NO834343L - Akridanon-derivater - Google Patents
Akridanon-derivaterInfo
- Publication number
- NO834343L NO834343L NO834343A NO834343A NO834343L NO 834343 L NO834343 L NO 834343L NO 834343 A NO834343 A NO 834343A NO 834343 A NO834343 A NO 834343A NO 834343 L NO834343 L NO 834343L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- acridanone
- lower alkyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- QMIGRZNKYXWKLB-UHFFFAOYSA-N 1-acridin-9-yl-2-(4,5-dihydro-1,3-thiazol-2-yl)hydrazine Chemical compound S1CCN=C1NNC1=C(C=CC=C2)C2=NC2=CC=CC=C12 QMIGRZNKYXWKLB-UHFFFAOYSA-N 0.000 claims description 4
- QKVFLBOWNGYJCX-UHFFFAOYSA-N 1-acridin-9-yl-2-(1,3-thiazol-2-yl)hydrazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1=NNC1=NC=CS1 QKVFLBOWNGYJCX-UHFFFAOYSA-N 0.000 claims description 3
- ZMQLEGRFAIMVIL-UHFFFAOYSA-N 2-acridin-9-yl-1-(4,5-dihydro-1,3-thiazol-2-yl)-1-methylhydrazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1=NN(C)C1=NCCS1 ZMQLEGRFAIMVIL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- DXNPCXIYJAHYPG-UHFFFAOYSA-N n-[(10-ethylacridin-9-ylidene)amino]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C12=CC=CC=C2N(CC)C2=CC=CC=C2C1=NNC1=NCCS1 DXNPCXIYJAHYPG-UHFFFAOYSA-N 0.000 claims description 3
- YSFYGAFRUMBSIZ-UHFFFAOYSA-N n-[(10-methylacridin-9-ylidene)amino]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C12=CC=CC=C2N(C)C2=CC=CC=C2C1=NNC1=NCCS1 YSFYGAFRUMBSIZ-UHFFFAOYSA-N 0.000 claims description 3
- RYLMKSWSHSUIQO-UHFFFAOYSA-N n-[[10-(2-methoxyethyl)acridin-9-ylidene]amino]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C12=CC=CC=C2N(CCOC)C2=CC=CC=C2C1=NNC1=NCCS1 RYLMKSWSHSUIQO-UHFFFAOYSA-N 0.000 claims description 3
- IQKUNVHIAKVMPQ-UHFFFAOYSA-N n-[(10-methylacridin-9-ylidene)amino]-1,3-thiazol-2-amine Chemical compound C12=CC=CC=C2N(C)C2=CC=CC=C2C1=NNC1=NC=CS1 IQKUNVHIAKVMPQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000001843 schistosomicidal effect Effects 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- XYTRVFMNMJPWQV-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-ylhydrazine;hydrobromide Chemical compound Br.NNC1=NCCS1 XYTRVFMNMJPWQV-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- -1 2,2-dimethoxyethyl Chemical group 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XUVKSPPGPPFPQN-UHFFFAOYSA-N 10-Methyl-9(10H)-acridone Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C(=O)C2=C1 XUVKSPPGPPFPQN-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 201000004409 schistosomiasis Diseases 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HHYXHHPLUJAGMS-UHFFFAOYSA-N (acridin-9-ylamino)thiourea Chemical compound C1=CC=C2C(NNC(=S)N)=C(C=CC=C3)C3=NC2=C1 HHYXHHPLUJAGMS-UHFFFAOYSA-N 0.000 description 2
- PMDKUKBRNUZWMZ-UHFFFAOYSA-N 10-methyl-1-nitroacridin-9-one Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C(=O)C2=C1[N+]([O-])=O PMDKUKBRNUZWMZ-UHFFFAOYSA-N 0.000 description 2
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 2
- JOUFIQVFVDNYRT-UHFFFAOYSA-N 9-chloro-1-nitroacridine Chemical compound C1=CC=C2C(Cl)=C3C([N+](=O)[O-])=CC=CC3=NC2=C1 JOUFIQVFVDNYRT-UHFFFAOYSA-N 0.000 description 2
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HDYXWWNRTPRCKV-UHFFFAOYSA-N [(10-methylacridin-9-ylidene)amino]thiourea Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C(=NNC(N)=S)C2=C1 HDYXWWNRTPRCKV-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BBNVVIDNGCOCTC-UHFFFAOYSA-M 1,9-dichloro-10-methylacridin-10-ium;dichlorophosphinate Chemical compound [O-]P(Cl)(Cl)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=C(Cl)C2=C1Cl BBNVVIDNGCOCTC-UHFFFAOYSA-M 0.000 description 1
- KGZKZBGDTLVWPR-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-1-methylhydrazine;hydrochloride Chemical compound Cl.CN(N)C1=NCCS1 KGZKZBGDTLVWPR-UHFFFAOYSA-N 0.000 description 1
- KBFAJEYUSAGXTM-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-2-(1-nitroacridin-9-yl)hydrazine Chemical compound C=12C([N+](=O)[O-])=CC=CC2=NC2=CC=CC=C2C=1NNC1=NCCS1 KBFAJEYUSAGXTM-UHFFFAOYSA-N 0.000 description 1
- SZXUETYUKVVEDJ-UHFFFAOYSA-N 1-methyl-1-(1,3-thiazol-2-yl)hydrazine;hydrochloride Chemical compound Cl.CN(N)C1=NC=CS1 SZXUETYUKVVEDJ-UHFFFAOYSA-N 0.000 description 1
- XNOZVNKYKUNSDT-UHFFFAOYSA-N 1-methyl-2-(1-nitroacridin-9-yl)-1-(1,3-thiazol-2-yl)hydrazine;hydrochloride Chemical compound Cl.C12=CC=CC=C2NC2=CC=CC([N+]([O-])=O)=C2C1=NN(C)C1=NC=CS1 XNOZVNKYKUNSDT-UHFFFAOYSA-N 0.000 description 1
- FJNZOTVFXOADDQ-UHFFFAOYSA-N 1-nitro-10h-acridin-9-one Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] FJNZOTVFXOADDQ-UHFFFAOYSA-N 0.000 description 1
- SUBHXOOWWUMPEW-UHFFFAOYSA-N 10-(2-methoxyethyl)acridin-9-one Chemical compound C1=CC=C2N(CCOC)C3=CC=CC=C3C(=O)C2=C1 SUBHXOOWWUMPEW-UHFFFAOYSA-N 0.000 description 1
- QFDDZIRGHKFRMR-UHFFFAOYSA-N 10-butylacridin-9-one Chemical compound C1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 QFDDZIRGHKFRMR-UHFFFAOYSA-N 0.000 description 1
- XLUFPCKIXLAEED-UHFFFAOYSA-N 10-ethylacridin-9-one Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C(=O)C2=C1 XLUFPCKIXLAEED-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- JXVDRESVDFMFPL-UHFFFAOYSA-M 9-chloro-10-ethylacridin-10-ium;dichlorophosphinate Chemical compound [O-]P(Cl)(Cl)=O.C1=CC=C2[N+](CC)=C(C=CC=C3)C3=C(Cl)C2=C1 JXVDRESVDFMFPL-UHFFFAOYSA-M 0.000 description 1
- FZJLXPKRCKYIOH-UHFFFAOYSA-M 9-chloro-10-methylacridin-10-ium;dichlorophosphinate Chemical compound [O-]P(Cl)(Cl)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=C(Cl)C2=C1 FZJLXPKRCKYIOH-UHFFFAOYSA-M 0.000 description 1
- ZHBWKWDAMIJZPW-UHFFFAOYSA-N 9-methoxyacridine Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=NC2=C1 ZHBWKWDAMIJZPW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- HDMSFVIXAQOAAD-UHFFFAOYSA-N [N].C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 Chemical group [N].C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 HDMSFVIXAQOAAD-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 210000001758 mesenteric vein Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DVCQNKVXQHSSCR-UHFFFAOYSA-N n-[(1-chloro-10-methylacridin-9-ylidene)amino]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C12=C(Cl)C=CC=C2N(C)C2=CC=CC=C2C1=NNC1=NCCS1 DVCQNKVXQHSSCR-UHFFFAOYSA-N 0.000 description 1
- JVODNOVXDYEFHA-UHFFFAOYSA-N n-[(10-butylacridin-9-ylidene)amino]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C12=CC=CC=C2N(CCCC)C2=CC=CC=C2C1=NNC1=NCCS1 JVODNOVXDYEFHA-UHFFFAOYSA-N 0.000 description 1
- GJYGBUVLCORUGA-UHFFFAOYSA-N n-[(10-methylacridin-9-ylidene)amino]-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C2=CC=CC=C2C1=NNC1=NC=CS1 GJYGBUVLCORUGA-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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine 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 ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine 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 ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH689582 | 1982-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834343L true NO834343L (no) | 1984-05-28 |
Family
ID=4316746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834343A NO834343L (no) | 1982-11-26 | 1983-11-25 | Akridanon-derivater |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4544659A (fr) |
| EP (1) | EP0111205B1 (fr) |
| JP (1) | JPS59106485A (fr) |
| KR (1) | KR840006652A (fr) |
| AT (1) | ATE26275T1 (fr) |
| AU (1) | AU564739B2 (fr) |
| BR (1) | BR8306505A (fr) |
| CS (1) | CS235990B2 (fr) |
| CU (1) | CU21558A3 (fr) |
| DE (1) | DE3370627D1 (fr) |
| DK (1) | DK542183D0 (fr) |
| EG (1) | EG16489A (fr) |
| ES (2) | ES8506012A1 (fr) |
| FI (1) | FI834130A (fr) |
| GR (1) | GR79079B (fr) |
| HU (1) | HU191498B (fr) |
| IE (1) | IE56310B1 (fr) |
| IL (1) | IL70272A (fr) |
| MC (1) | MC1555A1 (fr) |
| NO (1) | NO834343L (fr) |
| NZ (1) | NZ206316A (fr) |
| PH (1) | PH21438A (fr) |
| PT (1) | PT77728B (fr) |
| ZA (1) | ZA838641B (fr) |
| ZW (1) | ZW22983A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4711889A (en) * | 1983-11-15 | 1987-12-08 | Hoffman-La Roche Inc. | Schistosomicidal acridanone hydrazones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH96608A (de) * | 1920-10-28 | 1922-11-01 | Hoechst Ag | Verfahren zur Darstellung eines Acridinderivates. |
| CH94982A (de) * | 1921-09-12 | 1922-10-02 | Hoechst Ag | Verfahren zur Darstellung eines Acridinderivates. |
| GB1068595A (en) * | 1964-06-08 | 1967-05-10 | Gevaert Photo Prod Nv | Colour photographic process |
| DE1811409A1 (de) * | 1968-11-28 | 1970-06-18 | Bayer Ag | Mittel zur Bekaempfung von Insekten,Milben,Hasenartigen und Nagetieren |
| DE2235177A1 (de) * | 1972-07-18 | 1974-02-07 | Bayer Ag | Verfahren zur herstellung von lactamhydrazonen aromatischer systeme |
-
1983
- 1983-02-26 CU CU8335978A patent/CU21558A3/es unknown
- 1983-10-26 ZW ZW229/83A patent/ZW22983A1/xx unknown
- 1983-11-01 EG EG678/83A patent/EG16489A/xx active
- 1983-11-10 FI FI834130A patent/FI834130A/fi not_active Application Discontinuation
- 1983-11-15 US US06/551,816 patent/US4544659A/en not_active Expired - Fee Related
- 1983-11-16 CS CS838489A patent/CS235990B2/cs unknown
- 1983-11-18 IL IL70272A patent/IL70272A/xx unknown
- 1983-11-18 NZ NZ206316A patent/NZ206316A/en unknown
- 1983-11-18 ZA ZA838641A patent/ZA838641B/xx unknown
- 1983-11-21 AU AU21553/83A patent/AU564739B2/en not_active Ceased
- 1983-11-22 EP EP83111672A patent/EP0111205B1/fr not_active Expired
- 1983-11-22 AT AT83111672T patent/ATE26275T1/de not_active IP Right Cessation
- 1983-11-22 DE DE8383111672T patent/DE3370627D1/de not_active Expired
- 1983-11-23 HU HU834023A patent/HU191498B/hu unknown
- 1983-11-24 GR GR73056A patent/GR79079B/el unknown
- 1983-11-25 KR KR1019830005589A patent/KR840006652A/ko not_active Application Discontinuation
- 1983-11-25 PH PH29889A patent/PH21438A/en unknown
- 1983-11-25 NO NO834343A patent/NO834343L/no unknown
- 1983-11-25 DK DK5421/83A patent/DK542183D0/da not_active Application Discontinuation
- 1983-11-25 BR BR8306505A patent/BR8306505A/pt unknown
- 1983-11-25 ES ES527550A patent/ES8506012A1/es not_active Expired
- 1983-11-25 MC MC831671A patent/MC1555A1/fr unknown
- 1983-11-25 IE IE2769/83A patent/IE56310B1/xx unknown
- 1983-11-25 JP JP58220894A patent/JPS59106485A/ja active Pending
- 1983-11-25 PT PT77728A patent/PT77728B/pt unknown
-
1984
- 1984-07-05 ES ES534033A patent/ES8506014A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU2155383A (en) | 1984-05-31 |
| ES534033A0 (es) | 1985-06-16 |
| FI834130A0 (fi) | 1983-11-10 |
| PT77728A (en) | 1983-12-01 |
| IE832769L (en) | 1984-05-26 |
| IL70272A0 (en) | 1984-02-29 |
| ES527550A0 (es) | 1985-06-16 |
| ZW22983A1 (en) | 1985-05-22 |
| IL70272A (en) | 1986-11-30 |
| GR79079B (fr) | 1984-10-02 |
| KR840006652A (ko) | 1984-12-01 |
| IE56310B1 (en) | 1991-06-19 |
| CS235990B2 (en) | 1985-05-15 |
| ES8506014A1 (es) | 1985-06-16 |
| EG16489A (en) | 1988-01-31 |
| MC1555A1 (fr) | 1984-08-31 |
| DK542183D0 (da) | 1983-11-25 |
| ATE26275T1 (de) | 1987-04-15 |
| ZA838641B (en) | 1984-07-25 |
| BR8306505A (pt) | 1984-06-26 |
| FI834130A (fi) | 1984-05-27 |
| ES8506012A1 (es) | 1985-06-16 |
| HU191498B (en) | 1987-02-27 |
| US4544659A (en) | 1985-10-01 |
| EP0111205A1 (fr) | 1984-06-20 |
| DE3370627D1 (de) | 1987-05-07 |
| PH21438A (en) | 1987-10-20 |
| NZ206316A (en) | 1987-06-30 |
| AU564739B2 (en) | 1987-08-27 |
| PT77728B (en) | 1986-06-18 |
| CU21558A3 (en) | 1987-07-02 |
| JPS59106485A (ja) | 1984-06-20 |
| EP0111205B1 (fr) | 1987-04-01 |
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