DK141098B - Analogifremgangsmåde til fremstilling af naphthyridinderivater. - Google Patents

Analogifremgangsmåde til fremstilling af naphthyridinderivater. Download PDF

Info

Publication number: DK141098B
Authority: DK; Denmark
Prior art keywords: general formula; naphthyridin; chloro; het; piperazinyl
Prior art date: 1974-11-07

Application number

DK499275AA

Other languages

Danish (da)

English (en)

Other versions

DK499275A (fr

DK141098C (fr

Inventor

Claude Cotrel

Cornel Crisan

Claude Jeanmart

Mayer Naoum Messer

Original Assignee

Rhone Poulenc Ind

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.)

1974-11-07

Filing date

1975-11-06

Publication date

1980-01-14

1974-11-07 Priority claimed from FR7436963A external-priority patent/FR2313060A1/fr

1975-09-04 Priority claimed from FR7527162A external-priority patent/FR2322602A1/fr

1975-09-04 Priority claimed from FR7527161A external-priority patent/FR2322601A1/fr

1975-09-04 Priority claimed from FR7527160A external-priority patent/FR2322600A1/fr

1975-11-06 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1976-05-08 Publication of DK499275A publication Critical patent/DK499275A/da

1980-01-14 Publication of DK141098B publication Critical patent/DK141098B/da

1980-07-07 Application granted granted Critical

1980-07-07 Publication of DK141098C publication Critical patent/DK141098C/da

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 8
150000005054 naphthyridines Chemical class 0.000 title claims description 4
-1 1,8-naphthyridin-2-yl group Chemical group 0.000 claims description 56
150000001875 compounds Chemical class 0.000 claims description 56
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000003233 pyrroles Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
AKGSNUOZGBDODP-UHFFFAOYSA-N piperazine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNCC1 AKGSNUOZGBDODP-UHFFFAOYSA-N 0.000 claims description 2
150000007970 thio esters Chemical class 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
239000000243 solution Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000001914 filtration Methods 0.000 description 22
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239000000203 mixture Substances 0.000 description 19
239000000047 product Substances 0.000 description 16
241000699670 Mus sp. Species 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
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150000008064 anhydrides Chemical class 0.000 description 9
239000000725 suspension Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 8
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239000002244 precipitate Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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238000010438 heat treatment Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
208000007101 Muscle Cramp Diseases 0.000 description 4
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
YEQAMPOYHLICPF-UHFFFAOYSA-N 1-piperazin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCNCC1 YEQAMPOYHLICPF-UHFFFAOYSA-N 0.000 description 3
GKGWOUPKDALZIJ-UHFFFAOYSA-N 4-propanoylpiperazine-1-carbonyl chloride Chemical compound CCC(=O)N1CCN(C(Cl)=O)CC1 GKGWOUPKDALZIJ-UHFFFAOYSA-N 0.000 description 3
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
NSPQTGOJGZXAJM-UHFFFAOYSA-N 7-amino-1h-1,8-naphthyridin-2-one Chemical compound C1=CC(=O)NC2=NC(N)=CC=C21 NSPQTGOJGZXAJM-UHFFFAOYSA-N 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
ZESSRQSTYNMBBB-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)OC1=CC=CC=C1 ZESSRQSTYNMBBB-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
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238000010908 decantation Methods 0.000 description 3
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239000007924 injection Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
UWERZJBLURGYFF-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)O)=CC=C21 UWERZJBLURGYFF-UHFFFAOYSA-N 0.000 description 2
HTIZLJISEUYGSA-UHFFFAOYSA-N 2-chloro-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(Cl)=CC=C21 HTIZLJISEUYGSA-UHFFFAOYSA-N 0.000 description 2
RMPKHFJYALJCOR-UHFFFAOYSA-N 7a-(7-oxo-8h-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(=O)NC2=NC(C34C(=O)NC(C3C=CC=C4)=O)=CC=C21 RMPKHFJYALJCOR-UHFFFAOYSA-N 0.000 description 2
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230000001147 anti-toxic effect Effects 0.000 description 2
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229910000397 disodium phosphate Inorganic materials 0.000 description 2
235000019800 disodium phosphate Nutrition 0.000 description 2
150000003949 imides Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
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238000007920 subcutaneous administration Methods 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
CROUDGNPJLQKNA-UHFFFAOYSA-N [2-(5-chloropyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(Cl)C=N1 CROUDGNPJLQKNA-UHFFFAOYSA-N 0.000 description 1
ZJIVVCJAUCPSRQ-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1H-isoindol-1-yl] 4-acetylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 ZJIVVCJAUCPSRQ-UHFFFAOYSA-N 0.000 description 1
QGFXKQIACHMJLC-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1H-isoindol-1-yl] 4-methanethioylpiperazine-1-carboxylate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)N1CCN(C=S)CC1 QGFXKQIACHMJLC-UHFFFAOYSA-N 0.000 description 1
VGPGDRBZBDONLK-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-(2-methylprop-2-enoyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)C(=C)C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 VGPGDRBZBDONLK-UHFFFAOYSA-N 0.000 description 1
UNSOABGSINKNCQ-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 UNSOABGSINKNCQ-UHFFFAOYSA-N 0.000 description 1
WWBXTUIAKOHXPA-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-prop-2-enoylpiperazine-1-carboxylate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)N1CCN(C(=O)C=C)CC1 WWBXTUIAKOHXPA-UHFFFAOYSA-N 0.000 description 1
DPXCJHBBCLQKQH-UHFFFAOYSA-N [2-(7-chloroquinolin-2-yl)-3-oxo-1H-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(CC1)C(=O)OC1N(C(C2=CC=CC=C12)=O)C1=NC2=CC(=CC=C2C=C1)Cl DPXCJHBBCLQKQH-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000002152 aqueous-organic solution Substances 0.000 description 1
NRIMHVFWRMABGJ-UHFFFAOYSA-N bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid Chemical compound C1C2C(C(=O)O)=C(C(O)=O)C1C=C2 NRIMHVFWRMABGJ-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
AILAQOYFPLQIFN-UHFFFAOYSA-N butyl piperazine-1-carboxylate Chemical compound CCCCOC(=O)N1CCNCC1 AILAQOYFPLQIFN-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
YROXEBCFDJQGOH-UHFFFAOYSA-N ditert-butyl piperazine-1,4-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)CC1 YROXEBCFDJQGOH-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
VVWNENUJKRQDTB-UHFFFAOYSA-N o-ethyl methanethioate Chemical compound CCOC=S VVWNENUJKRQDTB-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
229960000412 strychnine sulfate Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
DEGRJODPOICGRU-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CCNCC1 DEGRJODPOICGRU-UHFFFAOYSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
GBBSUAFBMRNDJC-UHFFFAOYSA-N zopiclone Chemical compound C1CN(C)CCN1C(=O)OC1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-UHFFFAOYSA-N 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
- 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
- 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
- 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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DK499275AA 1974-11-07 1975-11-06 Analogifremgangsmåde til fremstilling af naphthyridinderivater. DK141098B (da)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
FR7436963		1974-11-07
FR7436963A FR2313060A1 (fr)	1974-11-07	1974-11-07	Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent
FR7527162A FR2322602A1 (fr)	1975-09-04	1975-09-04	Nouveaux derives de l'oxathiinno- et du dithiinnopyrrole, leur preparation et les compositions qui les contiennent
FR7527161A FR2322601A1 (fr)	1975-09-04	1975-09-04	Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent
FR7527161		1975-09-04
FR7527160A FR2322600A1 (fr)	1975-09-04	1975-09-04	Nouveaux derives de la pyrrolo (3,4-b) pyrazine, leur preparation et les compositions qui les contiennent
FR7527162		1975-09-04
FR7527160		1975-09-04

Publications (3)

Publication Number	Publication Date
DK499275A DK499275A (fr)	1976-05-08
DK141098B true DK141098B (da)	1980-01-14
DK141098C DK141098C (fr)	1980-07-07

Family

ID=27446274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK499275AA DK141098B (da)	1974-11-07	1975-11-06	Analogifremgangsmåde til fremstilling af naphthyridinderivater.

Country Status (27)

Country	Link
US (1)	US4220646A (fr)
JP (2)	JPS5422996B2 (fr)
AR (2)	AR208414A1 (fr)
AT (2)	AT343123B (fr)
AU (1)	AU503200B2 (fr)
BE (1)	BE835325A (fr)
CA (1)	CA1057755A (fr)
CH (1)	CH609057A5 (fr)
CS (2)	CS231957B2 (fr)
CY (1)	CY1045A (fr)
DD (1)	DD122684A5 (fr)
DE (1)	DE2550111C2 (fr)
DK (1)	DK141098B (fr)
FI (1)	FI60707C (fr)
GB (1)	GB1468497A (fr)
HK (1)	HK19380A (fr)
HU (1)	HU173108B (fr)
IE (1)	IE41928B1 (fr)
IL (1)	IL48423A (fr)
LU (1)	LU73738A1 (fr)
NL (1)	NL177405C (fr)
NO (1)	NO143576C (fr)
OA (1)	OA05162A (fr)
PL (1)	PL101248B1 (fr)
SE (1)	SE407063B (fr)
SU (2)	SU673173A3 (fr)
YU (2)	YU39583B (fr)

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Publication number	Priority date	Publication date	Assignee	Title
FR1312427A (fr) *	1961-04-12	1962-12-21	Science Union Et Compagnie Soc	Nouveaux dérivés de la pipérazine et leurs préparations
FR2101081B1 (fr) *	1970-08-19	1974-01-11	Rhone Poulenc Sa
BE790408A (fr) *	1971-10-22	1973-04-20	Rhone Poulenc Sa	Nouveaux derives de la pyrrolo (3,4-b) pyridine, leur preparation et les compositions medicinales qui les
OA04285A (fr) *	1972-01-07	1979-12-31	Rhone Poulenc Sa	Nouveaux dérivés de la pyrrolo (3,4-b) pyrazine et leur préparation.
BE793851A (fr) *	1972-01-10	1973-07-10	Rhone Poulenc Sa	Nouveaux derives de l'isoindoline, leur preparation et les compositions medicinales qui les contiennent
AR207555A1 (es) *	1972-12-04	1976-10-15		Procedimiento para preparar aril-6-piperazinocarboniloxi-5 oxo-7 tetrahidro-2,3,6,7 ditiino(1,4)(2,3-c)pirroles
OA04700A (fr) *	1973-05-15	1980-07-31	Rhone Poulenc Sa	Nouveaux dérivés de la naphtyridine et leur procédé de préparation.

1975
- 1975-01-01 AR AR261091A patent/AR208414A1/es active
- 1975-10-23 OA OA55663A patent/OA05162A/fr unknown
- 1975-10-30 NL NLAANVRAGE7512732,A patent/NL177405C/xx not_active IP Right Cessation
- 1975-11-03 CA CA238,909A patent/CA1057755A/fr not_active Expired
- 1975-11-05 AU AU86331/75A patent/AU503200B2/en not_active Expired
- 1975-11-05 HU HU75RO868A patent/HU173108B/hu unknown
- 1975-11-05 IE IE2414/75A patent/IE41928B1/en unknown
- 1975-11-05 DD DD189261A patent/DD122684A5/xx unknown
- 1975-11-05 IL IL48423A patent/IL48423A/xx unknown
- 1975-11-05 JP JP75132198A patent/JPS5422996B2/ja not_active Expired
- 1975-11-06 NO NO753713A patent/NO143576C/no unknown
- 1975-11-06 LU LU73738A patent/LU73738A1/xx unknown
- 1975-11-06 DK DK499275AA patent/DK141098B/da not_active IP Right Cessation
- 1975-11-06 CY CY1045A patent/CY1045A/xx unknown
- 1975-11-06 GB GB4610375A patent/GB1468497A/en not_active Expired
- 1975-11-06 SE SE7512477A patent/SE407063B/xx not_active IP Right Cessation
- 1975-11-06 SU SU752186208A patent/SU673173A3/ru active
- 1975-11-06 CH CH1437875A patent/CH609057A5/xx not_active IP Right Cessation
- 1975-11-06 BE BE161652A patent/BE835325A/fr not_active IP Right Cessation
- 1975-11-07 YU YU2815/75A patent/YU39583B/xx unknown
- 1975-11-07 FI FI753127A patent/FI60707C/fi not_active IP Right Cessation
- 1975-11-07 CS CS757510A patent/CS231957B2/cs unknown
- 1975-11-07 PL PL1975199797A patent/PL101248B1/pl unknown
- 1975-11-07 AT AT848675A patent/AT343123B/de not_active IP Right Cessation
- 1975-11-07 DE DE2550111A patent/DE2550111C2/de not_active Expired
1976
- 1976-07-02 AR AR263835A patent/AR208800A1/es active
- 1976-08-02 SU SU762385529A patent/SU604496A3/ru active
1977
- 1977-04-25 US US05/790,801 patent/US4220646A/en not_active Expired - Lifetime
- 1977-06-07 AT AT401977A patent/AT343666B/de not_active IP Right Cessation
- 1977-09-14 CS CS775983A patent/CS231958B2/cs unknown
1978
- 1978-10-13 JP JP12525778A patent/JPS5498790A/ja active Granted
1980
- 1980-04-10 HK HK193/80A patent/HK19380A/xx unknown
1982
- 1982-08-26 YU YU1921/82A patent/YU40087B/xx unknown

Also Published As

Publication number	Publication date
CY1045A (en)	1980-08-01
YU39583B (en)	1985-03-20
OA05162A (fr)	1981-01-31
IL48423A (en)	1979-03-12
SE7512477L (sv)	1976-05-10
JPS5498790A (en)	1979-08-03
DK499275A (fr)	1976-05-08
FI60707C (fi)	1982-03-10
JPS5422996B2 (fr)	1979-08-10
NL7512732A (nl)	1976-05-11
AR208414A1 (es)	1976-12-27
DE2550111A1 (de)	1976-05-13
DE2550111C2 (de)	1983-09-15
FI753127A7 (fr)	1976-05-08
NO143576B (no)	1980-12-01
AU8633175A (en)	1977-05-12
DK141098C (fr)	1980-07-07
LU73738A1 (fr)	1976-09-06
AT343123B (de)	1978-05-10
IL48423A0 (en)	1976-01-30
AT343666B (de)	1978-06-12
CS231958B2 (en)	1985-01-16
US4220646A (en)	1980-09-02
CS751075A2 (en)	1984-01-16
FI60707B (fi)	1981-11-30
CS231957B2 (en)	1985-01-16
JPS5170776A (fr)	1976-06-18
NO753713L (fr)	1976-05-10
SU604496A3 (ru)	1978-04-25
IE41928L (en)	1976-05-07
YU192182A (en)	1983-01-21
CS598377A2 (en)	1984-01-16
BE835325A (fr)	1976-05-06
NO143576C (no)	1981-03-11
ATA848675A (de)	1977-09-15
SE407063B (sv)	1979-03-12
AR208800A1 (es)	1977-02-28
IE41928B1 (en)	1980-04-23
HK19380A (en)	1980-04-18
NL177405C (nl)	1985-09-16
HU173108B (hu)	1979-02-28
JPS558508B2 (fr)	1980-03-04
CA1057755A (fr)	1979-07-03
NL177405B (nl)	1985-04-16
YU40087B (en)	1985-06-30
DD122684A5 (fr)	1976-10-20
YU281575A (en)	1983-01-21
SU673173A3 (ru)	1979-07-05
AU503200B2 (en)	1979-08-30
ATA401977A (de)	1977-10-15
CH609057A5 (fr)	1979-02-15
GB1468497A (en)	1977-03-30
PL101248B1 (pl)	1978-12-30

Legal Events

Date	Code	Title	Description
1989-07-10	PBP	Patent lapsed

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DE69921358T2 (de)	2006-03-09	Stickstoffhaltige heterobicyclen als faktor-xa-hemmer
AU2012322085B2 (en)	2017-05-04	Substituted tetrahydroisoquinoline compounds as factor Xia inhibitors
US4220646A (en)	1980-09-02	Heterocyclic compounds
DE60315062T2 (de)	2008-04-10	Triazolverbindungen zur behandlung von dysmenorrhoe
BR122017002949A2 (pt)	2019-09-10	amidas heterocíclicas como inibidores de quinases
WO2010047956A9 (fr)	2011-10-06	Antagonistes de récepteur-1 de l'hormone de mélano-concentration d'azolopyrrolone
MXPA02012895A (es)	2003-05-14	Derivados de pirazol condensado con 1-(heteroaril-fenil) como inhibidores del factor xa.
EP0353778A2 (fr)	1990-02-07	Dérivés de pyrrolo[1,4]benzodiazépine
EP2961746A1 (fr)	2016-01-06	Dérivés de phénylpyrazole en tant que puissants inhibiteurs de rock1 et rock2
ES2803659T3 (es)	2021-01-28	Inhibidores macrocíclicos del factor xia que contienen restos alquilo o cicloalquilo p2
KR102732405B1 (ko)	2024-11-20	파르네소이드 x 수용체 조정제로서의 알켄 스피로시클릭 화합물
US3389139A (en)	1968-06-18	6-homopiperazino and piperazinomorphanthridines
JPS62149662A (ja)	1987-07-03	Ｎ−含有複素環化合物
CN114874222B (zh)	2025-06-06	携带非芳族p2,基团的因子xia新大环
EP0003016A1 (fr)	1979-07-25	Dérivés de la pyrazino-benzoxazépine et -benzothiazépine, leurs procédés de préparation et compositions pharmaceutiques les contenant
FI61872C (fi)	1982-10-11	Derivat av trijoderade aminobensenkarboxylsyror anvaenda som roentgenkontrastmedel
WO2004002406A2 (fr)	2004-01-08	Pyrimidinones bicycliques inhibiteurs de la cascade de coagulation
CA3210102A1 (fr)	2022-09-09	Derives de diazepine utiles dans le traitement de clostridium difficile
Goncharov et al.	2017	Reaction of N-(3-oxoalkenyl) chloroacetamides with sodium p-toluenesulfinate–synthesis of 3-tosylpyridin-2 (1 Н)-ones
NO144019B (no)	1981-02-23	Analogifremgangsmaate for fremstilling av terapeutisk aktive naftyridinderivater
NO811376L (no)	1981-10-26	Fremgangsmaate ved fremstilling av antihypertensive lactamer
SU856386A3 (ru)	1981-08-15	Способ получени производных 1,4-дитиепино-[2,3- ПИРРОЛА ИЛИ ИХ СОЛЕЙ
JPH04128291A (ja)	1992-04-28	新規なヘテロ環化合物およびその製造法
GB2356198A (en)	2001-05-16	Isoxazole thrombin receptor antagonists