SK4222001A3 - 2,3-disubstituted pyridine derivatives, process for the preparation thereof, drug compositions containing the same and intermediates for the preparation - Google Patents
2,3-disubstituted pyridine derivatives, process for the preparation thereof, drug compositions containing the same and intermediates for the preparation Download PDFInfo
- Publication number
- SK4222001A3 SK4222001A3 SK422-2001A SK4222001A SK4222001A3 SK 4222001 A3 SK4222001 A3 SK 4222001A3 SK 4222001 A SK4222001 A SK 4222001A SK 4222001 A3 SK4222001 A3 SK 4222001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkoxy
- lower alkoxy
- hydroxy
- group
- substituted
- Prior art date
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- -1 2,3-disubstituted pyridine Chemical class 0.000 title claims abstract description 92
- 238000002360 preparation method Methods 0.000 title claims description 96
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title description 152
- 239000000543 intermediate Substances 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 3
- 229940079593 drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 234
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 80
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 126
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 238000001727 in vivo Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- HBUJRYNMNPGQOW-UHFFFAOYSA-N 4-[3-[2-(3-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol Chemical compound OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(Cl)=C1 HBUJRYNMNPGQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- GJSPSEKVJTVWFV-UHFFFAOYSA-N 4-[3-(2-phenoxypyridin-3-yl)oxypropyl]pyridin-3-ol Chemical compound OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC=C1 GJSPSEKVJTVWFV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- RMABIHKKIBQPNG-UHFFFAOYSA-N 4-[3-[2-(3-bromophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol Chemical compound OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(Br)=C1 RMABIHKKIBQPNG-UHFFFAOYSA-N 0.000 claims description 4
- WDEZWJJTQGXGFY-UHFFFAOYSA-N 4-[3-[2-(3-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-amine Chemical compound NC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(Cl)=C1 WDEZWJJTQGXGFY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- QIVHHCJJHFTPSP-UHFFFAOYSA-N 2-(3-bromophenoxy)-3-(3-pyridin-4-ylpropoxy)pyridine Chemical compound BrC1=CC=CC(OC=2C(=CC=CN=2)OCCCC=2C=CN=CC=2)=C1 QIVHHCJJHFTPSP-UHFFFAOYSA-N 0.000 claims description 3
- GQJVWPSNLAAUFU-UHFFFAOYSA-N 4-[3-[2-(3-fluorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol Chemical compound OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(F)=C1 GQJVWPSNLAAUFU-UHFFFAOYSA-N 0.000 claims description 3
- PLONSVKESYYAAQ-UHFFFAOYSA-N 5-[3-[2-(3-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol Chemical compound OC1=CN=CC(CCCOC=2C(=NC=CC=2)OC=2C=C(Cl)C=CC=2)=C1 PLONSVKESYYAAQ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QNEXNWAIFXYIOW-UHFFFAOYSA-N [4-[3-(2-phenoxypyridin-3-yl)oxypropyl]pyridin-3-yl] acetate Chemical compound CC(=O)OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC=C1 QNEXNWAIFXYIOW-UHFFFAOYSA-N 0.000 claims description 3
- RWPGUGSPZYYCHG-UHFFFAOYSA-N [4-[3-[2-(3-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-yl] acetate Chemical compound CC(=O)OC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(Cl)=C1 RWPGUGSPZYYCHG-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001231 benzoyloxy group Chemical class C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
- DJRQXWXGDSACDB-UHFFFAOYSA-N n-[4-[3-[2-(3-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CN=CC=C1CCCOC1=CC=CN=C1OC1=CC=CC(Cl)=C1 DJRQXWXGDSACDB-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 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 3
- AXQKEDLOTKRDKL-UHFFFAOYSA-N 2-(3-bromophenyl)sulfanyl-3-(3-pyridin-4-ylpropoxy)pyridine Chemical compound BrC1=CC=CC(SC=2C(=CC=CN=2)OCCCC=2C=CN=CC=2)=C1 AXQKEDLOTKRDKL-UHFFFAOYSA-N 0.000 claims description 2
- OQBJLRBPMSGVRP-UHFFFAOYSA-N 2-(3-fluorophenoxy)-3-(3-pyridin-4-ylpropoxy)pyridine Chemical compound FC1=CC=CC(OC=2C(=CC=CN=2)OCCCC=2C=CN=CC=2)=C1 OQBJLRBPMSGVRP-UHFFFAOYSA-N 0.000 claims description 2
- XQGFGZZLPODOBN-UHFFFAOYSA-N 2-phenoxy-3-(3-pyridin-4-ylpropoxy)pyridine Chemical compound C=1C=NC=CC=1CCCOC1=CC=CN=C1OC1=CC=CC=C1 XQGFGZZLPODOBN-UHFFFAOYSA-N 0.000 claims description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 21
- 238000011282 treatment Methods 0.000 abstract description 8
- 238000011321 prophylaxis Methods 0.000 abstract description 5
- 208000006673 asthma Diseases 0.000 abstract description 4
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- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 208000000884 Airway Obstruction Diseases 0.000 abstract description 2
- 208000019693 Lung disease Diseases 0.000 abstract description 2
- 230000000172 allergic effect Effects 0.000 abstract description 2
- 208000010668 atopic eczema Diseases 0.000 abstract description 2
- 230000003182 bronchodilatating effect Effects 0.000 abstract description 2
- 210000000056 organ Anatomy 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 342
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 156
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
- 239000000243 solution Substances 0.000 description 109
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
- 238000006243 chemical reaction Methods 0.000 description 99
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 72
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 69
- 239000003480 eluent Substances 0.000 description 62
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 238000010898 silica gel chromatography Methods 0.000 description 42
- 239000013078 crystal Substances 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 239000012044 organic layer Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
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- 238000001816 cooling Methods 0.000 description 32
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 238000010992 reflux Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 24
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
- 235000017557 sodium bicarbonate Nutrition 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
- 238000004440 column chromatography Methods 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
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- 239000007858 starting material Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
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- 125000001246 bromo group Chemical group Br* 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 9
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- NBWRPZAIDQVHMS-UHFFFAOYSA-N ethyl 3-(3,5-dimethoxypyridin-4-yl)propanoate Chemical compound CCOC(=O)CCC1=C(OC)C=NC=C1OC NBWRPZAIDQVHMS-UHFFFAOYSA-N 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 239000002184 metal Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
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- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- 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
-
- 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
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D213/70—Sulfur atoms
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- 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
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
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- 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
- C07D213/73—Unsubstituted amino or imino radicals
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28384898 | 1998-10-06 | ||
PCT/JP1999/005385 WO2000020391A1 (fr) | 1998-10-06 | 1999-09-30 | Derives pyridine disubstitues en position 2,3, procede de preparation associe, compositions de medicament contenant ces derives, et intermediaires servant dans cette preparation |
Publications (1)
Publication Number | Publication Date |
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SK4222001A3 true SK4222001A3 (en) | 2001-10-08 |
Family
ID=17670959
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK422-2001A SK4222001A3 (en) | 1998-10-06 | 1999-09-30 | 2,3-disubstituted pyridine derivatives, process for the preparation thereof, drug compositions containing the same and intermediates for the preparation |
Country Status (20)
Country | Link |
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US (3) | US6555557B1 (fr) |
EP (1) | EP1120409B1 (fr) |
KR (1) | KR20010085852A (fr) |
CN (1) | CN1173950C (fr) |
AT (1) | ATE287875T1 (fr) |
AU (1) | AU754253B2 (fr) |
BR (1) | BR9914091A (fr) |
CA (1) | CA2345577A1 (fr) |
DE (1) | DE69923467D1 (fr) |
HU (1) | HUP0104026A3 (fr) |
ID (1) | ID27509A (fr) |
IL (1) | IL141992A0 (fr) |
NO (1) | NO20011722L (fr) |
NZ (1) | NZ510719A (fr) |
PL (1) | PL347109A1 (fr) |
RU (1) | RU2235095C2 (fr) |
SK (1) | SK4222001A3 (fr) |
TR (1) | TR200101028T2 (fr) |
WO (1) | WO2000020391A1 (fr) |
ZA (1) | ZA200102067B (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1368345B1 (fr) * | 2001-03-02 | 2006-03-22 | F. Hoffmann-La Roche AG | Derives d'acide alcoxycarbonylaminoheteroaryle carboxylique en tant qu'antagonistes d'ip |
JP2006021996A (ja) * | 2002-07-04 | 2006-01-26 | Dainippon Sumitomo Pharma Co Ltd | 置換ヒドロキシピリジン化合物の抱合体 |
US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
US7550499B2 (en) | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
WO2006075748A1 (fr) * | 2005-01-17 | 2006-07-20 | Santen Pharmaceutical Co., Ltd. | Agent therapeutique pour maladie conjonctivale allergique |
US7645778B2 (en) | 2005-01-19 | 2010-01-12 | Bristol-Myers Squibb Company | Heteroaryl compounds as P2Y1 receptor inhibitors |
WO2007002634A1 (fr) * | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Antagonistes carbocycliques et heherocycliques du recepteur p2y1, utiles pour traiter des etats pathologiques thrombotiques |
ES2352796T3 (es) | 2005-06-27 | 2011-02-23 | Bristol-Myers Squibb Company | Antagonistas cíclicos unidos a c del receptor p2y1 útiles en el tratamiento de afecciones trombóticas. |
DE602006020871D1 (de) | 2005-06-27 | 2011-05-05 | Bristol Myers Squibb Co | Lineare harnstoffmimetika-antagonisten des p2y1-rezeptors zur behandlung von thromboseleiden |
AU2006261828A1 (en) | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | N-linked heterocyclic antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
US8309734B2 (en) * | 2008-10-29 | 2012-11-13 | Hoffmann-La Roche Inc. | Substituted pyridines as GPBAR1 agonists |
US8420647B2 (en) * | 2010-01-21 | 2013-04-16 | Hoffmann-La Roche Inc. | 4-phenoxy-nicotinamide or 4-phenoxy-pyrimidine-5-carboxamide compounds |
TR201907092T4 (tr) * | 2012-12-05 | 2019-06-21 | Chiesi Farm Spa | Fosfodiesteraz inhibitörleri olarak 1-fenil-2-piridinil alkil alkol türevleri. |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4193926A (en) | 1974-03-20 | 1980-03-18 | Schering Aktiengesellschaft | 4-(Polyalkoxy phenyl)-2-pyrrolidones |
GB8718940D0 (en) * | 1987-08-11 | 1987-09-16 | Glaxo Group Ltd | Chemical compounds |
IE71647B1 (en) | 1991-01-28 | 1997-02-26 | Rhone Poulenc Rorer Ltd | Benzamide derivatives |
US5552438A (en) | 1992-04-02 | 1996-09-03 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
DE69332762T2 (de) | 1992-12-02 | 2003-08-14 | Pfizer Inc., New York | Cathecoldiether als selektive pde iv hemmungsmittel |
TW257757B (fr) | 1993-03-03 | 1995-09-21 | Boehringer Mannheim Gmbh | |
TW429148B (en) | 1995-10-27 | 2001-04-11 | Pfizer | Pharmaceutical agents for the treatment of acute and chronic inflammatory diseases |
EP0873311A1 (fr) * | 1995-12-15 | 1998-10-28 | Merck Frosst Canada Inc. | Derives d'ethane tri-aryle utilises comme inhibiteurs de pde iv |
EP0971894A1 (fr) | 1997-04-04 | 2000-01-19 | Pfizer Products Inc. | Derives de nicotinamide |
JP4058507B2 (ja) * | 1997-07-10 | 2008-03-12 | 国立大学法人 東京医科歯科大学 | 4,5−ジヒドロ−[1H]−ベンズ[g]インダゾール−3−カルボン酸誘導体 |
-
1999
- 1999-09-30 AT AT99970082T patent/ATE287875T1/de not_active IP Right Cessation
- 1999-09-30 SK SK422-2001A patent/SK4222001A3/sk unknown
- 1999-09-30 PL PL99347109A patent/PL347109A1/xx not_active Application Discontinuation
- 1999-09-30 BR BR9914091-8A patent/BR9914091A/pt not_active IP Right Cessation
- 1999-09-30 DE DE69923467T patent/DE69923467D1/de not_active Expired - Lifetime
- 1999-09-30 KR KR1020017003884A patent/KR20010085852A/ko not_active Application Discontinuation
- 1999-09-30 US US09/787,766 patent/US6555557B1/en not_active Expired - Fee Related
- 1999-09-30 HU HU0104026A patent/HUP0104026A3/hu unknown
- 1999-09-30 IL IL14199299A patent/IL141992A0/xx unknown
- 1999-09-30 ID IDW20010691A patent/ID27509A/id unknown
- 1999-09-30 CA CA002345577A patent/CA2345577A1/fr not_active Abandoned
- 1999-09-30 RU RU2001112110/04A patent/RU2235095C2/ru not_active IP Right Cessation
- 1999-09-30 EP EP99970082A patent/EP1120409B1/fr not_active Expired - Lifetime
- 1999-09-30 NZ NZ510719A patent/NZ510719A/en unknown
- 1999-09-30 AU AU60000/99A patent/AU754253B2/en not_active Ceased
- 1999-09-30 WO PCT/JP1999/005385 patent/WO2000020391A1/fr not_active Application Discontinuation
- 1999-09-30 CN CNB998138479A patent/CN1173950C/zh not_active Expired - Fee Related
- 1999-09-30 TR TR2001/01028T patent/TR200101028T2/xx unknown
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2001
- 2001-03-13 ZA ZA200102067A patent/ZA200102067B/xx unknown
- 2001-04-05 NO NO20011722A patent/NO20011722L/no not_active Application Discontinuation
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2003
- 2003-03-10 US US10/383,585 patent/US6683186B2/en not_active Expired - Fee Related
- 2003-03-10 US US10/383,586 patent/US6765095B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP1120409B1 (fr) | 2005-01-26 |
KR20010085852A (ko) | 2001-09-07 |
US6555557B1 (en) | 2003-04-29 |
NZ510719A (en) | 2003-02-28 |
IL141992A0 (en) | 2002-03-10 |
US20030195232A1 (en) | 2003-10-16 |
PL347109A1 (en) | 2002-03-25 |
CA2345577A1 (fr) | 2000-04-13 |
DE69923467D1 (de) | 2005-03-03 |
BR9914091A (pt) | 2001-11-27 |
CN1173950C (zh) | 2004-11-03 |
US6765095B2 (en) | 2004-07-20 |
TR200101028T2 (tr) | 2001-08-21 |
AU754253B2 (en) | 2002-11-07 |
CN1328547A (zh) | 2001-12-26 |
ATE287875T1 (de) | 2005-02-15 |
WO2000020391A1 (fr) | 2000-04-13 |
HUP0104026A2 (hu) | 2002-03-28 |
NO20011722L (no) | 2001-06-05 |
ID27509A (id) | 2001-04-12 |
ZA200102067B (en) | 2001-10-24 |
EP1120409A4 (fr) | 2002-03-20 |
HUP0104026A3 (en) | 2002-06-28 |
US20030199554A1 (en) | 2003-10-23 |
AU6000099A (en) | 2000-04-26 |
EP1120409A1 (fr) | 2001-08-01 |
US6683186B2 (en) | 2004-01-27 |
NO20011722D0 (no) | 2001-04-05 |
RU2235095C2 (ru) | 2004-08-27 |
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