DD205904A5 - Verfahren zur herstellung von imidazo (4,5-c) pyridin-derivaten - Google Patents
Verfahren zur herstellung von imidazo (4,5-c) pyridin-derivaten Download PDFInfo
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- DD205904A5 DD205904A5 DD82244689A DD24468982A DD205904A5 DD 205904 A5 DD205904 A5 DD 205904A5 DD 82244689 A DD82244689 A DD 82244689A DD 24468982 A DD24468982 A DD 24468982A DD 205904 A5 DD205904 A5 DD 205904A5
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- radical
- general formula
- amino
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- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical class C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 32
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 167
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 69
- -1 piperazino group Chemical group 0.000 claims description 69
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 34
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 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
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 235000021190 leftovers Nutrition 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 25
- GPVDHNVGGIAOQT-UHFFFAOYSA-N 2,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 abstract description 8
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 abstract description 7
- 229960004012 amifampridine Drugs 0.000 abstract description 7
- 239000004480 active ingredient Substances 0.000 abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 5
- JZRYRVREPVLNEP-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC2=CC=NC=C2N1 JZRYRVREPVLNEP-UHFFFAOYSA-N 0.000 abstract 1
- 208000020446 Cardiac disease Diseases 0.000 abstract 1
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- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- 239000000243 solution Substances 0.000 description 28
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000007792 addition Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
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- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 4
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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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 4
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- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8133942 | 1981-11-10 | ||
| GB8133930 | 1981-11-10 | ||
| GB8213846 | 1982-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD205904A5 true DD205904A5 (de) | 1984-01-11 |
Family
ID=27261362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82244689A DD205904A5 (de) | 1981-11-10 | 1982-11-09 | Verfahren zur herstellung von imidazo (4,5-c) pyridin-derivaten |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4603139A (cs) |
| EP (1) | EP0079083B1 (cs) |
| KR (1) | KR890000022B1 (cs) |
| AR (1) | AR241247A1 (cs) |
| AU (1) | AU9030682A (cs) |
| DD (1) | DD205904A5 (cs) |
| DK (1) | DK161325C (cs) |
| ES (2) | ES517193A0 (cs) |
| FI (1) | FI79312C (cs) |
| GB (1) | GB2113675B (cs) |
| GR (1) | GR76746B (cs) |
| IE (1) | IE56478B1 (cs) |
| IL (1) | IL67206A0 (cs) |
| MC (1) | MC1491A1 (cs) |
| NO (1) | NO158100C (cs) |
| PH (1) | PH22764A (cs) |
| PT (1) | PT75820B (cs) |
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0072926B1 (de) * | 1981-08-19 | 1986-09-24 | MERCK PATENT GmbH | 2-Aryl-imidazopyridine |
| US4904785A (en) * | 1982-05-03 | 1990-02-27 | Eli Lilly And Company | 2-phenylimidazo[4,5-c]pyridines |
| US4758574A (en) * | 1982-05-03 | 1988-07-19 | Eli Lilly And Company | 2-phenylimidazio (4,5-c) pyridines |
| ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| DE3324115A1 (de) * | 1983-07-05 | 1985-01-17 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| US4515796A (en) * | 1983-09-08 | 1985-05-07 | Eli Lilly And Company | Certain naphthalenyl imidazo compounds and their pharmaceutical use |
| US4533734A (en) * | 1983-11-10 | 1985-08-06 | Eli Lilly And Company | Inotropic agents |
| DE3346602A1 (de) * | 1983-12-23 | 1985-07-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazo(4,5-c)pyridin-one, deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3347290A1 (de) * | 1983-12-28 | 1985-07-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-phenyl-imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| ZA851236B (en) * | 1984-02-24 | 1986-09-24 | Lilly Co Eli | 2-arylimidazo 4,5-cpyridines |
| US4578387A (en) * | 1984-03-05 | 1986-03-25 | Eli Lilly And Company | Inotropic agents |
| DE3445299A1 (de) * | 1984-12-12 | 1986-06-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| IL78241A0 (en) * | 1985-03-29 | 1986-07-31 | Lilly Co Eli | Synthesis of inotropic imidazo(4,5-c)pyridine |
| DE3522230A1 (de) * | 1985-06-21 | 1987-01-02 | Thomae Gmbh Dr K | Neue 2-arylimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US4740599A (en) * | 1986-10-03 | 1988-04-26 | Eli Lilly And Company | Synthesis of alkylsulfinyl substituted 2-phenylimidazo(4,5-c)pyridines |
| ZA889365B (en) * | 1987-12-22 | 1990-08-29 | Lilly Co Eli | Hydrates of andinotropic agent |
| GB8822170D0 (en) * | 1988-09-21 | 1988-10-26 | Pfizer Ltd | Therapeutic agents |
| DE69104481T2 (de) * | 1990-05-09 | 1995-02-09 | Pfizer | Imidazo[4,5-c]pyridine als paf antagonisten. |
| DE4324580A1 (de) * | 1993-07-22 | 1995-01-26 | Thomae Gmbh Dr K | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE69717277T2 (de) * | 1996-05-15 | 2003-09-18 | Altana Pharma Ag | Imidazopyridine |
| WO1998021209A1 (de) * | 1996-11-11 | 1998-05-22 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Neue imidazo- und oxazolopyridine |
| JP2004503553A (ja) * | 2000-06-14 | 2004-02-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | ６，５−縮合二環式複素環 |
| AU2004215664A1 (en) * | 2003-02-25 | 2004-09-10 | Altana Pharma Ag | Imidazo[4,5-b]quinoline-derivatives and their use as no-synthase inhibitors |
| KR20060087386A (ko) * | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
| WO2007034277A1 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Aryl substituted imidazo [4,5-c] pyridine compounds as c3a receptor antagonists |
| CN102271515B (zh) | 2008-10-31 | 2014-07-02 | 健泰科生物技术公司 | 吡唑并嘧啶jak抑制剂化合物和方法 |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| CN105037355B (zh) * | 2009-08-10 | 2017-06-06 | 萨穆梅德有限公司 | Wnt信号传导途径的吲唑抑制剂及其治疗用途 |
| JP5822844B2 (ja) | 2009-12-21 | 2015-11-24 | サミュメッド リミテッド ライアビリティ カンパニー | １Ｈ−ピラゾロ［３，４−ｂ］ピリジンおよびその治療的使用 |
| EP2547338A2 (en) * | 2010-03-17 | 2013-01-23 | F. Hoffmann-La Roche AG | Imidazopyridine compounds, compositions and methods of use |
| EP2616072A1 (en) | 2010-09-15 | 2013-07-24 | F.Hoffmann-La Roche Ag | Azabenzothiazole compounds, compositions and methods of use |
| JP2013542966A (ja) | 2010-11-19 | 2013-11-28 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾロピリジンならびにｔｙｋ２阻害剤としてのピラゾロピリジン及びそれらの使用 |
| RU2627693C2 (ru) | 2011-09-14 | 2017-08-10 | СЭМЬЮМЕД, ЭлЭлСи | ИНДАЗОЛ-3-КАРБОКСАМИДЫ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ СИГНАЛЬНОГО ПУТИ WNT/b-КАТЕНИНА |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| ME03573B (me) | 2012-05-04 | 2020-07-20 | Samumed Llc | 1H-PIRAZOLO[3,4-B]PIRIDINI l NJIHOVA TERAPEUTSKA UPOTREBA |
| US9908867B2 (en) | 2013-01-08 | 2018-03-06 | Samumed, Llc | 3-(benzoimidazol-2-yl)-indazole inhibitors of the Wnt signaling pathway and therapeutic uses thereof |
| EP2818472A1 (en) * | 2013-06-27 | 2014-12-31 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Imidazo[4,5-c]pyridine and pyrrolo[3,2-c]pyridine compounds as G-protein-coupled receptor kinase 5 (GRK5) modulators |
| US11229208B2 (en) | 2013-07-02 | 2022-01-25 | Syngenta Participations Ag | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
| CN107652292B (zh) * | 2013-07-02 | 2020-11-17 | 先正达参股股份有限公司 | 有杀有害生物活性的具有含硫取代基的二环或三环杂环 |
| CA2917262A1 (en) * | 2013-07-02 | 2015-01-08 | Syngenta Participations Ag | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
| KR102362756B1 (ko) * | 2014-02-17 | 2022-02-11 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 2-(헤트)아릴-치환된 융합 비사이클릭 헤테로사이클 유도체 |
| AU2015261812B2 (en) | 2014-05-23 | 2019-11-21 | F. Hoffmann-La Roche Ag | 5-chloro-2-difluoromethoxyphenyl pyrazolopyrimidine compounds which are JAK inhibitors |
| US10081641B2 (en) | 2014-08-21 | 2018-09-25 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016058928A1 (en) * | 2014-10-14 | 2016-04-21 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| EP3233851B1 (en) * | 2014-12-17 | 2020-05-27 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| JP6704397B2 (ja) * | 2014-12-31 | 2020-06-03 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な多環式誘導体 |
| UY36547A (es) * | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| WO2017024025A1 (en) | 2015-08-03 | 2017-02-09 | Sunil Kumar Kc | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10329309B2 (en) | 2015-08-03 | 2019-06-25 | Samumed, Llc | 3-(3H-imidazo[4,5-B]pyridin-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017024004A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10188634B2 (en) | 2015-08-03 | 2019-01-29 | Samumed, Llc | 3-(3H-imidazo[4,5-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017023989A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10463651B2 (en) | 2015-08-03 | 2019-11-05 | Samumed, Llc | 3-(1H-pyrrolo[3,2-C]pyridin-2-YL)-1H-indazoles and therapeutic uses thereof |
| WO2017023972A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10226453B2 (en) | 2015-08-03 | 2019-03-12 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017023996A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| WO2017023984A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| US10166218B2 (en) | 2015-08-03 | 2019-01-01 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| US10285982B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| US10350199B2 (en) | 2015-08-03 | 2019-07-16 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| WO2017023975A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| US10604512B2 (en) | 2015-08-03 | 2020-03-31 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-indazoles and therapeutic uses thereof |
| WO2017023987A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| WO2017024003A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10899757B2 (en) | 2015-11-06 | 2021-01-26 | Samumed, Llc | 2-(1H-indazol-3-yl)-3H-imidazo[4,5-C]pyridines and their anti-inflammatory uses thereof |
| JP7010851B2 (ja) | 2016-06-01 | 2022-02-10 | バイオスプライス セラピューティクス インコーポレイテッド | Ｎ－（５－（３－（７－（３－フルオロフェニル）－３Ｈ－イミダゾ［４，５－ｃ］ピリジン－２－イル）－１Ｈ－インダゾール－５－イル）ピリジン－３－イル）－３－メチルブタンアミドを調製するための方法 |
| BR112019008061A2 (pt) | 2016-10-21 | 2019-09-17 | Samumed Llc | métodos de uso de indazol-3-carboxamidas e seu uso como inibidores da via de sinalização de wnt/b-catenina |
| MA46696A (fr) | 2016-11-07 | 2019-09-11 | Samumed Llc | Formulations injectables à dose unique prêtes à l'emploi |
| CR20190520A (es) | 2017-05-22 | 2020-01-21 | Hoffmann La Roche | Composiciones y compuestos terapéuticos y métodos para utilizarlos |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA820316A (en) * | 1969-08-12 | Fisons Pest Control Limited | Substituted heterocyclic compounds | |
| FI58126C (fi) * | 1973-02-03 | 1980-12-10 | Thomae Gmbh Dr K | Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner |
| US3985891A (en) * | 1973-02-03 | 1976-10-12 | Boehringer Ingelheim Gmbh | 2-Phenyl-imidazo (4,5-b)pyridines and salts thereof |
| US3891660A (en) * | 1974-02-07 | 1975-06-24 | Squibb & Sons Inc | Derivatives of 1H-imidazo{8 4,5-c{9 pyridine-7-carboxylic acids and esters |
| SU566842A1 (ru) * | 1976-01-06 | 1977-07-30 | Донецкое Отделение Физико-Органической Химии Института Физической Химии Им.Л.В.Писаржевского Ан Украинской Сср | Способ получени замещенных имидазопиридинов |
| US4281005A (en) * | 1979-03-05 | 1981-07-28 | Merck & Co., Inc. | Novel 2-pyridylimidazole compounds |
| DE2927987A1 (de) * | 1979-07-11 | 1981-02-05 | Thomae Gmbh Dr K | Neue 2-alkoxyphenyl-imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine, deren herstellung und deren verwendung als arzneimittel |
| DE3037464A1 (de) * | 1980-10-03 | 1982-05-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | 6-hydroxy-2-phenyl-imidazo 4,5-b zu pyridine, ihre herstellung und diese sie enthaltende arzneimittel |
| EP0072926B1 (de) * | 1981-08-19 | 1986-09-24 | MERCK PATENT GmbH | 2-Aryl-imidazopyridine |
| ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
-
1982
- 1982-11-08 ES ES517193A patent/ES517193A0/es active Granted
- 1982-11-09 FI FI823846A patent/FI79312C/fi not_active IP Right Cessation
- 1982-11-09 GB GB08231984A patent/GB2113675B/en not_active Expired
- 1982-11-09 PT PT75820A patent/PT75820B/pt unknown
- 1982-11-09 AR AR82291240A patent/AR241247A1/es active
- 1982-11-09 MC MC821611A patent/MC1491A1/xx unknown
- 1982-11-09 DD DD82244689A patent/DD205904A5/de not_active IP Right Cessation
- 1982-11-09 AU AU90306/82A patent/AU9030682A/en not_active Abandoned
- 1982-11-09 NO NO823732A patent/NO158100C/no unknown
- 1982-11-09 DK DK499582A patent/DK161325C/da not_active IP Right Cessation
- 1982-11-09 EP EP82110328A patent/EP0079083B1/en not_active Expired - Lifetime
- 1982-11-09 GR GR69767A patent/GR76746B/el unknown
- 1982-11-09 IE IE2667/82A patent/IE56478B1/en not_active IP Right Cessation
- 1982-11-09 PH PH28109A patent/PH22764A/en unknown
- 1982-11-09 KR KR8205055A patent/KR890000022B1/ko not_active Expired
- 1982-11-09 IL IL67206A patent/IL67206A0/xx unknown
-
1983
- 1983-06-08 ES ES523083A patent/ES523083A0/es active Granted
-
1985
- 1985-01-11 US US06/690,815 patent/US4603139A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL67206A0 (en) | 1983-03-31 |
| EP0079083A1 (en) | 1983-05-18 |
| ES8401486A1 (es) | 1983-12-01 |
| KR840002398A (ko) | 1984-07-02 |
| PT75820B (en) | 1986-06-11 |
| US4603139A (en) | 1986-07-29 |
| AR241247A1 (es) | 1992-03-31 |
| PT75820A (en) | 1982-12-01 |
| PH22764A (en) | 1988-12-12 |
| FI823846L (fi) | 1983-05-11 |
| IE56478B1 (en) | 1991-08-14 |
| NO823732L (no) | 1983-05-11 |
| GB2113675A (en) | 1983-08-10 |
| ES8503351A1 (es) | 1985-02-16 |
| KR890000022B1 (ko) | 1989-03-06 |
| EP0079083B1 (en) | 1991-02-27 |
| ES517193A0 (es) | 1983-12-01 |
| IE822667L (en) | 1983-05-10 |
| NO158100C (no) | 1988-07-13 |
| NO158100B (no) | 1988-04-05 |
| ES523083A0 (es) | 1985-02-16 |
| DK161325B (da) | 1991-06-24 |
| DK161325C (da) | 1991-12-02 |
| FI79312C (fi) | 1989-12-11 |
| DK499582A (da) | 1983-05-11 |
| FI823846A0 (fi) | 1982-11-09 |
| MC1491A1 (fr) | 1983-09-12 |
| AU9030682A (en) | 1983-05-19 |
| GB2113675B (en) | 1985-10-30 |
| GR76746B (cs) | 1984-08-30 |
| FI79312B (fi) | 1989-08-31 |
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