WO2011071730A1 - Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds - Google Patents

Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds Download PDF

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Publication number
WO2011071730A1
WO2011071730A1 PCT/US2010/058594 US2010058594W WO2011071730A1 WO 2011071730 A1 WO2011071730 A1 WO 2011071730A1 US 2010058594 W US2010058594 W US 2010058594W WO 2011071730 A1 WO2011071730 A1 WO 2011071730A1
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WO
WIPO (PCT)
Prior art keywords
process according
formula
hydrogen
metal catalyst
compounds
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/US2010/058594
Other languages
English (en)
French (fr)
Inventor
Hossein Razavi
Jonathan Timothy Reeves
Sonia Rodriguez
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.)
Boehringer Ingelheim International GmbH
Original Assignee
Boehringer Ingelheim International GmbH
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 EP10787651A priority Critical patent/EP2509952A1/en
Priority to PH1/2012/501153A priority patent/PH12012501153A1/en
Priority to MX2012006524A priority patent/MX2012006524A/es
Priority to EA201200820A priority patent/EA201200820A1/ru
Priority to CA2782384A priority patent/CA2782384A1/en
Priority to JP2012543154A priority patent/JP2013512954A/ja
Priority to IN5081DEN2012 priority patent/IN2012DN05081A/en
Priority to CN2010800504234A priority patent/CN102596908A/zh
Application filed by Boehringer Ingelheim International GmbH filed Critical Boehringer Ingelheim International GmbH
Priority to BR112012013582A priority patent/BR112012013582A2/pt
Priority to AU2010328480A priority patent/AU2010328480A1/en
Publication of WO2011071730A1 publication Critical patent/WO2011071730A1/en
Priority to IL219274A priority patent/IL219274A0/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals

Definitions

  • This invention relates to novel processes for preparing compounds of the formula (I):
  • Indazole and azaindazole substituted compounds of formula II have been described as inhibitors of CCR1. Examples of such compounds are reported in WO 2009/134666 and WO 2010/036632. The compounds are useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of CCR1 including autoimmune diseases, such as rheumatoid arthritis and multiple sclerosis.
  • amine intermediate VI An essential intermediate in the above described synthesis of indazole and azaindazole substituted carboxamide compounds is the amine intermediate VI.
  • the known synthesis of the amine intermediate VI involves the conversion of the cyano compound below to the corresponding amine and is done by a 2-step process involving 1) reduction with sodium borohydride/trifluoroacetic acid/zinc bromide and in-situ tert- butoxycarbonylation,
  • an ionic salt comprising: i) hydrogenating a compound of the formula (II) using a metal catalyst, preferably a Pd or Ni based catalyst, more preferably Palladium over Carbon, most preferably 10%
  • Pd/C with water even more preferably 10% Pd/C/50% water
  • hydrogen preferably hydrogen at pressures of 15-1000 psi, preferably 100-200 psi for 2-20 hours, preferably 7 hours, at 0-100 ° C, preferably 25 ° C
  • an acid solution or gas preferably concentrated aqueous hydrochloric acid
  • the reaction is performed in a solvent chosen from an alcohol solvent, ester solvents, aqueous acids, ethers and toluene or other aromatic hydrocarbons solvents, preferably methanol, ethanol, isopropanol, or acetic acid, more preferably methanol, to provide a compound of the formula (I):
  • R is hydrogen or Cl-10 alkyl, preferably Cl-5 alkyl, more preferably methyl.
  • alkyl refers to a saturated aliphatic radical containing from one to ten carbon atoms.
  • Alkyl refers to both branched and unbranched alkyl groups.
  • a hydrogenation vessel is charged with 2-(methanesulfonyl)-4-cyanopyridine (8.00 g, 43.9 mmol), 10 wt.% Pd/C (50% water) (800 mg, 0.377 mmol) and MeOH (48 mL).
  • the mixture is hydrogenated under 100 psi of hydrogen at 25 ° C for 7 hours.
  • the reaction mixture is filtered to remove the catalyst, using MeOH to rinse, and the filtrate is concentrated to a volume of 24 mL. Isopropanol (48 mL) is added, followed by concentrated hydrochloric acid (4.03 mL, 48.3 mmol, 1.1 eq).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Pain & Pain Management (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
PCT/US2010/058594 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds Ceased WO2011071730A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
IN5081DEN2012 IN2012DN05081A (cs) 2009-12-08 2010-12-01
MX2012006524A MX2012006524A (es) 2009-12-08 2010-12-01 Proceso para la sintesis de compuestos intermedios de utilidad para preparar compuestos sustituidos de indazol y azaindol.
EA201200820A EA201200820A1 (ru) 2009-12-08 2010-12-01 Способ синтеза промежуточных продуктов, применимых для получения замещенных индазолов и азаиндазолов
CA2782384A CA2782384A1 (en) 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds
JP2012543154A JP2013512954A (ja) 2009-12-08 2010-12-01 置換インダゾール及びアザインダゾール化合物の生成に有効な中間体の合成方法
EP10787651A EP2509952A1 (en) 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds
AU2010328480A AU2010328480A1 (en) 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds
CN2010800504234A CN102596908A (zh) 2009-12-08 2010-12-01 用于制备取代的吲唑和氮杂吲唑化合物的中间体的合成方法
BR112012013582A BR112012013582A2 (pt) 2009-12-08 2010-12-01 processo para síntese de intermediários úteis para a produção de compostos de indazol e azaindazol substituídos
PH1/2012/501153A PH12012501153A1 (en) 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds
IL219274A IL219274A0 (en) 2009-12-08 2012-04-19 Process for synthesis of intermediates useful for making substituted indazole and azindazole compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26753809P 2009-12-08 2009-12-08
US61/267,538 2009-12-08

Publications (1)

Publication Number Publication Date
WO2011071730A1 true WO2011071730A1 (en) 2011-06-16

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ID=43416915

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PCT/US2010/058594 Ceased WO2011071730A1 (en) 2009-12-08 2010-12-01 Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds

Country Status (17)

Country Link
US (1) US20110137042A1 (cs)
EP (1) EP2509952A1 (cs)
JP (1) JP2013512954A (cs)
KR (1) KR20120101667A (cs)
CN (1) CN102596908A (cs)
AR (1) AR079324A1 (cs)
AU (1) AU2010328480A1 (cs)
BR (1) BR112012013582A2 (cs)
CA (1) CA2782384A1 (cs)
CL (1) CL2012001300A1 (cs)
EA (1) EA201200820A1 (cs)
IL (1) IL219274A0 (cs)
IN (1) IN2012DN05081A (cs)
MX (1) MX2012006524A (cs)
PH (1) PH12012501153A1 (cs)
TW (1) TW201144282A (cs)
WO (1) WO2011071730A1 (cs)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8063065B2 (en) 2008-09-26 2011-11-22 Boehringer Ingelheim International Gmbh Azaindazole compounds as CCR1 receptor antagonists
US8293917B2 (en) 2008-05-06 2012-10-23 Boehringer Ingelheim International Gmbh Pyrazole compounds as CCR1 antagonists
US8546442B2 (en) 2010-12-23 2013-10-01 Boehringer Ingelheim International Gmbh Pyrazolopiperidine compounds as CCR1 receptor antagonists
US8871786B2 (en) 2010-04-30 2014-10-28 Boehringer Ingelheim International Gmbh Azaindazole amide compounds as CCR1 receptor antagonists
US8927550B2 (en) 2009-10-27 2015-01-06 Boehringer Ingelheim International Gmbh Heterocyclic compounds as CCR1 receptor antagonists
US9056858B2 (en) 2009-10-21 2015-06-16 Boehringer Ingelheim International Gmbh Indazole and pyrazolopyridine compounds as CCR1 receptor antagonists

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5216912B2 (ja) 2008-04-29 2013-06-19 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃｃｒ１受容体拮抗薬としてのインダゾール化合物

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US8293917B2 (en) 2008-05-06 2012-10-23 Boehringer Ingelheim International Gmbh Pyrazole compounds as CCR1 antagonists
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US9056858B2 (en) 2009-10-21 2015-06-16 Boehringer Ingelheim International Gmbh Indazole and pyrazolopyridine compounds as CCR1 receptor antagonists
US8927550B2 (en) 2009-10-27 2015-01-06 Boehringer Ingelheim International Gmbh Heterocyclic compounds as CCR1 receptor antagonists
US8871786B2 (en) 2010-04-30 2014-10-28 Boehringer Ingelheim International Gmbh Azaindazole amide compounds as CCR1 receptor antagonists
US8546442B2 (en) 2010-12-23 2013-10-01 Boehringer Ingelheim International Gmbh Pyrazolopiperidine compounds as CCR1 receptor antagonists

Also Published As

Publication number Publication date
MX2012006524A (es) 2012-07-17
JP2013512954A (ja) 2013-04-18
CN102596908A (zh) 2012-07-18
CA2782384A1 (en) 2011-06-16
IL219274A0 (en) 2012-06-28
EA201200820A1 (ru) 2013-01-30
PH12012501153A1 (en) 2012-10-22
IN2012DN05081A (cs) 2015-10-09
AR079324A1 (es) 2012-01-18
AU2010328480A1 (en) 2012-05-17
EP2509952A1 (en) 2012-10-17
BR112012013582A2 (pt) 2016-07-05
US20110137042A1 (en) 2011-06-09
KR20120101667A (ko) 2012-09-14
TW201144282A (en) 2011-12-16
CL2012001300A1 (es) 2012-09-07

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