ZA200408965B - N-acylaminobenzene derivatives as selective monoamine oxidase B inhibitors - Google Patents
N-acylaminobenzene derivatives as selective monoamine oxidase B inhibitors Download PDFInfo
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- ZA200408965B ZA200408965B ZA200408965A ZA200408965A ZA200408965B ZA 200408965 B ZA200408965 B ZA 200408965B ZA 200408965 A ZA200408965 A ZA 200408965A ZA 200408965 A ZA200408965 A ZA 200408965A ZA 200408965 B ZA200408965 B ZA 200408965B
- Authority
- ZA
- South Africa
- Prior art keywords
- fluoro
- phenyl
- benzyloxy
- compounds
- formula
- Prior art date
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- 229940052764 dopaminergic anti-parkinson drug mao b inhibitors Drugs 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000006806 disease prevention Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- YSOKZEVIGMWTMH-UHFFFAOYSA-N methyl 3-[4-[(3-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC(F)=C1 YSOKZEVIGMWTMH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- FSCXRXBTLTZAGQ-UHFFFAOYSA-N methyl 3-[2-fluoro-4-[(3-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound C1=C(F)C(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC(F)=C1 FSCXRXBTLTZAGQ-UHFFFAOYSA-N 0.000 claims description 4
- PNAZMVPKBYPGJY-UHFFFAOYSA-N methyl 3-[4-[(4-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=C(F)C=C1 PNAZMVPKBYPGJY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- DXPFMUIHANEMMC-UHFFFAOYSA-N methyl 3-[3-fluoro-4-[(3-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound FC1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC(F)=C1 DXPFMUIHANEMMC-UHFFFAOYSA-N 0.000 claims description 3
- FSCRYJCZPUSDDL-UHFFFAOYSA-N n'-[4-[(3-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC(F)=C1 FSCRYJCZPUSDDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QOCHHCMABMDTMO-UHFFFAOYSA-N 1-n'-[2-fluoro-4-[(4-fluorophenyl)methoxy]phenyl]cyclopropane-1,1-dicarboxamide Chemical compound C=1C=C(OCC=2C=CC(F)=CC=2)C=C(F)C=1NC(=O)C1(C(=O)N)CC1 QOCHHCMABMDTMO-UHFFFAOYSA-N 0.000 claims description 2
- LVLJPBAKOGNTHQ-UHFFFAOYSA-N 2-acetamido-n-[2-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]acetamide Chemical compound C1=C(F)C(NC(=O)CNC(=O)C)=CC=C1OCC1=CC=CC(F)=C1 LVLJPBAKOGNTHQ-UHFFFAOYSA-N 0.000 claims description 2
- VBQXQSJSNGQECD-UHFFFAOYSA-N 2-amino-n-[2-fluoro-4-[(4-fluorophenyl)methoxy]phenyl]acetamide Chemical compound C1=C(F)C(NC(=O)CN)=CC=C1OCC1=CC=C(F)C=C1 VBQXQSJSNGQECD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- ZOSRQAUYYPIYFZ-UHFFFAOYSA-N methyl 3-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC(F)=C1 ZOSRQAUYYPIYFZ-UHFFFAOYSA-N 0.000 claims description 2
- GCJNTCVNQNYBGD-UHFFFAOYSA-N methyl 3-[4-[(2,4-difluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=C(F)C=C1F GCJNTCVNQNYBGD-UHFFFAOYSA-N 0.000 claims description 2
- KLYNKVSSHQJHDB-UHFFFAOYSA-N methyl 3-[4-[(2-fluorophenyl)methoxy]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC=C1F KLYNKVSSHQJHDB-UHFFFAOYSA-N 0.000 claims description 2
- RGXJNZQHQDHSDR-UHFFFAOYSA-N methyl 3-[4-[(3-fluorophenyl)methoxy]-3-methylanilino]-3-oxopropanoate Chemical compound CC1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC=CC(F)=C1 RGXJNZQHQDHSDR-UHFFFAOYSA-N 0.000 claims description 2
- OPWWYZQCBYXGNF-UHFFFAOYSA-N methyl 3-[4-[2-(4-fluorophenyl)ethenyl]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1C=CC1=CC=C(F)C=C1 OPWWYZQCBYXGNF-UHFFFAOYSA-N 0.000 claims description 2
- BVNFSSDJTNBBEC-UHFFFAOYSA-N methyl 3-[4-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-2-fluoroanilino]-3-oxopropanoate Chemical compound C1=C(F)C(NC(=O)CC(=O)OC)=CC=C1OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BVNFSSDJTNBBEC-UHFFFAOYSA-N 0.000 claims description 2
- QMDQOKOOHZNJHW-UHFFFAOYSA-N methyl 3-oxo-3-[4-[(2,4,5-trifluorophenyl)methoxy]anilino]propanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1OCC1=CC(F)=C(F)C=C1F QMDQOKOOHZNJHW-UHFFFAOYSA-N 0.000 claims description 2
- BVCMFOMYQJINHW-UHFFFAOYSA-N n'-(4-phenylmethoxyphenyl)propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC=C1 BVCMFOMYQJINHW-UHFFFAOYSA-N 0.000 claims description 2
- UZCBXBNTOLBPMZ-UHFFFAOYSA-N n'-[2-fluoro-4-[(4-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=C(F)C(NC(=O)CC(=O)N)=CC=C1OCC1=CC=C(F)C=C1 UZCBXBNTOLBPMZ-UHFFFAOYSA-N 0.000 claims description 2
- NMDPZRXRFZZSFJ-UHFFFAOYSA-N n'-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound ClC1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC(F)=C1 NMDPZRXRFZZSFJ-UHFFFAOYSA-N 0.000 claims description 2
- XFPILFDAAAEXKY-UHFFFAOYSA-N n'-[3-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound FC1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC(F)=C1 XFPILFDAAAEXKY-UHFFFAOYSA-N 0.000 claims description 2
- WNFLLLCFAKDMJK-UHFFFAOYSA-N n'-[4-[(2,4,5-trifluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC(F)=C(F)C=C1F WNFLLLCFAKDMJK-UHFFFAOYSA-N 0.000 claims description 2
- NRHVXCFIKWUOEX-UHFFFAOYSA-N n'-[4-[(2,4-difluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=C(F)C=C1F NRHVXCFIKWUOEX-UHFFFAOYSA-N 0.000 claims description 2
- YXJROUJIAVCJEI-UHFFFAOYSA-N n'-[4-[(2-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC=C1F YXJROUJIAVCJEI-UHFFFAOYSA-N 0.000 claims description 2
- DCSPPIPYFXIQJK-UHFFFAOYSA-N n'-[4-[(3-fluorophenyl)methoxy]-2-hydroxyphenyl]propanediamide Chemical compound C1=C(O)C(NC(=O)CC(=O)N)=CC=C1OCC1=CC=CC(F)=C1 DCSPPIPYFXIQJK-UHFFFAOYSA-N 0.000 claims description 2
- GCGIHGPECAUSJX-UHFFFAOYSA-N n'-[4-[(3-fluorophenyl)methoxy]-3-methylphenyl]propanediamide Chemical compound CC1=CC(NC(=O)CC(N)=O)=CC=C1OCC1=CC=CC(F)=C1 GCGIHGPECAUSJX-UHFFFAOYSA-N 0.000 claims description 2
- QZRKLBBAVNGURZ-UHFFFAOYSA-N n'-[4-[(3-fluorophenyl)methoxy]phenyl]-2-methylpropanediamide Chemical compound C1=CC(NC(=O)C(C(N)=O)C)=CC=C1OCC1=CC=CC(F)=C1 QZRKLBBAVNGURZ-UHFFFAOYSA-N 0.000 claims description 2
- QKQOELFRNYUVHS-UHFFFAOYSA-N n'-[4-[(4-chlorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=C(Cl)C=C1 QKQOELFRNYUVHS-UHFFFAOYSA-N 0.000 claims description 2
- SZFQBWJYCUHKSZ-UHFFFAOYSA-N n'-[4-[(4-fluorophenyl)methoxy]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1OCC1=CC=C(F)C=C1 SZFQBWJYCUHKSZ-UHFFFAOYSA-N 0.000 claims description 2
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- FNULRDMPMGOFCP-UHFFFAOYSA-N n'-[4-[2-(4-fluorophenyl)ethenyl]phenyl]propanediamide Chemical compound C1=CC(NC(=O)CC(=O)N)=CC=C1C=CC1=CC=C(F)C=C1 FNULRDMPMGOFCP-UHFFFAOYSA-N 0.000 claims description 2
- WUGYBNSKABDGRV-UHFFFAOYSA-N n-[2-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]-2-formamidoacetamide Chemical compound FC1=CC=CC(COC=2C=C(F)C(NC(=O)CNC=O)=CC=2)=C1 WUGYBNSKABDGRV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QQSCBAMXMRRLJC-UHFFFAOYSA-N 2-acetamido-n-[2-fluoro-4-[(4-fluorophenyl)methoxy]phenyl]acetamide Chemical compound C1=C(F)C(NC(=O)CNC(=O)C)=CC=C1OCC1=CC=C(F)C=C1 QQSCBAMXMRRLJC-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 claims 1
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- 102000010909 Monoamine Oxidase Human genes 0.000 description 30
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C233/00—Carboxylic acid amides
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- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
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- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/25—Aminoacetonitriles
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C07C323/41—Y being a hydrogen or an acyclic carbon atom
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EA009372B1 (ru) * | 2002-05-29 | 2007-12-28 | Ф. Хоффманн-Ля Рош Аг | N-ациламинобензольные производные в качестве селективных ингибиторов моноаминооксидазы в |
CA2527861A1 (en) * | 2003-07-21 | 2005-02-10 | Applied Research Systems Ars Holding N.V. | Alkynyl aryl carboxamides |
US20050089559A1 (en) * | 2003-10-23 | 2005-04-28 | Istvan Szelenyi | Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains |
CN100441188C (zh) * | 2003-10-23 | 2008-12-10 | 弗·哈夫曼-拉罗切有限公司 | 作为mao-b抑制剂的苯并氮杂衍生物 |
EP1588704A1 (en) * | 2004-04-22 | 2005-10-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of restless legs syndrome and addictive disorders |
UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
US7211573B2 (en) * | 2004-12-08 | 2007-05-01 | Hoffmann-La Roche Inc. | Malonamide derivatives |
WO2006089674A2 (en) | 2005-02-25 | 2006-08-31 | F.Hoffmann-La Roche Ag | Tablets with improved drug substance dispersibility |
WO2007008963A1 (en) * | 2005-07-13 | 2007-01-18 | Jenrin Discovery | Mao-b inhibitors useful for treating obesity |
US8722929B2 (en) * | 2006-10-10 | 2014-05-13 | Valeant Pharmaceuticals International | N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators |
US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
WO2010008894A1 (en) * | 2008-06-24 | 2010-01-21 | Valeant Pharmaceuticals International | Benzyloxy anilide derivatives useful as potassium channel modulators |
US9006371B1 (en) * | 2010-09-28 | 2015-04-14 | United States Of America As Represented By The Secretary Of The Navy | Synthesis of oligomeric silsesquioxane monomers for high performance polymers |
IT1404729B1 (it) * | 2011-01-27 | 2013-11-29 | Univ Pisa | Inibitori altamente selettivi dell'attivita' di adams |
JP2014512337A (ja) * | 2011-01-28 | 2014-05-22 | ユニバーシティ オブ ケンタッキー リサーチ ファウンデーション | スチルベン類似体およびがんを処置する方法 |
CN105237567B (zh) * | 2015-11-09 | 2017-09-29 | 河北工业大学 | 一种含芳甲基膦酸酯的制备方法 |
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DE1003753B (de) * | 1953-11-07 | 1957-03-07 | Dr Karl Kindler | Verfahren zur Herstellung von N-Dialkylaminoacylaminophenolaethern |
JPH05262718A (ja) * | 1992-03-23 | 1993-10-12 | Taisho Pharmaceut Co Ltd | 5−置換アミノ−2−フェノキシスルホンアニリド化合物 |
GB9313365D0 (en) * | 1993-06-29 | 1993-08-11 | Roussel Lab Ltd | Chemical compounds |
US5679715A (en) | 1995-06-07 | 1997-10-21 | Harris; Richard Y. | Method for treating multiple sclerosis |
WO1997033572A1 (en) | 1996-03-15 | 1997-09-18 | Somerset Pharmaceuticals, Inc. | Method for preventing and treating peripheral neurophathy by administering selegiline |
WO2001034172A2 (en) | 1999-11-05 | 2001-05-17 | Vela Pharmaceuticals Inc. | Methods and compositions for treating reward deficiency syndrome |
EA009372B1 (ru) * | 2002-05-29 | 2007-12-28 | Ф. Хоффманн-Ля Рош Аг | N-ациламинобензольные производные в качестве селективных ингибиторов моноаминооксидазы в |
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