NO762625L - - Google Patents
Info
- Publication number
- NO762625L NO762625L NO762625A NO762625A NO762625L NO 762625 L NO762625 L NO 762625L NO 762625 A NO762625 A NO 762625A NO 762625 A NO762625 A NO 762625A NO 762625 L NO762625 L NO 762625L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- dichloro
- general formula
- methyl
- sulfamoylphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 94
- 238000000034 method Methods 0.000 claims description 40
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003585 thioureas Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000000054 salidiuretic effect Effects 0.000 claims description 5
- 150000003548 thiazolidines Chemical class 0.000 claims description 5
- VJJNINFTAGMAIH-UHFFFAOYSA-N 2,4-dichloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonamide Chemical compound CN1C(=NC)SCC1(O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl VJJNINFTAGMAIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- WGLTYNFLVMWBTI-UHFFFAOYSA-N 2,3-dichloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 WGLTYNFLVMWBTI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- BLZRASMYVBJRPO-UHFFFAOYSA-N 2,3-dichloro-5-(3-ethyl-2-ethylimino-4-hydroxy-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrochloride Chemical compound Cl.CCN1C(=NCC)SCC1(O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 BLZRASMYVBJRPO-UHFFFAOYSA-N 0.000 claims 1
- XCYAKIPSQRIUGI-UHFFFAOYSA-N 2,3-dichloro-5-(4-hydroxy-3-propan-2-yl-2-propan-2-ylimino-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrochloride Chemical compound Cl.CC(C)N1C(=NC(C)C)SCC1(O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 XCYAKIPSQRIUGI-UHFFFAOYSA-N 0.000 claims 1
- MTJNXKKWJXHTHX-UHFFFAOYSA-N 2,4-dichloro-5-(3-ethyl-2-ethylimino-4-hydroxy-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CCN1C(=NCC)SCC1(O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl MTJNXKKWJXHTHX-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 150000003549 thiazolines Chemical class 0.000 claims 1
- 230000008018 melting Effects 0.000 description 64
- 238000002844 melting Methods 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- 238000000354 decomposition reaction Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 21
- -1 for example Substances 0.000 description 21
- 235000011054 acetic acid Nutrition 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- RRHSDGPLLWXDMS-UHFFFAOYSA-N 5-(2-bromoacetyl)-2,4-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CBr)=C(Cl)C=C1Cl RRHSDGPLLWXDMS-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000001376 precipitating effect Effects 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- WRTYVFZFXYTXSG-UHFFFAOYSA-N 5-(2-bromoacetyl)-2,3-dimethylbenzenesulfonamide Chemical compound CC1=CC(C(=O)CBr)=CC(S(N)(=O)=O)=C1C WRTYVFZFXYTXSG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 description 3
- KNKYFNVAKXGKCQ-UHFFFAOYSA-N 2,3-dichloro-5-(2-chloroacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CCl)=CC(Cl)=C1Cl KNKYFNVAKXGKCQ-UHFFFAOYSA-N 0.000 description 3
- NGXCLFHJFMVHTH-UHFFFAOYSA-N 2,3-dichloro-5-(2-diazoacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)C=[N+]=[N-])=CC(Cl)=C1Cl NGXCLFHJFMVHTH-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- DZZWKUMHMSNBSG-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)thiourea Chemical compound C=CCNC(=S)NCC=C DZZWKUMHMSNBSG-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- FHXLAZZNBCTRBG-UHFFFAOYSA-N 1-ethyl-3-(2-methylpropyl)thiourea Chemical compound CCNC(=S)NCC(C)C FHXLAZZNBCTRBG-UHFFFAOYSA-N 0.000 description 2
- QAXLTNJBFTYLBZ-UHFFFAOYSA-N 2,4-dichloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl QAXLTNJBFTYLBZ-UHFFFAOYSA-N 0.000 description 2
- IALYEKVUWNTGAT-UHFFFAOYSA-N 2,4-dichloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonyl chloride;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(S(Cl)(=O)=O)=C(Cl)C=C1Cl IALYEKVUWNTGAT-UHFFFAOYSA-N 0.000 description 2
- OTVGARFFAAFRAC-UHFFFAOYSA-N 2-bromo-1,4-dioxane Chemical compound BrC1COCCO1 OTVGARFFAAFRAC-UHFFFAOYSA-N 0.000 description 2
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 2
- HNRPDSZSNRJMKX-UHFFFAOYSA-N 3,4-dichloro-5-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC(Cl)=C1Cl HNRPDSZSNRJMKX-UHFFFAOYSA-N 0.000 description 2
- XZEQULLPTDRCGC-UHFFFAOYSA-N 3,4-dimethyl-5-sulfamoylbenzoyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC(S(N)(=O)=O)=C1C XZEQULLPTDRCGC-UHFFFAOYSA-N 0.000 description 2
- OSDSKDBDQWYZCO-UHFFFAOYSA-N 3-bromo-4-chloro-5-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC(Br)=C1Cl OSDSKDBDQWYZCO-UHFFFAOYSA-N 0.000 description 2
- KXMDTAVLBDHXGY-UHFFFAOYSA-N 3-chloro-4-methyl-5-sulfamoylbenzoyl chloride Chemical compound CC1=C(Cl)C=C(C(Cl)=O)C=C1S(N)(=O)=O KXMDTAVLBDHXGY-UHFFFAOYSA-N 0.000 description 2
- APZHPSUSQSWUPD-UHFFFAOYSA-N 3-chloro-5-(2-diazoacetyl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=C(C(=O)C=[N+]=[N-])C=C1S(N)(=O)=O APZHPSUSQSWUPD-UHFFFAOYSA-N 0.000 description 2
- WZUUMRFCTIZHPD-UHFFFAOYSA-N 3-chloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)-2-methylbenzenesulfonamide;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(Cl)=C(C)C(S(N)(=O)=O)=C1 WZUUMRFCTIZHPD-UHFFFAOYSA-N 0.000 description 2
- TVRGPNZSOOPBHK-UHFFFAOYSA-N 5-(2-bromoacetyl)-2,4-dichloro-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(C(=O)CBr)=C(Cl)C=C1Cl TVRGPNZSOOPBHK-UHFFFAOYSA-N 0.000 description 2
- ORWFUSLGHUGXMO-UHFFFAOYSA-N 5-(2-bromoacetyl)-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=C(C(=O)CBr)C=C1S(N)(=O)=O ORWFUSLGHUGXMO-UHFFFAOYSA-N 0.000 description 2
- KOMSWUBFNSXWRS-UHFFFAOYSA-N 5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)-2,3-dimethylbenzenesulfonamide;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(C)=C(C)C(S(N)(=O)=O)=C1 KOMSWUBFNSXWRS-UHFFFAOYSA-N 0.000 description 2
- SACDLDIMGQGNIK-UHFFFAOYSA-N 5-acetyl-2,4-dichlorobenzenesulfonamide Chemical compound CC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl SACDLDIMGQGNIK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 238000007710 freezing Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
- 229960003602 guanethidine Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- DVDPOHJDKLTTMQ-UHFFFAOYSA-N n-benzyl-2,4-dichloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC(S(=O)(=O)NCC=2C=CC=CC=2)=C(Cl)C=C1Cl DVDPOHJDKLTTMQ-UHFFFAOYSA-N 0.000 description 1
- RSCBEUUQVDGGFE-UHFFFAOYSA-N n-benzyl-5-(2-bromoacetyl)-2,4-dichlorobenzenesulfonamide Chemical compound C1=C(C(=O)CBr)C(Cl)=CC(Cl)=C1S(=O)(=O)NCC1=CC=CC=C1 RSCBEUUQVDGGFE-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- LPRGKCJPVZAUIJ-UHFFFAOYSA-N oxetane-2-sulfonic acid Chemical compound OS(=O)(=O)C1CCO1 LPRGKCJPVZAUIJ-UHFFFAOYSA-N 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- NNBYMSMZMXBZJS-UHFFFAOYSA-N s-[2-(2,4-dichloro-5-sulfamoylphenyl)-2-oxoethyl] ethanethioate Chemical compound CC(=O)SCC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl NNBYMSMZMXBZJS-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 230000008646 thermal stress Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752533821 DE2533821A1 (de) | 1975-07-29 | 1975-07-29 | Thiazolidinderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762625L true NO762625L (nl) | 1977-02-01 |
Family
ID=5952702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762625A NO762625L (nl) | 1975-07-29 | 1976-07-28 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4061647A (nl) |
| JP (1) | JPS5217468A (nl) |
| AT (1) | AT353267B (nl) |
| AU (1) | AU498052B2 (nl) |
| BE (1) | BE844666A (nl) |
| CA (1) | CA1077492A (nl) |
| DE (1) | DE2533821A1 (nl) |
| DK (1) | DK340476A (nl) |
| ES (3) | ES450070A1 (nl) |
| FI (1) | FI762140A (nl) |
| FR (1) | FR2319345A1 (nl) |
| GB (1) | GB1522107A (nl) |
| IL (1) | IL50146A (nl) |
| LU (1) | LU75475A1 (nl) |
| NL (1) | NL7608206A (nl) |
| NO (1) | NO762625L (nl) |
| SE (1) | SE7608545L (nl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| DE2737195A1 (de) * | 1977-08-18 | 1979-03-01 | Hoechst Ag | Benzolsulfonamidderivate und verfahren zu ihrer herstellung |
| DE2926771A1 (de) | 1979-07-03 | 1981-01-15 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| DE3049460A1 (de) * | 1980-12-30 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | "thiazolinderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| US4624720A (en) * | 1983-01-06 | 1986-11-25 | Raychem Ltd | Dimensionally heat-recoverable article |
| GB8300220D0 (en) * | 1983-01-06 | 1983-02-09 | Raychem Ltd | Arrangement for enclosing substrates |
| JPS59227870A (ja) * | 1983-06-07 | 1984-12-21 | Yamanouchi Pharmaceut Co Ltd | 新規２−グアニジノチアゾリン誘導体ならびにその製造法 |
| US5177090A (en) * | 1987-07-07 | 1993-01-05 | Bayer Aktiengesellschaft | Microbicidal agents |
| FR2735128B1 (fr) * | 1995-06-07 | 1997-07-25 | Fournier Ind & Sante | Nouveaux composes de benzenesulfonamide, leur procede de preparation et utilisation en therapeutique. |
| WO2001019807A1 (fr) | 1999-09-14 | 2001-03-22 | Shionogi & Co., Ltd. | Derives de 2-imino-1,3-thiazine |
| DE10112040A1 (de) * | 2001-03-14 | 2002-10-02 | Aventis Pharma Gmbh | Verbessertes Verfahren zur Herstellung von Sulfonylcarboxamidderivaten |
| WO2005120515A2 (en) * | 2004-06-10 | 2005-12-22 | Kalypsys, Inc. | Novel sulfonamides as inhibitors of histone deacetylase for the treatment of disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3806515A (en) * | 1968-07-31 | 1974-04-23 | W Houlihan | Certain 2-alkyl-3-phenyl-5,6-dihydroimidazo(2,1-b)thiazoles |
| BE793919A (fr) * | 1972-01-12 | 1973-07-11 | Rhone Poulenc Sa | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
| DE2436263C2 (de) * | 1974-07-27 | 1983-02-17 | Hoechst Ag, 6000 Frankfurt | Thiazolidinderivate und Verfahren zu ihrer Herstellung |
-
1975
- 1975-07-29 DE DE19752533821 patent/DE2533821A1/de not_active Withdrawn
-
1976
- 1976-07-23 ES ES450070A patent/ES450070A1/es not_active Expired
- 1976-07-23 NL NL7608206A patent/NL7608206A/nl not_active Application Discontinuation
- 1976-07-27 US US05/709,075 patent/US4061647A/en not_active Expired - Lifetime
- 1976-07-27 LU LU75475A patent/LU75475A1/xx unknown
- 1976-07-27 FI FI762140A patent/FI762140A/fi not_active Application Discontinuation
- 1976-07-27 IL IL50146A patent/IL50146A/xx unknown
- 1976-07-28 AT AT555576A patent/AT353267B/de not_active IP Right Cessation
- 1976-07-28 AU AU16324/76A patent/AU498052B2/en not_active Expired
- 1976-07-28 DK DK340476A patent/DK340476A/da unknown
- 1976-07-28 CA CA257,944A patent/CA1077492A/en not_active Expired
- 1976-07-28 NO NO762625A patent/NO762625L/no unknown
- 1976-07-29 SE SE7608545A patent/SE7608545L/xx not_active Application Discontinuation
- 1976-07-29 JP JP51091186A patent/JPS5217468A/ja active Pending
- 1976-07-29 BE BE169365A patent/BE844666A/xx unknown
- 1976-07-29 FR FR7623219A patent/FR2319345A1/fr active Granted
- 1976-07-29 GB GB31655/76A patent/GB1522107A/en not_active Expired
-
1977
- 1977-08-01 ES ES461228A patent/ES461228A1/es not_active Expired
- 1977-08-01 ES ES461229A patent/ES461229A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL50146A (en) | 1979-12-30 |
| DE2533821A1 (de) | 1977-02-17 |
| FR2319345B1 (nl) | 1978-11-17 |
| AT353267B (de) | 1979-11-12 |
| ATA555576A (de) | 1979-04-15 |
| ES450070A1 (es) | 1977-12-01 |
| IL50146A0 (en) | 1976-09-30 |
| AU498052B2 (en) | 1979-02-01 |
| LU75475A1 (nl) | 1977-04-06 |
| DK340476A (da) | 1977-01-30 |
| GB1522107A (en) | 1978-08-23 |
| US4061647A (en) | 1977-12-06 |
| FR2319345A1 (fr) | 1977-02-25 |
| CA1077492A (en) | 1980-05-13 |
| SE7608545L (sv) | 1977-01-30 |
| ES461229A1 (es) | 1978-05-01 |
| BE844666A (fr) | 1977-01-31 |
| AU1632476A (en) | 1978-02-02 |
| JPS5217468A (en) | 1977-02-09 |
| NL7608206A (nl) | 1977-02-01 |
| FI762140A (nl) | 1977-01-30 |
| ES461228A1 (es) | 1978-05-01 |
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