JP2008503575A - ５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボキサミド又は５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボン酸の新規な誘導体 - Google Patents
５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボキサミド又は５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボン酸の新規な誘導体 Download PDFInfo
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- JP2008503575A JP2008503575A JP2007518004A JP2007518004A JP2008503575A JP 2008503575 A JP2008503575 A JP 2008503575A JP 2007518004 A JP2007518004 A JP 2007518004A JP 2007518004 A JP2007518004 A JP 2007518004A JP 2008503575 A JP2008503575 A JP 2008503575A
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- JP
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- Prior art keywords
- alkyl
- pyrrolo
- pyridine
- phenyl
- carboxamide hydrochloride
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000012458 free base Substances 0.000 claims abstract description 7
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 177
- -1 OR 13 Chemical group 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 38
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 29
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 27
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 26
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 208000010877 cognitive disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 206010012289 Dementia Diseases 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 230000002265 prevention Effects 0.000 claims description 19
- 208000024827 Alzheimer disease Diseases 0.000 claims description 18
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 10
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 10
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- ADPVVAWRYYOKPY-UHFFFAOYSA-N methyl 5-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 ADPVVAWRYYOKPY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000006999 cognitive decline Effects 0.000 claims description 7
- RKPTVBINMGGGER-UHFFFAOYSA-N methyl 5-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1OC(F)(F)F)=CC=C1S(=O)(=O)N1CCN(C)CC1 RKPTVBINMGGGER-UHFFFAOYSA-N 0.000 claims description 7
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- JOGDOWSSXITRFY-UHFFFAOYSA-N methyl 5-(4-piperidin-1-ylsulfonylphenyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 JOGDOWSSXITRFY-UHFFFAOYSA-N 0.000 claims description 6
- VLJMSHQPVFKFNQ-UHFFFAOYSA-N methyl 5-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1OCCN1CCOCC1 VLJMSHQPVFKFNQ-UHFFFAOYSA-N 0.000 claims description 6
- MDFGMUGWHGCMGJ-UHFFFAOYSA-N methyl 5-[4-(morpholin-4-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCOCC1 MDFGMUGWHGCMGJ-UHFFFAOYSA-N 0.000 claims description 6
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- 230000007423 decrease Effects 0.000 claims description 5
- KPZAJMHJJSYSIH-UHFFFAOYSA-N methyl 5-[4-(piperidin-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCCCC1 KPZAJMHJJSYSIH-UHFFFAOYSA-N 0.000 claims description 5
- SXLCEUHWLMKILH-UHFFFAOYSA-N methyl 5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1OCCN1CCN(C)CC1 SXLCEUHWLMKILH-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- YIXPNXNGBUFBFA-UHFFFAOYSA-N methyl 5-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCN(C)CC1 YIXPNXNGBUFBFA-UHFFFAOYSA-N 0.000 claims description 4
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- MOPSEUHKLBOUBD-UHFFFAOYSA-N 5-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-n-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C=C3C(C(=O)NC=4C=NC=CC=4)=CNC3=NC=2)C=C1OC(F)(F)F MOPSEUHKLBOUBD-UHFFFAOYSA-N 0.000 claims description 3
- LAWGIDINEOJMHR-UHFFFAOYSA-N 5-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-(2-methylsulfonylphenyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C=C3C(C(=O)NC=4C(=CC=CC=4)S(C)(=O)=O)=CNC3=NC=2)C=C1 LAWGIDINEOJMHR-UHFFFAOYSA-N 0.000 claims description 3
- CZKAYKXAZLJSJO-UHFFFAOYSA-N 5-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C=C3C(C(=O)NC=4C=NC=CC=4)=CNC3=NC=2)C=C1 CZKAYKXAZLJSJO-UHFFFAOYSA-N 0.000 claims description 3
- DMFRLUSFAKKQHL-UHFFFAOYSA-N 5-[4-(morpholin-4-ylmethyl)phenyl]-n-(2-thiophen-2-ylethyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC2=NC=C(C=3C=CC(CN4CCOCC4)=CC=3)C=C2C=1C(=O)NCCC1=CC=CS1 DMFRLUSFAKKQHL-UHFFFAOYSA-N 0.000 claims description 3
- OVQZOSHVSHCOTM-UHFFFAOYSA-N 5-[4-(morpholin-4-ylmethyl)phenyl]-n-pentyl-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCCCC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCOCC1 OVQZOSHVSHCOTM-UHFFFAOYSA-N 0.000 claims description 3
- CBHFIEXHLUUFGN-UHFFFAOYSA-N 5-[4-(morpholine-4-carbonyl)phenyl]-n-(2-morpholin-4-ylethyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC2=NC=C(C=3C=CC(=CC=3)C(=O)N3CCOCC3)C=C2C=1C(=O)NCCN1CCOCC1 CBHFIEXHLUUFGN-UHFFFAOYSA-N 0.000 claims description 3
- KNNMGWDEKLAPNM-UHFFFAOYSA-N 5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-n-(2-morpholin-4-ylethyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCOC1=CC=C(C=2C=C3C(C(=O)NCCN4CCOCC4)=CNC3=NC=2)C=C1 KNNMGWDEKLAPNM-UHFFFAOYSA-N 0.000 claims description 3
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- CIVGJWQASHLUIB-UHFFFAOYSA-N n-(2-methoxyethyl)-5-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCOC)=CNC2=NC=C1C(C=C1OC(F)(F)F)=CC=C1S(=O)(=O)N1CCN(C)CC1 CIVGJWQASHLUIB-UHFFFAOYSA-N 0.000 claims description 3
- QQHFMFZTTUYYTR-UHFFFAOYSA-N n-(2-methoxyethyl)-5-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCOC)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 QQHFMFZTTUYYTR-UHFFFAOYSA-N 0.000 claims description 3
- DZVALETZZKJKHB-UHFFFAOYSA-N n-(2-methoxyethyl)-5-[4-(morpholin-4-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCOC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCOCC1 DZVALETZZKJKHB-UHFFFAOYSA-N 0.000 claims description 3
- HQUHZVGGORWCKS-UHFFFAOYSA-N n-(2-methoxyphenyl)-5-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1NC(=O)C1=CNC2=NC=C(C=3C=CC(OCCN4CCOCC4)=CC=3)C=C12 HQUHZVGGORWCKS-UHFFFAOYSA-N 0.000 claims description 3
- JLIARJJCFWZYJF-UHFFFAOYSA-N n-(2-methylsulfonylethyl)-5-(4-piperidin-1-ylsulfonylphenyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCS(=O)(=O)C)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 JLIARJJCFWZYJF-UHFFFAOYSA-N 0.000 claims description 3
- GLJHFOBNGHWZKT-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-5-(4-morpholin-4-ylphenyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC2=NC=C(C=3C=CC(=CC=3)N3CCOCC3)C=C2C=1C(=O)NCCN1CCOCC1 GLJHFOBNGHWZKT-UHFFFAOYSA-N 0.000 claims description 3
- IGCLRWGJKMYGMQ-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-5-[4-(pyrrolidine-1-carbonyl)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC2=NC=C(C=3C=CC(=CC=3)C(=O)N3CCCC3)C=C2C=1C(=O)NCCN1CCOCC1 IGCLRWGJKMYGMQ-UHFFFAOYSA-N 0.000 claims description 3
- PKHIOSKRCXIXEL-UHFFFAOYSA-N n-(3-methoxyphenyl)-5-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.COC1=CC=CC(NC(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(OCCN3CCOCC3)=CC=2)=C1 PKHIOSKRCXIXEL-UHFFFAOYSA-N 0.000 claims description 3
- ZBBWWSOHXXECEN-UHFFFAOYSA-N n-(3-methoxypropyl)-5-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCCOC)=CNC2=NC=C1C(C=C1)=CC=C1OCCN1CCOCC1 ZBBWWSOHXXECEN-UHFFFAOYSA-N 0.000 claims description 3
- AXTDIAFHYUBGBD-UHFFFAOYSA-N n-(3-methoxypropyl)-5-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCCOC)=CNC2=NC=C1C(C=C1OC(F)(F)F)=CC=C1S(=O)(=O)N1CCN(C)CC1 AXTDIAFHYUBGBD-UHFFFAOYSA-N 0.000 claims description 3
- WQQDQYCMHVMYQE-UHFFFAOYSA-N n-(3-methoxypropyl)-5-[4-(piperidin-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCCOC)=CNC2=NC=C1C(C=C1)=CC=C1CN1CCCCC1 WQQDQYCMHVMYQE-UHFFFAOYSA-N 0.000 claims description 3
- AFWGUKWVTZFRSU-UHFFFAOYSA-N n-(3-methoxypropyl)-5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NCCCOC)=CNC2=NC=C1C(C=C1)=CC=C1OCCN1CCN(C)CC1 AFWGUKWVTZFRSU-UHFFFAOYSA-N 0.000 claims description 3
- KVDXAKICNTWMQL-UHFFFAOYSA-N n-methyl-5-(4-piperidin-1-ylsulfonylphenyl)-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NC)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 KVDXAKICNTWMQL-UHFFFAOYSA-N 0.000 claims description 3
- LBKRARXZMZIRGK-UHFFFAOYSA-N n-methyl-5-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NC)=CNC2=NC=C1C(C=C1OC(F)(F)F)=CC=C1S(=O)(=O)N1CCN(C)CC1 LBKRARXZMZIRGK-UHFFFAOYSA-N 0.000 claims description 3
- SMEMVHDJBVTJHC-UHFFFAOYSA-N n-methyl-5-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2C(C(=O)NC)=CNC2=NC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 SMEMVHDJBVTJHC-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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- 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 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 210000001519 tissue Anatomy 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P15/16—Masculine 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
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- AIDS & HIV (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0401655A SE0401655D0 (sv) | 2004-06-24 | 2004-06-24 | New compounds |
| PCT/SE2005/000955 WO2006001754A1 (en) | 2004-06-24 | 2005-06-20 | New derivatives of 5-aryl-1h-pyrrolo [2, 3b] pyridine-3-carboxamide or 5-aryl-1h-pyrrolo [2, 3b] pyridine-3-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008503575A true JP2008503575A (ja) | 2008-02-07 |
| JP2008503575A5 JP2008503575A5 (enExample) | 2008-07-31 |
Family
ID=32733685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007518004A Pending JP2008503575A (ja) | 2004-06-24 | 2005-06-20 | ５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボキサミド又は５−アリール−１ｈ−ピロロ［２，３ｂ］ピリジン−３−カルボン酸の新規な誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20090018130A1 (enExample) |
| EP (1) | EP1761530A1 (enExample) |
| JP (1) | JP2008503575A (enExample) |
| CN (1) | CN1972943A (enExample) |
| AR (1) | AR049650A1 (enExample) |
| SE (1) | SE0401655D0 (enExample) |
| TW (1) | TW200606164A (enExample) |
| UY (1) | UY28979A1 (enExample) |
| WO (1) | WO2006001754A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004054634A1 (de) * | 2004-11-12 | 2006-05-18 | Schwarz Pharma Ag | Azaindolcarboxamide |
| WO2009017453A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958 |
| WO2009017454A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of a gsk3 inhibitor and an a7-nicotinic agonist 960 |
| WO2009017455A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | A new combination of (a) an alpha-4-beta-2 -neuronal nicotinic agonist and (b) a gsk3 inhibitor |
| PE20110365A1 (es) | 2008-06-11 | 2011-07-11 | Genentech Inc | Diazacarbazoles como inhibidores de checkpoint quinasa 1 (chk1) |
| US20110183938A1 (en) | 2009-12-16 | 2011-07-28 | Genentech, Inc. | 1,7-diazacarbazoles and methods of use |
| EP2582666B1 (en) | 2010-06-16 | 2014-08-13 | Purdue Pharma L.P. | Aryl substituted indoles and their use as blockers of sodium channels |
| JP2017524739A (ja) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | 神経筋接合部関連疾患の処置方法 |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| KR101746199B1 (ko) | 2016-07-04 | 2017-06-13 | 기초과학연구원 | 질소 함유 헤테로아릴 유도체 및 GSK3β 저해제로서의 이의 용도 |
| CA3098988A1 (en) * | 2018-05-02 | 2019-11-07 | Jw Pharmaceutical Corporation | Heterocycle derivative |
| CN110041328A (zh) * | 2019-05-22 | 2019-07-23 | 南京合巨药业有限公司 | 一种5-氟-1H-吡咯并[2,3-b]吡啶-3-羧酸的制备方法 |
| AU2022309278A1 (en) * | 2021-07-16 | 2024-02-22 | Aphiotx Inc. | Sulfamoyl benzene derivatives and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074768A1 (en) * | 2001-03-16 | 2002-09-26 | Smithkline Beecham Plc | Piperazine derivatives, their preparation and uses in therapy (5ht1b receptor activity) |
| WO2003082868A1 (en) * | 2002-03-28 | 2003-10-09 | Eisai Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
-
2004
- 2004-06-24 SE SE0401655A patent/SE0401655D0/xx unknown
-
2005
- 2005-06-13 TW TW094119531A patent/TW200606164A/zh unknown
- 2005-06-17 AR ARP050102505A patent/AR049650A1/es unknown
- 2005-06-20 CN CNA200580021231XA patent/CN1972943A/zh active Pending
- 2005-06-20 US US11/571,183 patent/US20090018130A1/en not_active Abandoned
- 2005-06-20 WO PCT/SE2005/000955 patent/WO2006001754A1/en not_active Ceased
- 2005-06-20 JP JP2007518004A patent/JP2008503575A/ja active Pending
- 2005-06-20 EP EP05754098A patent/EP1761530A1/en not_active Withdrawn
- 2005-06-23 UY UY28979A patent/UY28979A1/es not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074768A1 (en) * | 2001-03-16 | 2002-09-26 | Smithkline Beecham Plc | Piperazine derivatives, their preparation and uses in therapy (5ht1b receptor activity) |
| WO2003082868A1 (en) * | 2002-03-28 | 2003-10-09 | Eisai Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1972943A (zh) | 2007-05-30 |
| US20090018130A1 (en) | 2009-01-15 |
| EP1761530A1 (en) | 2007-03-14 |
| TW200606164A (en) | 2006-02-16 |
| SE0401655D0 (sv) | 2004-06-24 |
| WO2006001754A1 (en) | 2006-01-05 |
| AR049650A1 (es) | 2006-08-23 |
| UY28979A1 (es) | 2006-01-31 |
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