CA2832951A1 - Glycoside derivatives and uses thereof - Google Patents
Glycoside derivatives and uses thereof Download PDFInfo
- Publication number
- CA2832951A1 CA2832951A1 CA2832951A CA2832951A CA2832951A1 CA 2832951 A1 CA2832951 A1 CA 2832951A1 CA 2832951 A CA2832951 A CA 2832951A CA 2832951 A CA2832951 A CA 2832951A CA 2832951 A1 CA2832951 A1 CA 2832951A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydro
- ylmethyl
- triol
- phenyl
- pyran
- 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.)
- Abandoned
Links
- 229930182470 glycoside Natural products 0.000 title description 3
- 150000002338 glycosides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims description 157
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 82
- -1 cyano, carboxy Chemical group 0.000 claims description 79
- 201000010099 disease Diseases 0.000 claims description 62
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 60
- 239000008103 glucose Substances 0.000 claims description 40
- 206010012601 diabetes mellitus Diseases 0.000 claims description 39
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 39
- 238000011282 treatment Methods 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 27
- 239000011734 sodium Substances 0.000 claims description 27
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 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 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 25
- 102000003673 Symporters Human genes 0.000 claims description 25
- 108090000088 Symporters Proteins 0.000 claims description 25
- 206010022489 Insulin Resistance Diseases 0.000 claims description 23
- 208000008589 Obesity Diseases 0.000 claims description 22
- 235000020824 obesity Nutrition 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 230000001404 mediated effect Effects 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- 239000000556 agonist Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 208000002249 Diabetes Complications Diseases 0.000 claims description 9
- 201000001431 Hyperuricemia Diseases 0.000 claims description 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
- 230000003247 decreasing effect Effects 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 206010012655 Diabetic complications Diseases 0.000 claims description 8
- 102000016267 Leptin Human genes 0.000 claims description 8
- 108010092277 Leptin Proteins 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 8
- 229940039781 leptin Drugs 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000000063 preceeding effect Effects 0.000 claims description 8
- 201000005665 thrombophilia Diseases 0.000 claims description 8
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 7
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 7
- 239000003472 antidiabetic agent Substances 0.000 claims description 6
- 229940030600 antihypertensive agent Drugs 0.000 claims description 6
- 239000002220 antihypertensive agent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 229940125708 antidiabetic agent Drugs 0.000 claims description 5
- 239000003524 antilipemic agent Substances 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- YBEUOGHYTJZJSE-AANPDWTMSA-N (2s,3r,4r,5s,6s)-2-[4-bromo-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methoxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](OC)O[C@H]1C1=CC=C(Br)C(CC=2C=C3CCCOC3=CC=2)=C1 YBEUOGHYTJZJSE-AANPDWTMSA-N 0.000 claims description 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 239000000883 anti-obesity agent Substances 0.000 claims description 4
- 229940125710 antiobesity agent Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 210000002824 peroxisome Anatomy 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- IHRJTDRUUVCZQP-URYYLNOGSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-chromen-6-ylmethyl)-4-ethylphenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3CCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](SC)[C@@H](O)[C@H](O)[C@H]1O IHRJTDRUUVCZQP-URYYLNOGSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- AEHNODABASDYCC-SFGZKKEESA-N (2s,3r,4r,5s)-2-[4-cyclopropyl-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)C(SC)O[C@H]1C(C=C1CC=2C=C3OCCOC3=CC=2)=CC=C1C1CC1 AEHNODABASDYCC-SFGZKKEESA-N 0.000 claims 2
- KQPKKVMQNUALJZ-SFGZKKEESA-N (2s,3r,4r,5s)-2-[4-cyclopropyl-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)C(S(=O)(=O)C)O[C@H]1C(C=C1CC=2C=C3OCCOC3=CC=2)=CC=C1C1CC1 KQPKKVMQNUALJZ-SFGZKKEESA-N 0.000 claims 2
- SVNHSSORNLNFFC-MHMIHQHRSA-N (2s,3r,4r,5s,6r)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](SC)[C@@H](O)[C@H](O)[C@H]1O SVNHSSORNLNFFC-MHMIHQHRSA-N 0.000 claims 2
- UBZOLSMWJPZVAW-MHMIHQHRSA-N (2s,3r,4r,5s,6r)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](S(C)(=O)=O)[C@@H](O)[C@H](O)[C@H]1O UBZOLSMWJPZVAW-MHMIHQHRSA-N 0.000 claims 2
- DPNGYKWDFQPJDD-URYYLNOGSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-1h-isochromen-7-ylmethyl)-4-ethylphenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3COCCC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](SC)[C@@H](O)[C@H](O)[C@H]1O DPNGYKWDFQPJDD-URYYLNOGSA-N 0.000 claims 2
- QOPPYFLJWNMCFD-URYYLNOGSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-chromen-6-ylmethyl)-4-ethylphenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3CCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](S(C)(=O)=O)[C@@H](O)[C@H](O)[C@H]1O QOPPYFLJWNMCFD-URYYLNOGSA-N 0.000 claims 2
- LOSDRIMNDSCZHF-CRSSMBPESA-N (2s,3r,4r,5s,6r)-2-[4-bromo-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C1=CC=C(Br)C(CC=2C=C3OCCOC3=CC=2)=C1 LOSDRIMNDSCZHF-CRSSMBPESA-N 0.000 claims 2
- HDPRDWAFHWYQDZ-CRSSMBPESA-N (2s,3r,4r,5s,6r)-2-[4-bromo-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C1=CC=C(Br)C(CC=2C=C3OCCOC3=CC=2)=C1 HDPRDWAFHWYQDZ-CRSSMBPESA-N 0.000 claims 2
- IJBGFWPGVZGXNI-LXHROKJGSA-N (2s,3r,4r,5s,6r)-2-[4-bromo-3-(3,4-dihydro-1h-isochromen-7-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C1=CC=C(Br)C(CC=2C=C3COCCC3=CC=2)=C1 IJBGFWPGVZGXNI-LXHROKJGSA-N 0.000 claims 2
- OOOKLKCODQCGIY-LXHROKJGSA-N (2s,3r,4r,5s,6r)-2-[4-bromo-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C1=CC=C(Br)C(CC=2C=C3CCCOC3=CC=2)=C1 OOOKLKCODQCGIY-LXHROKJGSA-N 0.000 claims 2
- ZESDKPBSGTUJEB-LXHROKJGSA-N (2s,3r,4r,5s,6r)-2-[4-bromo-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C1=CC=C(Br)C(CC=2C=C3CCCOC3=CC=2)=C1 ZESDKPBSGTUJEB-LXHROKJGSA-N 0.000 claims 2
- VEDPAGZYFBVLCR-WJGLBBAVSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C(C=C1CC=2C=C3CCCOC3=CC=2)=CC=C1C1CC1 VEDPAGZYFBVLCR-WJGLBBAVSA-N 0.000 claims 2
- DMIYYZYNHGNGOF-WJGLBBAVSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C(C=C1CC=2C=C3CCCOC3=CC=2)=CC=C1C1CC1 DMIYYZYNHGNGOF-WJGLBBAVSA-N 0.000 claims 2
- TXBOUBXIPJLUOP-VROINQGHSA-N (2s,3r,4r,5s,6s)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-methoxyoxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](OC)[C@@H](O)[C@H](O)[C@H]1O TXBOUBXIPJLUOP-VROINQGHSA-N 0.000 claims 2
- HTYYMVLKDBNCRI-DJCPXJLLSA-N (2s,3r,4r,5s,6s)-2-[3-(3,4-dihydro-2h-chromen-6-ylmethyl)-4-ethylphenyl]-6-methoxyoxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3CCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](OC)[C@@H](O)[C@H](O)[C@H]1O HTYYMVLKDBNCRI-DJCPXJLLSA-N 0.000 claims 2
- QJCUUUNTUODNMU-DJCPXJLLSA-N (2s,3r,4r,5s,6s)-2-[4-cyclopropyl-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]-6-methoxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](OC)O[C@H]1C(C=C1CC=2C=C3OCCOC3=CC=2)=CC=C1C1CC1 QJCUUUNTUODNMU-DJCPXJLLSA-N 0.000 claims 2
- NSLGINRGCYYCSH-VAFBSOEGSA-N (2s,3r,4r,5s,6s)-2-[4-cyclopropyl-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-methoxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](OC)O[C@H]1C(C=C1CC=2C=C3CCCOC3=CC=2)=CC=C1C1CC1 NSLGINRGCYYCSH-VAFBSOEGSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- AHNUPEPMZYOZOJ-VKINHPFQSA-N (2S,3R,4R,5S,6S)-2-[3-(1-azatricyclo[6.2.2.02,7]dodeca-2(7),3,5-trien-4-ylmethyl)-4-cyclopropylphenyl]-6-methoxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](OC)O[C@H]1C(C=C1CC=2C=C3N4CCC(CC4)C3=CC=2)=CC=C1C1CC1 AHNUPEPMZYOZOJ-VKINHPFQSA-N 0.000 claims 1
- VMQBMVWRMIVBKR-PUHDZGQXSA-N (2r,3s,4r,5r,6s)-2-methylsulfanyl-6-[4-(oxetan-3-yl)-3-(2,3,4,5-tetrahydro-1-benzoxepin-7-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C(C=C1CC=2C=C3CCCCOC3=CC=2)=CC=C1C1COC1 VMQBMVWRMIVBKR-PUHDZGQXSA-N 0.000 claims 1
- XLSGZJAUNKOMGV-PUHDZGQXSA-N (2r,3s,4r,5r,6s)-2-methylsulfonyl-6-[4-(oxetan-3-yl)-3-(2,3,4,5-tetrahydro-1-benzoxepin-7-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C(C=C1CC=2C=C3CCCCOC3=CC=2)=CC=C1C1COC1 XLSGZJAUNKOMGV-PUHDZGQXSA-N 0.000 claims 1
- WNIGLAWVLPSXHF-VBRJGFDYSA-N (2s,3r,4r,5s)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-(2,2,2-trifluoroethylsulfonyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1[C@@H]1OC(S(=O)(=O)CC(F)(F)F)[C@@H](O)[C@H](O)[C@H]1O WNIGLAWVLPSXHF-VBRJGFDYSA-N 0.000 claims 1
- VQTPUFFKNVOVIX-BCNYOWNLSA-N (2s,3r,4r,5s)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-phenylsulfanyloxane-3,4,5-triol Chemical compound O([C@H]([C@@H]([C@@H](O)[C@@H]1O)O)C2=CC=C(C(=C2)CC=2C=C3OCCOC3=CC=2)CC)C1SC1=CC=CC=C1 VQTPUFFKNVOVIX-BCNYOWNLSA-N 0.000 claims 1
- YURDOSVVRFSGLH-APQRZRNDSA-N (2s,3r,4r,5s)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-thiophen-2-ylsulfonyloxane-3,4,5-triol Chemical compound O([C@H]([C@@H]([C@@H](O)[C@@H]1O)O)C2=CC=C(C(=C2)CC=2C=C3OCCOC3=CC=2)CC)C1S(=O)(=O)C1=CC=CS1 YURDOSVVRFSGLH-APQRZRNDSA-N 0.000 claims 1
- XULSVENVVXPVLX-MHMIHQHRSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(2,3,4,5-tetrahydro-1-benzoxepin-7-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3CCCCOC3=CC=2)=C1 XULSVENVVXPVLX-MHMIHQHRSA-N 0.000 claims 1
- SDBSVCVOTJCEJO-IONQDRQYSA-N (2s,3r,4r,5s,6r)-2-[4-cyclobutyl-3-(2,3,4,5-tetrahydro-1-benzothiepin-7-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C(C=C1CC=2C=C3CCCCSC3=CC=2)=CC=C1C1CCC1 SDBSVCVOTJCEJO-IONQDRQYSA-N 0.000 claims 1
- LGQADQXUQFSUTR-URYJJRPLSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopentyl-3-(2,3,4,5-tetrahydro-1-benzoxepin-7-ylmethyl)phenyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](SC)O[C@H]1C(C=C1CC=2C=C3CCCCOC3=CC=2)=CC=C1C1CCCC1 LGQADQXUQFSUTR-URYJJRPLSA-N 0.000 claims 1
- JCKODGXIGQLFCZ-URYJJRPLSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopentyl-3-(2,3,4,5-tetrahydro-1-benzoxepin-7-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C(C=C1CC=2C=C3CCCCOC3=CC=2)=CC=C1C1CCCC1 JCKODGXIGQLFCZ-URYJJRPLSA-N 0.000 claims 1
- OHAKZWILHJMJOG-WJGLBBAVSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(1,2,3,4-tetrahydroquinolin-7-ylmethyl)phenyl]-6-methylsulfonyloxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](S(=O)(=O)C)O[C@H]1C(C=C1CC=2C=C3NCCCC3=CC=2)=CC=C1C1CC1 OHAKZWILHJMJOG-WJGLBBAVSA-N 0.000 claims 1
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- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201161475493P | 2011-04-14 | 2011-04-14 | |
| US61/475,493 | 2011-04-14 | ||
| PCT/IB2012/051798 WO2012140596A1 (en) | 2011-04-14 | 2012-04-12 | Glycoside derivatives and uses thereof |
Publications (1)
| Publication Number | Publication Date |
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| CA2832951A1 true CA2832951A1 (en) | 2012-10-18 |
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Family Applications (1)
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| CA2832951A Abandoned CA2832951A1 (en) | 2011-04-14 | 2012-04-12 | Glycoside derivatives and uses thereof |
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| Country | Link |
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| US (1) | US8722633B2 (enExample) |
| EP (1) | EP2697240B1 (enExample) |
| JP (1) | JP2014510782A (enExample) |
| KR (1) | KR20140019834A (enExample) |
| CN (1) | CN103619862A (enExample) |
| AU (1) | AU2012241426A1 (enExample) |
| BR (1) | BR112013026361A2 (enExample) |
| CA (1) | CA2832951A1 (enExample) |
| EA (1) | EA201391524A1 (enExample) |
| MX (1) | MX2013011926A (enExample) |
| WO (1) | WO2012140596A1 (enExample) |
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| ES2719656T3 (es) | 2011-06-01 | 2019-07-11 | Green Cross Corp | Derivados de difenilmetano novedosos como inhibidores del SGLT2 |
| TR201908247T4 (tr) * | 2012-11-20 | 2019-06-21 | Lexicon Pharmaceuticals Inc | Sodyum glikoz birlikte taşıyıcı 1 inhibitörleri. |
| US9394329B2 (en) | 2013-09-27 | 2016-07-19 | Sunshine Lake Pharma Co., Ltd. | Glucopyranosyl derivatives and their uses in medicine |
| HUE053645T2 (hu) | 2013-11-18 | 2021-07-28 | Forma Therapeutics Inc | Tetrahidrokinolin kompozíciók mint BET bromodomén inhibitorok |
| RU2720237C2 (ru) | 2013-11-18 | 2020-04-28 | Форма Терапеутикс, Инк. | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет |
| SG11201810701XA (en) | 2016-06-02 | 2018-12-28 | Sanofi Sa | Conjugates of a pharmaceutical agent and a moiety capable of binding to a glucose sensing protein |
| EP4249479A4 (en) * | 2020-11-19 | 2024-12-18 | Beijing Increase Innovative Drug Co., Ltd. | GLUCOSIDE DERIVATIVE, ITS PREPARATION METHOD AND ITS APPLICATION |
| WO2022223480A1 (en) * | 2021-04-18 | 2022-10-27 | Ecole Polytechnique Federale De Lausanne (Epfl) | Green solvents for chemical reactions |
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| CN1020944C (zh) | 1990-01-30 | 1993-05-26 | 阿图尔-费希尔股份公司费希尔厂 | 紧固件 |
| IL148384A0 (en) | 1999-08-31 | 2002-09-12 | Kissei Pharmaceutical | Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| DE60115623T2 (de) | 2000-03-17 | 2006-07-06 | Kissei Pharmaceutical Co., Ltd., Matsumoto | Glucopyranosyloxy-benzylbenzen-derivate, medizinische zusammensetzung und zwischenprodukte für die herstellung der derivate |
| US6683056B2 (en) | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| KR100647204B1 (ko) | 2000-09-29 | 2006-11-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 글루코피라노실옥시벤질벤젠 유도체 및 그것을 함유하는의약조성물 |
| US6936590B2 (en) * | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| EP1432720A1 (en) | 2001-09-05 | 2004-06-30 | Bristol-Myers Squibb Company | O-pyrazole glucoside sglt2 inhibitors and method of use |
| TW200303742A (en) | 2001-11-21 | 2003-09-16 | Novartis Ag | Organic compounds |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| DE10231370B4 (de) | 2002-07-11 | 2006-04-06 | Sanofi-Aventis Deutschland Gmbh | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| JP2004137245A (ja) | 2002-08-23 | 2004-05-13 | Kissei Pharmaceut Co Ltd | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| ES2363941T3 (es) | 2003-03-14 | 2011-08-19 | Astellas Pharma Inc. | Derivados de c-glucósido para el tratamiento de diabetes. |
| AU2003902263A0 (en) | 2003-05-12 | 2003-05-29 | Fujisawa Pharmaceutical Co., Ltd. | Monosaccharide compounds |
| US7652061B2 (en) | 2003-05-20 | 2010-01-26 | Novartis A.G. | N-acyl nitrogen heterocycles as ligands of peroxisome proliferator-activated receptors |
| ES2402098T5 (es) * | 2003-08-01 | 2021-06-09 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador dependiente de sodio |
| EP1680414A4 (en) | 2003-08-01 | 2009-05-27 | Janssen Pharmaceutica Nv | SUBSTITUTED INDAZOLE-O-GLUCOSIDE |
| EP1660509B1 (de) | 2003-08-26 | 2009-02-04 | Boehringer Ingelheim International GmbH | Glucopyranosyloxy-pyrazole, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| NZ549219A (en) | 2004-03-04 | 2010-08-27 | Kissei Pharmaceutical | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| AU2005219779B2 (en) | 2004-03-04 | 2011-04-14 | Kissei Pharmaceutical Co., Ltd. | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| US7393836B2 (en) | 2004-07-06 | 2008-07-01 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
| DE102004034690A1 (de) | 2004-07-17 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Methyliden-D-xylopyranosyl-und Oxo-D-xylopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| JP2008508213A (ja) | 2004-07-27 | 2008-03-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｄ−グルコピラノシル−フェニル置換環状体、そのような化合物を含有する医薬品、それらの使用及びその製造方法 |
| WO2006018150A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| DE102004048388A1 (de) | 2004-10-01 | 2006-04-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| JP5086643B2 (ja) | 2004-11-18 | 2012-11-28 | キッセイ薬品工業株式会社 | １−置換−３−（β−Ｄ−グリコピラノシル）含窒素ヘテロ環化合物、及びそれを含有する医薬 |
| US20080027014A1 (en) | 2006-07-28 | 2008-01-31 | Tanabe Seiyaku Co., Ltd. | Novel SGLT inhibitors |
| TW200817424A (en) | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| KR101352934B1 (ko) * | 2009-06-19 | 2014-02-19 | 주식회사 녹십자 | 신규 ｃ―아릴 글루코사이드 ｓｇｌｔ２ 억제제 및 이를 포함하는 약학 조성물 |
| US8163704B2 (en) * | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
-
2012
- 2012-04-12 EP EP12719082.5A patent/EP2697240B1/en active Active
- 2012-04-12 KR KR1020137029814A patent/KR20140019834A/ko not_active Withdrawn
- 2012-04-12 JP JP2014504431A patent/JP2014510782A/ja active Pending
- 2012-04-12 BR BR112013026361A patent/BR112013026361A2/pt not_active IP Right Cessation
- 2012-04-12 EA EA201391524A patent/EA201391524A1/ru unknown
- 2012-04-12 US US13/634,597 patent/US8722633B2/en active Active
- 2012-04-12 AU AU2012241426A patent/AU2012241426A1/en not_active Abandoned
- 2012-04-12 CN CN201280028538.2A patent/CN103619862A/zh active Pending
- 2012-04-12 WO PCT/IB2012/051798 patent/WO2012140596A1/en not_active Ceased
- 2012-04-12 CA CA2832951A patent/CA2832951A1/en not_active Abandoned
- 2012-04-12 MX MX2013011926A patent/MX2013011926A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012140596A1 (en) | 2012-10-18 |
| KR20140019834A (ko) | 2014-02-17 |
| EA201391524A1 (ru) | 2014-04-30 |
| JP2014510782A (ja) | 2014-05-01 |
| CN103619862A (zh) | 2014-03-05 |
| EP2697240B1 (en) | 2015-09-16 |
| BR112013026361A2 (pt) | 2016-12-27 |
| EP2697240A1 (en) | 2014-02-19 |
| WO2012140596A8 (en) | 2013-05-30 |
| AU2012241426A1 (en) | 2013-10-31 |
| US8722633B2 (en) | 2014-05-13 |
| US20130203975A1 (en) | 2013-08-08 |
| MX2013011926A (es) | 2013-11-01 |
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Effective date: 20160413 |