CH643567A5 - Verfahren zur herstellung einer kristallinen form von flunisolid. - Google Patents

Verfahren zur herstellung einer kristallinen form von flunisolid. Download PDF

Info

Publication number: CH643567A5
Authority: CH; Switzerland
Prior art keywords: flunisolide; solution; alkanol; water; added
Prior art date: 1979-05-21

Application number

CH393980A

Other languages

German (de)

English (en)

Inventor

Richard E Jones

Jacquelyn A Smithers

Original Assignee

Syntex Corp

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.)

1979-05-21

Filing date

1980-05-20

Publication date

1984-06-15

1980-05-20 Application filed by Syntex Corp filed Critical Syntex Corp

1984-06-15 Publication of CH643567A5 publication Critical patent/CH643567A5/de

Links

229960000676 flunisolide Drugs 0.000 title claims description 74
MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 title claims description 74
238000004519 manufacturing process Methods 0.000 title description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
238000002425 crystallisation Methods 0.000 claims description 16
230000008025 crystallization Effects 0.000 claims description 16
238000002441 X-ray diffraction Methods 0.000 claims description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
238000010586 diagram Methods 0.000 claims description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000007788 liquid Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 23
239000013078 crystal Substances 0.000 description 15
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
238000005169 Debye-Scherrer Methods 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000002002 slurry Substances 0.000 description 5
238000004090 dissolution Methods 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000007707 calorimetry Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000000386 microscopy Methods 0.000 description 2
238000001907 polarising light microscopy Methods 0.000 description 2
239000003380 propellant Substances 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
238000002076 thermal analysis method Methods 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
CQFNOACVVKSEOJ-VBQPQCOESA-N bronilide Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O CQFNOACVVKSEOJ-VBQPQCOESA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005443 coulometric titration Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960000442 flunisolide hemihydrate Drugs 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000004457 water analysis Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
- 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]

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH393980A 1979-05-21 1980-05-20 Verfahren zur herstellung einer kristallinen form von flunisolid. CH643567A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4083079A	1979-05-21	1979-05-21

Publications (1)

Publication Number	Publication Date
CH643567A5 true CH643567A5 (de)	1984-06-15

Family

ID=21913206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH393980A CH643567A5 (de)	1979-05-21	1980-05-20	Verfahren zur herstellung einer kristallinen form von flunisolid.

Country Status (17)

Country	Link
JP (1)	JPS55154997A (da)
AU (1)	AU532084B2 (da)
BE (1)	BE883381A (da)
CA (1)	CA1153761A (da)
CH (1)	CH643567A5 (da)
DE (1)	DE3019250C2 (da)
DK (1)	DK162530C (da)
FR (1)	FR2457303A1 (da)
GB (1)	GB2052506B (da)
HK (1)	HK40784A (da)
IL (1)	IL60128A (da)
IT (1)	IT1133092B (da)
MY (1)	MY8500694A (da)
NL (1)	NL189201C (da)
NZ (1)	NZ193778A (da)
SE (1)	SE431549B (da)
SG (1)	SG37585G (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1121513B (it) *	1979-05-28	1986-04-02	Chiesi Farma Spa	Processo per la conversione di umo steroide antiinfiammatorio in una forma suscettibile di essere somministarta come aerosol
GB8432063D0 (en)	1984-12-19	1985-01-30	Riker Laboratories Inc	Physically modified steroids

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX3864E (es) *	1975-05-27	1981-08-26	Syntex Corp	Un proceso para prepara el compuesto cristalino 6-fluiro-11b 21-dihiroxi-16 17-isopropilidendioxipregna-1 4-dien-3 20-diona

1980
- 1980-05-20 DK DK219280A patent/DK162530C/da not_active IP Right Cessation
- 1980-05-20 AU AU58566/80A patent/AU532084B2/en not_active Expired
- 1980-05-20 IT IT67791/80A patent/IT1133092B/it active Protection Beyond IP Right Term
- 1980-05-20 NZ NZ193778A patent/NZ193778A/xx unknown
- 1980-05-20 CH CH393980A patent/CH643567A5/de not_active IP Right Cessation
- 1980-05-20 JP JP6603580A patent/JPS55154997A/ja active Granted
- 1980-05-20 NL NLAANVRAGE8002902,A patent/NL189201C/xx not_active IP Right Cessation
- 1980-05-20 FR FR8011254A patent/FR2457303A1/fr active Granted
- 1980-05-20 IL IL60128A patent/IL60128A/xx unknown
- 1980-05-20 BE BE0/200678A patent/BE883381A/fr not_active IP Right Cessation
- 1980-05-20 SE SE8003761A patent/SE431549B/sv not_active IP Right Cessation
- 1980-05-20 GB GB8016683A patent/GB2052506B/en not_active Expired
- 1980-05-20 DE DE3019250A patent/DE3019250C2/de not_active Expired
- 1980-05-21 CA CA000352333A patent/CA1153761A/en not_active Expired
1984
- 1984-05-10 HK HK407/84A patent/HK40784A/xx not_active IP Right Cessation
1985
- 1985-05-18 SG SG375/85A patent/SG37585G/en unknown
- 1985-12-30 MY MY694/85A patent/MY8500694A/xx unknown

Also Published As

Publication number	Publication date
DE3019250C2 (de)	1982-11-11
FR2457303B1 (da)	1983-05-13
NL189201B (nl)	1992-09-01
NL8002902A (nl)	1980-11-25
IT1133092B (it)	1986-07-09
HK40784A (en)	1984-05-18
NL189201C (nl)	1993-02-01
MY8500694A (en)	1985-12-31
SG37585G (en)	1986-01-17
DK162530C (da)	1992-03-30
DK219280A (da)	1980-11-22
FR2457303A1 (fr)	1980-12-19
GB2052506B (en)	1983-01-19
IL60128A0 (en)	1980-07-31
IT8067791A0 (it)	1980-05-20
JPS55154997A (en)	1980-12-02
IL60128A (en)	1984-01-31
SE8003761L (sv)	1980-11-22
AU5856680A (en)	1980-11-27
JPS6258360B2 (da)	1987-12-05
DE3019250A1 (de)	1980-12-04
SE431549B (sv)	1984-02-13
CA1153761A (en)	1983-09-13
BE883381A (fr)	1980-11-20
AU532084B2 (en)	1983-09-15
GB2052506A (en)	1981-01-28
NZ193778A (en)	1982-03-16
DK162530B (da)	1991-11-11

Legal Events

Date	Code	Title	Description
2000-06-15	PL	Patent ceased

Publication	Publication Date	Title
DE2320111C2 (de)	1986-12-04	Beclomethasondipropionat, Betamethason-17-isobutyrat-21-acetat oder 21-Chlor-21-desoxybetamethason-17-propionat und deren Solvate mit einem Chlor- oder Chlorfluorkohlenwasserstoff mit 1 oder 2 Kohlenstoffatomen in einer besonderen kristallinen Form, Verfahren zu deren Herstellung und diese enthaltende Aerosolformulierungen
DE69217762T2 (de)	1997-10-09	Kristalle von N-(Trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanin und Verfahren zu ihrer Herstellung
EP0302948B1 (de)	1993-12-01	Verfahren zur Gewinnung von Steviosiden aus pflanzlichem Rohmaterial
DE60031882T2 (de)	2007-07-05	Verfahren zur herstellung von amorphem atorvastatin-calcium
DE3226224A1 (de)	1983-02-10	Verfahren zur isolierung von sterolen oder sterolmischungen
EP2024383A2 (de)	2009-02-18	Kristalline formen von 11beta-(4-acetylphenyl)-20,20,21,21,21-pentafluor-17alpha- hydroxy-19-nor-17 -pregna-4,9-dien-3-on
DE69828692T2 (de)	2006-01-12	Kristalline macrolide und verfahren zu ihrer herstellung
DE69917282T2 (de)	2005-05-25	Verfahren zur herstellung von zofenopril-calciumsalz
DE3018550C2 (de)	1982-07-15	Verfahren zur umwandlung eines entzuendungshemmenden steroids in eine zur verabreichung mit aerosol geeignete form
CH643567A5 (de)	1984-06-15	Verfahren zur herstellung einer kristallinen form von flunisolid.
DE3226225C2 (da)	1993-06-03
DE3336292C2 (da)	1992-09-10
DE68925355T2 (de)	1996-08-01	24r-scymnol, herstellung und verwendung
EP0508330B1 (de)	1995-08-16	Verfahren zur Herstellung von Extrakten aus Rhizoma Petasitidis mit Kohlendioxid
EP0374890A1 (de)	1990-06-27	Verfahren zur Herstellung von Anthrachinon-Derivaten
DE69734460T2 (de)	2006-07-06	Verfahren zur kristallisierung eines tetrahydropyridinderivates und die so erhaltenen kristallinen formen
DE2621222B2 (de)	1980-05-08	Verfahren zur Gewinnung von leicht resorbierbaren amorphen Sterylglukosidmonopalmitaten
CH644133A5 (de)	1984-07-13	Oxydierte sterylglycosid-derivate und sie enthaltende pharmazeutische praeparate.
DE68918122T2 (de)	1995-05-11	Verfahren zur Synthese von 5-alpha-Cholest-8(14)-en-3 beta-ol-15-on und andere 15-oxygenierte Sterine.
DE655404C (de)	1938-01-14	Verfahren zur Herstellung eines Esters des Pseudotropins
DE19842123C1 (de)	2000-07-13	11beta-Fluor-7alpha-(14,14,15,15,15-pentafluor-6- methyl-10-thia-6-azapentadecyl)estra-1,3,5(10)- trien-3,17beta-diol als kristallines Ansolvat
DE10035591A1 (de)	2002-01-31	Verfahren zur Isolierung von tetra-und pentacyclischen Triterpensäuren
DE69612626T2 (de)	2001-09-13	Hydrat-kristall und verfahren zu seiner herstellung
DE2138426A1 (de)	1972-02-17	Neue Steroide und Verfahren zu ihrer Herstellung
DE1815833C (de)	1971-05-27	Verfahren zur Verminderung der Vis kositat hochviskoser Celluloseather