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Umeclidinium bromide, ウメクリジニウム臭化物

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ChemSpider 2D Image | Umeclidinium bromide | C29H34BrNO2Umeclidinium bromide.png

Umeclidinium bromide

GSK-573719A, ウメクリジニウム臭化物

  • Molecular FormulaC29H34BrNO2
  • Average mass508.490 Da
1-[2-(Benzyloxy)ethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide
1-Azoniabicyclo[2.2.2]octane, 4-(hydroxydiphenylmethyl)-1-[2-(phenylmethoxy)ethyl]-, bromide (1:1)
diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide
7AN603V4JV
869113-09-7 [RN]
9551
GSK573719A; UNII-7AN603V4JV

Umeclidinium bromide (trade name Incruse Ellipta) is a long-acting muscarinic antagonist approved for the maintenance treatment of chronic obstructive pulmonary disease (COPD).[1] It is also approved for this indication in combination with vilanterol (as umeclidinium bromide/vilanterol).[2][3]

In the 2014, the drug was also approved in the E.U. and in the U.S. for the maintenance treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD). It was launched in the U.K. in October 2014 and in the U.S. in January 2015. In Japan, the product candidate was approved in 2015 as monotherapy for the maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD) and launched on October in the same year.

Image result for umeclidinium bromide synthesis

Umeclidinium bromide (Ellipta)
Umeclidinium bromide is a long-acting muscarinic acetylcholine antagonist developed by GlaxoSmithKline and approved by the US FDA at the end of 2013 for use in combination with vilanterol, a b2 agonist, for the treatment of chronic obstructive pulmonary disease.269 Due to umeclidinium’s poor oral bioavailability, the drug is administrated by inhalation as dry powder.269

The most likely scale preparation of the drug is described in Scheme .270
Commercially available ethyl isonipecotate (278) was alkylated with 1-bromo-2-chloroethane in the presence of K2CO3 in acetone to give ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (279). This material was then treated with lithium diisopropylamine (LDA) in THF to affect a transannular substitution reaction resulting in the cyclized quinuclidine 280 in 96% yield.270 Excess of phenyllithium was added to ester 280 in THF starting at low temperature then gradually warming to room temperature to give tertiary alcohol 281 in 61% yield. Amine 281 was finally alkylated with benzyl 2-bromoethyl ether (282) in MeCN/CHCl3 at elevated temperatures
to afford umeclidinium bromide (XXXV) in 69% yield.

269. Tal-Singer, R.; Cahn, A.; Mehta, R.; Preece, A.; Crater, G.; Kelleher, D.;Pouliquen, I. J. Eur. J. Pharmacol. 2013, 701, 40.
270. Laine, D. I.; McCleland, B.; Thomas, S.; Neipp, C.; Underwood, B.; Dufour, J.;Widdowson, K. L.; Palovich, M. R.; Blaney, F. E.; Foley, J. J.; Webb, E. F.;Luttmann, M. A.; Burman, M.; Belmonte, K.; Salmon, M. J. Med. Chem. 2009, 52, 2493.

FDA

https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ChemR.pdf

1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azoniabicyclo[2.2.2]octane bromide

PATENT

https://patents.google.com/patent/CN105461710A/en

umeclidinium bromide prepared patent US7439393, US RE44874, US 7488827, US 7498440, US7361787 and the like using phenyllithium prepared by reaction of intermediate 4 – [(diphenyl) hydroxymethyl] azabicyclo [2.2.2 ] octane.Specific methods: azabicyclo [2.2.2] octane-nucleophilic addition reaction with 4-carboxylate-fold amount of 2.02-2.5 phenyllithium occurs, the reaction temperature is controlled to -78 ° 0_15 ° C ο lithium Reagents expensive, difficult to store, use of harsh conditions, relatively high cost.

 Example 1

Phenyl magnesium chloride: Under nitrogen atmosphere to 55g (2.3mol) of metallic magnesium sandpaper lit with 3 L of tetrahydrofuran was added dropwise 215g (1.91mol) chlorobenzene, micro-thermal reaction proceeds, controlled dropping, the reaction was kept boiling, dropwise for about 1.5 hours, after the dropping was heated slightly under reflux for 30min. Cool reserve.

[0008] Example 2

Phenyl magnesium bromide: The under argon 50.4g (2.lmol) sandpaper lit magnesium metal with 4.2 liters of anhydrous ethyl ether was added a solution of 300g (1.91mol) of bromobenzene, was added an iodine initiator, electrical hair fever reaction proceeds, controlled dropping, the reaction was kept boiling, about 1.5 hours dropwise was added dropwise to a gentle reflux heated 30min. Cool reserve.

[0009] Example 3

Preparation of crude product: azabicyclo [2.2.2] octane-4-carboxylate (135g, 0.736mo 1) was dissolved in 3L of tetrahydrofuran, under nitrogen, was cooled to -5~0 ° C, was added dropwise 300g preparation of benzyl bromide Grignard reagent. After incubation -5~0 ° C stirred for 1 hour (progress of the reaction was monitored by TLC sample). Adding 50ml of water quenching. Liquid separation, the aqueous phase was extracted twice with 500ml of tetrahydrofuran, and the combined organic phases were washed with water, dried and filtered. The solvent was partially removed under reduced pressure, the balance maintaining approximately 1L, the residue was stirred overnight at 20 ° C crystallization.Filtered, washed (petroleum ether 2 X 200 ml), the filter cake was dried at 40 ° C in vacuo to give a yellowish white crystals 121.2 g, yield 54.2%.

[0010] Example 4

Preparation of crude product: azabicyclo [2.2.2] octane-4-carboxylate (18.3g, 0.lOmo 1) was dissolved in 3L of tetrahydrofuran, under nitrogen, was cooled to 0~5 ° C, was added dropwise 0.25 mol phenyl magnesium chloride. After incubation 0~5 ° C stirred for 1 hour (progress of the reaction was monitored by TLC sample) o quenched with 10ml of water was added. Liquid separation, the aqueous phase was extracted twice with 100ml of tetrahydrofuran, and the combined organic phases were washed with water, dried and filtered. The solvent was partially removed under reduced pressure, the balance maintaining approximately 50mL, the residue was stirred overnight at 20 ° C crystallization.Filtered, washed (petroleum ether 2X20 ml), the filter cake was dried at 40 ° C in vacuo to give a yellowish white crystals 14.63 g, yield 48.1%.

[0011] Example 5

Preparation of crude product: azabicyclo [2.2.2] octane-4-carboxylate (18.38,0.1011101) ^ 31 was dissolved in tetrahydrofuran, under nitrogen, was cooled to 5~15 ° C, was added dropwise 0.30 mol of benzene bromide. After incubation 5~15 ° C stirred for 1 hour (progress of the reaction was monitored by TLC sample) o quenched with 10ml of water was added. Liquid separation, the aqueous phase was extracted twice with 100ml of tetrahydrofuran, and the combined organic phases were washed with water, dried and filtered. The solvent was partially removed under reduced pressure, the balance maintaining approximately 50mL, the residue was stirred overnight at 20 ° C crystallization.Filtered, washed (petroleum ether 2 X 20 ml), the filter cake was dried at 40 ° C in vacuo to yield 13.80 g of yellow-white crystals, yield 47.1%.

[0012] Example 6

Umeclidinium bromide purification: 100g crude product was dissolved in 320ml of water to 80 ° C a mixture of 640ml of acetone, add 5g active carbon, and filtered.The filtrate was cooled to 25 ° C, for 1 hour. Within 1 to 2 hours and cooled to 0~5 ° C for 3 hours. The filter cake with chilled 1: 2 acetone – washed twice with water (2x20ml). The filter cake was dried in vacuo at 60 ° C to give white crystalline solid (92 g, yield 92%). Purity (HPLC normalization method) 99.25%.

[0013] Example 7

Umeclidinium bromide purification: 100g crude product was dissolved in 180ml water at 50 ° C a mixture of 360ml of acetone, add 5g active carbon, and filtered.The filtrate was ~ 2 hours to 25 ° C, for 1 hour. Within 1 to 2 hours cooled to 0 ° C and left overnight protection. The filter cake with chilled 1: 2 acetone – washed twice with water (2x20ml). The filter cake was dried at 60 ° C in vacuo to give fine (98.3 g, yield 98.3%). Purity (HPLC normalization method) 97.75%.

PATENT

https://patents.google.com/patent/WO2014027045A1

International Patent Publication Number WO 2005/104745 (Glaxo Group Limited), filed 27th April 2005, discloses muscarinic acetylcholine receptor antagonists. In particular, WO 2005/104745 discloses 4- [hydroxy(diphenyl)methyl]-l-{2-[(phenylmethyl)oxy]ethyl}-l-azoniabicyclo[2.2.2]octane bromide, of formula (I), and a process for the preparation of this compound (Example 84):

Figure imgf000002_0001

4-[Hydroxy(diphenyl)methyl]-l-{2-[(phenylmethyl)oxy]ethyl}-l-azoniabicyclo[2.2.2]octane bromide may also be referred to as umeclidinium bromide.

International Patent Publication Number WO 2011/029896 (Glaxo Group Limited), filed 10th September 2010, discloses an alternative preparation for an early intermediate, ethyl-l-azabicyclo[2.2.2] octane-4-carboxylate, in the multi-step synthesis of umeclidinium bromide.

There exists a need for an alternative process for the preparation of umeclidinium bromide. In particular, a process that offers advantages over those previously disclosed in WO 2005/104745 and WO 2011/029896 is desired. Advantages may include, but are not limited to, improvements in safety, control (i.e of final product form and physical characteristics), yield, operability, handling, scalability, and efficiency.

Summary of the Invention

The present invention provides, in a first aspect, a process for the preparation of umeclidinium bromide, which comprises: a) reacting ((2-bromoethoxy)methyl)benzene, of formula (II)

Figure imgf000003_0001

in a dipolar aprotic solvent with a boiling point greater than about 90°C or an alcohol with a boiling point greater than about 80°C; and optionally

b) re-crystallising the product of step (a).

The present invention is further directed to intermediates used in the preparation of the compound of formula (III), and hence of umeclidinium bromide. The process disclosed herein provides a number of advantages over prior art processes of WO 2005/104745 and WO 2011/029896.

PATENT

EP 3248970

FORM A B AND AMORPHOUS

https://patents.google.com/patent/EP3248970A1/en

The invention relates to novel solid forms of umeclidinium bromide (I), chemically 1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyclo[2.2.2]octane bromide. In particular, to its novel crystalline forms, identified as form A and form B, as well as to an amorphous form, and to their characterization by means of analytic methods. The invention further relates to methods of their preparation and their use for the preparation of umeclidinium bromide in the API quality.

Figure imgb0001

Umeclidinium bromide is indicated as an inhalation anticholinergic drug with an ultra-long-term effect in cooperating patients with the diagnosis of COPD (chronic obstructive pulmonary disease). COPD is defined as a preventable and treatable disease that is characterized by a persistent obstruction of air flow in the bronchi (bronchial obstruction), which usually progresses and is related to an intensified inflammatory response of the airways to harmful particles or gases. The main goal of the treatment of COPD is an improvement of the current control, i.e. elimination of symptoms, improvement of toleration of physical effort, improvement of the health condition and reduction of future risks, i.e. prevention and treatment of exacerbations, prevention of progression of the disease and mortality reduction

The structure of umeclidinium bromide, 1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyklo[2.2.2]octane bromide, is first mentioned in the general patent application WO2005009362 of 2003 .

Preparation of umeclidinium bromide is first disclosed in the patent EP 1 740 177B ( WO2005104745 ), where two methods (A and B) are mentioned, differing in the final processing and the product yield (method B included in Scheme 1). There, the last steps of the synthesis are described, the product being described by means of EI-MS, 1H NMR and elementary analysis. There is no information concerning the chemical purity or polymorphic form.

Figure imgb0002
Another preparation method of umeclidinium bromide is disclosed in the patent application WO 2014027045 , where three forms are also described (identified as forms 1 to 3), prepared using a method that is different from the procedure disclosed in the patent EP 1 740 177B .
    • Example 5

Preparation of the amorphous form of umeclidinium bromide

1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyclo[2.2.2]octane bromide (100 mg, 0.197 mmol, purity UPLC 98.89%) is dissolved at the temperature of 25°C in a water: tert-butanol mixture in the volume ratio of 6:4 (total 70 ml). The clear solution is freeze-dried (a bath with a mixture of dry ice and ethanol, -70°C) and lyophilized (vacuum: 1.8 Pa for 72 h). An amorphous form of umeclidinium bromide was obtained (100 mg). This amorphous form was confirmed with DSC and X-ray powder diffraction. The X-ray powder diffraction pattern is shown in Fig. 8 and the DSC record in Fig. 9.

PAPER

Synthetic Communications  An International Journal for Rapid Communication of Synthetic Organic Chemistry , Volume 48, 2018 – Issue 9, Convenient new synthesis of umeclidinium bromide

Pages 995-1000 | Received 05 Mar 2017, Accepted author version posted online: 10 Jul 2017, Published online: 10 Jul 2017

Umeclidinium bromide, a drug used for chronic obstructive pulmonary disease, is synthesized through a new intermediate of phenyl(quinuclidin-4-yl)methanone. This novel method with simple operation flow and cheap reagents, makes it suitable for scale up. The overall four-step process provides umeclidinium bromide in 29% yield and the purity up to 99.83%. The X-ray crystal structure of the drug molecule was first reported.

External links

References

  1. Jump up to:a b “Incruse Ellipta (umeclidinium inhalation powder) for Oral Inhalation Use. Full Prescribing Information” (PDF). GlaxoSmithKline, Research Triangle Park, NC 27709. Retrieved 22 February 2016.
  2. Jump up^ Feldman, GJ; Edin, A (2013). “The combination of umeclidinium bromide and vilanterol in the management of chronic obstructive pulmonary disease: Current evidence and future prospects”. Therapeutic advances in respiratory disease7 (6): 311–9. doi:10.1177/1753465813499789PMID 24004659.
  3. Jump up^ “FDA Approves Umeclidinium and Vilanterol Combo for COPD”. Medscape. December 18, 2013.
Umeclidinium bromide
Umeclidinium bromide.svg
Clinical data
Trade names Incruse Ellipta
Synonyms GSK573719A
License data
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Inhalation (DPI)
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding ~89%[1]
Metabolism Hepatic (CYP2D6)
Elimination half-life 11 hours
Excretion Feces (58%) and urine(22%)
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ChEBI
ECHA InfoCard 100.166.375 Edit this at Wikidata
Chemical and physical data
Formula C29H34BrNO2
Molar mass 508.49 g/mol
3D model (JSmol)

//////////////Umeclidinium bromide, Incruse Ellipta, ウメクリジニウム臭化物 , GSK573719A,  UNII-7AN603V4JV, FDA 2014

C1C[N+]2(CCC1(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)CCOCC5=CC=CC=C5.[Br-]

Synthesis

FDA Orange Book Patents: 1 of 15 (FDA Orange Book Patent ID)
Patent 9750726
Expiration Nov 29, 2030
Applicant GLAXOSMITHKLINE
Drug Application
  1. N203975 (Prescription Drug: ANORO ELLIPTA. Ingredients: UMECLIDINIUM BROMIDE
  2. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 2 of 15 (FDA Orange Book Patent ID)
Patent 6759398
Expiration Aug 3, 2021
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 3 of 15 (FDA Orange Book Patent ID)
Patent 7439393
Expiration May 21, 2025
Applicant GLAXOSMITHKLINE
Drug Application
  1. N203975 (Prescription Drug: ANORO ELLIPTA. Ingredients: UMECLIDINIUM BROMIDE
  2. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 4 of 15 (FDA Orange Book Patent ID)
Patent 7629335
Expiration Aug 3, 2021
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 5 of 15 (FDA Orange Book Patent ID)
Patent 7776895
Expiration Sep 11, 2022
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 6 of 15 (FDA Orange Book Patent ID)
Patent 8161968
Expiration Feb 5, 2028
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 7 of 15 (FDA Orange Book Patent ID)
Patent 8201556
Expiration Feb 5, 2029
Applicant GLAXO GRP ENGLAND
Drug Application N205382 (Prescription Drug: INCRUSE ELLIPTA . Ingredients: UMECLIDINIUM BROMIDE)
FDA Orange Book Patents: 8 of 15 (FDA Orange Book Patent ID)
Patent 6537983
Expiration Aug 3, 2021
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 9 of 15 (FDA Orange Book Patent ID)
Patent 7498440
Expiration Apr 27, 2025
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 10 of 15 (FDA Orange Book Patent ID)
Patent 7488827
Expiration Dec 18, 2027
Applicant GLAXOSMITHKLINE
Drug Application
  1. N203975 (Prescription Drug: ANORO ELLIPTA. Ingredients: UMECLIDINIUM BROMIDE
  2. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 11 of 15 (FDA Orange Book Patent ID)
Patent 8183257
Expiration Jul 27, 2025
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 12 of 15 (FDA Orange Book Patent ID)
Patent 6878698
Expiration Aug 3, 2021
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 13 of 15 (FDA Orange Book Patent ID)
Patent 8511304
Expiration Jun 14, 2027
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 14 of 15 (FDA Orange Book Patent ID)
Patent RE44874
Expiration Mar 23, 2023
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
FDA Orange Book Patents: 15 of 15 (FDA Orange Book Patent ID)
Patent 8309572
Expiration Apr 27, 2025
Applicant GLAXOSMITHKLINE
Drug Application
  1. N209482 (Prescription Drug: TRELEGY ELLIPTA. Ingredients: FLUTICASONE FUROATE
  2. UMECLIDINIUM BROMIDE
  3. VILANTEROL TRIFENATATE)
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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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