USRE44733E1 - 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block - Google Patents

6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block Download PDF

Info

Publication number
USRE44733E1
USRE44733E1 US13/432,742 US200013432742A USRE44733E US RE44733 E1 USRE44733 E1 US RE44733E1 US 200013432742 A US200013432742 A US 200013432742A US RE44733 E USRE44733 E US RE44733E
Authority
US
United States
Prior art keywords
per
cyclodextrin
deoxy
thio
pharmaceutically acceptable
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.)
Active, expires
Application number
US13/432,742
Other languages
English (en)
Inventor
Mingiang Zhang
Ronald Palin
Jonathan Bennett
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.)
Merck Sharp and Dohme BV
Original Assignee
Merck Sharp and Dohme BV
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8241767&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=USRE44733(E1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Merck Sharp and Dohme BV filed Critical Merck Sharp and Dohme BV
Priority to US13/432,742 priority Critical patent/USRE44733E1/en
Assigned to MERCK SHARP & DOHME B.V. reassignment MERCK SHARP & DOHME B.V. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: ORGANON BIOSCIENCES NEDERLAND B.V.
Assigned to ORGANON BIOSCIENCES NEDERLAND B.V. reassignment ORGANON BIOSCIENCES NEDERLAND B.V. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: MSD OSS B.V.
Application granted granted Critical
Publication of USRE44733E1 publication Critical patent/USRE44733E1/en
Active legal-status Critical Current
Adjusted expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A61K31/724—Cyclodextrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the invention relates to 6-mercapto-cyclodextrin derivatives, to their use for the preparation of a medicament for the reversal of drug-induced neuromuscular block, and to a kit for providing neuromuscular block and its reversal.
  • NMBA neuromuscular blocking agent
  • anaesthesia is routinely used during the administration of anaesthesia to facilitate endotracheal intubation and to allow surgical access to body cavities, in particular the abdomen and thorax, without hindrance from voluntary or reflex muscle movement.
  • NMBAs are also used in the care of critically-ill patients undergoing intensive therapy, to facilitate compliance with mechanical ventilation when sedation and analgesia alone have proved inadequate, and to prevent the violent muscle movements that are associated with electroconvulsive therapy treatment.
  • NMBAs are divided into two categories: depolarizing and non-depolarizing.
  • Depolarizing neuromuscular blocking agents bind to nicotinic acetylcholine receptors (nAChRs) at the neuromuscular junction in a way similar to that of the endogenous neurotransmitter acetylcholine. They stimulate an initial opening of the ion channel, producing contractions known as fasciculations.
  • nAChRs nicotinic acetylcholine receptors
  • Non-depolarizing neuromuscular blocking agents compete with acetylcholine for binding to muscle nAChRs, but unlike depolarizing NMBAs, they do not activate the channel. They block the activation of the channel by acetylcholine and hence prevent cell membrane depolarization, and as a result, the muscle will become flaccid. Most of the clinically-used NMBAs belong to the non-depolarizing category. These include tubocurarine, atracurium, (cis) atracurium, mivacurium, pancuronium, vecuronium, rocuronium and rapacuronium (Org 9487).
  • a reversal agent of NMBAs is often given to the patient to assist the recovery of muscle function.
  • Most commonly used reversal agents are inhibitors of acetylcholinesterase (AChE), such as neostigmine, edrophonium and pyridostigmine. Because the mechanism of action of these drugs is to increase the level of acetylcholine at the neuromuscular junction by inhibiting the breakdown of acetylcholine, they are not suitable for reversal of depolarizing NMBAs such as succinylcholine.
  • AChE acetylcholinesterase
  • AChE inhibitors as reversal agents leads to problems with selectivity, since neurotransmission to all synapses (both somatic and autonomic) involving the neurotransmitter acetylcholine is potentiated by these agents. This non-selectivity may lead to many side-effects due to the non-selective activation of muscarinic and nicotinic acetylcholine receptors, including bradycardia, hypotension, increased salivation, nausea, vomiting, abdominal cramps, diarrhoea and bronchoconstriction.
  • these agents can be used only after or together with the administration of atropine (or glycopyrrolate) to antagonize the muscarinic effects of acetylcholine at the muscarinic receptors in the autonomic parasympathetic neuro-effector junctions (e.g. the heart).
  • atropine or glycopyrrolate
  • mAChR muscarinic acetylcholine receptor
  • atropine causes a number of side-effects, e.g., tachycardia, dry mouth, blurred vision, difficulties in emptying the bladder and furthermore may affect cardiac conduction.
  • a further problem with anticholinesterase agents is that residual neuro-muscular activity must be present (>10% twitch activity) to allow the rapid recovery of neuromuscular function.
  • NMBAs can cause complete and prolonged block of neuromuscular function (“profound block”).
  • profound block At present, there is no reliable treatment to reverse such a ‘profound block’.
  • Attempts to overcome a ‘profound block’ with high doses of AChE inhibitors has the risk of inducing a “cholinergic crisis”, resulting in a broad range of symptoms related to enhanced stimulation of nicotinic and muscarinic receptors.
  • an AChE inhibitor and a mAChR antagonist e.g., atropine
  • the chemical chelators may further be safely employed for the reversal of ‘profound block’.
  • Examples of such chemical chelators as disclosed in EP 99,306,411, were selected from various classes of, mostly cyclic, organic compounds which are known for their ability to form inclusion complexes with various organic compounds in aqueous solution, e.g. cyclic oligosaccharides, cyclophanes, cyclic peptides, calixarenes, crown ethers and aza crown ethers.
  • cyclic molecules containing six or more ⁇ -D-glucopyranose units linked at the 1,4 positions by ⁇ -linkages as in amylose, and derivatives thereof were identified in EP 99306411 as particularly useful in the reversal of many of the commonly used neuromuscular blocking agents, or muscle relaxants, such as rocuronium, pancuronium, vecuronium, rapacuronium, mivacurium, atracurium, (cis) atracurium, succinylcholine and tubocurarine.
  • 6-mercapto-cyclodextrin derivatives do belong to the main aspect of the present invention which relates to the use of a 6-mercapto-cyclodextrin derivative according to the general formula I for the manufacture of a medicament for the reversal of drug-induced neuromuscular block.
  • the invention relates to 6-mercapto-cyclodextrin derivatives having the general formula I,
  • (C 1-6 )alkylene as used in the definition of formula I means a branched or straight chain bivalent carbon radical containing 1-6 carbon atoms, such as methylene, ethylene (1,2-ethandiyl), propylene (1-methyl-1,2-ethanediyl), 2-methyl-1,2-ethanediyl, 2,2-dimethyl-1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl and 1,6-hexanediyl.
  • phenylene means a bivalent moiety the free valencies of which can be positioned either ortho, meta or para to one another.
  • (C 1-3 )alkyl means a branched or straight chain alkyl group containing 1-3 carbon atoms, i.e. methyl, ethyl, propyl and isopropyl.
  • carboxyphenyl means a phenyl group which is substituted at either the ortho-, the meta- or the para-position with a carboxy-group.
  • the ortho-carboxyphenyl group is preferred.
  • 6-mercapto-cyclodextrin derivatives of the invention are particularly preferred.
  • the 6-mercapto-cyclodextrin derivatives of formula I can be prepared by reacting a C6-activated cyclodextrin derivative of formula II with an alkylthiol, arylalkylthiol or arylthiol derivative corresponding to H—S—R—X, wherein R and X have the meaning as previously defined, in the presence of an inorganic or organic base.
  • 6-mercapto-cyclodextrin derivatives of formula I can also be prepared by reacting a 6-thiol ⁇ - or ⁇ -cyclodextrin derivative of formula III with an alkylating agent, e.g., alkyl halide, arylalkyl halide, alkyl sulfonate, arylalkyl sulfonate, corresponding to Y—X—R, wherein Y, X and R have the meanings as previously defined, or with a double bond containing reagent, e.g., vinyl alkane, acrylate, etc., or an epoxide in the presence of an inorganic or organic base.
  • an alkylating agent e.g., alkyl halide, arylalkyl halide, alkyl sulfonate, arylalkyl sulfonate, corresponding to Y—X—R, wherein Y, X and R have the meanings as
  • salts of 6-mercapto-cyclodextrin derivatives of formula I wherein X represents the carboxylic acid group COOH, the sulphonic acid group SO 2 OH, the, phosphonic acid group PO(OH) 2 or the tetrazol-5-yl group may be obtained by treating the acid with an organic base or a mineral base, like sodium-, potassium- or lithium hydroxide.
  • the 6-mercapto-cyclodextrin derivatives, or pharmaceutically acceptable salts or solvates thereof, for use in the invention are administered parenterally.
  • the injection route can be intravenous, subcutaneous, intradermal, intramuscular, or intra-arterial.
  • the intravenous route is the preferred one.
  • the exact dose to be used will necessarily be dependent upon the needs of the individual subject to whom the medicament is being administered, the degree of muscular activity to be restored and the judgement of the anaesthetist/critical-care specialist.
  • Exfracorporal application of the chemical chelators of the invention for instance by mixing of the chemical chelator with the blood during dialysis or during plasmapheresis, is also contemplated.
  • kits for providing neuromuscular block and its reversal comprising (a) a neuromuscular blocking agent, and (b) a 6mercapto-cyclodextrin derivative according to general formula I capable of forming a guest-host complex with the neuromuscular blocking agent.
  • a kit according to the invention is meant a formulation, which contains separate pharmaceutical preparations, i.e. the neuromuscular blocking agent and a 6-mercapto-cyclodextrin derivative of formula I, i.e. the reversal agent.
  • the components of such a kit of parts are to be used sequentially, i.e.
  • the neuromuscular blocking agent and a 6-mercapto-cyclodextrin derivative of formula I i.e. the reversal agent.
  • the components of such a kit of parts are to be used sequentially, i.e. the neuromuscular blocking agent is administered to a subject in need thereof, which is followed, at a point in time when restoration of muscle function is required, by the administration of the reversal agent, i.e. a 6-mercapto-cyclodextrin derivative of the present invention.
  • a preferred kit contains a 6-mercapto-cyclodextrin derivative of formula I and a neuromuscular blocking agent which is selected from the group consisting of rocuronium, vecuronium, pancuronium, rapacuronium, mivacurium, atracurium, (cis)atracurium, tubocurarine and suxamethonium.
  • a particularly preferred kit of the invention comprises rocuronium as the neuromuscular blocking agent.
  • the 6-mercapto-cyclodextrin derivatives can be applied in the form of a solution, e.g. for use as an injection preparation.
  • the pharmaceutical composition may be presented in unit-dose or multi-dose containers, for example sealed vials and ampoules, and may be stored in a freeze dried (lyophilised) condition requiring only the addition of the sterile liquid carrier, for example, water prior to use.
  • the invention further includes a pharmaceutical formulation, as hereinbefore described, in combination with packaging material suitable for said composition, said packaging material including instructions for the use of the composition for the use as hereinbefore described.
  • Triphenylphosphine (30.1 g, 15 eq) was dissolved with stirring in dry DMF (160 ml). To this was added iodine (30.5 g, 15.6 eq) over 10 min. with heat evolved. Dry ⁇ -cyclodextrin (10 g, 7.7 mmol) was then added and the mixture was heated to 70° C. for 24 h. The mixture was allowed to cool, to which sodium methoxide (3.1 g sodium in 50 ml methanol) was added and the mixture was stirred for 30 min, before pouring onto methanol (800 ml) and evaporating to dryness.
  • sodium methoxide 3.1 g sodium in 50 ml methanol
  • the solution was poured into acetone (500 ml) and the precipitate was collected by filtration, dissolved in water (20 ml) and dialysed (MWCO 1000) by changing the external water four times. Internal solution was evaporated to low volume and poured into acetone (250 ml). The solid precipitate was collected by filtration and dried under vacuum at 70° C.
  • 3-Mercaptopropionic acid (1.22 ml, 14.0 mmol) was dissolved in dry DMF (45 ml) under N 2 at room temperature. To this solution was added in three portions sodium hydride (1.23 g, 30.8 mmol, 60%) and the mixture was stirred for a further 30 min. To this mixture was then added dropwise a solution of 6-per-deoxy6-per-iodo- ⁇ -cyclodextrin (3.12 g, 1.40 mmol) in 45 ml dry DMF. After addition, the reaction mixture was heated at 70° C. for 12 h.
  • Per-6-mercapto- ⁇ -cyclodextrin (1 g, 0.7 mmol; see example 17) was dissolved in DMF (10 ml) and stirring commenced at room temperature under a nitrogen atmosphere.
  • N-(2-Bromoethyl)phthalimide (1.57 g, 6.17 mmol) and caesium carbonate (2 g, 6.17 mmol) were added and the resultant suspension was stirred at 60° C. overnight under a nitrogen atmosphere. After cooling to room temperature the DMF was removed in vacuo and water (100 ml) was added with vigorous stirring. The precipitate was isolated by filtration, washed with water ( ⁇ 3) and dried in vacuo to yield 1.67 g of a cream solid.
  • the solid formed was collected by filtration, dissolved in water (500 ml) and dialysed (MWCO 1000) changing the external water four times.
  • the internal solution was evaporated to low volume and then re-crystallised from hot water to afford the title compound (8.5 g) as white cross-shaped crystals.
  • the solid formed was collected by filtration, dissolved in water (200 ml) and dialysed (MWCO 1000), changing the external water four times.
  • the internal solution was evaporated to low volume and poured onto ethanol (100 ml).
  • the precipitate was collected by filtration and dried under vacuum to afford the title compound (0.55 g) as a white solid.
  • mice Male Dunkin-Hartley guinea pigs (bodyweight: 600-900 g) were anaesthetized by i.p. administration of 10 mg/kg pentobarbitone and 1000 mg/kg urethane. After tracheotomy, the animals were artificially ventilated using a Harvard small animal ventilator. A catheter was placed into the carotid artery for continuous monitoring of arterial blood pressure and the taking of blood samples for blood gas analysis. Heart rate was derived from the blood pressure signal. The sciatic nerve was stimulated (rectangular pulses of 0.5 ms duration at 10 s (0.1 Hz) intervals at a supramaximal voltage, using a Grass S88 Stimulator) and the force of M.
  • gastrocnemius contractions was measured using a Grass FT03 force-displacement transducer. Contractions, blood pressure and heart rate were recorded on a multichannel Grass 7D recorder. Catheters were placed in both jugular veins. One catheter was used for the continuous infusion of a neuromuscular blocking agent. The infusion rate of the neuromuscular blocking agent was increased until a steady-state block of 85-90% was obtained. The other catheter was used for administration of increasing doses of the reversal agent. During continuous infusion of the neuromuscular blocking agent, single doses of increasing concentration of reversal agent were given.
US13/432,742 1999-11-29 2000-11-23 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block Active 2027-03-30 USRE44733E1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/432,742 USRE44733E1 (en) 1999-11-29 2000-11-23 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP99309558 1999-11-29
EP99309558 1999-11-29
PCT/EP2000/011789 WO2001040316A1 (en) 1999-11-29 2000-11-23 6-mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US10/148,307 US6670340B1 (en) 1999-11-29 2000-11-23 6-Mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US13/432,742 USRE44733E1 (en) 1999-11-29 2000-11-23 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block

Publications (1)

Publication Number Publication Date
USRE44733E1 true USRE44733E1 (en) 2014-01-28

Family

ID=8241767

Family Applications (3)

Application Number Title Priority Date Filing Date
US13/432,742 Active 2027-03-30 USRE44733E1 (en) 1999-11-29 2000-11-23 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US10/148,307 Ceased US6670340B1 (en) 1999-11-29 2000-11-23 6-Mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US10/603,355 Expired - Lifetime US6949527B2 (en) 1999-11-29 2003-06-23 6-Mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block

Family Applications After (2)

Application Number Title Priority Date Filing Date
US10/148,307 Ceased US6670340B1 (en) 1999-11-29 2000-11-23 6-Mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US10/603,355 Expired - Lifetime US6949527B2 (en) 1999-11-29 2003-06-23 6-Mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block

Country Status (34)

Country Link
US (3) USRE44733E1 (no)
EP (1) EP1259550B1 (no)
JP (2) JP3880041B2 (no)
KR (1) KR100716524B1 (no)
CN (1) CN1188428C (no)
AR (1) AR026605A1 (no)
AT (1) ATE288450T1 (no)
AU (1) AU776536B2 (no)
BE (1) BE2008C047I2 (no)
BR (1) BRPI0015947B8 (no)
CA (1) CA2390463C (no)
CO (1) CO5251450A1 (no)
CY (1) CY2008018I2 (no)
CZ (1) CZ298206B6 (no)
DE (2) DE122008000068I2 (no)
DK (1) DK1259550T3 (no)
ES (1) ES2237496T3 (no)
FR (1) FR08C0052I2 (no)
HK (1) HK1049489A1 (no)
HU (1) HU227451B1 (no)
IL (1) IL149423A0 (no)
LU (1) LU91501I2 (no)
MX (1) MXPA02004940A (no)
NL (1) NL300356I2 (no)
NO (2) NO328790B1 (no)
NZ (1) NZ518752A (no)
PE (1) PE20010902A1 (no)
PL (1) PL203012B1 (no)
PT (1) PT1259550E (no)
RU (1) RU2260013C2 (no)
SK (1) SK286282B6 (no)
TW (1) TWI242015B (no)
WO (1) WO2001040316A1 (no)
ZA (1) ZA200203538B (no)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019102009A1 (en) 2017-11-27 2019-05-31 Medichem, S.A. Process for the synthesis of a cyclodextrin derivative
US10385142B2 (en) 2017-01-23 2019-08-20 Scinopharm Taiwan, Ltd. Method for preparing sugammadex sodium
US10442871B2 (en) * 2017-06-22 2019-10-15 Lawrence Livermore National Security, Llc Modified cyclodextrins for the selective sequestration of fentanyl related compounds and uses thereof
US11097023B1 (en) 2020-07-02 2021-08-24 Par Pharmaceutical, Inc. Pre-filled syringe containing sugammadex
WO2021170304A1 (en) 2020-02-28 2021-09-02 Medichem, S.A. Method for drying sugammadex
US11446325B2 (en) * 2020-09-30 2022-09-20 Cyclolab Cyclodextrin Research And Development Laboratory Ltd. Cyclodextrin derivatives in the treatment or prevention of lysosomal neurodegenerative diseases
US11845811B2 (en) 2018-09-20 2023-12-19 Natco Pharma Limited Process for the preparation of Sugammadex sodium and its novel polymorphic form

Families Citing this family (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6744471B1 (en) * 1997-12-05 2004-06-01 Olympus Optical Co., Ltd Electronic camera that synthesizes two images taken under different exposures
TWI242015B (en) 1999-11-29 2005-10-21 Akzo Nobel Nv 6-mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
EP1629845A3 (en) * 2000-11-02 2006-03-22 Akzo Nobel N.V. Use of cortisol-sequestering agents for the treatment of hypercortisolaemia related disorders
CA2543443A1 (en) 2003-10-31 2005-05-12 The University Of Kansas Sulfoalkyl ether-alkyl ether cyclodextrin derivatives
EP1735326A4 (en) 2004-01-29 2011-04-20 Pinnacle Pharmaceuticals BETA-CYCLODEXTRIN DERIVATIVES AND THEIR USE AGAINST LETHAL TOXIN OF ANTHRAX
SI2708225T1 (sl) 2004-04-23 2019-05-31 Cydex Pharmaceuticals, Inc. Formulacija DPI, ki vsebuje sulfoalkil eter ciklodekstrin
WO2006083678A2 (en) 2005-01-28 2006-08-10 Pinnacle Pharmaceuticals, Inc. β-CYCLODEXTRIN DERIVATIVES AS ANTIBACTERIAL AGENTS
US7629331B2 (en) 2005-10-26 2009-12-08 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof
PL2335707T3 (pl) 2005-10-26 2015-10-30 Cydex Pharmaceuticals Inc Kompozycje eteru sulfoalkilowego cyklodekstryny i sposoby ich wytwarzania
US20090069412A1 (en) * 2007-09-09 2009-03-12 Protia, Llc Deuterium-enriched sugammadex
US7635773B2 (en) 2008-04-28 2009-12-22 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions
US7938283B2 (en) * 2008-06-20 2011-05-10 Grainpro, Inc. System and method for hermetic storage of agricultural commodities during shipping
WO2010053487A1 (en) 2008-11-07 2010-05-14 Cydex Pharmaceuticals, Inc. Composition containing sulfoalkyl ether cyclodextrin and latanoprost
CN101591402B (zh) * 2009-05-05 2011-11-30 杭州奥默医药技术有限公司 6-脱氧砜类环糊精衍生物及其制备方法
US8492538B1 (en) 2009-06-04 2013-07-23 Jose R. Matos Cyclodextrin derivative salts
DE102010012281A1 (de) * 2010-03-22 2011-09-22 Fresenius Medical Care Deutschland Gmbh Pharmazeutische Zusammensetzungen enthaltend substituiertes 6-Deoxy-6-sulfanylcyclodextrin
CN101864003B (zh) * 2010-06-11 2012-05-02 漆又毛 一种6-脱氧硫醚氨基酸环糊精衍生物的合成方法
ES2551585T3 (es) * 2010-08-25 2015-11-20 Davuluri, Ramamohan Rao Procedimiento mejorado para la preparación de Sugammadex
CN102060941B (zh) 2010-11-26 2012-12-26 漆又毛 6-脱氧α-氨基酸衍生物环糊精及制备和应用
CN104271605B (zh) 2012-02-15 2017-07-25 锡德克斯药物公司 环糊精衍生物的制造方法
RU2747757C2 (ru) 2012-02-28 2021-05-13 Сидекс Фармасьютикалс, Инк. Композиции алкилированного циклодекстрина и способы их получения и применения
JP5892847B2 (ja) * 2012-04-27 2016-03-23 Ｄｏｗａホールディングス株式会社 シクロデキストリンとシリカ含有物質との複合材料、及びその製造方法、並びにガス吸着剤
GB201211153D0 (en) * 2012-06-22 2012-08-08 Farmhispania Pharmaceutical compositions
MY181829A (en) 2012-10-22 2021-01-08 Cydex Pharmaceuticals Inc Alkylated cyclodextrin compositions and processes for preparing and using the same
WO2014125501A1 (en) 2013-02-14 2014-08-21 Neuland Laboratories Limited An improved process for preparation of sugammadex sodium
WO2015179963A1 (en) 2014-05-29 2015-12-03 Uti Limited Partnership Cyclodextrin-based polyanionic and non-ionic dendrimers
CN107073007A (zh) 2014-06-26 2017-08-18 丸石制药株式会社 具有改进的稳定性的罗库溴铵制剂
CN105348412B (zh) * 2014-08-22 2018-06-05 江苏恩华药业股份有限公司 一种舒更葡糖钠的纯化方法
JP6914188B2 (ja) 2014-08-22 2021-08-04 サイデックス・ファーマシューティカルズ・インコーポレイテッド 分画アルキル化シクロデキストリン組成物ならびにその調製方法および使用方法
MX2017011966A (es) 2015-03-19 2018-06-06 Cydex Pharmaceuticals Inc Composiciones que contienen silimarina y sulfoalquil eter ciclodextrina y metodos de uso de las mismas.
CN104844732B (zh) * 2015-03-27 2017-05-03 山东滨州智源生物科技有限公司 一种舒更葡糖钠的制备方法
AU2015390471A1 (en) * 2015-04-08 2017-11-09 John KLASSEN Pharmaceutical compositions of polyanionic and non-ionic cyclodextrin-based dendrimers and uses thereof
JP6946275B2 (ja) * 2015-05-29 2021-10-06 ラクシュミ・プラサド・アラパルティＬａｋｓｈｍｉ Ｐｒａｓａｄ ＡＬＡＰＡＲＴＨＩ スガマデクスおよびその中間体の製造方法
CN104922693A (zh) * 2015-06-19 2015-09-23 南开大学 一种阴离子型环糊精与抗癌药物包合物及制备方法
EP3359578A4 (en) * 2015-10-07 2019-05-15 UTI Limited Partnership MULTIFUNCTIONAL POLYANIONIC CYCLODEXTRIN DENDRIMERS
CN108291057B (zh) 2015-11-25 2021-07-13 费森尤斯卡比依普莎姆有限责任公司 全氯代-γ-环糊精的晶体形式
KR102251673B1 (ko) * 2015-11-25 2021-05-13 프레제니우스 카비 입섬 에스. 알. 엘. 슈감마덱스 및 이의 중간체 제조를 위한 개선된 방법
EP3733717A3 (en) 2016-03-22 2020-12-30 Fresenius Kabi iPSUM S.r.l. An improved process for the preparation of sugammadex
PT3448395T (pt) * 2016-04-29 2020-06-01 Alveron Pharma B V Ciclodextrinas como pró-coagulantes
ES2915423T3 (es) 2016-06-23 2022-06-22 Synthon Bv Proceso de preparación de sugammadex
US20180016359A1 (en) * 2016-06-29 2018-01-18 Beijing Creatron Institute Of Pharmaceutical Research Co., Ltd. Sugammadex preparation and purification method
US10526422B2 (en) 2016-06-29 2020-01-07 Beijing Creatron Institute Of Pharmaceutical Research Co., Ltd. Process for preparation and purification of Sugammades sodium
CN107778383B (zh) 2016-08-24 2020-03-10 王炳永 一种舒更葡糖钠的精制方法
US20180318249A1 (en) 2017-05-03 2018-11-08 Cydex Pharmaceuticals, Inc. Composition containing cyclodextrin and busulfan
CN109021148B (zh) * 2017-06-08 2020-11-10 天津科伦药物研究有限公司 一种制备舒更葡糖钠的方法
ES2761899T3 (es) 2017-06-30 2020-05-21 Synthon Bv Proceso para preparar Sugammadex
TWI703163B (zh) * 2017-08-23 2020-09-01 台耀化學股份有限公司 舒更葡糖鈉之製備方法及其晶型
US10233263B1 (en) * 2017-08-23 2019-03-19 Formosa Laboratories, Inc. Method for preparation of sugammadex sodium
CN107892727B (zh) * 2017-11-27 2019-12-24 合肥博思科创医药科技有限公司 一种舒更葡糖钠的纯化方法
EP3775026B1 (en) 2018-04-06 2022-03-16 Synthon B.V. Purification of sugammadex
KR102054228B1 (ko) 2018-05-28 2019-12-10 연성정밀화학(주) 슈가마덱스 나트륨염의 제조방법
MX2020013117A (es) * 2018-06-07 2021-02-18 Merck Sharp & Dohme Llc Procesos para la preparacion de sugammadex.
CN110615860A (zh) * 2018-06-20 2019-12-27 江苏恒瑞医药股份有限公司 一种舒更葡糖钠的纯化方法
EP3830184A1 (en) 2018-08-02 2021-06-09 Pliva Hrvatska D.O.O. Solid state forms of sugammadex sodium
CA3112872A1 (en) 2018-09-27 2020-04-02 Werthenstein Biopharma Gmbh Novel crystalline forms of sugammadex
JP6950966B2 (ja) * 2018-11-01 2021-10-13 丸石製薬株式会社 スガマデクス又はその薬理学的に許容される塩含有液剤及びその製造方法
CN109438591B (zh) * 2018-12-29 2021-02-09 博瑞生物医药（苏州）股份有限公司 舒更葡糖钠的制备工艺
CN109824800A (zh) * 2018-12-29 2019-05-31 鼎元(天津)生物医药科技有限公司 一种选择性肌松拮抗药舒更葡萄糖钠的制备方法
US20220169753A1 (en) 2019-03-29 2022-06-02 Hospira, Inc. An improved process for preparation of sugammadex acid and sugammadex sodium
CN111978435B (zh) 2019-05-22 2021-05-25 合肥博思科创医药科技有限公司 一种高纯度舒更葡糖钠的制备方法
US11324692B2 (en) 2019-07-03 2022-05-10 Galenicum Health S.L.U. Method to prepare pharmaceutical compositions of suggamadex
US20220273517A1 (en) 2019-08-30 2022-09-01 Terumo Kabushiki Kaisha Injection formulation
RU2724900C1 (ru) * 2019-10-24 2020-06-26 Маруиси Фармасьютикал Ко., Лтд. Препарат рокурония с улучшенной стабильностью
CN111019016B (zh) * 2019-12-27 2022-02-18 武汉嘉诺康医药技术有限公司 一种舒更葡糖钠杂质的合成方法
CN111714459B (zh) * 2020-06-18 2022-06-14 广州瑞尔医药科技有限公司 一种注射用舒更葡糖钠粉针剂及其制备方法
EP3932391A1 (en) 2020-07-03 2022-01-05 Galenicum Health S.L.U. Method to prepare pharmaceutical compositions
US11945788B2 (en) 2021-06-07 2024-04-02 Nuray Chemicals Private Limited Process for preparing pitolisant hydrochloride and solid-state forms thereof
CN113637097A (zh) * 2021-08-10 2021-11-12 北京恒创星远医药科技有限公司 6-全脱氧-6-全碘代-γ-环糊精晶体及其制备方法和应用
CN115708777A (zh) 2021-08-19 2023-02-24 北京费森尤斯卡比医药有限公司 包含巯基环糊精衍生物或其可药用盐的包装药品和保存方法

Citations (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3929813A (en) 1973-12-26 1975-12-30 Interx Research Corp Novel pro-drug derivatives of pyridinium aldoxime type cholinesterase reactivators and process for preparing same
US4599327A (en) 1982-12-03 1986-07-08 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt Dibenzo[bd]pyran derivatives, process for the preparation thereof and pharmaceutical compositions containing same
US4603123A (en) 1984-02-22 1986-07-29 Chiesi Farmaceutici, S.P.A. Compounds having antiinflammatory activity, obtained by complexation of piroxican with β-cyclodextrin, and pharmaceutical compositions containing them
EP0197571A2 (en) 1985-03-15 1986-10-15 Janssen Pharmaceutica N.V. Novel derivatives of gamma-cyclodextrin
US4727064A (en) 1984-04-25 1988-02-23 The United States Of America As Represented By The Department Of Health And Human Services Pharmaceutical preparations containing cyclodextrin derivatives
US4816462A (en) 1982-05-18 1989-03-28 Nowicky Wassili Method for diagnosing and for the therapeutic treatment of tumors and/or infectious diseases of different types with alkaloid-compounds
US4834985A (en) 1986-06-05 1989-05-30 Euroceltique S.A. Controlled release pharmaceutical composition
US4869904A (en) 1986-12-26 1989-09-26 Nisshin Flour Milling Co., Ltd. Sustained release drug preparation
US4983586A (en) 1987-12-30 1991-01-08 University Of Florida Pharmaceutical formulations for parenteral use
US4983636A (en) 1976-03-09 1991-01-08 Rikagaku Kenkyusho Wako Composition and method of treating selected malignant conditions
US5008386A (en) 1987-10-13 1991-04-16 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Methylated cyclodextrin type compounds and process for preparing same
US5017566A (en) 1987-12-30 1991-05-21 University Of Florida Redox systems for brain-targeted drug delivery
EP0447171A2 (en) 1990-03-15 1991-09-18 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
WO1992000331A1 (en) 1990-06-28 1992-01-09 The United States Of America, Represented By The Secretary, United States Department Of Commerce Regioselective substitutions in cyclodextrins
EP0465535A1 (en) 1989-04-03 1992-01-15 Janssen Pharmaceutica N.V. Regioselective substitutions in cyclodextrins
US5180716A (en) 1990-08-01 1993-01-19 The Regents Of The University Of California Cyclodextrin complexes for neuraxial administration of drugs
US5385891A (en) 1991-08-29 1995-01-31 Tanabe Seiyaku Co., Ltd. Polysulfate of β-cyclodextrin derivative and process for preparing the same
AU3662895A (en) 1994-11-04 1996-05-09 Commonwealth Scientific And Industrial Research Organisation Method for treating animals
WO1997017977A1 (en) * 1995-11-15 1997-05-22 Everest-Todd Research & Development Limited Topical compositions containing a beta-cyclodextrin and an amino polysaccharide
US5767112A (en) 1994-10-21 1998-06-16 Poli Industria Chimica, S.P.A. Muscle relaxant pharmaceutical compositions
US5834446A (en) * 1996-06-21 1998-11-10 Queen's University At Kingston Nerve process growth modulators
US5840881A (en) 1992-11-27 1998-11-24 Takeda Chemical Industries, Ltd. Composition containing a water-insoluble or slightly water-soluble compound with enhanced water-solubility
US5935941A (en) 1997-10-24 1999-08-10 Pitha; Josef Alkylations of cyclodextrins leading to derivatives which have a ridgidly extended cavity
JPH11246603A (ja) 1998-02-27 1999-09-14 Nippon Shokuhin Kako Co Ltd 新規シクロデキストリン誘導体及びその製造方法
WO2001012202A2 (en) 1999-08-13 2001-02-22 Akzo Nobel N.V. Use of chemical chelators as reversal agents for drug-induced neuromuscular block
WO2001040316A1 (en) 1999-11-29 2001-06-07 Akzo Nobel N.V. 6-mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US20020111377A1 (en) 2000-12-22 2002-08-15 Albany College Of Pharmacy Transdermal delivery of cannabinoids
US20020173550A1 (en) 1998-05-29 2002-11-21 Antonio Calignano Control of pain with endogenous cannabinoids
WO2004000832A1 (en) 2002-06-21 2003-12-31 Akzo Nobel N.V. 1-[(indol-3-yl)carbonyl] piperazine derivatives
US7026304B2 (en) 2001-02-14 2006-04-11 Akzo Nobel N.V. 2-alkylated-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block

Patent Citations (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3929813A (en) 1973-12-26 1975-12-30 Interx Research Corp Novel pro-drug derivatives of pyridinium aldoxime type cholinesterase reactivators and process for preparing same
US4983636A (en) 1976-03-09 1991-01-08 Rikagaku Kenkyusho Wako Composition and method of treating selected malignant conditions
US4816462A (en) 1982-05-18 1989-03-28 Nowicky Wassili Method for diagnosing and for the therapeutic treatment of tumors and/or infectious diseases of different types with alkaloid-compounds
US4599327A (en) 1982-12-03 1986-07-08 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt Dibenzo[bd]pyran derivatives, process for the preparation thereof and pharmaceutical compositions containing same
US4603123A (en) 1984-02-22 1986-07-29 Chiesi Farmaceutici, S.P.A. Compounds having antiinflammatory activity, obtained by complexation of piroxican with β-cyclodextrin, and pharmaceutical compositions containing them
US4727064A (en) 1984-04-25 1988-02-23 The United States Of America As Represented By The Department Of Health And Human Services Pharmaceutical preparations containing cyclodextrin derivatives
EP0197571A2 (en) 1985-03-15 1986-10-15 Janssen Pharmaceutica N.V. Novel derivatives of gamma-cyclodextrin
US4834985A (en) 1986-06-05 1989-05-30 Euroceltique S.A. Controlled release pharmaceutical composition
US4869904A (en) 1986-12-26 1989-09-26 Nisshin Flour Milling Co., Ltd. Sustained release drug preparation
US5008386A (en) 1987-10-13 1991-04-16 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Methylated cyclodextrin type compounds and process for preparing same
US4983586A (en) 1987-12-30 1991-01-08 University Of Florida Pharmaceutical formulations for parenteral use
US5002935A (en) 1987-12-30 1991-03-26 University Of Florida Improvements in redox systems for brain-targeted drug delivery
US5017566A (en) 1987-12-30 1991-05-21 University Of Florida Redox systems for brain-targeted drug delivery
EP0465535A1 (en) 1989-04-03 1992-01-15 Janssen Pharmaceutica N.V. Regioselective substitutions in cyclodextrins
EP0447171B1 (en) 1990-03-15 1994-11-02 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
US5250520A (en) * 1990-03-15 1993-10-05 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
EP0447171A2 (en) 1990-03-15 1991-09-18 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
WO1992000331A1 (en) 1990-06-28 1992-01-09 The United States Of America, Represented By The Secretary, United States Department Of Commerce Regioselective substitutions in cyclodextrins
US5180716A (en) 1990-08-01 1993-01-19 The Regents Of The University Of California Cyclodextrin complexes for neuraxial administration of drugs
US5385891A (en) 1991-08-29 1995-01-31 Tanabe Seiyaku Co., Ltd. Polysulfate of β-cyclodextrin derivative and process for preparing the same
US5840881A (en) 1992-11-27 1998-11-24 Takeda Chemical Industries, Ltd. Composition containing a water-insoluble or slightly water-soluble compound with enhanced water-solubility
US5767112A (en) 1994-10-21 1998-06-16 Poli Industria Chimica, S.P.A. Muscle relaxant pharmaceutical compositions
AU3662895A (en) 1994-11-04 1996-05-09 Commonwealth Scientific And Industrial Research Organisation Method for treating animals
WO1997017977A1 (en) * 1995-11-15 1997-05-22 Everest-Todd Research & Development Limited Topical compositions containing a beta-cyclodextrin and an amino polysaccharide
US5834446A (en) * 1996-06-21 1998-11-10 Queen's University At Kingston Nerve process growth modulators
US5935941A (en) 1997-10-24 1999-08-10 Pitha; Josef Alkylations of cyclodextrins leading to derivatives which have a ridgidly extended cavity
JPH11246603A (ja) 1998-02-27 1999-09-14 Nippon Shokuhin Kako Co Ltd 新規シクロデキストリン誘導体及びその製造方法
US20020173550A1 (en) 1998-05-29 2002-11-21 Antonio Calignano Control of pain with endogenous cannabinoids
WO2001012202A2 (en) 1999-08-13 2001-02-22 Akzo Nobel N.V. Use of chemical chelators as reversal agents for drug-induced neuromuscular block
US7265099B1 (en) 1999-08-13 2007-09-04 Organon N.V. Use of chemical chelators as reversal agents for drug-induced neuromuscular block
WO2001040316A1 (en) 1999-11-29 2001-06-07 Akzo Nobel N.V. 6-mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US6670340B1 (en) 1999-11-29 2003-12-30 Akzo Nobel 6-Mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US20040029833A1 (en) 1999-11-29 2004-02-12 Minggiang Zhang 6-Mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US6949527B2 (en) 1999-11-29 2005-09-27 Akzo Nobel N.V. 6-Mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US20020111377A1 (en) 2000-12-22 2002-08-15 Albany College Of Pharmacy Transdermal delivery of cannabinoids
US7026304B2 (en) 2001-02-14 2006-04-11 Akzo Nobel N.V. 2-alkylated-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
WO2004000832A1 (en) 2002-06-21 2003-12-31 Akzo Nobel N.V. 1-[(indol-3-yl)carbonyl] piperazine derivatives

Non-Patent Citations (56)

* Cited by examiner, † Cited by third party
Title
Adam, J. M., et. al; J. Med. Chem; Cyclodextrin-Derived Host Moleculaes as Reversal agents for the Neuromuscular Blocker Rocuronium Bromide: Synthesis and Structure-Activity Relationships, (2002), vol. 45, pp. 1806-1816.
Alvarez-Gomes, J.A., et al., "Reversal of vecuronium-induced shallow neuromuscular blockade is significantly faster with sugammadex compared with neostigmine", Eur. J. Anasthesiol, 2007; 24(Suppl 39); Abstract 9AP7-8.
Anderson, W.R., et al., "Brain-enhanced delivery of testosterone using a chemical delivery system complexed with 2-hydroxypropyl-b-cyclodextrin", 1997, Drug Design and Delivery, 2; 287-298.
AshtonP.R., et al., Chem. Eur. J., Synthetic Cyclic Oligosaccharides-Syntheses and Structural Properties of a Cyclo(1-4) . . . , (1986), vol. 2, No. 5, pp. 580-591.
Baer, et al., Carbohydrate Research, 280 (1996); Keptakis[6-S-(2,3-dihydroxypropyl)-6-thio] cyclomaltoheptaose and its sulfone: water-soluble B-cyclodextrin derivatives having modified polarity, pp. 315-321.
Baer, H. et al "Heptakis[6-S-(2,3-dihydroxypropyl)-6-thio]cyclomaltoheptaose . . ." Carbohyd. Res. (1996) vol. 280, pp. 315-321. *
Bisson, AP, et al., Che. Eur. J., "Cooperative Ineractions in a Ternary Mixture", (1998), vol. 4, No. 5, pp. 845-851.
Bom, A, et. al. , Angew Chem Int Ed; "A Novel Concept of Reversing Neuromuscular Block: Chemical Encapsulation of Rocuronium Bromide by a Cyclodextrin-Based Synthetic Host", (2002), vol. 41, No. 2,pp. 266-270.
Connors, K.A., Wiley Interscience, "Binding Constants. The measurement of molecular complex stability" (1987), New York, pp. 24-28.
Cram, D.J., et al., Am Chem Soc., "Macro Rings VIII. Aromatic Substitution of the (6,6) Paracyclophane", 1955, vol. 77, pp. 1179-1186.
Desire, B, et. al., Experientia; "Inactivation of sarin and soman by cyclodextrins in vitro", vol. 43, No. 4, (1987), pp. 395-397.
Desire, B. et al. "Interaction of Soman with □-Cyclodextrin1," Fundamental and Applied Toxicology, vol. 7, No. 4 (1986) pp. 646-657.
Escandar, G.M., Spectrofluorometric determination of piroxicam in the presence and absence of beta-cyclodextrin, vol. 124, No. 4, Feb. 1999, pp. 587-597: abstract medline.
Fielding, L., Determination of association constants (Ka) from Solution NMR Data, Tetrahedron 56 (2000) 6151-6170, May 2000.
Gattuso, G. et al. "Synthetic Cyclic Oligosaccharides," Chem. Rev. (1998) vol. 98, pp. 1919-1958.
Gennaro, A. R., et al., "Intravenous Admixtures" Chapter 85, Remington's Pharmaceutical Sciences, 18th Ed. Mack Publishing Company (1990) pp. 1545-1569.
Gennaro, A. R., et al., "Parental Preparations" Chapter 84, Remington's Pharmaceutical Sciences, 18th Ed. Mack Publishing Company (1990) pp. 1570-1580.
Golden, J. H. "Bi(anthracene-9,10-dimethylene) (Tetrabenzo-[2,2]-para-cyclophane].," J. Chem. Soc. (1961) pp. 3741-3748.
Guillo, et al., Bull. Chim. Soc. Fr., vol. 132, "Synthesis of Symmetrical cyclodextrin derivatives bearing multiple charges"; Jul. 4, 1995; pp. 857-866.
Guillo, F. et al "Synthesis of symmetrical cyclodextrin derivatives . . ." Bull. Soc. Chim. Fr. (1995) vol. 132, pp. 857-866. *
Hamelin, B., et al., American Chemical Society; 1995; "Formation of Highly Stable Heterodimers in Aquaeous Solution between B-Cyclodextrin Derivatives Bearing Multiple Opposite Charges"; 99, pp. 17877-17885.
Hamelin, et al., Formation of highly stable heterodimers in aqueous solution between B-cyclodextrin derivatives bearing opposite charges, J. Phys. Chem., vol. 99, No. 51, Aug. 1995.
Irie, T. et al. "Protective mechanism of □-cyclodextrin for the hemolysis induced with phenothiazine neuroleptics in vitro," J. Pharm. Dyn., vol. 6, No. 6 (1983) pp. 408-414.
Jicsinszky, L., et al., Comprehemsive Supramolecular Chemistry, vol. 3, Cyclodextrins, Elsevier Science Ltd., Oxford UK (1996) pp. 57-188.
Jones, RK, et al., "Reversal of Profound Rocuronium-induced Blockade with Sugammadex: A Rando . . .", Anesthesiology 2008: 109; 816-24.
Khan, A. R. et al. "Methods for Selective Modifications of Cyclodextrins," Chem. Rev. (1998) vol. 98, pp. 1977-1996.
Kuroda, et al; J. Chem. Soc. Perkin Trans, 1989; "Dynamic Molecular Motions of p-Methylcinnamic Acid included in B-Cyclodextrin Derivatives: A New Type of Free-energy Relationship in Complex Formation", pp. 1409-1416.
Kwak, et al, Determination of the binding of B-cyclodextrin derivatives to adamantine carboxylic acids using capillary electrophoresis, Chromatographia, vol. 43, No. 11/12, Dec. 1996.
Lee, C., et al., "Reversal of Profound Neuromuscular Block by Sugammadex Administered Three Minutes After Rocuronium", Anesthesiology, V. 110, No. 5, May 2009.
Lee, et al., Structure, Confirmation, and action of neuromuscular blocking drugs, British Journal of Anaesthesia, 87 (5): 755-69 (2001).
Lindberg, et. al., Carbohydrate Research,"Synthesis of some 2-0-(2-hydroxyalkyl) and 2-0-(2,3-di-hydroxyalkyl) derivatives of cyctomaltoheptaose", 22, 1991, pp. 113-119.
Loukas, Y. L., "Measurement of Molecular Association in Drug: Cyclodextrin Inclusion Complexes with Improved 1H NMR Studies," J. Pharm. Pharmacol (1997) vol. 49, pp. 944-948.
Luna et al., Isolation and characterization by NMR spectroscopy of three monosubstituted 4-sulfobutyl ether derivatives of cyclmaltoheptaose (B-cyclodrextrin), Carbohydrate Research 299 (1997), 111-118.
May, C. et al. "Development of a toxin-binding agent as a treatment for tunicaminyluracil toxicity: protection against tunicamycin poisoning of sheep," Australian Veterinary Journal, vol. 76, No. 11 (1998) pp. 752-756.
Miller et al., Sugammadex: An opportunity to change the practice of anesthesiology?, International Anesthesia Research Society, vol. 104, No. 3, Mar. 2007.
Miyake, M. et al. "Anionic Cyclophanes as Hosts for Cationic Aromatic Guests," Tetrahedron Letters, vol. 32, No. 49 (1991) pp. 7295-7298.
Miyake, M. et al. "Biomimetic Studies Using Artificial Systems. VI.1) Design and Synthesis of Novel Cyclophanes Having Eight Carboxyl Groups on the Aromatic Rings2)," Chem. Pharm. Bull., vol. 41(7) (1993) pp. 1211-1213.
PCT Search Report and Written Opinion for International Application No. PCT/EP00/11789 (WO2001/40316, corresponding to US6670340) dated Nov. 2, 2002; 4 pages.
Pitha, et al., Int'l Journal of Pharmaceutics, "Hydroxypropyl-B-Cyclodextrin: preparation and Characterization; effects on Solubility of Drugs", vol. 29, Issue 1, pp. 73-82 (1986).
Pitha, et al., Life Sciences, "Drug Solubilizers to Aid Pharmacologists: Amorphous Cyclodextrin Derivatives", 43: 492-502 (1988).
Richardson, JD; "Cannabinoids modulate pain by multiple mechanism of action", Journal of Pain 2000, vol. 1; No. 1; 2000; pp. 2-14.
Selected prosecution history of U.S. Appl. No. 10/049,393 (US7265099), including obviousness type double patenting rejection mailed Dec. 31, 2003, and applicant's response; and obviousness-type double patenting rejection mailed Aug. 7, 2006 and Applicant's response.
Selected prosecution history of U.S. Appl. No. 10/603,355 (US6,949,527), including obviousness type double patenting rejection mailed Feb. 8, 2005 and applicant's response filed Mar. 9, 2005.
Soga, T. et al. Modifications of Hydrophobic Cavity and their Effects on the Complex Formation with a Hydrophobic Substrate, Tetrahedron Letters, vol. 21 (1980) pp. 4351-4354.
Stella, V. J. et al. "Cyclodextrins: Their Future in Drug Formulation and Delivery," Pharmaceutical Research, vol. 14, No. 5 (1997), pp. 556-567.
Supplementary European Search Report dated Jul. 20, 2001, for related International Application No. PCT/EP00/076494.
Szente, L. et al. "Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development," Advanced Drug Delivery Reviews (1999) vol. 36, pp. 17-28.
Tarver, G. J. et al., 2-O-Substituted Cyclodextrins as Reversal Agents for the Neuromuscular Blocker Rocuronium Bromide, Bioorganic & Medicinal Chemistry (2002) vol. 10, pp. 1819-1827.
Tubashi, I, et al., Artificial Receptors for Amino Acids in Water. Local Environmental Effect on Polar Recognition by 6A,6B-dideoxy-6A,6B-bis(carboxymethylthiol)-B-Cyclodextrin, J. Am. Chem. Soc. 108, 4514-4518, 1986).
Uekama, K., et al., "Cyclodextrin Drug Carrier Systems", Chem Rev. (1998) vol. 98. pp. 2045-2076.
Uekama, K., et al., Effects of cyclodextrins on chlorpromazine-induced haemolysis and central nervous system responses:, J. Pharm. Pharmacol, vol. 33, No. 11 (1981), pp. 707-710.
Vogtle, et al. Comprehensive Supramolecular Chemistry, vol. 2, Molecular recognition: Receptors for molecular guests, Atwood et al. eds; Elsevier Science Ltd., Oxford, UK (1996) pp. 211-266.
Wenz, et al., "Synthesis of highly water-soluble cyclodextrin sulfonates by addition of hydrogen sulfite to cyclodextrin allyl ethers", Carbohydrate Research 322 (1999) 153-165.
Yaksh, T.L., et al., "Studies of pharmacology and pathology intrathecally administered 4-anilinopiperidine analogues and morphine in rat and cat," Anesthesiology, 64; 54-66. (1986).
Zarzycki, P.K., et al., The equilibrium constant of beta cyclodextrin-phenolphthalein complex: influence of temperature and tetrahydrofuran addition, vol. 18, No. 1-2, 1998, pp. 165-170.
Zhang, M.G, Drug-specific cyclodextrins: the future of rapid neuromuscular block reversal?: Drugs of the Future (2003), vol. 28, No. 4, pp. 347-354.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10385142B2 (en) 2017-01-23 2019-08-20 Scinopharm Taiwan, Ltd. Method for preparing sugammadex sodium
US10442871B2 (en) * 2017-06-22 2019-10-15 Lawrence Livermore National Security, Llc Modified cyclodextrins for the selective sequestration of fentanyl related compounds and uses thereof
WO2019102009A1 (en) 2017-11-27 2019-05-31 Medichem, S.A. Process for the synthesis of a cyclodextrin derivative
US11104746B2 (en) 2017-11-27 2021-08-31 Medichem, S.A. Process for the synthesis of a cyclodextrin derivative
US11845811B2 (en) 2018-09-20 2023-12-19 Natco Pharma Limited Process for the preparation of Sugammadex sodium and its novel polymorphic form
WO2021170304A1 (en) 2020-02-28 2021-09-02 Medichem, S.A. Method for drying sugammadex
US11097023B1 (en) 2020-07-02 2021-08-24 Par Pharmaceutical, Inc. Pre-filled syringe containing sugammadex
US11446325B2 (en) * 2020-09-30 2022-09-20 Cyclolab Cyclodextrin Research And Development Laboratory Ltd. Cyclodextrin derivatives in the treatment or prevention of lysosomal neurodegenerative diseases

Also Published As

Publication number Publication date
KR100716524B1 (ko) 2007-05-10
BRPI0015947A (pt) 2002-08-20
AU776536B2 (en) 2004-09-16
EP1259550A1 (en) 2002-11-27
DK1259550T3 (da) 2005-04-25
US6949527B2 (en) 2005-09-27
AU5438001A (en) 2001-06-12
SK286282B6 (sk) 2008-06-06
US20040029833A1 (en) 2004-02-12
PL356097A1 (en) 2004-06-14
CZ20021814A3 (cs) 2002-08-14
NO328790B1 (no) 2010-05-18
US6670340B1 (en) 2003-12-30
HUP0203755A3 (en) 2003-10-28
CZ298206B6 (cs) 2007-07-18
TWI242015B (en) 2005-10-21
BE2008C047I2 (no) 2019-12-11
MXPA02004940A (es) 2003-05-23
PE20010902A1 (es) 2001-09-06
JP2006348301A (ja) 2006-12-28
HUP0203755A2 (hu) 2003-04-28
JP2003515623A (ja) 2003-05-07
DE122008000068I1 (de) 2009-04-23
LU91501I9 (no) 2019-01-02
WO2001040316A1 (en) 2001-06-07
BRPI0015947B8 (pt) 2021-07-06
DE122008000068I2 (de) 2011-06-16
DE60017947T2 (de) 2005-06-23
JP4563972B2 (ja) 2010-10-20
NZ518752A (en) 2003-03-28
CO5251450A1 (es) 2003-02-28
HK1049489A1 (en) 2003-05-16
CY2008018I1 (el) 2009-11-04
CA2390463A1 (en) 2001-06-07
LU91501I2 (fr) 2009-01-26
CA2390463C (en) 2009-02-03
PT1259550E (pt) 2005-05-31
BRPI0015947B1 (pt) 2012-02-07
ATE288450T1 (de) 2005-02-15
FR08C0052I1 (no) 2009-02-27
NO20022522L (no) 2002-05-28
PL203012B1 (pl) 2009-08-31
FR08C0052I2 (fr) 2009-12-18
HU227451B1 (en) 2011-06-28
JP3880041B2 (ja) 2007-02-14
NO20022522D0 (no) 2002-05-28
AR026605A1 (es) 2003-02-19
NO2010019I1 (no) 2010-11-22
CY2008018I2 (el) 2009-11-04
SK7262002A3 (en) 2002-11-06
DE60017947D1 (de) 2005-03-10
EP1259550B1 (en) 2005-02-02
NL300356I1 (nl) 2008-10-01
NL300356I2 (nl) 2009-04-01
ES2237496T3 (es) 2005-08-01
IL149423A0 (en) 2002-11-10
KR20020063900A (ko) 2002-08-05
RU2260013C2 (ru) 2005-09-10
ZA200203538B (en) 2003-08-04
CN1402737A (zh) 2003-03-12
NO2010019I2 (no) 2012-08-27
CN1188428C (zh) 2005-02-09

Similar Documents

Publication Publication Date Title
USRE44733E1 (en) 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
US7026304B2 (en) 2-alkylated-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block
US20100075938A1 (en) Use of Chemical Chelators as Reversal Agents for Drug-Induced Neuromuscular Block
EA018959B1 (ru) Карбоксиэтилированные полисульфаты циклодекстрина, подходящие для применения в качестве лекарственных средств
HU226370B1 (en) Carbohydrate derivatives with antithrombotic activity and pharmaceutical compositions contg. them
US20110212907A1 (en) Hexadecasaccharides with antithrombotic activity, including a covalent bond and an amino chain

Legal Events

Date Code Title Description
AS Assignment

Owner name: ORGANON BIOSCIENCES NEDERLAND B.V., NETHERLANDS

Free format text: MERGER;ASSIGNOR:MSD OSS B.V.;REEL/FRAME:030824/0449

Effective date: 20130101

Owner name: MERCK SHARP & DOHME B.V., NETHERLANDS

Free format text: MERGER;ASSIGNOR:ORGANON BIOSCIENCES NEDERLAND B.V.;REEL/FRAME:030824/0642

Effective date: 20130102

FPAY Fee payment

Year of fee payment: 12

PTEF Application for a patent term extension

Free format text: PRODUCT NAME: BRIDION (SUGAMMADEX SODIUM); REQUESTED FOR 5 YEARS

Filing date: 20160210

Expiry date: 20210127