WO1998046589A2 - Indazole amide compounds as serotoninergic agents - Google Patents

Indazole amide compounds as serotoninergic agents Download PDF

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Publication number
WO1998046589A2
WO1998046589A2 PCT/EP1998/002129 EP9802129W WO9846589A2 WO 1998046589 A2 WO1998046589 A2 WO 1998046589A2 EP 9802129 W EP9802129 W EP 9802129W WO 9846589 A2 WO9846589 A2 WO 9846589A2
Authority
WO
WIPO (PCT)
Prior art keywords
compound
hydrogen
formula
isopropyl
alkyl
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/EP1998/002129
Other languages
English (en)
French (fr)
Other versions
WO1998046589B1 (en
WO1998046589A3 (en
Inventor
Alessandra Alisi
Mario Brufani
Nicola Cazzolla
Marilena Giannangeli
Mario Pinza
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.)
Angelini Ricerche SpA
Angelini Acraf SpA
Original Assignee
Aziende Chimiche Riunite Angelini Francesco ACRAF SpA
Angelini Ricerche 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 UA99116211A priority Critical patent/UA58550C2/uk
Priority to DE69806141T priority patent/DE69806141T2/de
Priority to HK00107144.0A priority patent/HK1027811B/xx
Priority to JP54347598A priority patent/JP4578581B2/ja
Priority to KR1019997009198A priority patent/KR100563867B1/ko
Priority to SI9830218T priority patent/SI0975623T1/xx
Priority to DK98919257T priority patent/DK0975623T3/da
Priority to US09/403,007 priority patent/US6197769B1/en
Priority to SK1423-99A priority patent/SK284731B6/sk
Priority to EP98919257A priority patent/EP0975623B1/en
Priority to HU0002057A priority patent/HU227973B1/hu
Priority to EA199900935A priority patent/EA002352B1/ru
Priority to CA002286870A priority patent/CA2286870C/en
Application filed by Aziende Chimiche Riunite Angelini Francesco ACRAF SpA, Angelini Ricerche SpA filed Critical Aziende Chimiche Riunite Angelini Francesco ACRAF SpA
Priority to AT98919257T priority patent/ATE219490T1/de
Priority to IL13212798A priority patent/IL132127A/xx
Priority to AU72159/98A priority patent/AU740360B2/en
Publication of WO1998046589A2 publication Critical patent/WO1998046589A2/en
Publication of WO1998046589A3 publication Critical patent/WO1998046589A3/en
Publication of WO1998046589B1 publication Critical patent/WO1998046589B1/en
Anticipated expiration legal-status Critical
Priority to BG103863A priority patent/BG64006B1/bg
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics

Definitions

  • the present invention relates to an indazole amide compound possessing a serotoninergic action, a method for preparing thereof and the pharmaceutical compositions containing the same.
  • aryl are phenyl, naphthyl and biphenyl.
  • heterocyclic rings are thienyl, furanyl, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, furazanyl, pyrrolinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, piperidinyl, piperazinyl, morpholinyl, triazinyl, thiazolyl, tetrazolyl and thiadiazolyl.
  • R-i and R 2 have the above mentioned meanings, and
  • Y is halogen, d) optionally forming an acid addition salt of an indazole amide compound of the formula (I) with a pharmaceutically acceptable organic or inorganic acid, or a pharmaceutically acceptable quaternary salt of an indazole amide compound of the formula (I).
  • step (b) is carried out according to techniques known to the person skilled in the art of the protecting group (Theodora W. Greene and Peter G.M. Wuts, "Protective groups in organic synthesis", pp. 309- 406, John Wiley & Sons, Inc., N.Y., 1991).
  • the deprotection of the protecting group is preferably carried out by catalytic hydrogenation.
  • An example of a suitable catalyst is palladium on activated carbon.
  • the deprotection is carried out by hydrogenation in the presence of a suitable diluent such as, for example, a low aliphatic alcohol, a low aliphatic acid and mixtures thereof.
  • a suitable diluent such as, for example, a low aliphatic alcohol, a low aliphatic acid and mixtures thereof.
  • An example of a preferred diluent is an ethyl alcohol /acetic acid mixture.
  • Typical examples of preferred organic and inorganic acids for forming addition salts of the present invention are oxalic, maleic, tartaric, methanesulphonic, sulphuric, phosphoric acid, hydrogen bromide and hydrogen chloride.
  • Methyl iodide is a typical example of a preferred compound forming a pharmaceutically acceptable quaternary salt of the invention.
  • the preparation of the above mentioned salts comprises addition (step d) of a pharmaceutically acceptable organic or inorganic acid, or of methyl iodide to an indazole amide compound of the formula (I) obtained in step c).
  • suitable dosage forms are tablets, capsules, coated tablets, granules, solutions and syrups for oral administration; creams, ointments and medicated adhesive strips for topical administration; suppositories for rectal administration and sterile solutions for injectable, aerosol or ophthalmic administration.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/EP1998/002129 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents Ceased WO1998046589A2 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
UA99116211A UA58550C2 (uk) 1997-04-15 1998-02-04 Індазоламідні сполуки, спосіб одержання, індазоламідна проміжна сполука та фармацевтична композиція
EA199900935A EA002352B1 (ru) 1997-04-15 1998-04-02 Производные индазоламида в качестве серотонинергических агентов
JP54347598A JP4578581B2 (ja) 1997-04-15 1998-04-02 セロトニン様作用薬としてのインダゾールアミド化合物
KR1019997009198A KR100563867B1 (ko) 1997-04-15 1998-04-02 혈관 수축제로써의 인다졸 아마이드 화합물
SI9830218T SI0975623T1 (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
DK98919257T DK0975623T3 (da) 1997-04-15 1998-04-02 Indazolamidforbindelser som sertoninerge midler
US09/403,007 US6197769B1 (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
SK1423-99A SK284731B6 (sk) 1997-04-15 1998-04-02 Indazolamidová zlúčenina, spôsob jej prípravy, medziprodukt na jej prípravu a farmaceutický prostriedok s jej obsahom
EP98919257A EP0975623B1 (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
DE69806141T DE69806141T2 (de) 1997-04-15 1998-04-02 Indazoleamid-verbindungen als serotoninergene mittel
CA002286870A CA2286870C (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
HK00107144.0A HK1027811B (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
HU0002057A HU227973B1 (hu) 1997-04-15 1998-04-02 Indazolamidok és az ezeket tartalmazó gyógyszerek
AT98919257T ATE219490T1 (de) 1997-04-15 1998-04-02 Indazoleamid-verbindungen als serotoninergene mittel
IL13212798A IL132127A (en) 1997-04-15 1998-04-02 Indazole amide compounds, a process for their preparation, intermediates thereof and pharmaceutical compositions comprising them
AU72159/98A AU740360B2 (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents
BG103863A BG64006B1 (bg) 1997-04-15 1999-11-05 Индазоламидни съединения като серотонинергични средства

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI97A000867 1997-04-15
IT97MI000867A IT1291569B1 (it) 1997-04-15 1997-04-15 Indazolammidi come agenti serotoninergici

Publications (3)

Publication Number Publication Date
WO1998046589A2 true WO1998046589A2 (en) 1998-10-22
WO1998046589A3 WO1998046589A3 (en) 1999-01-28
WO1998046589B1 WO1998046589B1 (en) 1999-03-04

Family

ID=11376888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/002129 Ceased WO1998046589A2 (en) 1997-04-15 1998-04-02 Indazole amide compounds as serotoninergic agents

Country Status (26)

Country Link
US (1) US6197769B1 (https=)
EP (1) EP0975623B1 (https=)
JP (2) JP4578581B2 (https=)
KR (1) KR100563867B1 (https=)
CN (1) CN1318416C (https=)
AR (1) AR012426A1 (https=)
AT (1) ATE219490T1 (https=)
AU (1) AU740360B2 (https=)
BG (1) BG64006B1 (https=)
CA (1) CA2286870C (https=)
CZ (1) CZ295190B6 (https=)
DE (1) DE69806141T2 (https=)
DK (1) DK0975623T3 (https=)
EA (1) EA002352B1 (https=)
ES (1) ES2178205T3 (https=)
GE (1) GEP20022654B (https=)
HU (1) HU227973B1 (https=)
IL (1) IL132127A (https=)
IT (1) IT1291569B1 (https=)
PL (1) PL193308B1 (https=)
PT (1) PT975623E (https=)
SK (1) SK284731B6 (https=)
TR (1) TR199902546T2 (https=)
UA (1) UA58550C2 (https=)
WO (1) WO1998046589A2 (https=)
ZA (1) ZA982926B (https=)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6197769B1 (en) * 1997-04-15 2001-03-06 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole amide compounds as serotoninergic agents
WO2004101548A1 (en) * 2003-05-15 2004-11-25 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole having analgesic activity ,
US7053089B2 (en) 2001-02-23 2006-05-30 Merck & Co., Inc. N-substituted nonaryl-heterocyclic NMDA/NR2B antagonists
US7259157B2 (en) 2001-04-03 2007-08-21 Merck & Co., Inc. N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B Antagonists
WO2009062883A1 (en) * 2007-11-12 2009-05-22 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Drug active in neuropathic pain
US20100056573A1 (en) * 2006-11-22 2010-03-04 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. 2-alkyl-indazole compounds for the treatment of certain cns-related disorders
US10208023B2 (en) 2013-03-01 2019-02-19 Mark G. DeGiacomo Heterocyclic inhibitors of the sodium channel

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20030287A1 (it) 2003-02-18 2004-08-19 Acraf Indazolammidi dotate di attivita' analgesica metodo, per
ITMI20031468A1 (it) * 2003-07-18 2005-01-19 Acraf Farmaco ativo nel dolore neuropatico
TW200533348A (en) * 2004-02-18 2005-10-16 Theravance Inc Indazole-carboxamide compounds as 5-ht4 receptor agonists
TWI351282B (en) 2004-04-07 2011-11-01 Theravance Inc Quinolinone-carboxamide compounds as 5-ht4 recepto
US7728006B2 (en) * 2004-04-07 2010-06-01 Theravance, Inc. Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US8309575B2 (en) 2004-04-07 2012-11-13 Theravance, Inc. Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US7399862B2 (en) * 2004-11-05 2008-07-15 Theravance, Inc. 5-HT4 receptor agonist compounds
WO2006052889A2 (en) * 2004-11-05 2006-05-18 Theravance, Inc. Quinolinone-carboxamide compounds
CA2588037A1 (en) * 2004-12-22 2006-06-29 Theravance, Inc. Indazole-carboxamide compounds
WO2006088988A1 (en) * 2005-02-17 2006-08-24 Theravance, Inc. Crystalline form of an indazole-carboxamide compound
CN101163701A (zh) * 2005-03-02 2008-04-16 施万制药 作为5-ht4受体激动剂的喹啉酮化合物
US8377968B2 (en) 2008-06-02 2013-02-19 Zalicus Pharmaceuticals, Ltd. N-piperidinyl acetamide derivatives as calcium channel blockers
KR20140041519A (ko) * 2011-06-07 2014-04-04 다이닛본 스미토모 세이야꾸 가부시끼가이샤 인다졸-유도체 및 피롤로피리딘-유도체 및 그의 약제학적 용도
CA2860250C (en) * 2012-02-21 2020-11-10 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. 1h-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors
RS54539B1 (sr) * 2012-02-21 2016-06-30 Aziende Chimiche Riunite Angelini Francesco - A.C.R.A.F. - S.P.A. Upotreba 1h-indazol-3-karboksamidnih jedinjenja kao inhibitora kinaze 3-beta glikogen sintetaze
CN114340670B (zh) 2019-07-11 2026-02-17 普拉克西斯精密药物股份有限公司 T-型钙通道调节剂的制剂及其使用方法

Family Cites Families (5)

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GB9103862D0 (en) * 1991-02-25 1991-04-10 Glaxo Group Ltd Chemical compounds
CA2116024A1 (en) * 1991-08-20 1993-03-04 Francis David King 5-ht4 receptor antagonists
IL117438A (en) * 1995-03-16 2001-12-23 Lilly Co Eli Indazolecarboxamides, their preparation and pharmaceutical compositions containing them
EP0829474B1 (en) * 1995-05-31 2003-04-09 Nisshin Seifun Group Inc. Indazole derivatives having monocyclic amino group
IT1291569B1 (it) * 1997-04-15 1999-01-11 Angelini Ricerche Spa Indazolammidi come agenti serotoninergici

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6197769B1 (en) * 1997-04-15 2001-03-06 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole amide compounds as serotoninergic agents
US7053089B2 (en) 2001-02-23 2006-05-30 Merck & Co., Inc. N-substituted nonaryl-heterocyclic NMDA/NR2B antagonists
AU2002338334B2 (en) * 2001-04-03 2008-08-14 Merck & Co., Inc. N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B antagonists
AU2002338334B8 (en) * 2001-04-03 2008-09-18 Merck & Co., Inc. N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B antagonists
US7259157B2 (en) 2001-04-03 2007-08-21 Merck & Co., Inc. N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B Antagonists
US7662836B2 (en) 2003-05-15 2010-02-16 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole having analgesic activity
EA008499B1 (ru) * 2003-05-15 2007-06-29 Ацьенде Кимике Рьюните Анджелини Франческо А.К.Р.А.Ф. С.П.А. Индазолы, обладающие анальгетической активностью
WO2004101548A1 (en) * 2003-05-15 2004-11-25 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole having analgesic activity ,
AU2004238449B2 (en) * 2003-05-15 2010-09-02 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole having analgesic activity ,
KR101093048B1 (ko) * 2003-05-15 2011-12-13 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 진통 작용을 가진 인다졸
US8415476B2 (en) 2003-05-15 2013-04-09 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Indazole having analgesic activity
US20100056573A1 (en) * 2006-11-22 2010-03-04 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. 2-alkyl-indazole compounds for the treatment of certain cns-related disorders
US8507528B2 (en) * 2006-11-22 2013-08-13 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. 2-alkyl-indazole compounds for the treatment of certain cns-related disorders
WO2009062883A1 (en) * 2007-11-12 2009-05-22 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Drug active in neuropathic pain
JP2011503030A (ja) * 2007-11-12 2011-01-27 アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ 神経因性疼痛に活性な薬物
US8455519B2 (en) 2007-11-12 2013-06-04 Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. Drug active in neuropathic pain
EA019405B1 (ru) * 2007-11-12 2014-03-31 Ацьенде Кимике Рьюните Анджелини Франческо A.К.P.A.Ф. С.П.А. Лекарственное средство, активное в отношении невропатической боли
US10208023B2 (en) 2013-03-01 2019-02-19 Mark G. DeGiacomo Heterocyclic inhibitors of the sodium channel

Also Published As

Publication number Publication date
CA2286870C (en) 2007-05-22
EP0975623A2 (en) 2000-02-02
JP5237324B2 (ja) 2013-07-17
DK0975623T3 (da) 2002-10-14
TR199902546T2 (xx) 2000-05-22
UA58550C2 (uk) 2003-08-15
KR20010006120A (ko) 2001-01-26
HU227973B1 (hu) 2012-07-30
HUP0002057A2 (hu) 2001-04-28
CN1252798A (zh) 2000-05-10
KR100563867B1 (ko) 2006-03-24
AR012426A1 (es) 2000-10-18
HUP0002057A3 (en) 2002-01-28
DE69806141T2 (de) 2003-01-30
PT975623E (pt) 2002-10-31
EA199900935A1 (ru) 2000-04-24
HK1027811A1 (en) 2001-01-23
AU740360B2 (en) 2001-11-01
CA2286870A1 (en) 1998-10-22
DE69806141D1 (de) 2002-07-25
SK284731B6 (sk) 2005-10-06
ATE219490T1 (de) 2002-07-15
CZ362599A3 (cs) 2000-04-12
ITMI970867A1 (it) 1998-10-15
ZA982926B (en) 1998-10-09
CN1318416C (zh) 2007-05-30
EA002352B1 (ru) 2002-04-25
SK142399A3 (en) 2000-08-14
IT1291569B1 (it) 1999-01-11
US6197769B1 (en) 2001-03-06
BG64006B1 (bg) 2003-09-30
IL132127A (en) 2005-06-19
EP0975623B1 (en) 2002-06-19
PL336348A1 (en) 2000-06-19
JP2001518906A (ja) 2001-10-16
GEP20022654B (en) 2002-03-25
IL132127A0 (en) 2001-03-19
JP2010195813A (ja) 2010-09-09
CZ295190B6 (cs) 2005-06-15
BG103863A (en) 2000-07-31
WO1998046589A3 (en) 1999-01-28
AU7215998A (en) 1998-11-11
PL193308B1 (pl) 2007-01-31
ES2178205T3 (es) 2002-12-16
JP4578581B2 (ja) 2010-11-10

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