NO321154B1 - Fremgangsmate ved fremstilling av mometason furoat - Google Patents

Fremgangsmate ved fremstilling av mometason furoat Download PDF

Info

Publication number: NO321154B1
Authority: NO; Norway
Prior art keywords: mometasone; reaction; furoate; solvent; furoyl chloride
Prior art date: 1999-08-02

Application number

NO19995225A

Other languages

English (en)

Norwegian (no)

Other versions

NO995225L (no

NO995225D0 (no

Inventor

William Heggie

Joao Bandarra

Original Assignee

Hovione Int Ltd

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.)

1999-08-02

Filing date

1999-10-26

Publication date

2006-03-27

1999-10-26 Application filed by Hovione Int Ltd filed Critical Hovione Int Ltd

1999-10-26 Publication of NO995225D0 publication Critical patent/NO995225D0/no

2001-02-05 Publication of NO995225L publication Critical patent/NO995225L/no

2006-03-27 Publication of NO321154B1 publication Critical patent/NO321154B1/no

Links

WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 title claims abstract description 17
229960002744 mometasone furoate Drugs 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 3
229960001664 mometasone Drugs 0.000 claims abstract description 9
QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims abstract description 9
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims abstract description 8
150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
239000012442 inert solvent Substances 0.000 claims abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 5
150000002085 enols Chemical class 0.000 claims description 2
239000003799 water insoluble solvent Substances 0.000 claims description 2
230000000717 retained effect Effects 0.000 claims 1
230000032050 esterification Effects 0.000 abstract description 4
238000005886 esterification reaction Methods 0.000 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000003610 charcoal Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
-1 trialkylsilyl ether Chemical compound 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical group OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Epidemiology (AREA)
Endocrinology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO19995225A 1999-08-02 1999-10-26 Fremgangsmate ved fremstilling av mometason furoat NO321154B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PT102343A PT102343B (pt)	1999-08-02	1999-08-02	Processo para a preparacao de furoato mometasona

Publications (3)

Publication Number	Publication Date
NO995225D0 NO995225D0 (no)	1999-10-26
NO995225L NO995225L (no)	2001-02-05
NO321154B1 true NO321154B1 (no)	2006-03-27

Family

ID=20085881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19995225A NO321154B1 (no)	1999-08-02	1999-10-26	Fremgangsmate ved fremstilling av mometason furoat

Country Status (22)

Country	Link
US (1)	US6177560B1 (es)
EP (1)	EP1074558B1 (es)
JP (1)	JP3746174B2 (es)
KR (1)	KR100640066B1 (es)
CN (1)	CN1149222C (es)
AT (1)	ATE229970T1 (es)
AU (1)	AU765592B2 (es)
CA (1)	CA2295455C (es)
DE (1)	DE69904585T2 (es)
DK (1)	DK1074558T3 (es)
ES (1)	ES2189354T3 (es)
HR (1)	HRP990341B1 (es)
HU (1)	HU227494B1 (es)
IL (1)	IL133752A (es)
NO (1)	NO321154B1 (es)
NZ (1)	NZ500555A (es)
PL (1)	PL191103B1 (es)
PT (1)	PT102343B (es)
RU (1)	RU2208616C2 (es)
SI (1)	SI1074558T1 (es)
UA (1)	UA60333C2 (es)
ZA (1)	ZA996758B (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20070099883A1 (en) *	2005-10-07	2007-05-03	Cheryl Lynn Calis	Anhydrous mometasone furoate formulation
EP1790754A1 (de) *	2005-11-24	2007-05-30	Siemens Aktiengesellschaft	Schichtsystem mit Gadolinium-Mischkristall-Pyrochlorphase
US8021742B2 (en) *	2006-12-15	2011-09-20	Siemens Energy, Inc.	Impact resistant thermal barrier coating system
US8815258B2 (en)	2009-05-29	2014-08-26	Pearl Therapeutics, Inc.	Compositions, methods and systems for respiratory delivery of two or more active agents
PL3106149T3 (pl)	2009-05-29	2020-06-01	Pearl Therapeutics, Inc.	Kompozycje do płucnego dostarczania długo-działających antagonistów muskarynowych i długo-działających agonistów receptora beta-2 adrenergicznego oraz powiązane sposoby i układy
PT105139B (pt) *	2010-06-01	2013-01-29	Hovione Farmaciencia S A	Método para a monofluorometilação de substratos orgânicos para preparação de compostos orgânicos biologicamente activos
ES2712988T5 (es)	2013-03-15	2022-10-21	Pearl Therapeutics Inc	Métodos y sistemas para acondicionamiento de materiales cristalinos en partículas
PE20160155A1 (es)	2013-05-22	2016-04-01	Pearl Therapeutics Inc	Composiciones, metodos y sistemas para el suministro por via respiratoria de tres o mas agentes activos
CN105481933B (zh) *	2015-12-25	2017-09-19	山东京卫制药有限公司	一种合成糠酸莫米松的方法
CN105566437B (zh) *	2015-12-30	2018-07-20	山东京卫制药有限公司	一种8dm衍生物及利用其合成糠酸莫米松的方法
CN107266518B (zh) *	2016-04-08	2021-03-30	天津金耀集团有限公司	一种糠酸莫米松晶型及其制备方法
TW202317079A (zh)	2021-07-09	2023-05-01	美商阿斯特捷利康有限責任公司	用於氣溶膠遞送之組合物、方法及系統
WO2023119093A1 (en)	2021-12-20	2023-06-29	Astrazeneca Ab	Compositions, methods and systems for aerosol drug delivery

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0057401B1 (en) *	1981-02-02	1984-08-01	Schering Corporation	Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them
SK283666B6 (sk) *	1996-06-28	2003-11-04	Schering Corporation	Spôsob prípravy 17-esterov 9alfa,21-dihalogén-pregnan- 11beta,17alfa-diol-20-ónov
US5886200A (en) *	1996-07-01	1999-03-23	Schering Corporation	Process for the preparation of 17-esters of 9 α, 21-dihalo-pregnane-11 β, 17 α-diol-20-ones

1999
- 1999-08-02 NZ NZ500555A patent/NZ500555A/xx not_active IP Right Cessation
- 1999-08-02 PT PT102343A patent/PT102343B/pt unknown
- 1999-10-21 HU HU9903747A patent/HU227494B1/hu unknown
- 1999-10-22 AU AU56024/99A patent/AU765592B2/en not_active Expired
- 1999-10-25 SI SI9930173T patent/SI1074558T1/xx unknown
- 1999-10-25 ES ES99308380T patent/ES2189354T3/es not_active Expired - Lifetime
- 1999-10-25 DE DE69904585T patent/DE69904585T2/de not_active Expired - Lifetime
- 1999-10-25 DK DK99308380T patent/DK1074558T3/da active
- 1999-10-25 AT AT99308380T patent/ATE229970T1/de active
- 1999-10-25 EP EP99308380A patent/EP1074558B1/en not_active Expired - Lifetime
- 1999-10-26 NO NO19995225A patent/NO321154B1/no not_active IP Right Cessation
- 1999-10-27 ZA ZA9906758A patent/ZA996758B/xx unknown
- 1999-11-03 KR KR1019990048285A patent/KR100640066B1/ko active IP Right Grant
- 1999-11-03 RU RU99123183/04A patent/RU2208616C2/ru active
- 1999-11-04 UA UA99116069A patent/UA60333C2/uk unknown
- 1999-11-05 JP JP31523699A patent/JP3746174B2/ja not_active Expired - Lifetime
- 1999-11-05 HR HR990341A patent/HRP990341B1/xx not_active IP Right Cessation
- 1999-11-05 PL PL336452A patent/PL191103B1/pl unknown
- 1999-11-26 CN CNB991243803A patent/CN1149222C/zh not_active Expired - Lifetime
- 1999-12-27 IL IL13375299A patent/IL133752A/en not_active IP Right Cessation
- 1999-12-29 US US09/476,004 patent/US6177560B1/en not_active Expired - Lifetime
2000
- 2000-01-14 CA CA002295455A patent/CA2295455C/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU5602499A (en)	2001-02-08
HUP9903747A3 (en)	2001-07-30
CA2295455A1 (en)	2001-02-02
KR20010020094A (ko)	2001-03-15
PL336452A1 (en)	2001-02-12
ZA996758B (en)	2000-08-30
EP1074558A1 (en)	2001-02-07
NZ500555A (en)	2000-11-24
CN1282744A (zh)	2001-02-07
PT102343A (pt)	2001-02-28
HUP9903747A2 (hu)	2001-05-28
CA2295455C (en)	2008-03-25
JP3746174B2 (ja)	2006-02-15
KR100640066B1 (ko)	2006-10-31
NO995225L (no)	2001-02-05
EP1074558B1 (en)	2002-12-18
CN1149222C (zh)	2004-05-12
SI1074558T1 (en)	2003-04-30
AU765592B2 (en)	2003-09-25
RU2208616C2 (ru)	2003-07-20
US6177560B1 (en)	2001-01-23
HU9903747D0 (en)	1999-12-28
JP2001048897A (ja)	2001-02-20
PL191103B1 (pl)	2006-03-31
IL133752A0 (en)	2001-04-30
NO995225D0 (no)	1999-10-26
ES2189354T3 (es)	2003-07-01
DE69904585D1 (de)	2003-01-30
HRP990341A2 (en)	2001-04-30
DK1074558T3 (da)	2003-04-07
IL133752A (en)	2004-02-19
ATE229970T1 (de)	2003-01-15
PT102343B (pt)	2003-11-28
UA60333C2 (uk)	2003-10-15
HRP990341B1 (en)	2003-10-31
HU227494B1 (en)	2011-07-28
DE69904585T2 (de)	2003-05-15

Legal Events

Date	Code	Title	Description
2019-11-04	MK1K	Patent expired

Publication	Publication Date	Title
NO321154B1 (no)	2006-03-27	Fremgangsmate ved fremstilling av mometason furoat
AU725606B2 (en)	2000-10-12	Process for the preparation of 17-esters of 9alpha,21- dihalo-pregnane-11beta,17alpha-diol-20-ones
CZ20023472A3 (cs)	2003-04-16	Způsob výroby meziproduktu
US4482706A (en)	1984-11-13	Steroid saponins
CN114957368A (zh)	2022-08-30	中间体化合物及其制备方法和应用
US20100331539A1 (en)	2010-12-30	Process for the preparation of pregnane derivatives
CN107629107B (zh)	2020-06-09	一种醋酸乌利司他的合成方法
US2705232A (en)	1955-03-29	Ternorcholanylthiazoles
MXPA00000670A (es)	2002-05-09	Proceso para la preparacion de furoato de mometasona
EP0240338B1 (en)	1990-07-04	Butenoic acid derivatives
CN115785188B (zh)	2024-06-07	一种布***的制备方法
JPS60181096A (ja)	1985-09-14	胆汁酸の精製方法
JP2547322B2 (ja)	1996-10-23	ブラシノステロイド化合物及びその製法
EP4384529A1 (en)	2024-06-19	Synthesis of delta 9,11 steroids
JP2631472B2 (ja)	1997-07-16	ブラシノステロイド誘導体及びその製造法
SU499810A3 (ru)	1976-01-15	Способ выделени -кето-2-дибензофуранмасл ной кислоты
JPH07267986A (ja)	1995-10-17	５α−コレスタ−８（１４）−エン−３β−オール−１５−オンおよび他の１５−酸素化ステロールの合成のための改良方法
JPH051053A (ja)	1993-01-08	６−（３−ジメチルアミノプロピオニル）フオルスコリンの新規製造法
PL201837B1 (pl)	2009-05-29	Związek 9-deoksy-9(Z)-hydroksyiminoerytromycyny A
JPH0146517B2 (es)	1989-10-09
JPH0739435B2 (ja)	1995-05-01	２４―オン―ブラシノステロイド誘導体
FR2689128A1 (fr)	1993-10-01	Procédé de préparation de l'acide alpha-méthyl 5-benzoyl 2-thiophène acétique optiquement actif et intermédiaires.
DD295856A5 (de)	1991-11-14	Verfahren zur herstellung von 21-acyloxy-pregna-1,4,16-trien-3,20-dion