IL117841A - Process for the preparation of pharmaceutical powder for inhalation - Google Patents
Process for the preparation of pharmaceutical powder for inhalationInfo
- Publication number
- IL117841A IL117841A IL11784196A IL11784196A IL117841A IL 117841 A IL117841 A IL 117841A IL 11784196 A IL11784196 A IL 11784196A IL 11784196 A IL11784196 A IL 11784196A IL 117841 A IL117841 A IL 117841A
- Authority
- IL
- Israel
- Prior art keywords
- solvent
- inhalation
- compound
- inhalation compound
- particles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 62
- 239000000843 powder Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title description 4
- 239000002245 particle Substances 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 239000012296 anti-solvent Substances 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 238000013019 agitation Methods 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- 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 claims description 15
- 229960004436 budesonide Drugs 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000003750 conditioning effect Effects 0.000 claims description 6
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000003172 expectorant agent Substances 0.000 claims description 4
- 229960002714 fluticasone Drugs 0.000 claims description 4
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 4
- 229960002848 formoterol Drugs 0.000 claims description 4
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 claims description 4
- 229950004432 rofleponide Drugs 0.000 claims description 4
- 229960002052 salbutamol Drugs 0.000 claims description 4
- 229960004017 salmeterol Drugs 0.000 claims description 4
- 229960000195 terbutaline Drugs 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 2
- 239000000043 antiallergic agent Substances 0.000 claims description 2
- 229940125715 antihistaminic agent Drugs 0.000 claims description 2
- 239000000739 antihistaminic agent Substances 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 229940124630 bronchodilator Drugs 0.000 claims description 2
- 239000000168 bronchodilator agent Substances 0.000 claims description 2
- 230000003419 expectorant effect Effects 0.000 claims description 2
- 229940066493 expectorants Drugs 0.000 claims description 2
- -1 glucocorticosteroids Substances 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 2
- 150000002617 leukotrienes Chemical class 0.000 claims description 2
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 230000000510 mucolytic effect Effects 0.000 claims description 2
- 229940066491 mucolytics Drugs 0.000 claims description 2
- 239000003358 phospholipase A2 inhibitor Substances 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- RATSWNOMCHFQGJ-TUYNVFRMSA-N (e)-but-2-enedioic acid;n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[[(2s)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1 RATSWNOMCHFQGJ-TUYNVFRMSA-N 0.000 claims 1
- 229960003610 formoterol fumarate dihydrate Drugs 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229960005018 salmeterol xinafoate Drugs 0.000 claims 1
- KFVSLSTULZVNPG-UHFFFAOYSA-N terbutaline sulfate Chemical compound [O-]S([O-])(=O)=O.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1 KFVSLSTULZVNPG-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 25
- 238000003756 stirring Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 8
- 239000005297 pyrex Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 230000002572 peristaltic effect Effects 0.000 description 4
- 210000002345 respiratory system Anatomy 0.000 description 4
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- NWLPAIVRIWBEIT-SEPHDYHBSA-N (e)-but-2-enedioic acid;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O NWLPAIVRIWBEIT-SEPHDYHBSA-N 0.000 description 2
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- JBRBWHCVRGURBA-UHFFFAOYSA-N broxaterol Chemical compound CC(C)(C)NCC(O)C1=CC(Br)=NO1 JBRBWHCVRGURBA-UHFFFAOYSA-N 0.000 description 2
- 229950008847 broxaterol Drugs 0.000 description 2
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- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 229960001022 fenoterol Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229950000339 xinafoate Drugs 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- NUBLQEKABJXICM-FQEVSTJZSA-N (1r)-1-(4-amino-3,5-dichlorophenyl)-2-[6-(2-pyridin-2-ylethoxy)hexylamino]ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1[C@@H](O)CNCCCCCCOCCC1=CC=CC=N1 NUBLQEKABJXICM-FQEVSTJZSA-N 0.000 description 1
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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- 238000000113 differential scanning calorimetry Methods 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- SYCWERNQGSKYAG-QVRIGTRMSA-N hydron;8-hydroxy-5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]-1h-quinolin-2-one;chloride Chemical compound Cl.C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 SYCWERNQGSKYAG-QVRIGTRMSA-N 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
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- QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960002720 reproterol Drugs 0.000 description 1
- WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 description 1
- 229960001457 rimiterol Drugs 0.000 description 1
- IYMMESGOJVNCKV-SKDRFNHKSA-N rimiterol Chemical compound C([C@@H]1[C@@H](O)C=2C=C(O)C(O)=CC=2)CCCN1 IYMMESGOJVNCKV-SKDRFNHKSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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|---|---|---|---|
| SE9501384A SE9501384D0 (sv) | 1995-04-13 | 1995-04-13 | Process for the preparation of respirable particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL117841A0 IL117841A0 (en) | 1996-08-04 |
| IL117841A true IL117841A (en) | 2004-01-04 |
Family
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|---|---|---|---|
| IL11784196A IL117841A (en) | 1995-04-13 | 1996-04-08 | Process for the preparation of pharmaceutical powder for inhalation |
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| EP (1) | EP0820276B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH11503448A (cg-RX-API-DMAC7.html) |
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| AR (1) | AR001624A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE230257T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU694863B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2217062A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69625589T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK0820276T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2188750T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL117841A (cg-RX-API-DMAC7.html) |
| IN (1) | IN185119B (cg-RX-API-DMAC7.html) |
| MY (1) | MY117344A (cg-RX-API-DMAC7.html) |
| NO (1) | NO316209B1 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ305515A (cg-RX-API-DMAC7.html) |
| PT (1) | PT820276E (cg-RX-API-DMAC7.html) |
| SA (1) | SA96160645B1 (cg-RX-API-DMAC7.html) |
| SE (1) | SE9501384D0 (cg-RX-API-DMAC7.html) |
| TW (1) | TW492877B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1996032095A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA962596B (cg-RX-API-DMAC7.html) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1282405C (en) | 1984-05-21 | 1991-04-02 | Michael R. Violante | Method for making uniformly sized particles from water-insoluble organic compounds |
| US4826689A (en) * | 1984-05-21 | 1989-05-02 | University Of Rochester | Method for making uniformly sized particles from water-insoluble organic compounds |
| EP0437451B1 (en) * | 1988-10-05 | 1993-06-09 | The Upjohn Company | Finely divided solid crystalline powders via precipitation into an anti-solvent |
| GB9001635D0 (en) * | 1990-01-24 | 1990-03-21 | Ganderton David | Aerosol carriers |
| JP3282731B2 (ja) * | 1990-06-15 | 2002-05-20 | メルク エンド カムパニー インコーポレーテッド | 結晶の構造および大きさを改良する結晶化方法 |
| SE9302777D0 (sv) * | 1993-08-27 | 1993-08-27 | Astra Ab | Process for conditioning substances |
| US5639441A (en) * | 1992-03-06 | 1997-06-17 | Board Of Regents Of University Of Colorado | Methods for fine particle formation |
| SE9501384D0 (sv) | 1995-04-13 | 1995-04-13 | Astra Ab | Process for the preparation of respirable particles |
-
1995
- 1995-04-13 SE SE9501384A patent/SE9501384D0/xx unknown
-
1996
- 1996-03-04 SA SA96160645A patent/SA96160645B1/ar unknown
- 1996-04-01 ZA ZA962596A patent/ZA962596B/xx unknown
- 1996-04-01 TW TW085103802A patent/TW492877B/zh not_active IP Right Cessation
- 1996-04-02 IN IN723DE1996 patent/IN185119B/en unknown
- 1996-04-08 IL IL11784196A patent/IL117841A/en active IP Right Grant
- 1996-04-12 CN CN96194372A patent/CN1102383C/zh not_active Expired - Fee Related
- 1996-04-12 JP JP8530963A patent/JPH11503448A/ja not_active Ceased
- 1996-04-12 PT PT96910285T patent/PT820276E/pt unknown
- 1996-04-12 AR AR33616796A patent/AR001624A1/es unknown
- 1996-04-12 DE DE69625589T patent/DE69625589T2/de not_active Revoked
- 1996-04-12 US US08/669,477 patent/US6221398B1/en not_active Expired - Fee Related
- 1996-04-12 EP EP96910285A patent/EP0820276B1/en not_active Revoked
- 1996-04-12 DK DK96910285T patent/DK0820276T3/da active
- 1996-04-12 WO PCT/SE1996/000479 patent/WO1996032095A1/en not_active Ceased
- 1996-04-12 ES ES96910285T patent/ES2188750T3/es not_active Expired - Lifetime
- 1996-04-12 AT AT96910285T patent/ATE230257T1/de not_active IP Right Cessation
- 1996-04-12 AU AU53524/96A patent/AU694863B2/en not_active Ceased
- 1996-04-12 CA CA002217062A patent/CA2217062A1/en not_active Abandoned
- 1996-04-12 NZ NZ305515A patent/NZ305515A/xx unknown
- 1996-04-13 MY MYPI96001419A patent/MY117344A/en unknown
-
1997
- 1997-10-02 NO NO19974557A patent/NO316209B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1102383C (zh) | 2003-03-05 |
| DK0820276T3 (da) | 2003-03-17 |
| CA2217062A1 (en) | 1996-10-17 |
| DE69625589T2 (de) | 2003-09-25 |
| IN185119B (cg-RX-API-DMAC7.html) | 2000-11-18 |
| MY117344A (en) | 2004-06-30 |
| AU5352496A (en) | 1996-10-30 |
| US6221398B1 (en) | 2001-04-24 |
| WO1996032095A1 (en) | 1996-10-17 |
| SE9501384D0 (sv) | 1995-04-13 |
| EP0820276B1 (en) | 2003-01-02 |
| ATE230257T1 (de) | 2003-01-15 |
| EP0820276A1 (en) | 1998-01-28 |
| ZA962596B (en) | 1996-10-14 |
| NO974557L (no) | 1997-10-02 |
| NO974557D0 (no) | 1997-10-02 |
| AU694863B2 (en) | 1998-07-30 |
| ES2188750T3 (es) | 2003-07-01 |
| CN1186428A (zh) | 1998-07-01 |
| SA96160645B1 (ar) | 2005-07-05 |
| AR001624A1 (es) | 1997-11-26 |
| TW492877B (en) | 2002-07-01 |
| DE69625589D1 (de) | 2003-02-06 |
| JPH11503448A (ja) | 1999-03-26 |
| NZ305515A (en) | 1999-03-29 |
| IL117841A0 (en) | 1996-08-04 |
| NO316209B1 (no) | 2003-12-29 |
| PT820276E (pt) | 2003-04-30 |
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