IE59327B1 - Prazosin-pirbuterol combination for bronchodilation - Google Patents
Prazosin-pirbuterol combination for bronchodilationInfo
- Publication number
- IE59327B1 IE59327B1 IE291186A IE291186A IE59327B1 IE 59327 B1 IE59327 B1 IE 59327B1 IE 291186 A IE291186 A IE 291186A IE 291186 A IE291186 A IE 291186A IE 59327 B1 IE59327 B1 IE 59327B1
- Authority
- IE
- Ireland
- Prior art keywords
- pirbuterol
- prazosin
- weight
- mixture
- hcl
- Prior art date
Links
- 229960005414 pirbuterol Drugs 0.000 title claims abstract description 63
- 230000007883 bronchodilation Effects 0.000 title description 3
- 229960001289 prazosin Drugs 0.000 claims abstract description 69
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims abstract description 59
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 206010006482 Bronchospasm Diseases 0.000 claims abstract description 7
- 230000007885 bronchoconstriction Effects 0.000 claims abstract description 5
- 230000003182 bronchodilatating effect Effects 0.000 claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims abstract description 5
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 claims description 26
- XIDFCZTVVCWBGN-UHFFFAOYSA-N Pirbuterol hydrochloride Chemical compound Cl.Cl.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 XIDFCZTVVCWBGN-UHFFFAOYSA-N 0.000 claims description 22
- 239000000443 aerosol Substances 0.000 claims description 20
- 229960002386 prazosin hydrochloride Drugs 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 2
- 230000002195 synergetic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 3
- 230000002040 relaxant effect Effects 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 208000000059 Dyspnea Diseases 0.000 description 11
- 206010013975 Dyspnoeas Diseases 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- 239000012458 free base Substances 0.000 description 10
- 206010010904 Convulsion Diseases 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 230000006698 induction Effects 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229960004139 pirbuterol hcl Drugs 0.000 description 8
- 239000003380 propellant Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000002775 capsule Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 108010058846 Ovalbumin Proteins 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229940092253 ovalbumin Drugs 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000700198 Cavia Species 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 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 4
- QSXMZJGGEWYVCN-UHFFFAOYSA-N Pirbuterol acetate Chemical compound CC(O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 QSXMZJGGEWYVCN-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000006199 nebulizer Substances 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 206010019280 Heart failures Diseases 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229960004994 pirbuterol acetate Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- -1 elixirs Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000011597 hartley guinea pig Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- ZHIBQGJKHVBLJJ-UHFFFAOYSA-N histamine phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.NCCC1=CNC=N1 ZHIBQGJKHVBLJJ-UHFFFAOYSA-N 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 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 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 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
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 206010013974 Dyspnoea paroxysmal nocturnal Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000004327 Paroxysmal Dyspnea Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose 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)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/795,689 US4601897A (en) | 1985-11-06 | 1985-11-06 | Prazosin-pirbuterol combination for bronchodilation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE862911L IE862911L (en) | 1987-05-06 |
| IE59327B1 true IE59327B1 (en) | 1994-02-09 |
Family
ID=25166193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE291186A IE59327B1 (en) | 1985-11-06 | 1986-11-05 | Prazosin-pirbuterol combination for bronchodilation |
Country Status (14)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4868182A (en) * | 1986-11-05 | 1989-09-19 | Merrell Dow Pharmaceuticals Inc. | Enhancement of prazosin |
| ZA878182B (en) * | 1986-11-05 | 1988-05-02 | Merrell Dow Pharmaceuticals Inc. | Enhancement of prazosin |
| US5110927A (en) * | 1987-12-31 | 1992-05-05 | The United States Of America As Represented By The Department Of Health And Human Services | Prazosin analog with increased selectivity and duration of action |
| US5225183A (en) * | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| US5776434A (en) | 1988-12-06 | 1998-07-07 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| US6048857A (en) * | 1989-10-17 | 2000-04-11 | Ellinwood, Jr.; Everett H. | Dosing method of administering medicaments via inhalation administration |
| US5439670A (en) * | 1989-11-28 | 1995-08-08 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| US5503869A (en) * | 1994-10-21 | 1996-04-02 | Glaxo Wellcome Inc. | Process for forming medicament carrier for dry powder inhalator |
| JP2008535924A (ja) * | 2005-04-12 | 2008-09-04 | エラン ファーマ インターナショナル リミテッド | ナノ粒子キナゾリン誘導体製剤 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517005A (en) * | 1967-10-26 | 1970-06-23 | Pfizer & Co C | Certain 2- and 4-substituted quinazolines |
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| US3723434A (en) * | 1970-07-17 | 1973-03-27 | Pfizer | Piperazino isoquinoline bronchodilators |
| US3786160A (en) * | 1971-02-16 | 1974-01-15 | Pfizer | Use of 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)-pyridines as bronchodilators |
| US3700681A (en) * | 1971-02-16 | 1972-10-24 | Pfizer | 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)pyridines |
| US4092315A (en) * | 1976-03-01 | 1978-05-30 | Pfizer Inc. | Novel crystalline forms of prazosin hydrochloride |
| GB1591490A (en) * | 1977-08-04 | 1981-06-24 | Abbott Lab | 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine hydrochloride dihydrate |
| US4175128A (en) * | 1979-01-03 | 1979-11-20 | Pfizer Inc. | Method for treating congestive heart failure |
| FI67699C (fi) * | 1979-01-31 | 1985-05-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
| DE3235565A1 (de) * | 1982-09-25 | 1984-03-29 | Boehringer Ingelheim KG, 6507 Ingelheim | Piperidinderivate, ihre herstellung und verwendung |
-
1985
- 1985-11-06 US US06/795,689 patent/US4601897A/en not_active Expired - Fee Related
-
1986
- 1986-11-03 IL IL80476A patent/IL80476A0/xx not_active IP Right Cessation
- 1986-11-03 DE DE8686308544T patent/DE3676640D1/de not_active Expired - Lifetime
- 1986-11-03 EP EP86308544A patent/EP0222575B1/en not_active Expired - Lifetime
- 1986-11-03 ES ES198686308544T patent/ES2036174T3/es not_active Expired - Lifetime
- 1986-11-03 AT AT86308544T patent/ATE59295T1/de active
- 1986-11-04 CA CA000522113A patent/CA1284107C/en not_active Expired - Lifetime
- 1986-11-05 JP JP61263624A patent/JPS62135424A/ja active Granted
- 1986-11-05 ZA ZA868427A patent/ZA868427B/xx unknown
- 1986-11-05 IE IE291186A patent/IE59327B1/en not_active IP Right Cessation
- 1986-11-05 AU AU64832/86A patent/AU567018B2/en not_active Ceased
- 1986-11-05 DK DK527186A patent/DK527186A/da not_active Application Discontinuation
- 1986-11-05 NZ NZ218175A patent/NZ218175A/xx unknown
-
1991
- 1991-01-31 GR GR91400121T patent/GR3001420T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE862911L (en) | 1987-05-06 |
| AU567018B2 (en) | 1987-11-05 |
| JPH0524890B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-04-09 |
| EP0222575B1 (en) | 1990-12-27 |
| US4601897A (en) | 1986-07-22 |
| ATE59295T1 (de) | 1991-01-15 |
| JPS62135424A (ja) | 1987-06-18 |
| NZ218175A (en) | 1989-04-26 |
| EP0222575A1 (en) | 1987-05-20 |
| DK527186D0 (da) | 1986-11-05 |
| GR3001420T3 (en) | 1992-09-25 |
| DK527186A (da) | 1987-05-07 |
| IL80476A0 (en) | 1987-02-27 |
| ZA868427B (en) | 1988-06-29 |
| AU6483286A (en) | 1987-05-21 |
| DE3676640D1 (de) | 1991-02-07 |
| ES2036174T3 (es) | 1993-05-16 |
| CA1284107C (en) | 1991-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Gross et al. | Anticholinergic, antimuscarinic bronchodilators | |
| EP1315505B1 (en) | Pharmaceutical compositions for headache, migraine, nausea and emesis | |
| EP0481675A2 (en) | Preparation of medicaments for treating asthma using (S)-alpha-fluoromethyl histidine and esters thereof | |
| HU190699B (en) | Process for producing analgesic composition containing nalbufin | |
| US4601897A (en) | Prazosin-pirbuterol combination for bronchodilation | |
| US3922340A (en) | Pharmaceutical compositions for treating lung diseases | |
| NZ541187A (en) | Use of a combination containing a non-nucleoside reverse transcriptase inhibitor (NNRTI) with an inhibitor of cytochrome P450, such as protease inhibitors | |
| JPH01100120A (ja) | 薬剤組成物 | |
| EP0425909A2 (en) | Method for rehabilitating the vasorelaxant action of the coronary arteries impaired through atherosclerosis or hypercholesterolemia employing an ace inhibitor | |
| KR0178762B1 (ko) | 특정 인돌 유도체의 신규 의약적 용도 및 그를 함유하는 제약 조성물 | |
| US6498173B1 (en) | Synergistic combination comprising roflumilast and a pde-3 inhibitor | |
| US5011841A (en) | Treatment of depression | |
| Tigerstedt et al. | Comparison of the analgesic dose‐effect relationships of nefopam and oxycodone in postoperative pain | |
| US4175128A (en) | Method for treating congestive heart failure | |
| EP0640338A1 (en) | Sodium cromoglycate for the treatment of upper respiratory tract infections | |
| US4829068A (en) | Treatment of disorders of the gastro-intestinal tract | |
| US4689213A (en) | Method and composition for treating bronchospastic airway diseases | |
| JPS6139287B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0474438A1 (en) | Method for preventing or treating cerebrovascular disease employing the ACE-inhibitor ceronapril | |
| US3821381A (en) | Method of treatment | |
| CA2264172A1 (en) | Remedies for allergic dermatitis | |
| US3867534A (en) | Dosage regimen | |
| EP1611888A1 (en) | Antitussives | |
| Bowden et al. | The effect of trifluoperazine on bronchial responsiveness in asthma | |
| WO1987000047A1 (en) | Method and composition for the treatment of chronic obstructive pulmonary disease |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |