DE1948816C3 - Xanthenverbindungen und sie enthaltende Arzneimittel - Google Patents
Xanthenverbindungen und sie enthaltende ArzneimittelInfo
- Publication number
- DE1948816C3 DE1948816C3 DE19691948816 DE1948816A DE1948816C3 DE 1948816 C3 DE1948816 C3 DE 1948816C3 DE 19691948816 DE19691948816 DE 19691948816 DE 1948816 A DE1948816 A DE 1948816A DE 1948816 C3 DE1948816 C3 DE 1948816C3
- Authority
- DE
- Germany
- Prior art keywords
- xanthenyl
- semicarbazide
- compound
- formula
- solution
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 title claims 2
- 239000003814 drug Substances 0.000 title description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 230000002496 gastric effect Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KJRGZAXNSPNXHO-UHFFFAOYSA-N 1-amino-3-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(NC(=O)NN)C3=CC=CC=C3OC2=C1 KJRGZAXNSPNXHO-UHFFFAOYSA-N 0.000 description 4
- APASUFXYTUURIV-UHFFFAOYSA-N 9h-xanthene-9-carbonyl azide Chemical compound C1=CC=C2C(C(=O)N=[N+]=[N-])C3=CC=CC=C3OC2=C1 APASUFXYTUURIV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RIVZSCSPBGADLF-UHFFFAOYSA-N [O-]C(NC1C2=CC=CC=C2OC2=C1C=CC=C2)=[S+]C1=CC=CC=C1 Chemical compound [O-]C(NC1C2=CC=CC=C2OC2=C1C=CC=C2)=[S+]C1=CC=CC=C1 RIVZSCSPBGADLF-UHFFFAOYSA-N 0.000 description 3
- -1 amino-substituted xanthenes Chemical class 0.000 description 3
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- NQZWURVTDVKJKV-UHFFFAOYSA-N n-(9h-xanthen-9-yl)hydroxylamine Chemical compound C1=CC=C2C(NO)C3=CC=CC=C3OC2=C1 NQZWURVTDVKJKV-UHFFFAOYSA-N 0.000 description 3
- HJJXEMOBQKEHTL-UHFFFAOYSA-N n-methyl-n-(9h-xanthen-9-yl)carbamoyl chloride Chemical compound C1=CC=C2C(N(C)C(Cl)=O)C3=CC=CC=C3OC2=C1 HJJXEMOBQKEHTL-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZIKZLFAFMCEWOE-UHFFFAOYSA-N 1-(dimethylamino)-3-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(NC(=O)NN(C)C)C3=CC=CC=C3OC2=C1 ZIKZLFAFMCEWOE-UHFFFAOYSA-N 0.000 description 2
- NCSGYHBJAHTOGQ-UHFFFAOYSA-N 3-(dimethylamino)-1-hydroxy-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(O)C(=O)NN(C)C)C3=CC=CC=C3OC2=C1 NCSGYHBJAHTOGQ-UHFFFAOYSA-N 0.000 description 2
- DGMCHPPVZMVFFL-UHFFFAOYSA-N 3-amino-1-hydroxy-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(O)C(=O)NN)C3=CC=CC=C3OC2=C1 DGMCHPPVZMVFFL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HHPSFHIRFJQPSD-UHFFFAOYSA-N ClC(Cl)=[S+]C1=CC=CC=C1 Chemical compound ClC(Cl)=[S+]C1=CC=CC=C1 HHPSFHIRFJQPSD-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 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 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000003815 abdominal wall Anatomy 0.000 description 2
- 230000001262 anti-secretory effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- SVZFWZRCMLRFOM-UHFFFAOYSA-N dimethylaminourea Chemical compound CN(C)NC(N)=O SVZFWZRCMLRFOM-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical group N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- JNDLQQFKJPLTDR-UHFFFAOYSA-N n-methoxy-n-(9h-xanthen-9-yl)carbamoyl chloride Chemical compound C1=CC=C2C(N(OC)C(Cl)=O)C3=CC=CC=C3OC2=C1 JNDLQQFKJPLTDR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NZWDFSJJGJPRGG-UHFFFAOYSA-N s-phenyl n-hydroxy-n-(9h-xanthen-9-yl)carbamothioate Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1N(O)C(=O)SC1=CC=CC=C1 NZWDFSJJGJPRGG-UHFFFAOYSA-N 0.000 description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 150000003732 xanthenes Chemical class 0.000 description 2
- JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 description 2
- UOTJSUSNUMZRJG-UHFFFAOYSA-N 1-(propan-2-ylideneamino)-3-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(NC(=O)NN=C(C)C)C3=CC=CC=C3OC2=C1 UOTJSUSNUMZRJG-UHFFFAOYSA-N 0.000 description 1
- VLJMSSBTSBDICO-UHFFFAOYSA-N 3-(dimethylamino)-1-methyl-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(C)C(=O)NN(C)C)C3=CC=CC=C3OC2=C1 VLJMSSBTSBDICO-UHFFFAOYSA-N 0.000 description 1
- SGJBYPCBPRECAV-UHFFFAOYSA-N 3-amino-1-methoxy-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(OC)C(=O)NN)C3=CC=CC=C3OC2=C1 SGJBYPCBPRECAV-UHFFFAOYSA-N 0.000 description 1
- SQYMZWITYOZVDC-UHFFFAOYSA-N 3-amino-1-methyl-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(C)C(=O)NN)C3=CC=CC=C3OC2=C1 SQYMZWITYOZVDC-UHFFFAOYSA-N 0.000 description 1
- HWDPBCIRWHEZQW-UHFFFAOYSA-N 3-amino-1-propan-2-yloxy-1-(9h-xanthen-9-yl)urea Chemical compound C1=CC=C2C(N(OC(C)C)C(=O)NN)C3=CC=CC=C3OC2=C1 HWDPBCIRWHEZQW-UHFFFAOYSA-N 0.000 description 1
- RQMNNDHEGSDJRX-UHFFFAOYSA-N 9-chloro-9h-xanthene Chemical compound C1=CC=C2C(Cl)C3=CC=CC=C3OC2=C1 RQMNNDHEGSDJRX-UHFFFAOYSA-N 0.000 description 1
- VORWEIHRLWFDKD-UHFFFAOYSA-N 9-isocyanato-9h-xanthene Chemical compound C1=CC=C2C(N=C=O)C3=CC=CC=C3OC2=C1 VORWEIHRLWFDKD-UHFFFAOYSA-N 0.000 description 1
- OTTYHRLXKGOXLY-UHFFFAOYSA-N 9h-xanthen-9-amine Chemical compound C1=CC=C2C(N)C3=CC=CC=C3OC2=C1 OTTYHRLXKGOXLY-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 241000721662 Juniperus Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 description 1
- ZWVJQMNMBNYOPA-UHFFFAOYSA-N [dimethylaminocarbamoyl(9h-xanthen-9-yl)amino] acetate Chemical compound C1=CC=C2C(N(OC(C)=O)C(=O)NN(C)C)C3=CC=CC=C3OC2=C1 ZWVJQMNMBNYOPA-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- LCWAOCHOPBSGMU-UHFFFAOYSA-J aluminum;magnesium;sodium;hydrogen carbonate;oxygen(2-);silicon;trihydroxide Chemical compound [OH-].[OH-].[OH-].[O-2].[Na+].[Mg+2].[Al+3].[Si].OC([O-])=O LCWAOCHOPBSGMU-UHFFFAOYSA-J 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RMMQPTQDFCDKOD-UHFFFAOYSA-N ethyl 4-(9h-xanthen-9-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1C2=CC=CC=C2OC2=CC=CC=C21 RMMQPTQDFCDKOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NJDUDBTZFSEOLB-UHFFFAOYSA-N ethyl n-(9h-xanthen-9-ylcarbamoylamino)carbamate Chemical compound C1=CC=C2C(NC(=O)NNC(=O)OCC)C3=CC=CC=C3OC2=C1 NJDUDBTZFSEOLB-UHFFFAOYSA-N 0.000 description 1
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- XZWINYULFFVWBR-UHFFFAOYSA-N n-methoxy-9h-xanthen-9-amine Chemical compound C1=CC=C2C(NOC)C3=CC=CC=C3OC2=C1 XZWINYULFFVWBR-UHFFFAOYSA-N 0.000 description 1
- QSNPASFCZRWXNQ-UHFFFAOYSA-N n-methyl-9h-xanthen-9-amine Chemical compound C1=CC=C2C(NC)C3=CC=CC=C3OC2=C1 QSNPASFCZRWXNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
- C07D311/88—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4608568A GB1253521A (en) | 1968-09-27 | 1968-09-27 | Novel xanthen and thiaxanthen derivatives and the preparation thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1948816A1 DE1948816A1 (de) | 1970-04-02 |
| DE1948816B2 DE1948816B2 (de) | 1979-07-12 |
| DE1948816C3 true DE1948816C3 (de) | 1980-03-13 |
Family
ID=10439796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691948816 Expired DE1948816C3 (de) | 1968-09-27 | 1969-09-26 | Xanthenverbindungen und sie enthaltende Arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| JP (3) | JPS4811709B1 (enExample) |
| CA (1) | CA956943A (enExample) |
| CH (1) | CH520675A (enExample) |
| DE (1) | DE1948816C3 (enExample) |
| FR (1) | FR2019048B1 (enExample) |
| GB (1) | GB1253521A (enExample) |
| SE (1) | SE364958B (enExample) |
| SU (2) | SU404259A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52104305U (enExample) * | 1976-02-03 | 1977-08-08 | ||
| DE2918607A1 (de) * | 1979-05-09 | 1980-11-13 | Hoechst Ag | Verfahren zum klotzfaerben von bahnfoermigen textilien aus cellulosefasern |
| WO2015039334A1 (en) * | 2013-09-22 | 2015-03-26 | Merck Sharp & Dohme Corp. | TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF |
-
1968
- 1968-09-27 GB GB4608568A patent/GB1253521A/en not_active Expired
-
1969
- 1969-09-08 CA CA061,375A patent/CA956943A/en not_active Expired
- 1969-09-23 SU SU1608481A patent/SU404259A3/ru active
- 1969-09-23 SU SU1608480A patent/SU424353A3/ru active
- 1969-09-25 CH CH1450769A patent/CH520675A/fr not_active IP Right Cessation
- 1969-09-26 FR FR6932875A patent/FR2019048B1/fr not_active Expired
- 1969-09-26 DE DE19691948816 patent/DE1948816C3/de not_active Expired
- 1969-09-26 SE SE1331869A patent/SE364958B/xx unknown
-
1971
- 1971-12-27 JP JP38607271A patent/JPS4811709B1/ja active Pending
- 1971-12-27 JP JP38597271A patent/JPS4811708B1/ja active Pending
- 1971-12-27 JP JP38587271A patent/JPS4838711B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE364958B (enExample) | 1974-03-11 |
| FR2019048A1 (enExample) | 1970-06-26 |
| CH520675A (fr) | 1972-03-31 |
| JPS4811708B1 (enExample) | 1973-04-14 |
| JPS4838711B1 (enExample) | 1973-11-19 |
| FR2019048B1 (enExample) | 1973-01-12 |
| GB1253521A (en) | 1971-11-17 |
| CA956943A (en) | 1974-10-29 |
| SU404259A3 (enExample) | 1973-10-26 |
| SU424353A3 (enExample) | 1974-04-15 |
| JPS4811709B1 (enExample) | 1973-04-14 |
| DE1948816A1 (de) | 1970-04-02 |
| DE1948816B2 (de) | 1979-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |