IL127408A - History 2, 4 - Thiazolidinedione, process for their preparation and pharmaceutical preparations containing them - Google Patents
History 2, 4 - Thiazolidinedione, process for their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL127408A IL127408A IL12740897A IL12740897A IL127408A IL 127408 A IL127408 A IL 127408A IL 12740897 A IL12740897 A IL 12740897A IL 12740897 A IL12740897 A IL 12740897A IL 127408 A IL127408 A IL 127408A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- group
- thiazolidinedione
- compound
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical class O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 6
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 4
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
- 150000003457 sulfones Chemical class 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 78
- -1 4-cyanophenoxy Chemical group 0.000 claims description 39
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 230000009471 action Effects 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 14
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical compound NC1=NC(=O)CS1 HYMJHROUVPWYNQ-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000001079 digestive effect Effects 0.000 claims description 2
- 125000004982 dihaloalkyl group Chemical group 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 abstract description 7
- 230000003178 anti-diabetic effect Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000012429 reaction media Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 150000001467 thiazolidinediones Chemical group 0.000 description 11
- 102000004877 Insulin Human genes 0.000 description 10
- 108090001061 Insulin Proteins 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229940125396 insulin Drugs 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 206010022489 Insulin Resistance Diseases 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- VKNUENLPKPOOPS-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-fluorobenzene Chemical compound FC1=CC=C(OCCCBr)C=C1 VKNUENLPKPOOPS-UHFFFAOYSA-N 0.000 description 7
- FULPOHDTUXYKOC-UHFFFAOYSA-N 2-[3-(4-fluorophenoxy)propyl]propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCCOC1=CC=C(F)C=C1 FULPOHDTUXYKOC-UHFFFAOYSA-N 0.000 description 7
- DIJXNMBUKXVOEF-UHFFFAOYSA-N 2-amino-5-(2-phenoxyethyl)-1,3-thiazol-4-one Chemical compound S1C(=N)NC(=O)C1CCOC1=CC=CC=C1 DIJXNMBUKXVOEF-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- ATJFHEFBESTYKU-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetaldehyde Chemical compound FC1=CC=C(OCC=O)C=C1 ATJFHEFBESTYKU-UHFFFAOYSA-N 0.000 description 5
- SBTMMHAWLLQXTB-UHFFFAOYSA-N 2-chloro-2-[3-(4-fluorophenoxy)propyl]propanedioic acid Chemical compound OC(=O)C(Cl)(C(O)=O)CCCOC1=CC=C(F)C=C1 SBTMMHAWLLQXTB-UHFFFAOYSA-N 0.000 description 5
- DQKGDEKWZQOPIE-UHFFFAOYSA-N 2-chloro-5-(4-fluorophenoxy)pentanoic acid Chemical compound OC(=O)C(Cl)CCCOC1=CC=C(F)C=C1 DQKGDEKWZQOPIE-UHFFFAOYSA-N 0.000 description 5
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- CGWDABYOHPEOAD-UHFFFAOYSA-N 2-[(4-fluorophenoxy)methyl]oxirane Chemical compound C1=CC(F)=CC=C1OCC1OC1 CGWDABYOHPEOAD-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
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- 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 3
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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- YZTPAOFYMLONRV-UHFFFAOYSA-N 5-(2-phenoxyethyl)-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CCOC1=CC=CC=C1 YZTPAOFYMLONRV-UHFFFAOYSA-N 0.000 description 2
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- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 239000001632 sodium acetate Substances 0.000 description 2
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- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- 229960001052 streptozocin Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
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Classifications
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9607070A FR2749583B1 (fr) | 1996-06-07 | 1996-06-07 | Nouveaux derives de thiazolidine -2,4- dione substitues, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| PCT/EP1997/002851 WO1997047612A1 (fr) | 1996-06-07 | 1997-06-02 | Nouveaux derives de thiazolidine-2,4-dione substitues, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL127408A0 IL127408A0 (en) | 1999-10-28 |
| IL127408A true IL127408A (en) | 2002-08-14 |
Family
ID=9492815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12740897A IL127408A (en) | 1996-06-07 | 1997-06-02 | History 2, 4 - Thiazolidinedione, process for their preparation and pharmaceutical preparations containing them |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6437143B2 (cs) |
| EP (1) | EP0918759B1 (cs) |
| JP (2) | JP3067809B2 (cs) |
| KR (1) | KR20000016412A (cs) |
| CN (2) | CN1075811C (cs) |
| AR (1) | AR008387A1 (cs) |
| AT (1) | ATE222897T1 (cs) |
| AU (1) | AU726549B2 (cs) |
| BR (1) | BR9709654A (cs) |
| CA (1) | CA2257275A1 (cs) |
| CZ (1) | CZ397598A3 (cs) |
| DE (1) | DE69715009T2 (cs) |
| DK (1) | DK0918759T3 (cs) |
| EE (1) | EE04015B1 (cs) |
| ES (1) | ES2180995T3 (cs) |
| FR (1) | FR2749583B1 (cs) |
| HU (1) | HUP0001744A3 (cs) |
| ID (1) | ID17810A (cs) |
| IL (1) | IL127408A (cs) |
| NO (1) | NO312100B1 (cs) |
| NZ (1) | NZ333645A (cs) |
| PL (1) | PL330363A1 (cs) |
| PT (1) | PT918759E (cs) |
| RU (1) | RU2169144C2 (cs) |
| SK (1) | SK164598A3 (cs) |
| TR (1) | TR199802518T2 (cs) |
| TW (1) | TW400330B (cs) |
| UA (1) | UA57024C2 (cs) |
| WO (1) | WO1997047612A1 (cs) |
| ZA (1) | ZA974984B (cs) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083966A (en) * | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| CN1585639A (zh) * | 1998-09-21 | 2005-02-23 | 佛罗里达大学研究基金会 | 抗疟疾制剂 |
| CA2368146A1 (en) * | 1999-03-18 | 2000-09-21 | Ono Pharmaceutical Co., Ltd. | A process for the preparation of thiazolidine derivatives |
| DE60005973T2 (de) | 1999-08-27 | 2004-05-13 | Eli Lilly And Co., Indianapolis | Biaryl-oxa(thia)zolderivate und ihre verwendung als ppars modulatoren |
| FR2812547B1 (fr) * | 2000-08-04 | 2002-10-31 | Lipha | Composition pharmaceutique comprenant une association metformine et derive de thiazolidinedione et son utilisation pour la preparation de medicaments destines a traiter le diabete |
| FR2822069B1 (fr) * | 2001-03-19 | 2003-06-20 | Lipha | Composition pharmaceutique comprenant un compose stimulant la secretion d'insuline et un derive de thiazolidinedione et son utilisation pour la preparation de medicamments destines a traiter le diabete |
| FR2826278B1 (fr) * | 2001-06-20 | 2005-03-25 | Lipha | Utilisation d'agents antidiabetiques pour fabriquer un medicament ayant un effet cicatrisant |
| EP1448509B1 (en) * | 2001-09-26 | 2012-12-19 | Emisphere Technologies, Inc. | Method of preparing phenoxy alkanoic acids and salts thereof via a dicarboxylate intermediate |
| FR2838968A1 (fr) * | 2002-04-30 | 2003-10-31 | Lipha | Association d'insuline et d'un derive de thiazolidinedione et son utilisation pour traiter le diabete |
| SE0201937D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
| FR2845003A1 (fr) * | 2002-09-30 | 2004-04-02 | Merck Sante Sas | Utilisation de derives de thiazolidinedione comme inhibiteurs de l'aldose reductase |
| WO2005034949A1 (en) * | 2003-09-09 | 2005-04-21 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| US20060263453A1 (en) * | 2004-11-01 | 2006-11-23 | Thomas Smith | Methods and compositions for modulating glutamate dehydrogenase |
| DK1866296T3 (en) | 2005-04-04 | 2017-02-13 | Univ Florida | DESFERRITHIOCINPOLYETHER-ANALOGS |
| AU2008229472B2 (en) | 2007-03-15 | 2013-03-14 | University Of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
| EP3053440B1 (en) * | 2007-04-11 | 2020-08-12 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| US11241420B2 (en) | 2007-04-11 | 2022-02-08 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| US20160331729A9 (en) * | 2007-04-11 | 2016-11-17 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| DE102007028925A1 (de) * | 2007-06-22 | 2008-12-24 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden |
| JP6539046B2 (ja) | 2011-12-16 | 2019-07-03 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | ４’−デスフェリチオシン類似体の使用 |
| WO2015042495A2 (en) * | 2013-09-22 | 2015-03-26 | Jiva Pharma, Inc. | Metformin salts to treat type2 diabetes |
| CA2930966A1 (en) | 2013-11-22 | 2015-05-28 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogs and uses thereof |
| JP2018515475A (ja) | 2015-04-27 | 2018-06-14 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | 代謝的にプログラムされた金属キレーターおよびその使用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5522636A (en) * | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| SU1611216A3 (ru) * | 1986-12-29 | 1990-11-30 | Пфайзер Инк (Фирма) | Способ получени производных тиазолидиндиона или их фармацевтически приемлемых солей с щелочными металлами |
| TW268952B (cs) * | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| US5614544A (en) * | 1993-09-14 | 1997-03-25 | Takeda Chemical Industries, Ltd. | Oxazolidinedione derivatives and their use |
| EP0783496B9 (en) * | 1994-08-10 | 2003-09-03 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
-
1996
- 1996-06-07 FR FR9607070A patent/FR2749583B1/fr not_active Expired - Fee Related
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1997
- 1997-02-06 UA UA99010018A patent/UA57024C2/uk unknown
- 1997-06-02 SK SK1645-98A patent/SK164598A3/sk unknown
- 1997-06-02 ES ES97925034T patent/ES2180995T3/es not_active Expired - Lifetime
- 1997-06-02 EP EP97925034A patent/EP0918759B1/fr not_active Expired - Lifetime
- 1997-06-02 TR TR1998/02518T patent/TR199802518T2/xx unknown
- 1997-06-02 DK DK97925034T patent/DK0918759T3/da active
- 1997-06-02 BR BR9709654A patent/BR9709654A/pt not_active IP Right Cessation
- 1997-06-02 US US09/202,076 patent/US6437143B2/en not_active Expired - Fee Related
- 1997-06-02 HU HU0001744A patent/HUP0001744A3/hu unknown
- 1997-06-02 PT PT97925034T patent/PT918759E/pt unknown
- 1997-06-02 NZ NZ333645A patent/NZ333645A/xx unknown
- 1997-06-02 RU RU99100100/04A patent/RU2169144C2/ru not_active IP Right Cessation
- 1997-06-02 IL IL12740897A patent/IL127408A/en not_active IP Right Cessation
- 1997-06-02 AT AT97925034T patent/ATE222897T1/de not_active IP Right Cessation
- 1997-06-02 JP JP10501140A patent/JP3067809B2/ja not_active Expired - Fee Related
- 1997-06-02 AU AU30317/97A patent/AU726549B2/en not_active Ceased
- 1997-06-02 EE EE9800426A patent/EE04015B1/xx not_active IP Right Cessation
- 1997-06-02 PL PL97330363A patent/PL330363A1/xx unknown
- 1997-06-02 DE DE69715009T patent/DE69715009T2/de not_active Expired - Fee Related
- 1997-06-02 CN CN97195320A patent/CN1075811C/zh not_active Expired - Fee Related
- 1997-06-02 CA CA002257275A patent/CA2257275A1/en not_active Abandoned
- 1997-06-02 WO PCT/EP1997/002851 patent/WO1997047612A1/fr active Search and Examination
- 1997-06-02 CZ CZ983975A patent/CZ397598A3/cs unknown
- 1997-06-02 KR KR1019980709995A patent/KR20000016412A/ko not_active Ceased
- 1997-06-05 ZA ZA9704984A patent/ZA974984B/xx unknown
- 1997-06-06 TW TW086107848A patent/TW400330B/zh active
- 1997-06-06 AR ARP970102468A patent/AR008387A1/es not_active Application Discontinuation
- 1997-06-09 ID IDP971967A patent/ID17810A/id unknown
-
1998
- 1998-12-04 NO NO19985671A patent/NO312100B1/no not_active IP Right Cessation
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1999
- 1999-12-15 JP JP11355996A patent/JP2000226379A/ja active Pending
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2001
- 2001-01-22 CN CN01103050A patent/CN1341588A/zh active Pending
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2002
- 2002-06-27 US US10/180,071 patent/US20030100587A1/en not_active Abandoned
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