WO2005012263A1 - 5-ht2b receptor antagonists - Google Patents

5-ht2b receptor antagonists Download PDF

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Publication number
WO2005012263A1
WO2005012263A1 PCT/GB2004/003184 GB2004003184W WO2005012263A1 WO 2005012263 A1 WO2005012263 A1 WO 2005012263A1 GB 2004003184 W GB2004003184 W GB 2004003184W WO 2005012263 A1 WO2005012263 A1 WO 2005012263A1
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WO
WIPO (PCT)
Prior art keywords
optionally substituted
alkyl
phenyl
group
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2004/003184
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English (en)
French (fr)
Inventor
Richard Anthony Borman
Robert Alexander Coleman
Kenneth Lyle Clark
Alexander William Oxford
George Hynd
Janet Ann Archer
Amanda Aley
Neil Victor Harris
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmagene Laboratories Ltd
Original Assignee
Pharmagene Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0317346A external-priority patent/GB0317346D0/en
Application filed by Pharmagene Laboratories Ltd filed Critical Pharmagene Laboratories Ltd
Priority to CA002532505A priority Critical patent/CA2532505A1/en
Priority to EP04743517A priority patent/EP1648876A1/en
Priority to JP2006520897A priority patent/JP2006528617A/ja
Priority to US10/564,010 priority patent/US20090018150A1/en
Publication of WO2005012263A1 publication Critical patent/WO2005012263A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
    • C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
    • C04B35/632—Organic additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4168—1,3-Diazoles having a nitrogen attached in position 2, e.g. clonidine
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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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
    • C07D233/66—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
    • C07D233/88—Nitrogen atoms, e.g. allantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Definitions

  • a fourth aspect of the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of formula I as defined in the first aspect or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier or diluent, with the proviso that when R N1 , R N2 and R 2 are H, R 3 is methyl, and X is NH, then R 1 is not: phenyl; 3-1, 4 -Me-phenyl; 3 , 5-diacetyl-phenyl , 3- acetyl-phenyl; 4-acetyl-phenyl ; and 2-carboxy-phenyl .
  • R 7 is an optionally substituted bi-C 5 . 7 aryl group
  • the prefixes denote the number of carbon atoms, or range of number of carbon atoms.
  • the term "C ⁇ - 4 alkyl,” as used herein, pertains to an alkyl group having from 1 to 4 carbon atoms .
  • groups of alkyl groups include C ⁇ _4 alkyl ("lower alkyl"), C ⁇ . 7 alkyl, and C ⁇ . 2 o alkyl.
  • compositions may be formulated for any suitable route and means of administration.
  • Pharmaceutically acceptable carriers or diluents include those used in formulations suitable for oral, rectal, nasal, topical (including buccal and sublingual) , vaginal or parenteral (including subcutaneous, intramuscular, intravenous, intradermal, intrathecal and epidural) administration.
  • the formulations may conveniently be presented in unit dosage form and may be prepared by any of the methods well known in the art of pharmacy. Such methods include the step of bringing into association the active ingredient with the carrier which constitutes one or more accessory ingredients .
  • the formulations are prepared by uniformly and intimately bringing into association the active ingredient with liquid carriers or finely divided solid carriers or both, and then, if necessary, shaping the product.
  • composition or formulation to be administered will, in any event, contain a quantity of the active compound (s) in an amount effective to alleviate the symptoms of the subject being treated.
  • Parenteral administration is generally characterized by injection, either subcutaneously, intramuscularly or intravenously.
  • Injectables can be prepared in conventional forms, either as liquid solutions or suspensions, solid forms suitable for solution or suspension in liquid prior to infection, or as emulsions.
  • Suitable excipients are, for example, water, saline, dextrose, glycerol, ethanol or the like.
  • the pharmaceutical compositions to be administered may also contain minor amounts of non-toxic auxiliary substances such as wetting or emulsifying agents, pH buffering agents and the like, such as for example, sodium acetate, sorbitan monolaurate, triethanolamine oleate, triethanolamine sodium acetate, etc.
  • the boronic acid residue, or equivalent may be on the 4-position of the oxazole ring and the halogen, or equivalent, on the aryl group.
  • R 1 is an optionally substituted C 5 . 7 aryl group, then it is preferred that is is not substituted by a carbonyl based group, for example amido. It is also preferred that the sole substituent is not in the ortho position. If X is O, then it is preferred that R 1 is a C 9 - ⁇ 4 aryl group or a bi-C 5 . 7 aryl group, where the second aryl group is meta to the first .
  • R 1 is an optionally substituted C 9 - ⁇ 4 aryl group
  • preferred substituent groups for the C 9 - ⁇ 4 aryl group include halo, hydroxy, C ⁇ - 4 alkoxy, cyano, amino, amido and C ⁇ _ 4 alkyl, of which hydroxy, and C ⁇ - 4 alkoxy are more preferred. It is also preferred that the C 9 . X4 aryl group bears no oxo substituents.
  • the ⁇ NMR spectra were recorded on a Varian Unity Inova 400, which operates at 400 MHz for X H. It is equipped with a 5mm inverse detection triple resonance probe for detection of 1 H.
  • the magnetic field is provided by a 9.4 Tesla Oxford instruments super-conducting magnet.
  • the host computer is a Sun Microsystems SunBlade 1000 workstation.

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  • Pregnancy & Childbirth (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
PCT/GB2004/003184 2003-07-24 2004-07-23 5-ht2b receptor antagonists Ceased WO2005012263A1 (en)

Priority Applications (4)

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CA002532505A CA2532505A1 (en) 2003-07-24 2004-07-23 5-ht2b receptor antagonists
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US9295257B2 (en) 2011-03-25 2016-03-29 North Carolina State University Inhibition of bacterial biofilms and microbial growth with imidazole derivatives
US9351491B2 (en) 2008-12-08 2016-05-31 North Carolina State University Inhibition and dispersion of biofilms in plants with imidazole-triazole derivatives
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WO2007002563A1 (en) * 2005-06-27 2007-01-04 Exelixis, Inc. Imidazole based lxr modulators
US9000022B2 (en) 2005-06-27 2015-04-07 Exelixis Patent Company Llc Imidazole based LXR modulators
JP2008543971A (ja) * 2005-06-27 2008-12-04 エグゼリクシス， インコーポレイテッド イミダゾールに基づくｌｘｒモジュレーター
US8703805B2 (en) 2005-06-27 2014-04-22 Exelixis Patent Company Llc Modulators of LXR
US8569352B2 (en) 2005-06-27 2013-10-29 Exelixis Patent Company Llc Imidazole based LXR modulators
CN101472911B (zh) * 2006-04-19 2014-07-02 詹森药业有限公司 三取代的1,2,4-三唑
JP2009534357A (ja) * 2006-04-19 2009-09-24 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ 三置換１，２，４−トリアゾール
US8143419B2 (en) 2006-04-19 2012-03-27 Janssen Pharmaceutica N. V. Trisubstituted 1,2,4-triazoles
EA016289B1 (ru) * 2006-04-19 2012-03-30 Янссен Фармацевтика Н.В. Тризамещенные 1,2,4-триазолы
WO2007118903A1 (en) * 2006-04-19 2007-10-25 Janssen Pharmaceutica N.V. Trisubstituted 1,2,4-triazoles
US7998995B2 (en) 2006-12-08 2011-08-16 Exelixis Patent Company Llc LXR and FXR modulators
US7906544B2 (en) 2007-01-26 2011-03-15 North Carolina State University Inhibition of bacterial biofilms with imidazole derivatives
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US8404851B2 (en) 2007-10-18 2013-03-26 Janssen Pharmaceutica Nv 1,3,5-trisubstituted triazole derivative
US8440701B2 (en) 2007-10-18 2013-05-14 Janssen Pharmaceutica Nv Trisubstituted 1,2,4 triazoles
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