CS253730B2 - Process for preparing new substituted amides - Google Patents

Process for preparing new substituted amides Download PDF

Info

Publication number: CS253730B2
Authority: CS; Czechoslovakia
Prior art keywords: het; radical; alkyl; product; acid
Prior art date: 1984-07-19

Application number

CS855344A

Other languages

Czech (cs)

English (en)

Inventor

Claude Cotrel

Calude Guyon

Gerard Roussel

Gerard Taurand

Original Assignee

Rhone Poulenc Sante

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.)

1984-07-19

Filing date

1985-07-18

Publication date

1987-12-17

1985-07-18 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1987-12-17 Publication of CS253730B2 publication Critical patent/CS253730B2/cs

Links

150000001408 amides Chemical class 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 93
-1 alkyloxy radical Chemical class 0.000 claims abstract description 63
150000001875 compounds Chemical class 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
239000000460 chlorine Substances 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
239000011737 fluorine Substances 0.000 claims abstract description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
150000003254 radicals Chemical class 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 40
150000001412 amines Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 77
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract description 6
239000008194 pharmaceutical composition Substances 0.000 abstract description 5
239000001961 anticonvulsive agent Substances 0.000 abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
230000003556 anti-epileptic effect Effects 0.000 abstract description 2
239000002249 anxiolytic agent Substances 0.000 abstract description 2
125000001246 bromo group Chemical group Br* 0.000 abstract description 2
239000003158 myorelaxant agent Substances 0.000 abstract description 2
125000005554 pyridyloxy group Chemical group 0.000 abstract description 2
125000001544 thienyl group Chemical group 0.000 abstract description 2
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical group [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000006404 alkylpyridazinyl group Chemical group 0.000 abstract 1
229940125681 anticonvulsant agent Drugs 0.000 abstract 1
229960003965 antiepileptics Drugs 0.000 abstract 1
230000000949 anxiolytic effect Effects 0.000 abstract 1
229940005530 anxiolytics Drugs 0.000 abstract 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 abstract 1
239000003326 hypnotic agent Substances 0.000 abstract 1
230000000147 hypnotic effect Effects 0.000 abstract 1
229940035363 muscle relaxants Drugs 0.000 abstract 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 abstract 1
125000002098 pyridazinyl group Chemical group 0.000 abstract 1
125000005942 tetrahydropyridyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
239000000047 product Substances 0.000 description 106
238000009835 boiling Methods 0.000 description 77
239000007787 solid Substances 0.000 description 77
239000000203 mixture Substances 0.000 description 68
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
238000001914 filtration Methods 0.000 description 57
239000000243 solution Substances 0.000 description 50
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 34
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 31
238000001556 precipitation Methods 0.000 description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
239000000377 silicon dioxide Substances 0.000 description 23
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 18
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 17
239000002245 particle Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
238000001816 cooling Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
239000008188 pellet Substances 0.000 description 11
HRXBYPUUCBEZAS-UHFFFAOYSA-N 7-chloro-1,8-naphthyridin-2-amine Chemical compound C1=CC(Cl)=NC2=NC(N)=CC=C21 HRXBYPUUCBEZAS-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000003826 tablet Substances 0.000 description 10
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 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000012265 solid product Substances 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
KKBLBTVDIAFYMX-UHFFFAOYSA-N 7-phenoxy-1,8-naphthyridin-2-amine Chemical compound N=1C2=NC(N)=CC=C2C=CC=1OC1=CC=CC=C1 KKBLBTVDIAFYMX-UHFFFAOYSA-N 0.000 description 5
239000005711 Benzoic acid Substances 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
239000007789 gas Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 4
SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 3
WLEQWVIWIDRMKX-UHFFFAOYSA-N 7-methoxy-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OC)=CC=C21 WLEQWVIWIDRMKX-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical compound [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
239000003814 drug Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
235000011837 pasties Nutrition 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
CRADWWWVIYEAFR-UHFFFAOYSA-N 1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N)=CC=C21 CRADWWWVIYEAFR-UHFFFAOYSA-N 0.000 description 2
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 2
NZQMQVJXSRMTCJ-UHFFFAOYSA-N 3-Methyl-hexanoic acid Chemical compound CCCC(C)CC(O)=O NZQMQVJXSRMTCJ-UHFFFAOYSA-N 0.000 description 2
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
CMRAQYCMKYPSHS-UHFFFAOYSA-N 7-(2-methylphenoxy)-1,8-naphthyridin-2-amine Chemical compound CC1=CC=CC=C1OC1=CC=C(C=CC(N)=N2)C2=N1 CMRAQYCMKYPSHS-UHFFFAOYSA-N 0.000 description 2
WTENBEVTXORPNQ-UHFFFAOYSA-N 7-(3-methoxyphenoxy)-1,8-naphthyridin-2-amine Chemical compound COC1=CC=CC(OC=2N=C3N=C(N)C=CC3=CC=2)=C1 WTENBEVTXORPNQ-UHFFFAOYSA-N 0.000 description 2
KZAGTKAAUSTBMG-UHFFFAOYSA-N 7-methylsulfanyl-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(SC)=CC=C21 KZAGTKAAUSTBMG-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000755093 Gaidropsarus vulgaris Species 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000013078 crystal Substances 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000009499 grossing Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
208000037797 influenza A Diseases 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000000829 suppository Substances 0.000 description 2
150000007944 thiolates Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
NCOUTKLISVDYKS-UHFFFAOYSA-N (3-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(Cl)=O)=C1 NCOUTKLISVDYKS-UHFFFAOYSA-N 0.000 description 1
125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
RALDFFKZZOKOJN-UHFFFAOYSA-N 1-ethoxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound CCOC1(C(O)=O)CC=CC=C1 RALDFFKZZOKOJN-UHFFFAOYSA-N 0.000 description 1
AKPPNCZQONZIHZ-UHFFFAOYSA-N 1-fluorocyclohexa-2,4-dien-1-ol Chemical compound OC1(F)CC=CC=C1 AKPPNCZQONZIHZ-UHFFFAOYSA-N 0.000 description 1
DWEWWSUVOKCQSK-UHFFFAOYSA-N 1-methoxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound COC1(C(O)=O)CC=CC=C1 DWEWWSUVOKCQSK-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
XXNBGDQACLGWAC-UHFFFAOYSA-N 2,6-difluoro-n-(7-methoxy-1,8-naphthyridin-2-yl)benzamide Chemical compound N=1C2=NC(OC)=CC=C2C=CC=1NC(=O)C1=C(F)C=CC=C1F XXNBGDQACLGWAC-UHFFFAOYSA-N 0.000 description 1
ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Toxicology (AREA)
Anesthesiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Materials For Medical Uses (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Cephalosporin Compounds (AREA)
Quinoline Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CS855344A 1984-07-19 1985-07-18 Process for preparing new substituted amides CS253730B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8411442A FR2567887B1 (fr)	1984-07-19	1984-07-19	Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent

Publications (1)

Publication Number	Publication Date
CS253730B2 true CS253730B2 (en)	1987-12-17

Family

ID=9306273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS855344A CS253730B2 (en)	1984-07-19	1985-07-18	Process for preparing new substituted amides

Country Status (27)

Country	Link
US (1)	US4642308A (pl)
EP (1)	EP0172083B1 (pl)
JP (1)	JPS6163656A (pl)
KR (1)	KR860001100A (pl)
AT (1)	ATE33652T1 (pl)
AU (1)	AU572672B2 (pl)
CA (1)	CA1224787A (pl)
CS (1)	CS253730B2 (pl)
DD (1)	DD240011A5 (pl)
DE (1)	DE3562250D1 (pl)
DK (1)	DK327285A (pl)
ES (1)	ES8604584A1 (pl)
FI (1)	FI79313C (pl)
FR (1)	FR2567887B1 (pl)
GR (1)	GR851774B (pl)
HU (1)	HU199802B (pl)
IL (1)	IL75817A (pl)
MA (1)	MA20487A1 (pl)
NO (1)	NO161673C (pl)
NZ (1)	NZ212764A (pl)
OA (1)	OA08069A (pl)
PH (1)	PH21301A (pl)
PL (1)	PL145331B1 (pl)
PT (1)	PT80840B (pl)
SU (1)	SU1417797A3 (pl)
YU (1)	YU118785A (pl)
ZA (1)	ZA855409B (pl)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0208621B1 (fr) *	1985-07-11	1989-04-12	Rhone-Poulenc Sante	Amides substitués, leur préparation et compositions qui les contiennent
FR2592882B2 (fr) *	1986-01-16	1988-03-11	Rhone Poulenc Sante	Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent
US4753941A (en) *	1986-01-16	1988-06-28	Rhone-Poulenc Sante	Amides based on certain 1,8-naphtyridine-2-amines useful as anxiolytics
US5197518A (en) *	1991-06-27	1993-03-30	Double Containment Systems	Centering support assembly for double containment pipe systems
GB9711257D0 (en)	1997-05-30	1997-07-30	Smithkline Beecham Plc	Novel compounds
US6340690B1 (en) *	1999-02-22	2002-01-22	Bio-Chem Pharma Inc.	Antiviral methods using [1,8]naphthyridine derivatives
WO2005046683A1 (en)	2003-10-07	2005-05-26	Renovis, Inc.	Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7576099B2 (en)	2005-02-28	2009-08-18	Renovis, Inc.	Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US20080300243A1 (en) *	2005-02-28	2008-12-04	Kelly Michael G	Amide Derivatives as Ion-Channel Ligands and Pharmaceutical Compositions and Methods of Using the Same
US20150011569A1 (en) *	2011-12-15	2015-01-08	Philadelphia Health & Education Corporation D/B/A Drexel University College Of Medicine	NOVEL P13K p110 INHIBITORS AND METHODS OF USE THEREOF
CN105646487B (zh) *	2016-03-15	2017-12-05	红河学院	一类溴代1,8‑萘啶衍生物及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB661515A (en) *	1948-08-31	1951-11-21	Cilag Ltd	Process for the production of naphthyridine derivatives
FR1006725A (fr) *	1948-08-31	1952-04-28	Cilag Spa	Nouveaux dérivés de la naphtyridine et procédé pour leur préparation
US3389142A (en) *	1966-09-29	1968-06-18	Bristol Myers Co	Esters of 2-substituted 1, 2-dihydroquinoline-nu-carboxylic acids and thione acids
US3576809A (en) *	1968-05-06	1971-04-27	Miles Lab	2-substituted derivatives of 6-methoxyquinoline
US3624097A (en) *	1969-07-22	1971-11-30	Warner Lambert Co	N-pyridine 5-aminooxazoles
US4466965A (en) *	1982-07-26	1984-08-21	American Hospital Supply Corporation	Phthalazine compounds, compositions and use

1984
- 1984-07-19 FR FR8411442A patent/FR2567887B1/fr not_active Expired
1985
- 1985-06-28 CA CA000485859A patent/CA1224787A/fr not_active Expired
- 1985-07-15 IL IL75817A patent/IL75817A/xx unknown
- 1985-07-16 MA MA20712A patent/MA20487A1/fr unknown
- 1985-07-17 ZA ZA855409A patent/ZA855409B/xx unknown
- 1985-07-17 AU AU45090/85A patent/AU572672B2/en not_active Ceased
- 1985-07-17 NZ NZ212764A patent/NZ212764A/en unknown
- 1985-07-17 US US06/755,896 patent/US4642308A/en not_active Expired - Fee Related
- 1985-07-17 DD DD85278694A patent/DD240011A5/de unknown
- 1985-07-17 PL PL1985254570A patent/PL145331B1/pl unknown
- 1985-07-17 GR GR851774A patent/GR851774B/el unknown
- 1985-07-18 DK DK327285A patent/DK327285A/da not_active Application Discontinuation
- 1985-07-18 CS CS855344A patent/CS253730B2/cs unknown
- 1985-07-18 EP EP85401480A patent/EP0172083B1/fr not_active Expired
- 1985-07-18 ES ES545336A patent/ES8604584A1/es not_active Expired
- 1985-07-18 NO NO852877A patent/NO161673C/no unknown
- 1985-07-18 FI FI852821A patent/FI79313C/fi not_active IP Right Cessation
- 1985-07-18 SU SU853923698A patent/SU1417797A3/ru active
- 1985-07-18 DE DE8585401480T patent/DE3562250D1/de not_active Expired
- 1985-07-18 AT AT85401480T patent/ATE33652T1/de not_active IP Right Cessation
- 1985-07-18 KR KR1019850005134A patent/KR860001100A/ko not_active Withdrawn
- 1985-07-18 HU HU852764A patent/HU199802B/hu not_active IP Right Cessation
- 1985-07-18 PH PH32541A patent/PH21301A/en unknown
- 1985-07-19 JP JP60158504A patent/JPS6163656A/ja active Pending
- 1985-07-19 YU YU01187/85A patent/YU118785A/xx unknown
- 1985-07-19 PT PT80840A patent/PT80840B/pt not_active IP Right Cessation
- 1985-07-19 OA OA58648A patent/OA08069A/xx unknown

Also Published As

Publication number	Publication date
FI852821L (fi)	1986-01-20
YU118785A (en)	1988-10-31
FR2567887A1 (fr)	1986-01-24
DE3562250D1 (en)	1988-05-26
DK327285A (da)	1986-01-20
NO161673C (no)	1989-09-13
IL75817A (en)	1988-06-30
PL145331B1 (en)	1988-09-30
HU199802B (en)	1990-03-28
ES8604584A1 (es)	1986-02-01
JPS6163656A (ja)	1986-04-01
FI79313B (fi)	1989-08-31
AU572672B2 (en)	1988-05-12
PH21301A (en)	1987-09-28
ZA855409B (en)	1986-04-30
CA1224787A (fr)	1987-07-28
IL75817A0 (en)	1985-11-29
PL254570A1 (en)	1986-10-21
DD240011A5 (de)	1986-10-15
EP0172083A1 (fr)	1986-02-19
FR2567887B1 (fr)	1986-12-19
EP0172083B1 (fr)	1988-04-20
NZ212764A (en)	1988-05-30
US4642308A (en)	1987-02-10
ES545336A0 (es)	1986-02-01
AU4509085A (en)	1986-01-23
OA08069A (fr)	1987-03-31
SU1417797A3 (ru)	1988-08-15
FI79313C (fi)	1989-12-11
HUT40799A (en)	1987-02-27
FI852821A0 (fi)	1985-07-18
PT80840B (pt)	1988-02-17
MA20487A1 (fr)	1986-04-01
ATE33652T1 (de)	1988-05-15
KR860001100A (ko)	1986-02-22
PT80840A (fr)	1985-08-01
DK327285D0 (da)	1985-07-18
GR851774B (pl)	1985-11-26
NO852877L (no)	1986-01-20
NO161673B (no)	1989-06-05

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