NO154294B - Doseinhalator. - Google Patents
Doseinhalator. Download PDFInfo
- Publication number
- NO154294B NO154294B NO822370A NO822370A NO154294B NO 154294 B NO154294 B NO 154294B NO 822370 A NO822370 A NO 822370A NO 822370 A NO822370 A NO 822370A NO 154294 B NO154294 B NO 154294B
- Authority
- NO
- Norway
- Prior art keywords
- indazole
- lower alkyl
- melting point
- boiling point
- general formula
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 34
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001741 anti-phlogistic effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- CJBXLBPSBLXDJO-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2h-indazol-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(=O)N1 CJBXLBPSBLXDJO-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/0065—Inhalators with dosage or measuring devices
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/0001—Details of inhalators; Constructional features thereof
- A61M15/0005—Details of inhalators; Constructional features thereof with means for agitating the medicament
- A61M15/0006—Details of inhalators; Constructional features thereof with means for agitating the medicament using rotating means
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M2202/00—Special media to be introduced, removed or treated
- A61M2202/06—Solids
- A61M2202/064—Powder
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Disintegrating Or Milling (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Containers And Packaging Bodies Having A Special Means To Remove Contents (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Nozzles (AREA)
- Filtering Of Dispersed Particles In Gases (AREA)
Description
Fremgangsmåte for fremstilling av terapeutisk virksomme i 1-stilling substituerte 3-dialkylaminoalkoxy-indazoler.
Nærværende oppfinnelse vedrører en fremgangsmåte for fremstilling av i 1-stilling substituerte 3-dialkylaminoalkoxy-indazoler med den generelle formel I
hvor R står for hydrogen eller klor, R' står for en lavere alkylrest eller en i arylkjernen eventuelt med halogenatomer eller lavere alkyl- henholdsvis alkoxyrester substituert fenyl- eller fenyl-lavere-alkylgruppe, R" for hydrogen eller en
lavere alkylgruppe, R'" for en lavere alkylrest som ved de to R'" kan være lik eller forskjellig, og n står for tallet 1 eller 2.
Fortrinnsvis står R' for en methyl-, ethyl, fenyl-, benzyl-, p-klorbenzyl-, p-methoxybenzyl-eller en |3-fenylethylgruppe, mens R" fortrinnsvis står for en methylgruppe og R'" fortrinnsvis for hydrogen eller en methylgruppe.
Forbindelsene med den generelle formel I som fortrinnsvis blir fremstilt i form av sine salter, f. eks. som hydroklorid, citrat, maleat eller sulfat, har interessante analgetiske og an-tiflogistiske egenskaper, hvorved noen av forbindelsene har også en muskelavslappende virkning. En l-benzyl-3-8-dimethylaminopropoxy-indazol-hydroklorid som anføres som eksempel har de følgende farmakologiske egenskaper: 1) en fremtredende analgetisk virkning, når produktet undersøkes etter den antiinflamma-toriske effekt (Randall og Selitto, fenylkinon);
her er forbindelsen i følge oppfinnelsen tre ganger så virksom som acetylsalisylsyre. Virkningen av forbindelsen er mer moderat, når undersøkel-sen gjennomføres etter varme- henholdsvis het-plateprøven; 2) en særlig fremtredende antiflogistisk virkning, når undersøkelsen gjennomføres etter den kronologiske sølvnitratprøven; her en forbindelsen tre ganger så virksom som fenylbuta-zon; 3) en god virkning med hensyn til den poly-synaptiske ryggradsrefleks; her er forbindelsen ifølge 'oppfinnelsen åtte ganger så virksom som mefenesin.
Forbindelsene ifølge oppfinnelsen er fri for sentrale effekter og hindrer ikke betingende re-fleks, som ofte er tilfelle ved analgetiske narko-tika av morfintypen.
Forbindelser med den generelle formel I kan ifølge oppfinnelsen fremstilles ved at man overfører en 3-hydroxy-indazol med den generelle formel II
i hvilken R og R' har den samme betydning som i formel I, i alkalisaltet, fortrinnsvis natrlum-saltet og omsetter saltet i et egnet inert opp-løsningsmiddel med et halogenalkyldialkylamin med den generelle formel III hvor R", R'" og n har den samme betydning som i formel I og Hal står for et halogenatom, fortrinnsvis et kloratom. De 3-hydroxy-indazolene med den generelle formel II kan frembringes ved at de fremstilles fra N-substituerte anthranilsyrer eller estere av slike syrer. Disse syrene henholdsvis estrene til-svarende den generelle formel IV nitroseres og de erholdte nitrosoderivater med formel V reduseres med f. eks. natriumhydrosulfit, hvorved natriumsaltene av 3-hydroxyindazoler med den generelle formel II oppnås direkte.
I den ovenstående reaksjonsrekkefølge har R og R' den ovenfor nevnte betydning; R"" står for hydrogen eller en lavere alkylgruppe.
Eksempel 1 : l- p- klobenzyl- 3- fi- dimethylaminoethoxy-
lH- indazol. 12,9 g l-p-klorbenzyl-3-hydroxy-lH-indazol oppløses i 250 cm<3> varmt toluol. 2,2 g natrium-amid tilsettes. Blandingen oppvarmes en time under omrøring. 10 g friskt destillert klorethyl-dimethylamin, oppløst i 110 cm<3> toluol tilsettes. Oppvarming og omrøring fortsetter i ca. 4 timer. De uorganiske stoffene filtreres fra. Blandingen extraheres med 2-n-saltsyre. Oppløsningen gjø-res alkalisk med NaOH, extraheres med eter og tørkes over kaliumkarbonat. Opløsningsmiddelet fjernes. Resten destilleres under redusert trykk. 14 g av et stoff med kokepunkt på 185° C/0.1 mm oppnås. l-p-klorbenzyl-3-p-dimethyl-amino-ethoxy-lH-indazolhydroklorid omkrystalleres fra
ethylacetåt; det har et smeltepunkt på 155° C.
Eksempel 2: l- benzyl- 3- y- dimethylaminopropoxy- 6- klor-IH- indazol.
Natriumsaltet av l-benzyl-3-hydroxy-6-klor-lH-indazol fremstilles, ved at det nevnte indazol oppløses i en ekvivalent mengde av natrium-ethylat i methanol og reaksjonsblandingen brin-ges til tørrhet under redusert trykk. 15 g av natriumsaltet pulveriseres meget grundig og sus-penderes i 130 cm<8> xylol. En oppløsning på 7 g klorpropyldimethylamin i 10 cm<3> xylol tilsettes hurtig. Blandingen blir oppvarmet i 2 timer, der-på tilsettes ytterligere 2 g klorpropyldimethylamin. Etter ytterligere oppvarming i en time, tilsettes på ny 2 g klorpropyldimethylamni. Der-på oppvarmes det ytterligere i 4 timer. Blandingen kjøles av, vaskes med vann, tørkes og opp-løsningsmidlet dampes av. 1,7 g av l-benzyl-3y-dimethylaminopropoxy-6-klor-lH-indazol med kokepunkt 197° C/0,5 mm oppnås etter destille-ring under redusert trykk. Hydrokloridet av dette indazol kan fremstilles med eteriske HCl-oppløs-ning, det kan omkrystalliseres fra ethylacetåt, som er tilsatt noen dråper etanol, F = 140° C.
De nærværende oppførte forbindelser kan blii analogisk fremstilt til eksemplene 1 til 4. l-methyl-3-p-dimetylaminoethoxy-lH-indazol Kokepunkt = 115°/0.3 HC1 smeltepunkt = 161° C l-methyl-3-Y-dimethylaminopropoxy-lH-ihdazol kokepunkt — 122° C/0.3 HC1 smeltepunkt = 150° C
1 - f eny 1- 3 - (3 - dimethy laminoe thoxy -1 H-indazol kokepunkt = 190° C/l HC1 smeltepunkt = 175° C l-fenyl-3-p-diethylaminoethoxy-lH-indazol kokepunkt = 140° C/0,02 Citrat smeltepunkt = 75° C l-fenyl-3-Y-dimethylaminopropoxy-lH-indazol kokepunkt = 65° C HC1 smeltepunkt = 197° C 1 -benzyl-3 - p-dimethylaminoethoxy- lH-indazol kokepunkt = 190° C/l HC1 smeltepunkt = 155° C l-benzyl-3-p-diethylaminoethoxy-lH-indazol kokepunkt = 170° C/0,1 Citrat smeltepunkt — 104° C l-benzyl-3-Y-dimethylaminopropoxy-lH-indazol kokepunkt = 160° C/0,05 HC1 smeltepunkt = 160° C
Cirtat 115—7
Maleat 113° C
Sulfat 149° C
l-p-klorbenzyl-3-p-diethylaminoethoxy-lH-indazol kokepunkt 170° C/0,2 mm HC1 smeltepunkt = 124° C
Citrat smeltepunkt = 93° C l-p-klorbenzyl-3-Y-dimethylaminopropoxy-lH-indazol
kokepunkt = 171° C/0,1 HC1 smeltepunkt = 120° C
l-fenethyl-3-p-dimethylaminoethoxy-lH-indazol kokepunkt = 165° C/0.2 mm HC1 smeltepunkt 181° C l-benzyl-3-p-dimethylaminoethoxy-5-klor-lH-indazol kokepunkt = 176° C/0.2 HC1 smeltepunkt = 195° C l-p-methoxybenzyl-3-p-dimethylaminoethoxy-lH-indazol kokepunkt = 189° C/0.3 HC1 smeltepunkt = 215° C l-p-klorbenzyl-3-y-diethylaminopropoxy-lH-indazol kokepunkt = 205° C/0.3 HC1 smeltepunkt = 96° C l-p-methoxybenzyl-3-Y-dimethylaminopropoxy-lH-indazol ikokepunkt = 200° C/0.4 HC1 smeltepunkt = 120° C l-benzyl-3-Y-dimethylarninopiropoxy-5-klor-lH-indazol kokepunkt = 187° C/0.2 HC1 smeltepunkt = 160° C l-fenethyl-3-Y-dimethylaminopropoxy-lH-indazol kokepunkt = 174° C/0.2 HC1 smeltepunkt = 173° C l-p-klorbenzyl-3-n-methyl-p-dimethyl-amino-ethoxy-lH-indazol kokepunkt = 180° C/0.1 HC1 smeltepunkt = 178° C l-p-methoxybenzyl-3-a-methyl-p-dimethylaminoethoxy-5-klor-lH-indazol kokepunkt = 198° C/0.2 HC1 smeltepunkt = 135° C l-p-methoxybenzyl-3-Y-methylaminopropoxy-5-klor-lH-indazol kokepunkt '= 220° C/0.2 HC1 smeltepunkt = 117° C l-p-methoxybenzyl-3-p-dimethylaminoethoxy-5-klor-lH-indazol kokepunkt = 207° C/0.4 HC1 smeltepunkt = 130° C l-benzyl-3-(3-dimethylaminoethoxy-6-klor-lH-
indazol kokepunkt = 180 C/0.2 HC1 smeltepunkt
= 199° C l-benzyl-3-a-methyl-p-dimethylaminoethoxy-6-klor-lH-indazol kokepunkt = 187° C/0.2 HC1 smeltepunkt = 148° C l-butyl-3-p-dimethylaminoethoxy-5-klor-lH-indazol kokepunkt = 173° C/0.3 HC1 smeltepunkt
= 122° C l-butyl-3-Y-dimethylaminopropoxy-5-klor-lH-indazol kokepunkt = 166° C/0.2 HC1 smeltepunkt
= 139° C l-butyl-6-klor-3-p-dimethylaminoethoxy-lH-indazol kokepunkt = 155° C/0.5 l-benzyl-3-Y-dimethylaminopiropoxy-4-klOir-lH-indazol kokepunkt = 188° C/0.2 HC1 smeltepunkt
= 160° C l-p-klorbenzyl-3-p-dimethylaminoethoxy-6-klor-lH-indazol kokepunkt = 193° C/0.5 HC1 smeltepunkt = 190° C l-p-klorbenzyl-3-Y-dimethylaminopropoxy-6-klor-lH-indazol kokepunkt = 197° C/0.3 HC1 smeltepunkt = 173° C
l-m-klorbenzyl-3-Y-dimethylaminopropoxy-lH-indazol kokepunkt = 195° C/0.5 HC1 smeltepunkt
= 197° C l-o-klorbenzyl-3-y-dimethylaminopropoxy-lH-indazol kokepunkt = 185° !C/0.2 HC1 smeltepunkt
= 140° C l-(m,p-dimethyoxybenzyl)-3-Y-dimethylaminopropoxy-lH-indazol kokepunkt = 209° C/0.3 HC1 smeltepunkt = 111° C.
Claims (1)
- Fremgangsmåte for fremstilling av terapeutisk virksomme i 1-stilling substituerte 3-dial-kylamino-alkoxyindazoler med den generelle formel:hvor R står for hydrogen eller klor, R' for en lavere alkylrest eller en i arylkjernen eventuelt med halogenatomer eller lavere alkyl-, henholdsvis alkoxyrester substituert fenyl- eller fenyl-lavere-alkylgruppe, R" for hydrogen eller en lavere alkylgruppe, R'" for en lavere alkylrest, som ved de to R'" kan være lik eller forskjellig og n for tallet 1 eller 2, og deres salter,karakterisert ved at en forbindelse med den generelle formel II: hvor R og R' har samme betydning som ovenfor nevnt, og R"" står for hydrogen eller en lavere alkylgruppe, nitroseres, det erholdte ni-trosoderivat reduseres og at et alkalimetallsalt av det slik erholdte 3-hydroxy-indazol med den generelle formel: hvor R og R' har samme betydning som ovenfor nevnt, omsettes i et egnet inert oppløsningsmid-del med et halogenalkyldialkylamin med den generelle formel: hvor R" og R'" og n har samme betydning som ovenfor nevnt og Hal står for halogen, hvor-etter, hvis ønsket, saltene på i og for seg kjent måte fremstilles. Anførte publikasjoner:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO86860142A NO157205C (no) | 1981-07-08 | 1986-01-16 | Anvendelse av en perforert skive som doserings- og holdeinnretning for fast, ufortynnet farmakologisk aktiv substans i mikronisert form i en doseinhalator. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8104239 | 1981-07-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO822370L NO822370L (no) | 1983-01-10 |
| NO154294B true NO154294B (no) | 1986-05-20 |
| NO154294C NO154294C (no) | 1986-09-03 |
Family
ID=20344220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822370A NO154294C (no) | 1981-07-08 | 1982-07-07 | Doseinhalator. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4524769A (no) |
| EP (1) | EP0069715B1 (no) |
| JP (1) | JPS5819269A (no) |
| KR (1) | KR880001811B1 (no) |
| AT (1) | ATE23272T1 (no) |
| AU (1) | AU559297B2 (no) |
| CA (1) | CA1178151A (no) |
| CY (1) | CY1492A (no) |
| DE (1) | DE3274065D1 (no) |
| DK (1) | DK159052C (no) |
| EG (1) | EG16516A (no) |
| ES (1) | ES276079Y (no) |
| FI (1) | FI77375C (no) |
| GR (1) | GR76522B (no) |
| HK (1) | HK64389A (no) |
| HU (1) | HU189154B (no) |
| IE (1) | IE53933B1 (no) |
| IL (1) | IL66053A (no) |
| IN (1) | IN158972B (no) |
| IS (1) | IS1268B6 (no) |
| KE (1) | KE3890A (no) |
| MY (1) | MY100090A (no) |
| NO (1) | NO154294C (no) |
| NZ (1) | NZ201154A (no) |
| PH (1) | PH22387A (no) |
| PL (1) | PL132252B1 (no) |
| PT (1) | PT75211B (no) |
| SG (1) | SG37089G (no) |
| YU (1) | YU45115B (no) |
| ZA (1) | ZA824264B (no) |
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| US11485A (en) * | 1854-08-08 | Befbigeeatob fobj maeine ejstgiites | ||
| US2641254A (en) * | 1948-10-18 | 1953-06-09 | Frederick M Turnbull | Applicator |
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| DE1813993C3 (de) * | 1968-12-11 | 1974-01-24 | Paul Ritzau Pari-Werk Kg, 8135 Soecking | Vorrichtung zum Zerstäuben und Vernebeln von flüssigen oder pulverförmigen Stoffen |
| US3653380A (en) * | 1970-02-16 | 1972-04-04 | American Cyanamid Co | Aerosol powder dosage dispensing device |
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| SU570775A1 (ru) * | 1976-02-02 | 1977-08-30 | Институт Теоретических Проблем Химической Технологии Ан Азербайджанской Сср | Объемный микродозатор жидкости |
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-
1982
- 1982-06-10 EP EP82850129A patent/EP0069715B1/en not_active Expired
- 1982-06-10 DE DE8282850129T patent/DE3274065D1/de not_active Expired
- 1982-06-10 CY CY1492A patent/CY1492A/xx unknown
- 1982-06-10 AT AT82850129T patent/ATE23272T1/de not_active IP Right Cessation
- 1982-06-14 IL IL66053A patent/IL66053A/xx not_active IP Right Cessation
- 1982-06-15 IS IS2734A patent/IS1268B6/is unknown
- 1982-06-16 ZA ZA824264A patent/ZA824264B/xx unknown
- 1982-06-17 CA CA000405376A patent/CA1178151A/en not_active Expired
- 1982-06-17 US US06/389,213 patent/US4524769A/en not_active Expired - Lifetime
- 1982-06-17 IN IN456/DEL/82A patent/IN158972B/en unknown
- 1982-06-21 PH PH27463A patent/PH22387A/en unknown
- 1982-06-23 IE IE1495/82A patent/IE53933B1/en not_active IP Right Cessation
- 1982-06-29 YU YU1414/82A patent/YU45115B/xx unknown
- 1982-07-05 AU AU85608/82A patent/AU559297B2/en not_active Expired
- 1982-07-05 NZ NZ201154A patent/NZ201154A/en unknown
- 1982-07-07 DK DK304482A patent/DK159052C/da not_active IP Right Cessation
- 1982-07-07 JP JP57117050A patent/JPS5819269A/ja active Granted
- 1982-07-07 FI FI822423A patent/FI77375C/fi not_active IP Right Cessation
- 1982-07-07 NO NO822370A patent/NO154294C/no not_active IP Right Cessation
- 1982-07-07 GR GR68677A patent/GR76522B/el unknown
- 1982-07-07 ES ES1982276079U patent/ES276079Y/es not_active Expired
- 1982-07-07 HU HU822219A patent/HU189154B/hu unknown
- 1982-07-07 PT PT75211A patent/PT75211B/pt unknown
- 1982-07-08 KR KR8203041A patent/KR880001811B1/ko active
- 1982-07-08 PL PL1982237363A patent/PL132252B1/pl unknown
- 1982-07-10 EG EG419/82A patent/EG16516A/xx active
-
1987
- 1987-10-01 MY MYPI87002747A patent/MY100090A/en unknown
-
1989
- 1989-06-12 SG SG370/89A patent/SG37089G/en unknown
- 1989-06-21 KE KE3890A patent/KE3890A/xx unknown
- 1989-08-10 HK HK643/89A patent/HK64389A/xx not_active IP Right Cessation
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