SK15432003A3 - 5-Substituované 2-arylpyridíny - Google Patents
5-Substituované 2-arylpyridíny Download PDFInfo
- Publication number
- SK15432003A3 SK15432003A3 SK1543-2003A SK15432003A SK15432003A3 SK 15432003 A3 SK15432003 A3 SK 15432003A3 SK 15432003 A SK15432003 A SK 15432003A SK 15432003 A3 SK15432003 A3 SK 15432003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- alkoxy
- amino
- halogen
- mono
- Prior art date
Links
- 102100038018 Corticotropin-releasing factor receptor 1 Human genes 0.000 title 1
- 101000878678 Homo sapiens Corticotropin-releasing factor receptor 1 Proteins 0.000 title 1
- 101000948733 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Probable phospholipid translocase non-catalytic subunit CRF1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 360
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
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- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 12
- 230000036506 anxiety Effects 0.000 claims abstract description 12
- -1 C 4 hydrocarbons Chemical class 0.000 claims description 202
- 229910052736 halogen Inorganic materials 0.000 claims description 173
- 150000002367 halogens Chemical class 0.000 claims description 143
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 125
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
- 125000004432 carbon atom Chemical group C* 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
- 239000001257 hydrogen Substances 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 75
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 57
- 102100021752 Corticoliberin Human genes 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000004043 oxo group Chemical group O=* 0.000 claims description 39
- 229920006395 saturated elastomer Polymers 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 210000004027 cell Anatomy 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 108091005471 CRHR1 Proteins 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 238000000338 in vitro Methods 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 239000012472 biological sample Substances 0.000 claims description 13
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 238000001525 receptor binding assay Methods 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 238000001727 in vivo Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 101710113174 Corticoliberin Proteins 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 6
- 210000001124 body fluid Anatomy 0.000 claims description 5
- 239000010839 body fluid Substances 0.000 claims description 5
- 238000011534 incubation Methods 0.000 claims description 5
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- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 238000000376 autoradiography Methods 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
- 210000002569 neuron Anatomy 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 150000001356 alkyl thiols Chemical class 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 102000005962 receptors Human genes 0.000 abstract description 27
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- 238000003556 assay Methods 0.000 abstract description 16
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- 208000030814 Eating disease Diseases 0.000 abstract 1
- 208000019454 Feeding and Eating disease Diseases 0.000 abstract 1
- 235000014632 disordered eating Nutrition 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 182
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 150
- 239000000243 solution Substances 0.000 description 75
- 235000019439 ethyl acetate Nutrition 0.000 description 61
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- 238000002360 preparation method Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 40
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 230000000694 effects Effects 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 208000035475 disorder Diseases 0.000 description 19
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- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 4
- VTOQFOCYBTVOJZ-UHFFFAOYSA-N 3-bromopentane Chemical compound CCC(Br)CC VTOQFOCYBTVOJZ-UHFFFAOYSA-N 0.000 description 4
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- AJCQJELUJDPGEY-UHFFFAOYSA-N [2-methoxy-4-(trifluoromethoxy)phenyl]boronic acid Chemical compound COC1=CC(OC(F)(F)F)=CC=C1B(O)O AJCQJELUJDPGEY-UHFFFAOYSA-N 0.000 description 4
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- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D213/63—One oxygen atom
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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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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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (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)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29270301P | 2001-05-22 | 2001-05-22 | |
| PCT/US2002/016529 WO2002096421A1 (en) | 2001-05-22 | 2002-05-22 | 5-substituted-2-arylpyridines as crf1 modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK15432003A3 true SK15432003A3 (sk) | 2004-05-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1543-2003A SK15432003A3 (sk) | 2001-05-22 | 2002-05-22 | 5-Substituované 2-arylpyridíny |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7223778B2 (https=) |
| EP (1) | EP1392302A1 (https=) |
| JP (1) | JP2004531570A (https=) |
| KR (1) | KR20040015716A (https=) |
| AP (1) | AP2003002920A0 (https=) |
| BG (1) | BG108490A (https=) |
| BR (1) | BR0209920A (https=) |
| CA (1) | CA2448198A1 (https=) |
| EC (1) | ECSP034860A (https=) |
| HR (1) | HRP20031056A2 (https=) |
| HU (1) | HUP0400316A2 (https=) |
| IL (1) | IL158958A0 (https=) |
| IS (1) | IS7046A (https=) |
| MX (1) | MXPA03010692A (https=) |
| NO (1) | NO20035183D0 (https=) |
| PL (1) | PL367153A1 (https=) |
| RU (1) | RU2003134010A (https=) |
| SK (1) | SK15432003A3 (https=) |
| TN (1) | TNSN03119A1 (https=) |
| WO (1) | WO2002096421A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7015227B2 (en) | 2002-06-21 | 2006-03-21 | Cgi Pharmaceuticals, Inc. | Certain amino-substituted monocycles as kinase modulators |
| ATE552253T1 (de) * | 2002-11-08 | 2012-04-15 | Novartis Int Pharm Ltd | 3-substituierte-6-aryl- pyridin derivate als liganden für c5a-rezeptoren |
| WO2005007627A1 (ja) * | 2003-07-18 | 2005-01-27 | Nihon Nohyaku Co., Ltd. | フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤 |
| JPWO2005040135A1 (ja) * | 2003-10-24 | 2007-03-08 | 小野薬品工業株式会社 | 抗ストレス薬およびその医薬用途 |
| RU2423979C2 (ru) * | 2005-06-17 | 2011-07-20 | АФТ Фармасьютикалз Лимитед | Новая фармацевтическая композиция и ее применение в способе лечения пациентов с гиперемией и отеком слизистой оболочки верхних дыхательных путей |
| CN102775396B (zh) | 2005-11-08 | 2014-10-08 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的杂环调控剂 |
| CN104447716A (zh) | 2007-05-09 | 2015-03-25 | 沃泰克斯药物股份有限公司 | Cftr调节剂 |
| DK2177512T3 (da) * | 2007-08-01 | 2012-06-18 | Taisho Pharmaceutical Co Ltd | S1P1-bindingshæmmer |
| MX365732B (es) * | 2007-12-07 | 2019-06-12 | Vertex Pharma | Procesos para producir acidos cicloalquilcarboxamido-piridin benzoicos. |
| EP3683218B1 (en) | 2007-12-07 | 2024-09-18 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| AU2013205160B2 (en) * | 2007-12-07 | 2016-05-19 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| NZ720282A (en) | 2008-02-28 | 2017-12-22 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| JP2013523833A (ja) | 2010-04-07 | 2013-06-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | 3−(6−(1−(2,2−ジフルオロベンゾ[d][1,3]ジオキソール−5−イル)シクロプロパンカルボキサミド)−3−メチルピリジン−2−イル)安息香酸の医薬組成物およびその投与 |
| NZ727015A (en) | 2012-01-25 | 2017-12-22 | Vertex Pharma | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| ES2848700T3 (es) * | 2012-03-30 | 2021-08-11 | Dow Agrosciences Llc | Procedimientos de preparación de 6-trifluorometil-piridinas 3-sustituidas y procedimientos de uso de 6-triclorometil-piridinas halogenadas |
| AU2014349010C1 (en) | 2013-11-12 | 2020-08-06 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases |
| RU2691136C2 (ru) | 2014-11-18 | 2019-06-11 | Вертекс Фармасьютикалз Инкорпорейтед | Способ проведения высокопроизводительной тестовой высокоэффективной жидкостной хроматографии |
| KR101750453B1 (ko) | 2015-09-11 | 2017-06-23 | 동아대학교 산학협력단 | 손잡이 세정이 가능한 샤워헤드용 방향제어밸브 |
| US10336701B2 (en) | 2017-08-10 | 2019-07-02 | Janssen Pharmaceutica Nv | Pyridin-2-one derivatives of formula (II) useful as EP3 receptor antagonists |
| US10590083B2 (en) | 2017-08-10 | 2020-03-17 | Janssen Pharmaceutica Nv | Pyridin-2-one derivatives of formula (I) useful as EP3 receptor antagonists |
| US10399944B2 (en) | 2017-08-10 | 2019-09-03 | Janssen Pharmaceutica Nv | Pyridin-2-one derivatives of formula (III) useful as EP3 receptor antagonists |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1147068A (en) | 1966-12-02 | 1969-04-02 | Ici Ltd | Phenyl-pyridine derivatives |
| GB9012017D0 (en) * | 1990-05-30 | 1990-07-18 | Ici Plc | Fungicidal compounds |
| DE4315867A1 (de) * | 1993-05-12 | 1994-11-17 | Hoechst Ag | 3-Chlorpyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Flüssigkristallmischungen |
| DE4323916A1 (de) | 1993-07-16 | 1995-01-19 | Basf Ag | Substituierte 2-Phenylpyridine |
| TW530047B (en) | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| US5849758A (en) * | 1995-05-30 | 1998-12-15 | American Cyanamid Company | Herbicidal 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines |
| DE19748439A1 (de) * | 1997-11-03 | 1999-05-06 | Hoechst Ag | 1,6-Disubstituierte Naphthalinderivate und ihre Verwendung in flüssigkristallinen Mischungen |
| CN1231473C (zh) | 2000-02-16 | 2005-12-14 | 神经能质公司 | 取代的芳基吡嗪 |
| AU4368001A (en) * | 2000-03-16 | 2001-09-24 | Neurogen Corporation | 5-substituted arylpyrimidines |
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2002
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- 2002-05-22 RU RU2003134010/04A patent/RU2003134010A/ru not_active Application Discontinuation
- 2002-05-22 MX MXPA03010692A patent/MXPA03010692A/es unknown
- 2002-05-22 BR BR0209920-9A patent/BR0209920A/pt not_active Application Discontinuation
- 2002-05-22 CA CA002448198A patent/CA2448198A1/en not_active Abandoned
- 2002-05-22 JP JP2002592931A patent/JP2004531570A/ja active Pending
- 2002-05-22 HR HR20031056A patent/HRP20031056A2/hr not_active Application Discontinuation
- 2002-05-22 PL PL02367153A patent/PL367153A1/xx not_active Application Discontinuation
- 2002-05-22 WO PCT/US2002/016529 patent/WO2002096421A1/en not_active Ceased
- 2002-05-22 AP APAP/P/2003/002920A patent/AP2003002920A0/en unknown
- 2002-05-22 US US10/154,396 patent/US7223778B2/en not_active Expired - Fee Related
- 2002-05-22 IL IL15895802A patent/IL158958A0/xx unknown
- 2002-05-22 EP EP02741732A patent/EP1392302A1/en not_active Withdrawn
- 2002-05-22 HU HU0400316A patent/HUP0400316A2/hu unknown
- 2002-05-22 SK SK1543-2003A patent/SK15432003A3/sk unknown
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2003
- 2003-07-08 TN TNPCT/US2002/016529A patent/TNSN03119A1/en unknown
- 2003-11-20 IS IS7046A patent/IS7046A/is unknown
- 2003-11-21 EC EC2003004860A patent/ECSP034860A/es unknown
- 2003-11-21 NO NO20035183A patent/NO20035183D0/no not_active Application Discontinuation
- 2003-12-22 BG BG108490A patent/BG108490A/bg unknown
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2007
- 2007-05-17 US US11/749,840 patent/US20080107608A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL158958A0 (en) | 2004-05-12 |
| MXPA03010692A (es) | 2004-07-01 |
| JP2004531570A (ja) | 2004-10-14 |
| KR20040015716A (ko) | 2004-02-19 |
| WO2002096421A1 (en) | 2002-12-05 |
| TNSN03119A1 (en) | 2005-12-23 |
| HRP20031056A2 (en) | 2005-08-31 |
| RU2003134010A (ru) | 2005-05-20 |
| US20030152520A1 (en) | 2003-08-14 |
| HUP0400316A2 (hu) | 2005-02-28 |
| NO20035183D0 (no) | 2003-11-21 |
| BG108490A (bg) | 2005-01-31 |
| US7223778B2 (en) | 2007-05-29 |
| PL367153A1 (en) | 2005-02-21 |
| EP1392302A1 (en) | 2004-03-03 |
| BR0209920A (pt) | 2004-03-30 |
| US20080107608A1 (en) | 2008-05-08 |
| IS7046A (is) | 2003-11-20 |
| AP2003002920A0 (en) | 2003-12-31 |
| CA2448198A1 (en) | 2002-12-05 |
| ECSP034860A (es) | 2004-01-28 |
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