ZA200602446B - Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof - Google Patents
Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof Download PDFInfo
- Publication number
- ZA200602446B ZA200602446B ZA200602446A ZA200602446A ZA200602446B ZA 200602446 B ZA200602446 B ZA 200602446B ZA 200602446 A ZA200602446 A ZA 200602446A ZA 200602446 A ZA200602446 A ZA 200602446A ZA 200602446 B ZA200602446 B ZA 200602446B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- salkyl
- methyl
- 10aryl
- halogen
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title description 7
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- -1 C3.10cycloalkyl-C Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 208000002193 Pain Diseases 0.000 claims description 18
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- 230000036407 pain Effects 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
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- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims description 3
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- VAQJTZCSQQRNFJ-UHFFFAOYSA-N n-[2-tert-butyl-1-(oxan-4-ylmethyl)benzimidazol-5-yl]-n-methylbutane-1-sulfonamide Chemical compound CC(C)(C)C1=NC2=CC(N(C)S(=O)(=O)CCCC)=CC=C2N1CC1CCOCC1 VAQJTZCSQQRNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 2
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- NOXPGSDFQWSNSW-UHFFFAOYSA-N (sulfamoylamino)methane Chemical compound CNS(N)(=O)=O NOXPGSDFQWSNSW-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- RWCUVKIQGQGRBD-UHFFFAOYSA-N n-[2-tert-butyl-1-(oxan-4-ylmethyl)benzimidazol-5-yl]-2-(2-hydroxyethylamino)-n-methylethanesulfonamide Chemical compound CC(C)(C)C1=NC2=CC(N(C)S(=O)(=O)CCNCCO)=CC=C2N1CC1CCOCC1 RWCUVKIQGQGRBD-UHFFFAOYSA-N 0.000 claims 1
- QACIHMKLLVUOTD-UHFFFAOYSA-N n-[2-tert-butyl-1-(oxan-4-ylmethyl)benzimidazol-5-yl]-2-methoxy-n-methylethanesulfonamide Chemical compound CC(C)(C)C1=NC2=CC(N(C)S(=O)(=O)CCOC)=CC=C2N1CC1CCOCC1 QACIHMKLLVUOTD-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 40
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- 150000003254 radicals Chemical class 0.000 description 13
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- 125000001072 heteroaryl group Chemical group 0.000 description 11
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0302573A SE0302573D0 (sv) | 2003-09-26 | 2003-09-26 | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200602446B true ZA200602446B (en) | 2007-09-26 |
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| ZA200702131A ZA200702131B (en) | 2003-09-26 | 2007-03-13 | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof l |
| ZA200702226A ZA200702226B (en) | 2003-09-26 | 2007-03-16 | Compounds, compositions containing them, preparations thereof and uses thereof II |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200702131A ZA200702131B (en) | 2003-09-26 | 2007-03-13 | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof l |
| ZA200702226A ZA200702226B (en) | 2003-09-26 | 2007-03-16 | Compounds, compositions containing them, preparations thereof and uses thereof II |
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Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2294330T3 (es) | 2002-08-02 | 2008-04-01 | MERCK & CO., INC. | Derivados de furo(2,3-b)piridina sustituidos. |
| SE0302573D0 (sv) | 2003-09-26 | 2003-09-26 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
| WO2006033631A1 (en) * | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof i |
| KR101269869B1 (ko) | 2004-09-24 | 2013-06-07 | 네오메드 인스티튜트 | 벤즈이미다졸 유도체, 그를 함유하는 조성물, 그의 제조방법 및 그의 용도 |
| WO2006033630A1 (en) * | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Compounds, compositions containing them, preparation thereof and uses thereof iii |
| CN101052639B (zh) * | 2004-09-24 | 2010-10-27 | 阿斯利康(瑞典)有限公司 | 苯并咪唑衍生物、含有它们的组合物、其制备方法和其用途 |
| ES2318556T3 (es) | 2004-11-02 | 2009-05-01 | Pfizer, Inc. | Derivados de sulfonil bencimidazol. |
| JP2009502912A (ja) * | 2005-07-29 | 2009-01-29 | アストラゼネカ・アクチエボラーグ | ジェミナル（（ジフルオロシクロアルキル）メチル）アミンの製造方法 |
| TW200745049A (en) * | 2006-03-23 | 2007-12-16 | Astrazeneca Ab | New crystalline forms |
| TW200808769A (en) * | 2006-04-18 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
| US20080139846A1 (en) * | 2006-09-01 | 2008-06-12 | Astrazeneca Ab | New Process 298 |
| JP5159630B2 (ja) * | 2006-09-13 | 2013-03-06 | 協和発酵キリン株式会社 | 縮環複素環誘導体 |
| US20110086853A1 (en) * | 2009-10-08 | 2011-04-14 | William Brown | Therapeutic Compounds |
| RU2414899C1 (ru) * | 2009-12-29 | 2011-03-27 | Аверин Константин Михайлович | Средства для лечения рассеянного склероза |
| RU2454234C1 (ru) * | 2011-03-16 | 2012-06-27 | Константин Михайлович Аверин | Соли 1,3-диэтилбензимидазолия - иммуностимулирующие средства и фармацевтические композиции на их основе |
| UA119740C2 (uk) * | 2012-06-13 | 2019-08-12 | Сайтек Текнолоджи Корп. | Композиції стабілізатора, що містять заміщені хроманові сполуки, і способи застосування |
| MA37700B1 (fr) | 2012-06-26 | 2018-03-30 | Bayer Pharma AG | N-[4-(quinolin-4-yloxy)cyclohexyl(méthyl)](hétéro)arylcarboxamides utilisables en tant qu'antagonistes des récepteurs aux androgènes, leur production et leur utilisation en tant que médicaments |
| US20210017174A1 (en) | 2018-03-07 | 2021-01-21 | Bayer Aktiengesellschaft | Identification and use of erk5 inhibitor |
| EP3972963A1 (en) | 2019-05-21 | 2022-03-30 | Bayer Aktiengesellschaft | Identification and use of kras inhibitors |
| CN112010789A (zh) * | 2019-05-31 | 2020-12-01 | 中国科学院上海药物研究所 | 乙烯基磺酰胺或乙烯基酰胺类化合物及其制备方法和用途 |
| GB202019335D0 (en) * | 2020-12-08 | 2021-01-20 | Artelo Biosciences Ltd | Pharmaceutical compositions |
| EP4488276A1 (en) * | 2022-03-04 | 2025-01-08 | Samjin Pharmaceutical Co., Ltd. | Novel heterocyclic compound and pharmaceutical composition comprising same |
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| DE4237597A1 (de) | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
| WO1997024334A1 (en) * | 1995-12-28 | 1997-07-10 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| TW453999B (en) * | 1997-06-27 | 2001-09-11 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| US6348032B1 (en) * | 1998-11-23 | 2002-02-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with benzimidazole derivatives |
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| AU2005287429A1 (en) | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Compounds, compositions containing them, preparations thereof and uses thereof II |
| WO2006033631A1 (en) | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof i |
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| WO2006033627A1 (en) | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Compounds, compositions containing them, preparation thereof and uses thereof iiii |
| WO2006033628A1 (en) | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
| WO2006033630A1 (en) | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Compounds, compositions containing them, preparation thereof and uses thereof iii |
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| TW200745049A (en) | 2006-03-23 | 2007-12-16 | Astrazeneca Ab | New crystalline forms |
| TW200808769A (en) * | 2006-04-18 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
| TW200808772A (en) * | 2006-06-13 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
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- 2004-09-24 SI SI200431166T patent/SI1670769T1/sl unknown
- 2004-09-24 WO PCT/GB2004/004124 patent/WO2005030732A1/en not_active Ceased
- 2004-09-24 HR HR20090388T patent/HRP20090388T1/xx unknown
- 2004-09-24 CN CNA2004800350086A patent/CN1886379A/zh active Pending
- 2004-09-24 TW TW093129150A patent/TW200521117A/zh unknown
- 2004-09-24 AT AT04768667T patent/ATE430135T1/de active
- 2004-09-24 PT PT04768667T patent/PT1670769E/pt unknown
- 2004-09-24 KR KR1020067005825A patent/KR101170184B1/ko not_active Expired - Lifetime
- 2004-09-24 AR ARP040103467A patent/AR045819A1/es not_active Application Discontinuation
- 2004-09-24 RU RU2006113371/04A patent/RU2346938C2/ru active
- 2004-09-24 CN CN2010105277900A patent/CN102010373A/zh active Pending
- 2004-09-24 EP EP04768667A patent/EP1670769B1/en not_active Expired - Lifetime
- 2004-09-24 ES ES04768667T patent/ES2324669T3/es not_active Expired - Lifetime
- 2004-09-24 JP JP2006527490A patent/JP4896721B2/ja not_active Expired - Lifetime
- 2004-09-24 AU AU2004276062A patent/AU2004276062B2/en not_active Expired
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- 2004-09-24 DK DK04768667T patent/DK1670769T3/da active
- 2004-09-24 MX MXPA06003197A patent/MXPA06003197A/es active IP Right Grant
- 2004-09-24 US US10/573,054 patent/US8633235B2/en active Active
- 2004-09-24 UA UAA200602693A patent/UA86776C2/ru unknown
- 2004-09-24 UY UY28536A patent/UY28536A1/es unknown
- 2004-09-26 SA SA04250310A patent/SA04250310B1/ar unknown
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2006
- 2006-03-09 IL IL174215A patent/IL174215A0/en unknown
- 2006-03-22 CO CO06028452A patent/CO5680443A2/es not_active Application Discontinuation
- 2006-03-24 ZA ZA200602446A patent/ZA200602446B/en unknown
- 2006-04-21 IS IS8422A patent/IS8422A/is unknown
- 2006-04-26 NO NO20061839A patent/NO20061839L/no not_active Application Discontinuation
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2007
- 2007-03-13 ZA ZA200702131A patent/ZA200702131B/xx unknown
- 2007-03-16 ZA ZA200702226A patent/ZA200702226B/xx unknown
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2009
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