NZ750252B2 - Sulfonamides as gpr40- and gpr120-agonists - Google Patents
Sulfonamides as gpr40- and gpr120-agonistsInfo
- Publication number
- NZ750252B2 NZ750252B2 NZ750252A NZ75025217A NZ750252B2 NZ 750252 B2 NZ750252 B2 NZ 750252B2 NZ 750252 A NZ750252 A NZ 750252A NZ 75025217 A NZ75025217 A NZ 75025217A NZ 750252 B2 NZ750252 B2 NZ 750252B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- phenyl
- sulfamoyl
- heptanoic acid
- dimethylphenyl
- compound according
- Prior art date
Links
- 239000000556 agonist Substances 0.000 title abstract 2
- 229940124530 sulfonamide Drugs 0.000 title 1
- 150000003456 sulfonamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 5
- 208000035475 disorder Diseases 0.000 claims abstract 3
- 201000010099 disease Diseases 0.000 claims abstract 2
- -1 1,3,4-triazolyl Chemical group 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 8
- YLPQGOVWSLQKGS-UHFFFAOYSA-N 6-[3-[(2,4,6-trimethylphenyl)sulfamoyl]phenyl]hexanoic acid Chemical compound CC1=C(C(=CC(=C1)C)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCC(=O)O YLPQGOVWSLQKGS-UHFFFAOYSA-N 0.000 claims 4
- YCFPSAZMPGKIHM-UHFFFAOYSA-N 7-[3-[(2,4,6-trimethylphenyl)methylsulfamoyl]phenyl]heptanoic acid Chemical compound CC1=C(CNS(=O)(=O)C=2C=C(C=CC=2)CCCCCCC(=O)O)C(=CC(=C1)C)C YCFPSAZMPGKIHM-UHFFFAOYSA-N 0.000 claims 4
- UTNWVDGMFJRPEY-UHFFFAOYSA-N 7-[3-[(2,6-dimethyl-4-propan-2-ylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound C(C)(C)C1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C UTNWVDGMFJRPEY-UHFFFAOYSA-N 0.000 claims 4
- MGLYEDQXPBGWNF-UHFFFAOYSA-N 7-[3-[(3-phenyl-1,2-thiazol-4-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound C1(=CC=CC=C1)C1=NSC=C1NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O MGLYEDQXPBGWNF-UHFFFAOYSA-N 0.000 claims 4
- DAWXONFLFOSEDH-UHFFFAOYSA-N 7-[3-[(4-bromo-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound BrC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C DAWXONFLFOSEDH-UHFFFAOYSA-N 0.000 claims 4
- SGDYEWCWFVKVBQ-UHFFFAOYSA-N 7-[3-[(4-chloro-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound ClC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C SGDYEWCWFVKVBQ-UHFFFAOYSA-N 0.000 claims 4
- QWJJUWOIRPFSON-UHFFFAOYSA-N 7-[3-[(4-fluoro-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound FC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C QWJJUWOIRPFSON-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- OTMSVBUQSMZMSW-UHFFFAOYSA-N 7-[3-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-ylsulfamoyl)phenyl]heptanoic acid Chemical compound N1C(=NC2C1CCCC2)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O OTMSVBUQSMZMSW-UHFFFAOYSA-N 0.000 claims 2
- UVEWYBUDYCJEOW-UHFFFAOYSA-N 7-[3-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC=1SC(=C(N=1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O UVEWYBUDYCJEOW-UHFFFAOYSA-N 0.000 claims 2
- PUOZZDFMOZLJJI-UHFFFAOYSA-N 7-[3-[(2,6-dimethyl-4-phenylmethoxyphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound C(C1=CC=CC=C1)OC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C PUOZZDFMOZLJJI-UHFFFAOYSA-N 0.000 claims 2
- BKQWGOCZWLEXQM-UHFFFAOYSA-N 7-[3-[(2-ethyltriazol-4-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound C(C)N1N=CC(=N1)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O BKQWGOCZWLEXQM-UHFFFAOYSA-N 0.000 claims 2
- QIJFBFSFYOLFIU-UHFFFAOYSA-N 7-[3-[(3,5-dimethyl-1,2,4-triazol-4-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC1=NN=C(N1NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C QIJFBFSFYOLFIU-UHFFFAOYSA-N 0.000 claims 2
- MHIDYBMLIJCTEI-UHFFFAOYSA-N 7-[3-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC1=NOC(=C1NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C MHIDYBMLIJCTEI-UHFFFAOYSA-N 0.000 claims 2
- YIZVIBFLGZJSPF-UHFFFAOYSA-N 7-[3-[(4,5-dimethyl-1,3-oxazol-2-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC=1N=C(OC=1C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O YIZVIBFLGZJSPF-UHFFFAOYSA-N 0.000 claims 2
- CPCKXQPHEVVBDG-UHFFFAOYSA-N 7-[3-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC=1N=C(SC=1C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O CPCKXQPHEVVBDG-UHFFFAOYSA-N 0.000 claims 2
- HRYVPHGWBZDNCA-UHFFFAOYSA-N 7-[3-[(4-fluoro-2,6-dimethylbenzoyl)sulfamoyl]phenyl]heptanoic acid Chemical compound FC1=CC(=C(C(=O)NS(=O)(=O)C=2C=C(C=CC=2)CCCCCCC(=O)O)C(=C1)C)C HRYVPHGWBZDNCA-UHFFFAOYSA-N 0.000 claims 2
- FFENSWJSUQODRJ-UHFFFAOYSA-N 7-[3-[(4-hydroxy-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound OC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C FFENSWJSUQODRJ-UHFFFAOYSA-N 0.000 claims 2
- CLTJGXZKSAEJLM-UHFFFAOYSA-N 7-[3-[(4-methoxy-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound COC1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C CLTJGXZKSAEJLM-UHFFFAOYSA-N 0.000 claims 2
- OJCRMTSEQVDHJL-UHFFFAOYSA-N 7-[3-[(5-hydroxynaphthalen-1-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound OC1=C2C=CC=C(C2=CC=C1)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O OJCRMTSEQVDHJL-UHFFFAOYSA-N 0.000 claims 2
- MBPHUKRGMBYDFZ-UHFFFAOYSA-N 7-[3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC1=NN=C(S1)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O MBPHUKRGMBYDFZ-UHFFFAOYSA-N 0.000 claims 2
- SFNQRRDAHSGKDM-UHFFFAOYSA-N 7-[3-[(5-methyl-1H-1,2,4-triazol-3-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound CC=1NC(=NN=1)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O SFNQRRDAHSGKDM-UHFFFAOYSA-N 0.000 claims 2
- WOVVRQUYHABIKO-UHFFFAOYSA-N 7-[3-[(5-phenyl-1,2,4-thiadiazol-3-yl)sulfamoyl]phenyl]heptanoic acid Chemical compound C1(=CC=CC=C1)C1=NC(=NS1)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O WOVVRQUYHABIKO-UHFFFAOYSA-N 0.000 claims 2
- WRVPLGACRFXYKU-UHFFFAOYSA-N 7-[3-[[4-(dimethylamino)-2,6-dimethylphenyl]sulfamoyl]phenyl]heptanoic acid Chemical compound CN(C1=CC(=C(C(=C1)C)NS(=O)(=O)C=1C=C(C=CC=1)CCCCCCC(=O)O)C)C WRVPLGACRFXYKU-UHFFFAOYSA-N 0.000 claims 2
- CTXZISRSSNFNFX-UHFFFAOYSA-N 7-[4-[(4-fluoro-2,6-dimethylphenyl)sulfamoyl]phenyl]heptanoic acid Chemical compound FC1=CC(=C(C(=C1)C)NS(=O)(=O)C1=CC=C(C=C1)CCCCCCC(=O)O)C CTXZISRSSNFNFX-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 abstract 4
- 235000020824 obesity Nutrition 0.000 abstract 4
- 102100040134 Free fatty acid receptor 4 Human genes 0.000 abstract 3
- 101710142055 Free fatty acid receptor 4 Proteins 0.000 abstract 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 2
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 208000032928 Dyslipidaemia Diseases 0.000 abstract 1
- 206010014486 Elevated triglycerides Diseases 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 206010022489 Insulin Resistance Diseases 0.000 abstract 1
- 208000017170 Lipid metabolism disease Diseases 0.000 abstract 1
- 208000001145 Metabolic Syndrome Diseases 0.000 abstract 1
- 208000001132 Osteoporosis Diseases 0.000 abstract 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 230000001771 impaired effect Effects 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- A—HUMAN NECESSITIES
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- 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
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
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- 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
- A61K31/4192—1,2,3-Triazoles
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- 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
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A61K31/433—Thidiazoles
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/38—Nitrogen atoms
- C07D231/42—Benzene-sulfonamido pyrazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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Abstract
The invention relates to compounds acting as agonists of G-protein coupled receptor 120 (GPR120) and/or 40 (GPR40), and having formula (I). Said compounds are useful in the treatment of diseases or disorders modulated by GPR120 and/or GPR40 such as diabetes (particularly type 2 diabetes), impaired oral glucose tolerance, insulin resistance, obesity, obesity related disorders, metabolic syndrome, dyslipidemia, elevated LDL, elevated triglycerides, obesity induced inflammation, osteoporosis and obesity related cardiovascular disorders.
Claims (10)
1. A compound of formula (I): A (X)n NH S(O)2 R3 R2 and pharmaceutically acceptable salts thereof, wherein: A is a mono or di-carbocyclic residue, optionally partially or totally unsaturated, consisting of carbon atoms and optionally one or more heteroatoms selected from N, S or O; R1, R2, R3 are independently selected from the group consisting of –H, -halogen, - CF3, -CN, -CH2CN, -OMe, -OCF3, -OH, phenyl, -OPh, -OCH2Ph, -OCH2OMe, - OCH2CN -NO2, -NR’R”, linear or ed C1-C6 alkyl, -O(CH2)p-S(O)2Me and a fivemembered ring heterocycle; wherein R’ and R” are ndently –H or C1-C4 alkyl; n phenyl and the five-membered ring heterocycle are independently unsubstituted or substituted with a group ed from the group consisting of linear or branched C1-C4 alkyl, halogen, -OMe and –OH; p is 1 to 4; X is –CH2 or –C(O); n is 0, 1or 2; wherein when n is 2, X can be the same or different; R4 is –Y–C(O)OH, wherein Y is a straight chain C4-C18 hydrocarbon, saturated or unsaturated, preferably having from 6 to 10 carbon atoms; R4 is in position meta or para on the aromatic ring; wherein when A is phenyl, n is 0, Y is a C4 hydrocarbon, at least one of said R1, R2, R3 is not hydrogen; wherein when A is , n is 0, Y is a C4 hydrocarbon, R1 and R2 are hydrogen, R3 is not Cl in position para on the aromatic ring.
2. A compound according to claim 1, wherein A is phenyl, naphthyl, biphenyl or a saturated or unsaturated five-membered ring heterocycle having five ring atoms wherein 1, 2, 3 or 4 ring atoms are independently selected from N, O and S.
3. A compound according to claim 1 or 2, wherein the five-membered ring heterocycle is selected from the group consisting of l, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyrazolyl, azolyl, isoxazolyl, triazolyl, tetrazolyl, 1,2,3- thiadiazolyl, oxadiazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, oxadiazolyl, 1,3,4-triazolyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, and benzimidazole, ally partially saturated.
4. A compound according to anyone of claims 1 to 3, wherein R1, R2, R3 are independently selected from the group consisting of –H, -halogen, -CF3, -OMe, -OH, phenyl, -OPh, -OCH2Ph, -OCH2OMe, -OCH2CN -NO2, -NH2, -NMe2, linear or branched C1-C6 alkyl and -O(CH2)p-S(O)2Me.
5. A compound according to anyone of claims 1 to 4, wherein n is 0 or 1.
6. A compound according to anyone of claims 1 to 5, wherein R4 is in on meta on the aromatic ring.
7. A compound according to anyone of claims 1 to 6 selected from: 7-(3-(N-(4-fluoro-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (1); 7-(3-(N-(2,4,6-trimethylbenzyl)sulfamoyl)phenyl)heptanoic acid (2); 7-(3-(N-(4-isopropyl-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (3); 7-(3-(N-(4-chloro-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (4); 7-(3-(N-(4-(dimethylamino)-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (5); 7-(3-(N-(2,6-dimethyl(trifluoromethyl)phenyl)sulfamoyl)phenyl)heptanoic acid (6); 7-(3-(N-(4-bromo-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (7); 7-(3-(N-(4-methoxy-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (8); 7-(3-(N-(6-fluoromethyl-[1,1'-biphenyl]yl)sulfamoyl)phenyl)heptanoic acid (9); N-(5-fluoromethyl-[1,1'-biphenyl]yl)sulfamoyl)phenyl)heptanoic acid (10); 6-{3-[(2,4,6-trimethylphenyl)sulfamoyl]phenyl}hexanoic acid (11); 7-(3-(N-(3,5-dimethyl-1H-pyrazolyl)sulfamoyl)phenyl)heptanoic acid (12); 7-(3-(N-(2,4-dimethylthiazolyl)sulfamoyl)phenyl)heptanoic acid (13); 7-(3-(N-(4,5-dimethylthiazolyl)sulfamoyl)phenyl)heptanoic acid (14); 7-(3-(N-(4,5-dimethyloxazolyl)sulfamoyl)phenyl)heptanoic acid (15); 7-(3-(N-(5-phenyl-1,2,4-thiadiazolyl)sulfamoyl)phenyl)heptanoic acid (16); N-(3-methyl-1,2,4-thiadiazolyl)sulfamoyl)phenyl)heptanoic acid (17); 7-(3-(N-(5-methyl-1,3,4-thiadiazolyl)sulfamoyl)phenyl)heptanoic acid (18); 7-(3-(N-(3,5-dimethylisoxazolyl)sulfamoyl)phenyl)heptanoic acid (19); 7-(3-(N-(5-methyl-4H-1,2,4-triazolyl)sulfamoyl)phenyl)heptanoic acid (20); 7-(3-(N-(3,5-dimethyl-4H-1,2,4-triazolyl)sulfamoyl)phenyl)heptanoic acid (21); 7-(3-(N-(3-phenylisothiazolyl)sulfamoyl)phenyl)heptanoic acid (22); 7-{3-[(5-hydroxynaphthalenyl)sulfamoyl]phenyl}heptanoic acid (23); 7-{3-[(4-fluoro-2,6-dimethylbenzoyl)sulfamoyl]phenyl}heptanoic acid (24); 7-{4-[(4-fluoro-2,6-dimethylphenyl)sulfamoyl]phenyl}heptanoic acid (25); 7-(3-(N-(2-ethyl-2H-1,2,3-triazolyl)sulfamoyl)phenyl)heptanoic acid (26); N-(2-methyl-2H-tetrazolyl)sulfamoyl)phenyl)heptanoic acid (27); N-(4-methyl-4,5-dihydrooxazolyl)sulfamoyl)phenyl)heptanoic acid (28); 7-(3-(N-(3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazol-2yl)sulfamoyl)phenyl) heptanoic acid (29); 7-(3-(N-(3-phenylisothiazolyl)sulfamoyl)phenyl)heptanoic acid (30); 7-(3-(N-(4-hydroxy-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (31); 7-(3-(N-(3,5-dimethyl-[1,1'-biphenyl]yl)sulfamoyl)phenyl)heptanoic acid (32); 7-(3-(N-(2,6-dimethylphenoxyphenyl)sulfamoyl)phenyl)heptanoic acid (33); 7-(3-(N-(4-(benzyloxy)-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (34); 7-(3-(N-(2,6-dimethyl(3(methylsulfonyl)propoxy)phenyl)sulfamoyl)phenyl)heptanoic acid (35).
8. A compound according to claim 7 selected from: 7-(3-(N-(4-fluoro-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (1); 7-(3-(N-(2,4,6-trimethylbenzyl)sulfamoyl)phenyl)heptanoic acid (2); 7-(3-(N-(4-isopropyl-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (3); 7-(3-(N-(4-chloro-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (4); 7-(3-(N-(2,6-dimethyl(trifluoromethyl)phenyl)sulfamoyl)phenyl)heptanoic acid (6); 7-(3-(N-(4-bromo-2,6-dimethylphenyl)sulfamoyl)phenyl)heptanoic acid (7) 7-(3-(N-(6-fluoromethyl-[1,1'-biphenyl]yl)sulfamoyl)phenyl)heptanoic acid (9); 7-(3-(N-(5-fluoromethyl-[1,1'-biphenyl]yl)sulfamoyl)phenyl)heptanoic acid (10); 6-{3-[(2,4,6-trimethylphenyl)sulfamoyl]phenyl}hexanoic acid (11); 7-(3-(N-(2,6-dimethylphenoxyphenyl)sulfamoyl)phenyl)heptanoic acid (33).
9. A compound according to anyone of claims 1 to 8, for use as a medicament.
10. A compound for use according to claim 9, in the tion and/or treatment of a disease or disorder modulated by GPR
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16183294.4A EP3281937A1 (en) | 2016-08-09 | 2016-08-09 | Sulfonamides as gpr40- and gpr120-agonists |
PCT/EP2017/069958 WO2018029150A1 (en) | 2016-08-09 | 2017-08-07 | Sulfonamides as gpr40- and gpr120-agonists |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ750252A NZ750252A (en) | 2023-12-22 |
NZ750252B2 true NZ750252B2 (en) | 2024-03-26 |
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