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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- UOJMTSCORVQOHS-UHFFFAOYSA-N pachypodol Natural products COc1cc(ccc1O)C2=C(C)C(=O)c3c(O)cc(C)cc3O2 UOJMTSCORVQOHS-UHFFFAOYSA-N 0.000 description 1
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- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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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
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- 125000003373 pyrazinyl 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- A—HUMAN NECESSITIES
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- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P3/00—Drugs for disorders of the metabolism
- 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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- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
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- Psychiatry (AREA)
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- Psychology (AREA)
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- Reproductive Health (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (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 |
|---|---|---|---|
| SE0502173 | 2005-10-03 |
Publications (1)
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| SA06270365B1 true SA06270365B1 (ar) | 2009-12-22 |
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Family Applications (1)
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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) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| CA2637392A1 (en) * | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
| WO2008121063A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | New imidazo[ 4,5-b]pyridine-7-carboxamides 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 |
| CN103209981B (zh) * | 2010-09-10 | 2016-12-28 | 盐野义制药株式会社 | 具有ampk活化作用的杂环稠合咪唑衍生物 |
| 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 |
| MA46888A (fr) * | 2016-11-28 | 2021-06-02 | Bristol Myers Squibb Co | Inhibiteurs de gsk-3 |
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| ID24300A (id) * | 1997-08-05 | 2000-07-13 | Pfizer Prod Inc | 4-AMINOPIROL(3,2-d)PIRIMIDIN SEBAGAI ANTAGONIS-ANTAGONIS RESEPTOR NEUROPEPTIDA Y |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| MXPA04007697A (es) * | 2002-02-06 | 2004-11-10 | Vertex Pharma | Compuestos de heteroarilo utiles como inhibidores de gsk-3. |
| KR20050002910A (ko) * | 2002-03-27 | 2005-01-10 | 알타나 파마 아게 | 신규한 알콕시피리딘-유도체 |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
| KR100791252B1 (ko) * | 2003-01-23 | 2008-01-03 | 크리스탈지노믹스(주) | 글리코겐 합성효소 키나아제 3β 활성 억제제, 이의제조방법 및 이를 유효성분으로 함유하는 약학 조성물 |
| US7468377B2 (en) * | 2003-10-01 | 2008-12-23 | Altana Pharma Ag | Imidazopyridine-derivatives as inductible no-synthase inhibitors |
| BRPI0414933A (pt) * | 2003-10-01 | 2006-11-07 | Altana Pharma Ag | derivativos de imidazopiridina como inibidores de óxido nìtrico sintase induzìvel |
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| CA2637392A1 (en) * | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
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2006
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- 2006-09-29 UY UY29823A patent/UY29823A1/es not_active Application Discontinuation
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- 2006-10-02 AU AU2006297889A patent/AU2006297889A1/en not_active Abandoned
- 2006-10-02 CN CNA2006800453255A patent/CN101321754A/zh active Pending
- 2006-10-02 BR BRPI0616663-6A patent/BRPI0616663A2/pt not_active IP Right Cessation
- 2006-10-02 JP JP2008534485A patent/JP2009510162A/ja active Pending
- 2006-10-02 EP EP06799715A patent/EP1934217A4/en not_active Withdrawn
- 2006-10-02 WO PCT/SE2006/001115 patent/WO2007040439A1/en not_active Ceased
- 2006-10-03 SA SA06270365A patent/SA06270365B1/ar unknown
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2008
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Also Published As
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| TW200800984A (en) | 2008-01-01 |
| ZA200802637B (en) | 2008-12-31 |
| NO20082054L (no) | 2008-06-02 |
| IL189945A0 (en) | 2008-08-07 |
| CN101321754A (zh) | 2008-12-10 |
| JP2009510162A (ja) | 2009-03-12 |
| UY29823A1 (es) | 2007-05-31 |
| AU2006297889A1 (en) | 2007-04-12 |
| KR20080057334A (ko) | 2008-06-24 |
| CA2624869A1 (en) | 2007-04-12 |
| AR057525A1 (es) | 2007-12-05 |
| US20080255106A1 (en) | 2008-10-16 |
| EP1934217A4 (en) | 2010-08-04 |
| EP1934217A1 (en) | 2008-06-25 |
| WO2007040439A1 (en) | 2007-04-12 |
| BRPI0616663A2 (pt) | 2011-06-28 |
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