PT79320B - Process for the preparation of an occlusion compound of 2-nitroxymethyl-6-chloropyridine with beta-cyclodextrin - Google Patents

Process for the preparation of an occlusion compound of 2-nitroxymethyl-6-chloropyridine with beta-cyclodextrin Download PDF

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Publication number
PT79320B
PT79320B PT79320A PT7932084A PT79320B PT 79320 B PT79320 B PT 79320B PT 79320 A PT79320 A PT 79320A PT 7932084 A PT7932084 A PT 7932084A PT 79320 B PT79320 B PT 79320B
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Prior art keywords
nitroxymethyl
chloropyridine
cyclodextrin
occlusion
preparation
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PT79320A
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English (en)
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PT79320A (en
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Fujisawa Pharmaceutical Co
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Publication of PT79320A publication Critical patent/PT79320A/pt
Publication of PT79320B publication Critical patent/PT79320B/pt

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • 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
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Nanotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
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  • Crystallography & Structural Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Cardiology (AREA)
  • Plant Pathology (AREA)
  • Microbiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Pyridine Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Saccharide Compounds (AREA)

Description

Descrição do objecto do invento que
FUJISAWA PHARMACEUTICAL CO.,ITD japonesa, industrial, com sede em NP 3,4-chome, Doshomachi, Hi gashi-Ku, Osaka, Japão, pretende obter em Portugal, para: "PROCESSO PARA A PREPARAÇÃO DE UM COMPOSTO DE OCLUSÃO DE 2_NI_ TR0XXMETIL-6-CL0R0PIRIDINA COM P -CICLODEXTRINA".
0 presente invento refere-se a um proces Iso para a preparação de um composto de oclusão de 2_nitroximefcil-6-cloropiridina com ft-ciclopiridin.·.
A 2_nitroximetil-6-cloropiridina é um omposto que possui a fórmula estrutural apresentada a servir é útil como medicamento para o tratamento de perturbações asculares.
CH 0N0„ 2 2
Λ 2-nitroximetil-6~cloropiridina é uma lubstância oleosa e volátil. De uma maneira geral, é difícil /onverter esta substância numa preparação farmacêutica.
Como resultado do estudo intenso conduzi, o de modo a ultrapassar a dificuldade anteriormente referida, erificou-se que a dificuldade podia ser ultrapassada pela con
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versão de 2-nitroximetil-6-cloropiridina no sen composto tle oclusao comβ-ciclodextrina numa porporção molar de cerca de 1:1 ou cerca de 3:1.
Assim, o presente invento resolveu com sucesso não apenas o problema da formação de uma preparação em pó de 2-nitroximetil-A_cloropiridina mas também o problema de impedir a sua volatilização.
0 processo para a preparação do presente invento é efectuado por meio da reacção de 2_nitroximetil-6_ -cloropiridina Com fi-ciclodextrina.
0 processo de oclusão inclui diversas mo. dificações. Por exemplo, existem um processo para a preparação de um solvente, um processo que compreende a mistura do composto base e os compostos adicionais juntamente com uma pequena quantidade de um solvente, etc. Destes processos, o que se pre fere é o processo para a preparação do solvente que requer ape nas que se misturem ambos os compostos entre si num solvente apropriado. 0 composto de oclusão, tal como foi obtido, é isolado e purificado de uma maneira convencional. Por exemplo, quando se efectua a reacção de oclusão numa solução aquosa, o composto de oclusão, que ê levemente solúvel em água, c retirado por precipitação na mistura de reacção, Fode separar-se o precipitado por meio de um método convencional, por exemplo, por centrifugação. 0 produto assim separado pode ,ser purificado mediante lavagem com água, pelo que se retira afi -ciclodex trina solúvel em água ou a 2-nitroximetil-6-cloropiridina.
0 composto de oclusão obtido pelo proces
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so anteriormente descrito caracteriza-se por evitar a volatilização de 2_nitroximetil-6-cloropiridina. For exemplo, tal como é'tornado evidente pela Fig, 5, que apresenta a percenta-. gem da 2-nitroximetil-6-cloropiridina residual em função do tempo, 100% do composto de oclusão de 2-nitroximetil_6-cloro_ piridina- -ciclodextrina numa proporção molar de lí1 ou cerca de 87% de 2-nitroximetil_6_cloropiridina-p -ciclodextrina numa proporção molar de 3’·!, permanece depois de repousar durante 60 minutos enquanto que, com 2-nítroximetil-6-cloropiri. dina por si, a percentagem residual, após 60 minutos, é de 0%, Como se tornou evidente, a volatilização de 2-nitroximetil-6-oloropiridina é largamente evitada.
0s exemplos que se seguem são ainda representativos do processo para a preparação do presente inven to.
Exemplo 1
Em cada um de cinco tubos de centrifugação, dissolveram-se 600 mg de β -ciclodextrina em 20 ml de água destilada. Após a adição de Ç0, ICC, £00, 300 e 400 mg de
2-nitroximetil-6-cloropiridina aos cinco tubos de centrifugação, respectivamente, agitaram-se as misturas, centrífugaram_ -se e deixaram-se repousar durante a noite à temperatura ambiente para se completar a cristalização.
Recolheram-se os cristais por filtração, lavaram-se com água e secaram-se ao ar para proporcionarem um composto de oclusão de 2-nitroximetil-6-cloropiridina com β -ciclodextrina·
-3
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As condiçoes para a preparação do compos
to de oclusão de 2-.nitroximetil-6-eloropiridina com β -Ciclodextrina e as proporções molares que se verificarem nos produtos são apresentados no Quadro 1.
0 composto de oclusão obtido possui as seguintes caracteristicas físicas.
(i) No seu modelo de difracção de pó obtido por raio X, apresenta pontos máximos de cerca de 11,5°, cerca de 17,2° e cerca de 18,4°, que caracterizam um composto de oclusão de 2_nitroximetil-6-cloropiridina com β-ciclodextrina.
(ii) No seu espectro de absorção de infravermelhos (Nujol), apresenta absorções a 3300, 1645, 1586, 1568, 1459, 1376, 1 330, 1281, 1158, 1080, 1022, 1000, 940 e 842 cm"1
(iii) É levemente solúvel em água.
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por raios
e os seus
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Os modelos de difração de pó obtidos X destes produtos são apresentados nas Figuras 1 e 2 espectros de absorção de infravermelhos são apresenFiguras 3 e 4.
Breve descrição dos desenhos.
As Figuras 1 e 2 apresentam modelos de difracçao de pós dos compostos de oclusão obtidos no Exemplo 1 de acordo com o presente invento, nomeadamente os compostos de oclusão de 2_nitroximetil-6-cloropiridina com -ciclodextrina nos racios molares de 1:1 e 3:1, respectivamente, e as Figuras 3 e 4 apresentam espectros de absorção de infravermelhos dos compostos de oclusão de acordo com o presente invento nas proporções molares de 1:1 e de 3:1, respectivamente.
fi
A Figura 5 ilustra a influência da oclu sao na volatilização da 2-nitroximetil-6-cloropiridina.
0 depósito do primeiro pedido para o in vento acima descrito foi efectuado no Japão, em 11 de Outubro de 1983 sob ο N2. 190345/1983.
-

Claims (1)

  1. REIVINDICAÇÕES1?. _ Processo para a preparação de um composto de oclusão de 2_nitroximetil-6-cloropiridina com^ -ciclodextrina que compreende a reacção de 2_nitroximetil-6-cloropiridina com /? -ciclodextrina.
    23. - Processo de acordo com a reivindicação 1, caracterizado pelo facto de se incorporar uma solu
    55.780
    MES/ERU/8E-1254
    ção aquosa dina.
PT79320A 1983-10-11 1984-10-04 Process for the preparation of an occlusion compound of 2-nitroxymethyl-6-chloropyridine with beta-cyclodextrin PT79320B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58190345A JPS6081166A (ja) 1983-10-11 1983-10-11 ２−ニトロオキシメチル−６−クロロピリジンのβ−シクロデキストリン包接化合物およびその製造法

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PT79320A PT79320A (en) 1984-11-01
PT79320B true PT79320B (en) 1986-09-08

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PT79320A PT79320B (en) 1983-10-11 1984-10-04 Process for the preparation of an occlusion compound of 2-nitroxymethyl-6-chloropyridine with beta-cyclodextrin

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US (1) US4575548A (pt)
EP (1) EP0141300A3 (pt)
JP (1) JPS6081166A (pt)
KR (1) KR850003414A (pt)
CN (1) CN85102133A (pt)
AU (1) AU576521B2 (pt)
CA (1) CA1248523A (pt)
DK (1) DK461184A (pt)
ES (1) ES536654A0 (pt)
FI (1) FI843944L (pt)
GR (1) GR80531B (pt)
HU (1) HU194285B (pt)
IL (1) IL73076A (pt)
NO (1) NO843773L (pt)
OA (1) OA07832A (pt)
PH (1) PH20203A (pt)
PT (1) PT79320B (pt)
ZA (1) ZA847350B (pt)

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JPS6034156A (ja) * 1983-08-08 1985-02-21 Hayashibara Biochem Lab Inc エイコサペンタエン酸包接化合物及びこれを含有した飲食物
JPS60202115A (ja) * 1984-03-27 1985-10-12 Ichiro Shibauchi エポキシ樹脂用硬化剤
ZA885069B (en) * 1987-07-24 1989-03-29 Fujisawa Pharmaceutical Co Sustained-release percutaneous preparations
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
CA1321192C (en) * 1988-04-20 1993-08-10 Abdul Majid Inclusion complexes of cyclodextrins by agglomeration
US5997856A (en) * 1988-10-05 1999-12-07 Chiron Corporation Method and compositions for solubilization and stabilization of polypeptides, especially proteins
US20040014695A1 (en) * 1992-06-19 2004-01-22 Supergen, Inc. Pharmaceutical formulation
US5602112A (en) * 1992-06-19 1997-02-11 Supergen, Inc. Pharmaceutical formulation
US5824668A (en) * 1996-11-07 1998-10-20 Supergen, Inc. Formulation for administration of steroid compounds
EP1176792A1 (en) * 2000-07-24 2002-01-30 Alcatel Method and apparatus for providing an all digital loop with power-optimised mode
US20070010478A1 (en) * 2005-07-06 2007-01-11 Branimir Sikic Zosuquidar, daunorubicin, and cytarabine for the treatment of cancer
US20070009531A1 (en) * 2005-07-06 2007-01-11 Branimir Sikic Treatment of patients with cancer using a calicheamicin-antibody conjugate in combination with zosuquidar
US20070010486A1 (en) * 2005-07-06 2007-01-11 Jeff Schwegman Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins
US20070010485A1 (en) * 2005-07-06 2007-01-11 Jeff Schwegman Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins
US20070010487A1 (en) * 2005-07-06 2007-01-11 Jeff Schwegman Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins
US11812951B2 (en) 2008-06-17 2023-11-14 Apollo Endosurgery Us, Inc. Endoscopic needle assembly
US12108939B2 (en) 2008-06-17 2024-10-08 Boston Scientific Scimed, Inc. Endoscopic tissue grasping systems and methods
CA2692211C (en) * 2009-12-14 2011-09-13 Cellresin Technologies, Llc Maturation or ripening inhibitor release from polymer, fiber, film, sheet or packaging
GB2492284B (en) 2011-03-27 2013-07-17 Cellresin Tech Llc Cyclodextrin compositions, articles, and methods
US10182567B2 (en) 2011-03-27 2019-01-22 Cellresin Technologies, Llc Cyclodextrin compositions, articles, and methods
US9320288B2 (en) 2012-11-30 2016-04-26 Cellresin Technologies, Llc Controlled release compositions and methods of using
US9421793B2 (en) 2014-06-26 2016-08-23 Cellresin Technologies, Llc Electrostatic printing of cyclodextrin compositions

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US2959580A (en) * 1956-10-17 1960-11-08 Univ Minnesota Formation of inclusion compounds
CH445129A (fr) * 1964-04-29 1967-10-15 Nestle Sa Procédé pour la préparation de composés d'inclusion à poids moléculaire élevé
JPS56123912A (en) * 1980-03-05 1981-09-29 Nitto Electric Ind Co Ltd Drug-containing tape preparation
HU182217B (en) * 1980-10-17 1983-12-28 Chinoin Gyogyszer Es Vegyeszet Process for producing inclusive complexes of cyclodextrines and strong inorganic oxyacids
JPS57142962A (en) * 1981-02-28 1982-09-03 Santen Pharmaceut Co Ltd Cyclodextrin clathrate compound of sulfur-containing compound
JPS6054304B2 (ja) * 1981-10-16 1985-11-29 株式会社バコム ジソピラミド包接化合物
US4425336A (en) * 1982-05-24 1984-01-10 Key Pharmaceuticals, Inc. 3,4-Dihydroxy-N-[3-(4-dihydroxyphenyl)-1-methyl-n-propyl]-beta-phenethylamine cyclodextrin complexes
DK311683A (da) * 1982-07-26 1984-01-27 Fujisawa Pharmaceutical Co Fremgangsmaade til fremstilling af pyridylalkylnitratforbindelser
JPS6025967A (ja) * 1983-07-21 1985-02-08 Eisai Co Ltd トリパミド包接化合物
DE3329517A1 (de) * 1983-08-16 1985-02-28 Hoechst Ag, 6230 Frankfurt Einschlussverbindung von n,n-dimethyl-2-chlor-5-(3-methyl-2-(phenylimino)-4-thiazolin-4-yl)phenylsulfonamid, verfahren zu ihrer herstellung sowie pharmazeutische praeparate
DE3337802A1 (de) * 1983-10-18 1985-04-25 Merck Patent Gmbh, 6100 Darmstadt Pharmazeutische zubereitung

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IL73076A0 (en) 1984-12-31
CA1248523A (en) 1989-01-10
FI843944L (fi) 1985-04-12
ZA847350B (en) 1985-10-30
FI843944A0 (fi) 1984-10-08
ES8506758A1 (es) 1985-08-01
NO843773L (no) 1985-04-12
DK461184D0 (da) 1984-09-26
OA07832A (fr) 1986-11-20
HU194285B (en) 1988-01-28
PT79320A (en) 1984-11-01
EP0141300A3 (en) 1986-01-29
ES536654A0 (es) 1985-08-01
AU3339984A (en) 1985-04-18
JPS6245226B2 (pt) 1987-09-25
JPS6081166A (ja) 1985-05-09
IL73076A (en) 1988-05-31
HUT36832A (en) 1985-10-28
EP0141300A2 (en) 1985-05-15
DK461184A (da) 1985-04-12
GR80531B (en) 1985-01-09
US4575548A (en) 1986-03-11
AU576521B2 (en) 1988-09-01
PH20203A (en) 1986-10-20
KR850003414A (ko) 1985-06-17
CN85102133A (zh) 1987-01-17

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