IL92457A - Drug aerosol preparations containing tetrafluoroethane - Google Patents

Drug aerosol preparations containing tetrafluoroethane

Info

Publication number: IL92457A
Authority: IL; Israel
Prior art keywords: formulation; medicament; aerosol; propellant; tetrafluoroethane
Prior art date: 1988-12-06

Application number

IL9245789A

Other languages

English (en)

Hebrew (he)

Other versions

IL92457A0 (en

Original Assignee

Riker Laboratories Inc

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.)

1988-12-06

Filing date

1989-11-27

Publication date

1994-10-21

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10648054&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL92457(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1989-11-27 Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc

1990-08-31 Publication of IL92457A0 publication Critical patent/IL92457A0/xx

1994-10-21 Publication of IL92457A publication Critical patent/IL92457A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 118
238000009472 formulation Methods 0.000 title claims abstract description 91
239000000443 aerosol Substances 0.000 title claims abstract description 62
239000003814 drug Substances 0.000 claims abstract description 47
239000004094 surface-active agent Substances 0.000 claims abstract description 29
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 27
150000001875 compounds Chemical class 0.000 claims abstract description 21
239000003380 propellant Substances 0.000 claims description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 32
-1 and 124 Chemical compound 0.000 claims description 21
235000019441 ethanol Nutrition 0.000 claims description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
229940079593 drug Drugs 0.000 claims description 16
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 16
CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 16
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical group CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 14
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229960002052 salbutamol Drugs 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
239000002245 particle Substances 0.000 claims description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 8
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 8
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 7
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 6
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
235000010445 lecithin Nutrition 0.000 claims description 6
239000000787 lecithin Substances 0.000 claims description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 6
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 6
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 5
VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 5
229940067606 lecithin Drugs 0.000 claims description 5
229960005414 pirbuterol Drugs 0.000 claims description 5
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 claims description 5
229960001457 rimiterol Drugs 0.000 claims description 5
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 4
229920001213 Polysorbate 20 Polymers 0.000 claims description 4
239000004147 Sorbitan trioleate Substances 0.000 claims description 4
229940092705 beclomethasone Drugs 0.000 claims description 4
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone 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)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
239000001282 iso-butane Substances 0.000 claims description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
235000019337 sorbitan trioleate Nutrition 0.000 claims description 4
229960000391 sorbitan trioleate Drugs 0.000 claims description 4
UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 3
NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 3
BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 claims description 3
239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 3
RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 3
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone 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)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 3
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
229950000210 beclometasone dipropionate Drugs 0.000 claims description 3
239000001273 butane Substances 0.000 claims description 3
229960000541 cetyl alcohol Drugs 0.000 claims description 3
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 3
229960001927 cetylpyridinium chloride Drugs 0.000 claims description 3
239000002285 corn oil Substances 0.000 claims description 3
235000005687 corn oil Nutrition 0.000 claims description 3
229960000265 cromoglicic acid Drugs 0.000 claims description 3
JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 claims description 3
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 3
229940093471 ethyl oleate Drugs 0.000 claims description 3
229940068939 glyceryl monolaurate Drugs 0.000 claims description 3
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 3
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 3
239000003921 oil Substances 0.000 claims description 3
235000019198 oils Nutrition 0.000 claims description 3
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000001294 propane Substances 0.000 claims description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
HDIFHQMREAYYJW-FMIVXFBMSA-N 2,3-dihydroxypropyl (e)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C\CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-FMIVXFBMSA-N 0.000 claims description 2
HJRDNARELSKHEF-CLFAGFIQSA-N 2-[2-[(z)-octadec-9-enoyl]oxyethoxy]ethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOCCOC(=O)CCCCCCC\C=C/CCCCCCCC HJRDNARELSKHEF-CLFAGFIQSA-N 0.000 claims description 2
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 2
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
230000003444 anaesthetic effect Effects 0.000 claims description 2
229920001400 block copolymer Polymers 0.000 claims description 2
239000002385 cottonseed oil Substances 0.000 claims description 2
235000012343 cottonseed oil Nutrition 0.000 claims description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229940075507 glyceryl monostearate Drugs 0.000 claims description 2
229940074928 isopropyl myristate Drugs 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
239000004006 olive oil Substances 0.000 claims description 2
235000008390 olive oil Nutrition 0.000 claims description 2
GIPDEPRRXIBGNF-KTKRTIGZSA-N oxolan-2-ylmethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CCCO1 GIPDEPRRXIBGNF-KTKRTIGZSA-N 0.000 claims description 2
125000006353 oxyethylene group Chemical group 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229940035044 sorbitan monolaurate Drugs 0.000 claims description 2
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
235000020238 sunflower seed Nutrition 0.000 claims description 2
229940072958 tetrahydrofurfuryl oleate Drugs 0.000 claims description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims 8
229960001361 ipratropium bromide Drugs 0.000 claims 4
KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims 4
229960001317 isoprenaline Drugs 0.000 claims 4
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 3
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims 2
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 1
239000002202 Polyethylene glycol Substances 0.000 claims 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims 1
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 claims 1
229920001223 polyethylene glycol Polymers 0.000 claims 1
230000003381 solubilizing effect Effects 0.000 claims 1
239000002671 adjuvant Substances 0.000 description 19
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 10
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 10
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 10
239000005642 Oleic acid Substances 0.000 description 10
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 10
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000004615 ingredient Substances 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
229920001983 poloxamer Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000004698 Polyethylene Substances 0.000 description 4
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229940124630 bronchodilator Drugs 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
MGYUQZIGNZFZJS-KTKRTIGZSA-N 2-[2-[(z)-octadec-9-enoxy]ethoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCO MGYUQZIGNZFZJS-KTKRTIGZSA-N 0.000 description 2
JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 2
241000592335 Agathis australis Species 0.000 description 2
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 2
WPMWEFXCIYCJSA-UHFFFAOYSA-N Tetraethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 2
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000000168 bronchodilator agent Substances 0.000 description 2
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DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
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229960002897 heparin Drugs 0.000 description 1
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OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
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229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
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229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
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HNJJXZKZRAWDPF-UHFFFAOYSA-N methapyrilene Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 HNJJXZKZRAWDPF-UHFFFAOYSA-N 0.000 description 1
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JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
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229960004927 neomycin Drugs 0.000 description 1
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SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
229960000395 phenylpropanolamine Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
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239000000047 product Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
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 description 1
239000003507 refrigerant Substances 0.000 description 1
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229960001860 salicylate Drugs 0.000 description 1
229960002646 scopolamine Drugs 0.000 description 1
STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
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229940035049 sorbitan monooleate Drugs 0.000 description 1
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229960005322 streptomycin Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
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239000011885 synergistic combination Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229960000195 terbutaline Drugs 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
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239000012588 trypsin Substances 0.000 description 1
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230000003639 vasoconstrictive effect Effects 0.000 description 1
238000003221 volumetric titration Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- 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
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
- 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
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A61K9/124—Aerosols; Foams characterised by the propellant

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Dispersion Chemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Otolaryngology (AREA)
Pulmonology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL9245789A 1988-12-06 1989-11-27 Drug aerosol preparations containing tetrafluoroethane IL92457A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888828477A GB8828477D0 (en)	1988-12-06	1988-12-06	Medical aerosol formulations

Publications (2)

Publication Number	Publication Date
IL92457A0 IL92457A0 (en)	1990-08-31
IL92457A true IL92457A (en)	1994-10-21

Family

ID=10648054

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9245789A IL92457A (en)	1988-12-06	1989-11-27	Drug aerosol preparations containing tetrafluoroethane

Country Status (13)

Country	Link
EP (4)	EP0372777B1 (de)
JP (1)	JP2786493B2 (de)
KR (1)	KR0154116B1 (de)
AU (1)	AU631155B2 (de)
CA (1)	CA2004598C (de)
DE (2)	DE68904300T2 (de)
DK (1)	DK595789A (de)
ES (2)	ES2045470T3 (de)
GB (1)	GB8828477D0 (de)
HK (2)	HK7196A (de)
IL (1)	IL92457A (de)
NZ (1)	NZ231579A (de)
ZA (1)	ZA899290B (de)

Families Citing this family (186)

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GB9024365D0 (en) *	1990-11-09	1991-01-02	Glaxo Group Ltd	Medicaments
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US5919435A (en)	1990-11-09	1999-07-06	Glaxo Group Limited	Aerosol formulation containing a particulate medicament
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US5182097A (en) *	1991-02-14	1993-01-26	Virginia Commonwealth University	Formulations for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content
US5190029A (en) *	1991-02-14	1993-03-02	Virginia Commonwealth University	Formulation for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content
EP0504112A3 (en) *	1991-03-14	1993-04-21	Ciba-Geigy Ag	Pharmaceutical aerosol formulations
ATE339952T1 (de) *	1991-06-10	2006-10-15	Schering Corp	Fluorchlorkohlenwasserstofffreie aerosolformulierungen
CA2111002C (en) †	1991-06-10	2000-08-22	Julianne Fassberg	Non-chlorofluorocarbon aerosol formulations
AU2178392A (en) *	1991-06-12	1993-01-12	Minnesota Mining And Manufacturing Company	Albuterol sulfate suspension aerosol formulations
US6123924A (en) *	1991-09-25	2000-09-26	Fisons Plc	Pressurized aerosol inhalation compositions
NZ244439A (en) *	1991-09-25	1994-01-26	Fisons Plc	Pressurised aerosol compositions comprising hydrofluoroalkane, dispersed
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CA2455115C (en)	1991-12-12	2008-05-27	Glaxo Group Limited	Pharmaceutical aerosol formulation
IL104068A (en) *	1991-12-12	1998-10-30	Glaxo Group Ltd	Surfactant-free pharmaceutical aerosol formulation comprising 1,1,1,2-tetrafluoroethane or 1,1,1,2,3,3,3-heptafluoro-n- propane as propellant
US5674471A (en) *	1991-12-12	1997-10-07	Glaxo Group Limited	Aerosol formulations containing P134a and salbutamol
US5744123A (en) *	1991-12-12	1998-04-28	Glaxo Group Limited	Aerosol formulations containing P134a and particulate medicaments
US5916540A (en)	1994-10-24	1999-06-29	Glaxo Group Limited	Aerosol formulations containing P134A and/or P227 and particulate medicament
NZ246046A (en) *	1991-12-12	1995-12-21	Glaxo Group Ltd	Aerosol comprising a particulate medicament in a fluorocarbon or chlorofluorohydrocarbon and a polar cosolvent
US5658549A (en) *	1991-12-12	1997-08-19	Glaxo Group Limited	Aerosol formulations containing propellant 134a and fluticasone propionate
GB9202522D0 (en) *	1992-02-06	1992-03-25	Glaxo Group Ltd	Medicaments
US5653962A (en) *	1991-12-12	1997-08-05	Glaxo Group Limited	Aerosol formulations containing P134a and particulate medicaments
US5736124A (en) *	1991-12-12	1998-04-07	Glaxo Group Limited	Aerosol formulations containing P134a and particulate medicament
US7105152B1 (en)	1991-12-18	2006-09-12	3M Innovative Properties Company	Suspension aerosol formulations
JP3908269B2 (ja) *	1991-12-18	2007-04-25	スリーエムカンパニー	懸濁エアゾール製剤
US7101534B1 (en)	1991-12-18	2006-09-05	3M Innovative Properties Company	Suspension aerosol formulations
DK0550031T3 (da) *	1991-12-31	1996-08-26	Solvay	Medicinsk aerosolformulering
US5202110A (en) *	1992-01-22	1993-04-13	Virginia Commonwealth University	Formulations for delivery of beclomethasone diproprionate by metered dose inhalers containing no chlorofluorocarbon propellants
DE4230876A1 (de) *	1992-03-17	1993-09-23	Asta Medica Ag	Druckgaspackungen unter verwendung von polyoxyethylen-glyceryl-oleaten
DE4218291A1 (de) *	1992-06-03	1993-12-09	Mattern Et Partner Pharmazeuti	Dosierspray für pernasale Applikation
MX9304585A (es) *	1992-07-31	1994-03-31	Glaxo Group Ltd	Formulacion farmaceutica en aerosol, lata adecuada para liberar la formulacion e inhalador de dosis dosificada que comprende la lata.
US5833950A (en) *	1992-07-31	1998-11-10	Glaxo Group Limited	Aerosol formulations containing beclomethasone dipropionate-1, 1, 1, 2-tetrafluoroethane solvate
GR1001487B (el) *	1992-11-19	1994-02-28	Fisons Plc	Πεπιεσμένες συν?έσεις αεροζόλης.
ES2064244B1 (es) *	1992-12-02	1995-09-01	Fisons Plc	Composiciones de aerosol presurizadas.
ATE177941T1 (de) *	1992-12-09	1999-04-15	Boehringer Ingelheim Pharma	Stabilisierte medizinische aerosollösungen
US5458798A (en) *	1993-02-05	1995-10-17	E. I. Du Pont De Nemours And Company	Azeotropic and azeotrope-like compositions of a hydrofluorocarbon and a hydrocarbon
US5492688A (en) *	1993-04-28	1996-02-20	The Center For Innovative Technology	Metered dose inhaler fomulations which include the ozone-friendly propellant HFC 134a and a pharmaceutically acceptable suspending, solubilizing, wetting, emulsifying or lubricating agent
DE69701051T2 (de)	1993-04-30	2000-08-31	Minnesota Mining And Mfg. Co., Saint Paul	Abdichtung an Aerosolbehältern
DE4322703A1 (de)	1993-07-08	1995-01-12	Asta Medica Ag	Druckgaspackungen unter Verwendung von Polyoxyethylen-glyceryl-fettsäureestern als Suspensionsstabilisatoren und Ventilschmiermittel
DE4323636A1 (de) *	1993-07-15	1995-01-19	Hoechst Ag	Arzneistoffzubereitungen aus umhüllten, schwerstwasserlöslichen Arzneistoffen für Inhalationsarzneiformen und Verfahren zu ihrer Herstellung
US5502076A (en) *	1994-03-08	1996-03-26	Hoffmann-La Roche Inc.	Dispersing agents for use with hydrofluoroalkane propellants
US5508023A (en) *	1994-04-11	1996-04-16	The Center For Innovative Technology	Pharmaceutically acceptable agents for solubilizing, wetting, emulsifying, or lubricating in metered dose inhaler formulations which use HFC-227 propellant
HU214582B (hu) *	1994-07-26	1998-04-28	EGIS Gyógyszergyár Rt.	Porlasztható, vérnyomáscsökkentő hatású gyógyszerkészítmény és eljárás előállítására
GB9419536D0 (en) *	1994-09-28	1994-11-16	Glaxo Inc	Medicaments
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1989
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- 1989-11-27 ES ES89312270T patent/ES2045470T3/es not_active Expired - Lifetime
- 1989-11-27 DE DE8989312270T patent/DE68904300T2/de not_active Revoked
- 1989-11-27 ES ES92201264T patent/ES2077971T5/es not_active Expired - Lifetime
- 1989-11-27 EP EP89312270A patent/EP0372777B1/de not_active Revoked
- 1989-11-27 DE DE68924540T patent/DE68924540T3/de not_active Expired - Lifetime
- 1989-11-27 EP EP99201136A patent/EP0995434A3/de not_active Withdrawn
- 1989-11-27 EP EP95200166A patent/EP0653204B1/de not_active Expired - Lifetime
- 1989-11-27 EP EP92201264A patent/EP0499344B2/de not_active Expired - Lifetime
- 1989-11-27 IL IL9245789A patent/IL92457A/en not_active IP Right Cessation
- 1989-11-29 NZ NZ231579A patent/NZ231579A/xx unknown
- 1989-12-05 CA CA002004598A patent/CA2004598C/en not_active Expired - Lifetime
- 1989-12-05 KR KR1019890017929A patent/KR0154116B1/ko not_active Expired - Lifetime
- 1989-12-05 ZA ZA899290A patent/ZA899290B/xx unknown
- 1989-12-06 AU AU45956/89A patent/AU631155B2/en not_active Expired
- 1989-12-06 JP JP1317415A patent/JP2786493B2/ja not_active Expired - Lifetime
1996
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1997
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Also Published As

Publication number	Publication date
EP0499344A2 (de)	1992-08-19
EP0499344B1 (de)	1995-10-11
DE68904300T2 (de)	1993-04-29
DE68904300D1 (de)	1993-02-18
EP0372777A3 (en)	1990-11-22
DK595789D0 (da)	1989-11-27
DK595789A (da)	1990-06-07
ES2077971T5 (es)	2009-12-17
JP2786493B2 (ja)	1998-08-13
ES2077971T3 (es)	1995-12-01
HK7196A (en)	1996-01-26
ES2045470T3 (es)	1994-01-16
EP0995434A2 (de)	2000-04-26
EP0372777B1 (de)	1993-01-07
AU4595689A (en)	1990-06-14
CA2004598A1 (en)	1990-06-06
EP0995434A3 (de)	2003-11-26
ZA899290B (en)	1991-06-26
DE68924540T3 (de)	2010-06-02
HK80497A (en)	1997-06-20
CA2004598C (en)	2000-11-07
KR900009057A (ko)	1990-07-02
GB8828477D0 (en)	1989-01-05
JPH02200627A (ja)	1990-08-08
EP0372777A2 (de)	1990-06-13
NZ231579A (en)	1993-11-25
DE68924540T2 (de)	1996-05-15
EP0653204A3 (de)	1995-11-15
KR0154116B1 (ko)	1998-11-16
IL92457A0 (en)	1990-08-31
EP0653204B1 (de)	2010-12-15
AU631155B2 (en)	1992-11-19
EP0499344B2 (de)	2009-09-09
DE68924540D1 (de)	1995-11-16
EP0653204A2 (de)	1995-05-17
EP0499344A3 (en)	1992-09-02

Legal Events

Date	Code	Title
2000-08-31	KB	Patent renewed
2004-02-08	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees
2008-01-06	KB	Patent renewed
2010-11-30	EXP	Patent expired

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US5766573A (en)	1998-06-16	Medicinal aerosol formulations
US5695743A (en)	1997-12-09	Medicinal aerosol formulations
CA2004598C (en)	2000-11-07	Medicinal aerosol formulations
US5439670A (en)	1995-08-08	Medicinal aerosol formulations
EP0493437B1 (de)	1995-08-02	Medizinische aerosolformulierungen
CA2352483C (en)	2009-01-20	Pharmaceutical aerosol composition containing hfa 227 and hfa 134a
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