CN105541828B - Amide imidazole derivative and application thereof - Google Patents
Amide imidazole derivative and application thereof Download PDFInfo
- Publication number
- CN105541828B CN105541828B CN201510895760.8A CN201510895760A CN105541828B CN 105541828 B CN105541828 B CN 105541828B CN 201510895760 A CN201510895760 A CN 201510895760A CN 105541828 B CN105541828 B CN 105541828B
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- CN
- China
- Prior art keywords
- imidazol
- carboxamido
- methyl
- propionic acid
- ester
- Prior art date
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- -1 Amide imidazole derivative Chemical class 0.000 title claims abstract description 416
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
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- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 100
- 235000010290 biphenyl Nutrition 0.000 claims description 54
- 238000002360 preparation method Methods 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 21
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 20
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 19
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 19
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 19
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 18
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 31
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- BGJLLVCRNMWTNA-SFHVURJKSA-N methyl (2S)-3-imidazol-1-yl-2-[(4-phenylbenzoyl)amino]propanoate Chemical compound COC(=O)[C@H](Cn1ccnc1)NC(=O)c1ccc(cc1)-c1ccccc1 BGJLLVCRNMWTNA-SFHVURJKSA-N 0.000 description 1
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- SVKWMNJUBVQCMA-FQEVSTJZSA-N propan-2-yl (2S)-2-[[4-(4-fluorophenyl)benzoyl]amino]-3-imidazol-1-ylpropanoate Chemical compound CC(C)OC(=O)[C@H](Cn1ccnc1)NC(=O)c1ccc(cc1)-c1ccc(F)cc1 SVKWMNJUBVQCMA-FQEVSTJZSA-N 0.000 description 1
- IRPWNLLRPUUENV-FQEVSTJZSA-N propan-2-yl (2S)-3-imidazol-1-yl-2-[(4-phenylbenzoyl)amino]propanoate Chemical compound CC(C)OC(=O)[C@H](Cn1ccnc1)NC(=O)c1ccc(cc1)-c1ccccc1 IRPWNLLRPUUENV-FQEVSTJZSA-N 0.000 description 1
- GWVWZJDELXVCNR-NRFANRHFSA-N propan-2-yl (2S)-3-imidazol-1-yl-2-[[4-(4-methylphenyl)benzoyl]amino]propanoate Chemical compound CC(C)OC(=O)[C@H](Cn1ccnc1)NC(=O)c1ccc(cc1)-c1ccc(C)cc1 GWVWZJDELXVCNR-NRFANRHFSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D233/61—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 with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen 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
- C07D233/64—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
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Bacterial species name | Species | Strain selection |
Candida albicans | Candida albicans | SC5314 |
Candida albicans | Candida albicans | Y0109 |
Candida glabrata | Candida glabrata | 537 |
Trichophyton rubrum | Trichophyton rubrum | Cmccftla |
Trichophyton verruciformis (Fr.) pers | Trichophyton verrucosum | |
Microsporidian gypseum | Microsporum gypseum | Cmccfmza |
Claims (12)
Priority Applications (2)
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CN201510895760.8A CN105541828B (en) | 2014-12-10 | 2015-12-08 | Amide imidazole derivative and application thereof |
CN201811434187.0A CN109485645B (en) | 2014-12-10 | 2015-12-08 | Benzothiazole derivative and application thereof |
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CN2014107561399 | 2014-12-10 | ||
CN201410756139.9A CN104530038A (en) | 2014-12-10 | 2014-12-10 | Amide imidazole derivative and application thereof |
CN201510895760.8A CN105541828B (en) | 2014-12-10 | 2015-12-08 | Amide imidazole derivative and application thereof |
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CN105541828B true CN105541828B (en) | 2019-04-02 |
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CN201410756139.9A Pending CN104530038A (en) | 2014-12-10 | 2014-12-10 | Amide imidazole derivative and application thereof |
CN201510895760.8A Active CN105541828B (en) | 2014-12-10 | 2015-12-08 | Amide imidazole derivative and application thereof |
CN201811434187.0A Active CN109485645B (en) | 2014-12-10 | 2015-12-08 | Benzothiazole derivative and application thereof |
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CN201410756139.9A Pending CN104530038A (en) | 2014-12-10 | 2014-12-10 | Amide imidazole derivative and application thereof |
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CN (3) | CN104530038A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104530038A (en) * | 2014-12-10 | 2015-04-22 | 沈阳药科大学 | Amide imidazole derivative and application thereof |
CN109485607B (en) * | 2018-10-25 | 2020-11-17 | 沈阳药科大学 | Beta-azole-phenyl ketone derivative and application thereof |
CN109851560B (en) * | 2019-01-09 | 2020-07-07 | 河南新天地药业股份有限公司 | Biphenyl diazole derivative and preparation method and application thereof |
CN110950845B (en) * | 2019-11-21 | 2023-04-18 | 聊城大学 | Formylacetamide azole derivative and application thereof |
RU2730492C1 (en) * | 2019-12-27 | 2020-08-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" | Method of producing alkyl 2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-(1h-azol-1-yl) propanoates |
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US4124369A (en) * | 1976-06-01 | 1978-11-07 | Bayer Aktiengesellschaft | Combating fungi and controlling plant growth with 1-amido-1-azolyl-2-hydroxy- or -keto-alkanes |
GB2136801A (en) * | 1983-03-11 | 1984-09-26 | Sandoz Ltd | Fungicidal N-acyl-1-aryl-2-azolyl-ethylamines |
CN1060163C (en) * | 1994-05-18 | 2001-01-03 | 诺瓦蒂斯有限公司 | Acylated aminoalknimidazoles and-triazoles |
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JPS5859975A (en) * | 1981-10-06 | 1983-04-09 | Kureha Chem Ind Co Ltd | N-(1-triazol-(1)-yl-2,2,2-trichloroethyl)-substituted amide derivative and controlling agent against powdery mildew containing said derivative |
DE3628650A1 (en) * | 1986-03-12 | 1987-09-24 | Bayer Ag | RENINE INHIBITORS, METHOD FOR THE PRODUCTION AND THEIR USE |
JP2006151812A (en) * | 2003-01-30 | 2006-06-15 | Meiji Seika Kaisha Ltd | New triazole derivative and antifungal agent having the same as active ingredient |
US20040191833A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
CN104530038A (en) * | 2014-12-10 | 2015-04-22 | 沈阳药科大学 | Amide imidazole derivative and application thereof |
-
2014
- 2014-12-10 CN CN201410756139.9A patent/CN104530038A/en active Pending
-
2015
- 2015-12-08 CN CN201510895760.8A patent/CN105541828B/en active Active
- 2015-12-08 CN CN201811434187.0A patent/CN109485645B/en active Active
Patent Citations (3)
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US4124369A (en) * | 1976-06-01 | 1978-11-07 | Bayer Aktiengesellschaft | Combating fungi and controlling plant growth with 1-amido-1-azolyl-2-hydroxy- or -keto-alkanes |
GB2136801A (en) * | 1983-03-11 | 1984-09-26 | Sandoz Ltd | Fungicidal N-acyl-1-aryl-2-azolyl-ethylamines |
CN1060163C (en) * | 1994-05-18 | 2001-01-03 | 诺瓦蒂斯有限公司 | Acylated aminoalknimidazoles and-triazoles |
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Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors;Bin Sun et al.;《Bioorganic & Medicinal Chemistry》;20150820;第23卷;第6763-6773页 |
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CN109485645A (en) | 2019-03-19 |
CN105541828A (en) | 2016-05-04 |
CN104530038A (en) | 2015-04-22 |
CN109485645B (en) | 2020-08-04 |
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