CH618436A5 - - Google Patents

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Info

Publication number: CH618436A5
Authority: CH; Switzerland
Prior art keywords: hydrochloride; prazosin hydrochloride; prazosin; polyhydrate; furoyl
Prior art date: 1976-03-01

Application number

CH255577A

Other languages

English (en)

French (fr)

Inventor

Ernest John Bianco

Original Assignee

Pfizer

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.)

1976-03-01

Filing date

1977-03-01

Publication date

1980-07-31

1977-03-01 Application filed by Pfizer filed Critical Pfizer

1980-07-31 Publication of CH618436A5 publication Critical patent/CH618436A5/fr

Links

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 98
229960002386 prazosin hydrochloride Drugs 0.000 claims description 95
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical group CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 30
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 28
238000002329 infrared spectrum Methods 0.000 claims description 20
238000000034 method Methods 0.000 claims description 18
238000004090 dissolution Methods 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
238000010438 heat treatment Methods 0.000 claims description 12
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 description 9
239000002904 solvent Substances 0.000 claims description 9
206010020772 Hypertension Diseases 0.000 claims description 7
150000004677 hydrates Chemical class 0.000 claims description 7
239000000843 powder Substances 0.000 claims description 7
229960001289 prazosin Drugs 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
-1 2-furoyl Chemical group 0.000 claims description 6
230000001476 alcoholic effect Effects 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
239000002220 antihypertensive agent Substances 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
230000001631 hypertensive effect Effects 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
238000010521 absorption reaction Methods 0.000 claims description 4
238000012986 modification Methods 0.000 claims description 4
230000004048 modification Effects 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000002723 alicyclic group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
210000004051 gastric juice Anatomy 0.000 claims description 2
238000001228 spectrum Methods 0.000 claims description 2
239000002253 acid Chemical class 0.000 claims 2
230000001077 hypotensive effect Effects 0.000 claims 2
208000001953 Hypotension Diseases 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
208000021822 hypotensive Diseases 0.000 claims 1
230000007246 mechanism Effects 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 claims 1
230000000704 physical effect Effects 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 14
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 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
QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
230000009466 transformation Effects 0.000 description 7
150000004683 dihydrates Chemical class 0.000 description 6
239000003814 drug Substances 0.000 description 6
150000004682 monohydrates Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
230000008859 change Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000002609 medium Substances 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000008901 benefit Effects 0.000 description 4
238000007707 calorimetry Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000008188 pellet Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical group [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000036765 blood level Effects 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
235000019739 Dicalciumphosphate Nutrition 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
238000010586 diagram Methods 0.000 description 2
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
229940038472 dicalcium phosphate Drugs 0.000 description 2
229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000011148 porous material Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 description 1
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 description 1
BVIJQMCYYASIFP-UHFFFAOYSA-N 2-methylcyclopentan-1-ol Chemical compound CC1CCCC1O BVIJQMCYYASIFP-UHFFFAOYSA-N 0.000 description 1
KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
RGRUUTLDBCWYBL-UHFFFAOYSA-N 2-methylhexan-3-ol Chemical compound CCCC(O)C(C)C RGRUUTLDBCWYBL-UHFFFAOYSA-N 0.000 description 1
PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 1
APKHJGDGWQDBGM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperazin-1-ylquinazolin-4-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCNCC1 APKHJGDGWQDBGM-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 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
NBXCMJBSSNLVJK-UHFFFAOYSA-N Cl.Cl.NC1=NC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)C=1OC=CC1 Chemical compound Cl.Cl.NC1=NC(=NC2=CC(=C(C=C12)OC)OC)N1CCN(CC1)C(=O)C=1OC=CC1 NBXCMJBSSNLVJK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
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
238000004566 IR spectroscopy Methods 0.000 description 1
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 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 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
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
230000009286 beneficial effect Effects 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
230000037396 body weight Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
238000004519 manufacturing process Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000001782 photodegradation Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000000634 powder X-ray diffraction Methods 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
238000007614 solvation Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 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
238000002411 thermogravimetry Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)

CH255577A 1976-03-01 1977-03-01 CH618436A5 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/662,937 US4092315A (en)	1976-03-01	1976-03-01	Novel crystalline forms of prazosin hydrochloride

Publications (1)

Publication Number	Publication Date
CH618436A5 true CH618436A5 (sv)	1980-07-31

Family

ID=24659839

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH255577A CH618436A5 (sv)	1976-03-01	1977-03-01

Country Status (32)

Country	Link
US (1)	US4092315A (sv)
JP (1)	JPS604188B2 (sv)
AR (1)	AR210937A1 (sv)
AU (1)	AU506937B2 (sv)
BE (1)	BE851878A (sv)
BG (1)	BG29724A3 (sv)
CA (1)	CA1068269A (sv)
CH (1)	CH618436A5 (sv)
CS (1)	CS191332B2 (sv)
DD (1)	DD129652A5 (sv)
DE (1)	DE2708192C3 (sv)
DK (1)	DK145858C (sv)
ES (1)	ES8707447A1 (sv)
FI (1)	FI62082C (sv)
FR (1)	FR2372828A1 (sv)
GB (1)	GB1538713A (sv)
HK (1)	HK30881A (sv)
HU (1)	HU173641B (sv)
IE (1)	IE44522B1 (sv)
IL (1)	IL51481A (sv)
LU (1)	LU76868A1 (sv)
MY (1)	MY8100271A (sv)
NL (1)	NL169591C (sv)
NO (1)	NO146499C (sv)
NZ (1)	NZ183450A (sv)
PL (1)	PL105559B1 (sv)
PT (1)	PT66227B (sv)
RO (1)	RO73095A (sv)
SE (1)	SE423234B (sv)
SU (1)	SU644387A3 (sv)
YU (1)	YU41294B (sv)
ZA (1)	ZA77918B (sv)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9976252B2 (en)	2014-07-21	2018-05-22	Keir Manufacturing, Inc.	Aerodynamic flyer bow

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX5483E (es) *	1977-08-04	1983-08-23	Abbott Lab	Procedimiento para la preparacion del dihidrato clorhidrato de 1-(4-amino-6,7-dimetoxi-2-quinazolinil)-4-(2-tetrahidrofuroil)piperazina
GB1591490A (en) *	1977-08-04	1981-06-24	Abbott Lab	1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine hydrochloride dihydrate
US4197301A (en) *	1978-10-16	1980-04-08	Allergan Pharmaceuticals, Inc.	Topical ophthalmic use of Prazosin
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
US4440769A (en) *	1983-02-11	1984-04-03	Abbott Laboratories	2-(4-Phenylalkanoylpiperazin-1-yl) quinazoline compounds, pharmaceutical compositions and method of producing α1 antagonistic activity
FI79107C (sv) *	1984-06-25	1989-11-10	Orion Yhtymae Oy	Förfarande för framställning av stabil -form av prazosinhydroklorid.
US5322943A (en) *	1985-09-12	1994-06-21	The Upjohn Company	Piperazine compounds which are substituted
US4601897A (en) *	1985-11-06	1986-07-22	Pfizer Inc.	Prazosin-pirbuterol combination for bronchodilation
DE3683760D1 (de) *	1986-03-21	1992-03-12	Heumann Pharma Gmbh & Co	Kristalline, wasserfreie sigma -form von 2-(4-(2-furoyl-(2-piperazin)-1-yl)-4-amino-6,7-dimethoxychinazolinhydrochlorid und verfahren zu ihrer herstellung.
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
JP2652272B2 (ja) *	1990-12-31	1997-09-10	住化ファインケム株式会社	１−（４−アミノ−６，７−ジメトキシ−２−キナゾリニル）−４−（２−テトラヒドロフロイル）ピペラジン塩酸塩の新規な結晶体および該結晶体の製造方法
GB9417310D0 (en) *	1994-08-27	1994-10-19	Pfizer Ltd	Therapeutic agents
US5952003A (en) *	1996-08-01	1999-09-14	Novartis Corporation	Terazosin capsules
EP0849264A1 (de) *	1996-12-20	1998-06-24	HEUMANN PHARMA GmbH	Neue polymorphe Form von doxazosinmesylat (Form I)
EP0849265A1 (de) *	1996-12-20	1998-06-24	HEUMANN PHARMA GmbH	Neue polymorphe Form von Doxazosin-Mesylat (Form II)
EP0849266B8 (de) *	1996-12-20	2007-10-03	Heumann PCS GmbH	Neue polymorphe Form von Doxazosinmesylat (Form III)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3635979A (en) *	1969-09-29	1972-01-18	Pfizer	Certain 6- and/or 7-alkoxy-substituted-2 4-bis(disubstituted amino) quinazolines

1976
- 1976-03-01 US US05/662,937 patent/US4092315A/en not_active Expired - Lifetime
1977
- 1977-02-11 GB GB5756/77A patent/GB1538713A/en not_active Expired
- 1977-02-14 SE SE7701624A patent/SE423234B/sv not_active IP Right Cessation
- 1977-02-16 ZA ZA770918A patent/ZA77918B/xx unknown
- 1977-02-17 IL IL51481A patent/IL51481A/xx unknown
- 1977-02-18 CA CA272,080A patent/CA1068269A/en not_active Expired
- 1977-02-18 AU AU22443/77A patent/AU506937B2/en not_active Expired
- 1977-02-23 YU YU499/77A patent/YU41294B/xx unknown
- 1977-02-24 PT PT66227A patent/PT66227B/pt unknown
- 1977-02-24 IE IE399/77A patent/IE44522B1/en not_active IP Right Cessation
- 1977-02-25 DE DE2708192A patent/DE2708192C3/de not_active Expired
- 1977-02-28 FR FR7705819A patent/FR2372828A1/fr active Granted
- 1977-02-28 SU SU772457100A patent/SU644387A3/ru active
- 1977-02-28 HU HU76UO128A patent/HU173641B/hu unknown
- 1977-02-28 FI FI770634A patent/FI62082C/fi not_active IP Right Cessation
- 1977-02-28 BE BE1007976A patent/BE851878A/xx not_active IP Right Cessation
- 1977-02-28 NO NO770674A patent/NO146499C/no unknown
- 1977-02-28 NL NLAANVRAGE7702123,A patent/NL169591C/xx not_active IP Right Cessation
- 1977-02-28 ES ES545368A patent/ES8707447A1/es not_active Expired
- 1977-02-28 DK DK86877A patent/DK145858C/da not_active IP Right Cessation
- 1977-02-28 JP JP52021433A patent/JPS604188B2/ja not_active Expired
- 1977-02-28 NZ NZ183450A patent/NZ183450A/xx unknown
- 1977-03-01 PL PL1977196354A patent/PL105559B1/pl not_active IP Right Cessation
- 1977-03-01 AR AR266724A patent/AR210937A1/es active
- 1977-03-01 CS CS771358A patent/CS191332B2/cs unknown
- 1977-03-01 DD DD7700197618A patent/DD129652A5/xx unknown
- 1977-03-01 RO RO7789566A patent/RO73095A/ro unknown
- 1977-03-01 LU LU76868A patent/LU76868A1/xx unknown
- 1977-03-01 CH CH255577A patent/CH618436A5/fr not_active IP Right Cessation
- 1977-03-01 BG BG7735558A patent/BG29724A3/xx unknown
1981
- 1981-07-02 HK HK308/81A patent/HK30881A/xx unknown
- 1981-12-30 MY MY271/81A patent/MY8100271A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9976252B2 (en)	2014-07-21	2018-05-22	Keir Manufacturing, Inc.	Aerodynamic flyer bow

Also Published As

Publication number	Publication date
AU2244377A (en)	1978-11-23
FI62082B (fi)	1982-07-30
ES8707447A1 (es)	1987-08-16
FR2372828B1 (sv)	1980-02-01
FI62082C (fi)	1982-11-10
NZ183450A (en)	1979-03-16
PL105559B1 (pl)	1979-10-31
YU49977A (en)	1983-12-31
FI770634A (sv)	1977-09-02
GB1538713A (en)	1979-01-24
NL7702123A (nl)	1977-09-05
ES545368A0 (es)	1978-06-01
IE44522B1 (en)	1981-12-30
YU41294B (en)	1987-02-28
NO146499B (no)	1982-07-05
PT66227A (en)	1977-03-01
SU644387A3 (ru)	1979-01-25
NL169591C (nl)	1982-08-02
AU506937B2 (en)	1980-01-31
DE2708192B2 (de)	1979-08-02
BG29724A3 (en)	1981-01-15
JPS52105206A (en)	1977-09-03
SE423234B (sv)	1982-04-26
DE2708192A1 (de)	1977-09-08
PT66227B (en)	1978-07-14
SE7701624L (sv)	1977-09-02
AR210937A1 (es)	1977-09-30
CS191332B2 (en)	1979-06-29
NO770674L (no)	1977-09-02
LU76868A1 (sv)	1977-09-21
IL51481A (en)	1980-09-16
HU173641B (en)	1979-07-28
NL169591B (nl)	1982-03-01
DK145858C (da)	1983-09-12
DD129652A5 (de)	1978-02-01
JPS604188B2 (ja)	1985-02-01
CA1068269A (en)	1979-12-18
ZA77918B (en)	1977-12-28
HK30881A (en)	1981-07-10
MY8100271A (en)	1981-12-31
IL51481A0 (en)	1977-04-29
DK86877A (da)	1977-09-02
DE2708192C3 (de)	1980-05-08
PL196354A1 (pl)	1978-02-27
FR2372828A1 (fr)	1978-06-30
IE44522L (en)	1977-09-01
BE851878A (fr)	1977-08-29
DK145858B (da)	1983-03-21
RO73095A (ro)	1981-06-26
US4092315A (en)	1978-05-30
NO146499C (no)	1982-10-13

Legal Events

Date	Code	Title	Description
1997-03-27	PL	Patent ceased

Publication	Publication Date	Title
CH618436A5 (sv)	1980-07-31
BE1004229A5 (fr)	1992-10-13	Agents pharmaceutiques.
JP6720280B2 (ja)	2020-07-08	新規アベキシノスタット塩、関連結晶形態、それらの調製方法およびそれらを含有する医薬組成物
TWI427083B (zh)	2014-02-21	巨環內酯固態形式
RU2686722C1 (ru)	2019-04-30	Новые кристаллы урацильного соединения
FR2513250A1 (fr)	1983-03-25	Nouvelles cyclobutene-3,4-diones substituees
FR2730232A1 (fr)	1996-08-09	Anhydrate de chlorhydrate de paroxetine pratiquement depourvu de propane-2-ol lie, son application en therapeutique
LU83661A1 (fr)	1983-06-08	Derive d'aminoalcoyl furanne,procede pour sa preparation et composition pharmaceutique comprenant ce derive
RU2370489C2 (ru)	2009-10-20	Кристаллическая форма хинолинового соединения и способ получения данного соединения в указанной форме
CA3038726A1 (fr)	2018-04-05	Composition comprenant au moins un sel pharmaceutiquement acceptable d'elafibranor soluble en milieux aqueux presentant une absorption intestinale amelioree
LU82105A1 (fr)	1980-08-08	Trans-5-aryl-2,3,4,4a-5-9b-hexahydro-1h-pyrido(4,3-b)indoles substitues en position 2 dextrogyres, procedes et composes intermediaires permettant de les obtenir et composition pharmaceutique les contenant
KR102442536B1 (ko)	2022-09-13	리나글립틴 결정형 및 이의 제조방법
EP3199529A1 (en)	2017-08-02	Salt of dicarboxylic acid compound
CN105566314A (zh)	2016-05-11	一种盐酸替扎尼定化合物
US20080070989A1 (en)	2008-03-20	Method of Evaluating Evenness of Suplatast Tosilate Crystal, Even Crystal, and Process for Producing the Same
CA3038727A1 (fr)	2018-04-05	Sel de metformine d'elafibranor presentant une activite duale pour le traitement de l'obesite associee a la steato-hepatite non alcoolique (nash) et a l'hypertriglyceridemie
EP1682124B1 (fr)	2007-12-19	Compositions pharmaceutiques a base de sel d'idazoxan ou d´un de ses polymorphes
NL1014634C1 (nl)	2000-08-03	Zolpidemzouten.
EP0236646A1 (fr)	1987-09-16	Nouveaux ortho-anisamides, leur procédé d'obtention et leurs applications thérapeutiques
JP5792318B2 (ja)	2015-10-07	ブロムフェナク有機塩、ならびにその製造方法、組成物および使用
FR2849852A1 (fr)	2004-07-16	Formes d'ondansetron et procede pour leur preparation
SK7362002A3 (en)	2003-02-04	Solid pharmaceutical preparation
EA045430B1 (ru)	2023-11-24	Композиция, содержащая гидрат безилата левамлодипина, и способ ее получения
EP0384088A1 (fr)	1990-08-29	La (+) 1-[(3,4,5-triméthoxy) benzyloxyméthyl]-1-phényl-N,N-diméthyl-n-propylamine, son procédé de préparation et son application en thérapeutique
KR810000956B1 (ko)	1981-08-24	프라조신 염산염의 α형의 제조방법

CH618436A5 - - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=24659839

Family Applications (1)

Country Status (32)

Cited By (1)

Families Citing this family (16)

Family Cites Families (1)

Cited By (1)

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