CH632487A5 - Process for preparing novel cyanoacetanilide derivatives - Google Patents

Process for preparing novel cyanoacetanilide derivatives Download PDF

Info

Publication number: CH632487A5
Authority: CH; Switzerland
Prior art keywords: formula; group; anilide; cyanoacetic; methyl
Prior art date: 1975-12-11

Application number

CH1560476A

Other languages

German (de)

English (en)

Inventor

Klaus-Dieter Dr Kampe

Hartmut Dr Ertel

Guenther Dr Heubach

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.)

1975-12-11

Filing date

1976-12-10

Publication date

1982-10-15

1975-12-11 Priority claimed from DE19752555685 external-priority patent/DE2555685A1/de

1975-12-18 Priority claimed from DE19752557003 external-priority patent/DE2557003A1/de

1976-12-10 Application filed by Hoechst Ag filed Critical Hoechst Ag

1982-10-15 Publication of CH632487A5 publication Critical patent/CH632487A5/de

Links

XCTQPMCULSZKLT-UHFFFAOYSA-N 2-cyano-n-phenylacetamide Chemical class N#CCC(=O)NC1=CC=CC=C1 XCTQPMCULSZKLT-UHFFFAOYSA-N 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 21
239000002253 acid Substances 0.000 claims abstract description 7
150000008064 anhydrides Chemical class 0.000 claims abstract description 5
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 5
239000000194 fatty acid Substances 0.000 claims abstract description 5
229930195729 fatty acid Natural products 0.000 claims abstract description 5
150000004665 fatty acids Chemical class 0.000 claims abstract description 5
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 26
-1 ethyl mercapto group Chemical group 0.000 claims description 24
150000003931 anilides Chemical class 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 8
229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
125000000217 alkyl 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
IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 claims 1
150000002168 ethanoic acid esters Chemical class 0.000 claims 1
MAYUCBCSAVDUKG-UHFFFAOYSA-N orthoacetic acid Chemical compound CC(O)(O)O MAYUCBCSAVDUKG-UHFFFAOYSA-N 0.000 claims 1
230000007062 hydrolysis Effects 0.000 abstract description 14
238000006460 hydrolysis reaction Methods 0.000 abstract description 14
GLPCMJHDPXSCPC-UHFFFAOYSA-N 2-cyano-4-hydroxy-n-phenylbut-2-enamide Chemical class OCC=C(C#N)C(=O)NC1=CC=CC=C1 GLPCMJHDPXSCPC-UHFFFAOYSA-N 0.000 abstract description 9
239000003513 alkali Substances 0.000 abstract description 7
230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 6
230000000202 analgesic effect Effects 0.000 abstract description 4
125000001424 substituent group Chemical group 0.000 abstract description 3
230000000507 anthelmentic effect Effects 0.000 abstract description 2
230000000855 fungicidal effect Effects 0.000 abstract description 2
230000001857 anti-mycotic effect Effects 0.000 abstract 1
239000002543 antimycotic Substances 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 28
239000000203 mixture Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
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 13
239000000243 solution Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000011734 sodium Substances 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
229910052749 magnesium Inorganic materials 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000460 chlorine Chemical group 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229940091250 magnesium supplement Drugs 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
UXAGBBWETXVJBA-UHFFFAOYSA-N 2-cyano-4-hydroxy-N-[3-(trifluoromethyl)phenyl]but-2-enamide Chemical compound FC(C=1C=C(NC(C(C#N)=CCO)=O)C=CC=1)(F)F UXAGBBWETXVJBA-UHFFFAOYSA-N 0.000 description 5
VUKAKLFIJIBEBH-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC=CC(=C1)C(F)(F)F Chemical compound CCOCC=C(C#N)C(=O)NC1=CC=CC(=C1)C(F)(F)F VUKAKLFIJIBEBH-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000011591 potassium Substances 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000011592 zinc chloride Substances 0.000 description 5
235000005074 zinc chloride Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
JHGKLDZJAHYJIP-UHFFFAOYSA-N n-(3-chlorophenyl)-2-cyanoacetamide Chemical compound ClC1=CC=CC(NC(=O)CC#N)=C1 JHGKLDZJAHYJIP-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000002243 precursor Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
YWJVUOTVKRDVPF-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)Cl Chemical compound CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)Cl YWJVUOTVKRDVPF-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GSQPDTMXQHEJRH-UHFFFAOYSA-N N-(3-chlorophenyl)-2-cyano-4-hydroxybut-2-enamide Chemical compound ClC=1C=C(C=CC1)NC(C(C#N)=CCO)=O GSQPDTMXQHEJRH-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
150000002084 enol ethers Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
MAYSCNQPWLYWGT-UHFFFAOYSA-N 2-cyano-4-(4-methylpiperazin-1-yl)-N-[3-(trifluoromethyl)phenyl]but-2-enamide Chemical compound FC(C=1C=C(NC(C(C#N)=CCN2CCN(CC2)C)=O)C=CC1)(F)F MAYSCNQPWLYWGT-UHFFFAOYSA-N 0.000 description 2
ORLZOZCULIRPFA-UHFFFAOYSA-N 2-cyano-4-hydroxybut-2-enoic acid Chemical compound OCC=C(C#N)C(O)=O ORLZOZCULIRPFA-UHFFFAOYSA-N 0.000 description 2
HXXDPDIVNQZPCJ-UHFFFAOYSA-N 2-cyano-n-(3,4-dichlorophenyl)acetamide Chemical compound ClC1=CC=C(NC(=O)CC#N)C=C1Cl HXXDPDIVNQZPCJ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
DFPGMWQFUCNAJN-UHFFFAOYSA-N BrC=1C=C(NC(C(C#N)=CCO)=O)C=CC1 Chemical compound BrC=1C=C(NC(C(C#N)=CCO)=O)C=CC1 DFPGMWQFUCNAJN-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
UBSQJHALKXXISW-UHFFFAOYSA-N C1CCN(CC1)CC=C(C#N)C(=O)NC2=CC(=CC=C2)Cl Chemical compound C1CCN(CC1)CC=C(C#N)C(=O)NC2=CC(=CC=C2)Cl UBSQJHALKXXISW-UHFFFAOYSA-N 0.000 description 2
MIBGUKNVVFOLGQ-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=C(C=CC(=C1)Cl)C Chemical compound CCOCC=C(C#N)C(=O)NC1=C(C=CC(=C1)Cl)C MIBGUKNVVFOLGQ-UHFFFAOYSA-N 0.000 description 2
BJZQUFYGVDWWNI-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC(=C(C=C1)Cl)Cl Chemical compound CCOCC=C(C#N)C(=O)NC1=CC(=C(C=C1)Cl)Cl BJZQUFYGVDWWNI-UHFFFAOYSA-N 0.000 description 2
FDNFLWJBCGCNRB-UHFFFAOYSA-N CN(C)CC=C(C#N)C(=O)NC1=CC=CC(=C1)C(F)(F)F Chemical compound CN(C)CC=C(C#N)C(=O)NC1=CC=CC(=C1)C(F)(F)F FDNFLWJBCGCNRB-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
WTAWWICNIPRYJS-UHFFFAOYSA-N ClC=1C=C(NC(C(C#N)=CCO)=O)C=CC=1Cl Chemical compound ClC=1C=C(NC(C(C#N)=CCO)=O)C=CC=1Cl WTAWWICNIPRYJS-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
230000001760 anti-analgesic effect Effects 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
229950011008 tetrachloroethylene Drugs 0.000 description 2
239000011701 zinc Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
UKNCUROCOZYRNI-UHFFFAOYSA-N 2-cyano-4-(dimethylamino)but-2-enoic acid Chemical compound CN(C)CC=C(C(=O)O)C#N UKNCUROCOZYRNI-UHFFFAOYSA-N 0.000 description 1
HYPXSLNQQNLJDY-UHFFFAOYSA-N 2-cyano-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)CC#N)=C1 HYPXSLNQQNLJDY-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
NIRCAUPPZAUKDX-UHFFFAOYSA-N 5-benzyl-2-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-6-methylpyridazin-3-one Chemical compound O=C1C=C(CC=2C=CC=CC=2)C(C)=NN1CN(CC1)CCN1C1=CC=CC(Cl)=C1 NIRCAUPPZAUKDX-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
KTIKFVYBBYUEEB-UHFFFAOYSA-N BrC=1C=C(NC(C(C#N)=CCN(C)C)=O)C=CC1 Chemical compound BrC=1C=C(NC(C(C#N)=CCN(C)C)=O)C=CC1 KTIKFVYBBYUEEB-UHFFFAOYSA-N 0.000 description 1
WPHIEBMCBXBJOY-UHFFFAOYSA-N CC(C=CC(Cl)=C1)=C1NC(C(C#N)=CCN(C)C)=O Chemical compound CC(C=CC(Cl)=C1)=C1NC(C(C#N)=CCN(C)C)=O WPHIEBMCBXBJOY-UHFFFAOYSA-N 0.000 description 1
ZCOMHBIIMHDTAE-UHFFFAOYSA-N CC(C=CC(Cl)=C1)=C1NC(C(C#N)=CCO)=O Chemical compound CC(C=CC(Cl)=C1)=C1NC(C(C#N)=CCO)=O ZCOMHBIIMHDTAE-UHFFFAOYSA-N 0.000 description 1
QSDGSGSQAIIBGS-UHFFFAOYSA-N CC1=C(C=CC=C1Cl)NC(=O)C(=CCN(C)C)C#N Chemical compound CC1=C(C=CC=C1Cl)NC(=O)C(=CCN(C)C)C#N QSDGSGSQAIIBGS-UHFFFAOYSA-N 0.000 description 1
BBODSZUZCNNUPQ-UHFFFAOYSA-N CC1=C(C=CC=C1Cl)NC(=O)C(=CCO)C#N Chemical compound CC1=C(C=CC=C1Cl)NC(=O)C(=CCO)C#N BBODSZUZCNNUPQ-UHFFFAOYSA-N 0.000 description 1
FYIVPIMEGXQYSY-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)Br Chemical compound CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)Br FYIVPIMEGXQYSY-UHFFFAOYSA-N 0.000 description 1
DSSPSPIPOFUDBK-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)OC(C(F)Cl)(F)F Chemical compound CCOCC=C(C#N)C(=O)NC1=CC(=CC=C1)OC(C(F)Cl)(F)F DSSPSPIPOFUDBK-UHFFFAOYSA-N 0.000 description 1
AHVQDJALMVGBTM-UHFFFAOYSA-N CCOCC=C(C#N)C(=O)NC1=CC=C(C=C1)OC Chemical compound CCOCC=C(C#N)C(=O)NC1=CC=C(C=C1)OC AHVQDJALMVGBTM-UHFFFAOYSA-N 0.000 description 1
UOUXWFSZDSZVMB-UHFFFAOYSA-N CCOCC=C(C(NC1=C(C)C(Cl)=CC=C1)=O)C#N Chemical compound CCOCC=C(C(NC1=C(C)C(Cl)=CC=C1)=O)C#N UOUXWFSZDSZVMB-UHFFFAOYSA-N 0.000 description 1
LZFNVKAEQPGFAF-UHFFFAOYSA-N COC1=CC=C(C=C1)NC(=O)C(=CCO)C#N Chemical compound COC1=CC=C(C=C1)NC(=O)C(=CCO)C#N LZFNVKAEQPGFAF-UHFFFAOYSA-N 0.000 description 1
CPTNBMJZPCBPCA-UHFFFAOYSA-N COCC=C(C#N)C(=O)NC1=CC(=CC=C1)Cl Chemical compound COCC=C(C#N)C(=O)NC1=CC(=CC=C1)Cl CPTNBMJZPCBPCA-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VNLKZJBGJKCGAD-UHFFFAOYSA-N ClC=1C=C(NC(C(C#N)=CCN(C)C)=O)C=CC1 Chemical compound ClC=1C=C(NC(C(C#N)=CCN(C)C)=O)C=CC1 VNLKZJBGJKCGAD-UHFFFAOYSA-N 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
LEDHCSRRPOIEGC-UHFFFAOYSA-N NC1CCCCC1.N#CC(C(NC1=CC(C(F)(F)F)=CC=C1)=O)=CCO Chemical compound NC1CCCCC1.N#CC(C(NC1=CC(C(F)(F)F)=CC=C1)=O)=CCO LEDHCSRRPOIEGC-UHFFFAOYSA-N 0.000 description 1
229910019213 POCl3 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
PDWVXNLUDMQFCH-UHFFFAOYSA-N oxoantimony;hydrochloride Chemical compound Cl.[Sb]=O PDWVXNLUDMQFCH-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 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
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1560476A 1975-12-11 1976-12-10 Process for preparing novel cyanoacetanilide derivatives CH632487A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19752555685 DE2555685A1 (de)	1975-12-11	1975-12-11	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
DE19752557003 DE2557003A1 (de)	1975-12-18	1975-12-18	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel

Publications (1)

Publication Number	Publication Date
CH632487A5 true CH632487A5 (en)	1982-10-15

Family

ID=25769723

Family Applications (6)

Application Number	Title	Priority Date	Filing Date
CH1560476A CH632487A5 (en)	1975-12-11	1976-12-10	Process for preparing novel cyanoacetanilide derivatives
CH250581A CH629755A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250681A CH630342A5 (en)	1975-12-11	1981-04-14	Process for the preparation of novel cyanoacetic acid anilide derivatives.
CH250781A CH629756A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250881A CH629757A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250481A CH630341A5 (en)	1975-12-11	1981-04-14	Process for the preparation of novel cyanoacetic anilide derivatives.

Family Applications After (5)

Application Number	Title	Priority Date	Filing Date
CH250581A CH629755A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250681A CH630342A5 (en)	1975-12-11	1981-04-14	Process for the preparation of novel cyanoacetic acid anilide derivatives.
CH250781A CH629756A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250881A CH629757A5 (en)	1975-12-11	1981-04-14	Process for the preparation of cyanoacetanilide derivatives
CH250481A CH630341A5 (en)	1975-12-11	1981-04-14	Process for the preparation of novel cyanoacetic anilide derivatives.

Country Status (12)

Country	Link
JP (1)	JPS5273830A (da)
CA (1)	CA1092133A (da)
CH (6)	CH632487A5 (da)
DK (1)	DK545976A (da)
ES (6)	ES453963A2 (da)
FR (1)	FR2334350A2 (da)
GB (1)	GB1571990A (da)
IE (1)	IE44047B1 (da)
IT (1)	IT1124789B (da)
LU (1)	LU76354A1 (da)
MX (1)	MX4758E (da)
NL (1)	NL7613547A (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0088545B1 (en) *	1982-03-05	1985-12-11	Fbc Limited	Fungicidal cyanopropenoates and compositions containing them
DE3534440A1 (de) *	1985-09-27	1987-04-02	Hoechst Ag	Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes
GB8619432D0 (en) *	1986-08-08	1986-09-17	Lilly Industries Ltd	Pharmaceutical compounds
GB8619433D0 (en) *	1986-08-08	1986-09-17	Lilly Industries Ltd	Pharmaceutical compounds
US6355678B1 (en) *	1998-06-29	2002-03-12	Parker Hughes Institute	Inhibitors of the EGF-receptor tyrosine kinase and methods for their use
EP2303835A1 (en) *	2008-07-29	2011-04-06	Alembic Limited	A process for the preparation of teriflunomide

1976
- 1976-12-03 DK DK545976A patent/DK545976A/da not_active Application Discontinuation
- 1976-12-04 ES ES453963A patent/ES453963A2/es not_active Expired
- 1976-12-06 NL NL7613547A patent/NL7613547A/xx not_active Application Discontinuation
- 1976-12-09 IT IT30233/76A patent/IT1124789B/it active
- 1976-12-09 LU LU76354A patent/LU76354A1/xx unknown
- 1976-12-10 IE IE2706/76A patent/IE44047B1/en unknown
- 1976-12-10 CA CA267,670A patent/CA1092133A/en not_active Expired
- 1976-12-10 CH CH1560476A patent/CH632487A5/de not_active IP Right Cessation
- 1976-12-10 MX MX765215U patent/MX4758E/es unknown
- 1976-12-11 JP JP51148336A patent/JPS5273830A/ja active Pending
- 1976-12-13 FR FR7637514A patent/FR2334350A2/fr active Granted
- 1976-12-13 GB GB51910/76A patent/GB1571990A/en not_active Expired
1978
- 1978-02-01 ES ES466542A patent/ES466542A2/es not_active Expired
- 1978-11-15 ES ES475111A patent/ES475111A1/es not_active Expired
- 1978-11-15 ES ES475109A patent/ES475109A1/es not_active Expired
- 1978-11-15 ES ES475108A patent/ES475108A2/es not_active Expired
- 1978-11-15 ES ES475110A patent/ES475110A1/es not_active Expired
1981
- 1981-04-14 CH CH250581A patent/CH629755A5/de not_active IP Right Cessation
- 1981-04-14 CH CH250681A patent/CH630342A5/de not_active IP Right Cessation
- 1981-04-14 CH CH250781A patent/CH629756A5/de not_active IP Right Cessation
- 1981-04-14 CH CH250881A patent/CH629757A5/de not_active IP Right Cessation
- 1981-04-14 CH CH250481A patent/CH630341A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH630342A5 (en)	1982-06-15
CH629757A5 (en)	1982-05-14
MX4758E (es)	1982-09-03
LU76354A1 (da)	1977-06-24
DK545976A (da)	1977-06-12
ES466542A2 (es)	1979-01-16
IE44047L (en)	1977-06-11
CH630341A5 (en)	1982-06-15
CH629756A5 (en)	1982-05-14
NL7613547A (nl)	1977-06-14
JPS5273830A (en)	1977-06-21
IE44047B1 (en)	1981-07-29
ES475110A1 (es)	1979-05-01
IT1124789B (it)	1986-05-14
GB1571990A (en)	1980-07-23
FR2334350B2 (da)	1980-03-07
CA1092133A (en)	1980-12-23
ES475111A1 (es)	1979-05-01
ES453963A2 (es)	1978-05-01
CH629755A5 (en)	1982-05-14
ES475108A2 (es)	1979-08-01
ES475109A1 (es)	1979-04-16
FR2334350A2 (fr)	1977-07-08

Legal Events

Date	Code	Title	Description
1988-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH633515A5 (de)	1982-12-15	Substituierte phenylessigsaeurederivate und verfahren zu ihrer herstellung.
DE2555789A1 (de)	1977-07-07	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
DE1695044A1 (de)	1972-04-20	Verfahren zur Herstellung von neuen,substituierten Phenylessigsaeuren und deren Estern
EP0125506A1 (de)	1984-11-21	5-(2,6-Dichlor-4-trifluormethyl-phenoxy)-2-nitrobenzaldehyd-diacetacylal
DE2637098A1 (de)	1977-02-24	Phenoxyalkylcarbonsaeurederivate und verfahren zu ihrer herstellung
DE1815802A1 (de)	1969-07-10	Verfahren zur Herstellung von substituierten Phenylessigsaeuren
EP0380712B1 (de)	1995-01-04	Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten
CH632487A5 (en)	1982-10-15	Process for preparing novel cyanoacetanilide derivatives
DE1618465C3 (de)	1979-05-31	Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2225190C3 (de)	1982-01-21	Neue Acetophenonoximderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE2828578A1 (de)	1979-01-11	Thiazolidine und ihre salze sowie verfahren zu ihrer herstellung
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
DE2907379A1 (de)	1979-09-06	Benzylidenderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2804894A1 (de)	1978-08-17	Halogen-benzofuranon-carbonsaeuren
DE2007700C2 (de)	1983-04-28	Substituierte o-Anilino-phenäthylalkohole, Verfahren zu ihrer Herstellung und therapeutische Präparate
DE1668990A1 (de)	1971-10-14	Halogensubstituierte p-(p-Alkoxyphenoxy)-phenoxyalkancarbonsaeuren und die entsprechenden Alkylester und Alkancarbonsaeureamide
DE2934375A1 (de)	1980-06-12	Hydroxyessigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen
DE2943809A1 (de)	1980-05-14	1-mercaptoacylpiperazin-2-carbonsaeure-verbindungen und ihre salze, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von hypertonie
DE2555685A1 (de)	1977-06-23	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
EP0115811B1 (de)	1990-04-18	2,4-Dichlor-5-thiazolcarboxaldehyd und ein Verfahren zu seiner Herstellung
EP0345464B1 (de)	1993-03-17	Verfahren zur Herstellung von substituierten 3-Amino-2(benzoyl)-acrylsäureestern sowie ein Verfahren zur Herstellung von Zwischenprodukten für antibakterielle Wirkstoffe aus diesen Verbindungen
DE2557003A1 (de)	1977-06-23	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
DE2154525A1 (de)	1972-06-15	Isoindolinderivate und Verfahren zu ihrer Herstellung
DE2302671A1 (de)	1973-07-26	5-acylpyrrole, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon