NO874950L - Isokinolin-derivater. - Google Patents

Isokinolin-derivater.

Info

Publication number: NO874950L
Authority: NO; Norway
Prior art keywords: group; compound; general formula; hydrogen atom; formula
Prior art date: 1986-11-27

Application number

NO874950A

Other languages

English (en)

Norwegian (no)

Other versions

NO874950D0 (no

Inventor

Gordon Hanley Phillipps

Michael George Lester

Original Assignee

Glaxo Group Ltd

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.)

1986-11-27

Filing date

1987-11-26

Publication date

1988-05-30

1986-11-27 Priority claimed from GB868628352A external-priority patent/GB8628352D0/en

1986-11-27 Priority claimed from GB868628349A external-priority patent/GB8628349D0/en

1986-11-27 Priority claimed from GB868628351A external-priority patent/GB8628351D0/en

1987-11-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1987-11-26 Publication of NO874950D0 publication Critical patent/NO874950D0/no

1988-05-30 Publication of NO874950L publication Critical patent/NO874950L/no

Links

125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 130
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 33
238000000034 method Methods 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
-1 hydroxyethyl group Chemical group 0.000 claims description 17
206010028980 Neoplasm Diseases 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
150000007857 hydrazones Chemical class 0.000 claims description 4
JAGLTDLJKOOIND-UHFFFAOYSA-N n,n-diethylbut-2-en-1-amine Chemical compound CCN(CC)CC=CC JAGLTDLJKOOIND-UHFFFAOYSA-N 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
BFRVNBMAWXNICS-UHFFFAOYSA-N mitoquidone Chemical compound C1=CC=C2C(=O)C3=CN(CC=4C(=CC=CC=4)C4)C4=C3C(=O)C2=C1 BFRVNBMAWXNICS-UHFFFAOYSA-N 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
239000007858 starting material Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
239000000203 mixture Substances 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000000543 intermediate Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000007787 solid Substances 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000243 solution Substances 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
230000010933 acylation Effects 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000012267 brine Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000001093 anti-cancer Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000005947 deacylation reaction Methods 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
239000006196 drop Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000001119 stannous chloride Substances 0.000 description 3
235000011150 stannous chloride Nutrition 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
RCVYBCBPKFXHGD-UHFFFAOYSA-N 16-[2-(diethylamino)ethylamino]-3-methyl-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1,4,6,8,12,15(20),16,18-octaene-14,21-dione Chemical compound C1=CC=C2C(C)C3=C4C(=O)C(C=CC=C5NCCN(CC)CC)=C5C(=O)C4=CN3CC2=C1 RCVYBCBPKFXHGD-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VNRJGEMERJZKLQ-UHFFFAOYSA-N 2-piperazin-1-ylacetamide Chemical compound NC(=O)CN1CCNCC1 VNRJGEMERJZKLQ-UHFFFAOYSA-N 0.000 description 2
XLEOCTUCGZANAC-UHFFFAOYSA-N 4-(diethylamino)butan-2-one Chemical compound CCN(CC)CCC(C)=O XLEOCTUCGZANAC-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
SHGLSLNZCXDAAI-UHFFFAOYSA-N N'-[1-(dimethylamino)ethyl]-N'-(14,21-dioxo-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1,4,6,8,12,15(20),16,18-octaen-19-yl)acetohydrazide Chemical compound C1=CC=C2CC3=C(C(=O)C=4C(N(NC(C)=O)C(N(C)C)C)=CC=CC=4C4=O)C4=CN3CC2=C1 SHGLSLNZCXDAAI-UHFFFAOYSA-N 0.000 description 2
WBFMPIONHHKNIY-UHFFFAOYSA-N N'-[1-(dimethylamino)ethyl]-N'-(3-methyl-14,21-dioxo-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1,4,6,8,12,15(20),16,18-octaen-19-yl)acetohydrazide Chemical compound C1=CC=C2C(C)C3=C(C(=O)C=4C(N(NC(C)=O)C(N(C)C)C)=CC=CC=4C4=O)C4=CN3CC2=C1 WBFMPIONHHKNIY-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical group ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
239000000443 aerosol Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000002111 antiemetic agent Substances 0.000 description 2
229940125683 antiemetic agent Drugs 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000008365 aqueous carrier Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000020176 deacylation Effects 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
239000003349 gelling agent Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000003840 hydrochlorides 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
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000003018 immunosuppressive agent Substances 0.000 description 2
229940125721 immunosuppressive agent Drugs 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
JVDZAWWUMLHNGT-UHFFFAOYSA-N n,n-diethylprop-1-en-1-amine Chemical compound CCN(CC)C=CC JVDZAWWUMLHNGT-UHFFFAOYSA-N 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
230000007306 turnover Effects 0.000 description 2
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
IFCWYTXVFSHTNL-UHFFFAOYSA-N 2,2,2-trifluoro-N-(3-methyl-14,21-dioxo-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1,4,6,8,12,15(20),16,18-octaen-16-yl)acetamide Chemical compound C1=CC=C2C(=O)C3=C4C(C)C5=CC=CC=C5CN4C=C3C(=O)C2=C1NC(=O)C(F)(F)F IFCWYTXVFSHTNL-UHFFFAOYSA-N 0.000 description 1
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
OQZGYMRYZAKXAF-UHFFFAOYSA-N 2-(4-methylcyclohexyl)acetic acid Chemical compound CC1CCC(CC(O)=O)CC1 OQZGYMRYZAKXAF-UHFFFAOYSA-N 0.000 description 1
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 description 1
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
MHRNGQVWZRPUJI-UHFFFAOYSA-N 2-formyl-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN(C=O)C(C(=O)O)CC2=C1 MHRNGQVWZRPUJI-UHFFFAOYSA-N 0.000 description 1
CISZOKXGLUCUKZ-UHFFFAOYSA-N 2-formyl-4-methyl-3,4,4a,5-tetrahydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1C=CC=C2CN(C=O)C(C(O)=O)C(C)C21 CISZOKXGLUCUKZ-UHFFFAOYSA-N 0.000 description 1
FLWHAZBUPDFRMQ-UHFFFAOYSA-N 5,8,13,14-tetrahydro-14-methyl-9-nitrobenz[5,6]isoindolo[2,1-b]-isoquinoline-8,13-dione Chemical compound C=1N2CC3=CC=CC=C3C(C)C2=C(C2=O)C=1C(=O)C1=C2C=CC=C1[N+]([O-])=O FLWHAZBUPDFRMQ-UHFFFAOYSA-N 0.000 description 1
ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
VSBOSAGJYNRBJN-UHFFFAOYSA-N 5-nitronaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2[N+](=O)[O-] VSBOSAGJYNRBJN-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001480079 Corymbia calophylla Species 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
235000006552 Liquidambar styraciflua Nutrition 0.000 description 1
208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000003064 anti-oxidating effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000002051 biphasic effect Effects 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
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000002502 liposome Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000005374 membrane filtration Methods 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
239000004005 microsphere Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
229940096978 oral tablet Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 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
230000003595 spectral effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 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
230000008719 thickening Effects 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO874950A 1986-11-27 1987-11-26 Isokinolin-derivater. NO874950L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB868628352A GB8628352D0 (en)	1986-11-27	1986-11-27	Chemical compounds
GB868628349A GB8628349D0 (en)	1986-11-27	1986-11-27	Chemical compounds
GB868628351A GB8628351D0 (en)	1986-11-27	1986-11-27	Chemical compounds

Publications (2)

Publication Number	Publication Date
NO874950D0 NO874950D0 (no)	1987-11-26
NO874950L true NO874950L (no)	1988-05-30

Family

ID=27263219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO874950A NO874950L (no)	1986-11-27	1987-11-26	Isokinolin-derivater.

Country Status (9)

Country	Link
US (1)	US4959371A (da)
EP (1)	EP0274842A1 (da)
KR (1)	KR880006236A (da)
AU (1)	AU8187587A (da)
DK (1)	DK616087A (da)
FI (1)	FI875219A7 (da)
IL (1)	IL84609A0 (da)
NO (1)	NO874950L (da)
NZ (1)	NZ222702A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8800312D0 (en) *	1988-01-07	1988-02-10	Glaxo Group Ltd	Process

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1087222A (en) *	1963-03-16	1967-10-18	Geigy Uk Ltd	12-nitronaphthindolizinediones and processes for their manufacture
US4029659A (en) *	1971-03-29	1977-06-14	Omnium Chimique Societe Anonyme	N-disubstituted aminoethyl esters of 11-methoxy-raubasinic acid
US3894029A (en) *	1971-08-26	1975-07-08	Basf Ag	Production of camptothecin and camptothecin-like compounds
GB1459137A (en) *	1973-05-30	1976-12-22	Sandoz Ltd	Naphthoquinone derivatives
US4033966A (en) *	1975-06-24	1977-07-05	Kanebo, Ltd.	Novel berbine derivatives
US4087426A (en) *	1976-08-16	1978-05-02	Research Corporation	Oxybisberberine and a process for its production
FR2387229A1 (fr) *	1977-04-13	1978-11-10	Anvar	Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant
FR2436786A1 (fr) *	1978-09-21	1980-04-18	Anvar	Nouveaux derives des pyrido (4,3-b) carbazoles (ellipticines), substitues en position 1 par une chaine polyaminee, leur obtention et leur application a titre de medicaments
US4399282A (en) *	1979-07-10	1983-08-16	Kabushiki Kaisha Yakult Honsha	Camptothecin derivatives
DK158666C (da) *	1982-11-04	1990-11-19	Glaxo Group Ltd	Analogifremgangsmaade til fremstilling af 5,14-dihydrobenz-oe5,6aa-isoindolooe2,1-baa-isoquinolin-8,13-dion
DK160991C (da) *	1984-05-03	1991-11-11	Glaxo Group Ltd	5,14-dihydrobenzoe5,6aaisoindolooe2,1-baaisoquinolin-8,13-dionderivater, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende en saadan forbindelse
GB8513460D0 (en) *	1985-05-29	1985-07-03	Glaxo Group Ltd	Chemical compounds

1987
- 1987-11-24 DK DK616087A patent/DK616087A/da not_active Application Discontinuation
- 1987-11-25 US US07/125,173 patent/US4959371A/en not_active Expired - Fee Related
- 1987-11-26 FI FI875219A patent/FI875219A7/fi not_active Application Discontinuation
- 1987-11-26 EP EP87310450A patent/EP0274842A1/en not_active Withdrawn
- 1987-11-26 NZ NZ222702A patent/NZ222702A/xx unknown
- 1987-11-26 IL IL84609A patent/IL84609A0/xx unknown
- 1987-11-26 KR KR870013327A patent/KR880006236A/ko not_active Withdrawn
- 1987-11-26 NO NO874950A patent/NO874950L/no unknown
- 1987-11-27 AU AU81875/87A patent/AU8187587A/en not_active Abandoned

Also Published As

Publication number	Publication date
EP0274842A1 (en)	1988-07-20
AU8187587A (en)	1988-06-02
US4959371A (en)	1990-09-25
NO874950D0 (no)	1987-11-26
FI875219A0 (fi)	1987-11-26
FI875219A7 (fi)	1988-05-28
NZ222702A (en)	1990-05-28
DK616087A (da)	1988-05-28
DK616087D0 (da)	1987-11-24
IL84609A0 (en)	1988-04-29
KR880006236A (ko)	1988-07-22

Publication	Publication Date	Title
US4382892A (en)	1983-05-10	Benzoxazine derivatives
EP0187322B1 (en)	1990-03-14	Carbostyril compounds, compositions containing same and processes for preparing same
EP0009425A1 (en)	1980-04-02	Novel naphtyridine derivatives and pharmaceutical compositions containing them
NO170929B (no)	1992-09-21	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotiazolforbindelser
NO302073B1 (no)	1998-01-19	Vannopplöselige camptothecin-derivater
FR2492382A1 (fr)	1982-04-23	Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique
US20250382309A1 (en)	2025-12-18	Methods and materials for increasing transcription factor eb polypeptide levels
TW201904974A (zh)	2019-02-01	雜芳基并嘧啶酮類衍生物、其製備方法及其在醫藥上用途
Sahua et al.	2014	Synthesis of some novel heterocyclic 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazole derivatives as possible antimicrobial agents
US9598434B2 (en)	2017-03-21	Benzazepine compound
IL107330A (en)	1998-04-05	SUBSTITUTED (PYRIDINYLAMINO)- BENZISOXAZOLES AND-BENZO £b\| THIOPHENES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US4233333A (en)	1980-11-11	4,5-Dimethyl-thieno[3,2-d]isothiazolo-3(2H)-one-1,1-dioxides, compositions, and methods of use as a sweetener
CN103664996B (zh)	2017-10-03	吲哚衍生物及其制备方法
KR20010042904A (ko)	2001-05-25	광학 활성 테트라하이드로벤즈인돌 유도체
IE831622L (en)	1984-01-23	ANTHRA(1,9- cd) PYRAZOLE-6-ONES AND INTERMEDIATES FOR THEIR¹PREPARATION
US3948913A (en)	1976-04-06	New 5-nitrofuryl derivatives
US4044130A (en)	1977-08-23	Compositions for the control of microorganisms
HU204056B (en)	1991-11-28	Process for producing new azetidine derivatives
NO162907B (no)	1989-11-27	Analogifremgangsmaate for fremstilling av terapeutisk aktive bis-(piperazinyl-resp. homopiperazinyl)-alkaner.
BG63206B1 (bg)	2001-06-29	Кондензирани тиазолови производни с афинитет към 5-нт рецептори
WO1993010119A1 (en)	1993-05-27	Heterocyclic compounds
US20250144102A1 (en)	2025-05-08	1 h-pyrazolo[4,3-d]pyrimidine derivatives as staphylococcus aureus inhibitors
JPH02191257A (ja)	1990-07-27	ベンゾヘテロ環化合物
PT97570A (pt)	1992-01-31	Processo para a preparacao de derivados de benzotienopiridina
Sayed et al.	2010	Antimicrobial activity of some synthesized glucopyranosyl-pyrimidine carbonitrile and fused pyrimidine systems