CH617431A5 - - Google Patents

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Publication number: CH617431A5
Authority: CH; Switzerland
Prior art keywords: chloro; methyl; thiazolidin; formula; reacted
Prior art date: 1974-07-27

Application number

CH968975A

Other languages

German (de)

English (en)

Inventor

Hans-Jochen Dr Lang

Roman Dr Muschaweck

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-07-27

Filing date

1975-07-24

Publication date

1980-05-30

1975-07-24 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-05-30 Publication of CH617431A5 publication Critical patent/CH617431A5/de

Links

239000000460 chlorine Substances 0.000 claims description 344
-1 phenyl ring Halogen Chemical class 0.000 claims description 143
238000000034 method Methods 0.000 claims description 108
150000001875 compounds Chemical class 0.000 claims description 78
239000002253 acid Substances 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 21
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000003548 thiazolidines Chemical class 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 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
150000002148 esters Chemical class 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
125000005530 alkylenedioxy group Chemical group 0.000 claims 2
125000003277 amino group Chemical group 0.000 claims 2
125000004663 dialkyl amino group Chemical group 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
241000251730 Chondrichthyes Species 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
238000009413 insulation Methods 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
125000003884 phenylalkyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 152
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 131
239000013078 crystal Substances 0.000 description 88
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
239000002904 solvent Substances 0.000 description 66
239000007795 chemical reaction product Substances 0.000 description 65
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
239000007787 solid Substances 0.000 description 62
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 44
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 41
238000000354 decomposition reaction Methods 0.000 description 40
239000000203 mixture Substances 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 36
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 36
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 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
238000003756 stirring Methods 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 22
239000002244 precipitate Substances 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
150000001412 amines Chemical class 0.000 description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000002425 crystallisation Methods 0.000 description 18
230000008025 crystallization Effects 0.000 description 18
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
150000003585 thioureas Chemical class 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
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 15
FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 9
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
DQCVBUVPXOLENY-UHFFFAOYSA-N oxomethanedisulfonamide Chemical class NS(=O)(=O)C(=O)S(N)(=O)=O DQCVBUVPXOLENY-UHFFFAOYSA-N 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
HPLLGVUYBDJDBR-UHFFFAOYSA-N 2-bromo-5-(2-bromoacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CBr)=CC=C1Br HPLLGVUYBDJDBR-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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 6
150000007513 acids 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
150000002431 hydrogen Chemical group 0.000 description 6
238000002955 isolation Methods 0.000 description 6
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
238000001556 precipitation Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
DHXQAAIKVQWJRY-UHFFFAOYSA-N 2-chloro-5-(4-hydroxy-5-imino-2,3-dimethyl-1,3-thiazolidin-4-yl)benzenesulfonamide Chemical compound ClC1=C(C=C(C=C1)C1(N(C(SC1=N)C)C)O)S(N)(=O)=O DHXQAAIKVQWJRY-UHFFFAOYSA-N 0.000 description 5
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 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
239000011734 sodium Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
IFRMGNPXGGJRBD-UHFFFAOYSA-N 2-chloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonyl chloride;hydrobromide Chemical compound Br.CN1C(=NC)SCC1(O)C1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 IFRMGNPXGGJRBD-UHFFFAOYSA-N 0.000 description 4
NHCAGBOIRYHLTF-UHFFFAOYSA-N 5-(2-chloroacetyl)-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(C(=O)CCl)C=C1S(N)(=O)=O NHCAGBOIRYHLTF-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000706 filtrate Substances 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
125000000565 sulfonamide group Chemical group 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
AUXGIIVHLRLBSG-UHFFFAOYSA-N 1,3-dipropylthiourea Chemical compound CCCNC(=S)NCCC AUXGIIVHLRLBSG-UHFFFAOYSA-N 0.000 description 3
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 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
BYRBYIGGQSDHMO-UHFFFAOYSA-N 3-(2-chloroacetyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C(=O)CCl)=C1 BYRBYIGGQSDHMO-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
MJTAWGWKLXMOCO-UHFFFAOYSA-N 4-bromo-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Br MJTAWGWKLXMOCO-UHFFFAOYSA-N 0.000 description 3
LYBQQYNSZYSUMT-UHFFFAOYSA-N 4-chloro-3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 LYBQQYNSZYSUMT-UHFFFAOYSA-N 0.000 description 3
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 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003513 alkali Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-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
238000010438 heat treatment Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003495 polar organic solvent Substances 0.000 description 3
230000000054 salidiuretic effect Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 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
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-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
KREOCUNMMFZOOS-UHFFFAOYSA-N 1,3-di(propan-2-yl)thiourea Chemical compound CC(C)NC(S)=NC(C)C KREOCUNMMFZOOS-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
LUKSDHOQKVTGGT-UHFFFAOYSA-N 1-(3-amino-4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C(N)=C1 LUKSDHOQKVTGGT-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
PRZJCPQRWKZTQJ-UHFFFAOYSA-N 1-[4-chloro-3-(methylsulfamoyl)phenyl]-2-diazonioethenolate Chemical compound CNS(=O)(=O)C1=CC(C(=O)C=[N+]=[N-])=CC=C1Cl PRZJCPQRWKZTQJ-UHFFFAOYSA-N 0.000 description 2
BHJBCSJWIZQRQZ-UHFFFAOYSA-N 2-chloro-5-(2-chloroacetyl)-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl BHJBCSJWIZQRQZ-UHFFFAOYSA-N 0.000 description 2
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DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
JJYJHBDNTYTPEJ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-chloro-5-(4-hydroxy-3-methyl-2-methylimino-1,3-thiazolidin-4-yl)benzenesulfonamide Chemical compound CN1C(=NC)SCC1(O)C1=CC=C(Cl)C(S(=O)(=O)NCC=2C=C3OCOC3=CC=2)=C1 JJYJHBDNTYTPEJ-UHFFFAOYSA-N 0.000 description 1
NFVVJOWYXNNVHY-UHFFFAOYSA-N n-benzyl-5-(2-bromoacetyl)-2-chlorobenzenesulfonamide Chemical compound ClC1=CC=C(C(=O)CBr)C=C1S(=O)(=O)NCC1=CC=CC=C1 NFVVJOWYXNNVHY-UHFFFAOYSA-N 0.000 description 1
PSNALKXXHKFUET-UHFFFAOYSA-N n-butyl-2-chloro-5-(2-chloroacetyl)benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl PSNALKXXHKFUET-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
IKHALSGRXLOXLP-UHFFFAOYSA-N n-tert-butyl-2-chloro-5-(2-chloroacetyl)benzenesulfonamide Chemical compound CC(C)(C)NS(=O)(=O)C1=CC(C(=O)CCl)=CC=C1Cl IKHALSGRXLOXLP-UHFFFAOYSA-N 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
XHIHKTCUUHGKSF-UHFFFAOYSA-N piperidine-1-carbothiohydrazide Chemical compound NNC(=S)N1CCCCC1 XHIHKTCUUHGKSF-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 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
159000000001 potassium salts Chemical class 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
MGYXPFHVGMHTGE-UHFFFAOYSA-N quinazolin-3-ium;bromide Chemical compound Br.N1=CN=CC2=CC=CC=C21 MGYXPFHVGMHTGE-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 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
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
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000001984 thiazolidinyl group Chemical group 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 group 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
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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH968975A 1974-07-27 1975-07-24 CH617431A5 (hu)

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 (1)

Publication Number	Publication Date
CH617431A5 true CH617431A5 (hu)	1980-05-30

Family

ID=5921709

Family Applications (4)

Application Number	Title	Priority Date
CH968975A CH617431A5 (hu)	1974-07-27	1975-07-24
CH1079979A CH623316A5 (hu)	1974-07-27	1979-12-05
CH1079879A CH624678A5 (hu)	1974-07-27	1979-12-05
CH1079779A CH624677A5 (hu)	1974-07-27	1979-12-05

Family Applications After (3)

Application Number	Title	Priority Date
CH1079979A CH623316A5 (hu)	1974-07-27	1979-12-05
CH1079879A CH624678A5 (hu)	1974-07-27	1979-12-05
CH1079779A CH624677A5 (hu)	1974-07-27	1979-12-05

Country Status (25)

Country	Link
US (1)	US4061761A (hu)
JP (1)	JPS606945B2 (hu)
AT (1)	AT344160B (hu)
AU (1)	AU501320B2 (hu)
BE (1)	BE831794A (hu)
CA (1)	CA1054596A (hu)
CH (4)	CH617431A5 (hu)
CY (1)	CY1008A (hu)
DD (1)	DD121112A5 (hu)
DE (1)	DE2436263C2 (hu)
DK (1)	DK145626C (hu)
ES (5)	ES439593A1 (hu)
FI (1)	FI61487C (hu)
FR (1)	FR2282882A1 (hu)
GB (1)	GB1513948A (hu)
HK (1)	HK40579A (hu)
HU (1)	HU172659B (hu)
IE (1)	IE42441B1 (hu)
IL (1)	IL47779A (hu)
LU (1)	LU73069A1 (hu)
MX (1)	MX3514E (hu)
NL (1)	NL181711C (hu)
NO (1)	NO144528C (hu)
SE (1)	SE431207B (hu)
ZA (1)	ZA754772B (hu)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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
KR100509401B1 (ko)	1999-09-14	2005-08-22	시오노기세이야쿠가부시키가이샤	2-이미노-1,3-티아진 유도체
CN1798733A (zh) *	2003-06-10	2006-07-05	凯利普西斯公司	作为组蛋白脱乙酰基酶抑制剂的疾病治疗用羰基化合物
WO2005120515A2 (en) *	2004-06-10	2005-12-22	Kalypsys, Inc.	Novel sulfonamides as inhibitors of histone deacetylase for the treatment of disease
WO2018224455A1 (en)	2017-06-07	2018-12-13	Basf Se	Substituted cyclopropyl derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 CY CY1008A patent/CY1008A/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 GB GB30973/75A patent/GB1513948A/en not_active Expired
- 1975-07-24 HU HU75HO00001821A patent/HU172659B/hu unknown
- 1975-07-24 ZA ZA00754772A patent/ZA754772B/xx unknown
- 1975-07-24 NL NLAANVRAGE7508848,A patent/NL181711C/xx not_active IP Right Cessation
- 1975-07-25 NO NO752636A patent/NO144528C/no unknown
- 1975-07-25 DK DK340475A patent/DK145626C/da not_active IP Right Cessation
- 1975-07-25 IE IE1668/75A patent/IE42441B1/en unknown
- 1975-07-25 AT AT577075A patent/AT344160B/de not_active IP Right Cessation
- 1975-07-25 SE SE7508476A patent/SE431207B/xx 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 MX MX756375U patent/MX3514E/es unknown
- 1975-07-25 DD DD187482A patent/DD121112A5/xx unknown
- 1975-07-25 US US05/599,103 patent/US4061761A/en not_active Expired - Lifetime
- 1975-07-25 CA CA232295A patent/CA1054596A/en not_active Expired
- 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 ES455018A patent/ES455018A1/es not_active Expired
- 1977-01-14 ES ES455020A patent/ES455020A1/es not_active Expired
- 1977-01-14 ES ES455015A patent/ES455015A1/es not_active Expired
- 1977-01-14 ES ES455019A patent/ES455019A1/es not_active Expired
1979
- 1979-06-21 HK HK405/79A patent/HK40579A/xx unknown
- 1979-12-05 CH CH1079979A patent/CH623316A5/de not_active IP Right Cessation
- 1979-12-05 CH CH1079879A patent/CH624678A5/de not_active IP Right Cessation
- 1979-12-05 CH CH1079779A patent/CH624677A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HK40579A (en)	1979-06-29
US4061761A (en)	1977-12-06
JPS5154555A (hu)	1976-05-13
AT344160B (de)	1978-07-10
IL47779A0 (en)	1975-10-15
ATA577075A (de)	1977-11-15
AU501320B2 (en)	1979-06-14
IL47779A (en)	1979-01-31
DE2436263C2 (de)	1983-02-17
ES455020A1 (es)	1977-12-16
FI752131A (hu)	1976-01-28
CY1008A (en)	1979-08-02
SE7508476L (sv)	1976-01-28
SE431207B (sv)	1984-01-23
CA1054596A (en)	1979-05-15
ZA754772B (en)	1976-06-30
NL181711B (nl)	1987-05-18
AU8339175A (en)	1977-01-27
ES439593A1 (es)	1977-06-16
FI61487B (fi)	1982-04-30
IE42441B1 (en)	1980-08-13
ES455019A1 (es)	1977-12-16
HU172659B (hu)	1978-11-28
LU73069A1 (hu)	1977-03-24
FR2282882A1 (fr)	1976-03-26
NO144528C (no)	1981-09-23
NL7508848A (nl)	1976-01-29
MX3514E (es)	1981-01-14
FI61487C (fi)	1982-08-10
DE2436263A1 (de)	1976-02-12
JPS606945B2 (ja)	1985-02-21
CH624678A5 (hu)	1981-08-14
DK340475A (da)	1976-01-28
NO752636L (hu)	1976-01-28
CH623316A5 (hu)	1981-05-29
CH624677A5 (hu)	1981-08-14
ES455018A1 (es)	1977-12-16
BE831794A (fr)	1976-01-28
NL181711C (nl)	1987-10-16
GB1513948A (en)	1978-06-14
IE42441L (en)	1976-01-27
DK145626C (da)	1983-08-01
ES455015A1 (es)	1977-12-16
DK145626B (da)	1983-01-03
NO144528B (no)	1981-06-09
FR2282882B1 (hu)	1979-08-10
DD121112A5 (hu)	1976-07-12

Publication	Publication Date	Title
DD200371A5 (de)	1983-04-20	Verfahren zur herstellung von 2,4-disubstituierten thiazolen
DE3218584A1 (de)	1982-12-23	1,2-diaminocyclobuten-3,4-dione, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten
DE2322880C2 (de)	1982-09-23	4-(Imidazolin-2-ylamino)-2,1,3-benzothiadiazole und Verfahren zu deren Herstellung
EP0041215B1 (de)	1986-01-29	Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
CH617431A5 (hu)	1980-05-30
DE2533821A1 (de)	1977-02-17	Thiazolidinderivate und verfahren zu ihrer herstellung
DE2926771A1 (de)	1981-01-15	Thiazolidinderivate und verfahren zu ihrer herstellung
DE3135250A1 (de)	1983-03-17	Tricyclische thiazolyloxamate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel
EP0055458A2 (de)	1982-07-07	Thiazolinderivate, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen
DD249479A5 (de)	1987-09-09	Verfahren zur herstellung von propionamidin-derivaten
CH629800A5 (de)	1982-05-14	Verfahren zur herstellung von 1-substituierten 2,4-imidazolidindionen.
DE2546165A1 (de)	1977-04-28	Thiazolidinderivate und verfahren zu ihrer herstellung
DE1545810A1 (de)	1969-12-11	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
AT360520B (de)	1981-01-12	Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen
DE2656227C2 (de)	1985-07-04	Basisch alkylierte Diphenyldisulfid-2,2'-biscarbonsäureamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0160173A1 (de)	1985-11-06	Benzothiazolderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltendes Arzneimittel
DE2601598A1 (de)	1977-07-21	Thiazolidinderivate und verfahren zu ihrer herstellung
AT360985B (de)	1981-02-10	Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen
DE2114563A1 (de)	1971-10-14	Substituierte 6 Phenyl imidazo eckige Klammer auf 2,1 b eckige Klammer zu thiazole
AT361473B (de)	1981-03-10	Verfahren zur herstellung von neuen thiazoli- dinderivaten und von deren saeureadditionssalzen
DE1620285A1 (de)	1970-03-12	Verfahren zur Herstellung von Thiazolverbindungen
DE3121137A1 (de)	1982-12-16	Neue pyridazino(4,5-b)indole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und deren herstellung"
AT360522B (de)	1981-01-12	Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen
EP0365913A2 (de)	1990-05-02	Substituierte 2-Aminothiazole
DE3710254A1 (de)	1988-10-06	Antiulcusmittel

Legal Events

Date	Code	Title	Description
1993-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased