NO772230L - Fremgangsm}te ved fremstilling av carbostyriler - Google Patents

Fremgangsm}te ved fremstilling av carbostyriler

Info

Publication number: NO772230L
Authority: NO; Norway
Prior art keywords: ethyl; trifluoromethyl; carbon atoms; alkyl; trifluoro
Prior art date: 1976-06-24

Application number

NO772230A

Other languages

English (en)

Norwegian (no)

Inventor

Paul Edward Aldrich

Gilbert Harvey 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.)

1976-06-24

Filing date

1977-06-23

Publication date

1977-12-28

1977-06-23 Application filed by Du Pont filed Critical Du Pont

1977-12-28 Publication of NO772230L publication Critical patent/NO772230L/no

Links

238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 15
150000001875 compounds Chemical class 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
150000001408 amides Chemical class 0.000 claims description 8
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
NATWWTXZPXMEGM-UHFFFAOYSA-N 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-6-methyl-4h-pyrrolo[3,2,1-ij]quinolin-4-one Chemical compound C1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC3=C2N1C(=O)C=C3C NATWWTXZPXMEGM-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
FDOILHPYUIAXBU-UHFFFAOYSA-N 2,3-dihydro-7-ethyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-1h,5h-benzo[ij]quinolizin-5-one Chemical compound C1CCC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC3=C2N1C(=O)C=C3CC FDOILHPYUIAXBU-UHFFFAOYSA-N 0.000 claims description 3
ITENIXALZSVNTO-UHFFFAOYSA-N 6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2,9-dimethyl-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,9-tetraen-11-one Chemical compound CC1=CC(=O)N2C(C)CC3=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC1=C32 ITENIXALZSVNTO-UHFFFAOYSA-N 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
MRXRBJQTNLOYTF-UHFFFAOYSA-N 2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-7-methyl-1h,5h-benzo[ij]quinolizin-5-one Chemical compound C1CCC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC3=C2N1C(=O)C=C3C MRXRBJQTNLOYTF-UHFFFAOYSA-N 0.000 claims description 2
VNDAPQBOWKYXNS-UHFFFAOYSA-N 7-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,12-dimethyl-1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13)-tetraen-2-one Chemical compound CC1=CC(=O)N2C(C)CCC3=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC1=C32 VNDAPQBOWKYXNS-UHFFFAOYSA-N 0.000 claims description 2
JRYHWGZEAXYOLZ-UHFFFAOYSA-N 9-ethyl-6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,9-tetraen-11-one Chemical compound C1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC3=C2N1C(=O)C=C3CC JRYHWGZEAXYOLZ-UHFFFAOYSA-N 0.000 claims 1
229940100198 alkylating agent Drugs 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
238000010992 reflux Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
-1 aromatic carboxylic acids Chemical class 0.000 description 16
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
239000011343 solid material Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000007858 starting material Substances 0.000 description 7
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
206010020772 Hypertension Diseases 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
239000002775 capsule Substances 0.000 description 6
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000007363 ring formation reaction 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
241000700159 Rattus Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000002220 antihypertensive agent Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
229940030600 antihypertensive agent Drugs 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000001631 hypertensive effect Effects 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
239000002243 precursor Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
SBWJGPICKZXXOG-UHFFFAOYSA-N 1-benzyl-2,3-dihydroindole Chemical compound C1CC2=CC=CC=C2N1CC1=CC=CC=C1 SBWJGPICKZXXOG-UHFFFAOYSA-N 0.000 description 3
PRRBQHNMYJRHFW-UHFFFAOYSA-M 3-oxoheptanoate Chemical compound CCCCC(=O)CC([O-])=O PRRBQHNMYJRHFW-UHFFFAOYSA-M 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229960004486 desoxycorticosterone acetate Drugs 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
238000000746 purification Methods 0.000 description 3
VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 3
UZKSRKCOYCBLGN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(1,2,3,4-tetrahydroquinolin-6-yl)propan-2-ol Chemical compound N1CCCC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C21 UZKSRKCOYCBLGN-UHFFFAOYSA-N 0.000 description 2
VAIZVCMDJPBJCM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;trihydrate Chemical compound O.O.O.FC(F)(F)C(=O)C(F)(F)F.FC(F)(F)C(=O)C(F)(F)F VAIZVCMDJPBJCM-UHFFFAOYSA-N 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007891 compressed tablet Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003480 eluent Substances 0.000 description 2
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000010534 mechanism of action Effects 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
102220012898 rs397516346 Human genes 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000004873 systolic arterial blood pressure Effects 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
ASDVIYGKBACHLO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(2,3,4,5-tetrahydro-1h-1-benzazepin-7-yl)propan-2-ol Chemical compound N1CCCCC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C21 ASDVIYGKBACHLO-UHFFFAOYSA-N 0.000 description 1
VJBLELFBVBDBHY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1h-indol-5-yl)propan-2-ol Chemical compound FC(F)(F)C(O)(C(F)(F)F)C1=CC=C2NC(C)CC2=C1 VJBLELFBVBDBHY-UHFFFAOYSA-N 0.000 description 1
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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
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO772230A 1976-06-24 1977-06-23 Fremgangsm}te ved fremstilling av carbostyriler NO772230L (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US69958876A	1976-06-24	1976-06-24
US69958776A	1976-06-24	1976-06-24
US79371177A	1977-05-06	1977-05-06
US79371277A	1977-05-06	1977-05-06

Publications (1)

Publication Number	Publication Date
NO772230L true NO772230L (no)	1977-12-28

Family

ID=27505478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO772230A NO772230L (no)	1976-06-24	1977-06-23	Fremgangsm}te ved fremstilling av carbostyriler

Country Status (17)

Country	Link
JP (1)	JPS5323983A (fr)
AR (1)	AR224334A1 (fr)
BE (1)	BE856024A (fr)
DE (1)	DE2728029A1 (fr)
DK (1)	DK279777A (fr)
ES (1)	ES460080A1 (fr)
FI (1)	FI771977A7 (fr)
FR (2)	FR2355828A1 (fr)
GB (1)	GB1583249A (fr)
GR (1)	GR63361B (fr)
IE (1)	IE45227B1 (fr)
IL (1)	IL52378A (fr)
LU (1)	LU77609A1 (fr)
NL (1)	NL7707062A (fr)
NO (1)	NO772230L (fr)
NZ (1)	NZ184458A (fr)
SE (1)	SE7707303L (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4251659A (en) *	1977-12-22	1981-02-17	E. I. Du Pont De Nemours And Company	Polyfluorohydroxyisopropyl-heterocyclic compounds
ZA786261B (en) *	1977-12-22	1979-10-31	Du Pont	Carbostyrils
US4322417A (en) *	1977-12-22	1982-03-30	E. I. Du Pont De Nemours And Company	Antihypertensive polyfluoroisopropyl tricyclic carbostyrils
US4251534A (en) *	1977-12-22	1981-02-17	E. I. Du Pont De Nemours And Company	Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
PT1756096E (pt)	2004-05-03	2009-10-16	Hoffmann La Roche	Derivados de indolilo como moduladores do receptor x do fígado
MX383020B (es) *	2014-10-01	2025-03-13	Henkel Ag & Co Kgaa	Aceleradores de curado para composiciones curables anaerobicas.

1977
- 1977-06-20 GR GR53749A patent/GR63361B/el unknown
- 1977-06-20 IE IE1250/77A patent/IE45227B1/en unknown
- 1977-06-22 DE DE19772728029 patent/DE2728029A1/de not_active Withdrawn
- 1977-06-22 AR AR268155A patent/AR224334A1/es active
- 1977-06-22 NZ NZ184458A patent/NZ184458A/xx unknown
- 1977-06-23 NO NO772230A patent/NO772230L/no unknown
- 1977-06-23 DK DK279777A patent/DK279777A/da unknown
- 1977-06-23 GB GB26355/77A patent/GB1583249A/en not_active Expired
- 1977-06-23 SE SE7707303A patent/SE7707303L/xx not_active Application Discontinuation
- 1977-06-23 ES ES460080A patent/ES460080A1/es not_active Expired
- 1977-06-23 BE BE178704A patent/BE856024A/fr unknown
- 1977-06-23 FR FR7719247A patent/FR2355828A1/fr not_active Withdrawn
- 1977-06-23 FI FI771977A patent/FI771977A7/fi not_active Application Discontinuation
- 1977-06-23 IL IL52378A patent/IL52378A/xx unknown
- 1977-06-24 LU LU77609A patent/LU77609A1/xx unknown
- 1977-06-24 JP JP7603677A patent/JPS5323983A/ja active Pending
- 1977-06-24 NL NL7707062A patent/NL7707062A/xx not_active Application Discontinuation
1978
- 1978-03-17 FR FR7807798A patent/FR2372809A1/fr active Granted

Also Published As

Publication number	Publication date
ES460080A1 (es)	1978-10-01
SE7707303L (sv)	1977-12-25
LU77609A1 (fr)	1978-02-01
FR2372809A1 (fr)	1978-06-30
GR63361B (en)	1979-10-22
DK279777A (da)	1977-12-25
IE45227B1 (en)	1982-07-14
IL52378A (en)	1981-01-30
BE856024A (fr)	1977-12-23
JPS5323983A (en)	1978-03-06
NL7707062A (nl)	1977-12-28
IL52378A0 (en)	1977-08-31
DE2728029A1 (de)	1978-01-05
NZ184458A (en)	1979-12-11
GB1583249A (en)	1981-01-21
FR2355828A1 (fr)	1978-01-20
IE45227L (en)	1977-12-24
FR2372809B1 (fr)	1981-07-24
AR224334A1 (es)	1981-11-30
FI771977A7 (fr)	1977-12-25

Publication	Publication Date	Title
SU1251801A3 (ru)	1986-08-15	Способ получени 2-замещенных 4-амино-6,7-диметоксихинолинов или их фармацевтически приемлемых солей
US5652246A (en)	1997-07-29	Piperidine compounds
US3950343A (en)	1976-04-13	Pyrroloisoquinoline derivatives
NO301421B1 (no)	1997-10-27	Analogifremgangsmåte for fremstilling av terapeutisk aktive, heterocykliske aminer
WO2014026657A2 (fr)	2014-02-20	Procédé pour la préparation d'un dérivé d'acide 2-méthyl-2'-phénylpropionique utilisant de nouveaux intermédiaires
WO1993012786A1 (fr)	1993-07-08	Derives d'indolinone
NO154883B (no)	1986-09-29	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 2-acylaminomethyl-1,4-benzodiazepiner.
US5216018A (en)	1993-06-01	Hydroisoindolines and hydroisoquinolines as psychotropic
CA2724219C (fr)	2016-04-05	5- [5- [2- (3, 5-bis (trifluoromethyl) phenyl) -2-methylpropanoylmethylamino] -4- (4-fluoro-2-methylphenyl) ] -2-pyridinyl-2-alkyl-prolinamide, antagonistes du recepteur nk1
JPH0311067A (ja)	1991-01-18	興奮性アミノ酸拮抗剤
AU2009232836A1 (en)	2009-10-08	Indolinone compound
US4218448A (en)	1980-08-19	Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
NO161738B (no)	1989-06-12	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolinderivater.
MXPA02006699A (es)	2005-08-16	Nuevos compuestos de octahidro-2h-pirod[1,2-a]pirazina, un proceso para su preparacion y composiciones farmaceuticas que los contienen.
GB1583249A (en)	1981-01-21	Carbostyrils
DK169581B1 (da)	1994-12-12	5,6,7,8-tetrahydro-beta-carbolinderivater og fremgangsmåde til deres fremstilling
NO168820B (no)	1991-12-30	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzazepin-derivater
AU671814B2 (en)	1996-09-12	Nitroquinolone derivatives as NMDA antagonists
US4482714A (en)	1984-11-13	Pyrazino[2',3'-3,4]pyrido[1,2-a]indole derivatives
Chupakhin et al.	2010	Asymmetric induction in the reactions of azinones with C-nucleophiles
AU749935B2 (en)	2002-07-04	Acridin derivatives
Fujiwara et al.	1969	Ellipticine analogs: Oxygen and sulfur isosteres
EP0220873B1 (fr)	1993-11-24	Imides bicycliques condensées à activité psychotrope
JP2003513006A (ja)	2003-04-08	三環性鎮痛薬
US4515949A (en)	1985-05-07	[2-(1H-indol-1-yl)ethyl]-2-piperazine and pyrido[1,2-a]indol-9-one as intermediates for pyrazino(2,3-3,4)pyrido(1,2-a) indoles which are useful for treating hypertension in mammals