NO782590L - Analogifremgangsmaate for fremstilling av fysiologisk aktive isokinolindioner - Google Patents

Analogifremgangsmaate for fremstilling av fysiologisk aktive isokinolindioner

Info

Publication number: NO782590L
Authority: NO; Norway
Prior art keywords: isoquinoline; dione; dimethyl; general formula; methyl
Prior art date: 1977-07-29

Application number

NO782590A

Other languages

English (en)

Norwegian (no)

Inventor

Volkhard Austel

Eberhard Kutter

Wolfgang Eberlein

Joachim Heider

Joachim Kaehling

Original Assignee

Thomae Gmbh Dr K

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.)

1977-07-29

Filing date

1978-07-28

Publication date

1979-01-30

1978-07-28 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1979-01-30 Publication of NO782590L publication Critical patent/NO782590L/no

Links

238000002360 preparation method Methods 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 20
QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
-1 isoquinoline ions Chemical class 0.000 claims description 8
GHBMEVJVGOKHTG-UHFFFAOYSA-N 4,4-dimethyl-2-(2-methylsulfanylethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCSC)C(=O)C2=C1 GHBMEVJVGOKHTG-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
WIHRQMOQRJCTDT-UHFFFAOYSA-N 4,4-dimethyl-2-(methylsulfanylmethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CSC)C(=O)C2=C1 WIHRQMOQRJCTDT-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
UAMYRUITJFKHSJ-UHFFFAOYSA-N 4,4-dimethyl-2-(2-methylsulfinylethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCS(=O)C)C(=O)C2=C1 UAMYRUITJFKHSJ-UHFFFAOYSA-N 0.000 claims description 4
REURBNYRMMOQKT-UHFFFAOYSA-N 4,4-dimethyl-2-(methylsulfinylmethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CS(=O)C)C(=O)C2=C1 REURBNYRMMOQKT-UHFFFAOYSA-N 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
150000001447 alkali salts Chemical class 0.000 claims description 4
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
150000003568 thioethers Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
239000005977 Ethylene Substances 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 14
239000012362 glacial acetic acid Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
CQNOBDWLOTVSNG-UHFFFAOYSA-N 4,4-dimethyl-2-(propan-2-ylsulfanylmethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CSC(C)C)C(=O)C2=C1 CQNOBDWLOTVSNG-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
241000699670 Mus sp. Species 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
230000001773 anti-convulsant effect Effects 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
IIJJBPDTZWMQIZ-UHFFFAOYSA-N 4,4-dimethyl-2-(2-methylsulfonylethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCS(C)(=O)=O)C(=O)C2=C1 IIJJBPDTZWMQIZ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 2
BIURWDFQAUMXLF-UHFFFAOYSA-N 2-(4-butylsulfanylbutyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCCCSCCCC)C(=O)C2=C1 BIURWDFQAUMXLF-UHFFFAOYSA-N 0.000 description 2
VSRVOIDBBCKMTM-UHFFFAOYSA-N 4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)NC(=O)C2=C1 VSRVOIDBBCKMTM-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
210000003141 lower extremity Anatomy 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
UZQIUFUPKNBGCL-UHFFFAOYSA-N 2-(2-ethylsulfanylethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCSCC)C(=O)C2=C1 UZQIUFUPKNBGCL-UHFFFAOYSA-N 0.000 description 1
CTTVVOJAUHPQFP-UHFFFAOYSA-N 2-(2-ethylsulfinylethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCS(=O)CC)C(=O)C2=C1 CTTVVOJAUHPQFP-UHFFFAOYSA-N 0.000 description 1
RYICLTHCQARAID-UHFFFAOYSA-N 2-(2-ethylsulfonylethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCS(=O)(=O)CC)C(=O)C2=C1 RYICLTHCQARAID-UHFFFAOYSA-N 0.000 description 1
BZAXRGAWYOMMCL-UHFFFAOYSA-N 2-(4-butylsulfinylbutyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCCCS(=O)CCCC)C(=O)C2=C1 BZAXRGAWYOMMCL-UHFFFAOYSA-N 0.000 description 1
NWARHIRYFAQXOG-UHFFFAOYSA-N 2-(4-chlorobutyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCCCCl)C(=O)C2=C1 NWARHIRYFAQXOG-UHFFFAOYSA-N 0.000 description 1
ASOIMKJWZACAIK-UHFFFAOYSA-N 2-(chloromethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCl)C(=O)C2=C1 ASOIMKJWZACAIK-UHFFFAOYSA-N 0.000 description 1
WWHIALAOGMWFDZ-UHFFFAOYSA-N 2-(ethylsulfanylmethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CSCC)C(=O)C2=C1 WWHIALAOGMWFDZ-UHFFFAOYSA-N 0.000 description 1
VNGLDRWNCGKORX-UHFFFAOYSA-N 2-(ethylsulfinylmethyl)-4,4-dimethylisoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CS(=O)CC)C(=O)C2=C1 VNGLDRWNCGKORX-UHFFFAOYSA-N 0.000 description 1
NPHULPIAPWNOOH-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(2,3-dihydroindol-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCC2=CC=CC=C12 NPHULPIAPWNOOH-UHFFFAOYSA-N 0.000 description 1
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
JGFAOYCNFVLZOW-UHFFFAOYSA-N 4,4-dimethyl-2-(2-propylsulfanylethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCSCCC)C(=O)C2=C1 JGFAOYCNFVLZOW-UHFFFAOYSA-N 0.000 description 1
HIFYLSDYOVCIPX-UHFFFAOYSA-N 4,4-dimethyl-2-(2-propylsulfonylethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCS(=O)(=O)CCC)C(=O)C2=C1 HIFYLSDYOVCIPX-UHFFFAOYSA-N 0.000 description 1
WNOBBEXTYLPNMY-UHFFFAOYSA-N 4,4-dimethyl-2-(3-propan-2-ylsulfanylpropyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCCSC(C)C)C(=O)C2=C1 WNOBBEXTYLPNMY-UHFFFAOYSA-N 0.000 description 1
QOUAYESJTGAPEQ-UHFFFAOYSA-N 4,4-dimethyl-2-(3-propan-2-ylsulfinylpropyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCCS(=O)C(C)C)C(=O)C2=C1 QOUAYESJTGAPEQ-UHFFFAOYSA-N 0.000 description 1
AGWCALGZDWRLJW-UHFFFAOYSA-N 4,4-dimethyl-2-(propan-2-ylsulfinylmethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CS(=O)C(C)C)C(=O)C2=C1 AGWCALGZDWRLJW-UHFFFAOYSA-N 0.000 description 1
CWJSDWKPLWSESA-UHFFFAOYSA-N 4,4-dimethyl-2-(propan-2-ylsulfonylmethyl)isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C)(C)C(=O)N(CS(=O)(=O)C(C)C)C(=O)C2=C1 CWJSDWKPLWSESA-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
241000906446 Theraps Species 0.000 description 1
206010043994 Tonic convulsion Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
230000001148 spastic effect Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

NO782590A 1977-07-29 1978-07-28 Analogifremgangsmaate for fremstilling av fysiologisk aktive isokinolindioner NO782590L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772734222 DE2734222A1 (de)	1977-07-29	1977-07-29	Neue schwefelhaltige isochinolindione

Publications (1)

Publication Number	Publication Date
NO782590L true NO782590L (no)	1979-01-30

Family

ID=6015122

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782590A NO782590L (no)	1977-07-29	1978-07-28	Analogifremgangsmaate for fremstilling av fysiologisk aktive isokinolindioner

Country Status (18)

Country	Link
US (1)	US4179508A (fi)
JP (1)	JPS5427575A (fi)
AU (1)	AU3845478A (fi)
BE (1)	BE869366A (fi)
DE (1)	DE2734222A1 (fi)
DK (1)	DK335078A (fi)
ES (3)	ES471492A1 (fi)
FI (1)	FI782026A (fi)
FR (1)	FR2398735A1 (fi)
GB (1)	GB2002757A (fi)
IL (1)	IL55226A0 (fi)
IT (1)	IT1107655B (fi)
LU (1)	LU80044A1 (fi)
NL (1)	NL7808007A (fi)
NO (1)	NO782590L (fi)
PT (1)	PT68361A (fi)
SE (1)	SE7808244L (fi)
ZA (1)	ZA784289B (fi)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4230711A (en) *	1979-01-31	1980-10-28	Chevron Research Company	Fungicidal n-substituted 4,4-dialkyl homophthalimides
US4321254A (en) *	1980-09-26	1982-03-23	Smithkline Corporation	Antiallergic imidodisulfamides
JPS62183992A (ja) *	1986-02-10	1987-08-12	Mitsubishi Heavy Ind Ltd	レ−ザ加工装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3708486A (en) *	1969-04-17	1973-01-02	Boehringer Sohn Ingelheim	2-(p-(n'-cycloalkyl-carbamido-n-sulfonyl)-phenethyl)-1,2,3,4-tetrahydro-1,3-dioxo-4,4-dimethyl-isoquinolines and alkali metal salts thereof
DE2303483A1 (de) *	1973-01-25	1974-08-01	Basf Ag	Lactone der benzazaxanthenreihe und farbbildner fuer kopierverfahren

1977
- 1977-07-29 DE DE19772734222 patent/DE2734222A1/de active Pending
1978
- 1978-06-26 FI FI782026A patent/FI782026A/fi not_active Application Discontinuation
- 1978-07-06 ES ES471492A patent/ES471492A1/es not_active Expired
- 1978-07-18 US US05/925,877 patent/US4179508A/en not_active Expired - Lifetime
- 1978-07-20 IT IT50410/78A patent/IT1107655B/it active
- 1978-07-27 IL IL55226A patent/IL55226A0/xx unknown
- 1978-07-27 JP JP9099578A patent/JPS5427575A/ja active Pending
- 1978-07-27 LU LU80044A patent/LU80044A1/de unknown
- 1978-07-27 DK DK335078A patent/DK335078A/da unknown
- 1978-07-28 NL NL7808007A patent/NL7808007A/xx not_active Application Discontinuation
- 1978-07-28 ZA ZA784289A patent/ZA784289B/xx unknown
- 1978-07-28 GB GB7831613A patent/GB2002757A/en not_active Withdrawn
- 1978-07-28 AU AU38454/78A patent/AU3845478A/en active Pending
- 1978-07-28 PT PT68361A patent/PT68361A/pt unknown
- 1978-07-28 NO NO782590A patent/NO782590L/no unknown
- 1978-07-28 BE BE189581A patent/BE869366A/xx unknown
- 1978-07-28 FR FR7822498A patent/FR2398735A1/fr not_active Withdrawn
- 1978-07-28 SE SE7808244A patent/SE7808244L/xx unknown
- 1978-11-10 ES ES474973A patent/ES474973A1/es not_active Expired
- 1978-11-10 ES ES474974A patent/ES474974A1/es not_active Expired

Also Published As

Publication number	Publication date
ZA784289B (en)	1980-03-26
DE2734222A1 (de)	1979-02-15
GB2002757A (en)	1979-02-28
BE869366A (fr)	1979-01-29
ES474974A1 (es)	1979-05-01
ES474973A1 (es)	1979-05-01
US4179508A (en)	1979-12-18
IT1107655B (it)	1985-11-25
FI782026A (fi)	1979-01-30
DK335078A (da)	1979-01-30
ES471492A1 (es)	1979-01-16
AU3845478A (en)	1980-01-31
NL7808007A (nl)	1979-01-31
LU80044A1 (de)	1979-09-06
IL55226A0 (en)	1978-09-29
JPS5427575A (en)	1979-03-01
PT68361A (de)	1978-08-01
IT7850410A0 (it)	1978-07-20
FR2398735A1 (fr)	1979-02-23
SE7808244L (sv)	1979-01-30

Publication	Publication Date	Title
DK146339B (da)	1983-09-12	Analogifremgangsmaade til fremstilling af 5-(4-pyridyl)-6-(4-fluorphenyl)-2,3-dihydroimidazo-(2,1-b)-thiazolderivater
WO1995018127A1 (de)	1995-07-06	Aza-4-iminochinoline, verfahren zu ihrer herstellung und ihre verwendung
CA1312856C (en)	1993-01-19	6,16-dimethyl corticoids, their preparation and use
US4451471A (en)	1984-05-29	Certain 2,4,5-tri-substituted thiazoles, pharmaceutical compositions containing same and methods of using same
NO782590L (no)	1979-01-30	Analogifremgangsmaate for fremstilling av fysiologisk aktive isokinolindioner
CA1103245A (en)	1981-06-16	Process for the manufacture of novel oxadiazolopyrimidine derivatives
US8022203B2 (en)	2011-09-20	Amino derivatives of beta-homoandrostanes and beta-heteroandrostanes
NO169007B (no)	1992-01-20	Analogifremgangsmaate ved fremstilling av terapeutisk aktive uridinderivater
DE68924221T2 (de)	1996-02-15	Imidazolderivate.
CA1071187A (en)	1980-02-05	Acylated diepoxy-androstane and a process for the preparation thereof
US4634710A (en)	1987-01-06	Tricyclic imidazole derivatives
DK152427B (da)	1988-02-29	Analogifremgangsmaade til fremstilling af 4-thiomethylpyridinforbindelser eller farmaceutisk acceptable syreadditionssalte deraf
CA1037956A (en)	1978-09-05	Acyl derivatives of 5-mercaptopyridoxine and disulfide
NO149314B (no)	1983-12-19	Analogifremgangsmaate for fremstilling av fysiologisk aktive imidazoisokinolindioner
EP0074121A1 (de)	1983-03-16	2,3,4,5-Tetrahydro-1-benzoxepin-3,5-dion-Derivate und Verfahren zu deren Herstellung
NO154493B (no)	1986-06-23	Analogifremgangsmaate for fremstilling av nye, terapeutisk aktive 1-substituerte-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivater.
US3847927A (en)	1974-11-12	Sulfur-containing hydroxypyridones
NO166125B (no)	1991-02-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive aroyl-substituerte dihydro-1,4-tiaziner.
EP0072894A1 (en)	1983-03-02	Cyano-steroid compound and preparation thereof
NO122366B (fi)	1971-06-21
JPH01163175A (ja)	1989-06-27	フラン−２−オン誘導体
NO822445L (no)	1983-01-17	Fremgangsmaate ved fremstilling av 6-(3,6-dihydro-1(2h)-pyridyl)-pyrimidin-3-oksyder
DE10314139A1 (de)	2003-10-16	Verfahren zur Einführung einer 1,2-Doppelbindung bei 3-Oxo-4azasteroidverbindungen
NO136197B (fi)	1977-04-25
US4395550A (en)	1983-07-26	Tetrahydro-2(1H)-quinazolinones and cyclohexene nitriles