GB1579147A - Fatty acid derivatives - Google Patents
Fatty acid derivatives Download PDFInfo
- Publication number
- GB1579147A GB1579147A GB20909/77A GB2090977A GB1579147A GB 1579147 A GB1579147 A GB 1579147A GB 20909/77 A GB20909/77 A GB 20909/77A GB 2090977 A GB2090977 A GB 2090977A GB 1579147 A GB1579147 A GB 1579147A
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- United Kingdom
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- 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.)
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- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 title claims description 15
- -1 thiocarbamoylthio Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- JAUVJUIRMBVEBK-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCC1=CC=C(Cl)C=C1 JAUVJUIRMBVEBK-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 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 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 239000000243 solution Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- ZHKHEKQXPVAWBQ-UHFFFAOYSA-N azanium N-[(4-chlorophenyl)methyl]carbamodithioate Chemical compound ClC1=CC=C(CNC([S-])=S)C=C1.[NH4+] ZHKHEKQXPVAWBQ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- TUSQROPXOFNEJF-UHFFFAOYSA-N 4-[(4-chlorophenyl)methylcarbamothioylsulfanyl]butanoic acid Chemical compound OC(=O)CCCSC(=S)NCC1=CC=C(Cl)C=C1 TUSQROPXOFNEJF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- CNFVZWRCQAKEMX-UHFFFAOYSA-N 3-cyanopropyl n-[(4-chlorophenyl)methyl]carbamodithioate Chemical compound ClC1=CC=C(CNC(=S)SCCCC#N)C=C1 CNFVZWRCQAKEMX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VULJRWWTYDNKAG-UHFFFAOYSA-N (4-amino-4-oxobutyl) N-[(4-chlorophenyl)methyl]carbamodithioate Chemical compound C(N)(=O)CCCSC(NCC1=CC=C(C=C1)Cl)=S VULJRWWTYDNKAG-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- PKVMDUCEFGCWJZ-UHFFFAOYSA-N (4-chlorophenyl)methyl-(4-morpholin-4-yl-4-oxobutyl)carbamodithioic acid Chemical compound C=1C=C(Cl)C=CC=1CN(C(=S)S)CCCC(=O)N1CCOCC1 PKVMDUCEFGCWJZ-UHFFFAOYSA-N 0.000 description 1
- GCHMZPCRMFIHLH-UHFFFAOYSA-N (4-chlorophenyl)methyl-(4-oxo-4-piperidin-1-ylbutyl)carbamodithioic acid Chemical compound C=1C=C(Cl)C=CC=1CN(C(=S)S)CCCC(=O)N1CCCCC1 GCHMZPCRMFIHLH-UHFFFAOYSA-N 0.000 description 1
- XZNUYNGMSDOFLW-UHFFFAOYSA-N (4-chlorophenyl)methyl-[4-(diethylamino)-4-oxobutyl]carbamodithioic acid Chemical compound CCN(CC)C(=O)CCCN(C(S)=S)CC1=CC=C(Cl)C=C1 XZNUYNGMSDOFLW-UHFFFAOYSA-N 0.000 description 1
- PPFAZYKSIYAIQL-UHFFFAOYSA-N (4-chlorophenyl)methyl-[4-(ethylamino)-4-oxobutyl]carbamodithioic acid Chemical compound CCNC(=O)CCCN(CC1=CC=C(C=C1)Cl)C(=S)S PPFAZYKSIYAIQL-UHFFFAOYSA-N 0.000 description 1
- XVKYCAOXHSIHPG-UHFFFAOYSA-N (4-chlorophenyl)methyl-[4-(methylamino)-4-oxobutyl]carbamodithioic acid Chemical compound CNC(=O)CCCN(C(S)=S)CC1=CC=C(Cl)C=C1 XVKYCAOXHSIHPG-UHFFFAOYSA-N 0.000 description 1
- DEHXIHUIYSXZNH-UHFFFAOYSA-N 1-chloro-4-(isothiocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=S)C=C1 DEHXIHUIYSXZNH-UHFFFAOYSA-N 0.000 description 1
- UPYCHMKZLRWGBG-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylcarbamothioylsulfanyl]propanoic acid Chemical compound OC(=O)CCSC(=S)NCC1=CC=C(Cl)C=C1 UPYCHMKZLRWGBG-UHFFFAOYSA-N 0.000 description 1
- GLJSIFNKOLIVMV-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)ethylcarbamothioylsulfanyl]propanoic acid Chemical compound OC(=O)CCSC(=S)NCCC1=CC=C(Cl)C=C1 GLJSIFNKOLIVMV-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- JFKGUZCYBXRNMR-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)ethylcarbamothioylsulfanyl]butanoic acid Chemical compound OC(=O)CCCSC(=S)NCCC1=CC=C(Cl)C=C1 JFKGUZCYBXRNMR-UHFFFAOYSA-N 0.000 description 1
- LDRZQWWWPRDBRJ-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)propylcarbamothioylsulfanyl]butanoic acid Chemical compound OC(=O)CCCSC(=S)NCCCC1=CC=C(Cl)C=C1 LDRZQWWWPRDBRJ-UHFFFAOYSA-N 0.000 description 1
- CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 241000700159 Rattus Species 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- AOEYPFMZEUTARK-UHFFFAOYSA-N butyl 4-[(4-chlorophenyl)methylcarbamothioylsulfanyl]butanoate Chemical compound CCCCOC(=O)CCCSC(=S)NCC1=CC=C(Cl)C=C1 AOEYPFMZEUTARK-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
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- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZRVXMUFCSGUOCJ-UHFFFAOYSA-N ethyl 11-[(4-chlorophenyl)methylcarbamothioylsulfanyl]undecanoate Chemical compound CCOC(=O)CCCCCCCCCCSC(=S)NCC1=CC=C(Cl)C=C1 ZRVXMUFCSGUOCJ-UHFFFAOYSA-N 0.000 description 1
- OJPQERVTSVWKPM-UHFFFAOYSA-N ethyl 3-[(4-chlorophenyl)methylcarbamothioylsulfanyl]propanoate Chemical compound CCOC(=O)CCSC(=S)NCC1=CC=C(Cl)C=C1 OJPQERVTSVWKPM-UHFFFAOYSA-N 0.000 description 1
- QERXOHRLMFRKHT-UHFFFAOYSA-N ethyl 4-[(2,5-dichlorophenyl)methylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCC1=CC(Cl)=CC=C1Cl QERXOHRLMFRKHT-UHFFFAOYSA-N 0.000 description 1
- USZBJBHKTQULRV-UHFFFAOYSA-N ethyl 4-[(4-methoxyphenyl)methylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCC1=CC=C(OC)C=C1 USZBJBHKTQULRV-UHFFFAOYSA-N 0.000 description 1
- DYBSXZSFKNLAHI-UHFFFAOYSA-N ethyl 4-[(4-methylphenyl)methylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCC1=CC=C(C)C=C1 DYBSXZSFKNLAHI-UHFFFAOYSA-N 0.000 description 1
- KZGBQIIUMCICJQ-UHFFFAOYSA-N ethyl 4-[2-(4-chlorophenyl)ethylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCCC1=CC=C(Cl)C=C1 KZGBQIIUMCICJQ-UHFFFAOYSA-N 0.000 description 1
- UYRFDYMCXZFXHX-UHFFFAOYSA-N ethyl 4-[3-(4-chlorophenyl)propylcarbamothioylsulfanyl]butanoate Chemical compound CCOC(=O)CCCSC(=S)NCCCC1=CC=C(Cl)C=C1 UYRFDYMCXZFXHX-UHFFFAOYSA-N 0.000 description 1
- KKTZCTVQMWPWDP-UHFFFAOYSA-N ethyl 5-[(4-chlorophenyl)methylcarbamothioylsulfanyl]pentanoate Chemical compound CCOC(=O)CCCCSC(=S)NCC1=CC=C(Cl)C=C1 KKTZCTVQMWPWDP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT365476A AT346359B (de) | 1976-05-19 | 1976-05-19 | Verfahren zur herstellung von neuen dithiocarbaminsaeureestern |
| CH272377 | 1977-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1579147A true GB1579147A (en) | 1980-11-12 |
Family
ID=25600288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20909/77A Expired GB1579147A (en) | 1976-05-19 | 1977-05-18 | Fatty acid derivatives |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS52142043A (enExample) |
| AU (1) | AU508876B2 (enExample) |
| CA (1) | CA1077938A (enExample) |
| DE (1) | DE2721762A1 (enExample) |
| DK (1) | DK219877A (enExample) |
| ES (1) | ES464322A1 (enExample) |
| FI (1) | FI771598A7 (enExample) |
| FR (1) | FR2368472A1 (enExample) |
| GB (1) | GB1579147A (enExample) |
| GR (1) | GR74111B (enExample) |
| HU (1) | HU173336B (enExample) |
| IL (1) | IL52071A0 (enExample) |
| IT (1) | IT1076893B (enExample) |
| LU (1) | LU77356A1 (enExample) |
| MC (1) | MC1144A1 (enExample) |
| NL (1) | NL7704216A (enExample) |
| NO (1) | NO771755L (enExample) |
| NZ (1) | NZ184089A (enExample) |
| PT (1) | PT66564B (enExample) |
| SE (1) | SE7705933L (enExample) |
-
1977
- 1977-04-18 NL NL7704216A patent/NL7704216A/xx not_active Application Discontinuation
- 1977-04-29 IT IT7723061A patent/IT1076893B/it active
- 1977-05-11 CA CA278,177A patent/CA1077938A/en not_active Expired
- 1977-05-12 IL IL52071A patent/IL52071A0/xx unknown
- 1977-05-13 AU AU25139/77A patent/AU508876B2/en not_active Expired
- 1977-05-13 DE DE19772721762 patent/DE2721762A1/de not_active Withdrawn
- 1977-05-13 NZ NZ184089A patent/NZ184089A/xx unknown
- 1977-05-16 JP JP5627777A patent/JPS52142043A/ja active Pending
- 1977-05-17 LU LU77356A patent/LU77356A1/xx unknown
- 1977-05-17 GR GR53488A patent/GR74111B/el unknown
- 1977-05-17 FR FR7715066A patent/FR2368472A1/fr active Pending
- 1977-05-17 HU HU77HO1984A patent/HU173336B/hu unknown
- 1977-05-18 SE SE7705933A patent/SE7705933L/xx unknown
- 1977-05-18 DK DK219877A patent/DK219877A/da not_active Application Discontinuation
- 1977-05-18 GB GB20909/77A patent/GB1579147A/en not_active Expired
- 1977-05-18 PT PT66564A patent/PT66564B/pt unknown
- 1977-05-18 NO NO771755A patent/NO771755L/no unknown
- 1977-05-18 MC MC771243A patent/MC1144A1/fr unknown
- 1977-05-19 FI FI771598A patent/FI771598A7/fi not_active Application Discontinuation
- 1977-11-21 ES ES77464322A patent/ES464322A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| MC1144A1 (fr) | 1978-01-30 |
| PT66564A (en) | 1977-06-01 |
| AU508876B2 (en) | 1980-04-03 |
| PT66564B (en) | 1979-04-13 |
| IT1076893B (it) | 1985-04-27 |
| NL7704216A (nl) | 1977-11-22 |
| LU77356A1 (enExample) | 1978-06-26 |
| FR2368472A1 (fr) | 1978-05-19 |
| CA1077938A (en) | 1980-05-20 |
| FI771598A7 (enExample) | 1977-11-20 |
| GR74111B (enExample) | 1984-06-06 |
| JPS52142043A (en) | 1977-11-26 |
| NZ184089A (en) | 1980-05-27 |
| DK219877A (da) | 1977-11-20 |
| DE2721762A1 (de) | 1977-12-01 |
| HU173336B (hu) | 1979-04-28 |
| AU2513977A (en) | 1978-11-16 |
| ES464322A1 (es) | 1978-12-16 |
| NO771755L (no) | 1977-11-22 |
| SE7705933L (sv) | 1977-11-20 |
| IL52071A0 (en) | 1977-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |