HRP980044A2 - Thiazole benzenesulfonamides as beta3 antagonists for the treatment of diabetes and obesity - Google Patents
Thiazole benzenesulfonamides as beta3 antagonists for the treatment of diabetes and obesityInfo
- Publication number
- HRP980044A2 HRP980044A2 HR9705041.3A HRP980044A HRP980044A2 HR P980044 A2 HRP980044 A2 HR P980044A2 HR P980044 A HRP980044 A HR P980044A HR P980044 A2 HRP980044 A2 HR P980044A2
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- phenyl
- hydroxy
- benzenesulfonamide
- amino
- Prior art date
Links
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 8
- 208000008589 Obesity Diseases 0.000 title claims description 6
- 235000020824 obesity Nutrition 0.000 title claims description 6
- 239000005557 antagonist Substances 0.000 title description 3
- MYEFHJZLNOFLNK-UHFFFAOYSA-N benzenesulfonamide;1,3-thiazole Chemical class C1=CSC=N1.NS(=O)(=O)C1=CC=CC=C1 MYEFHJZLNOFLNK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 30
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 30
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 29
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 229910052757 nitrogen Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Chemical group 0.000 claims description 23
- -1 (3) naphthyl Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 235000019256 formaldehyde Nutrition 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000001079 digestive effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 4
- KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical group NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000008991 intestinal motility Effects 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- PVFRBOLJUSQATI-UHFFFAOYSA-N 4-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C=2SC=C(N=2)C=2OC3=CC=CC=C3C=2)C=CC=1CCNCC(O)C1=CC=CN=C1 PVFRBOLJUSQATI-UHFFFAOYSA-N 0.000 claims description 2
- NBFWPPOLIJRMER-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C=2SC=C(N=2)C=2SC3=CC=CC=C3C=2)C=CC=1CCNCC(O)C1=CC=CN=C1 NBFWPPOLIJRMER-UHFFFAOYSA-N 0.000 claims description 2
- ZLVDGVNOJUFGPG-UHFFFAOYSA-N 4-[4-(2,3-difluorophenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=CC(F)=C1F ZLVDGVNOJUFGPG-UHFFFAOYSA-N 0.000 claims description 2
- SICDBIYRCXMTLV-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(Cl)C=C1Cl SICDBIYRCXMTLV-UHFFFAOYSA-N 0.000 claims description 2
- XWAXZZKYNRSMJU-UHFFFAOYSA-N 4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(F)C=C1F XWAXZZKYNRSMJU-UHFFFAOYSA-N 0.000 claims description 2
- ZSOINIDVRRDQNP-UHFFFAOYSA-N 4-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(O)C(O)=C1 ZSOINIDVRRDQNP-UHFFFAOYSA-N 0.000 claims description 2
- HOQQTCAAVAEYCQ-UHFFFAOYSA-N 4-[4-(4-tert-butylphenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CSC(C=2C=CC(=CC=2)S(=O)(=O)NC=2C=CC(CCNCC(O)C=3C=NC=CC=3)=CC=2)=N1 HOQQTCAAVAEYCQ-UHFFFAOYSA-N 0.000 claims description 2
- ADQJEVIVPNIQEK-UHFFFAOYSA-N 4-[4-[(3,4-difluorophenyl)methyl]-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1CC1=CC=C(F)C(F)=C1 ADQJEVIVPNIQEK-UHFFFAOYSA-N 0.000 claims description 2
- AFPDIGDFXWUUDZ-UHFFFAOYSA-N 4-[4-[2,4-bis(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(C(F)(F)F)C=C1C(F)(F)F AFPDIGDFXWUUDZ-UHFFFAOYSA-N 0.000 claims description 2
- AGBWYUQFXJPPOT-UHFFFAOYSA-N 4-[4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(C(F)(F)F)C=C1F AGBWYUQFXJPPOT-UHFFFAOYSA-N 0.000 claims description 2
- NASHIEBAWSHTIO-UHFFFAOYSA-N 4-[4-[4-(difluoromethyl)phenyl]-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(C(F)F)C=C1 NASHIEBAWSHTIO-UHFFFAOYSA-N 0.000 claims description 2
- KOYHETGDZIVUHM-UHFFFAOYSA-N 4-[4-[4-fluoro-2-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(F)C=C1C(F)(F)F KOYHETGDZIVUHM-UHFFFAOYSA-N 0.000 claims description 2
- YUXRZMJBOMYGHS-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-(3,4,5-trifluorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC(F)=C(F)C(F)=C1 YUXRZMJBOMYGHS-UHFFFAOYSA-N 0.000 claims description 2
- ADOUHIKUSVYGDB-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-(naphthalen-2-ylmethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C=2SC=C(CC=3C=C4C=CC=CC4=CC=3)N=2)C=CC=1CCNCC(O)C1=CC=CN=C1 ADOUHIKUSVYGDB-UHFFFAOYSA-N 0.000 claims description 2
- LJHFZRFLGDYKHF-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[2-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=CC=C1C(F)(F)F LJHFZRFLGDYKHF-UHFFFAOYSA-N 0.000 claims description 2
- YRGWQUSTRJHRQE-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(OC(F)(F)F)C=C1 YRGWQUSTRJHRQE-UHFFFAOYSA-N 0.000 claims description 2
- MSOUIIHPMJCUNI-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=C(C(F)(F)F)C=C1 MSOUIIHPMJCUNI-UHFFFAOYSA-N 0.000 claims description 2
- IZYGPTKZMIMWKI-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[[4-(trifluoromethoxy)phenoxy]methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1COC1=CC=C(OC(F)(F)F)C=C1 IZYGPTKZMIMWKI-UHFFFAOYSA-N 0.000 claims description 2
- OZIDOJODOXJIKM-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[[4-(trifluoromethoxy)phenyl]methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1CC1=CC=C(OC(F)(F)F)C=C1 OZIDOJODOXJIKM-UHFFFAOYSA-N 0.000 claims description 2
- RNJSCWARWRHCEN-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1CC1=CC=C(C(F)(F)F)C=C1 RNJSCWARWRHCEN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 6
- 102000015779 HDL Lipoproteins Human genes 0.000 claims 3
- 108010010234 HDL Lipoproteins Proteins 0.000 claims 3
- 235000012000 cholesterol Nutrition 0.000 claims 3
- 150000003626 triacylglycerols Chemical class 0.000 claims 3
- XBENZUSXFSYEEC-UHFFFAOYSA-N 4-[4-(3,5-difluorophenyl)-1,3-thiazol-2-yl]-n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC(F)=CC(F)=C1 XBENZUSXFSYEEC-UHFFFAOYSA-N 0.000 claims 1
- PXQITGQLJXJUBG-UHFFFAOYSA-N n-[4-[2-[(2-hydroxy-2-pyridin-3-ylethyl)amino]ethyl]phenyl]-4-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(O)CNCCC(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C(SC=1)=NC=1C1=CC=CC(C(F)(F)F)=C1 PXQITGQLJXJUBG-UHFFFAOYSA-N 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
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- 108020003175 receptors Proteins 0.000 description 11
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
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- 125000000623 heterocyclic group Chemical group 0.000 description 7
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Classifications
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- 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
-
- 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
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3676097P | 1997-01-28 | 1997-01-28 | |
| GBGB9705041.3A GB9705041D0 (en) | 1997-03-12 | 1997-03-12 | Thiazole benzenesulfonamides as selective B3 agonists for the treatment of diabetes and obesity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980044A2 true HRP980044A2 (en) | 1998-10-31 |
Family
ID=26311166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR9705041.3A HRP980044A2 (en) | 1997-01-28 | 1998-01-28 | Thiazole benzenesulfonamides as beta3 antagonists for the treatment of diabetes and obesity |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0968209A1 (zh) |
| JP (1) | JP2001509166A (zh) |
| KR (1) | KR20000070568A (zh) |
| CN (1) | CN1251099A (zh) |
| AR (1) | AR011092A1 (zh) |
| AU (1) | AU728812B2 (zh) |
| BG (1) | BG103686A (zh) |
| BR (1) | BR9807096A (zh) |
| CA (1) | CA2278739A1 (zh) |
| EA (1) | EA199900692A1 (zh) |
| EE (1) | EE9900328A (zh) |
| HR (1) | HRP980044A2 (zh) |
| HU (1) | HUP0002053A3 (zh) |
| ID (1) | ID22273A (zh) |
| IL (1) | IL131130A0 (zh) |
| IS (1) | IS5131A (zh) |
| NO (1) | NO993646L (zh) |
| PE (1) | PE52299A1 (zh) |
| PL (1) | PL334833A1 (zh) |
| SK (1) | SK100099A3 (zh) |
| TR (1) | TR199902442T2 (zh) |
| WO (1) | WO1998032753A1 (zh) |
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| EP1741447B1 (en) | 2000-01-21 | 2013-09-18 | Novartis AG | Combinations comprising dipeptidylpeptidase-IV inhibitors and antidiabetic agents |
| US20030018061A1 (en) * | 2000-01-28 | 2003-01-23 | Kohei Ogawa | Novel remedies with the use of beta 3 agonist |
| ATE267204T1 (de) * | 2000-03-31 | 2004-06-15 | Pfizer Prod Inc | Verfahren zur herstellung von substituierten pyridinen |
| US6730792B2 (en) * | 2000-07-13 | 2004-05-04 | Eli Lilly And Company | β3 adrenergic agonists |
| US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
| US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| US6410734B1 (en) | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US6369232B1 (en) * | 2000-08-15 | 2002-04-09 | Hoffmann-La Roche Inc. | Tetrazolyl-phenyl acetamide glucokinase activators |
| DE60120748T2 (de) | 2000-11-10 | 2007-05-16 | Eli Lilly And Co., Indianapolis | 3-substituierte oxindolderivate als beta-3-agonisten |
| EP1348706B1 (en) | 2000-12-08 | 2009-08-19 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| AR035605A1 (es) | 2000-12-11 | 2004-06-16 | Bayer Corp | Derivados de aminometil cromano di-sustituidos, un metodo para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la manufactura de medicamentos utiles como agonistas beta-3-adreno-receptores |
| AR035858A1 (es) | 2001-04-23 | 2004-07-21 | Bayer Corp | Derivados de cromano 2,6-sustituidos,composiciones farmaceuticas,uso de dichos derivados para la manufactura de medicamentos utiles como agonistas adrenorreceptores beta-3 |
| WO2003000687A1 (en) * | 2001-06-22 | 2003-01-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| DE60215028T2 (de) | 2001-08-14 | 2007-03-15 | Eli Lilly And Co., Indianapolis | Indol derivate als beta-3-adrenerge agonisten zur behandlung von typ 2 diabetes |
| ATE325119T1 (de) | 2001-08-14 | 2006-06-15 | Lilly Co Eli | 3-substituierte oxindol-beta-3-agonisten |
| CA2463441A1 (en) * | 2001-10-12 | 2003-05-08 | Bayer Pharmaceuticals Corporation | Phenyl substituted 5-membered nitrogen containing heterocycles for the treatment of obesity |
| DE60225174T2 (de) | 2001-11-20 | 2009-02-12 | Eli Lilly And Co., Indianapolis | Beta-3 adrenergische agonisten |
| WO2003044016A1 (en) | 2001-11-20 | 2003-05-30 | Eli Lilly And Company | 3-SUBSTITUTED OXINDOLE β3 AGONISTS |
| AU2002357084A1 (en) | 2002-01-11 | 2003-07-30 | Eli Lilly And Company | 2-oxo-benzimidazolyl substituted ethanolamine derivatives and their use as beta3 agonists |
| US6872724B2 (en) | 2002-07-24 | 2005-03-29 | Merck & Co., Inc. | Polymorphs with tyrosine kinase activity |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| WO2006132196A1 (ja) * | 2005-06-08 | 2006-12-14 | Asahi Kasei Pharma Corporation | β３作動薬を含有する新規な医薬 |
| WO2007033266A2 (en) | 2005-09-14 | 2007-03-22 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors for treating diabetis |
| JP4879988B2 (ja) | 2005-09-29 | 2012-02-22 | メルク・シャープ・エンド・ドーム・コーポレイション | メラノコルチン−４受容体モジュレーターとしてのアシル化スピロピペリジン誘導体 |
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| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| US7879802B2 (en) | 2007-06-04 | 2011-02-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2741672A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2011041293A1 (en) | 2009-09-30 | 2011-04-07 | Takeda Pharmaceutical Company Limited | Pyrazolo [1, 5-a] pyrimidine derivatives as apoptosis signal-regulating kinase 1 inhibitors |
| SI2531501T1 (sl) | 2010-02-03 | 2014-04-30 | Takeda Pharmaceutical Company Limited | Inhibitorji kinaze-1, ki regulirajo signal apoptoze |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
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| US20140045746A1 (en) | 2012-08-02 | 2014-02-13 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| ES2394349B1 (es) | 2012-08-29 | 2013-11-04 | Fundación Centro Nacional De Investigaciones Cardiovasculares Carlos Iii | Uso de agonistas selectivos de receptores beta-3 adrenérgicos para el tratamiento de hipertensión pulmonar |
| WO2014108449A1 (en) | 2013-01-08 | 2014-07-17 | Atrogi Ab | A screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| US9840512B2 (en) | 2013-02-22 | 2017-12-12 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| BR112015030326A2 (pt) | 2013-06-05 | 2017-08-29 | Synergy Pharmaceuticals Inc | Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2018106518A1 (en) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0091749A3 (en) * | 1982-04-08 | 1984-12-05 | Beecham Group Plc | Ethanolamine derivatives, process for their preparation and pharmaceutical compositions containing them |
| US5451677A (en) * | 1993-02-09 | 1995-09-19 | Merck & Co., Inc. | Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity |
| IL113410A (en) * | 1994-04-26 | 1999-11-30 | Merck & Co Inc | Substituted sulfonamides having an asymmetric center and pharmaceutical compositions containing them |
-
1998
- 1998-01-23 EA EA199900692A patent/EA199900692A1/ru unknown
- 1998-01-23 ID IDW990755A patent/ID22273A/id unknown
- 1998-01-23 PL PL98334833A patent/PL334833A1/xx unknown
- 1998-01-23 AU AU60384/98A patent/AU728812B2/en not_active Ceased
- 1998-01-23 WO PCT/US1998/001317 patent/WO1998032753A1/en not_active Application Discontinuation
- 1998-01-23 IL IL13113098A patent/IL131130A0/xx unknown
- 1998-01-23 CN CN98803585A patent/CN1251099A/zh active Pending
- 1998-01-23 SK SK1000-99A patent/SK100099A3/sk unknown
- 1998-01-23 EE EEP199900328A patent/EE9900328A/xx unknown
- 1998-01-23 JP JP53214898A patent/JP2001509166A/ja active Pending
- 1998-01-23 HU HU0002053A patent/HUP0002053A3/hu unknown
- 1998-01-23 EP EP98903677A patent/EP0968209A1/en not_active Withdrawn
- 1998-01-23 CA CA002278739A patent/CA2278739A1/en not_active Abandoned
- 1998-01-23 BR BR9807096-7A patent/BR9807096A/pt not_active IP Right Cessation
- 1998-01-23 KR KR1019997006814A patent/KR20000070568A/ko not_active Application Discontinuation
- 1998-01-23 TR TR1999/02442T patent/TR199902442T2/xx unknown
- 1998-01-27 AR ARP980100357A patent/AR011092A1/es unknown
- 1998-01-28 PE PE1998000064A patent/PE52299A1/es not_active Application Discontinuation
- 1998-01-28 HR HR9705041.3A patent/HRP980044A2/hr not_active Application Discontinuation
-
1999
- 1999-07-23 IS IS5131A patent/IS5131A/is unknown
- 1999-07-27 NO NO993646A patent/NO993646L/no not_active Application Discontinuation
- 1999-08-24 BG BG103686A patent/BG103686A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA199900692A1 (ru) | 2000-02-28 |
| TR199902442T2 (xx) | 2000-07-21 |
| AR011092A1 (es) | 2000-08-02 |
| AU6038498A (en) | 1998-08-18 |
| BR9807096A (pt) | 2000-04-18 |
| WO1998032753A1 (en) | 1998-07-30 |
| PE52299A1 (es) | 1999-05-26 |
| SK100099A3 (en) | 2000-05-16 |
| JP2001509166A (ja) | 2001-07-10 |
| HUP0002053A3 (en) | 2001-09-28 |
| AU728812B2 (en) | 2001-01-18 |
| EE9900328A (et) | 2000-02-15 |
| KR20000070568A (ko) | 2000-11-25 |
| EP0968209A1 (en) | 2000-01-05 |
| ID22273A (id) | 1999-09-23 |
| NO993646D0 (no) | 1999-07-27 |
| PL334833A1 (en) | 2000-03-27 |
| NO993646L (no) | 1999-09-27 |
| CN1251099A (zh) | 2000-04-19 |
| IL131130A0 (en) | 2001-01-28 |
| HUP0002053A2 (hu) | 2001-08-28 |
| CA2278739A1 (en) | 1998-07-30 |
| BG103686A (bg) | 2000-06-30 |
| IS5131A (is) | 1999-07-23 |
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