JPS606945B2 - チアゾリジン誘導体の製造方法 - Google Patents
チアゾリジン誘導体の製造方法Info
- Publication number
- JPS606945B2 JPS606945B2 JP50090729A JP9072975A JPS606945B2 JP S606945 B2 JPS606945 B2 JP S606945B2 JP 50090729 A JP50090729 A JP 50090729A JP 9072975 A JP9072975 A JP 9072975A JP S606945 B2 JPS606945 B2 JP S606945B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- alkyl
- chloro
- formula
- 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
- 150000003548 thiazolidines Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 141
- 238000000034 method Methods 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 239000002253 acid Substances 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 8
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 179
- 230000008018 melting Effects 0.000 description 179
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 141
- 239000013078 crystal Substances 0.000 description 99
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
- -1 halogen ketone Chemical class 0.000 description 85
- 239000000047 product Substances 0.000 description 84
- 238000006243 chemical reaction Methods 0.000 description 82
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 77
- 239000002904 solvent Substances 0.000 description 75
- 239000007787 solid Substances 0.000 description 59
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 238000003756 stirring Methods 0.000 description 57
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000000354 decomposition reaction Methods 0.000 description 43
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 39
- 239000002244 precipitate Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 30
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 29
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000010626 work up procedure Methods 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 229910052717 sulfur Inorganic materials 0.000 description 22
- 239000011593 sulfur Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 17
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VYBZOPZNLLIEFX-UHFFFAOYSA-N 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(N)(=O)=O)=C1 VYBZOPZNLLIEFX-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 14
- 229960004592 isopropanol Drugs 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 150000002431 hydrogen Chemical class 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 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
- 239000000284 extract Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- 239000008280 blood Substances 0.000 description 10
- 210000004369 blood Anatomy 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 229910000831 Steel Inorganic materials 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- AKILUNHERNPUIT-UHFFFAOYSA-N 1,3-thiazolidin-4-ol hydrobromide Chemical compound Br.OC1CSCN1 AKILUNHERNPUIT-UHFFFAOYSA-N 0.000 description 6
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 238000002955 isolation Methods 0.000 description 6
- 150000007522 mineralic acids 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
- 239000000725 suspension Substances 0.000 description 6
- HWALZZPNGXHTQE-UHFFFAOYSA-N 2-oxo-2-phenylethanesulfonamide Chemical compound NS(=O)(=O)CC(=O)C1=CC=CC=C1 HWALZZPNGXHTQE-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 229940032007 methylethyl ketone Drugs 0.000 description 5
- DQCVBUVPXOLENY-UHFFFAOYSA-N oxomethanedisulfonamide Chemical compound NS(=O)(=O)C(=O)S(N)(=O)=O DQCVBUVPXOLENY-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 description 4
- UUEZMFJKFJEZTG-UHFFFAOYSA-N 1,3-thiazolidin-4-ol Chemical compound OC1CSCN1 UUEZMFJKFJEZTG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ZSTBZBURMWJKSQ-UHFFFAOYSA-N 2-diazonio-1-phenylethenolate Chemical compound N#[N+]C=C([O-])C1=CC=CC=C1 ZSTBZBURMWJKSQ-UHFFFAOYSA-N 0.000 description 4
- ZLZNHLVBJWGUCV-UHFFFAOYSA-N 3-acetylbenzenesulfonamide Chemical compound CC(=O)C1=CC=CC(S(N)(=O)=O)=C1 ZLZNHLVBJWGUCV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 4
- HCRFWYZOCVHRHI-UHFFFAOYSA-N Cl.OC1CSCN1 Chemical compound Cl.OC1CSCN1 HCRFWYZOCVHRHI-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-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
- 241000594009 Phoxinus phoxinus Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000004108 freeze drying 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 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
- 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 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-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
- 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 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
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- 238000004094 preconcentration Methods 0.000 description 1
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- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-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
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- 239000002994 raw material Substances 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004071 soot Substances 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
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- GHAKYKGFKFZYSJ-UHFFFAOYSA-N sulfonylmethanone Chemical compound O=C=S(=O)=O GHAKYKGFKFZYSJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 150000007970 thio esters 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
- 150000003585 thioureas Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 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
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- 229910052721 tungsten Inorganic materials 0.000 description 1
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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
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- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2436263A DE2436263C2 (de) | 1974-07-27 | 1974-07-27 | Thiazolidinderivate und Verfahren zu ihrer Herstellung |
| DE2436263.8 | 1974-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5154555A JPS5154555A (en, 2012) | 1976-05-13 |
| JPS606945B2 true JPS606945B2 (ja) | 1985-02-21 |
Family
ID=5921709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50090729A Expired JPS606945B2 (ja) | 1974-07-27 | 1975-07-26 | チアゾリジン誘導体の製造方法 |
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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