RU2564661C2 - Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ - Google Patents
Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ Download PDFInfo
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- RU2564661C2 RU2564661C2 RU2012129930/04A RU2012129930A RU2564661C2 RU 2564661 C2 RU2564661 C2 RU 2564661C2 RU 2012129930/04 A RU2012129930/04 A RU 2012129930/04A RU 2012129930 A RU2012129930 A RU 2012129930A RU 2564661 C2 RU2564661 C2 RU 2564661C2
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- 150000001467 thiazolidinediones Chemical class 0.000 title abstract description 9
- 208000030159 metabolic disease Diseases 0.000 title abstract description 7
- 101150014691 PPARA gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 293
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 24
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229940126062 Compound A Drugs 0.000 claims description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 16
- 239000000126 substance Substances 0.000 abstract description 16
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 12
- 208000008589 Obesity Diseases 0.000 abstract description 10
- 235000020824 obesity Nutrition 0.000 abstract description 10
- 230000004770 neurodegeneration Effects 0.000 abstract description 6
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 6
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
- -1 methoxy, ethoxy Chemical group 0.000 description 121
- 125000001931 aliphatic group Chemical group 0.000 description 108
- 125000000217 alkyl group Chemical group 0.000 description 100
- 235000002639 sodium chloride Nutrition 0.000 description 91
- 150000003839 salts Chemical class 0.000 description 77
- 239000000243 solution Substances 0.000 description 73
- 125000001072 heteroaryl group Chemical group 0.000 description 72
- 235000019439 ethyl acetate Nutrition 0.000 description 71
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 125000003118 aryl group Chemical group 0.000 description 61
- 239000011541 reaction mixture Substances 0.000 description 59
- 125000003545 alkoxy group Chemical group 0.000 description 54
- 239000000203 mixture Substances 0.000 description 54
- 229910052736 halogen Inorganic materials 0.000 description 48
- 150000002367 halogens Chemical class 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 45
- 239000011734 sodium Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- 238000002360 preparation method Methods 0.000 description 39
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 37
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 34
- 108010016731 PPAR gamma Proteins 0.000 description 32
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 32
- 239000012267 brine Substances 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- 239000000047 product Substances 0.000 description 31
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- 239000013078 crystal Substances 0.000 description 30
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 125000004043 oxo group Chemical group O=* 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 19
- 229910004373 HOAc Inorganic materials 0.000 description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 19
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- 125000003368 amide group Chemical group 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 125000002619 bicyclic group Chemical group 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 229960001948 caffeine Drugs 0.000 description 14
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 125000002252 acyl group Chemical group 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000004913 activation Effects 0.000 description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
- 125000003435 aroyl group Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 125000004104 aryloxy group Chemical group 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
- YAUMOGALQJYOJQ-UHFFFAOYSA-N 5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC(C(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 YAUMOGALQJYOJQ-UHFFFAOYSA-N 0.000 description 10
- IRNJSRAGRIZIHD-UHFFFAOYSA-N 5-[[4-[2-(5-ethyl-2-pyridinyl)-2-oxoethoxy]phenyl]methyl]thiazolidine-2,4-dione Chemical compound N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 IRNJSRAGRIZIHD-UHFFFAOYSA-N 0.000 description 10
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- 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 description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
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- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 8
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- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
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- 201000010099 disease Diseases 0.000 description 7
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- 108020001756 ligand binding domains Proteins 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
- 0 OC(C(Cc(cc1)ccc1OC*c1cc(C(F)(F)F)ccc1)S1)NC1=O Chemical compound OC(C(Cc(cc1)ccc1OC*c1cc(C(F)(F)F)ccc1)S1)NC1=O 0.000 description 6
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- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Obesity (AREA)
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- Neurosurgery (AREA)
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- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| US28676509P | 2009-12-15 | 2009-12-15 | |
| US61/286,765 | 2009-12-15 | ||
| PCT/US2010/060439 WO2011084453A1 (en) | 2009-12-15 | 2010-12-15 | Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases |
Publications (2)
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| RU2012129930A RU2012129930A (ru) | 2014-01-27 |
| RU2564661C2 true RU2564661C2 (ru) | 2015-10-10 |
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| RU2012129930/04A RU2564661C2 (ru) | 2009-12-15 | 2010-12-15 | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ |
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|---|---|
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| EP (1) | EP2513070B1 (OSRAM) |
| JP (1) | JP5634526B2 (OSRAM) |
| KR (3) | KR20120107493A (OSRAM) |
| CN (1) | CN102753539B (OSRAM) |
| AU (1) | AU2010340055B2 (OSRAM) |
| CA (1) | CA2783468C (OSRAM) |
| DK (1) | DK2513070T3 (OSRAM) |
| ES (1) | ES2658168T3 (OSRAM) |
| HU (1) | HUE038042T2 (OSRAM) |
| MX (1) | MX2012006725A (OSRAM) |
| NO (1) | NO2513070T3 (OSRAM) |
| NZ (1) | NZ600390A (OSRAM) |
| PL (1) | PL2513070T3 (OSRAM) |
| RU (1) | RU2564661C2 (OSRAM) |
| WO (1) | WO2011084453A1 (OSRAM) |
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| HUE038042T2 (hu) | 2009-12-15 | 2018-09-28 | Cirius Therapeutics Inc | PPAR helyettesítõ tiazolidindion sók metabolikus betegségek kezelésére |
| UA116217C2 (uk) | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
| PT2934568T (pt) | 2012-12-21 | 2018-01-04 | Sanofi Sa | Agonistas duplos de glp1/gip ou trigonais de glp1/gip/glucagina |
| MX2016000724A (es) * | 2013-07-22 | 2016-04-13 | Metabolic Solutions Dev Co Llc | Compuestos de reserva de los receptores activados del proliferador de peroxisoma (ppar) para el tratamiento de enfermedades metabolicas. |
| TW201609795A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 作為雙重ｇｌｐ－１／ｇｉｐ受體促效劑的艾塞那肽－４（ｅｘｅｎｄｉｎ－４）胜肽類似物 |
| TW201609797A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 雙重ｇｌｐ－１／升糖素受體促效劑 |
| TW201609799A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 雙重ｇｌｐ－１／ｇｉｐ受體促效劑 |
| TW201609796A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 非醯化之艾塞那肽－４（ｅｘｅｎｄｉｎ－４）胜肽類似物 |
| TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重ｇｌｐ－１／昇糖素受體激動劑之艾塞那肽－４衍生物 |
| TW201625669A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自艾塞那肽－４（Ｅｘｅｎｄｉｎ－４）之肽類雙重ＧＬＰ－１／升糖素受體促效劑 |
| TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自ｅｘｅｎｄｉｎ－４之雙重ｇｌｐ－１／升糖素受體促效劑 |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
| TW201706291A (zh) | 2015-07-10 | 2017-02-16 | 賽諾菲公司 | 作為選擇性肽雙重ｇｌｐ－１／升糖素受體促效劑之新毒蜥外泌肽（ｅｘｅｎｄｉｎ－４）衍生物 |
| US20210038566A1 (en) | 2018-02-08 | 2021-02-11 | Enyo Pharma | Use of modulators of neet proteins for the treatment of infection |
| CN111689934B (zh) * | 2020-06-24 | 2022-08-02 | 郑州大学 | 14-脱羟-13-脱氢穿心莲内酯-12-磺酸钾的单晶体及制备方法 |
| GB202210503D0 (en) | 2022-07-18 | 2022-08-31 | Univ Court Univ Of Glasgow | Materials and methods for treatment of chronic myeloid leukemia (CML) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155845A1 (en) * | 1984-03-21 | 1985-09-25 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| EP0193256A1 (en) * | 1985-01-19 | 1986-09-03 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| RU2323004C2 (ru) * | 1995-06-20 | 2008-04-27 | Такеда Фармасьютикал Компани Лимитед | Фармацевтическая композиция |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| WO1985004170A1 (fr) | 1984-03-21 | 1985-09-26 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, leur procede de preparation et compositions medicinales les contenant |
| WO1986002073A1 (fr) | 1984-10-03 | 1986-04-10 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant |
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| US5167228A (en) | 1987-06-26 | 1992-12-01 | Brigham And Women's Hospital | Assessment and modification of endogenous circadian phase and amplitude |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5143930A (en) | 1990-02-07 | 1992-09-01 | Sankyo Company, Limited | Thiazolidine derivatives with anti-diabetic activity, their preparation and their use |
| US5356913A (en) | 1990-02-09 | 1994-10-18 | The Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| US5441971A (en) | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| CA2106967C (en) * | 1991-04-11 | 2003-12-09 | Takashi Sohda | Thiazolidinedione derivatives, production and use thereof |
| NO302471B1 (no) | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| NZ286920A (en) | 1995-07-03 | 1997-06-24 | Sankyo Co | Use of combination of hmg-coa reductase inhibitors and of insulin sensitizers for the prevention/treatment of arteriosclerosis or xanthoma |
| US7407978B2 (en) | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| CA2371391A1 (en) | 1999-04-29 | 2000-11-09 | City Of Hope | Pentoxifylline, pioglitazone and metformin are inhibitors of formation of advanced glycation endproducts (age's) |
| US6331596B1 (en) | 1999-06-28 | 2001-12-18 | Basf Corporation | Method of preparing carbamate-functional polymers |
| DK1192137T3 (da) | 1999-06-30 | 2013-11-11 | Amgen Inc | Forbindelser til modulering af PPAR-gamma aktivitet |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| AU2002226365A1 (en) | 2000-12-01 | 2002-06-11 | Novartis Ag | Combinations of an angiotensin receptor antagonist and an anti-hypertensive drug or a statin, for the treatment of sexual dysfunction |
| US7009057B2 (en) | 2001-04-26 | 2006-03-07 | Zentiva A.S. | Method for obtaining pioglitazone as an antidiabetic agent |
| US7135485B2 (en) | 2001-09-28 | 2006-11-14 | Teva Pharmaceutical Industries Ltd. | Pioglitazone hydrochloride |
| AUPS236902A0 (en) | 2002-05-16 | 2002-06-13 | Northern Sydney Area Health Service | Composition and method for treating hypertension |
| WO2004007490A2 (en) * | 2002-07-16 | 2004-01-22 | Cadila Healthcare Limited | A process to prepare pioglitazone via several intermediates. |
| US20060083784A1 (en) | 2002-08-07 | 2006-04-20 | Smithkline Beecham Corporation | Amorphous pharmaceutical compositions |
| US7230016B2 (en) * | 2003-05-13 | 2007-06-12 | Synthon Ip Inc. | Pioglitazone salts, such as pioglitazone sulfate, and pharmaceutical compositions and processes using the same |
| US20070078170A1 (en) | 2003-08-28 | 2007-04-05 | Khanduri Chandra H | Process for the preparation of pioglitazone |
| AR047541A1 (es) | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
| JP4475983B2 (ja) * | 2004-03-03 | 2010-06-09 | 学校法人日本大学 | Ｂｍａｌ１を阻害する方法 |
| US7777038B2 (en) | 2004-09-28 | 2010-08-17 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compound |
| CA2646170A1 (en) | 2006-03-16 | 2007-09-27 | Metabolic Solutions Development Company | Combination therapies of thiazolidinedione analogues and glucocorticoid agonists |
| RU2445957C2 (ru) | 2006-03-16 | 2012-03-27 | Метаболик Солюшнз Девелопмент Компани | Аналоги тиазолидиндиона |
| JP5149271B2 (ja) | 2006-03-16 | 2013-02-20 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 高血圧症を処置するためならびに脂質を下げるためのチアゾリジンジオン類似体 |
| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| AU2008301905B2 (en) | 2007-09-14 | 2013-06-27 | Cirius Therapeutics, Inc. | Thiazolidinedione analogues for the treatment of hypertension |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| NZ590774A (en) | 2008-08-07 | 2012-09-28 | Pulmagen Therapeutics Inflammation Ltd | Substantially pure 5R enantiomers of pioglitazone and rosiglitazone for treating inflammatory respiratory diseases |
| WO2010105048A1 (en) | 2009-03-12 | 2010-09-16 | Metabolic Solutions Development Company | Thiazolidinedione analogues |
| WO2011017244A1 (en) | 2009-08-05 | 2011-02-10 | Metabolic Solutions Development Company | Polymorphs of 5-(4-(2-(5-ethylpyridin-2-yl)-2-oxoethoxy)benzyl)-1,3-thiazolidine-2,4-dione (mitoglitazone) |
| HUE038042T2 (hu) | 2009-12-15 | 2018-09-28 | Cirius Therapeutics Inc | PPAR helyettesítõ tiazolidindion sók metabolikus betegségek kezelésére |
| NZ600421A (en) | 2009-12-15 | 2014-06-27 | Metabolic Solutions Dev Co Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| AU2010340058A1 (en) | 2009-12-15 | 2012-06-21 | Metabolic Solutions Development Company, Llc | PPAR-sparing thiazolidinediones and combinations for the treatment of diabetes mellitus and other metabolic diseases |
| KR20120092714A (ko) | 2009-12-15 | 2012-08-21 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 비만 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 |
| EP2560615A1 (en) | 2010-04-21 | 2013-02-27 | Metabolic Solutions Development Company LLC | Thiazolidinedione analogues |
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2010
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- 2010-12-15 AU AU2010340055A patent/AU2010340055B2/en active Active
- 2010-12-15 PL PL10796247T patent/PL2513070T3/pl unknown
- 2010-12-15 MX MX2012006725A patent/MX2012006725A/es active IP Right Grant
- 2010-12-15 CA CA2783468A patent/CA2783468C/en active Active
- 2010-12-15 RU RU2012129930/04A patent/RU2564661C2/ru active
- 2010-12-15 KR KR1020127018388A patent/KR20120107493A/ko not_active Ceased
- 2010-12-15 KR KR1020177010102A patent/KR102029560B1/ko active Active
- 2010-12-15 KR KR1020187022229A patent/KR102029611B1/ko active Active
- 2010-12-15 WO PCT/US2010/060439 patent/WO2011084453A1/en not_active Ceased
- 2010-12-15 NZ NZ600390A patent/NZ600390A/xx unknown
- 2010-12-15 NO NO10796247A patent/NO2513070T3/no unknown
- 2010-12-15 CN CN201080063893.4A patent/CN102753539B/zh active Active
- 2010-12-15 US US13/515,508 patent/US8912335B2/en active Active
- 2010-12-15 ES ES10796247.4T patent/ES2658168T3/es active Active
- 2010-12-15 EP EP10796247.4A patent/EP2513070B1/en active Active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155845A1 (en) * | 1984-03-21 | 1985-09-25 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| EP0193256A1 (en) * | 1985-01-19 | 1986-09-03 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| RU2323004C2 (ru) * | 1995-06-20 | 2008-04-27 | Такеда Фармасьютикал Компани Лимитед | Фармацевтическая композиция |
Non-Patent Citations (4)
| Title |
|---|
| KULKARNI SANTOSH S. et al.: "Three-dimensional quantitative structure activity relationships (3-D-QSAR) of antihyperglycemic agents", BIOORGANIC & MEDICINAL CHEMISTRY, 1999, vol.7, p.1475-1485. * |
| SOHDA T. et al: "Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones", ARZNEIMITTEL-FORSCHUNG, DRUG RESEARCH, 1990, vol.40, no.1, p.37-42. * |
| STEPHEN M.BERGE et al.: "Pharmaceuticals salts", JOURNAL OF PHARMACEUTICAL SCIENCES, 1977, vol.66, no.1, p.1-16, . RICHARD J.BASTIN et al.: "Salt selection and optimization procedures for pharmaceutical new chemical entities", ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, vol.4, no.5, p.427-435, . * |
| TAKASHI SOHDA et al.: "Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)-benzyl]thiazolidine-2,4-dione (ADD-3878) and its derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, 1982, vol.30, no.10, p.3580-3600. * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2012129930A (ru) | 2014-01-27 |
| CN102753539B (zh) | 2015-09-09 |
| NO2513070T3 (OSRAM) | 2018-04-07 |
| US20120309975A1 (en) | 2012-12-06 |
| HUE038042T2 (hu) | 2018-09-28 |
| KR20120107493A (ko) | 2012-10-02 |
| AU2010340055B2 (en) | 2014-07-24 |
| WO2011084453A1 (en) | 2011-07-14 |
| US8912335B2 (en) | 2014-12-16 |
| US20150051406A1 (en) | 2015-02-19 |
| HK1174330A1 (en) | 2013-06-07 |
| KR20180089569A (ko) | 2018-08-08 |
| CA2783468C (en) | 2018-10-09 |
| EP2513070A1 (en) | 2012-10-24 |
| CA2783468A1 (en) | 2011-07-14 |
| DK2513070T3 (en) | 2018-01-22 |
| KR102029560B1 (ko) | 2019-10-07 |
| EP2513070B1 (en) | 2017-11-08 |
| KR102029611B1 (ko) | 2019-10-07 |
| JP5634526B2 (ja) | 2014-12-03 |
| ES2658168T3 (es) | 2018-03-08 |
| PL2513070T3 (pl) | 2018-05-30 |
| MX2012006725A (es) | 2012-06-28 |
| AU2010340055A1 (en) | 2012-06-28 |
| JP2013514367A (ja) | 2013-04-25 |
| CN102753539A (zh) | 2012-10-24 |
| NZ600390A (en) | 2013-08-30 |
| US9126959B2 (en) | 2015-09-08 |
| KR20170044214A (ko) | 2017-04-24 |
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