DE2749075A1 - Quaternaere 1-methyl-2-(phenothiazin- 10-yl)-aethylammoniumsalze und diese enthaltende arzneimittel - Google Patents
Quaternaere 1-methyl-2-(phenothiazin- 10-yl)-aethylammoniumsalze und diese enthaltende arzneimittelInfo
- Publication number
- DE2749075A1 DE2749075A1 DE19772749075 DE2749075A DE2749075A1 DE 2749075 A1 DE2749075 A1 DE 2749075A1 DE 19772749075 DE19772749075 DE 19772749075 DE 2749075 A DE2749075 A DE 2749075A DE 2749075 A1 DE2749075 A1 DE 2749075A1
- Authority
- DE
- Germany
- Prior art keywords
- phenothiazin
- component
- methyl
- trimethyl
- ethyl
- 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.)
- Granted
Links
- -1 PHENOTHIAZIN- 10-YL Chemical class 0.000 title claims description 8
- 229940126601 medicinal product Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 229940124630 bronchodilator Drugs 0.000 claims description 8
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 7
- 206010006482 Bronchospasm Diseases 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000004561 phenothiazin-10-yl group Chemical group C1=CC=CC=2SC3=CC=CC=C3N(C12)* 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 238000002664 inhalation therapy Methods 0.000 claims description 4
- 239000006199 nebulizer Substances 0.000 claims description 4
- 229940107816 ammonium iodide Drugs 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000007883 bronchodilation Effects 0.000 claims description 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000000443 aerosol Substances 0.000 description 13
- 229960003910 promethazine Drugs 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical class C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 4
- 230000007885 bronchoconstriction Effects 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 210000002460 smooth muscle Anatomy 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 230000002685 pulmonary effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 238000011282 treatment 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
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- 229930182837 (R)-adrenaline Natural products 0.000 description 2
- HJDPZRKNMOFAFY-UHFFFAOYSA-N 1-phenothiazin-10-ylpropan-2-amine Chemical group C1=CC=C2N(CC(N)C)C3=CC=CC=C3SC2=C1 HJDPZRKNMOFAFY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000004044 bronchoconstricting agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- 229960005139 epinephrine Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229950004354 phosphorylcholine Drugs 0.000 description 2
- 229960002244 promethazine hydrochloride Drugs 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 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
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 206010000060 Abdominal distension Diseases 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 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
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 206010041277 Sodium retention Diseases 0.000 description 1
- 208000005279 Status Asthmaticus Diseases 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 206010043087 Tachyphylaxis Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 239000000464 adrenergic agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000004479 aerosol dispenser Substances 0.000 description 1
- 238000012387 aerosolization Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 239000002585 base 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
- 208000024330 bloating Diseases 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 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
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000009115 maintenance therapy Methods 0.000 description 1
- 235000019988 mead Nutrition 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
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- OSZNNLWOYWAHSS-UHFFFAOYSA-M neostigmine methyl sulfate Chemical compound COS([O-])(=O)=O.CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 OSZNNLWOYWAHSS-UHFFFAOYSA-M 0.000 description 1
- 229960002253 neostigmine methylsulfate Drugs 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002990 phenothiazines Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 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
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940032712 succinylcholine Drugs 0.000 description 1
- 229940120904 succinylcholine chloride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000010792 warming Methods 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
- A61K9/0012—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
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/26—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom without other substituents attached to the ring system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Dispersion Chemistry (AREA)
- Otolaryngology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/737,927 US4097596A (en) | 1976-11-02 | 1976-11-02 | Inhalation therapy for relieving bronchial spasm using quaternary salts of promethazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2749075A1 true DE2749075A1 (de) | 1978-05-11 |
| DE2749075C2 DE2749075C2 (forum.php) | 1990-10-25 |
Family
ID=24965840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772749075 Granted DE2749075A1 (de) | 1976-11-02 | 1977-11-02 | Quaternaere 1-methyl-2-(phenothiazin- 10-yl)-aethylammoniumsalze und diese enthaltende arzneimittel |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4097596A (forum.php) |
| JP (1) | JPS5359036A (forum.php) |
| BE (1) | BE860357A (forum.php) |
| CY (1) | CY1183A (forum.php) |
| DE (1) | DE2749075A1 (forum.php) |
| FR (1) | FR2368957A1 (forum.php) |
| GB (1) | GB1568591A (forum.php) |
| HK (1) | HK33983A (forum.php) |
| IE (1) | IE46070B1 (forum.php) |
| KE (1) | KE3269A (forum.php) |
| MY (1) | MY8400150A (forum.php) |
| NL (1) | NL7712035A (forum.php) |
| SG (1) | SG15883G (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1265647B1 (it) * | 1992-11-18 | 1996-11-22 | Farmin Srl | Composizione farmaceutiche topiche per le allergie respiratorie |
| WO2003105811A2 (en) * | 2002-01-31 | 2003-12-24 | Southwest Research Institute | Controlled release compositions and methods for using same |
| EP3958975A1 (en) * | 2019-04-24 | 2022-03-02 | Københavns Universitet | New class of antibiotics having low mic-values towards different strains of bacteria |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB881379A (en) * | 1959-05-29 | 1961-11-01 | Recip Ab | Phenothiazine compounds, their production, and pharmaceutical compositions containing them |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2590125A (en) * | 1952-03-25 | Quaternary-ammonium alkyl | ||
| US2887481A (en) * | 1957-04-29 | 1959-05-19 | Schering Corp | Heterocyclic amides |
| GB1144905A (en) * | 1965-03-25 | 1969-03-12 | Fisons Pharmaceuticals Ltd | Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof |
-
1976
- 1976-11-02 US US05/737,927 patent/US4097596A/en not_active Expired - Lifetime
-
1977
- 1977-10-27 IE IE2189/77A patent/IE46070B1/en not_active IP Right Cessation
- 1977-10-27 CY CY1183A patent/CY1183A/xx unknown
- 1977-10-27 GB GB44764/77A patent/GB1568591A/en not_active Expired
- 1977-10-28 FR FR7732827A patent/FR2368957A1/fr active Granted
- 1977-10-28 JP JP13020877A patent/JPS5359036A/ja active Granted
- 1977-10-31 BE BE182247A patent/BE860357A/xx not_active IP Right Cessation
- 1977-11-01 NL NL7712035A patent/NL7712035A/xx not_active Application Discontinuation
- 1977-11-02 DE DE19772749075 patent/DE2749075A1/de active Granted
-
1983
- 1983-04-02 KE KE3269A patent/KE3269A/xx unknown
- 1983-04-04 SG SG158/83A patent/SG15883G/en unknown
- 1983-09-01 HK HK339/83A patent/HK33983A/xx unknown
-
1984
- 1984-12-30 MY MY150/84A patent/MY8400150A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB881379A (en) * | 1959-05-29 | 1961-11-01 | Recip Ab | Phenothiazine compounds, their production, and pharmaceutical compositions containing them |
Non-Patent Citations (3)
| Title |
|---|
| Fortschr. Arzneimittel-Forschung, 5, 1963, S.293 u. S.330-332 * |
| J. Pharm. Sci. 59, 1970, S.772-775 u. 60, 1971, S.1895-1898 * |
| SCHRÖDER-RUFER-SCHMIECHEN: Arzneimittelchemie I, S.133-134, 1976 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2749075C2 (forum.php) | 1990-10-25 |
| SG15883G (en) | 1985-01-11 |
| IE46070L (en) | 1978-05-02 |
| JPS6236005B2 (forum.php) | 1987-08-05 |
| BE860357A (fr) | 1978-05-02 |
| KE3269A (en) | 1983-05-13 |
| US4097596A (en) | 1978-06-27 |
| FR2368957A1 (fr) | 1978-05-26 |
| GB1568591A (en) | 1980-06-04 |
| NL7712035A (nl) | 1978-05-05 |
| IE46070B1 (en) | 1983-02-09 |
| FR2368957B1 (forum.php) | 1980-06-13 |
| CY1183A (en) | 1983-10-07 |
| MY8400150A (en) | 1984-12-31 |
| JPS5359036A (en) | 1978-05-27 |
| HK33983A (en) | 1983-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD201139A5 (de) | Verfahren zur herstellung von (-)-n-methyl-3-(2-methylphenoxy)-3-phenylpropylamin und seinen pharmazeutisch unbedenklichen salzen | |
| DE2502916C2 (forum.php) | ||
| DE2429101C3 (de) | a-Isomeres des 2-Chlor-9- [3'-(N'-2hydroxyäthylpiperazino- N)-propyliden] -thioxanthens und dessen Ester, Verfahren zu deren Gewinnung bzw. Herstellung und diese Verbindungen enthaltende Mittel | |
| DE1911464C3 (de) | 3,4-Dihydroisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2403122C2 (forum.php) | ||
| DE1815808A1 (de) | Benzolderivate | |
| DE2716402A1 (de) | 7-(2,3-dihydroxypropyl)-1,3-di-n- propylxanthin, verfahren zu seiner herstellung und diese verbindung enthaltende arzneimittel | |
| DE3204960A1 (de) | Corynanthein-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE69127285T2 (de) | Verwendung von verbindungen zur behandlung von altersbedingtem gedächtnisschwund und anderen kognitiven störungen | |
| DE2113866A1 (de) | Neue Indolderivate,Verfahren zu deren Herstellung und eine,diese Verbindungen enthaltende therapeutische Zusammensetzung | |
| DE2749075A1 (de) | Quaternaere 1-methyl-2-(phenothiazin- 10-yl)-aethylammoniumsalze und diese enthaltende arzneimittel | |
| DE2038628C3 (de) | N,N'-Di(carboxyalkyI)-p-phenylendiamine, deren Salze und Diäthylester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2725245C2 (de) | Methylaminderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische oder veterinärmedizinische Zusammensetzungen | |
| DE2336671A1 (de) | Oxyessigsaeureaether von o-thymotinsaeureestern | |
| DE2525249A1 (de) | Neue dioxamsaeure-derivate, verfahren zur herstellung derselben und dieselben enthaltende pharmazeutische praeparate | |
| DE2164988C3 (de) | 2,2-Diphenylcyclopropancarbonsäureesterderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE2754148A1 (de) | Substituierte aminoaethanole, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe | |
| DE2244737B2 (de) | H-o-ChlorphenyD-2-tert-butylaminoäthanol, Verfahren zu dessen Herstellung und Arzneimittel auf dessen Basis | |
| DE2361488C3 (de) | Verwendung von Tri-n-propylessigsäurederivaten | |
| DE2145686C3 (de) | 2-Chlor-S-sulfamylbenzoesäurederivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten | |
| DE1695785A1 (de) | Neue,substituierte 2-Aminomethylbenzofuranverbindungen und Verfahren zu deren Herstellung | |
| DE2062055B2 (de) | Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE3546165A1 (de) | Verwendung von azoniaspironortropanolestern als asthmatherapeutikum und als broncholytikum | |
| DE1518444C (de) | erythro alpha Phenyl beta amino propanole, Verfahren zu ihrer Herstellung und solche Verbindungen enthaltende Arz neimittel | |
| DE2049058C3 (de) | Mit niedrigen Alkylgruppen N-substituierte N'-[ß-{23-Diphenyl-1 -pyrrolyl)-äthyl]- homopiperazine sowie Verfahren zu deren Herstellung und diese enthaltende Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: A61K 31/54 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |