPKWAD-UHFFFAOYSA-N 0.000 claims description 2
- NCSYWEQIRPGYSA-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperidin-3-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1CNCCC1)=O)O NCSYWEQIRPGYSA-UHFFFAOYSA-N 0.000 claims description 2
- HFWQFWBWOZHICY-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1CNCC1)O HFWQFWBWOZHICY-UHFFFAOYSA-N 0.000 claims description 2
- FEVVGDPEDZWOGY-KFJBMODSSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2S)-4-hydroxypyrrolidine-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@H]1NCC(C1)O)=O)O FEVVGDPEDZWOGY-KFJBMODSSA-N 0.000 claims description 2
- ZJESARKJYPVWMY-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[4-(2-hydroxyethyl)triazol-1-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1N=NC(=C1)CCO)=O)O ZJESARKJYPVWMY-UHFFFAOYSA-N 0.000 claims description 2
- RGIDEECOJRDEJH-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[4-(methylaminomethyl)triazol-1-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1N=NC(=C1)CNC)=O)O RGIDEECOJRDEJH-UHFFFAOYSA-N 0.000 claims description 2
- NOJGRWDDAMEQMC-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[5-(methylaminomethyl)triazol-1-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1N=NC=C1CNC)=O)O NOJGRWDDAMEQMC-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- CKBISNPXVTVDMH-ZRKZCGFPSA-N 6-[(3R)-1-[2-amino-2-(1H-imidazol-5-yl)acetyl]pyrrolidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1C[C@@H](CC1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1N=CNC=1 CKBISNPXVTVDMH-ZRKZCGFPSA-N 0.000 claims description 2
- CKBISNPXVTVDMH-VPHXOMNUSA-N 6-[(3S)-1-[2-amino-2-(1H-imidazol-5-yl)acetyl]pyrrolidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1C[C@H](CC1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1N=CNC=1 CKBISNPXVTVDMH-VPHXOMNUSA-N 0.000 claims description 2
- LPXWQJVRAPHPAX-UHFFFAOYSA-N 6-[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC=1SC=C(N=1)C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O LPXWQJVRAPHPAX-UHFFFAOYSA-N 0.000 claims description 2
- CCNXEJBVTYDRAD-DRZSPHRISA-N 6-[1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound [C@H]12N[C@@H](C[C@@H]2C1)C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O CCNXEJBVTYDRAD-DRZSPHRISA-N 0.000 claims description 2
- WXZSREWBOWGWRD-CQSZACIVSA-N 6-[1-[(2R)-2-amino-2-(1H-imidazol-5-yl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@@H](C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1N=CNC=1 WXZSREWBOWGWRD-CQSZACIVSA-N 0.000 claims description 2
- IBKHDAGBSLRMAI-MRXNPFEDSA-N 6-[1-[(2R)-2-amino-3-hydroxy-2-methylpropanoyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@](N)(CO)C)=O)O IBKHDAGBSLRMAI-MRXNPFEDSA-N 0.000 claims description 2
- WXZSREWBOWGWRD-AWEZNQCLSA-N 6-[1-[(2S)-2-amino-2-(1H-imidazol-5-yl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@H](C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1N=CNC=1 WXZSREWBOWGWRD-AWEZNQCLSA-N 0.000 claims description 2
- LVBFYRGQMWOEKH-JTQLQIEISA-N 6-[1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@H](C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)CC(=O)O LVBFYRGQMWOEKH-JTQLQIEISA-N 0.000 claims description 2
- FQQKAUFMSUNNCO-JTQLQIEISA-N 6-[1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@@H](CC(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C(=O)O FQQKAUFMSUNNCO-JTQLQIEISA-N 0.000 claims description 2
- LKUNQCSLSZWHAS-NSHDSACASA-N 6-[1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@H](CC(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)CCC(=O)O LKUNQCSLSZWHAS-NSHDSACASA-N 0.000 claims description 2
- MFNHWNLZXCGQKF-UHFFFAOYSA-N 6-[1-[2-[1-(2-aminoethyl)imidazol-4-yl]acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NCCN1C=NC(=C1)CC(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O MFNHWNLZXCGQKF-UHFFFAOYSA-N 0.000 claims description 2
- AZVFBPHLUKAMFQ-UHFFFAOYSA-N 6-[1-[2-amino-2-(1,3-thiazol-4-yl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1N=CSC=1 AZVFBPHLUKAMFQ-UHFFFAOYSA-N 0.000 claims description 2
- BNYBFGIQFUJZLM-UHFFFAOYSA-N 6-[1-[2-amino-2-(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C1=C(C=C(C=C1)O)O BNYBFGIQFUJZLM-UHFFFAOYSA-N 0.000 claims description 2
- DVGHVZIRSJXUPY-UHFFFAOYSA-N 6-[1-[2-amino-2-(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C1=CC(=C(C=C1)O)O DVGHVZIRSJXUPY-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- 229960003742 phenol Drugs 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 25
- 241000009298 Trigla lyra Species 0.000 claims 6
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- IBTXYJQXMBRMHC-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-1,2,4-triazole-5-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1=NNC=N1)O IBTXYJQXMBRMHC-UHFFFAOYSA-N 0.000 claims 1
- ICAKKUIELJYNED-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(1H-imidazol-5-yl)-2-(methylamino)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C(NC)C=1N=CNC=1)=O)O ICAKKUIELJYNED-UHFFFAOYSA-N 0.000 claims 1
- YPTATZAQFRAWLH-GFCCVEGCSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[(2R)-pyrrolidin-2-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C[C@@H]1NCCC1)=O)O YPTATZAQFRAWLH-GFCCVEGCSA-N 0.000 claims 1
- YPTATZAQFRAWLH-LBPRGKRZSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[(2S)-pyrrolidin-2-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C[C@H]1NCCC1)=O)O YPTATZAQFRAWLH-LBPRGKRZSA-N 0.000 claims 1
- KGZQCIIBASIJAS-NSHDSACASA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-[(3S)-pyrrolidin-3-yl]acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C[C@H]1CNCC1)=O)O KGZQCIIBASIJAS-NSHDSACASA-N 0.000 claims 1
- ZTCFYUOEFFLUCQ-UHFFFAOYSA-N 3-(2-boronoethyl)-6-[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy-2-hydroxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C1=CC(=C(C=C1)O)O)=O)O ZTCFYUOEFFLUCQ-UHFFFAOYSA-N 0.000 claims 1
- RQHOFLGRIVRKFJ-UHFFFAOYSA-N 3-(2-boronoethyl)-6-[1-[2-(dimethylamino)-2-(1H-imidazol-5-yl)acetyl]azetidin-3-yl]oxy-2-hydroxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C(C=1N=CNC=1)N(C)C)=O)O RQHOFLGRIVRKFJ-UHFFFAOYSA-N 0.000 claims 1
- LATMVEJOCZJWKM-UHFFFAOYSA-N 6-[1-(2-amino-2-pyridin-3-ylacetyl)azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound NC(C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C=1C=NC=CC=1 LATMVEJOCZJWKM-UHFFFAOYSA-N 0.000 claims 1
- VBJHEBNKOKUEEV-QGZVFWFLSA-N 6-[1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl]oxy-3-(2-boronoethyl)-2-hydroxybenzoic acid Chemical compound N[C@@H](C(=O)N1CC(C1)OC1=CC=C(C(=C1C(=O)O)O)CCB(O)O)C1=CC=C(C=C1)O VBJHEBNKOKUEEV-QGZVFWFLSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
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| EP4049680A4 (en) * | 2019-10-25 | 2024-01-10 | Sumitomo Pharma Co., Ltd. | NEW SUBSTITUTED CONDENSED RING CONNECTION |
| US11476003B2 (en) * | 2020-12-15 | 2022-10-18 | Biodesix, Inc. | Method for predicting risk of unfavorable outcomes, e.g., in COVID-19 hospitalization, from clinical characteristics and basic laboratory findings |
| WO2024128238A1 (ja) | 2022-12-13 | 2024-06-20 | 住友ファーマ株式会社 | 細菌感染症の治療剤 |
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| US20170073360A1 (en) * | 2015-09-11 | 2017-03-16 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
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| CA2705393A1 (en) | 2007-11-13 | 2009-05-22 | Protez Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| AU2013355110B2 (en) | 2012-12-07 | 2017-11-09 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| MX2015008627A (es) | 2013-01-04 | 2015-09-23 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y usos terapeuticos de los mismos. |
| KR20150103269A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| EP2943204B1 (en) | 2013-01-10 | 2019-03-13 | Venatorx Pharmaceuticals Inc | Beta-lactamase inhibitors |
| EP2970340B1 (en) | 2013-03-14 | 2020-02-12 | Venatorx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| WO2015191907A1 (en) | 2014-06-11 | 2015-12-17 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| WO2016003929A1 (en) | 2014-07-01 | 2016-01-07 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015179308A1 (en) * | 2014-05-19 | 2015-11-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US20170073360A1 (en) * | 2015-09-11 | 2017-03-16 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
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