CA2663901A1 - Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia - Google Patents
Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia Download PDFInfo
- Publication number
- CA2663901A1 CA2663901A1 CA002663901A CA2663901A CA2663901A1 CA 2663901 A1 CA2663901 A1 CA 2663901A1 CA 002663901 A CA002663901 A CA 002663901A CA 2663901 A CA2663901 A CA 2663901A CA 2663901 A1 CA2663901 A1 CA 2663901A1
- Authority
- CA
- Canada
- Prior art keywords
- phenoxy
- compound
- chloropyridin
- pharmaceutically acceptable
- sulfonamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 67
- 206010022489 Insulin Resistance Diseases 0.000 title claims abstract description 49
- 201000001421 hyperglycemia Diseases 0.000 title claims abstract description 29
- 208000030159 metabolic disease Diseases 0.000 title claims abstract description 27
- 238000011282 treatment Methods 0.000 title claims description 33
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000012453 solvate Substances 0.000 claims abstract description 45
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- -1 2-chloro-4-trifluoromethylphenyl Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
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- NQYPWOIINHGONL-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-2,4-dichlorobenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC(C(=C1)Cl)=NC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl NQYPWOIINHGONL-UHFFFAOYSA-N 0.000 claims description 11
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
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- PVCPTUCCNBNGJA-UHFFFAOYSA-N 2,4-dichloro-n-[5-chloro-6-(4-piperazin-1-ylphenoxy)pyridin-3-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=C(N2CCNCC2)C=C1 PVCPTUCCNBNGJA-UHFFFAOYSA-N 0.000 claims description 9
- WSSGFXLEEROCQE-UHFFFAOYSA-N 4-[[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]amino]-4-oxobutanoic acid Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC1=NC=C(NC(=O)CCC(O)=O)C=C1Cl WSSGFXLEEROCQE-UHFFFAOYSA-N 0.000 claims description 9
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 208000029078 coronary artery disease Diseases 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- KDSRSZGZHWZQDK-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-2,4-difluorobenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC(C(=C1)Cl)=NC=C1NS(=O)(=O)C1=CC=C(F)C=C1F KDSRSZGZHWZQDK-UHFFFAOYSA-N 0.000 claims description 6
- XVLAYBFGGPSKEI-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=C(Cl)C(OC=3C=CC(=CC=3)N3CCN(CC3)C(C)=O)=NC=2)=C1 XVLAYBFGGPSKEI-UHFFFAOYSA-N 0.000 claims description 6
- BLCBUFRTWIYESO-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC(C(=C1)Cl)=NC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 BLCBUFRTWIYESO-UHFFFAOYSA-N 0.000 claims description 6
- ZZSWASGMMWCOKM-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC(C(=C1)Cl)=NC=C1NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 ZZSWASGMMWCOKM-UHFFFAOYSA-N 0.000 claims description 6
- YGFGZRPSUYAPEN-UHFFFAOYSA-N n-[6-[4-(4-acetylpiperazin-1-yl)phenoxy]-5-chloropyridin-3-yl]-4-methylbenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC(C(=C1)Cl)=NC=C1NS(=O)(=O)C1=CC=C(C)C=C1 YGFGZRPSUYAPEN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 5
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
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- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- VANNTJQBHBPGTP-UHFFFAOYSA-N n-[5-chloro-6-[3-(4-methylpiperazin-1-yl)phenoxy]pyridin-3-yl]-2,4-difluorobenzenesulfonamide Chemical compound C1CN(C)CCN1C1=CC=CC(OC=2C(=CC(NS(=O)(=O)C=3C(=CC(F)=CC=3)F)=CN=2)Cl)=C1 VANNTJQBHBPGTP-UHFFFAOYSA-N 0.000 claims description 5
- ULQKHMVAHYUOQT-UHFFFAOYSA-N n-[5-chloro-6-[3-(4-methylpiperazin-1-yl)phenoxy]pyridin-3-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=CC(N2CCN(C)CC2)=C1 ULQKHMVAHYUOQT-UHFFFAOYSA-N 0.000 claims description 5
- GFFZPVSHWVDUOK-UHFFFAOYSA-N n-[6-[2-(1,3-benzothiazol-2-yl)phenoxy]-5-chloropyridin-3-yl]-2,4-dichlorobenzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 GFFZPVSHWVDUOK-UHFFFAOYSA-N 0.000 claims description 5
- DQTGFGHIFCBLJW-UHFFFAOYSA-N n-[6-[2-(1,3-benzothiazol-2-yl)phenoxy]-5-chloropyridin-3-yl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 DQTGFGHIFCBLJW-UHFFFAOYSA-N 0.000 claims description 5
- CZEILIVPLFRLOO-UHFFFAOYSA-N n-[6-[2-(1,3-benzothiazol-2-yl)phenoxy]-5-chloropyridin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 CZEILIVPLFRLOO-UHFFFAOYSA-N 0.000 claims description 5
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- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000000276 sedentary effect Effects 0.000 description 1
- 238000003375 selectivity assay Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- DTZOCKDNFAGLSB-UHFFFAOYSA-N trifluoromethoxycyanamide Chemical group FC(ONC#N)(F)F DTZOCKDNFAGLSB-UHFFFAOYSA-N 0.000 description 1
- 238000011870 unpaired t-test Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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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
-
- 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
- A61P3/06—Antihyperlipidemics
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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
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84619406P | 2006-09-21 | 2006-09-21 | |
| US60/846,194 | 2006-09-21 | ||
| US87567206P | 2006-12-18 | 2006-12-18 | |
| US60/875,672 | 2006-12-18 | ||
| PCT/IB2007/053811 WO2008035305A2 (en) | 2006-09-21 | 2007-09-20 | Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2663901A1 true CA2663901A1 (en) | 2008-03-27 |
Family
ID=39048032
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002663901A Abandoned CA2663901A1 (en) | 2006-09-21 | 2007-09-20 | Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia |
| CA002663943A Abandoned CA2663943A1 (en) | 2006-09-21 | 2007-09-20 | 3-amino-pyridine derivatives for the treatment of metabolic disorders |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002663943A Abandoned CA2663943A1 (en) | 2006-09-21 | 2007-09-20 | 3-amino-pyridine derivatives for the treatment of metabolic disorders |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US8030324B2 (enExample) |
| EP (2) | EP2094663B1 (enExample) |
| JP (2) | JP5331953B2 (enExample) |
| KR (2) | KR20090075827A (enExample) |
| AR (2) | AR062941A1 (enExample) |
| AT (1) | ATE496890T1 (enExample) |
| AU (2) | AU2007298539B2 (enExample) |
| BR (2) | BRPI0718510A2 (enExample) |
| CA (2) | CA2663901A1 (enExample) |
| DE (1) | DE602007012299D1 (enExample) |
| DK (1) | DK2094663T3 (enExample) |
| IL (2) | IL197695A0 (enExample) |
| MX (2) | MX2009002905A (enExample) |
| NZ (2) | NZ576197A (enExample) |
| PL (1) | PL2094663T3 (enExample) |
| PT (1) | PT2094663E (enExample) |
| RU (2) | RU2448093C2 (enExample) |
| TW (2) | TW200820970A (enExample) |
| WO (2) | WO2008035305A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013117963A1 (en) | 2012-02-09 | 2013-08-15 | Piramal Enterprises Limited | Stable oral tablet dosage form of an antidiabetic compound |
| PE20160664A1 (es) | 2013-06-27 | 2016-07-09 | Pfizer | Compuestos heteroaromaticos y su uso como ligandos d1 de dopamina |
| WO2014207508A1 (en) * | 2013-06-27 | 2014-12-31 | Piramal Enterprises Limited | Pyridyl compound suitable for the treatment of metabolic disorders |
| EA028614B1 (ru) * | 2014-05-22 | 2017-12-29 | Общество С Ограниченной Ответственностью "Русские Фармацевтические Технологии" | Селективные ингибиторы, нарушающие взаимодействие рецептора фактора роста фибробластов и frs2, для профилактики и лечения рака |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
| MX2023005371A (es) | 2020-11-09 | 2023-05-22 | Eisai R&D Man Co Ltd | Moduladores de receptor gamma activado por proliferador de peroxisoma (ppar gamma) y metodos de uso. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084085A (en) * | 1986-08-20 | 1992-01-28 | Fmc Corporation | Herbicidal aryloxyphenyltriazolinones and related compounds |
| UA58494C2 (uk) * | 1995-06-07 | 2003-08-15 | Зенека Лімітед | Похідні n-гетероарилпіридинсульфонаміду, фармацевтична композиція, спосіб одержання та спосіб протидії впливам ендотеліну |
| US6583157B2 (en) * | 1998-01-29 | 2003-06-24 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| NZ515087A (en) * | 1999-04-28 | 2003-11-28 | Aventis Pharma Gmbh | Tri-aryl acid derivatives as PPAR receptor ligands |
| WO2001000579A1 (en) * | 1999-06-30 | 2001-01-04 | Tularik Inc. | COMPOUNDS FOR THE MODULATION OF PPARη ACTIVITY |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| HK1052351B (en) * | 2000-06-28 | 2006-11-03 | Japan Tobacco Inc. | Benzothiazolyl ppar-gamma modulators |
| CA2526204A1 (en) * | 2003-06-12 | 2004-12-23 | Novo Nordisk A/S | Pyridinyl carbamates as hormone-sensitive lipase inhibitors |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| US8188277B2 (en) * | 2004-08-06 | 2012-05-29 | Otsuka Pharmaceutical Co., Ltd. | Aromatic compounds for suppressing the generation of collagen |
| RU2383533C2 (ru) * | 2004-10-04 | 2010-03-10 | Ф.Хоффманн-Ля Рош Аг | Алкилированные производные пиридина в качестве ингибиторов 11-бета при диабете |
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2007
- 2007-09-20 US US12/441,802 patent/US8030324B2/en not_active Expired - Fee Related
- 2007-09-20 CA CA002663901A patent/CA2663901A1/en not_active Abandoned
- 2007-09-20 NZ NZ576197A patent/NZ576197A/en not_active IP Right Cessation
- 2007-09-20 US US12/441,891 patent/US8269010B2/en not_active Expired - Fee Related
- 2007-09-20 KR KR1020097008115A patent/KR20090075827A/ko not_active Ceased
- 2007-09-20 TW TW096135229A patent/TW200820970A/zh unknown
- 2007-09-20 KR KR1020097008116A patent/KR20090074775A/ko not_active Ceased
- 2007-09-20 DK DK07826467.8T patent/DK2094663T3/da active
- 2007-09-20 AU AU2007298539A patent/AU2007298539B2/en not_active Ceased
- 2007-09-20 WO PCT/IB2007/053811 patent/WO2008035305A2/en not_active Ceased
- 2007-09-20 PL PL07826467T patent/PL2094663T3/pl unknown
- 2007-09-20 DE DE602007012299T patent/DE602007012299D1/de active Active
- 2007-09-20 PT PT07826467T patent/PT2094663E/pt unknown
- 2007-09-20 RU RU2009114544/04A patent/RU2448093C2/ru not_active IP Right Cessation
- 2007-09-20 EP EP07826467A patent/EP2094663B1/en not_active Not-in-force
- 2007-09-20 NZ NZ576196A patent/NZ576196A/en not_active IP Right Cessation
- 2007-09-20 AT AT07826467T patent/ATE496890T1/de active
- 2007-09-20 EP EP07826468A patent/EP2094687A1/en not_active Withdrawn
- 2007-09-20 MX MX2009002905A patent/MX2009002905A/es active IP Right Grant
- 2007-09-20 RU RU2009114545/04A patent/RU2460729C2/ru not_active IP Right Cessation
- 2007-09-20 BR BRPI0718510-3A patent/BRPI0718510A2/pt not_active IP Right Cessation
- 2007-09-20 WO PCT/IB2007/053812 patent/WO2008035306A1/en not_active Ceased
- 2007-09-20 TW TW096135227A patent/TW200817364A/zh unknown
- 2007-09-20 JP JP2009528851A patent/JP5331953B2/ja not_active Expired - Fee Related
- 2007-09-20 AU AU2007298540A patent/AU2007298540B2/en not_active Ceased
- 2007-09-20 MX MX2009002906A patent/MX2009002906A/es active IP Right Grant
- 2007-09-20 JP JP2009528850A patent/JP2010504321A/ja not_active Ceased
- 2007-09-20 CA CA002663943A patent/CA2663943A1/en not_active Abandoned
- 2007-09-20 BR BRPI0717106-4A patent/BRPI0717106A2/pt not_active IP Right Cessation
- 2007-09-21 AR ARP070104184A patent/AR062941A1/es not_active Application Discontinuation
- 2007-09-21 AR ARP070104183A patent/AR062940A1/es unknown
-
2009
- 2009-03-19 IL IL197695A patent/IL197695A0/en unknown
- 2009-03-19 IL IL197694A patent/IL197694A0/en unknown
-
2011
- 2011-08-31 US US13/222,662 patent/US8349862B2/en not_active Expired - Fee Related
-
2012
- 2012-08-13 US US13/584,134 patent/US20120309786A1/en not_active Abandoned
- 2012-08-13 US US13/584,043 patent/US20130040988A1/en not_active Abandoned
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140922 |