WO2011054530A1 - Gpbp inhibition using q2 peptidomimetics - Google Patents

Gpbp inhibition using q2 peptidomimetics Download PDF

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Publication number
WO2011054530A1
WO2011054530A1 PCT/EP2010/006757 EP2010006757W WO2011054530A1 WO 2011054530 A1 WO2011054530 A1 WO 2011054530A1 EP 2010006757 W EP2010006757 W EP 2010006757W WO 2011054530 A1 WO2011054530 A1 WO 2011054530A1
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Prior art keywords
alkyi
alkoxy
alkyl
hydroxy
halo
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Ceased
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PCT/EP2010/006757
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English (en)
French (fr)
Inventor
Juan Saus
Santos Fustero
F. Juan Sanz-Cervera
Enrique Perez-Paya
Raül BLASCO
Francisco Revert-Ros
Fernando Revert
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FibroStatin SL
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FibroStatin SL
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Priority to JP2012535688A priority Critical patent/JP5883794B2/ja
Priority to MX2012005281A priority patent/MX2012005281A/es
Priority to ES10779469.5T priority patent/ES2523118T3/es
Priority to CN201080050226.2A priority patent/CN102781898B/zh
Priority to EP10779469.5A priority patent/EP2496544B1/en
Priority to HK13102222.1A priority patent/HK1175164B/en
Publication of WO2011054530A1 publication Critical patent/WO2011054530A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
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    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
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    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/58—Amidines

Definitions

  • the present invention provides methods for treating antibody-mediated disorders, drug-resistant cancer, inflammation, protein misfolding and ER stress-mediated disorders, and aberrant apoptosis comprising administering one or more compounds or pharmaceutical compositions of the invention to a subject in need thereof.
  • R5 is selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, C C 6 alkyi, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo(C C 6 alkyi), Ci-C 6 alkoxy, halo(C-i-C6 alkoxy), amino, (C-1-C6 alkyl)amino, di(C C6 alkyl)amino, hydroxy(C C 6 alkyi), (d-C 6 alkoxy)C C 6 alkyi, and amino(Ci-C 6 alkyi);
  • R-i is hydrogen, halogen, hydroxy, C1-C6 alkyi, halo(CrC6 alkyi), C1-C6 alkoxy, or halo(d-C 6 alkoxy);
  • -CH CH-C(0)OH, alkoxy), or -OS(0) 2 CF 3 .
  • R 6 is hydroxy, C C 6 alkoxy, halo(C C 6 alkoxy), or -OS(0) 2 CF 3 .
  • alkali and alkaline earth metals such as sodium, lithium, potassium, calcium, magnesium, and the like
  • non-toxic ammonium, quaternary ammonium, and amine cations including, but not limited to ammonium, tetramethylammonium, tetraethylammonium, methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, and the like.
  • ammonium, tetramethylammonium, tetraethylammonium, methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, and the like See, for example, Berge S.M. et al., "Pharmaceutical Salts," J. Pharm. Sci., 1977;66:1-19 which is incorporated herein by reference.)
  • Compounds and pharmaceutical compositions of the present invention may be administered parenterally in a sterile medium.
  • the drug depending on the vehicle and concentration used, can either be suspended or dissolved in the vehicle.
  • adjuvants such as local anesthetics, preservatives and buffering agents can be dissolved in the vehicle.
  • alkenyl as used herein, means a straight or branched chain hydrocarbon containing from 2 to 10 carbons, unless otherwise specified, and containing at least one carbon-carbon double bond.
  • Representative examples of alkenyl include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3- butenyl, 4-pentenyl, 5-hexenyl, 2-heptenyl, 2-methyl-l-heptenyl, 3-decenyl, and 3,7-dimethylocta-2,6-dienyl.
  • alkyl as used herein, means a straight or branched chain hydrocarbon containing from 1 to 10 carbon atoms unless otherwise specified.
  • Representative examples of alkyl include, but are not limited to, methyl, ethyl, n- propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n- heptyl, n-octyl, n-nonyl, and n-decyl.
  • Example 25 3-[4"-hydroxy-2 , -methyl-3-(trlfluoromethyl)-(1,1 , ;4 , ,1")terphenyl- 2"-yl]propionic acid (12
  • Example 84 S- ⁇ -dimethoxy-S ⁇ '-dimethyHI ,1 ';4 ⁇ 1 ")terphenyl-2"- yljjpropionic acid (32)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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PCT/EP2010/006757 2009-11-05 2010-11-05 Gpbp inhibition using q2 peptidomimetics Ceased WO2011054530A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2012535688A JP5883794B2 (ja) 2009-11-05 2010-11-05 擬似ｑ２ペプチドを用いるｇｐｂｐ抑制
MX2012005281A MX2012005281A (es) 2009-11-05 2010-11-05 Inhibicion de gpbp utilizando peptidomimeticos q2.
ES10779469.5T ES2523118T3 (es) 2009-11-05 2010-11-05 Inhibición de GPBP utilizando peptidomiméticos de Q2
CN201080050226.2A CN102781898B (zh) 2009-11-05 2010-11-05 使用q2拟肽的gpbp抑制
EP10779469.5A EP2496544B1 (en) 2009-11-05 2010-11-05 Gpbp inhibition using q2 peptidomimetics
HK13102222.1A HK1175164B (en) 2009-11-05 2010-11-05 Gpbp inhibition using q2 peptidomimetics

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US25843209P 2009-11-05 2009-11-05
US61/258,432 2009-11-05

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WO2011054530A1 true WO2011054530A1 (en) 2011-05-12

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EP (1) EP2496544B1 (cg-RX-API-DMAC10.html)
JP (1) JP5883794B2 (cg-RX-API-DMAC10.html)
CN (1) CN102781898B (cg-RX-API-DMAC10.html)
ES (1) ES2523118T3 (cg-RX-API-DMAC10.html)
MX (1) MX2012005281A (cg-RX-API-DMAC10.html)
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012113785A1 (en) 2011-02-21 2012-08-30 Fibrostatin S.L. Methods for treating and diagnosing disease
WO2014006020A1 (en) 2012-07-02 2014-01-09 Fibrostatin, S.L. Gpbp-1 inhibition and its therapeutic use
WO2016107906A1 (en) 2014-12-31 2016-07-07 Fibrostatin, S.L. Methods for inhibiting mesenchymal phenotype after epithelial-to-mesenchymal transition
WO2017134146A1 (en) * 2016-02-02 2017-08-10 Fibrostatin, S.L. Gpbp inhibitors and uses and scaleable synthesis thereof
US10221138B2 (en) 2013-06-27 2019-03-05 Lg Chem, Ltd. Biaryl derivatives as GPR120 agonists

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2489815B1 (es) * 2013-02-21 2015-08-10 Centro De Investigación Príncipe Felipe Nuevos p-terfenilos hexakis-sustituidos con grupos bilaterales para el tratamiento de la infección por el virus de la inmunodeficiencia humana tipo 1 (VIH-1) y otras enfermedades
CN105723224A (zh) * 2013-09-27 2016-06-29 菲布他丁有限合伙公司 古德帕斯丘抗原结合蛋白检测和抑制以及其在糖尿病中的应用
MX385777B (es) * 2014-12-24 2025-03-04 Lg Chemical Ltd Derivado de biarilo como agonista de gpr120.
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