LU80720A1 - Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant - Google Patents

Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant Download PDF

Info

Publication number: LU80720A1
Authority: LU; Luxembourg
Prior art keywords: methyl; group; hydroxy; hydrogen; trifluoro
Prior art date: 1977-12-22

Application number

LU80720A

Other languages

English (en)

French (fr)

Inventor

P Aldrich

G Berezin

Original Assignee

Du Pont

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.)

1977-12-22

Filing date

1978-12-22

Publication date

1980-01-22

1978-12-22 Application filed by Du Pont filed Critical Du Pont

1980-01-22 Publication of LU80720A1 publication Critical patent/LU80720A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 43
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
238000000034 method Methods 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
-1 trifluoro-1 -hydroxy-1 - (trifluoromethyl) ethyl Chemical group 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
150000001408 amides Chemical class 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
206010020772 Hypertension Diseases 0.000 claims description 7
230000003276 anti-hypertensive effect Effects 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 61
239000000047 product Substances 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
150000001412 amines Chemical class 0.000 description 15
230000008018 melting Effects 0.000 description 15
238000002844 melting Methods 0.000 description 15
239000004480 active ingredient Substances 0.000 description 14
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 10
239000002904 solvent Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000011343 solid material Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000001350 alkyl halides Chemical class 0.000 description 7
238000001914 filtration Methods 0.000 description 7
PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical class C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 6
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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125000002619 bicyclic group Chemical group 0.000 description 6
239000002775 capsule Substances 0.000 description 6
238000010828 elution Methods 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
239000013256 coordination polymer Substances 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000007792 addition Methods 0.000 description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000000605 extraction Methods 0.000 description 4
IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QAPXLUZMMFIIBI-UHFFFAOYSA-N 1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)F QAPXLUZMMFIIBI-UHFFFAOYSA-N 0.000 description 3
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000003054 catalyst Substances 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
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 3
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239000007924 injection Substances 0.000 description 3
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239000008101 lactose Substances 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
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VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
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CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
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VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
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229940030600 antihypertensive agent Drugs 0.000 description 2
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230000008901 benefit Effects 0.000 description 2
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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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 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
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
244000290333 Vanilla fragrans Species 0.000 description 1
235000009499 Vanilla fragrans Nutrition 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UPBWIICFGYMCPC-UHFFFAOYSA-N bis(2-methoxyethoxy)aluminum Chemical compound COCCO[Al]OCCOC UPBWIICFGYMCPC-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
230000036541 health Effects 0.000 description 1
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
230000009097 homeostatic mechanism Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
AHVVNJKTHNOYED-UHFFFAOYSA-N propan-2-one;trihydrate Chemical compound O.O.O.CC(C)=O.CC(C)=O AHVVNJKTHNOYED-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
239000012264 purified product Substances 0.000 description 1
VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 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
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Quinoline Compounds (AREA)

LU80720A 1977-12-22 1978-12-22 Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant LU80720A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/863,269 US4251534A (en)	1977-12-22	1977-12-22	Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
US86326977		1977-12-22

Publications (1)

Publication Number	Publication Date
LU80720A1 true LU80720A1 (fr)	1980-01-22

Family

ID=25340730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80720A LU80720A1 (fr)	1977-12-22	1978-12-22	Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant

Country Status (11)

Country	Link
US (1)	US4251534A (da)
JP (1)	JPS5498780A (da)
BE (1)	BE872956A (da)
CA (1)	CA1099712A (da)
DE (1)	DE2854727A1 (da)
DK (1)	DK574978A (da)
FR (1)	FR2412533A1 (da)
GB (1)	GB2010821B (da)
IT (1)	IT1102419B (da)
LU (1)	LU80720A1 (da)
NL (1)	NL7812422A (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4499108A (en) *	1983-06-08	1985-02-12	Schering Corporation	Stable pleasant-tasting albuterol sulfate pharmaceutical formulations
US5622965A (en) *	1993-03-12	1997-04-22	State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon	4-hydroxy-3-nitro-1,2-dihydroquinolin-2-ones and the use thereof as excitatory amino acid and glycine receptor antagonists
US6316503B1 (en) *	1999-03-15	2001-11-13	Tularik Inc.	LXR modulators
JP4434744B2 (ja) *	2002-01-30	2010-03-17	アムジェンインコーポレイテッド	アリールスルホンアミドベンジル化合物
CA2474702A1 (en) *	2002-01-30	2003-08-07	Tularik Inc	Heterocyclic arylsulfonamidobenzylic compounds
MXPA06001566A (es) *	2003-08-12	2006-05-15	Amgen Inc	Compuestos arilsulfonamidobencilicos.
GB201721964D0 (en) *	2017-12-27	2018-02-07	Bp Oil Int	Methods for preparing fuel additives
GB201721967D0 (en) *	2017-12-27	2018-02-07	Bp Oil Int	Methods for preparing fuel additives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR980098A (fr) *	1948-12-10	1951-05-08		Poignée protectrice à usages ménagers
US3178348A (en) *	1961-02-08	1965-04-13	Norwich Pharma Co	Hypotensive quinolines
DE1216878B (de) *	1963-04-02	1966-05-18	Cassella Farbwerke Mainkur Ag	Verfahren zur Herstellung von coronargefaesserweiternden Derivaten des 7-Hydroxy-2-oxo-1, 2-dihydrochinolins
US4058612A (en) *	1974-12-02	1977-11-15	Schering Corporation	6-(Polyhaloisopropyl)quinazoline-2,4-diones
GR63361B (en) *	1976-06-24	1979-10-22	Du Pont	Preparation process of antihypertensive hexafluorohydroxyisopropyl bicyclic and tricyclic carbostyrils

1977
- 1977-12-22 US US05/863,269 patent/US4251534A/en not_active Expired - Lifetime
1978
- 1978-12-19 DE DE19782854727 patent/DE2854727A1/de not_active Withdrawn
- 1978-12-20 CA CA318,285A patent/CA1099712A/en not_active Expired
- 1978-12-21 IT IT31170/78A patent/IT1102419B/it active
- 1978-12-21 NL NL7812422A patent/NL7812422A/xx not_active Application Discontinuation
- 1978-12-21 FR FR7835956A patent/FR2412533A1/fr active Granted
- 1978-12-21 BE BE192471A patent/BE872956A/xx unknown
- 1978-12-21 DK DK574978A patent/DK574978A/da not_active Application Discontinuation
- 1978-12-21 GB GB7849684A patent/GB2010821B/en not_active Expired
- 1978-12-22 JP JP15840178A patent/JPS5498780A/ja active Pending
- 1978-12-22 LU LU80720A patent/LU80720A1/fr unknown

Also Published As

Publication number	Publication date
US4251534A (en)	1981-02-17
JPS5498780A (en)	1979-08-03
CA1099712A (en)	1981-04-21
FR2412533A1 (fr)	1979-07-20
GB2010821B (en)	1982-08-11
BE872956A (fr)	1979-06-21
NL7812422A (nl)	1979-06-26
IT1102419B (it)	1985-10-07
DK574978A (da)	1979-06-23
GB2010821A (en)	1979-07-04
DE2854727A1 (de)	1979-06-28
FR2412533B1 (da)	1981-10-02
IT7831170A0 (it)	1978-12-21

Publication	Publication Date	Title
EP0074304B1 (fr)	1985-04-03	Ethers tricycliques, leur préparation et les compositions pharmaceutiques les contenant
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EP0833818A1 (fr)	1998-04-08	Composes agonistes du recepteur cb 2?
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BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
FR2552759A1 (fr)	1985-04-05	Composes de la 1,2,4-triazolone et leur application pharmacologique
CA2055326A1 (fr)	1992-05-15	Derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0467325A2 (en)	1992-01-22	Carbostyril derivatives
EP0041410B1 (fr)	1983-11-09	Nouveaux éthers tricycliques, leurs procédés de préparation et leur utilisation comme médicament
MC1706A1 (fr)	1986-09-22	Dérivés de tétrahydronaphtalène
LU80720A1 (fr)	1980-01-22	Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant
EP0410834A1 (fr)	1991-01-30	Médicaments à base de dérivés de benzoxadiazine-4, 1, 2 nouveaux dérivés et leurs procédés de préparation
EP0269599B1 (fr)	1993-12-15	1H-Imidazoles substitués
EP0239461A1 (fr)	1987-09-30	Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique
FR2584713A1 (fr)	1987-01-16	Nouveaux derives de l'indole carboxamide, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant
JPH06135958A (ja)	1994-05-17	ベンゾシクロヘプテン誘導体及びその製法
FR2612517A1 (fr)	1988-09-23	Derives de benzoxazine, procedes de preparation de ces derives et compositions pharmaceutiques les contenant
CA2318381C (fr)	2007-04-17	Nouveaux composes tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA2144288A1 (fr)	1995-09-12	Composes alkylaminoindanes, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
FR2600647A1 (fr)	1987-12-31	Derives de la glycine
FR2599033A1 (fr)	1987-11-27	Derives des 3-(hydroxymethyl)-isoquinoleine, procede pour les preparer et compositions pharmaceutiques les contenant
LU80712A1 (fr)	1980-01-22	Composes polyfluorohydroxyisopropyl carbostyriles tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant
EP0027759B1 (fr)	1983-10-12	Nouveaux dérivés spiranniques, procédé pour leur préparation, et médicaments les contenant