NO325663B1 - Azabenzimidazolbaserte forbindelser, fremgangsmater for fremstilling av forbindelsene, anvendelse av forbindelsene samt farmasoytiske sammensetninger inneholdende forbindelsene - Google Patents
Azabenzimidazolbaserte forbindelser, fremgangsmater for fremstilling av forbindelsene, anvendelse av forbindelsene samt farmasoytiske sammensetninger inneholdende forbindelsene Download PDFInfo
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- NO325663B1 NO325663B1 NO20001555A NO20001555A NO325663B1 NO 325663 B1 NO325663 B1 NO 325663B1 NO 20001555 A NO20001555 A NO 20001555A NO 20001555 A NO20001555 A NO 20001555A NO 325663 B1 NO325663 B1 NO 325663B1
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- Prior art keywords
- imidazo
- pyridine
- group
- alkyl
- compounds
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- BLVGTOKCEIAUDA-UHFFFAOYSA-N methyl n-[6-(2-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1Cl BLVGTOKCEIAUDA-UHFFFAOYSA-N 0.000 description 1
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- DXHRHXQVGBSZEM-UHFFFAOYSA-N methyl n-[6-(2-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1Cl DXHRHXQVGBSZEM-UHFFFAOYSA-N 0.000 description 1
- GTFTTWFGAUGHEC-UHFFFAOYSA-N methyl n-[6-(2-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1F GTFTTWFGAUGHEC-UHFFFAOYSA-N 0.000 description 1
- JVKZNYHUWAXLIH-UHFFFAOYSA-N methyl n-[6-(2-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1F JVKZNYHUWAXLIH-UHFFFAOYSA-N 0.000 description 1
- QDRVDJCMQMVSHZ-UHFFFAOYSA-N methyl n-[6-(2-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1F QDRVDJCMQMVSHZ-UHFFFAOYSA-N 0.000 description 1
- YYXJQLOOPZZUOP-UHFFFAOYSA-N methyl n-[6-(2-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1OC YYXJQLOOPZZUOP-UHFFFAOYSA-N 0.000 description 1
- JLKYYEQFCFSAHE-UHFFFAOYSA-N methyl n-[6-(2-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1OC JLKYYEQFCFSAHE-UHFFFAOYSA-N 0.000 description 1
- QAGUHLKOQASYRM-UHFFFAOYSA-N methyl n-[6-(2-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1C QAGUHLKOQASYRM-UHFFFAOYSA-N 0.000 description 1
- CGEYSZLFQLBOQJ-UHFFFAOYSA-N methyl n-[6-(2-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1C CGEYSZLFQLBOQJ-UHFFFAOYSA-N 0.000 description 1
- MVDFKSUNQKEZDG-UHFFFAOYSA-N methyl n-[6-(2-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1SC1=CC=CC=C1C MVDFKSUNQKEZDG-UHFFFAOYSA-N 0.000 description 1
- UHPOXMGLKCSMEI-UHFFFAOYSA-N methyl n-[6-(2-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1[N+]([O-])=O UHPOXMGLKCSMEI-UHFFFAOYSA-N 0.000 description 1
- AHQYHAIUJWDGCW-UHFFFAOYSA-N methyl n-[6-(2-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1[N+]([O-])=O AHQYHAIUJWDGCW-UHFFFAOYSA-N 0.000 description 1
- LEFCCEOVCXOZFW-UHFFFAOYSA-N methyl n-[6-(3-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(Cl)=C1 LEFCCEOVCXOZFW-UHFFFAOYSA-N 0.000 description 1
- KPKLDOVGEZXDGY-UHFFFAOYSA-N methyl n-[6-(3-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(Cl)=C1 KPKLDOVGEZXDGY-UHFFFAOYSA-N 0.000 description 1
- XGCVHDXETITBKK-UHFFFAOYSA-N methyl n-[6-(3-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(Cl)=C1 XGCVHDXETITBKK-UHFFFAOYSA-N 0.000 description 1
- UJGVWDDHQMIEHG-UHFFFAOYSA-N methyl n-[6-(3-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(F)=C1 UJGVWDDHQMIEHG-UHFFFAOYSA-N 0.000 description 1
- LTEJAPLVONTXLX-UHFFFAOYSA-N methyl n-[6-(3-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(F)=C1 LTEJAPLVONTXLX-UHFFFAOYSA-N 0.000 description 1
- XXFGWVGPJHLUAA-UHFFFAOYSA-N methyl n-[6-(3-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(F)=C1 XXFGWVGPJHLUAA-UHFFFAOYSA-N 0.000 description 1
- MIRJINYQCNZPPH-UHFFFAOYSA-N methyl n-[6-(3-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(OC)=C1 MIRJINYQCNZPPH-UHFFFAOYSA-N 0.000 description 1
- PCJKQZZRZGJKFN-UHFFFAOYSA-N methyl n-[6-(3-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(OC)=C1 PCJKQZZRZGJKFN-UHFFFAOYSA-N 0.000 description 1
- XEJDQGSVVYABQK-UHFFFAOYSA-N methyl n-[6-(3-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(OC)=C1 XEJDQGSVVYABQK-UHFFFAOYSA-N 0.000 description 1
- GJGRCSBQWUGOSD-UHFFFAOYSA-N methyl n-[6-(3-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(C)=C1 GJGRCSBQWUGOSD-UHFFFAOYSA-N 0.000 description 1
- MHOKSXDPQKGZGI-UHFFFAOYSA-N methyl n-[6-(3-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(C)=C1 MHOKSXDPQKGZGI-UHFFFAOYSA-N 0.000 description 1
- NCRPWNBUYGEHHP-UHFFFAOYSA-N methyl n-[6-(3-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC([N+]([O-])=O)=C1 NCRPWNBUYGEHHP-UHFFFAOYSA-N 0.000 description 1
- PWFAVHFFLZRGQN-UHFFFAOYSA-N methyl n-[6-(3-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC([N+]([O-])=O)=C1 PWFAVHFFLZRGQN-UHFFFAOYSA-N 0.000 description 1
- YPVOGSUISPYBCN-UHFFFAOYSA-N methyl n-[6-(4-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(Cl)C=C1 YPVOGSUISPYBCN-UHFFFAOYSA-N 0.000 description 1
- CZWTULUSEUKILH-UHFFFAOYSA-N methyl n-[6-(4-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(Cl)C=C1 CZWTULUSEUKILH-UHFFFAOYSA-N 0.000 description 1
- OYSANANHGSOVFE-UHFFFAOYSA-N methyl n-[6-(4-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(Cl)C=C1 OYSANANHGSOVFE-UHFFFAOYSA-N 0.000 description 1
- SFFIYVRUXFJDCB-UHFFFAOYSA-N methyl n-[6-(4-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1NC1=CC=C(F)C=C1 SFFIYVRUXFJDCB-UHFFFAOYSA-N 0.000 description 1
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- UYPXRHKDZQBFIZ-UHFFFAOYSA-N methyl n-[6-(4-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(OC)C=C1 UYPXRHKDZQBFIZ-UHFFFAOYSA-N 0.000 description 1
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- 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
Landscapes
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- Medicinal Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6014597P | 1997-09-26 | 1997-09-26 | |
| PCT/US1998/019973 WO1999016438A1 (en) | 1997-09-26 | 1998-09-23 | Azabenzimidazole-based compounds for modulating serine/threonine protein kinase function |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20001555L NO20001555L (no) | 2000-03-24 |
| NO20001555D0 NO20001555D0 (no) | 2000-03-24 |
| NO325663B1 true NO325663B1 (no) | 2008-07-07 |
Family
ID=22027657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20001555A NO325663B1 (no) | 1997-09-26 | 2000-03-24 | Azabenzimidazolbaserte forbindelser, fremgangsmater for fremstilling av forbindelsene, anvendelse av forbindelsene samt farmasoytiske sammensetninger inneholdende forbindelsene |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6093728A (pt) |
| EP (1) | EP1017384B1 (pt) |
| JP (1) | JP2001517699A (pt) |
| KR (1) | KR100547929B1 (pt) |
| CN (1) | CN1167420C (pt) |
| AR (1) | AR017266A1 (pt) |
| AT (1) | ATE281834T1 (pt) |
| AU (1) | AU748849B2 (pt) |
| BG (1) | BG64784B1 (pt) |
| BR (1) | BR9812682A (pt) |
| CA (1) | CA2305370C (pt) |
| DE (1) | DE69827516T2 (pt) |
| DK (1) | DK1017384T3 (pt) |
| ES (1) | ES2230719T3 (pt) |
| HK (1) | HK1032206A1 (pt) |
| HU (1) | HUP0004024A3 (pt) |
| IL (4) | IL135109A0 (pt) |
| NO (1) | NO325663B1 (pt) |
| NZ (2) | NZ503432A (pt) |
| PL (1) | PL191618B1 (pt) |
| PT (1) | PT1017384E (pt) |
| RU (1) | RU2230553C2 (pt) |
| SK (1) | SK285357B6 (pt) |
| TR (1) | TR200001546T2 (pt) |
| TW (1) | TW581815B (pt) |
| UA (1) | UA72448C2 (pt) |
| WO (1) | WO1999016438A1 (pt) |
| ZA (1) | ZA988797B (pt) |
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| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
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| EP3659599B1 (en) | 2011-10-19 | 2022-12-21 | Signal Pharmaceuticals, LLC | 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one for use in the treatment of glioblastoma multiforme |
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| CN107474051B (zh) | 2013-05-29 | 2020-10-30 | 西格诺药品有限公司 | 二氢吡嗪并吡嗪化合物的药物组合物、其固体形式和它们的用途 |
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| WO2015160882A1 (en) | 2014-04-16 | 2015-10-22 | Signal Pharmaceuticals, Llc | SOLID FORMS COMPRISING 7-(6-(2-HYDROXYPROPAN-2YL) PYRIDIN-3-YL)-1-(TRANS)-4-METHOXYCYCLOHEXYL)-3, 4-DIHYDROPYRAZINO[2,3-b] PYRAZIN-2(1H)-ONE, AND A COFORMER, COMPOSITIONS AND METHODS OF USE THEREOF |
| KR20170024120A (ko) | 2014-07-14 | 2017-03-06 | 시그날 파마소티칼 엘엘씨 | 치환된 피롤로피리미딘 화합물을 사용한 암의 치료방법, 이의 조성물 |
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-
1998
- 1998-09-23 US US09/160,212 patent/US6093728A/en not_active Expired - Fee Related
- 1998-09-23 TR TR2000/01546T patent/TR200001546T2/xx unknown
- 1998-09-23 AT AT98949464T patent/ATE281834T1/de not_active IP Right Cessation
- 1998-09-23 IL IL13510998A patent/IL135109A0/xx not_active IP Right Cessation
- 1998-09-23 KR KR1020007003192A patent/KR100547929B1/ko not_active IP Right Cessation
- 1998-09-23 NZ NZ503432A patent/NZ503432A/xx unknown
- 1998-09-23 DE DE69827516T patent/DE69827516T2/de not_active Expired - Fee Related
- 1998-09-23 JP JP2000513574A patent/JP2001517699A/ja not_active Withdrawn
- 1998-09-23 PL PL339744A patent/PL191618B1/pl not_active IP Right Cessation
- 1998-09-23 IL IL15864998A patent/IL158649A0/xx not_active IP Right Cessation
- 1998-09-23 HU HU0004024A patent/HUP0004024A3/hu unknown
- 1998-09-23 ES ES98949464T patent/ES2230719T3/es not_active Expired - Lifetime
- 1998-09-23 AU AU95781/98A patent/AU748849B2/en not_active Ceased
- 1998-09-23 CA CA002305370A patent/CA2305370C/en not_active Expired - Fee Related
- 1998-09-23 SK SK415-2000A patent/SK285357B6/sk unknown
- 1998-09-23 DK DK98949464T patent/DK1017384T3/da active
- 1998-09-23 CN CNB988107538A patent/CN1167420C/zh not_active Expired - Fee Related
- 1998-09-23 WO PCT/US1998/019973 patent/WO1999016438A1/en active IP Right Grant
- 1998-09-23 PT PT98949464T patent/PT1017384E/pt unknown
- 1998-09-23 RU RU2000110736/15A patent/RU2230553C2/ru not_active IP Right Cessation
- 1998-09-23 EP EP98949464A patent/EP1017384B1/en not_active Expired - Lifetime
- 1998-09-23 BR BR9812682-2A patent/BR9812682A/pt not_active Application Discontinuation
- 1998-09-23 UA UA2000042349A patent/UA72448C2/uk unknown
- 1998-09-25 AR ARP980104793A patent/AR017266A1/es unknown
- 1998-09-25 ZA ZA9808797A patent/ZA988797B/xx unknown
- 1998-09-25 TW TW087115979A patent/TW581815B/zh not_active IP Right Cessation
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2000
- 2000-03-15 IL IL135109A patent/IL135109A/en unknown
- 2000-03-24 NO NO20001555A patent/NO325663B1/no unknown
- 2000-04-19 BG BG104356A patent/BG64784B1/bg unknown
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2001
- 2001-04-23 HK HK01102854A patent/HK1032206A1/xx not_active IP Right Cessation
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2002
- 2002-03-15 NZ NZ517808A patent/NZ517808A/en unknown
- 2002-11-15 US US10/294,802 patent/US6855723B2/en not_active Expired - Fee Related
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2003
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