HRP20120627T1 - Glukopiranozil-supstituirani derivati benzola, lijekovi koji sadrže te spojeve, njihova uporaba i postupak njihove proizvodnje - Google Patents
Glukopiranozil-supstituirani derivati benzola, lijekovi koji sadrže te spojeve, njihova uporaba i postupak njihove proizvodnje Download PDFInfo
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- HRP20120627T1 HRP20120627T1 HRP20120627TT HRP20120627T HRP20120627T1 HR P20120627 T1 HRP20120627 T1 HR P20120627T1 HR P20120627T T HRP20120627T T HR P20120627TT HR P20120627 T HRP20120627 T HR P20120627T HR P20120627 T1 HRP20120627 T1 HR P20120627T1
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- Prior art keywords
- alkyl
- substituted
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- group
- aryl
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- 150000001875 compounds Chemical class 0.000 title claims 39
- 229940079593 drug Drugs 0.000 title claims 13
- 239000003814 drug Chemical class 0.000 title claims 13
- 238000000034 method Methods 0.000 title claims 9
- 238000004519 manufacturing process Methods 0.000 title claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims 3
- -1 hydroxy, amino Chemical group 0.000 claims abstract 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 25
- 239000001257 hydrogen Substances 0.000 claims abstract 25
- 125000003118 aryl group Chemical group 0.000 claims abstract 23
- 239000011737 fluorine Substances 0.000 claims abstract 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 17
- 239000000460 chlorine Substances 0.000 claims abstract 17
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 17
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 11
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims abstract 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims abstract 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract 2
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims abstract 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract 2
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract 2
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims abstract 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 150000001555 benzenes Chemical class 0.000 claims 26
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical group 0.000 claims 11
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 125000004036 acetal group Chemical group 0.000 claims 8
- 239000013543 active substance Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 6
- 239000000969 carrier Substances 0.000 claims 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 5
- 239000005977 Ethylene Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000000532 dioxanyl group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 150000003214 pyranose derivatives Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- OJJZXSLECGJTKR-GNADVCDUSA-N (2r,3r,4s,5s,6r)-2-[4-chloro-3-[(4-cyclopentyloxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(Cl)C(CC=2C=CC(OC3CCCC3)=CC=2)=C1 OJJZXSLECGJTKR-GNADVCDUSA-N 0.000 claims 3
- YZGOOQZXQOPQNT-JEOSHJBNSA-N (2r,3r,4s,5s,6r)-2-[4-chloro-3-[[4-[(3r)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(Cl)C(CC=2C=CC(O[C@H]3COCC3)=CC=2)=C1 YZGOOQZXQOPQNT-JEOSHJBNSA-N 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- UTPWWZOQLPABOK-GNADVCDUSA-N (2R,3R,4S,5S,6R)-2-[4-chloro-3-[(4-piperidin-4-yloxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCNCC3)cc2)c1 UTPWWZOQLPABOK-GNADVCDUSA-N 0.000 claims 2
- KBFKNUPRTJGGGF-YMQHIKHWSA-N (2r,3r,4s,5s,6r)-2-[3-[(4-ethynylphenyl)methyl]-4-fluorophenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(F)C(CC=2C=CC(=CC=2)C#C)=C1 KBFKNUPRTJGGGF-YMQHIKHWSA-N 0.000 claims 2
- GXGRVEFOJXINFI-YMQHIKHWSA-N (2r,3r,4s,5s,6r)-2-[4-chloro-3-[(4-ethynylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(Cl)C(CC=2C=CC(=CC=2)C#C)=C1 GXGRVEFOJXINFI-YMQHIKHWSA-N 0.000 claims 2
- YZGOOQZXQOPQNT-DNNBANOASA-N (2r,3r,4s,5s,6r)-2-[4-chloro-3-[[4-[(3s)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(Cl)C(CC=2C=CC(O[C@@H]3COCC3)=CC=2)=C1 YZGOOQZXQOPQNT-DNNBANOASA-N 0.000 claims 2
- OMAFUSRFORDFLA-NHTNDUFYSA-N (2r,3r,4s,5s,6r)-6-(hydroxymethyl)-2-[4-methyl-3-[[4-(2-trimethylsilylethyl)phenyl]methyl]phenyl]oxane-2,3,4,5-tetrol Chemical compound CC1=CC=C([C@]2(O)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC1=CC=C(CC[Si](C)(C)C)C=C1 OMAFUSRFORDFLA-NHTNDUFYSA-N 0.000 claims 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- GXBMVHQRCMRFCQ-WSGIOKLISA-N CC(=O)N1CCC(CC1)Oc1ccc(Cc2cc(ccc2Cl)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 Chemical compound CC(=O)N1CCC(CC1)Oc1ccc(Cc2cc(ccc2Cl)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 GXBMVHQRCMRFCQ-WSGIOKLISA-N 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- SFZDSAWRWKXPOH-PDYRQOBPSA-N Cc1ccc(cc1Cc1ccc(OC2CCOC2)cc1)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O Chemical compound Cc1ccc(cc1Cc1ccc(OC2CCOC2)cc1)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SFZDSAWRWKXPOH-PDYRQOBPSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- WXYNATOYTSYKGF-XNBWIAOKSA-N OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCC3)cc2)c1 Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCC3)cc2)c1 WXYNATOYTSYKGF-XNBWIAOKSA-N 0.000 claims 2
- YRNCKDWNAQXBIU-NHTNDUFYSA-N OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCCCC3)cc2)c1 Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCCCC3)cc2)c1 YRNCKDWNAQXBIU-NHTNDUFYSA-N 0.000 claims 2
- FVYDFXIPFBNLGQ-ZDAQNSFHSA-N OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCOC3=O)cc2)c1 Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCOC3=O)cc2)c1 FVYDFXIPFBNLGQ-ZDAQNSFHSA-N 0.000 claims 2
- OZDYIJWUIDUOMQ-GNADVCDUSA-N OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCOCC3)cc2)c1 Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(Cl)c(Cc2ccc(OC3CCOCC3)cc2)c1 OZDYIJWUIDUOMQ-GNADVCDUSA-N 0.000 claims 2
- ZUGUABJOHCSGCZ-YMQHIKHWSA-N OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1cccc(Cc2ccc(cc2)C#C)c1 Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1cccc(Cc2ccc(cc2)C#C)c1 ZUGUABJOHCSGCZ-YMQHIKHWSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 150000003855 acyl compounds Chemical class 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 229940030600 antihypertensive agent Drugs 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
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- 239000002552 dosage form Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 150000002902 organometallic compounds Chemical class 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- IMVDZFOSXJSXFP-UHFFFAOYSA-N 5-chloro-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbaldehyde Chemical compound CCCC1=NC(Cl)=C(C=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 IMVDZFOSXJSXFP-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
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- OWYCBAUNJISMHN-QMCAAQAGSA-N COc1ccc(cc1Cc1ccc(cc1)C#C)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O Chemical compound COc1ccc(cc1Cc1ccc(cc1)C#C)[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OWYCBAUNJISMHN-QMCAAQAGSA-N 0.000 claims 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
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- Rheumatology (AREA)
Abstract
Glukopiranozil-supstituirani derivati benzola, naznačeni time, da imaju opću formulu I gdje R1 je odabran između sljedećih značenja: vodik, fluor, klor, brom, jod, C1-4-alkil, C2-6-alkinil, C1-4-alkoksi, C2-4-alkenil-C1-4-alkoksi, C2-4-alkinil-C1-4-alkoksi, metil supstituiran s 1 do 3 atoma fluora, etil supstituiran s 1 do 5 atoma fluora, metoksi supstituiran s 1 do 3 atoma fluora, etoksi supstituiran s 1 do 5 atoma fluora, C1-4-alkil supstituiran s hidroksi- ili C1-3-alkoksi-skupinom, C2-4-alkoksi supstituiran s hidroksi- ili C1-3-alkoksi-skupinom, C2-6-alkenil, C3-6-cikloalkil, C3-6-cikloalkil-C1-3-alkil, C3-7-cikloalkiloksi, C3-6-cikloalkil-C1-3-alkoksi, C5-7-cikloalkeniloksi, hidroksi, amino, nitro ili cijano, dok se u C5-6-cikloalkil-skupinama može zamijeniti metilen-skupina s O, R2 označava vodik, fluor, klor, brom, hidroksi, C1-4-alkil,C1-4-alkoksi, cijano ili nitro, dok alkil- ili alkoksi-skupina može biti mono- ili poli-supstituirana s fluorom, i R3 je odabran od sljedećih značenja: tri-(C1-4-alkil)silil-C1-6-alkil, C2-6-alkin-1-il, C2-6-alken-1-il, amino, C1-3-alkilamino, di-(C1-3-alkil)amino, pirolidin-1-il, pirolidin-2-on-1-il, piperidin-1-il, piperidin-2-on-1-il, morfolin-4-il, morfolin-3-on-4-il, piperazin-1-il, 4-(C1-3-alkil)piperazin-1-il, nitro, C3-7-cikloalkiloksi, C5-7-cikloalkeniloksi, C3-7-cikloalkilsulfanil, C3-7-cikloalkilsulfinil, C3-7-cikloalkilsulfonil, C5-7-cikloalkenilsulfanil, C5-7-cikloalkenilsulfinil i C5-7-cikloalkenilsulfonil, dok gore navedene alkinil- i alkenil-skupine mogu biti mono- ili poli-supstituirane s fluorom ili klorom, poželjno s fluorom, i gdje gore navedene alkinil- i alkenil-skupine mogu biti mono-ili di-supstituirane s istim ili različitim skupinama L1; pri čemu gore navedeni cikloalkilni i cikloalkenilni prsteni međusobno neovisno mogu biti mono- ili di-supstituirani supstituentima odabranima od fluora i C1-3-alkila, i dok u gore navedenim cikloalkilnim i cikloalkenilnim prstenima, jedna ili dvije metilen-skupine mogu biti zamijenjene međusobno neovisno s O, S, CO, SO, SO2 ili NRN, poželjno s O, CO, S, SO2 ili NRN, najbolje s O ili CO, R4, R5 međusobno neovisno označavaju vodik, fluor, klor, brom, jod, cijano, nitro, C1-3-alkil, C1-3-alkoksi, metil ili metoksi supstituiran s 1 do 3 atoma fluora, RN označava H, C1-4-alkil, C1-4-alkilkarbonil ili C1-4-alkilsulfonil, L1 međusobno neovisno su odabrane između sljedećih: hidroksi-, cijano-, nitro-, C3-7-cikloalkil-, aril-, heteroaril-, C1-4-alkilkarbonil-, arilkarbonil-, heteroarilkarbonil-, aminokarbonil-, C1-4-alkilaminokarbonil-, di-(C1-3-alkil)aminokarbonil-, pirolidin-1-ilkarbonil-, piperidin-1-ilkarbonil-,morfolin-4-ilkarbonil, arilaminokarbonil-, heteroarilaminokarbonil-,C1-4-alkoksikarbonil-, aril-C1-3-alkoksikarbonil-, heteroaril-C1-3-alkoksikarbonil-, C1-4-alkiloksi-, ariloksi-, heteroariloksi-, C1-4-alkilsulfanil-, arilsulfanil-, heteroarilsulfanil-, C1-4-alkilsulfinil-, arilsulfinil-, heteroarilsulfinil-, C1-4-alkilsulfonil-, arilsulfonil-
Claims (47)
1. Glukopiranozil-supstituirani derivati benzola, naznačeni time, da imaju opću formulu I
[image]
gdje
R1 je odabran između sljedećih značenja: vodik, fluor, klor, brom, jod,
C1-4-alkil, C2-6-alkinil, C1-4-alkoksi, C2-4-alkenil-C1-4-alkoksi, C2-4-alkinil-
C1-4-alkoksi, metil supstituiran s 1 do 3 atoma fluora, etil supstituiran s 1 do 5 atoma fluora, metoksi supstituiran s 1 do 3 atoma fluora, etoksi supstituiran s 1 do 5 atoma fluora, C1-4-alkil supstituiran s hidroksi- ili
C1-3-alkoksi-skupinom, C2-4-alkoksi supstituiran s hidroksi- ili C1-3-alkoksi-skupinom, C2-6-alkenil, C3-6-cikloalkil, C3-6-cikloalkil-C1-3-alkil,
C3-7-cikloalkiloksi, C3-6-cikloalkil-C1-3-alkoksi, C5-7-cikloalkeniloksi, hidroksi, amino, nitro ili cijano, dok se u C5-6-cikloalkil-skupinama može zamijeniti metilen-skupina s O,
R2 označava vodik, fluor, klor, brom, hidroksi, C1-4-alkil,C1-4-alkoksi, cijano ili nitro, dok alkil- ili alkoksi-skupina može biti mono- ili poli-supstituirana s fluorom, i
R3 je odabran od sljedećih značenja: tri-(C1-4-alkil)silil-C1-6-alkil, C2-6-alkin-1-il, C2-6-alken-1-il, amino, C1-3-alkilamino, di-(C1-3-alkil)amino, pirolidin-1-il, pirolidin-2-on-1-il, piperidin-1-il, piperidin-2-on-1-il, morfolin-4-il, morfolin-3-on-4-il, piperazin-1-il, 4-(C1-3-alkil)piperazin-1-il, nitro,
C3-7-cikloalkiloksi, C5-7-cikloalkeniloksi, C3-7-cikloalkilsulfanil,
C3-7-cikloalkilsulfinil, C3-7-cikloalkilsulfonil, C5-7-cikloalkenilsulfanil,
C5-7-cikloalkenilsulfinil i C5-7-cikloalkenilsulfonil, dok gore navedene alkinil- i alkenil-skupine mogu biti mono- ili poli-supstituirane s fluorom ili klorom, poželjno s fluorom, i
gdje gore navedene alkinil- i alkenil-skupine mogu biti mono-ili di-supstituirane s istim ili različitim skupinama L1;
pri čemu gore navedeni cikloalkilni i cikloalkenilni prsteni međusobno neovisno mogu biti mono- ili di-supstituirani supstituentima odabranima od fluora i C1-3-alkila, i dok u gore navedenim cikloalkilnim i cikloalkenilnim prstenima, jedna ili dvije metilen-skupine mogu biti zamijenjene međusobno neovisno s O, S, CO, SO, SO2 ili NRN, poželjno s O, CO, S, SO2 ili NRN, najbolje s O ili CO,
R4, R5 međusobno neovisno označavaju vodik, fluor, klor, brom, jod, cijano, nitro, C1-3-alkil, C1-3-alkoksi, metil ili metoksi supstituiran s 1 do 3 atoma fluora, RN označava H, C1-4-alkil, C1-4-alkilkarbonil ili
C1-4-alkilsulfonil,
L1 međusobno neovisno su odabrane između sljedećih: hidroksi-, cijano-,
nitro-, C3-7-cikloalkil-, aril-, heteroaril-, C1-4-alkilkarbonil-, arilkarbonil-, heteroarilkarbonil-, aminokarbonil-, C1-4-alkilaminokarbonil-,
di-(C1-3-alkil)aminokarbonil-, pirolidin-1-ilkarbonil-, piperidin-1-ilkarbonil-,
morfolin-4-ilkarbonil, arilaminokarbonil-, heteroarilaminokarbonil-,
C1-4-alkoksikarbonil-, aril-C1-3-alkoksikarbonil-, heteroaril-C1-3-alkoksikarbonil-, C1-4-alkiloksi-, ariloksi-, heteroariloksi-, C1-4-alkilsulfanil-, arilsulfanil-, heteroarilsulfanil-, C1-4-alkilsulfinil-, arilsulfinil-, heteroarilsulfinil-, C1-4-alkilsulfonil-, arilsulfonil- i heteroaril-sulfonil-; i
L2 međusobno neovisno su odabrane između sljedećih: fluor, klor, brom, jod, C1-3-alkil, difluorometil, trifluorometil, C1-3-alkoksi, difluorometoksi, trifluorometoksi i cijano; i
R6 označava vodik, (C1-6-alkil)oksikarbonil ili C1-6-alkilkarbonil,
R7a, R7b, R7c označavaju vodik,
dok se pod aril-skupinama navedenima u definiciji gornjih skupina misli na fenil- ili naftil-skupine koje mogu biti mono- ili di-supstituirane međusobno neovisno s istim ili različitim skupinama L2; i
pod heteroaril-skupinama navedenima u definiciji gornjih skupina, misli se na pirolil-, furanil-, tienil-, piridil-, indolil-, benzofuranil-, benzotiofenil-, kinolinil-, izokinolinil- ili tetrazolil-skupina, ili se misli na pirolil-, furanil-, tienil- ili piridil-skupinu, gdje su jedna ili dvije metin-skupine zamijenjene s atomima dušika, ili se misli na indolil-, benzofuranil-, benzotiofenil-, kinolinil- ili izokinolinil-skupinu, gdje su jedna do tri metin-skupine zamijenjene s atomima dušika, dok gore navedene heteroaril-skupine međusobno neovisno mogu biti mono- ili di-supstituirane s istim ili različitim skupinama L2;
pri čemu, ako nije drugačije rečeno, gore navedene alkil-skupine mogu biti ravnolančane ili razgranate,
njiihovi tautomeri, stereoizomeri, njihove mješavine te njihove soli.
2. Glukopiranozil-supstituirani derivati benzola, naznačeni time, da imaju opću formulu 1.2
[image]
gdje su skupine R1 do R6 te R7a, R7b i R7c definirane u zahtjevu 1.
3. Glukopiranozil-supstituirani derivati benzola, naznačeni time, da imaju opću formulu 1.2c
[image]
gdje su skupine R1 do R6 te R7a, R7b i R7c definirane u zahtjevu 1.
4. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 3, naznačeni time, da je skupina R1 odabrana između sljedećih značenja: vodik, fluor, klor, brom, cijano, metil, etil, izopropil, difluorometil, trifluorometil, etinil, prop-1-in-1-il, but-1-in-1-il, hidroksi, metoksi, etoksi, difluorometoksi, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi.
5. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 1, 2 ili 3, naznačeni time, da je skupina R1 odabrana između sljedećih značenja: metil i klor.
6. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 5, naznačeni time, da je skupina R3 odabrana između sljedećih značenja: tri-(C1-4-alkil)silil-C1-6-alkil, C2-6-alkin-1-il, C2-6-alken-1-il, C3-7-cikloalkiloksi, C5-7-cikloalkeniloksi, C3-7-cikloalkilsulfanil, C5-7-cikloalkenilsulfanil, gdje gore navedene alkinil- i alkenil-skupine mogu biti mono- ili poli-supstituirane s fluorom ili mono-supstituirane s klorom ili skupinom L1, pri čemu u cikloalkil- i cikloalkenil-skupinama jedna ili dvije metilen-skupine mogu biti zamijenjene međusobno neovisno s O, CO, S, SO2ili NRN, posebno s O ili CO, a L1 i RNsu definirane u zahtjevu 1.
7. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 5, naznačeni time, da je skupina R3 odabrana između sljedećih značenja: trimetilsililetil, etinil, 1-propin-1-il, 1-butin-1-il, tert. butiletinil, 2-hidroksiprop-2-iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi-1-propin-1-il, 3-metoksi-1-propin-1-il, etenil, 1-propenil, 1-butenil, tert.-butiletenil, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuraniloksi, tetrahidrotiofeniloksi, 1,1-dioksotetrahidrotiofeniloksi, tetrahidropiraniloksi, tetrahidrotiopiraniloksi, 1,1-dioksotetrahidrotiopiraniloksi, tetrahidrofuranoniloksi, piperidiniloksi, piperidinoniloksi, pirolidin-3-iloksi, pirolidinon-3-iloksi, tetrahidrofuranil-sulfanil, ciklopropilsulfanil, ciklobutilsulfanil, ciklopentilsulfanil i cikloheksilsulfanil, dok –NH skupina u piperidinilnom, piperidinonilnom, pirolidinilnom ili pirolidinonilnom prstenu, može biti supstituirana s C1-3-alkilom ili acetilom.
8. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 5, naznačeni time, da je skupina R3 odabrana između sljedećih značenja: trimetilsililetil, etinil, 2-hidroksiprop-2-iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi-1-propin-1-il, 3-metoksi-1-propin-1-il, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi, tetrahidropiran-4-iloksi, piperidin-4-iloksi, N-metilpiperidin-4-iloksi i N-acetilpiperidin-4-iloksi.
9. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 5, naznačeni time, da je skupina R3 odabrana između sljedećih značenja: etinil, trimetilsililetil, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi i tetrahidropiran-4-iloksi.
10. Glukopiranozil-supstituirani derivati benzola prema jednom ili više zahtjeva od 1 do 9, naznačeni time, da skupina R2 označava vodik, fluor, klor, brom, metil, hidroksi, metoksi, etoksi, trifluorometoksi, cijano, nitro ili metil supstituiran s 1 do 3 atoma fluora.
11. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 10, naznačeni time, da skupina R2 označava vodik ili metil.
12. Glukopiranozil-supstituirani derivati benzola prema jednom od zahtjeva 1 do 11, naznačeni time, da skupine R4 i/ili R5 međusobno neovisno označavaju vodik ili fluor.
13. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 12, naznačeni time, da skupina R4 označava vodik.
14. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 12, naznačeni time, da skupina R5 označava vodik.
15. Glukopiranozil-supstituirani derivati benzola prema jednom od zahtjeva 1 do 13, naznačeni time, da skupina R6 označava vodik.
16. Glukopiranozil-supstituirani derivati benzola prema jednom od zahtjeva 1, 2, 3, 4 ili 10, naznačeni time, da skupina RN označava H, metil, etil ili acetil.
17. Glukopiranozil-supstituirani derivati benzola prema jednom ili više od zahtjeva 1 do 16, naznačeni time, da je skupina L1 odabrana između sljedećih: hidroksi-, cijano-, C3-6-cikloalkil, C1-4-alkilkarbonil-, aminokarbonil-, C1-4-alkilaminokarbonil-, di-(C1-3-alkil)aminokarbonil-, pirolidin-1-ilkarbonil-, piperidin-1-ilkarbonil-, morfolin-4-ilkarbonil-, C1-4-alkoksikarbonil-, C1-4-alkiloksi-, C1-4-alkilsulfanil-, C1-4-alkilsulfinil- i C1-4-alkilsulfonil-.
18. Glukopiranozil-supstituirani derivati benzola prema jednom ili više od zahtjeva 1 do 16, naznačeni time, da je skupina L1 odabrana između sljedećih: hidroksi-, C1-4-alkiloksi- i C1-4-alkilsulfanil-.
19. Glukopiranozil-supstituirani derivati benzola prema jednom ili više od zahtjeva 1 do 18, naznačeni time, da su odabrani između sljedećih spojeva (1) do (8), (10) do (15) i (17):
(1) 1-kloro-2-(4-ciklopentiloksibenzil)-4-(β-D-glukopiranoz-1-il)-benzol
(2) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-((R)-tetrahidrofuran-3-iloksi)-benzil]-benzol
(3) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-((S)-tetrahidrofuran-3-iloksi)-benzil]-benzol
(4) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-(tetrahidrofuran-2-on-3-iloksi)-benzil]-benzol
(5) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-(4-ciklobutiloksi-benzil)-benzol
(6) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-(4-cikloheksiloksi-benzil)-benzol
(7) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-(tetrahidropiran-4-iloksi)-benzil]-benzol
(8) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-(1-acetil-piperidin-4-iloksi)-benzil]-benzol
(10) 1-(β-D-glukopiranoz-1-il)-4-metil-3-[4-(tetrahidrofuran-3-iloksi)-benzil]-benzol
(11) 1-(β-D-glukopiranoz-1-il)-4-metil-3-[4-(2-trimetilsilil-etil)-benzil]-benzol
(12) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-(4-etinil-benzil)-benzol
(13) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-(piperidin-4-iloksi)-benzil]-benzol
(14) 1-fluoro-4-(β-D-glukopiranoz-1-il)-2-(4-etinil-benzil)-benzol
(15) 1-(β-D-glukopiranoz-1-il)-3-(4-etinil-benzil)-benzol
(17) 1-metoksi-4-(β-D-glukopiranoz-1-il)-2-(4-etinil-benzil)-benzol.
20. Glukopiranozil-supstituirani derivat benzola prema zahtjevu 19, naznačen time, da glukopiranozil-supstituirani derivat benzola je spoj (2): (2) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-((R)-tetrahidrofuran-3-iloksi)-benzil]-benzol.
21. Glukopiranozil-supstituirani derivat benzola prema zahtjevu 19, naznačen time, da glukopiranozil-supstituirani derivat benzola je spoj (3): (3) 1-kloro-4-(β-D-glukopiranoz-1-il)-2-[4-((S)-tetrahidrofuran-3-iloksi)-benzil]-benzol.
22. Fiziološki prihvatljiva sol, naznačena time, da je od spojeva prema barem jednom od zahtjeva 1 do 21, s anorganskim ili organskim kiselinama.
23. Lijek, naznačen time, da sadrži spoj prema barem jednom od zahtjeva 1 do 21, ili fiziološki prihvatljivu sol prema zahtjevu 22, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
24. Uporaba barem jednog spoja prema barem jednom od zahtjeva 1 do 21, ili fiziološki prihvatljive soli prema zahtjevu 22, naznačena time, da je za proizvodnju lijeka koji je pogodan za liječenje ili prevenciju metaboličkih poremećaja odabranih između sljedećih: dijabetes mellitus tip 1 i tip 2, komplikacije kod dijabetesa, metabolička acidoza ili ketoza, reaktivna hipoglikemija, hiperinsulinemija, metabolički poremećaj glukoze, otpornost na inzulin, metabolički sindrom, dislipidemija različitih izvora, ateroskleroza i s njom povezane bolesti, pretilost, povišeni krvni tlak, kronično zatajenje srca, edem i hiperurikemija.
25. Uporaba prema zahtjevu 24, naznačena time, da je metabolički poremećaj odabran između dijabetesa mellitus tip 1 i tip 2, te komplikacija kod dijabetesa.
26. Uporaba barem jednog spoja prema barem jednom od zahtjeva 1 do 21, ili fiziološki prihvatljive soli prema zahtjevu 22, naznačena time, da je za proizvodnju lijeka za inhibiranje natrij-ovisnog prijenosnika glukoze SGLT2.
27. Uporaba barem jednog spoja prema barem jednom od zahtjeva 1 do 21, ili fiziološki prihvatljive soli prema zahtjevu 22, naznačena time, da je za proizvodnju lijeka za prevenciju degeneracije beta stanica gušterače i/ili za poboljšanje i/ili obnavljanje funkcionalnosti beta stanica gušterače.
28. Uporaba barem jednog spoja prema barem jednom od zahtjeva 1 do 21, ili fiziološki prihvatljive soli prema zahtjevu 22, naznačena time, da je za proizvodnju diuretika i/ili antihipertenziva.
29. Postupak proizvodnje spojeva opće formule I prema zahtjevima 1 do 21, naznačen time, da spoj opće formule II
[image]
gdje
R’ označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, dok alkil- ili aril-skupine mogu biti mono- ili poli-supstituirane s halogenom;
R8a , R8b, R8c, R8d su međusobno neovisno odabrani između sljedećih: vodik, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označavaju benzil-skupinu ili RaRbRcSi-skupinu ili ketal- ili acetal-skupinu, dok u svakom slučaju dvije susjedne skupine R8a, R8b, R8c, R8d mogu tvoriti ciklički ketal- ili acetal-skupinu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilen-most, pri čemu gore navedeni etilen-most, zajedno s dva atoma kisika i dva pridružena atoma ugljika od piranoznog prstena, tvori supstituirani dioksanski prsten, a alkil-, aril- i/ili benzil-skupine mogu biti mono- ili poli-supstituirane s halogenom ili C1-3-alkoksi, a benzil-skupine mogu biti također supstituirane s di-(C1-3-alkil)amino-skupinom; i
Ra, Rb, Rc međusobno neovisno označavaju C1-4-alkil, aril ili aril-C1-3-alkil, gdje aril- ili alkil-skupine mogu biti mono- ili poli-supstituirane s halogenom;
pri čemu se pod aril-skupinama navedenima u definiciji gornjih skupina, misli na fenil- ili naftil-skupine, poželjno fenil-skupine;
i R1 do R5 imaju značenja dana u zahtjevima 1 do 21,
reagira s reduktivnim sredstvom u prisutnosti Lewis-ove ili Brønsted-ove kiseline, dok se bilo koja prisutna zaštitna skupina istovremeno ili naknadno rascijepi; po želji se tako dobiveni spoj opće formule I, gdje R6 označava atom vodika, pretvori pomoću acilacije u odgovarajući acilni spoj opće formule I, i/ili ako je to potrebno, bilo koja zaštitna skupina, korištena u gore opisanim reakcijama se rascijepi, i/ili po želji se tako dobiveni spoj opće formule I, rastopi u svojim stereoizomerima, i/ili po želji se tako dobiveni spoj opće formule I, pretvori u svoje fiziološki prihvatljive soli.
30. Postupak prema zahtjevu 29, naznačen time, da se spoj opće formule II dobiva postupkom opisanim u zahtjevu 31 ili 32.
31. Postupak proizvodnje spojeva opće formule II
[image]
,
naznačen time, da
R’ označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonil, gdje alkil- ili aril-skupine mogu biti mono- ili poli-supstituirane s halogenom;
R8a , R8b, R8c, R8d su međusobno neovisno odabrane između sljedećih: vodik,
(C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označavaju benzil-skupinu ili RaRbRcSi-skupinu ili ketal- ili acetal-skupinu, pri čemu u svakom slučaju dvije susjedne skupine R8a, R8b, R8c, R8dmogu tvoriti cikličku ketal- ili acetal-skupinu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilen-most, dok gore navedeni etilen-most, zajedno s dva atoma kisika i dva pridružena atoma ugljika od piranoznog prstena, tvori supstituirani dioksanski prsten, i gdje alkil-, aril- i/ili benzil-skupine mogu biti mono- ili poli-supstituirane s halogenom, ili C1-3-alkoksi, a benzil-skupine mogu također biti supstituirane s
-di-(C1-3-alkil)amino-skupinom; i
Ra, Rb, Rc međusobno neovisno označavaju C1-4-alkil, aril, ili aril-C1-3-alkil, gdje aril- ili alkil-skupine mogu biti mono- ili poli-supstituirane s halogenom;
dok se za aril-skupine spomenute u definiciji gore navedenih skupina misli na fenil- ili naftil-skupine, poželjno na fenil-skupine;te R1 do R5 imaju značenja dana u zahtjevima 1 do 21,
pri čemu se organometalni spoj (V), koji se može dobiti izmjenom halogen-metal ili umetanjem metala u vezu ugljik-halogen od spoja halogen-benzilbenzol opće formule IV
[image]
gdje Hal označava Cl, Br i I, a R1 do R5 su ovdje prethodno definirane, te se opcijski vrši naknadna transmetalacija,
dodaje u glukonolakton opće formule VI
[image]
gdje su R8a, R8b, R8c, R8d ovdje prethodno definirani,
i
tada dobiveni prinos reagira s vodom ili alkoholom R’-OH, gdje R’ označava opcijski supstituirani C1-4-alkil, u prisutnosti kiseline te opcijski, proizvod dobiven u reakciji s vodom, gdje R’ označava H, pretvara se u naknadnoj reakciji s acilacijskim sredstvom u proizvod formule II, gdje R’ označava (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonil, koji mogu biti supstituirani kako je naznačeno.
32. Postupak prema zahtjevu 31, naznačen time, da organometalni spoj (V) je spoj litija ili magnezija.
33. Postupak proizvodnje spojeva opće formule I prema zahtjevima 1 do 21, gdje R6 označava vodik, naznačen time, da se spoj opće formule III
[image]
gdje
su R8a, R8b, R8c, R8d međusobno neovisno odabrani između sljedećih: vodik, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ali barem jedna od skupina R8a, R8b, R8c, R8d ne označava vodik, ili označava benzil-skupinu ili RaRbRcSi-skupinu ili ketal- ili acetal-skupinu, dok u svakom slučaju dvije susjedne skupine R8a, R8b, R8c, R8d mogu tvoriti cikličku ketal- ili acetal-skupinu ili
1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilen-most, pri čemu gore navedeni etilen-most tvori supstituirani dioksanski prsten zajedno s dva atoma kisika i pridružena dva atoma ugljika od piranoznog prstena, i gdje alkil-, aril- i/ili benzil-skupine mogu biti mono- ili poli-supstituirane s halogenom ili C1-3-alkoksi te benzil-skupine također mogu biti supstituirane s di-(C1-3-alkil)amino-skupinom; i
Ra, Rb, Rcmeđusobno neovisno predstavljaju C1-4-alkil, aril ili aril-C1-3-alkil, dok alkil- ili aril-skupine mogu biti mono- ili poli-supstituirane s halogenom;
gdje se pod aril-skupinama spomenutima u definiciji gore navedenih skupina misli na fenil- ili naftil-skupine, poželjno fenil-skupine; i
R1 do R5 imaju značenja dana u zahtjevima 1 do 21,
hidrolizira, i ako je poželjno, tako dobiveni spoj opće formule I, gdje R6 označava atom vodika, pretvara se pomoću acilacije u odgovarajući acilni spoj opće formule I,
i/ili ako je potrebno, bilo koja zaštitna skupina korištena u gore opisanim reakcijama se rascijepi,
i/ili ako je poželjno, tako dobiveni spoj opće formule I se rastopi u svojim stereoizomerima,
i/ili ako je poželjno, tako dobiveni spoj opće formule I se pretvara u svoje soli, posebno za farmaceutsku uporabu u svoje fiziološki prihvatljive soli.
34. Postupak prema zahtjevu 33, naznačen time, da se spoj formule III dobiva postupkom prema zahtjevu 29 ili 30.
35. Spoj, naznačen time, da ima opću formulu IV
[image]
gdje Hal označava klor, brom ili jod i
R1 označava vodik, fluor, klor, brom, cijano, metil, etil, izopropil, difluorometil, trifluorometil, etinil, prop-1-in-1-il, but-1-in-1-il, hidroksi, metoksi, etoksi, difluorometoksi, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi ili cikloheksiloksi; i
R2 označava vodik ili metil; i
R3 je odabran između sljedećih: trimetilsililetil, etinil, 2-hidroksiprop-2-iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi-1-propin-1-il, 3-metoksi-1-propin-1-il, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi, tetrahidropiran-4-iloksi, piperidin-4-iloksi, N-metilpiperidin-4-iloksi i N-acetilpiperidin-4-iloksi; i
R4 označava vodik ili fluor; i
R5 označava vodik ili fluor.
36. Spoj formule IV prema zahtjevu 35, naznačen time, da ima formulu IV'
[image]
gdje Hal označava klor, brom ili jod, a skupine R1, R2, R3, R4 i R5 su definirane u zahtjevu 35.
37. Spoj, naznačen time, da ima opću formulu II
[image]
gdje
R’ označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonil, gdje alkil- ili aril-skupine mogu biti mono- ili poli-supstituirane s halogenom;
R8a, R8b, R8e, R8d međusobno neovisno su odabrani između sljedećih: vodik, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označavaju benzil-skupinu ili RaRbRcSi-skupinu ili ketal- ili acetal-skupinu, dok u svakom slučaju dvije susjedne skupine od R8a, R8b, R8c, R8d mogu tvoriti cikličku ketal- ili acetal-skupinu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilen-most, pri čemu gore navedeni etilen-most tvori supstituirani dioksanski prsten zajedno s dva atoma kisika i dva pridružena atoma ugljika od piranoznog prstena, te alkil-, aril- i/ili benzil-skupine mogu biti mono- ili poli-supstituirane s halogenom ili C1-3-alkoksi, a benzil-skupine mogu također biti supstituirane s di-(C1-3-alkil)amino-skupinom; i
Ra, Rb, Rc međusobno neovisno označavaju C1-4-alkil, aril ili aril-C1-3-alkil, dok alkil- ili aril-skupine mogu biti mono- ili poli-supstituirane s halogenom; gdje se pod aril-skupinama spomenutima u definiciji gore navedenih skupina, misli na fenil- ili naftil-skupine, poželjno fenil-skupine;
te su R1 do R5 definirani u jednom ili više od zahtjeva 1 i 4 do 14.
38. Glukopiranozil-supstituirani derivati benzola opće formule I
[image]
naznačeni time, da su R1 do R5 definirani u jednom ili više od zahtjeva 1 do 21, i
R6, R7a, R7b, R7c međusobno neovisno imaju značenje odabrano između sljedećih: (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, L2 su međusobno neovisno odabrani između sljedećih: fluor, klor, brom, jod, C1-3-alkil, difluorometil, trifluorometil, C1-3-alkoksi, difluorometoksi, trifluorometoksi i cijano; i
pod aril-skupinama spomenutima u definiciji gore navedenih skupina, misli se na fenil- ili naftil-skupine koje mogu biti mono- ili di-supstituirane međusobno neovisno s istim ili različitim skupinama L2; i ako nije drugačije rečeno, gore navedene alkil-skupine mogu biti ravnolančane ili razgranate,
njihovi tautomeri, stereoizomeri i njihove mješavine te njihove soli.
39. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 38, naznačeni time, da imaju opću formulu 1.2
[image]
gdje su R1 do R5 i R6, R7a, R7b, R7c definirani u zahtjevu 38.
40. Glukopiranozil-supstituirani derivati benzola prema zahtjevu 38, naznačeni time, da imaju opću formulu 1.2c
[image]
gdje su R1 do R5 i R6, R7a, R7b, R7c definirani u zahtjevu 38.
41. Lijek, naznačen time, da sadrži spoj prema jednom ili više od zahtjeva 1 do 21 ili fiziološki prihvatljivu sol takvog spoja i najmanje jednu aktivnu tvar odabranu između antidijabetičkih sredstava, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
42. Lijek, naznačen time, da sadrži spoj prema jednom ili više od zahtjeva 1 do 21 ili fiziološki prihvatljivu sol takvog spoja i najmanje jednu aktivnu tvar odabranu između sljedećih: inhibitori proteina tirozinfosfataze 1, tvari koje imaju učinak na nereguliranu proizvodnju glukoze u jetri, kao što su primjerice inhibitori glukoza-6-fosfataze, ili fruktoza-1,6-bisfosfataze, glikogen fosforilaze, antagonisti glukagon receptora i inhibitori karboksikinaze fosfoenol piruvata, kinaze sinteze glikogena ili dehidrokinaze piruvata, sredstva za smanjenje lipida kao što su primjerice inhibitori HMG-CoA-reduktaze, fibrati, nikotinska kiselina i njihovi derivati, PPAR-alfa agonisti, PPAR-delta agonisti, ACAT inhibitori ili inhibitori apsorpcije kolesterola, tvari vezanja žučne kiselina, inhibitori transporta ilealne žučne kiseline, spojevi za HDL-porast kao što su CETP inhibitori ili ABC1 regulatori ili aktivne tvari za liječenje pretilosti, kao što su sibutramin ili tetrahidrolipostatin, deksfenfluramin, aksokin, antagonisti receptora kanabinoid1, antagonisti receptora MCH-1, agonisti receptora MC4, NPI5 ili NPI2 antagonisti ili ß3-agonisti i agonisti receptora 5HT2c, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
43. Lijek, naznačen time, da sadrži spoj prema jednom ili više od zahtjeva 1 do 21 ili fiziološki prihvatljivu sol takvog spoja i najmanje jednu aktivnu tvar odabranu između lijekova koji imaju utjecaj na visoki krvni tlak, kronično zatajenje srca ili aterosklerozu kao što su primjerice A-II antagonisti ili ACE inhibitori, ECE inhibitori, diuretici, ß-blokatori, Ca-antagonisti, antihipertenzivi koji djeluju centralno, antagonisti receptora alfa-2-adrenergika, inhibitori neutralne endopeptidaze, te inhibitori agregacije trombocita ili njihove kombinacije, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
44. Lijek prema zahtjevu 43, naznačen time, da je aktivna tvar odabrana između antagonista receptora angiotenzina II koji su odabrani između sljedećih: kandesartan cileksetil, kalijev losartan, eprosartan mesilat, valsartan, telmisartan, irbesartan, EXP-3174, L-158809, EXP-3312, olmesartan, medoksomil, tasosartan, KT-3-671, GA-0113, RU-64276, EMD-90423, BR-9701.
45. Lijek, naznačen time, da sadrži spoj prema jednom ili više od zahtjeva 1 do 21 ili fiziološki prihvatljivu sol takvog spoja i najmanje jednu aktivnu tvar odabranu između inhibitora sinteze urične kiseline i urikozurika, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
46. Lijek, naznačen time, da sadrži spoj prema jednom ili više od zahtjeva 1 do 21 ili fiziološki prihvatljivu sol takvog spoja i najmanje jednu aktivnu tvar odabranu između sljedećih: antagonisti GABA-receptora, blokatori Na-kanala, topiramat, inhibitori protein-kinaze C, inhibitori krajnjeg proizvoda napredovanja glikacije i inhibitori reduktaze aldoze, opcijski zajedno s jednim ili više inertnih nosača i/ili razrjeđivača.
47. Lijek prema jednom od zahtjeva 41 do 46, naznačen time, da spoj prema izumu, ili njegova fiziološki prihvatljiva sol, te dodatna aktivna tvar koja se sastavlja s njima, nalaze se zajedno u jednom dozirnom obliku ili odvojeno u dva ista ili različita dozirna oblika.
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| DE102004012676A DE102004012676A1 (de) | 2004-03-16 | 2004-03-16 | Glucopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE102004040168A DE102004040168A1 (de) | 2004-08-18 | 2004-08-18 | Glucopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE102004061145A DE102004061145A1 (de) | 2004-12-16 | 2004-12-16 | Glucopyranosyl-substituierte Benzol-Derivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
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| PCT/EP2005/002618 WO2005092877A1 (de) | 2004-03-16 | 2005-03-11 | Glucopyranosyl-substituierte benzol-derivate, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
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| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| CA2557801C (en) * | 2004-03-16 | 2013-06-25 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production 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 |
| 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 |
| 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 |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| US7687469B2 (en) | 2004-12-16 | 2010-03-30 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
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