LT3697B - Process for the manufacture of budesonide - Google Patents
Process for the manufacture of budesonide Download PDFInfo
- Publication number
- LT3697B LT3697B LTIP1729A LTIP1729A LT3697B LT 3697 B LT3697 B LT 3697B LT IP1729 A LTIP1729 A LT IP1729A LT IP1729 A LTIP1729 A LT IP1729A LT 3697 B LT3697 B LT 3697B
- Authority
- LT
- Lithuania
- Prior art keywords
- reaction
- budesonide
- methanol
- catalyst
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 title claims description 12
- 229960004436 budesonide Drugs 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- -1 naphtha Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 3
- SEKYBDYVXDAYPY-ILNISADRSA-N (8s,9s,10r,11s,13s,14s,16r,17s)-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 SEKYBDYVXDAYPY-ILNISADRSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GUSVXFPRNUPMFZ-ZEVBYOGFSA-N 16a-Hydroxyprednisolone Chemical compound C[C@]12C[C@@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1C[C@H](O)[C@]2(O)CC(O)=O GUSVXFPRNUPMFZ-ZEVBYOGFSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JXDZSEUDHVTGSK-UHFFFAOYSA-N acetonitrile butanal Chemical compound C(C)#N.C(CCC)=O JXDZSEUDHVTGSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0092—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by an OH group free esterified or etherified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Paper (AREA)
- Load-Bearing And Curtain Walls (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8903219A SE8903219D0 (sv) | 1989-10-02 | 1989-10-02 | Process for the manufacture of budesonide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1729A LTIP1729A (en) | 1995-07-25 |
| LT3697B true LT3697B (en) | 1996-02-26 |
Family
ID=20377019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1729A LT3697B (en) | 1989-10-02 | 1993-12-30 | Process for the manufacture of budesonide |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5556964A (de) |
| EP (1) | EP0494942B1 (de) |
| JP (1) | JP2965352B2 (de) |
| KR (1) | KR0160527B1 (de) |
| AT (1) | ATE130310T1 (de) |
| AU (1) | AU632864B2 (de) |
| BG (1) | BG61608B1 (de) |
| BR (1) | BR9007700A (de) |
| CA (1) | CA2065861C (de) |
| CY (1) | CY2084B1 (de) |
| DE (1) | DE69023664T2 (de) |
| DK (1) | DK0494942T3 (de) |
| ES (1) | ES2079491T3 (de) |
| FI (1) | FI103204B1 (de) |
| HK (1) | HK52097A (de) |
| HU (1) | HU212576B (de) |
| LT (1) | LT3697B (de) |
| LV (1) | LV10283B (de) |
| NO (1) | NO178827C (de) |
| RO (1) | RO110947B1 (de) |
| RU (1) | RU2048472C1 (de) |
| SE (1) | SE8903219D0 (de) |
| SG (1) | SG43344A1 (de) |
| UA (1) | UA26860C2 (de) |
| WO (1) | WO1991004984A1 (de) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6028190A (en) | 1994-02-01 | 2000-02-22 | The Regents Of The University Of California | Probes labeled with energy transfer coupled dyes |
| US6166024A (en) | 1995-03-30 | 2000-12-26 | Mayo Foundation For Medical Education And Research | Use of topical azathioprine and thioguanine to treat colorectal adenomas |
| IT1291288B1 (it) | 1997-04-30 | 1999-01-07 | Farmabios Srl | Processo per la preparazione di 16,17 acetali di derivati pregnanici con controllo della distribuzione epimerica al c-22. |
| SE9704186D0 (sv) * | 1997-11-14 | 1997-11-14 | Astra Ab | New composition of matter |
| US6266556B1 (en) | 1998-04-27 | 2001-07-24 | Beth Israel Deaconess Medical Center, Inc. | Method and apparatus for recording an electroencephalogram during transcranial magnetic stimulation |
| FR2782823B1 (fr) | 1998-09-01 | 2000-11-17 | Neopost Ind | Procede d'impression thermique |
| US6234167B1 (en) | 1998-10-14 | 2001-05-22 | Chrysalis Technologies, Incorporated | Aerosol generator and methods of making and using an aerosol generator |
| MY136453A (en) | 2000-04-27 | 2008-10-31 | Philip Morris Usa Inc | "improved method and apparatus for generating an aerosol" |
| US6883516B2 (en) | 2000-04-27 | 2005-04-26 | Chrysalis Technologies Incorporated | Method for generating an aerosol with a predetermined and/or substantially monodispersed particle size distribution |
| US6681998B2 (en) | 2000-12-22 | 2004-01-27 | Chrysalis Technologies Incorporated | Aerosol generator having inductive heater and method of use thereof |
| US7077130B2 (en) | 2000-12-22 | 2006-07-18 | Chrysalis Technologies Incorporated | Disposable inhaler system |
| US6701921B2 (en) | 2000-12-22 | 2004-03-09 | Chrysalis Technologies Incorporated | Aerosol generator having heater in multilayered composite and method of use thereof |
| US6491233B2 (en) | 2000-12-22 | 2002-12-10 | Chrysalis Technologies Incorporated | Vapor driven aerosol generator and method of use thereof |
| US6501052B2 (en) | 2000-12-22 | 2002-12-31 | Chrysalis Technologies Incorporated | Aerosol generator having multiple heating zones and methods of use thereof |
| US6799572B2 (en) | 2000-12-22 | 2004-10-05 | Chrysalis Technologies Incorporated | Disposable aerosol generator system and methods for administering the aerosol |
| US20030055026A1 (en) | 2001-04-17 | 2003-03-20 | Dey L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
| US6640050B2 (en) | 2001-09-21 | 2003-10-28 | Chrysalis Technologies Incorporated | Fluid vaporizing device having controlled temperature profile heater/capillary tube |
| US6568390B2 (en) | 2001-09-21 | 2003-05-27 | Chrysalis Technologies Incorporated | Dual capillary fluid vaporizing device |
| US6681769B2 (en) | 2001-12-06 | 2004-01-27 | Crysalis Technologies Incorporated | Aerosol generator having a multiple path heater arrangement and method of use thereof |
| US6804458B2 (en) | 2001-12-06 | 2004-10-12 | Chrysalis Technologies Incorporated | Aerosol generator having heater arranged to vaporize fluid in fluid passage between bonded layers of laminate |
| US6701922B2 (en) | 2001-12-20 | 2004-03-09 | Chrysalis Technologies Incorporated | Mouthpiece entrainment airflow control for aerosol generators |
| TWI359675B (en) | 2003-07-10 | 2012-03-11 | Dey L P | Bronchodilating β-agonist compositions |
| US7367334B2 (en) | 2003-08-27 | 2008-05-06 | Philip Morris Usa Inc. | Fluid vaporizing device having controlled temperature profile heater/capillary tube |
| US20070020299A1 (en) * | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid |
| US20070020196A1 (en) * | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid prepared from a unit dose suspension |
| US20070020298A1 (en) * | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether gamma-cyclodextrin and corticosteroid |
| WO2005088655A1 (en) * | 2004-03-12 | 2005-09-22 | The Provost Fellows And Scholars Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth Near Dublin | A magnetoresistive medium |
| US20070185066A1 (en) * | 2005-12-20 | 2007-08-09 | Verus Pharmaceuticals, Inc. | Systems and methods for the delivery of corticosteroids |
| US20070197486A1 (en) * | 2005-12-20 | 2007-08-23 | Verus Pharmaceuticals, Inc. | Methods and systems for the delivery of corticosteroids |
| US20070249572A1 (en) * | 2005-12-20 | 2007-10-25 | Verus Pharmaceuticals, Inc. | Systems and methods for the delivery of corticosteroids |
| US20070160542A1 (en) * | 2005-12-20 | 2007-07-12 | Verus Pharmaceuticals, Inc. | Methods and systems for the delivery of corticosteroids having an enhanced pharmacokinetic profile |
| JP2009526858A (ja) * | 2006-02-15 | 2009-07-23 | ティカ レーケメデル アーベー | コルチコステロイド溶液を製造する方法 |
| US12370352B2 (en) | 2007-06-28 | 2025-07-29 | Cydex Pharmaceuticals, Inc. | Nasal and ophthalmic delivery of aqueous corticosteroid solutions |
| CN102060906B (zh) * | 2010-12-23 | 2013-01-16 | 鲁南贝特制药有限公司 | 一种r布地奈德的制备方法 |
| EP3250211B1 (de) | 2015-01-30 | 2021-12-22 | Coral Drugs Pvt. Ltd. | Neuartiges verfahren zur herstellung von glucocorticoidsteroiden |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3197469A (en) * | 1958-08-06 | 1965-07-27 | Pharmaceutical Res Products In | 16, 17-acetals and ketals of 6-halo-16, 17-dihydroxy steroids of the pregnane seriesand intermediates therefor |
| US3077471A (en) * | 1961-08-04 | 1963-02-12 | Olin Mathieson | Steroids of the 19-norpregnane series |
| SE378109B (de) * | 1972-05-19 | 1975-08-18 | Bofors Ab | |
| SE8008524L (sv) * | 1980-12-04 | 1982-06-05 | Draco Ab | 4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand |
| IT1196142B (it) * | 1984-06-11 | 1988-11-10 | Sicor Spa | Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti |
| SE8604059D0 (sv) * | 1986-09-25 | 1986-09-25 | Astra Pharma Prod | A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives |
-
1989
- 1989-10-02 SE SE8903219A patent/SE8903219D0/xx unknown
-
1990
- 1990-09-27 WO PCT/SE1990/000619 patent/WO1991004984A1/en not_active Ceased
- 1990-09-27 DE DE69023664T patent/DE69023664T2/de not_active Expired - Lifetime
- 1990-09-27 JP JP2514161A patent/JP2965352B2/ja not_active Expired - Lifetime
- 1990-09-27 HU HU9201064A patent/HU212576B/hu unknown
- 1990-09-27 AU AU65309/90A patent/AU632864B2/en not_active Expired
- 1990-09-27 RO RO92-200446A patent/RO110947B1/ro unknown
- 1990-09-27 AT AT90915222T patent/ATE130310T1/de not_active IP Right Cessation
- 1990-09-27 KR KR1019920700728A patent/KR0160527B1/ko not_active Expired - Lifetime
- 1990-09-27 CA CA002065861A patent/CA2065861C/en not_active Expired - Lifetime
- 1990-09-27 EP EP90915222A patent/EP0494942B1/de not_active Expired - Lifetime
- 1990-09-27 UA UA94010159A patent/UA26860C2/uk unknown
- 1990-09-27 DK DK90915222.5T patent/DK0494942T3/da active
- 1990-09-27 BR BR909007700A patent/BR9007700A/pt not_active IP Right Cessation
- 1990-09-27 ES ES90915222T patent/ES2079491T3/es not_active Expired - Lifetime
- 1990-09-27 RU SU905011922A patent/RU2048472C1/ru active
- 1990-11-27 SG SG1996008769A patent/SG43344A1/en unknown
-
1992
- 1992-03-30 NO NO921233A patent/NO178827C/no not_active IP Right Cessation
- 1992-04-01 FI FI921426A patent/FI103204B1/fi active
- 1992-04-01 BG BG96166A patent/BG61608B1/bg unknown
-
1993
- 1993-06-30 LV LVP-93-858A patent/LV10283B/xx unknown
- 1993-12-30 LT LTIP1729A patent/LT3697B/lt not_active IP Right Cessation
-
1994
- 1994-12-16 US US08/357,773 patent/US5556964A/en not_active Expired - Lifetime
-
1997
- 1997-04-24 HK HK52097A patent/HK52097A/en not_active IP Right Cessation
-
1998
- 1998-10-16 CY CY9802084A patent/CY2084B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Expiry of a patent |
Effective date: 20131230 |