DE2436263C2 - Thiazolidinderivate und Verfahren zu ihrer Herstellung - Google Patents
Thiazolidinderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2436263C2 DE2436263C2 DE2436263A DE2436263A DE2436263C2 DE 2436263 C2 DE2436263 C2 DE 2436263C2 DE 2436263 A DE2436263 A DE 2436263A DE 2436263 A DE2436263 A DE 2436263A DE 2436263 C2 DE2436263 C2 DE 2436263C2
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- methyl
- compounds
- thiazolidin
- hydrochloride
- 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
- 238000000034 method Methods 0.000 title claims description 47
- 150000003548 thiazolidines Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 alkyl radicals Chemical class 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 89
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 86
- 239000007795 chemical reaction product Substances 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 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
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000000054 salidiuretic effect Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 241000251730 Chondrichthyes Species 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 150
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
- 239000013078 crystal Substances 0.000 description 85
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- 239000002904 solvent Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000007787 solid Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 37
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- TXNZZKXIJJSNFH-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CBr)=CC=C1Cl TXNZZKXIJJSNFH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 16
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
- QTFDRWZRUOIWQI-UHFFFAOYSA-N 2-chloro-5-(2-chloroacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl QTFDRWZRUOIWQI-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 8
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- SJYNPNGXTMVCKZ-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-chloro-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(C(=O)CBr)=CC=C1Cl SJYNPNGXTMVCKZ-UHFFFAOYSA-N 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 229940032007 methylethyl ketone Drugs 0.000 description 5
- 230000001376 precipitating effect Effects 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
- XWIWYJKLMNGMLH-UHFFFAOYSA-N 5-acetyl-2-chlorobenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 XWIWYJKLMNGMLH-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- DOEOICBYDBQMJP-UHFFFAOYSA-N 2-chloro-5-(2-chloroacetyl)-n,n-dipropylbenzenesulfonamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl DOEOICBYDBQMJP-UHFFFAOYSA-N 0.000 description 3
- AJOZXZIGCOTPKZ-UHFFFAOYSA-N 2-chloro-5-(2-chloroacetyl)-n-cyclohexylbenzenesulfonamide Chemical compound ClCC(=O)C1=CC=C(Cl)C(S(=O)(=O)NC2CCCCC2)=C1 AJOZXZIGCOTPKZ-UHFFFAOYSA-N 0.000 description 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- XALXFSQVBICFKL-UHFFFAOYSA-N 4-propan-2-yl-3-sulfamoylbenzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1S(N)(=O)=O XALXFSQVBICFKL-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- DYFKIIYDHGJXCC-UHFFFAOYSA-N n,n-dibutyl-2-chloro-5-(2-chloroacetyl)benzenesulfonamide Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl DYFKIIYDHGJXCC-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- NVHNGVXBCWYLFA-UHFFFAOYSA-N 1,3-diazinane-2-thione Chemical compound S=C1NCCCN1 NVHNGVXBCWYLFA-UHFFFAOYSA-N 0.000 description 2
- UUEZMFJKFJEZTG-UHFFFAOYSA-N 1,3-thiazolidin-4-ol Chemical compound OC1CSCN1 UUEZMFJKFJEZTG-UHFFFAOYSA-N 0.000 description 2
- GRHOQUWZOWFAPK-UHFFFAOYSA-N 1-[4-chloro-3-(diethylsulfamoyl)phenyl]-2-diazonioethenolate Chemical compound CCN(CC)S(=O)(=O)C1=CC(C(=O)C=[N+]=[N-])=CC=C1Cl GRHOQUWZOWFAPK-UHFFFAOYSA-N 0.000 description 2
- MFGDJIMFIMXEDX-UHFFFAOYSA-N 1-[4-chloro-3-(dimethylsulfamoyl)phenyl]-2-diazonioethenolate Chemical compound CN(C)S(=O)(=O)C1=CC(C(=O)C=[N+]=[N-])=CC=C1Cl MFGDJIMFIMXEDX-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- OTVGARFFAAFRAC-UHFFFAOYSA-N 2-bromo-1,4-dioxane Chemical compound BrC1COCCO1 OTVGARFFAAFRAC-UHFFFAOYSA-N 0.000 description 2
- YDYHQYNKGWFJOG-UHFFFAOYSA-N 2-bromo-5-(2-chloroacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Br YDYHQYNKGWFJOG-UHFFFAOYSA-N 0.000 description 2
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- 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
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- YYCPSEFQLGXPCO-UHFFFAOYSA-N xi-p-Menth-3-ene Chemical compound CC(C)C1=CCC(C)CC1 YYCPSEFQLGXPCO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- 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
- 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
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (37)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2436263A DE2436263C2 (de) | 1974-07-27 | 1974-07-27 | Thiazolidinderivate und Verfahren zu ihrer Herstellung |
| ES439593A ES439593A1 (es) | 1974-07-27 | 1975-07-21 | Procedimiento para la preparacion de derivados de tiazolidi-na. |
| IL47779A IL47779A (en) | 1974-07-27 | 1975-07-23 | 2,3-disubstituted-4-(3-sulfamoylphenyl)thiazolidin-4-ol derivatives and process for their manufacture |
| NLAANVRAGE7508848,A NL181711C (nl) | 1974-07-27 | 1975-07-24 | Werkwijze voor de bereiding van een farmaceutisch preparaat met salidiuretische werking, alsmede voor de bereiding van verbindingen, geschikt voor gebruik in deze preparaten. |
| ZA00754772A ZA754772B (en) | 1974-07-27 | 1975-07-24 | Thiazolidine derivatives and process for their manufacture |
| HU75HO00001821A HU172659B (hu) | 1974-07-27 | 1975-07-24 | Sposob poluchenija proizvodnykh tiazolidina i farmacevticheskikh kompozicijj soderzhahhikh ikh aktivnymi agentami |
| CH968975A CH617431A5 (en, 2012) | 1974-07-27 | 1975-07-24 | |
| GB30973/75A GB1513948A (en) | 1974-07-27 | 1975-07-24 | Thiazolidine derivatives and process for their manufactur |
| CY1008A CY1008A (en) | 1974-07-27 | 1975-07-24 | Thiazolidine derivatives and process for their manufacture |
| FI752131A FI61487C (fi) | 1974-07-27 | 1975-07-24 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-3-sulfamoylfenyl)-4-hydroxi-1,3-tiatzolidin-derivat |
| LU73069A LU73069A1 (en, 2012) | 1974-07-27 | 1975-07-25 | |
| AU83391/75A AU501320B2 (en) | 1974-07-27 | 1975-07-25 | Thiazole derivatives |
| DK340475A DK145626C (da) | 1974-07-27 | 1975-07-25 | Analogifremgangsmaade til fremstilling af thiazolidinderivater |
| IE1668/75A IE42441B1 (en) | 1974-07-27 | 1975-07-25 | Thiazolidine derivatives and process for their manufacture |
| AT577075A AT344160B (de) | 1974-07-27 | 1975-07-25 | Verfahren zur herstellung neuer thiazolidinderivate und ihrer salze |
| DD187482A DD121112A5 (en, 2012) | 1974-07-27 | 1975-07-25 | |
| SE7508476A SE431207B (sv) | 1974-07-27 | 1975-07-25 | Forfarande for framstellning av tiazolidinderivat |
| US05/599,103 US4061761A (en) | 1974-07-27 | 1975-07-25 | Thiazolidine derivatives |
| NO752636A NO144528C (no) | 1974-07-27 | 1975-07-25 | Analogifremgangsmaate til fremstilling av thiazolidinderivater med diuretisk og saluretisk virkning |
| CA232295A CA1054596A (en) | 1974-07-27 | 1975-07-25 | Thiazolidine derivatives and process for their manufacture |
| MX756375U MX3514E (es) | 1974-07-27 | 1975-07-25 | Procedimiento para la preparacion de derivados de 1,3 tiazolidinas |
| JP50090729A JPS606945B2 (ja) | 1974-07-27 | 1975-07-26 | チアゾリジン誘導体の製造方法 |
| BE158662A BE831794A (fr) | 1974-07-27 | 1975-07-28 | Derives de thiazolidine, leur procede de preparation et leurs application |
| FR7523498A FR2282882A1 (fr) | 1974-07-27 | 1975-07-28 | Derives de thiazolidine, leur procede de preparation et leurs applications |
| ES455015A ES455015A1 (es) | 1974-07-27 | 1977-01-14 | Procedimiento para la preparacion de derivados de tiazolidi-na. |
| ES455020A ES455020A1 (es) | 1974-07-27 | 1977-01-14 | Procedimiento para la preparacion de derivados de tiazolidi-na. |
| ES455019A ES455019A1 (es) | 1974-07-27 | 1977-01-14 | Procedimiento para la preparacion de derivados de tiazolidi-na. |
| ES455018A ES455018A1 (es) | 1974-07-27 | 1977-01-14 | Procedimiento para la preparacion de derivados de tiazolidi-na. |
| US05/788,905 US4125614A (en) | 1974-07-27 | 1977-04-19 | Thiazolidine derivatives |
| AT781477A AT360520B (de) | 1974-07-27 | 1977-11-02 | Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen |
| AT781577A AT360985B (de) | 1974-07-27 | 1977-11-02 | Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen |
| AT781677A AT360521B (de) | 1974-07-27 | 1977-11-02 | Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen |
| AT781777A AT360522B (de) | 1974-07-27 | 1977-11-02 | Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen |
| HK405/79A HK40579A (en) | 1974-07-27 | 1979-06-21 | Thiazolidine derivatives and process for their manufacture |
| CH1079879A CH624678A5 (en, 2012) | 1974-07-27 | 1979-12-05 | |
| CH1079979A CH623316A5 (en, 2012) | 1974-07-27 | 1979-12-05 | |
| CH1079779A CH624677A5 (en, 2012) | 1974-07-27 | 1979-12-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2436263A DE2436263C2 (de) | 1974-07-27 | 1974-07-27 | Thiazolidinderivate und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2436263A1 DE2436263A1 (de) | 1976-02-12 |
| DE2436263C2 true DE2436263C2 (de) | 1983-02-17 |
Family
ID=5921709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2436263A Expired DE2436263C2 (de) | 1974-07-27 | 1974-07-27 | Thiazolidinderivate und Verfahren zu ihrer Herstellung |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4061761A (en, 2012) |
| JP (1) | JPS606945B2 (en, 2012) |
| AT (1) | AT344160B (en, 2012) |
| AU (1) | AU501320B2 (en, 2012) |
| BE (1) | BE831794A (en, 2012) |
| CA (1) | CA1054596A (en, 2012) |
| CH (4) | CH617431A5 (en, 2012) |
| CY (1) | CY1008A (en, 2012) |
| DD (1) | DD121112A5 (en, 2012) |
| DE (1) | DE2436263C2 (en, 2012) |
| DK (1) | DK145626C (en, 2012) |
| ES (5) | ES439593A1 (en, 2012) |
| FI (1) | FI61487C (en, 2012) |
| FR (1) | FR2282882A1 (en, 2012) |
| GB (1) | GB1513948A (en, 2012) |
| HK (1) | HK40579A (en, 2012) |
| HU (1) | HU172659B (en, 2012) |
| IE (1) | IE42441B1 (en, 2012) |
| IL (1) | IL47779A (en, 2012) |
| LU (1) | LU73069A1 (en, 2012) |
| MX (1) | MX3514E (en, 2012) |
| NL (1) | NL181711C (en, 2012) |
| NO (1) | NO144528C (en, 2012) |
| SE (1) | SE431207B (en, 2012) |
| ZA (1) | ZA754772B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2533821A1 (de) * | 1975-07-29 | 1977-02-17 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| 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 |
| DE4127737A1 (de) | 1991-08-22 | 1993-02-25 | Hoechst Ag | Arzneimittel zur behandlung von abstossungsreaktionen bei organverpflanzungen |
| ATE393150T1 (de) | 1999-09-14 | 2008-05-15 | Shionogi & Co | 2-imino-1,3-thiazin-derivate |
| CA2528003A1 (en) * | 2003-06-10 | 2004-12-23 | Kalypsys, Inc. | Carbonyl compounds as inhibitors of histone deacetylase for the treatment of disease |
| JP2008515777A (ja) * | 2004-06-10 | 2008-05-15 | カリプシス・インコーポレーテッド | 疾患治療用のヒストンデアセチラーゼ阻害剤としての新規スルホンアミド |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH513918A (de) * | 1968-07-31 | 1971-10-15 | Sandoz Ag | Verfahren zur Herstellung von 2-n-Alkyl-3-phenyl-6,7-dihydro-5H-thiazolo(3,2-a)pyrimidinen bzw. 2-n-Alkyl-3-phenyl-5,6-dihydroimidazo(2,1-b)thiazolen |
| CH520702A (de) * | 1968-11-29 | 1972-03-31 | Sandoz Ag | Verfahren zur Herstellung von 4-Phenyl-3-alkyl-2-alkyl-iminothiazolidin-4-olen |
| US3652577A (en) * | 1969-07-28 | 1972-03-28 | Sandoz Ag | Certain 3-alkyl-2-alkylimino-4-halo-phenylthiazolidin-4-ols |
| US3704240A (en) * | 1971-03-17 | 1972-11-28 | American Home Prod | 3-substituted-4-hydroxy - 2 - substituted imino - 4 - phenyl-5-thiazolidine alkyl carboxylic acids and their alkyl esters |
-
1974
- 1974-07-27 DE DE2436263A patent/DE2436263C2/de not_active Expired
-
1975
- 1975-07-21 ES ES439593A patent/ES439593A1/es not_active Expired
- 1975-07-23 IL IL47779A patent/IL47779A/xx unknown
- 1975-07-24 CH CH968975A patent/CH617431A5/de not_active IP Right Cessation
- 1975-07-24 FI FI752131A patent/FI61487C/fi not_active IP Right Cessation
- 1975-07-24 HU HU75HO00001821A patent/HU172659B/hu unknown
- 1975-07-24 GB GB30973/75A patent/GB1513948A/en not_active Expired
- 1975-07-24 NL NLAANVRAGE7508848,A patent/NL181711C/xx not_active IP Right Cessation
- 1975-07-24 ZA ZA00754772A patent/ZA754772B/xx unknown
- 1975-07-24 CY CY1008A patent/CY1008A/xx unknown
- 1975-07-25 DK DK340475A patent/DK145626C/da not_active IP Right Cessation
- 1975-07-25 CA CA232295A patent/CA1054596A/en not_active Expired
- 1975-07-25 AT AT577075A patent/AT344160B/de not_active IP Right Cessation
- 1975-07-25 LU LU73069A patent/LU73069A1/xx unknown
- 1975-07-25 AU AU83391/75A patent/AU501320B2/en not_active Expired
- 1975-07-25 SE SE7508476A patent/SE431207B/xx not_active IP Right Cessation
- 1975-07-25 US US05/599,103 patent/US4061761A/en not_active Expired - Lifetime
- 1975-07-25 MX MX756375U patent/MX3514E/es unknown
- 1975-07-25 NO NO752636A patent/NO144528C/no unknown
- 1975-07-25 DD DD187482A patent/DD121112A5/xx unknown
- 1975-07-25 IE IE1668/75A patent/IE42441B1/en unknown
- 1975-07-26 JP JP50090729A patent/JPS606945B2/ja not_active Expired
- 1975-07-28 FR FR7523498A patent/FR2282882A1/fr active Granted
- 1975-07-28 BE BE158662A patent/BE831794A/xx not_active IP Right Cessation
-
1977
- 1977-01-14 ES ES455020A patent/ES455020A1/es not_active Expired
- 1977-01-14 ES ES455019A patent/ES455019A1/es not_active Expired
- 1977-01-14 ES ES455015A patent/ES455015A1/es not_active Expired
- 1977-01-14 ES ES455018A patent/ES455018A1/es not_active Expired
-
1979
- 1979-06-21 HK HK405/79A patent/HK40579A/xx unknown
- 1979-12-05 CH CH1079879A patent/CH624678A5/de not_active IP Right Cessation
- 1979-12-05 CH CH1079979A patent/CH623316A5/de not_active IP Right Cessation
- 1979-12-05 CH CH1079779A patent/CH624677A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |