DD260069A5 - Verfahren zur herstellung eines substituierten amides - Google Patents

Verfahren zur herstellung eines substituierten amides Download PDF

Info

Publication number: DD260069A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; substituted; temperature; het; alkyl
Prior art date: 1986-01-16

Application number

DD87299275A

Other languages

German (de)

English (en)

Inventor

Claude Cotrel

Claude Guyon

Gerard Roussel

Gerad Taurand

Original Assignee

��`��@��k��

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.)

1986-01-16

Filing date

1987-01-15

Publication date

1988-09-14

1987-01-15 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1988-09-14 Publication of DD260069A5 publication Critical patent/DD260069A5/de

Links

150000001408 amides Chemical class 0.000 title claims abstract description 18
238000004519 manufacturing process Methods 0.000 title 1
-1 alkyloxy-3-pyridyl Chemical group 0.000 claims abstract description 56
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Chemical group 0.000 claims abstract description 5
229910052717 sulfur Chemical group 0.000 claims abstract description 5
239000011593 sulfur Chemical group 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
125000006404 alkylpyridazinyl group Chemical group 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 3
125000005942 tetrahydropyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 71
238000000034 method Methods 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 12
239000001961 anticonvulsive agent Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
230000003556 anti-epileptic effect Effects 0.000 claims description 5
229960003965 antiepileptics Drugs 0.000 claims description 5
239000002249 anxiolytic agent Substances 0.000 claims description 5
230000000949 anxiolytic effect Effects 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000000147 hypnotic effect Effects 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
230000001773 anti-convulsant effect Effects 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
230000001670 myorelaxant effect Effects 0.000 claims description 3
230000000144 pharmacologic effect Effects 0.000 claims description 3
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
229940125681 anticonvulsant agent Drugs 0.000 claims description 2
229940005530 anxiolytics Drugs 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000003326 hypnotic agent Substances 0.000 claims description 2
239000003158 myorelaxant agent Substances 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 abstract 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
239000000047 product Substances 0.000 description 51
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
238000001914 filtration Methods 0.000 description 45
239000000203 mixture Substances 0.000 description 44
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 37
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
238000002844 melting Methods 0.000 description 34
230000008018 melting Effects 0.000 description 34
239000007787 solid Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 28
239000012153 distilled water Substances 0.000 description 27
229910052943 magnesium sulfate Inorganic materials 0.000 description 24
235000019341 magnesium sulphate Nutrition 0.000 description 24
238000001816 cooling Methods 0.000 description 23
239000000284 extract Substances 0.000 description 22
238000009835 boiling Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 17
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
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 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000007937 lozenge Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
LZIRDGWKVQLVEB-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OCCN(C)C)=CC=C21 LZIRDGWKVQLVEB-UHFFFAOYSA-N 0.000 description 4
239000005711 Benzoic acid Substances 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
OVSUWMULYOBJKG-UHFFFAOYSA-N 2-[(7-amino-1,8-naphthyridin-2-yl)oxy]-n,n-dimethylacetamide Chemical compound C1=CC(N)=NC2=NC(OCC(=O)N(C)C)=CC=C21 OVSUWMULYOBJKG-UHFFFAOYSA-N 0.000 description 3
XSCIVBWMVPZSKT-UHFFFAOYSA-N 7-(2-morpholin-4-ylethoxy)-1,8-naphthyridin-2-amine Chemical compound N=1C2=NC(N)=CC=C2C=CC=1OCCN1CCOCC1 XSCIVBWMVPZSKT-UHFFFAOYSA-N 0.000 description 3
MKBCLERCERRJCI-UHFFFAOYSA-N 7-[2-(dimethylamino)ethylsulfanyl]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(SCCN(C)C)=CC=C21 MKBCLERCERRJCI-UHFFFAOYSA-N 0.000 description 3
AHGODFOWHDYAJV-UHFFFAOYSA-N 7-[3-(dimethylamino)propoxy]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OCCCN(C)C)=CC=C21 AHGODFOWHDYAJV-UHFFFAOYSA-N 0.000 description 3
PWBHJQUTCLXRJB-UHFFFAOYSA-N 7-[3-(dimethylamino)propylsulfanyl]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(SCCCN(C)C)=CC=C21 PWBHJQUTCLXRJB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000945 filler Substances 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
RFDSJHHLGFFVHD-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)-n-methylcarbamate Chemical compound OCCN(C)C(=O)OC(C)(C)C RFDSJHHLGFFVHD-UHFFFAOYSA-N 0.000 description 3
VUVCYQCWNBTSMI-UHFFFAOYSA-N tert-butyl n-[2-[(7-amino-1,8-naphthyridin-2-yl)oxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(N)=NC2=NC(OCCN(C)C(=O)OC(C)(C)C)=CC=C21 VUVCYQCWNBTSMI-UHFFFAOYSA-N 0.000 description 3
150000007944 thiolates Chemical class 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QHTUMQYGZQYEOZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanol Chemical compound CN1CCN(CCO)CC1 QHTUMQYGZQYEOZ-UHFFFAOYSA-N 0.000 description 2
LRQYSIQVFJYQNK-UHFFFAOYSA-N 4-(ethoxycarbonylamino)benzoic acid Chemical compound CCOC(=O)NC1=CC=C(C(O)=O)C=C1 LRQYSIQVFJYQNK-UHFFFAOYSA-N 0.000 description 2
SWXFMMWYVSYQGF-UHFFFAOYSA-N 4-(ethylamino)benzoic acid Chemical compound CCNC1=CC=C(C(O)=O)C=C1 SWXFMMWYVSYQGF-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 2
ICFUGWWFOGOGDO-UHFFFAOYSA-N 4-methoxy-n-(7-methyl-1,8-naphthyridin-2-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(C)=N2)C2=N1 ICFUGWWFOGOGDO-UHFFFAOYSA-N 0.000 description 2
QOZUBKDPMJBBDN-UHFFFAOYSA-N 7-[2-(4-methylpiperazin-1-yl)ethoxy]-1,8-naphthyridin-2-amine Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=CC(N)=N2)C2=N1 QOZUBKDPMJBBDN-UHFFFAOYSA-N 0.000 description 2
OPERDIPWTWYICD-UHFFFAOYSA-N 7-[3-(dimethylamino)-2-methylpropoxy]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OCC(C)CN(C)C)=CC=C21 OPERDIPWTWYICD-UHFFFAOYSA-N 0.000 description 2
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 2
ZIFGWWCUONMOLI-UHFFFAOYSA-N 7-methyl-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(C)=CC=C21 ZIFGWWCUONMOLI-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
HIWJESWAIXHXHI-UHFFFAOYSA-N n-[7-[3-(diethylamino)propoxy]-1,8-naphthyridin-2-yl]-4-methoxybenzamide Chemical compound N=1C2=NC(OCCCN(CC)CC)=CC=C2C=CC=1NC(=O)C1=CC=C(OC)C=C1 HIWJESWAIXHXHI-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 1
WSNDAYQNZRJGMJ-UHFFFAOYSA-N 2,2,2-trifluoroethanone Chemical group FC(F)(F)[C]=O WSNDAYQNZRJGMJ-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
XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
GMFRUUXHDGHBJF-UHFFFAOYSA-N 2-(ethoxycarbonylamino)benzoic acid Chemical compound CCOC(=O)NC1=CC=CC=C1C(O)=O GMFRUUXHDGHBJF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
FZASHPCRPMSFEG-UHFFFAOYSA-N 3-(dimethylamino)-2-methylpropan-1-ol Chemical compound OCC(C)CN(C)C FZASHPCRPMSFEG-UHFFFAOYSA-N 0.000 description 1
PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
HSAYSFNFCZEPCN-UHFFFAOYSA-N 3-(dimethylamino)propane-1-thiol Chemical compound CN(C)CCCS HSAYSFNFCZEPCN-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HXIBKZKPQBLHGV-UHFFFAOYSA-N 4-(ethylamino)-n-(7-methoxy-1,8-naphthyridin-2-yl)benzamide Chemical compound C1=CC(NCC)=CC=C1C(=O)NC1=CC=C(C=CC(OC)=N2)C2=N1 HXIBKZKPQBLHGV-UHFFFAOYSA-N 0.000 description 1
LQJPCBSYOUFFPO-UHFFFAOYSA-N 4-methoxy-n-[7-[2-(methylamino)ethoxy]-1,8-naphthyridin-2-yl]benzamide Chemical compound N=1C2=NC(OCCNC)=CC=C2C=CC=1NC(=O)C1=CC=C(OC)C=C1 LQJPCBSYOUFFPO-UHFFFAOYSA-N 0.000 description 1
ANEHFOVKUJADNR-UHFFFAOYSA-N 7-[3-(diethylamino)propoxy]-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OCCCN(CC)CC)=CC=C21 ANEHFOVKUJADNR-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
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235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
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239000007903 gelatin capsule Substances 0.000 description 1
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238000002329 infrared spectrum Methods 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
OWIUVLLLPHCBGQ-UHFFFAOYSA-N n-[7-[2-(dimethylamino)ethoxy]-1,8-naphthyridin-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(OCCN(C)C)=N2)C2=N1 OWIUVLLLPHCBGQ-UHFFFAOYSA-N 0.000 description 1
UEAHFPGLKGWPHP-UHFFFAOYSA-N n-[7-[2-(dimethylamino)ethoxy]-1,8-naphthyridin-2-yl]benzamide Chemical compound N=1C2=NC(OCCN(C)C)=CC=C2C=CC=1NC(=O)C1=CC=CC=C1 UEAHFPGLKGWPHP-UHFFFAOYSA-N 0.000 description 1
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SMFHHLUKSMNEJL-UHFFFAOYSA-N n-[7-[2-(dimethylamino)ethylsulfanyl]-1,8-naphthyridin-2-yl]-4-methoxybenzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(SCCN(C)C)=N2)C2=N1 SMFHHLUKSMNEJL-UHFFFAOYSA-N 0.000 description 1
JQCJLLQMDNWEOZ-UHFFFAOYSA-N n-[7-[3-(dimethylamino)propoxy]-1,8-naphthyridin-2-yl]-2,6-difluorobenzamide Chemical compound N=1C2=NC(OCCCN(C)C)=CC=C2C=CC=1NC(=O)C1=C(F)C=CC=C1F JQCJLLQMDNWEOZ-UHFFFAOYSA-N 0.000 description 1
IZJQTYNCRYFJIM-UHFFFAOYSA-N n-[7-[3-(dimethylamino)propoxy]-1,8-naphthyridin-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(OCCCN(C)C)=N2)C2=N1 IZJQTYNCRYFJIM-UHFFFAOYSA-N 0.000 description 1
ADBXHTXPLWJONP-UHFFFAOYSA-N n-[7-[3-(dimethylamino)propoxy]-1,8-naphthyridin-2-yl]cyclopropanecarboxamide Chemical compound N=1C2=NC(OCCCN(C)C)=CC=C2C=CC=1NC(=O)C1CC1 ADBXHTXPLWJONP-UHFFFAOYSA-N 0.000 description 1
ZPECQPQMGJJBDX-UHFFFAOYSA-N n-[7-[3-(dimethylamino)propylsulfanyl]-1,8-naphthyridin-2-yl]-4-methoxybenzamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(SCCCN(C)C)=N2)C2=N1 ZPECQPQMGJJBDX-UHFFFAOYSA-N 0.000 description 1
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150000002823 nitrates Chemical class 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
239000000810 peripheral vasodilating agent Substances 0.000 description 1
229960002116 peripheral vasodilator Drugs 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
238000000053 physical method Methods 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
FQVOSMFIZYLWEF-UHFFFAOYSA-N tert-butyl n-[2-[[7-[(4-methoxybenzoyl)amino]-1,8-naphthyridin-2-yl]oxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=CC(OCCN(C)C(=O)OC(C)(C)C)=N2)C2=N1 FQVOSMFIZYLWEF-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Neurology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Anesthesiology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cephalosporin Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
Reinforced Plastic Materials (AREA)
Protection Of Plants (AREA)

DD87299275A 1986-01-16 1987-01-15 Verfahren zur herstellung eines substituierten amides DD260069A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8600556A FR2592882B2 (fr)	1986-01-16	1986-01-16	Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent

Publications (1)

Publication Number	Publication Date
DD260069A5 true DD260069A5 (de)	1988-09-14

Family

ID=9331170

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87299275A DD260069A5 (de)	1986-01-16	1987-01-15	Verfahren zur herstellung eines substituierten amides

Country Status (21)

Country	Link
US (1)	US4753933A (cs)
EP (1)	EP0234971B1 (cs)
JP (1)	JPS62169787A (cs)
KR (1)	KR870007169A (cs)
AT (1)	ATE56213T1 (cs)
AU (1)	AU589484B2 (cs)
CS (1)	CS262446B2 (cs)
DD (1)	DD260069A5 (cs)
DE (1)	DE3764667D1 (cs)
DK (1)	DK19787A (cs)
ES (1)	ES2018025B3 (cs)
FI (1)	FI870150A7 (cs)
FR (1)	FR2592882B2 (cs)
HU (1)	HU196070B (cs)
IE (1)	IE870126L (cs)
NO (1)	NO164836C (cs)
PH (1)	PH24461A (cs)
PL (1)	PL263677A3 (cs)
PT (1)	PT84101B (cs)
YU (1)	YU46041B (cs)
ZA (1)	ZA87292B (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5258356A (en) *	1989-03-11	1993-11-02	Basf Aktiengesellschaft	Substituted 1,8-naphthyridines, their preparation and their use as antidotes
EP1195372A1 (en) *	1994-04-18	2002-04-10	Mitsubishi Pharma Corporation	N-heterocyclic substituted benzamide derivatives with antihypertensive activity
WO1997024401A1 (en) *	1995-12-27	1997-07-10	Sumitomo Bakelite Company Limited	Process for producing flame-retardant, silane-crosslinked polyolefin
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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1006725A (fr) *	1948-08-31	1952-04-28	Cilag Spa	Nouveaux dérivés de la naphtyridine et procédé pour leur préparation
FR2567887B1 (fr) *	1984-07-19	1986-12-19	Rhone Poulenc Sante	Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent
EP0208621B1 (fr) *	1985-07-11	1989-04-12	Rhone-Poulenc Sante	Amides substitués, leur préparation et compositions qui les contiennent

1986
- 1986-01-16 FR FR8600556A patent/FR2592882B2/fr not_active Expired
1987
- 1987-01-13 PT PT84101A patent/PT84101B/pt not_active IP Right Cessation
- 1987-01-13 US US07/002,929 patent/US4753933A/en not_active Expired - Fee Related
- 1987-01-14 JP JP62005156A patent/JPS62169787A/ja active Pending
- 1987-01-14 CS CS87256A patent/CS262446B2/cs unknown
- 1987-01-15 AU AU67602/87A patent/AU589484B2/en not_active Ceased
- 1987-01-15 ZA ZA87292A patent/ZA87292B/xx unknown
- 1987-01-15 AT AT87400078T patent/ATE56213T1/de not_active IP Right Cessation
- 1987-01-15 KR KR870000275A patent/KR870007169A/ko not_active Withdrawn
- 1987-01-15 YU YU5387A patent/YU46041B/sh unknown
- 1987-01-15 NO NO870166A patent/NO164836C/no unknown
- 1987-01-15 EP EP87400078A patent/EP0234971B1/fr not_active Expired - Lifetime
- 1987-01-15 PH PH34726A patent/PH24461A/en unknown
- 1987-01-15 HU HU87118A patent/HU196070B/hu not_active IP Right Cessation
- 1987-01-15 DK DK019787A patent/DK19787A/da not_active Application Discontinuation
- 1987-01-15 DD DD87299275A patent/DD260069A5/de not_active IP Right Cessation
- 1987-01-15 ES ES87400078T patent/ES2018025B3/es not_active Expired - Lifetime
- 1987-01-15 DE DE8787400078T patent/DE3764667D1/de not_active Expired - Fee Related
- 1987-01-15 FI FI870150A patent/FI870150A7/fi not_active Application Discontinuation
- 1987-01-16 PL PL1987263677A patent/PL263677A3/xx unknown
- 1987-01-20 IE IE870126A patent/IE870126L/xx unknown

Also Published As

Publication number	Publication date
HU196070B (en)	1988-09-28
DK19787A (da)	1987-07-17
JPS62169787A (ja)	1987-07-25
FI870150A7 (fi)	1987-07-17
US4753933A (en)	1988-06-28
PL263677A3 (en)	1988-06-09
ES2018025B3 (es)	1991-03-16
PH24461A (en)	1990-06-25
NO164836B (no)	1990-08-13
CS262446B2 (en)	1989-03-14
ZA87292B (en)	1987-08-26
EP0234971B1 (fr)	1990-09-05
AU6760287A (en)	1987-07-23
NO870166L (no)	1987-07-17
YU46041B (sh)	1992-12-21
NO164836C (no)	1990-11-21
PT84101A (fr)	1987-02-01
YU5387A (en)	1988-06-30
KR870007169A (ko)	1987-08-17
NO870166D0 (no)	1987-01-15
AU589484B2 (en)	1989-10-12
EP0234971A1 (fr)	1987-09-02
PT84101B (pt)	1989-07-31
DE3764667D1 (de)	1990-10-11
FI870150A0 (fi)	1987-01-15
ATE56213T1 (de)	1990-09-15
IE870126L (en)	1987-07-16
FR2592882A2 (fr)	1987-07-17
HUT43603A (en)	1987-11-30
DK19787D0 (da)	1987-01-15
FR2592882B2 (fr)	1988-03-11
CS25687A2 (en)	1988-07-15

Legal Events

Date	Code	Title	Description
1994-01-27	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

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