WO2015110886A1 - A process for preparation of (2s, 5r)-7-oxo-n-[(3s)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo [3.2.1]octane-2-carboxamide - Google Patents

A process for preparation of (2s, 5r)-7-oxo-n-[(3s)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo [3.2.1]octane-2-carboxamide Download PDF

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Publication number
WO2015110886A1
WO2015110886A1 PCT/IB2014/067382 IB2014067382W WO2015110886A1 WO 2015110886 A1 WO2015110886 A1 WO 2015110886A1 IB 2014067382 W IB2014067382 W IB 2014067382W WO 2015110886 A1 WO2015110886 A1 WO 2015110886A1
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formula
compound
preparation
reacting
process according
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PCT/IB2014/067382
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English (en)
French (fr)
Inventor
Ravikumar Tadiparthi
Satish BIRAJDAR
Bharat DOND
Vijaykumar Jagdishwar Patil
Mahesh Vithalbhai Patel
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Wockhardt Limited
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Publication of WO2015110886A1 publication Critical patent/WO2015110886A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the invention relates to a process for preparation of (25, 5R)-7-oxo- pyrrolidin-3-yloxy]-6-(sulfooxy)-l ,6-diazabicyclo[3.2.1]octane-2-carboxamide.
  • a compound of Formula (I), chemically known as (25, 5i?)-7-oxo-N-[(35)- pyrrolidin-3-yloxy]-6-(sulfooxy)-l ,6-diazabicyclo[3.2.1]octane-2-carboxamide has antibacterial properties and is disclosed in PCT International Patent Application No. PCT/IB2013/053092.
  • OBn refers to benzyloxy.
  • EDC refers to l-ethyl-3-(3-dimethylamino propyl)carbodiimide.
  • HOBt refers to 1 -hydro xybenzotriazole.
  • TBAA tetrabutylammonium acetate
  • (Boc ⁇ O) refers to di-teri-butyldicarbonate.
  • pharmaceutically acceptable derivative refers to and includes any pharmaceutically acceptable salt, pro-drugs, metabolites, esters, ethers, hydrates, polymorphs, solvates, complexes or adducts of a compound described herein which, upon administration to a subject, is capable of providing (directly or indirectly) the parent compound.
  • antibacterial or a pharmaceutically acceptable derivative thereof includes all derivatives of the antibacterial agent (such as salt, prodrugs, metabolites, esters, ethers, hydrates, polymorphs, solvates, complexes or adducts) which, upon administration to a subject, is capable of providing (directly or indirectly) the antibacterial compound.
  • the compound of Formula (IV) is obtained by reacting a compound of Formula (II) with a compound of Formula (III) in presence of suitable coupling agent and in presence of suitable solvent.
  • suitable coupling agents include EDC hydrochloride, dicyclohexylcarbodiimide, diisopropylcarbodiimide (DIC), carbonyldiimidazole (CDI), pivalyl chloride, HOBt and the like.
  • compound of Formula (IV) is obtained by reacting a compound of Formula (II) with a compound of Formula (III) in presence of 1 -hydroxybenzotriazole (HOBt) and l-ethyl-3- (3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HC1) at temperature of about 25°C for about 16 hour. In some embodiments, this reaction is carried out in presence of mixture of water and dimethylformamide (DMF) as reaction solvent.
  • HOBt 1 -hydroxybenzotriazole
  • EDC.HC1 l-ethyl-3- (3-dimethylaminopropyl)carbodiimide hydrochloride
  • the compound of Formula (V) is obtained by hydrogeno lysis of a compound of a compound of Formula (IV).
  • the hydrogenolysis reaction can be carried out using a suitable hydrogenolysis agent.
  • hydrogenolysis of a compound of Formula (IV) to obtain a compound of Formula (V) is carried out in presence of a transition metal catalyst and a hydrogen source.
  • the transition metal catalyst is palladium on carbon
  • hydrogen source is hydrogen gas.
  • the hydrogenolysis reaction is carried out in presence of a suitable solvent such as dichlorome thane.
  • the hydrogenolysis of a compound of Formula (IV) is carried in presence 10% palladium on carbon and about 50 psi hydrogen atmosphere at a temperature of about 25°C for about 4 hour to obtain a compound of Formula (V).
  • the compound of Formula (VI) is obtained by sulfonating a compound of Formula (V), followed by treatment with tetrabutylammonium acetate.
  • the sulfonation reaction can be carried out in presence of suitable sulfonating agents such as sulfur trioxide pyridine complex, sulfur trioxide dimethylformamide complex and the like.
  • suitable sulfonating agents such as sulfur trioxide pyridine complex, sulfur trioxide dimethylformamide complex and the like.
  • the sulfonation of a compound of Formula (V) is carried out by action of sulfur trioxide-dimethylformamide complex (SO 3 -DMF) and in presence of dimethylformamide as solvent at temperature of about 10°C.
  • SO 3 -DMF sulfur trioxide-dimethylformamide complex
  • the sulfonation reaction is followed by treatment with tetrabutylammonium acetate to obtain a compound of Formula (VI).
  • the compound of Formula (VI) is converted to a compound of Formula (I) in presence of a suitable deprotecting reagent.
  • compound of Formula (VI) is converted to a compound of Formula (I) by reacting a compound of Formula (VI) with trifluoro acetic acid in presence of suitable solvent such as dichloromethane at temperature of about -10°C for about 1 hour.
  • compound of Formula (I) is prepared using a process described in Scheme 1.
  • compound of Formula (I) is further converted to its pharmaceutically acceptable derivative. In some embodiments, compound of Formula (I) is converted to its corresponding sodium salt.
  • a compound of Formula (I) in amorphous form there is provided a pharmaceutical composition comprising a compound of Formula (I) in amorphous form.
  • a compound of Formula (I) in crystalline form there is provided a pharmaceutical composition comprising a compound of Formula (I) in crystalline form.
  • a process for preparation of compound of Formula (I) in crystalline form comprising: (a) dissolving a compound of Formula (I) in water to obtain a homogeneous mixture; (b) adding isopropyl alcohol to the homogeneous mixture obtained in step (a); and (c) isolating a compound of Formula (I) in crystalline form.
  • a compound of Formula (I) having a purity of more than about 95% as determined by HPLC there is provided a pharmaceutical composition comprising a compound of Formula (I) having purity of more than about 95% as determined by HPLC.
  • L-hydroxyproline (VII) is decarboxylated by heating at higher temperature in presence of suitable catalyst such as 2-cyclohexen-l-one and in presence of suitable solvent such as cyclohexanol.
  • the decarboxylated product is isolated as hydrochloride salt of (3-(i?)-hydroxypyrrolidine hydrochloride) (VIII).
  • the compound of Formula (VIII) is reacted with di-feri-butyl dicarbonate [(Boc) 2 0] in presence of base such as triethylamine and in presence of catalyst such as 4-dimethylaminopyridine (DMAP) to obtain (3i?)-l-(ieri-butoxycarbonyl)-3-hydroxypyrrolidine (IX).
  • DMAP 4-dimethylaminopyridine
  • the compound of Formula (IX) is first reacted with the solution of diisopropyl azodicarboxylate and triphenylphosphine in suitable solvent under stirring, followed by reaction with N-hydroxyphthalamide to obtain (5)-3-[(l,3-dihydro-l,3-dioxo-isoindol-2- yl)oxy] -pyrrolidine- 1-carboxylic acid tert-buty ⁇ ester (X).
  • the compound of Formula (X) is reacted with hydrazine hydrate in suitable solvent such as dichloromethane to obtain feri-butyl-(35)-2-[(aminooxy) pyrrolidine- 1 -carboxylate of Formula (III).
  • a schematic for synthesis of a compound of Formula (III) is given in Scheme-2.
  • Step 2 Preparation of (3R)-l-(tert-butoxycarbonyl)-3-hydroxypyrrolidine (IX): To a stirred suspension of 3-(i?)-hydroxypyrrolidine hydrochloride (VIII) (110 g, 0.9 mol) in dichloromethane (1100 ml), triethylamine (273 g, 2.7 mol) was added at 0- 5°C. After 5 minute of stirring di-feri-butyldicarbonate [(Boc) 2 0] (245 g, 1.125 mol) was added to the reaction mixture in small portions, followed by 4-dimethylaminopyridine (10.99 g, 0.09 mol).
  • Step 3 Preparation of (5)-3-[(l,3-dihydro-l,3-dioxo-isoindol-2-yl)oxy]pyrrolidine-l- carbox lic acid tert- butyl ester (X):
  • N- hydroxy phthalimide (52.4 g, 0.3204mol) was added in one portion to the reaction mass.
  • the reaction mixture was allowed to warm to room temperature and stirred for 16 hour.
  • the completion of the reaction was monitored by thin layer chromatography.
  • the solvent was evaporated under reduced pressure.
  • the residue thus obtained was stirred with di-isopropyl ether (600 ml).
  • the precipitate formed was filtered under suction.
  • the filtrate was concentrated under reduced pressure and the residual mass was purified by silica gel (60-120 mesh) column chromatography using 1-5 % mixtures of acetone: hexane as an eluent.
  • Step 1 Preparation of fert-butyl-(35)-3-[( ⁇ [25, 5R)-6-(benzyloxy)-7-oxo-l,6- diazabicylco[3.2.1]oct-2-yl]carbonyl ⁇ amino)oxy]pyrrolidine-l-carboxylate (IV):
  • Step 3 Preparation of tert-butyl-(35)-3-[( ⁇ [25,5R)-6-(sulfooxy)-7-oxo-l,6- diazabicylco[3.2.1]oct-2-yl]carbonyl ⁇ amino)oxy]pyrrolidine-l-carboxylate, tetrabutyl ammonium salt (VI):
  • Step 4 Preparation of (25,5R)-7-oxo-iV-[(35)-pyrrolidin-2-yl-oxy]-6-(sulfooxy)-l,6- diazabicyclo [3.2.1]octane-2-carboxamide (I):
  • Typical X-ray analysis was performed as follows. Pass the test substance through sieve #100 BSS or gently grind it with a mortar and pestle. Place the test substance uniformly on a sample holder having cavity surface on one side, press the sample and cut into thin uniform film using a glass slide in such a way that the surface of the sample should be smooth and even. Record the X-ray diffractogram using the following instrument parameters.
  • Anti- scattering slit (Diffracted beam) 5.5 mm
  • Scan range 3 to 40°

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/IB2014/067382 2014-01-21 2014-12-29 A process for preparation of (2s, 5r)-7-oxo-n-[(3s)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo [3.2.1]octane-2-carboxamide WO2015110886A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111095082A (zh) * 2018-03-01 2020-05-01 依视路国际公司 镜片元件
CN112209865A (zh) * 2019-07-09 2021-01-12 中山澳达特罗生物科技有限公司 一种(R)-(-)-N-Boc-3-吡咯烷醇的生产方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5233053A (en) 1989-03-17 1993-08-03 Pfizer Inc. Pyrrolidine derivatives
WO2014033560A1 (en) * 2012-08-25 2014-03-06 Wockhardt Limited 1,6- diazabicyclo [3,2,1] octan- 7- one derivatives and their use in the treatment of bacterial infections
WO2014091268A1 (en) * 2012-12-11 2014-06-19 Naeja Pharmaceutical Inc. NEW BICYCLIC COMPOUNDS AND THEIR USE AS ANTIBACTERIAL AGENTS AND β-LACTAMASE INHIBITORS

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5233053A (en) 1989-03-17 1993-08-03 Pfizer Inc. Pyrrolidine derivatives
WO2014033560A1 (en) * 2012-08-25 2014-03-06 Wockhardt Limited 1,6- diazabicyclo [3,2,1] octan- 7- one derivatives and their use in the treatment of bacterial infections
WO2014091268A1 (en) * 2012-12-11 2014-06-19 Naeja Pharmaceutical Inc. NEW BICYCLIC COMPOUNDS AND THEIR USE AS ANTIBACTERIAL AGENTS AND β-LACTAMASE INHIBITORS

Non-Patent Citations (2)

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Title
CAIRA: "Crystalline Polymorphism of Organic Compounds", TOPICS IN CURRENT CHEMISTRY, SPRINGER, BERLIN, DE, vol. 198, 1 January 1998 (1998-01-01), pages 163 - 208, XP008166276, ISSN: 0340-1022 *
CHEMISTRY LETTERS, 1986, pages 893 - 896

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111095082A (zh) * 2018-03-01 2020-05-01 依视路国际公司 镜片元件
US11067832B2 (en) 2018-03-01 2021-07-20 Essilor International Lens element
CN111095082B (zh) * 2018-03-01 2021-11-30 依视路国际公司 镜片元件
US12158637B2 (en) 2018-03-01 2024-12-03 Essilor International Lens element
CN112209865A (zh) * 2019-07-09 2021-01-12 中山澳达特罗生物科技有限公司 一种(R)-(-)-N-Boc-3-吡咯烷醇的生产方法

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