ZA200305626B - Imidazole derivatives. - Google Patents
Imidazole derivatives. Download PDFInfo
- Publication number
- ZA200305626B ZA200305626B ZA200305626A ZA200305626A ZA200305626B ZA 200305626 B ZA200305626 B ZA 200305626B ZA 200305626 A ZA200305626 A ZA 200305626A ZA 200305626 A ZA200305626 A ZA 200305626A ZA 200305626 B ZA200305626 B ZA 200305626B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- formula
- phenyl
- imidazol
- lower alkyl
- Prior art date
Links
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
- 150000002460 imidazoles Chemical class 0.000 title 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 213
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- -1 nitro, benzyloxy, hydroxy Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 230000004770 neurodegeneration Effects 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000001684 chronic effect Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 7
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
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- 208000036142 Viral infection Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- AJFWRZUSIQFQKM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[(2-methylimidazol-1-yl)methyl]pyrazole Chemical compound CC1=NC=CN1CC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C=C1 AJFWRZUSIQFQKM-UHFFFAOYSA-N 0.000 claims description 2
- PUZACGGRUZJBQO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-[(2-methylimidazol-1-yl)methyl]pyrazole Chemical compound CC1=NC=CN1CC1=CN(C=2C=C(Cl)C(Cl)=CC=2)N=C1 PUZACGGRUZJBQO-UHFFFAOYSA-N 0.000 claims description 2
- QUMOIQBLMRAOCX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-imidazol-1-yl-3-methylpyrazole Chemical compound CC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C=C1N1C=CN=C1 QUMOIQBLMRAOCX-UHFFFAOYSA-N 0.000 claims description 2
- WWLNOHNILZUXSW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CC=NC(C=2C=C(Cl)C(Cl)=CC=2)=C1 WWLNOHNILZUXSW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- HZFKNZVXVQVYMK-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-5-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CN=CC(C=2C=C(Cl)C(F)=CC=2)=C1 HZFKNZVXVQVYMK-UHFFFAOYSA-N 0.000 claims description 2
- WPINCYFUGZDAJF-UHFFFAOYSA-N 3-(4-chloro-3-methylphenyl)-5-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CN=CC(C=2C=C(C)C(Cl)=CC=2)=C1 WPINCYFUGZDAJF-UHFFFAOYSA-N 0.000 claims description 2
- RASQRGFTCCTZCY-UHFFFAOYSA-N 3-(4-fluoro-3-methylphenyl)-5-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CN=CC(C=2C=C(C)C(F)=CC=2)=C1 RASQRGFTCCTZCY-UHFFFAOYSA-N 0.000 claims description 2
- JEAGWXFPBOBGEN-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-5-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CN=CC(C=2C=C(C(Cl)=CC=2)C(F)(F)F)=C1 JEAGWXFPBOBGEN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 229910000104 sodium hydride Inorganic materials 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 39
- 239000012312 sodium hydride Substances 0.000 description 39
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 34
- 239000012458 free base Substances 0.000 description 34
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- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
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Classifications
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/84—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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AU2003245259A1 (en) * | 2002-05-02 | 2003-11-17 | Neurogen Corporation | Substituted imidazole derivatives: gabaa receptor ligands |
US7223759B2 (en) | 2003-09-15 | 2007-05-29 | Anadys Pharmaceuticals, Inc. | Antibacterial 3,5-diaminopiperidine-substituted aromatic and heteroaromatic compounds |
MXPA06014909A (es) | 2004-06-18 | 2007-02-28 | Chiron Corp | Derivados de n-(1-(1-bencil -4-fenil-1h -imidazol -2-il)-2, 2-dimetilpropil) benzamida y compuestos relacionados como inhibidores de proteina de huso de cinesina (ksp) para el tratamiento del cancer. |
ITRM20050094A1 (it) * | 2005-03-04 | 2006-09-05 | Univ Siena | Derivati del 1-(1,5-di(4-clorofenil)-2metil-1h-3-pirroli)metil)-4-metilpiperazina (bm 212), procedimento per la loro produzione e uso di essi come antitubercolari. |
US7939556B2 (en) | 2005-10-14 | 2011-05-10 | Neurosearch A/S | Imidazole derivatives and their use for modulating the GABAA receptor complex |
KR100694181B1 (ko) * | 2005-11-25 | 2007-03-12 | 연세대학교 산학협력단 | 근원세포 또는 근섬유로부터 신경세포 분화를 유도하는화합물, 이를 포함하는 약학적 조성물, 신경세포 분화를유도하는 방법 및 신경세포 분화를 유도하는 화합물을검색하는 스크리닝 방법 |
CN101711242B (zh) * | 2007-05-23 | 2013-09-25 | 阿勒根公司 | 作为肾上腺素能受体激动剂的((二环杂芳基)咪唑基)甲基杂芳基化合物 |
WO2010009327A1 (en) | 2008-07-17 | 2010-01-21 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Compounds for the treatment of pathologies associated with aging and degenerative disorders |
BRPI0916576A2 (pt) | 2008-08-04 | 2017-06-27 | Chdi Inc | pelo menos uma entidade química, composição farmacêutica, e, método para tratar uma condição ou distúrbio. |
EP2528441A4 (en) | 2010-01-25 | 2013-07-10 | Chdi Foundation Inc | CERTAIN KYNURENIN-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF |
WO2011101457A1 (en) | 2010-02-18 | 2011-08-25 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Chimeric surface active proteins |
US9394290B2 (en) | 2010-10-21 | 2016-07-19 | Universitaet Des Saarlandes Campus Saarbruecken | Selective CYP11B1 inhibitors for the treatment of cortisol dependent diseases |
SG2014011654A (en) | 2011-08-30 | 2014-08-28 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
AU2012302144B2 (en) | 2011-08-30 | 2017-06-15 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
CA2850508A1 (en) * | 2011-09-30 | 2013-04-04 | Endo Pharmaceuticals Inc. | Imidazole derivatives as cyp17 inhibitors for the treatment of cancer |
CA2955379C (en) | 2014-07-17 | 2022-12-13 | Chdi Foundation, Inc. | Methods and compositions for treating hiv-related disorders |
WO2016025917A1 (en) * | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Triazoles as nr2b receptor inhibitors |
US10155727B2 (en) * | 2014-08-15 | 2018-12-18 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
US10071988B2 (en) | 2016-02-10 | 2018-09-11 | Janssen Pharmaceutica Nv | Substituted 1,2,3-triazoles as NR2B-selective NMDA modulators |
TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之1H-咪唑並[4,5-b]吡啶-2(3H)-酮及其作為GLUN2B受體調節劑之用途 |
TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
HRP20220331T1 (hr) | 2018-03-08 | 2022-05-13 | Incyte Corporation | Spojevi aminopirazin diola kao inhibitori pi3k-y |
WO2019193516A2 (en) | 2018-04-04 | 2019-10-10 | Janssen Pharmaceutica Nv | Substituted pyridine and pyrimidines and their use as glun2b receptor modulators |
US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
EP3982958A1 (en) | 2019-06-14 | 2022-04-20 | Janssen Pharmaceutica NV | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
JOP20210328A1 (ar) | 2019-06-14 | 2023-01-30 | Janssen Pharmaceutica Nv | مركبات أميدات بيريدين-بيرازولو المستبدلة واستخدامها باعتبارها معدِّلات لمستقبل الغلوتومات "glun2b" |
JP2022536773A (ja) | 2019-06-14 | 2022-08-18 | ヤンセン ファーマシューティカ エヌ.ベー. | 置換ピラゾロピラジン及びglun2b受容体調節因子としてのそれらの使用 |
WO2020249796A1 (en) | 2019-06-14 | 2020-12-17 | Janssen Pharmaceutica Nv | Pyrazine carbamates and their use as glun2b receptor modulators |
AU2020293584A1 (en) | 2019-06-14 | 2022-01-20 | Janssen Pharmaceutica Nv | Pyridine carbamates and their use as GluN2B receptor modulators |
US20220324860A1 (en) | 2019-06-14 | 2022-10-13 | Janssen Pharmaceutica Nv | SUBSTITUTED PYRAZOLO[4,3-b]PYRIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS |
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DE3627155A1 (de) | 1986-08-11 | 1988-02-18 | Schering Ag | Imidazol-derivate |
CN1040107C (zh) * | 1993-01-02 | 1998-10-07 | 山道士有限公司 | 咪唑基甲基吡啶 |
US5872136A (en) * | 1996-04-03 | 1999-02-16 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
US5998424A (en) * | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
IT1300055B1 (it) | 1998-04-17 | 2000-04-05 | Boehringer Ingelheim Italia | Eterocicli con anello a 5 termini difenil-sostituiti loro procedimento di preparazione e loro impiego come farmici |
ATE257827T1 (de) | 1999-07-21 | 2004-01-15 | Hoffmann La Roche | Triazolderivate |
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2001
- 2001-12-20 US US10/029,342 patent/US6610723B2/en not_active Expired - Lifetime
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2002
- 2002-01-21 CN CN2010101215002A patent/CN101798298B/zh not_active Expired - Fee Related
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- 2002-01-21 KR KR1020037009992A patent/KR100619106B1/ko not_active IP Right Cessation
- 2002-01-21 MX MXPA03006773A patent/MXPA03006773A/es active IP Right Grant
- 2002-01-21 JP JP2002561027A patent/JP4094956B2/ja not_active Expired - Fee Related
- 2002-01-21 DK DK02714095T patent/DK1358165T3/da active
- 2002-01-21 DE DE60231477T patent/DE60231477D1/de not_active Expired - Lifetime
- 2002-01-21 EP EP02714095A patent/EP1358165B1/en not_active Expired - Lifetime
- 2002-01-21 PT PT02714095T patent/PT1358165E/pt unknown
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- 2002-01-21 CA CA002434813A patent/CA2434813C/en not_active Expired - Fee Related
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- 2002-01-28 GT GT200200013A patent/GT200200013A/es unknown
- 2002-01-28 GC GCP20021833 patent/GC0000318A/en active
- 2002-01-29 JO JO20029A patent/JO2292B1/en active
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2003
- 2003-02-11 US US10/364,596 patent/US6683097B2/en not_active Expired - Lifetime
- 2003-02-13 US US10/365,995 patent/US6667335B2/en not_active Expired - Lifetime
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2004
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2009
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