SA06270365B1 - مشتقات جديدة من 3H – اميدازو [4 ، 5 – b ] بيريدين - Google Patents
مشتقات جديدة من 3H – اميدازو [4 ، 5 – b ] بيريدين Download PDFInfo
- Publication number
- SA06270365B1 SA06270365B1 SA06270365A SA06270365A SA06270365B1 SA 06270365 B1 SA06270365 B1 SA 06270365B1 SA 06270365 A SA06270365 A SA 06270365A SA 06270365 A SA06270365 A SA 06270365A SA 06270365 B1 SA06270365 B1 SA 06270365B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- alkyl
- haloalkyl
- imidazo
- phenyl
- pyridine
- Prior art date
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- 150000005240 3H-imidazo[4,5-b]pyridines Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- 238000011282 treatment Methods 0.000 claims abstract description 28
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- 238000000034 method Methods 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 175
- 125000001188 haloalkyl group Chemical group 0.000 claims description 139
- 238000006467 substitution reaction Methods 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 125000000623 heterocyclic group Chemical group 0.000 claims description 66
- 125000004429 atom Chemical group 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 44
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- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 206010012289 Dementia Diseases 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- CELXZNNNPOEHAT-UHFFFAOYSA-N 1H-imidazo[4,5-b]pyridine-7-carboxamide hydrochloride Chemical compound Cl.N1C=NC2=NC=CC(=C21)C(=O)N CELXZNNNPOEHAT-UHFFFAOYSA-N 0.000 claims description 10
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
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- 206010027175 memory impairment Diseases 0.000 claims description 6
- NVVZAKSOQZCEKH-UHFFFAOYSA-N 7-chloro-2-[2-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC(F)(F)C1=CC=CC=C1C1=NC2=C(Cl)C=CN=C2N1 NVVZAKSOQZCEKH-UHFFFAOYSA-N 0.000 claims description 5
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- FRKZUWBAFXDJNJ-UHFFFAOYSA-N methyl 4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 FRKZUWBAFXDJNJ-UHFFFAOYSA-N 0.000 claims description 5
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- PYDQOBHBRGWVIL-UHFFFAOYSA-N [4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-morpholin-4-ylmethanone Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 PYDQOBHBRGWVIL-UHFFFAOYSA-N 0.000 claims description 4
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- MVLIFILYEOMNNW-UHFFFAOYSA-N methyl 4-(1h-imidazo[4,5-b]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 MVLIFILYEOMNNW-UHFFFAOYSA-N 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- UGEUOTKVTBSELL-UHFFFAOYSA-N 4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 UGEUOTKVTBSELL-UHFFFAOYSA-N 0.000 claims description 3
- XHYPOLPWZMNGGI-UHFFFAOYSA-N 4-[[3-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methyl]morpholine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=1)=CC=CC=1CN1CCOCC1 XHYPOLPWZMNGGI-UHFFFAOYSA-N 0.000 claims description 3
- PAAJESGBRNIYKE-UHFFFAOYSA-N 4-[[4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methyl]morpholine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCOCC1 PAAJESGBRNIYKE-UHFFFAOYSA-N 0.000 claims description 3
- QSMNDCHFVFRFHN-UHFFFAOYSA-N 7-chloro-2-(4-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 QSMNDCHFVFRFHN-UHFFFAOYSA-N 0.000 claims description 3
- KEKRVZJPBQWIMT-UHFFFAOYSA-N 7-chloro-2-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 KEKRVZJPBQWIMT-UHFFFAOYSA-N 0.000 claims description 3
- QELLNVILFUXQKO-UHFFFAOYSA-N 7-chloro-2-[3-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 QELLNVILFUXQKO-UHFFFAOYSA-N 0.000 claims description 3
- NXLVBOFEKKCHNY-UHFFFAOYSA-N 7-chloro-2-[4-(piperidin-1-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCCCC1 NXLVBOFEKKCHNY-UHFFFAOYSA-N 0.000 claims description 3
- OWURUNJNKVMBQR-UHFFFAOYSA-N 7-chloro-2-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 OWURUNJNKVMBQR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- JAVVBPBDSPVAOJ-UHFFFAOYSA-N 7-chloro-2-(3-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CS(=O)(=O)C1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 JAVVBPBDSPVAOJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| SE0502173 | 2005-10-03 |
Publications (1)
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| SA06270365B1 true SA06270365B1 (ar) | 2009-12-22 |
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| SA06270365A SA06270365B1 (ar) | 2005-10-03 | 2006-10-03 | مشتقات جديدة من 3H – اميدازو [4 ، 5 – b ] بيريدين |
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| Country | Link |
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| US (1) | US20080255106A1 (enExample) |
| EP (1) | EP1934217A4 (enExample) |
| JP (1) | JP2009510162A (enExample) |
| KR (1) | KR20080057334A (enExample) |
| CN (1) | CN101321754A (enExample) |
| AR (1) | AR057525A1 (enExample) |
| AU (1) | AU2006297889A1 (enExample) |
| BR (1) | BRPI0616663A2 (enExample) |
| CA (1) | CA2624869A1 (enExample) |
| IL (1) | IL189945A0 (enExample) |
| NO (1) | NO20082054L (enExample) |
| SA (1) | SA06270365B1 (enExample) |
| TW (1) | TW200800984A (enExample) |
| UY (1) | UY29823A1 (enExample) |
| WO (1) | WO2007040439A1 (enExample) |
| ZA (1) | ZA200802637B (enExample) |
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| UY29825A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones |
| JP2009523845A (ja) * | 2006-01-23 | 2009-06-25 | クリスタルゲノミクス インコーポレーテッド | たんぱく質キナーゼの活性を阻害するイミダゾピリジン誘導体、これの製造方法およびこれを含む薬学組成物 |
| JP2010523490A (ja) * | 2007-03-30 | 2010-07-15 | アストラゼネカ・アクチエボラーグ | 新規イミダゾ［４，５−ｂ］ピリジン−７−カルボキサミド７０４ |
| CN102127070A (zh) * | 2010-01-15 | 2011-07-20 | 山东轩竹医药科技有限公司 | 吡啶并环衍生物 |
| KR101889993B1 (ko) * | 2010-09-10 | 2018-08-20 | 시오노기세야쿠 가부시키가이샤 | Ａｍｐｋ 활성화 작용을 갖는 헤테로환 축합 이미다졸 유도체 |
| JP2017524739A (ja) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | 神経筋接合部関連疾患の処置方法 |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| CN107151235B (zh) * | 2016-03-04 | 2019-12-13 | 上海市计划生育科学研究所 | 噻二唑烷二酮基gsk3抑制剂在调节精子运动能力中的用途 |
| ES2896938T3 (es) * | 2016-11-28 | 2022-02-28 | Bristol Myers Squibb Co | Inhibidores de GSK-3 |
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| WO1999007703A1 (en) * | 1997-08-05 | 1999-02-18 | Pfizer Products Inc. | 4-AMINOPYRROLE(3,2-d) PYRIMIDINES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| KR20040084896A (ko) * | 2002-02-06 | 2004-10-06 | 버텍스 파마슈티칼스 인코포레이티드 | Ｇｓｋ-3의 억제제로서 유용한 헤테로아릴 화합물 |
| BR0308785A (pt) * | 2002-03-27 | 2005-01-11 | Altana Pharma Ag | Derivados de alcoxipiridina |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
| WO2004065370A1 (en) * | 2003-01-23 | 2004-08-05 | Crystalgenomics, Inc. | Glycogen synthase kinase 3beta inhibitor, composition and process for the preparation thereof |
| NZ546437A (en) * | 2003-10-01 | 2009-09-25 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| ATE399168T1 (de) * | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| UY29825A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones |
| JP2009523845A (ja) * | 2006-01-23 | 2009-06-25 | クリスタルゲノミクス インコーポレーテッド | たんぱく質キナーゼの活性を阻害するイミダゾピリジン誘導体、これの製造方法およびこれを含む薬学組成物 |
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2006
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- 2006-10-02 CA CA002624869A patent/CA2624869A1/en not_active Abandoned
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- 2006-10-02 US US12/088,897 patent/US20080255106A1/en not_active Abandoned
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2008
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Also Published As
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| IL189945A0 (en) | 2008-08-07 |
| ZA200802637B (en) | 2008-12-31 |
| US20080255106A1 (en) | 2008-10-16 |
| CN101321754A (zh) | 2008-12-10 |
| AU2006297889A1 (en) | 2007-04-12 |
| UY29823A1 (es) | 2007-05-31 |
| WO2007040439A1 (en) | 2007-04-12 |
| TW200800984A (en) | 2008-01-01 |
| KR20080057334A (ko) | 2008-06-24 |
| NO20082054L (no) | 2008-06-02 |
| EP1934217A4 (en) | 2010-08-04 |
| AR057525A1 (es) | 2007-12-05 |
| BRPI0616663A2 (pt) | 2011-06-28 |
| CA2624869A1 (en) | 2007-04-12 |
| JP2009510162A (ja) | 2009-03-12 |
| EP1934217A1 (en) | 2008-06-25 |
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