NO770123L - Tiazolidinderivater og fremgangsm}te til deres fremstilling. - Google Patents
Tiazolidinderivater og fremgangsm}te til deres fremstilling.Info
- Publication number
- NO770123L NO770123L NO770123A NO770123A NO770123L NO 770123 L NO770123 L NO 770123L NO 770123 A NO770123 A NO 770123A NO 770123 A NO770123 A NO 770123A NO 770123 L NO770123 L NO 770123L
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- sulfamoyl
- phenyl
- methyl
- thiazolidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title description 5
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- -1 alkenyl radicals Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000003585 thioureas Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000007514 bases Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 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
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003548 thiazolidines Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000000054 salidiuretic effect Effects 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940125890 compound Ia Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 90
- 230000008018 melting Effects 0.000 description 83
- 238000002844 melting Methods 0.000 description 83
- 239000013078 crystal Substances 0.000 description 65
- 229910052757 nitrogen Inorganic materials 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 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 37
- 238000006243 chemical reaction Methods 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- AKILUNHERNPUIT-UHFFFAOYSA-N 1,3-thiazolidin-4-ol hydrobromide Chemical compound Br.OC1CSCN1 AKILUNHERNPUIT-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 230000001376 precipitating effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 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 9
- 235000011054 acetic acid Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JTGRVEPHPHGJJL-UHFFFAOYSA-N 1,1-diethyl-3-methylthiourea Chemical compound CCN(CC)C(=S)NC JTGRVEPHPHGJJL-UHFFFAOYSA-N 0.000 description 8
- 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 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- MRIAUTADXDMLTL-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-chloro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(C(=O)CBr)=CC=C1Cl MRIAUTADXDMLTL-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- HXMRAWVFMYZQMG-UHFFFAOYSA-N 1,1,3-triethylthiourea Chemical compound CCNC(=S)N(CC)CC HXMRAWVFMYZQMG-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- SGDFFVULOHZPOM-UHFFFAOYSA-N 1-benzyl-1,3-dimethylthiourea Chemical compound CNC(=S)N(C)CC1=CC=CC=C1 SGDFFVULOHZPOM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KWRGMBARTDLYSH-UHFFFAOYSA-N 1-methyl-1,3-diazinane-2-thione Chemical compound CN1CCCNC1=S KWRGMBARTDLYSH-UHFFFAOYSA-N 0.000 description 2
- FFFWTYSDVPXMMS-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-chloro-n-[(4-methylphenyl)methyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1CNS(=O)(=O)C1=CC(C(=O)CBr)=CC=C1Cl FFFWTYSDVPXMMS-UHFFFAOYSA-N 0.000 description 2
- QMVXETWPNTWXPR-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-chloro-n-cyclopentylbenzenesulfonamide Chemical compound ClC1=CC=C(C(=O)CBr)C=C1S(=O)(=O)NC1CCCC1 QMVXETWPNTWXPR-UHFFFAOYSA-N 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HCRFWYZOCVHRHI-UHFFFAOYSA-N Cl.OC1CSCN1 Chemical compound Cl.OC1CSCN1 HCRFWYZOCVHRHI-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- DXSZIMFJWIEWOM-UHFFFAOYSA-N 1,1-dibenzyl-3-methylthiourea Chemical compound C=1C=CC=CC=1CN(C(=S)NC)CC1=CC=CC=C1 DXSZIMFJWIEWOM-UHFFFAOYSA-N 0.000 description 1
- MTTGURFUUQWHOU-UHFFFAOYSA-N 1,1-dibutyl-3-methylthiourea Chemical compound CCCCN(C(=S)NC)CCCC MTTGURFUUQWHOU-UHFFFAOYSA-N 0.000 description 1
- JMCSJPUTHBFMGO-UHFFFAOYSA-N 1,1-dicyclohexyl-3-ethylthiourea Chemical compound C1CCCCC1N(C(=S)NCC)C1CCCCC1 JMCSJPUTHBFMGO-UHFFFAOYSA-N 0.000 description 1
- PWYOYWXAWZAAFF-UHFFFAOYSA-N 1,1-diethyl-3-propan-2-ylthiourea Chemical compound CCN(CC)C(=S)NC(C)C PWYOYWXAWZAAFF-UHFFFAOYSA-N 0.000 description 1
- AMLHPXYPXKPEBN-UHFFFAOYSA-N 1,3-dimethyl-1-(2-phenylethyl)thiourea Chemical compound CNC(=S)N(C)CCC1=CC=CC=C1 AMLHPXYPXKPEBN-UHFFFAOYSA-N 0.000 description 1
- XOERABXRVAVTCE-UHFFFAOYSA-N 1,3-dimethyl-1-phenylthiourea Chemical compound CNC(=S)N(C)C1=CC=CC=C1 XOERABXRVAVTCE-UHFFFAOYSA-N 0.000 description 1
- PADSUCARJVBITF-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-1-butyl-3-methylthiourea Chemical compound CCCCN(C(=S)NC)CC1=CC=C2OCOC2=C1 PADSUCARJVBITF-UHFFFAOYSA-N 0.000 description 1
- YXZHNWHUVIXZIX-UHFFFAOYSA-N 1-(1-hydroxy-1-phenylpropan-2-yl)-1,3-dimethylthiourea Chemical compound CNC(=S)N(C)C(C)C(O)C1=CC=CC=C1 YXZHNWHUVIXZIX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/10—Oxygen or 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (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)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762601598 DE2601598A1 (de) | 1976-01-17 | 1976-01-17 | Thiazolidinderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO770123L true NO770123L (no) | 1977-07-19 |
Family
ID=5967632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770123A NO770123L (no) | 1976-01-17 | 1977-01-14 | Tiazolidinderivater og fremgangsm}te til deres fremstilling. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4118501A (de) |
| JP (1) | JPS5293742A (de) |
| AT (1) | AT354440B (de) |
| AU (1) | AU2134277A (de) |
| BE (1) | BE850451A (de) |
| CA (1) | CA1089472A (de) |
| DE (1) | DE2601598A1 (de) |
| DK (1) | DK14877A (de) |
| ES (1) | ES454934A1 (de) |
| FI (1) | FI770109A7 (de) |
| FR (1) | FR2338269A1 (de) |
| GB (1) | GB1570912A (de) |
| HU (1) | HU176109B (de) |
| IL (1) | IL51263A (de) |
| IT (1) | IT1076221B (de) |
| LU (1) | LU76579A1 (de) |
| NL (1) | NL7700259A (de) |
| NO (1) | NO770123L (de) |
| SE (1) | SE7700436L (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652577A (en) * | 1969-07-28 | 1972-03-28 | Sandoz Ag | Certain 3-alkyl-2-alkylimino-4-halo-phenylthiazolidin-4-ols |
| US3660418A (en) * | 1970-03-16 | 1972-05-02 | Sandoz Ag | Certain 2 3 5 6-tetrahydroimidazo(2 1-b)thiazoles |
| 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 |
-
0
- SE SE7700436A patent/SE7700436L/sv unknown
-
1976
- 1976-01-17 DE DE19762601598 patent/DE2601598A1/de not_active Withdrawn
-
1977
- 1977-01-11 ES ES454934A patent/ES454934A1/es not_active Expired
- 1977-01-12 NL NL7700259A patent/NL7700259A/xx not_active Application Discontinuation
- 1977-01-14 IT IT19344/77A patent/IT1076221B/it active
- 1977-01-14 HU HU77HO1952A patent/HU176109B/hu unknown
- 1977-01-14 AU AU21342/77A patent/AU2134277A/en not_active Expired
- 1977-01-14 AT AT18977A patent/AT354440B/de not_active IP Right Cessation
- 1977-01-14 DK DK14877A patent/DK14877A/da unknown
- 1977-01-14 CA CA269,714A patent/CA1089472A/en not_active Expired
- 1977-01-14 NO NO770123A patent/NO770123L/no unknown
- 1977-01-14 US US05/759,546 patent/US4118501A/en not_active Expired - Lifetime
- 1977-01-14 IL IL51263A patent/IL51263A/xx unknown
- 1977-01-14 FI FI770109A patent/FI770109A7/fi not_active Application Discontinuation
- 1977-01-14 LU LU76579A patent/LU76579A1/xx unknown
- 1977-01-17 JP JP301777A patent/JPS5293742A/ja active Pending
- 1977-01-17 FR FR7701172A patent/FR2338269A1/fr active Granted
- 1977-01-17 GB GB1749/77A patent/GB1570912A/en not_active Expired
- 1977-01-17 BE BE174132A patent/BE850451A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2338269B1 (de) | 1981-01-09 |
| GB1570912A (en) | 1980-07-09 |
| IL51263A0 (en) | 1977-03-31 |
| JPS5293742A (en) | 1977-08-06 |
| FR2338269A1 (fr) | 1977-08-12 |
| IT1076221B (it) | 1985-04-27 |
| SE7700436L (sv) | 1977-07-18 |
| ES454934A1 (es) | 1977-12-16 |
| IL51263A (en) | 1979-10-31 |
| FI770109A7 (de) | 1977-07-18 |
| AT354440B (de) | 1979-01-10 |
| DK14877A (da) | 1977-07-18 |
| CA1089472A (en) | 1980-11-11 |
| BE850451A (fr) | 1977-07-18 |
| DE2601598A1 (de) | 1977-07-21 |
| ATA18977A (de) | 1979-06-15 |
| NL7700259A (nl) | 1977-07-19 |
| AU2134277A (en) | 1978-07-20 |
| LU76579A1 (de) | 1977-07-27 |
| HU176109B (en) | 1980-12-28 |
| US4118501A (en) | 1978-10-03 |
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