NO154132B - Analogifremgangsm¨te til fremstilling av terapeutisk aktiv e tiazolinderivater. - Google Patents

Analogifremgangsm¨te til fremstilling av terapeutisk aktiv e tiazolinderivater. Download PDF

Info

Publication number: NO154132B
Authority: NO; Norway
Prior art keywords: methyl; chloro; thiazoline; melting point; imino
Prior art date: 1979-07-03

Application number

NO801995A

Other languages

English (en)

Norwegian (no)

Other versions

NO801995L (no

Inventor

Hans-Joechen Lang

Bernhard Seuring

Ernold Granzer

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.)

1979-07-03

Filing date

1980-07-02

Publication date

1986-04-14

1980-07-02 Application filed by Hoechst Ag filed Critical Hoechst Ag

1981-01-05 Publication of NO801995L publication Critical patent/NO801995L/no

1986-04-14 Publication of NO154132B publication Critical patent/NO154132B/no

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 16
230000001225 therapeutic effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 110
239000002904 solvent Substances 0.000 claims description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 27
-1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
229910052794 bromium Inorganic materials 0.000 claims description 12
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
150000002431 hydrogen Chemical class 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
150000003549 thiazolines Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
238000012546 transfer Methods 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
150000007514 bases Chemical class 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
150000001718 carbodiimides Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
230000018044 dehydration Effects 0.000 claims description 3
238000006297 dehydration reaction Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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 2
230000008569 process Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
238000002844 melting Methods 0.000 description 274
230000008018 melting Effects 0.000 description 274
238000000354 decomposition reaction Methods 0.000 description 107
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 103
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
239000013078 crystal Substances 0.000 description 76
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
229960000583 acetic acid Drugs 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
239000012362 glacial acetic acid Substances 0.000 description 32
239000000203 mixture Substances 0.000 description 27
239000000243 solution Substances 0.000 description 27
238000009835 boiling Methods 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
235000002639 sodium chloride Nutrition 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 15
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 14
108090001030 Lipoproteins Proteins 0.000 description 13
102000004895 Lipoproteins Human genes 0.000 description 13
235000011054 acetic acid Nutrition 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
NRWBCTIORMNETF-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N(C)C)=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 NRWBCTIORMNETF-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
238000003756 stirring Methods 0.000 description 12
229960004592 isopropanol Drugs 0.000 description 11
238000010992 reflux Methods 0.000 description 11
210000002966 serum Anatomy 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
238000001914 filtration Methods 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
238000004821 distillation Methods 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
239000000725 suspension Substances 0.000 description 7
UUEZMFJKFJEZTG-UHFFFAOYSA-N 1,3-thiazolidin-4-ol Chemical class OC1CSCN1 UUEZMFJKFJEZTG-UHFFFAOYSA-N 0.000 description 6
IGEQFPWPMCIYDF-UHFFFAOYSA-N 1-methyl-3-phenylthiourea Chemical compound CNC(=S)NC1=CC=CC=C1 IGEQFPWPMCIYDF-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
108010007622 LDL Lipoproteins Proteins 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
150000003585 thioureas Chemical class 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
JPDYOZCIHZMCST-UHFFFAOYSA-N 2-chloro-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN1C(C=2C=C(C(Cl)=CC=2)S(N)(=O)=O)=CSC1=NC1=CC=CC=C1 JPDYOZCIHZMCST-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
230000033228 biological regulation Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
229960001214 clofibrate Drugs 0.000 description 4
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000003586 protic polar solvent Substances 0.000 description 4
230000007017 scission Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-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
238000011282 treatment Methods 0.000 description 4
239000000052 vinegar Substances 0.000 description 4
235000021419 vinegar Nutrition 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
DPKWPIBFCMBMBL-UHFFFAOYSA-N 2-chloro-5-[2-(2,4-dimethylphenyl)imino-3-methyl-1,3-thiazol-4-yl]-n,n-dimethylbenzenesulfonamide;hydrobromide Chemical compound Br.C1=C(Cl)C(S(=O)(=O)N(C)C)=CC(C=2N(C(=NC=3C(=CC(C)=CC=3)C)SC=2)C)=C1 DPKWPIBFCMBMBL-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000031226 Hyperlipidaemia Diseases 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
244000309464 bull Species 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
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239000002274 desiccant Substances 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
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239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
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229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000000565 sulfonamide group Chemical group 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 2
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UKOJOHPYEVWPNN-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC=C(Cl)C=C1 UKOJOHPYEVWPNN-UHFFFAOYSA-N 0.000 description 2
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VSHWTDHFQNOVJB-UHFFFAOYSA-N 2-chloro-5-(3-hexyl-2-phenylimino-1,3-thiazol-4-yl)-n,n-dimethylbenzenesulfonamide;hydrobromide Chemical compound Br.CCCCCCN1C(C=2C=C(C(Cl)=CC=2)S(=O)(=O)N(C)C)=CSC1=NC1=CC=CC=C1 VSHWTDHFQNOVJB-UHFFFAOYSA-N 0.000 description 2
QOXGKRGCYMLJDB-UHFFFAOYSA-N 2-chloro-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonyl chloride;hydrobromide Chemical compound Br.CN1C(C=2C=C(C(Cl)=CC=2)S(Cl)(=O)=O)=CSC1=NC1=CC=CC=C1 QOXGKRGCYMLJDB-UHFFFAOYSA-N 0.000 description 2
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IZGDNGFJPWGJGT-UHFFFAOYSA-N 2-chloro-5-[2-[4-(diethylamino)phenyl]imino-3-methyl-1,3-thiazol-4-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(N(CC)CC)=CC=C1N=C1N(C)C(C=2C=C(C(Cl)=CC=2)S(N)(=O)=O)=CS1 IZGDNGFJPWGJGT-UHFFFAOYSA-N 0.000 description 1
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KDVDJYKVQSFWFI-UHFFFAOYSA-N 2-chloro-5-[3-methyl-2-(3-methylphenyl)imino-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound CC1=CC=CC(N=C2N(C(C=3C=C(C(Cl)=CC=3)S(N)(=O)=O)=CS2)C)=C1 KDVDJYKVQSFWFI-UHFFFAOYSA-N 0.000 description 1
OLVQITFXMFSGIN-UHFFFAOYSA-N 2-chloro-5-[3-methyl-2-(4-methylphenyl)imino-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1N=C1N(C)C(C=2C=C(C(Cl)=CC=2)S(N)(=O)=O)=CS1 OLVQITFXMFSGIN-UHFFFAOYSA-N 0.000 description 1
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YUTGZQIVUPKPRQ-UHFFFAOYSA-N 2-chloro-5-[3-methyl-2-[3-(trifluoromethyl)phenyl]imino-1,3-thiazol-4-yl]benzenesulfonamide;hydrobromide Chemical compound Br.CN1C(C=2C=C(C(Cl)=CC=2)S(N)(=O)=O)=CSC1=NC1=CC=CC(C(F)(F)F)=C1 YUTGZQIVUPKPRQ-UHFFFAOYSA-N 0.000 description 1
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PIXCJWOQZWIMJS-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-5-[3-methyl-2-(3,4,5-trimethoxyphenyl)imino-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(N=C2N(C(C=3C=C(C(Cl)=CC=3)S(=O)(=O)N(C)C)=CS2)C)=C1 PIXCJWOQZWIMJS-UHFFFAOYSA-N 0.000 description 1
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OUNAICCPCIYVMW-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-5-[3-methyl-2-[3-(trifluoromethyl)phenyl]imino-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N(C)C)=CC(C=2N(C(=NC=3C=C(C=CC=3)C(F)(F)F)SC=2)C)=C1 OUNAICCPCIYVMW-UHFFFAOYSA-N 0.000 description 1
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RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical class SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
229960003602 guanethidine Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
WDJXDOCQCALXMV-UHFFFAOYSA-N hydron;1,3-thiazol-2-amine;chloride Chemical compound Cl.NC1=NC=CS1 WDJXDOCQCALXMV-UHFFFAOYSA-N 0.000 description 1
208000020346 hyperlipoproteinemia Diseases 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910001853 inorganic hydroxide Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
108010022197 lipoprotein cholesterol Proteins 0.000 description 1
239000007788 liquid Substances 0.000 description 1
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
DKDLLHXBXKPGJV-UHFFFAOYSA-N n'-methyl-n-phenylcarbamimidoyl chloride;hydrochloride Chemical compound Cl.CNC(Cl)=NC1=CC=CC=C1 DKDLLHXBXKPGJV-UHFFFAOYSA-N 0.000 description 1
UKRCZXBWQXSHNE-UHFFFAOYSA-N n,n,2-trimethyl-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)N(C)C)=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 UKRCZXBWQXSHNE-UHFFFAOYSA-N 0.000 description 1
VHFQKKXYWILWRI-UHFFFAOYSA-N n,n,2-trimethyl-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.C1=C(C)C(S(=O)(=O)N(C)C)=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 VHFQKKXYWILWRI-UHFFFAOYSA-N 0.000 description 1
ZAFXTBKXYPAUNX-UHFFFAOYSA-N n,n,3-trimethyl-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(C)=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 ZAFXTBKXYPAUNX-UHFFFAOYSA-N 0.000 description 1
FBEAVCBCCOZLSO-UHFFFAOYSA-N n,n,3-trimethyl-5-[3-methyl-2-(4-propan-2-ylphenyl)imino-1,3-thiazol-4-yl]benzenesulfonamide;hydrobromide Chemical compound Br.C1=CC(C(C)C)=CC=C1N=C1N(C)C(C=2C=C(C=C(C)C=2)S(=O)(=O)N(C)C)=CS1 FBEAVCBCCOZLSO-UHFFFAOYSA-N 0.000 description 1
YSOPACAXEPDTRZ-UHFFFAOYSA-N n,n,4-trimethyl-3-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C)C(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 YSOPACAXEPDTRZ-UHFFFAOYSA-N 0.000 description 1
ITPDKYNTXNFIGO-UHFFFAOYSA-N n,n,4-trimethyl-3-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CN(C)S(=O)(=O)C1=CC=C(C)C(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 ITPDKYNTXNFIGO-UHFFFAOYSA-N 0.000 description 1
SRJHYEQAMXDMEP-UHFFFAOYSA-N n,n-dimethyl-3-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 SRJHYEQAMXDMEP-UHFFFAOYSA-N 0.000 description 1
OWPSMGSPLQPYSB-UHFFFAOYSA-N n,n-dimethyl-3-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide;hydrobromide Chemical compound Br.CN(C)S(=O)(=O)C1=CC=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 OWPSMGSPLQPYSB-UHFFFAOYSA-N 0.000 description 1
DSDGWZDFIKLWNE-UHFFFAOYSA-N n-butyl-2-chloro-5-(3-methyl-2-phenylimino-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)NCCCC)=CC(C=2N(C(=NC=3C=CC=CC=3)SC=2)C)=C1 DSDGWZDFIKLWNE-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
RLEKTPHUQPAOAF-UHFFFAOYSA-N n-methyl-n'-phenylmethanediimine Chemical compound CN=C=NC1=CC=CC=C1 RLEKTPHUQPAOAF-UHFFFAOYSA-N 0.000 description 1
CPGWSLFYXMRNDV-UHFFFAOYSA-N n-methyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1 CPGWSLFYXMRNDV-UHFFFAOYSA-N 0.000 description 1
QANXVLRELWRTKI-UHFFFAOYSA-N n-phenyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1NC1=NC=CS1 QANXVLRELWRTKI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940127017 oral antidiabetic Drugs 0.000 description 1
239000003538 oral antidiabetic agent Substances 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000009993 protective function Effects 0.000 description 1
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
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
SLASUBUREDJDLK-UHFFFAOYSA-N s-[2-[2-chloro-5-(dimethylsulfamoyl)phenyl]-2-oxoethyl] ethanethioate Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C(C(=O)CSC(C)=O)=C1 SLASUBUREDJDLK-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000000054 salidiuretic effect Effects 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/66—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to halogen atoms or to nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/36—Isothioureas having sulfur atoms of isothiourea groups bound to carbon atoms of six-membered aromatic rings
- 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
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO801995A 1979-07-03 1980-07-02 Analogifremgangsm¨te til fremstilling av terapeutisk aktiv e tiazolinderivater. NO154132B (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792926771 DE2926771A1 (de)	1979-07-03	1979-07-03	Thiazolidinderivate und verfahren zu ihrer herstellung

Publications (2)

Publication Number	Publication Date
NO801995L NO801995L (no)	1981-01-05
NO154132B true NO154132B (no)	1986-04-14

Family

ID=6074772

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO801995A NO154132B (no)	1979-07-03	1980-07-02	Analogifremgangsm¨te til fremstilling av terapeutisk aktiv e tiazolinderivater.
NO844120A NO844120L (no)	1979-07-03	1984-10-16	Tiazolinderivater og fremgangsmaate for dets fremstilling

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO844120A NO844120L (no)	1979-07-03	1984-10-16	Tiazolinderivater og fremgangsmaate for dets fremstilling

Country Status (16)

Country	Link
US (1)	US4346088A (es)
EP (1)	EP0023964B1 (es)
JP (1)	JPS5610180A (es)
AR (3)	AR229875A1 (es)
AT (1)	ATE2524T1 (es)
AU (1)	AU533589B2 (es)
CA (1)	CA1156240A (es)
DE (2)	DE2926771A1 (es)
DK (1)	DK286580A (es)
EG (1)	EG14763A (es)
ES (5)	ES492847A0 (es)
FI (1)	FI802094A (es)
HU (1)	HU182164B (es)
IL (1)	IL60468A (es)
NO (2)	NO154132B (es)
ZA (1)	ZA803979B (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
HU195492B (en) *	1984-07-27	1988-05-30	Boehringer Biochemia Srl	Process for producing 2-substituted thiazolidine derivatives with antitussive and mucus regulating action and pharmaceuticals comprising these compounds as active ingredient
US5866595A (en) *	1991-09-26	1999-02-02	The Regents Of The University Of California	Calcium antagonists for treatment of vascular restenosis
CA2195847A1 (en) *	1994-07-27	1996-02-08	John J. Talley	Substituted thiazoles for the treatment of inflammation
IL144031A0 (en) *	1999-01-14	2002-04-21	Bayer Ag	Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
US6353006B1 (en)	1999-01-14	2002-03-05	Bayer Corporation	Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
FR2819508B1 (fr) *	2001-01-12	2005-01-21	Sod Conseils Rech Applic	Derives de 2-arylimino-2, 3-dihydorthiazoles, leurs procedes de preparation et leur utilisation therapeutiques
FR2796643B1 (fr) *	1999-07-22	2005-04-29	Sod Conseils Rech Applic	Derives de 2-arylimino-2, 3-dihydrothiazoles, leurs procedes de preparation et leur utilisation therapeutique
ATE393150T1 (de) *	1999-09-14	2008-05-15	Shionogi & Co	2-imino-1,3-thiazin-derivate

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2436263C2 (de) *	1974-07-27	1983-02-17	Hoechst Ag, 6000 Frankfurt	Thiazolidinderivate und Verfahren zu ihrer Herstellung
DE2533821A1 (de) *	1975-07-29	1977-02-17	Hoechst Ag	Thiazolidinderivate und verfahren zu ihrer herstellung
DE2546165A1 (de) *	1975-10-15	1977-04-28	Hoechst Ag	Thiazolidinderivate und verfahren zu ihrer herstellung
SE7700436L (sv) *	1976-01-17	1977-07-18	Hoechst Ag	Tiazolidinderivat och forfarande for deras framstellning

1979
- 1979-07-03 DE DE19792926771 patent/DE2926771A1/de not_active Withdrawn
1980
- 1980-06-27 ES ES492847A patent/ES492847A0/es active Granted
- 1980-06-27 ES ES492871A patent/ES8103066A1/es not_active Expired
- 1980-06-27 ES ES492872A patent/ES8103067A1/es not_active Expired
- 1980-06-27 ES ES492873A patent/ES492873A0/es active Granted
- 1980-06-27 ES ES492874A patent/ES8103069A1/es not_active Expired
- 1980-06-28 EP EP80103688A patent/EP0023964B1/de not_active Expired
- 1980-06-28 AT AT80103688T patent/ATE2524T1/de not_active IP Right Cessation
- 1980-06-28 DE DE8080103688T patent/DE3062017D1/de not_active Expired
- 1980-07-01 US US06/165,218 patent/US4346088A/en not_active Expired - Lifetime
- 1980-07-01 FI FI802094A patent/FI802094A/fi not_active Application Discontinuation
- 1980-07-01 AR AR281607A patent/AR229875A1/es active
- 1980-07-02 EG EG395/80A patent/EG14763A/xx active
- 1980-07-02 IL IL60468A patent/IL60468A/xx unknown
- 1980-07-02 NO NO801995A patent/NO154132B/no unknown
- 1980-07-02 AU AU60037/80A patent/AU533589B2/en not_active Ceased
- 1980-07-02 DK DK286580A patent/DK286580A/da not_active Application Discontinuation
- 1980-07-02 CA CA000355222A patent/CA1156240A/en not_active Expired
- 1980-07-02 ZA ZA00803979A patent/ZA803979B/xx unknown
- 1980-07-02 HU HU801643A patent/HU182164B/hu unknown
- 1980-07-03 JP JP9160580A patent/JPS5610180A/ja active Pending
1981
- 1981-07-31 AR AR286306A patent/AR229876A1/es active
- 1981-07-31 AR AR286305A patent/AR226119A1/es active
1984
- 1984-10-16 NO NO844120A patent/NO844120L/no unknown

Also Published As

Publication number	Publication date
ZA803979B (en)	1981-06-24
ES492872A0 (es)	1981-02-16
CA1156240A (en)	1983-11-01
EG14763A (en)	1986-09-30
ATE2524T1 (de)	1983-03-15
IL60468A (en)	1984-11-30
DE3062017D1 (en)	1983-03-24
DK286580A (da)	1981-01-04
ES8103068A1 (es)	1981-02-16
AR229875A1 (es)	1983-12-30
ES492874A0 (es)	1981-02-16
AR226119A1 (es)	1982-05-31
ES492873A0 (es)	1981-02-16
DE2926771A1 (de)	1981-01-15
EP0023964A1 (de)	1981-02-18
NO844120L (no)	1981-01-05
JPS5610180A (en)	1981-02-02
FI802094A (fi)	1981-01-04
AU533589B2 (en)	1983-12-01
AU6003780A (en)	1981-01-15
ES492871A0 (es)	1981-02-16
US4346088A (en)	1982-08-24
EP0023964B1 (de)	1983-02-16
ES8103066A1 (es)	1981-02-16
ES8103065A1 (es)	1981-02-16
ES8103069A1 (es)	1981-02-16
IL60468A0 (en)	1980-09-16
ES492847A0 (es)	1981-02-16
NO801995L (no)	1981-01-05
HU182164B (en)	1983-12-28
ES8103067A1 (es)	1981-02-16
AR229876A1 (es)	1983-12-30

Publication	Publication Date	Title
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SU1099843A3 (ru)	1984-06-23	Способ получени производных 5-замещенного оксазолидин-2,4-диона или их фармацевтически приемлемых солей
NO812558L (no)	1982-01-29	Fremgangsmaate for fremstilling av terapeutisk aktive oksazolidin-derivater.
NO157896B (no)	1988-02-29	Analogifremgangsmaate for fremstilling av terapeutisk virksomme tiazolidindion-derivater.
CA2669069A1 (en)	2008-05-29	Process for the preparation of 2-imino-thiazolidin-4-one derivatives
KR101701531B1 (ko)	2017-02-01	벤조티아진 유도체, 이의 제조방법 및 약물로서의 용도
IE920734A1 (en)	1992-10-07	4-aryl-thiazole or imidazole derivatives
NO154132B (no)	1986-04-14	Analogifremgangsm¨te til fremstilling av terapeutisk aktiv e tiazolinderivater.
AU599014B2 (en)	1990-07-12	5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics
EP0398179B1 (en)	1996-01-17	Rhodanine derivatives and pharmaceutical compositions
US4421757A (en)	1983-12-20	Thiazoline derivatives, processes for their preparation, their use and pharmaceutical preparations based on these compounds
Miller et al.	1957	By-products of the Willgerodt Reaction Applied to α-and γ-Picoline
Tarbell et al.	1950	2-Methyl-5-ethoxythiazole and Related Compounds1
US2858318A (en)	1958-10-28	p-substituted benzene sulphonamides
CZ304804B6 (cs)	2014-11-05	Způsob přípravy derivátu thiazolu
HU198915B (en)	1989-12-28	Process for producing new 2-thiazolidinone derivatives and pharmaceutical compositions containing them
US4118501A (en)	1978-10-03	Thiazolidine derivatives
KR850000757B1 (ko)	1985-05-25	티아졸린 유도체의 제조방법
JP3190959B2 (ja)	2001-07-23	４−メチル−５−（２−クロロエチル）−チアゾールおよびその同族体の新規な製法
US4156735A (en)	1979-05-29	Thiazolidine derivatives
NO131345B (es)	1975-02-03
US4002620A (en)	1977-01-11	2-Anilino-4H-3,1-benzothiazines
RU2103264C1 (ru)	1998-01-27	Способ получения производных тиазола или их солей присоединения кислот, 5-хлор-3-тиоцианато-2-алканон и способ его получения
DD223450A5 (de)	1985-06-12	Verfahren zur herstellung von benzofuranonen
IE922238A1 (en)	1993-01-13	Process for the preparation of the dextrorotatory isomer of an isoindolinone derivative