KR880006237A - 이미다조 피리딘 화합물 및 그것의 제조방법 - Google Patents
이미다조 피리딘 화합물 및 그것의 제조방법 Download PDFInfo
- Publication number
- KR880006237A KR880006237A KR1019870013343A KR870013343A KR880006237A KR 880006237 A KR880006237 A KR 880006237A KR 1019870013343 A KR1019870013343 A KR 1019870013343A KR 870013343 A KR870013343 A KR 870013343A KR 880006237 A KR880006237 A KR 880006237A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- hydroxy
- amino
- methylbenzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- -1 Imidazo pyridine compound Chemical class 0.000 title claims 76
- 238000002360 preparation method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 19
- 125000003282 alkyl amino group Chemical group 0.000 claims 18
- 125000005236 alkanoylamino group Chemical group 0.000 claims 14
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- 208000025865 Ulcer Diseases 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005281 alkyl ureido group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- 231100000397 ulcer Toxicity 0.000 claims 2
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- ZTXAFIRXXMEEGM-UHFFFAOYSA-N [3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]thiourea Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1NC(N)=S ZTXAFIRXXMEEGM-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000006319 alkynyl amino group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 150000005232 imidazopyridines Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB86628262 | 1986-11-26 | ||
| GB868628262A GB8628262D0 (en) | 1986-11-26 | 1986-11-26 | Imidazopyridine compounds |
| GB878723439A GB8723439D0 (en) | 1987-10-06 | 1987-10-06 | Imidazopyridine compounds |
| GB8723439 | 1987-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR880006237A true KR880006237A (ko) | 1988-07-22 |
Family
ID=26291587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870013343A Ceased KR880006237A (ko) | 1986-11-26 | 1987-11-25 | 이미다조 피리딘 화합물 및 그것의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4831041A (https=) |
| EP (1) | EP0268989B1 (https=) |
| KR (1) | KR880006237A (https=) |
| CN (1) | CN87108027A (https=) |
| AU (1) | AU8169387A (https=) |
| DE (1) | DE3780263T2 (https=) |
| DK (1) | DK608887A (https=) |
| ES (1) | ES2064310T3 (https=) |
| FI (1) | FI875157A7 (https=) |
| GR (1) | GR3005685T3 (https=) |
| HU (1) | HUT45526A (https=) |
| IL (1) | IL84522A0 (https=) |
| NO (1) | NO874904L (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| US4791117A (en) * | 1986-09-22 | 1988-12-13 | Ortho Pharmaceutical Corporation | 2- or 3-aryl substituted imidazo[1,2-a]pyridines and their use as calcium channel blockers |
| WO1989000570A1 (fr) * | 1987-07-16 | 1989-01-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Nouveaux diazoles |
| GB8722488D0 (en) * | 1987-09-24 | 1987-10-28 | Fujisawa Pharmaceutical Co | Imidazopyridine compound |
| US5244908A (en) * | 1990-07-30 | 1993-09-14 | Takeda Chemical Industries, Ltd. | Imidazopyridine derivatives and their pharmaceutical use |
| MY110439A (en) * | 1991-02-07 | 1998-05-30 | Ishihara Sangyo Kaisha | N-phenylcarbamate compound, process for preparing the same and biocidal composition for control of harmful organisms |
| GB9201693D0 (en) * | 1992-01-27 | 1992-03-11 | Smithkline Beecham Intercredit | Compounds |
| US5574042A (en) * | 1992-11-02 | 1996-11-12 | Fujisawa Pharmaceutical Co., Ltd | Imidazo [1,2-a] pyridines and their pharmaceutical use |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| UA48122C2 (uk) * | 1993-10-11 | 2002-08-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ |
| AU3221795A (en) * | 1994-07-28 | 1996-02-22 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Halogenated imidazopyridines |
| JPH10505331A (ja) * | 1994-07-28 | 1998-05-26 | ビイク グルデン ロンベルク ヒェーミッシェ ファブリーク ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンジルイミダゾピリジン |
| WO1996003405A1 (de) * | 1994-07-28 | 1996-02-08 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Imidazopyridin-azolidinone |
| US6096758A (en) * | 1996-01-26 | 2000-08-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | 3-methylimidazopyridines |
| AU1545297A (en) * | 1996-01-26 | 1997-08-20 | Byk Gulden | Imidazopyridine halides |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| DE10145457A1 (de) | 2001-09-14 | 2003-04-03 | Basf Ag | Substituierte Imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-one, Verfahren zu ihrer Herstellung, sowie deren Verwendung zur Herstellung von Imidazo[1,2,-a]pyridinen |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| ES2335498T3 (es) | 2003-03-10 | 2010-03-29 | Nycomed Gmbh | Nuevo proceso para la preparacion de reflumilast. |
| US8663694B2 (en) * | 2005-03-16 | 2014-03-04 | Takeda Gmbh | Taste masked dosage form containing roflumilast |
| WO2013102142A1 (en) * | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted benzaldehyde compounds and methods for their use in increasing tissue oxygenation |
| HK1203412A1 (en) | 2011-12-28 | 2015-10-30 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| WO2014145040A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| EP3919056B1 (en) | 2013-03-15 | 2024-08-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| AP2015008718A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| SG10201802911RA (en) | 2013-03-15 | 2018-05-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| ES2860648T5 (es) | 2014-02-07 | 2024-11-27 | Global Blood Therapeutics Inc | Polimorfos cristalinos de la base libre de 2-hidroxi-6-((2-(1-isopropil-1H-pirazol-5-il)piridin-3-il)metoxi)benzaldehído |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| US11020382B2 (en) | 2015-12-04 | 2021-06-01 | Global Blood Therapeutics, Inc. | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| TWI825524B (zh) | 2016-05-12 | 2023-12-11 | 美商全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| EP3860975B1 (en) | 2018-10-01 | 2023-10-18 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin for the treatment of sickle cell disease |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| DE3269604D1 (en) * | 1981-06-26 | 1986-04-10 | Schering Corp | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
-
1987
- 1987-11-12 US US07/119,577 patent/US4831041A/en not_active Expired - Fee Related
- 1987-11-18 IL IL84522A patent/IL84522A0/xx unknown
- 1987-11-18 DE DE8787117018T patent/DE3780263T2/de not_active Expired - Lifetime
- 1987-11-18 EP EP87117018A patent/EP0268989B1/en not_active Expired - Lifetime
- 1987-11-18 ES ES87117018T patent/ES2064310T3/es not_active Expired - Lifetime
- 1987-11-19 DK DK608887A patent/DK608887A/da not_active Application Discontinuation
- 1987-11-23 FI FI875157A patent/FI875157A7/fi not_active Application Discontinuation
- 1987-11-25 KR KR1019870013343A patent/KR880006237A/ko not_active Ceased
- 1987-11-25 AU AU81693/87A patent/AU8169387A/en not_active Abandoned
- 1987-11-25 NO NO874904A patent/NO874904L/no unknown
- 1987-11-25 HU HU875302A patent/HUT45526A/hu unknown
- 1987-11-26 CN CN198787108027A patent/CN87108027A/zh active Pending
-
1992
- 1992-09-10 GR GR920402014T patent/GR3005685T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK608887D0 (da) | 1987-11-19 |
| FI875157A0 (fi) | 1987-11-23 |
| DE3780263D1 (de) | 1992-08-13 |
| NO874904D0 (no) | 1987-11-25 |
| NO874904L (no) | 1988-05-27 |
| GR3005685T3 (https=) | 1993-06-07 |
| HUT45526A (en) | 1988-07-28 |
| FI875157A7 (fi) | 1988-05-27 |
| IL84522A0 (en) | 1988-04-29 |
| EP0268989B1 (en) | 1992-07-08 |
| DE3780263T2 (de) | 1992-12-24 |
| CN87108027A (zh) | 1988-06-08 |
| US4831041A (en) | 1989-05-16 |
| DK608887A (da) | 1988-05-27 |
| EP0268989A1 (en) | 1988-06-01 |
| AU8169387A (en) | 1988-06-02 |
| ES2064310T3 (es) | 1995-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19871125 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19921124 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19871125 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19950913 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 19951123 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19950913 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |