CA2238171C - Quinoline derivatives as nk3 antagonists - Google Patents

Quinoline derivatives as nk3 antagonists Download PDF

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Publication number
CA2238171C
CA2238171C CA002238171A CA2238171A CA2238171C CA 2238171 C CA2238171 C CA 2238171C CA 002238171 A CA002238171 A CA 002238171A CA 2238171 A CA2238171 A CA 2238171A CA 2238171 C CA2238171 C CA 2238171C
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CA
Canada
Prior art keywords
mmol
dissolved
dryness
evaporated
group
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.)
Expired - Fee Related
Application number
CA002238171A
Other languages
English (en)
French (fr)
Other versions
CA2238171A1 (en
Inventor
Giuseppe Arnaldo Maria Giardina
Carlo Farina
Mario Grugni
Luca Francesco Raveglia
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.)
GlaxoSmithKline SpA
Original Assignee
SmithKline Beecham SpA
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 to GBGB9524104.8A priority Critical patent/GB9524104D0/en
Priority to JP09520159A priority patent/JP2000512614A/ja
Priority to EP96939926A priority patent/EP0874827B1/en
Priority to ES96939926T priority patent/ES2200080T3/es
Priority to DE69628334T priority patent/DE69628334T2/de
Priority to PCT/EP1996/005209 priority patent/WO1997019927A1/en
Priority to CA002238171A priority patent/CA2238171C/en
Application filed by SmithKline Beecham SpA filed Critical SmithKline Beecham SpA
Publication of CA2238171A1 publication Critical patent/CA2238171A1/en
Priority to US10/140,452 priority patent/US6743804B2/en
Priority to CY0400083A priority patent/CY2505B1/xx
Application granted granted Critical
Publication of CA2238171C publication Critical patent/CA2238171C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • 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
    • C07D409/12—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 linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002238171A 1995-11-24 1998-05-21 Quinoline derivatives as nk3 antagonists Expired - Fee Related CA2238171C (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GBGB9524104.8A GB9524104D0 (en) 1995-11-24 1995-11-24 Novel compounds
ES96939926T ES2200080T3 (es) 1995-11-24 1996-11-22 Derivados de quinolina que tienen propiedades antagonistas de neuroquininas 3.
DE69628334T DE69628334T2 (de) 1995-11-24 1996-11-22 Chinolin derivate als nk3 antagoniste
PCT/EP1996/005209 WO1997019927A1 (en) 1995-11-24 1996-11-22 Quinoline derivatives as nk3 antagonists
JP09520159A JP2000512614A (ja) 1995-11-24 1996-11-22 Ｎｋ３アンタゴニストとしてのキノリン誘導体
EP96939926A EP0874827B1 (en) 1995-11-24 1996-11-22 Quinoline derivatives as nk3 antagonists
CA002238171A CA2238171C (en) 1995-11-24 1998-05-21 Quinoline derivatives as nk3 antagonists
US10/140,452 US6743804B2 (en) 1995-11-24 2002-05-07 Quinoline derivatives as NK3 antagonists
CY0400083A CY2505B1 (en) 1995-11-24 2004-11-22 Quinoline derivatives as nk3 antagonists

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9524104.8A GB9524104D0 (en) 1995-11-24 1995-11-24 Novel compounds
CA002238171A CA2238171C (en) 1995-11-24 1998-05-21 Quinoline derivatives as nk3 antagonists

Publications (2)

Publication Number Publication Date
CA2238171A1 CA2238171A1 (en) 1999-11-21
CA2238171C true CA2238171C (en) 2008-07-22

Family

ID=31496493

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002238171A Expired - Fee Related CA2238171C (en) 1995-11-24 1998-05-21 Quinoline derivatives as nk3 antagonists

Country Status (9)

Country Link
US (1) US6743804B2 (enExample)
EP (1) EP0874827B1 (enExample)
JP (1) JP2000512614A (enExample)
CA (1) CA2238171C (enExample)
CY (1) CY2505B1 (enExample)
DE (1) DE69628334T2 (enExample)
ES (1) ES2200080T3 (enExample)
GB (1) GB9524104D0 (enExample)
WO (1) WO1997019927A1 (enExample)

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US7037922B1 (en) 2000-03-10 2006-05-02 Neurogen Corporation Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands
US6413982B1 (en) 1999-03-29 2002-07-02 Neurogen Corporation 4-substituted quinoline derivatives
ATE303988T1 (de) * 1999-06-14 2005-09-15 Lilly Co Eli Inhibitoren von serin proteasen
US6794393B1 (en) 1999-10-19 2004-09-21 Merck & Co., Inc. Tyrosine kinase inhibitors
CA2387351C (en) 1999-10-19 2009-09-08 Merck & Co., Inc. Indole derivatives as tyrosine kinase inhibitors
US6313138B1 (en) 2000-02-25 2001-11-06 Merck & Co., Inc. Tyrosine kinase inhibitors
US6420382B2 (en) 2000-02-25 2002-07-16 Merck & Co., Inc. Tyrosine kinase inhibitors
US6521618B2 (en) 2000-03-28 2003-02-18 Wyeth 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors
CA2424689A1 (en) 2000-10-17 2002-04-25 Merck & Co., Inc. Orally active salts with tyrosine kinase activity
GB0028964D0 (en) * 2000-11-28 2001-01-10 Smithkline Beecham Spa Novel compounds
AU2002361577A1 (en) 2001-10-30 2003-05-12 Merck And Co., Inc. Tyrosine kinase inhibitors
AU2003244080A1 (en) * 2002-06-26 2004-01-19 Kyowa Hakko Kogyo Co., Ltd. Phosphodiesterase inhibitor
DK1911763T3 (da) 2003-01-28 2010-11-15 Ironwood Pharmaceuticals Inc Sammensætninger til behandling af mavetarmsygdomme
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
RU2229475C1 (ru) * 2003-03-06 2004-05-27 ООО "Исследовательский институт химического разнообразия 6-сульфамоилхинолин-4-карбоновые кислоты, их производные и комбинаторная библиотека
TW200804288A (en) 2005-12-12 2008-01-16 Astrazeneca Ab Alkylsulphonamide quinolines
AU2008261102B2 (en) 2007-06-04 2013-11-28 Bausch Health Ireland Limited Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
WO2008154207A1 (en) * 2007-06-08 2008-12-18 The Burnham Institute For Medical Research Methods and compounds for regulating apoptosis
CA2930674A1 (en) 2008-06-04 2009-12-10 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP3241839B1 (en) 2008-07-16 2019-09-04 Bausch Health Ireland Limited Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
EP3939964A1 (en) 2008-12-31 2022-01-19 Ardelyx, Inc. Combinations for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders
WO2018129556A1 (en) 2017-01-09 2018-07-12 Ardelyx, Inc. Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
CN104902930A (zh) 2012-08-21 2015-09-09 阿德利克斯公司 在治疗与液体潴留或盐分过载相关的疾病和胃肠道疾病中用于抑制nhe-介导的反向转运的化合物和方法
US10376481B2 (en) 2012-08-21 2019-08-13 Ardelyx, Inc. Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders
EP2970384A1 (en) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
HK1220611A1 (zh) 2013-03-15 2017-05-12 Bausch Health Ireland Limited 用於治疗胃肠道病症的组成物
CA2909169A1 (en) 2013-04-12 2014-10-16 Ardelyx, Inc. Nhe3-binding compounds and methods for inhibiting phosphate transport
EP2986293A1 (en) 2013-04-19 2016-02-24 Astrazeneca AB A nk3 receptor antagonist compound (nk3ra) for use in a method for the treatment of polycystic ovary syndrome (pcos)
SI3004138T1 (sl) 2013-06-05 2024-07-31 Bausch Health Ireland Limited Ultra čisti agonisti gvanilat ciklaze C, postopek za njihovo pripravo in uporabo
MX387903B (es) * 2014-07-08 2025-03-19 Corteva Agriscience Llc Proceso para la preparacion de acidos 3-hidroxipicolinicos.
WO2017072629A1 (en) 2015-10-29 2017-05-04 Cadila Healthcare Limited Pharmaceutical combination of nk3 receptor antagonist and biguanides
EP3565811A1 (en) 2017-01-09 2019-11-13 Ardelyx, Inc. Inhibitors of nhe-mediated antiport
CN110267944B (zh) 2017-01-09 2024-03-08 阿德利克斯股份有限公司 可用于治疗胃肠道病症的化合物
CN113194948A (zh) * 2018-11-15 2021-07-30 国立大学法人九州大学 Il-31介导性疾病的预防或治疗剂及医药组合物

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FR2538388B1 (fr) * 1982-12-24 1985-06-21 Pharmuka Lab Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments
EP0916346A3 (en) * 1991-09-20 2000-12-06 Glaxo Group Limited NK-1 receptor antagonists and 5HT3 receptor antagonists for the treatment of emesis
NO179904C (no) * 1992-09-04 1997-01-08 Takeda Chemical Industries Ltd Kondenserte heterocykliske forbindelser og deres anvendelse
TW263498B (enExample) * 1993-11-10 1995-11-21 Takeda Pharm Industry Co Ltd
RO114445B1 (ro) * 1994-05-27 1999-04-30 Smithkline Beecham S.P.A. Derivaţi de chinolină antagonişti ai receptorului nk3 tachichinină,procedeu de preparare,compoziţii farmaceutice pe baza acestora şi metodă de tratament
IT1270615B (it) * 1994-07-14 1997-05-07 Smithkline Beecham Farma Uso di derivati di chinolina

Also Published As

Publication number Publication date
DE69628334D1 (de) 2003-06-26
CA2238171A1 (en) 1999-11-21
US6743804B2 (en) 2004-06-01
CY2505B1 (en) 2005-12-23
US20030195204A1 (en) 2003-10-16
EP0874827A1 (en) 1998-11-04
JP2000512614A (ja) 2000-09-26
GB9524104D0 (en) 1996-01-24
ES2200080T3 (es) 2004-03-01
DE69628334T2 (de) 2004-02-19
EP0874827B1 (en) 2003-05-21
WO1997019927A1 (en) 1997-06-05

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