CN100404545C - Process for preparing crystalline ciclesonide with defined particle size - Google Patents
Process for preparing crystalline ciclesonide with defined particle size Download PDFInfo
- Publication number
- CN100404545C CN100404545C CNB2004800074813A CN200480007481A CN100404545C CN 100404545 C CN100404545 C CN 100404545C CN B2004800074813 A CNB2004800074813 A CN B2004800074813A CN 200480007481 A CN200480007481 A CN 200480007481A CN 100404545 C CN100404545 C CN 100404545C
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- Prior art keywords
- compound
- formula
- organic solvent
- epimer
- solvent
- 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.)
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- 239000002245 particle Substances 0.000 title claims abstract description 33
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 title abstract description 4
- 229960003728 ciclesonide Drugs 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 238000001556 precipitation Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- -1 cyclohexylmethylene Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 230000010933 acylation Effects 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 6
- 230000000699 topical effect Effects 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 8
- 230000002349 favourable effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000009826 distribution Methods 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000002050 international nonproprietary name Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 description 3
- 229960004436 budesonide Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006345 epimerization reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000013210 evaluation model Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 210000002850 nasal mucosa Anatomy 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- XUGISPSHIFXEHZ-UHFFFAOYSA-N 3beta-acetoxy-cholest-5-ene Natural products C1C=C2CC(OC(C)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XUGISPSHIFXEHZ-UHFFFAOYSA-N 0.000 description 1
- YEYCQJVCAMFWCO-UHFFFAOYSA-N 3beta-cholesteryl formate Natural products C1C=C2CC(OC=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 YEYCQJVCAMFWCO-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- CETKWEWBSMKADK-GSXVSZIWSA-N epostane Chemical compound C([C@]1(C)[C@@](C)(O)CC[C@H]1[C@@H]1CC2)C[C@@H]1[C@]1(C)[C@]32O[C@]3(C)C(O)=C(C#N)C1 CETKWEWBSMKADK-GSXVSZIWSA-N 0.000 description 1
- 229950002674 epostane Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001141 propulsive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Embodiment | Ethanol (ml/g) | The ethanol temperature (℃) | Water (ml/g) | Water temperature (℃) | Productive rate (%) | X 50 (μm) |
1 | 5 | RT | 25.5 | RT | 94 | 2.0 |
2 | 7.5 | RT | 25.5 | RT | 95 | 1.8 |
3 | 7.5 | RT | 12.5 | RT | 95-98 | 1.9 |
4 | 7.5 | RT | 7.5 | RT | 96 | 2.0 |
5 | 7.5 | RT | 12.5 | 10 | 94-96 | 1.6 |
6 | 7.5 | RT | 12.5 | 30 | 92-95 | 1.9 |
7 | 7 | RT | 10 | RT | 97 | 1.8 |
8 | 7 | RT | 12 | 40 | 97 | 1.8 |
9 | 6 | RT | 10 | 20 | 90-97 | 1.8 |
10 | 6 | RT | 6 | 20 | 97 | 2.0 |
11 | 2.2 | 50 | 6 | 20 | 96-98 | 1.8 |
12 | 2.2 | 50 | 10 | 20 | 96 | 2.8 |
13 | 3 | 40 | 7 | 20 | 96 | 2.1 |
14 | 4 | 30 | 8 | 20 | 96 | 1.8 |
15 | 4 | 30 | 8 | 30 | 96-97 | 1.9 |
16 | 10 | 20 | 10 | 20 | 97 | 1.9 |
Embodiment | Ethanol/water | X 50(μm) |
1 | 1/0.65 | 26.57 |
2 | 1/0.55 | 33.79 |
3 | 1/0.6 | 35.25 |
4 | 1/0.7 | 21.82 |
5 | 1/0.4 | 37.02 |
6 | 1/0.8 | 20.83 |
Claims (19)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03007007.2 | 2003-03-27 | ||
DE10314097.2 | 2003-03-27 | ||
EP03007007 | 2003-03-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1761678A CN1761678A (en) | 2006-04-19 |
CN100404545C true CN100404545C (en) | 2008-07-23 |
Family
ID=36707322
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800074813A Expired - Lifetime CN100404545C (en) | 2003-03-27 | 2004-03-26 | Process for preparing crystalline ciclesonide with defined particle size |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN100404545C (en) |
ZA (1) | ZA200506943B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106692115A (en) * | 2015-11-13 | 2017-05-24 | 天津金耀集团有限公司 | Ciclesonide suspension nasal spray composition |
CN106883283B (en) * | 2015-12-15 | 2021-02-02 | 天津金耀集团有限公司 | Ciclesonide monohydrate, crystal form and preparation method thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4605517A (en) * | 1983-10-29 | 1986-08-12 | Sterling Drug Inc. | Method of preparing steroid compounds of controlled particle size |
US5482934A (en) * | 1990-09-07 | 1996-01-09 | Especialidades Latinas Medicamentos Universales, S.A. (Elmu, S.A.) | Pregna-1,4-diene3,20-dione-16-17-acetal-21 esters, process for their preparation, composition, and methods for the treatment of inflammatory conditions |
CN1335787A (en) * | 1998-12-24 | 2002-02-13 | 葛兰素集团有限公司 | Apparatus and process for preparing crystalline particles |
WO2002038584A1 (en) * | 2000-11-10 | 2002-05-16 | Altana Pharma Ag | Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-dihydroxy-pregna-1,4-dien-3,20-dion or its 21-isobutyrat by transketalisation |
-
2004
- 2004-03-26 CN CNB2004800074813A patent/CN100404545C/en not_active Expired - Lifetime
-
2005
- 2005-08-30 ZA ZA200506943A patent/ZA200506943B/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4605517A (en) * | 1983-10-29 | 1986-08-12 | Sterling Drug Inc. | Method of preparing steroid compounds of controlled particle size |
US5482934A (en) * | 1990-09-07 | 1996-01-09 | Especialidades Latinas Medicamentos Universales, S.A. (Elmu, S.A.) | Pregna-1,4-diene3,20-dione-16-17-acetal-21 esters, process for their preparation, composition, and methods for the treatment of inflammatory conditions |
CN1335787A (en) * | 1998-12-24 | 2002-02-13 | 葛兰素集团有限公司 | Apparatus and process for preparing crystalline particles |
WO2002038584A1 (en) * | 2000-11-10 | 2002-05-16 | Altana Pharma Ag | Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-dihydroxy-pregna-1,4-dien-3,20-dion or its 21-isobutyrat by transketalisation |
Also Published As
Publication number | Publication date |
---|---|
CN1761678A (en) | 2006-04-19 |
ZA200506943B (en) | 2006-07-26 |
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