CH614209A5 - Process for the preparation of new heterocyclic compounds - Google Patents

Process for the preparation of new heterocyclic compounds

Info

Publication number: CH614209A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; atoms; chloro; naphthyridine; alkyl
Prior art date: 1975-04-07

Application number

CH1212178A

Other languages

English (en)

French (fr)

Inventor

Claude Cotrel

Cornel Crisan

Claude Jeanmart

Andre Leger

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.)

1975-04-07

Filing date

1976-04-06

Publication date

1979-11-15

1975-04-07 Priority claimed from FR7510756A external-priority patent/FR2321290A1/fr

1976-02-11 Priority claimed from FR7603774A external-priority patent/FR2340731A1/fr

1976-02-11 Priority claimed from FR7603773A external-priority patent/FR2340733A2/fr

1976-04-06 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1979-11-15 Publication of CH614209A5 publication Critical patent/CH614209A5/fr

Links

238000000034 method Methods 0.000 title claims description 25
150000002391 heterocyclic compounds Chemical class 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 9
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims abstract description 12
125000005842 heteroatom Chemical group 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
239000012948 isocyanate Substances 0.000 claims abstract description 5
150000002513 isocyanates Chemical class 0.000 claims abstract description 5
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 84
125000000217 alkyl group Chemical group 0.000 claims description 18
ZMJIPNACONXBCG-UHFFFAOYSA-N 7h-pyrrolo[3,4-b]pyrazine Chemical compound C1=CN=C2CN=CC2=N1 ZMJIPNACONXBCG-UHFFFAOYSA-N 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 12
PVAYDHNYGBSSMW-UHFFFAOYSA-N 5h-pyrrolo[3,4-b]pyridine Chemical compound C1=CC=C2CN=CC2=N1 PVAYDHNYGBSSMW-UHFFFAOYSA-N 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
150000003236 pyrrolines Chemical class 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 5
125000001422 pyrrolinyl group Chemical group 0.000 abstract description 4
229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
239000001961 anticonvulsive agent Substances 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract 3
GSIQLKOFXMCKNK-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine Chemical compound C1=CN=C2CNCC2=N1 GSIQLKOFXMCKNK-UHFFFAOYSA-N 0.000 abstract 1
SJMNQXLXIIXDDS-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-b]pyridine Chemical compound C1=CC=C2CNCC2=N1 SJMNQXLXIIXDDS-UHFFFAOYSA-N 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
230000001622 hypnogenic effect Effects 0.000 abstract 1
125000000168 pyrrolyl group Chemical group 0.000 abstract 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
125000001302 tertiary amino group Chemical group 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
238000001914 filtration Methods 0.000 description 50
238000002844 melting Methods 0.000 description 48
230000008018 melting Effects 0.000 description 48
239000000047 product Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 29
239000000243 solution Substances 0.000 description 28
-1 alkyl radicals Chemical class 0.000 description 25
238000010992 reflux Methods 0.000 description 25
239000002244 precipitate Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
238000001816 cooling Methods 0.000 description 13
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
238000001035 drying Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
238000010438 heat treatment Methods 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
229910052753 mercury Inorganic materials 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
238000010908 decantation Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000011591 potassium Substances 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
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 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
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 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
CRADWWWVIYEAFR-UHFFFAOYSA-N 1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N)=CC=C21 CRADWWWVIYEAFR-UHFFFAOYSA-N 0.000 description 3
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 3
VNLYHYHJIXGBFX-UHFFFAOYSA-N 4-(trifluoromethyl)phthalic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1C(O)=O VNLYHYHJIXGBFX-UHFFFAOYSA-N 0.000 description 3
AKAAHMXNWDUFTD-UHFFFAOYSA-N 5-(trifluoromethyl)-2-benzofuran-1,3-dione Chemical compound FC(F)(F)C1=CC=C2C(=O)OC(=O)C2=C1 AKAAHMXNWDUFTD-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
FVVIVIPXASZNGB-UHFFFAOYSA-N methyl 2-cyano-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C=C1C#N FVVIVIPXASZNGB-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
WRTSXKKAXLYBSH-UHFFFAOYSA-N trifluoromethyl benzoate Chemical compound FC(F)(F)OC(=O)C1=CC=CC=C1 WRTSXKKAXLYBSH-UHFFFAOYSA-N 0.000 description 3
BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 2
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 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
229910000397 disodium phosphate Inorganic materials 0.000 description 2
235000019800 disodium phosphate Nutrition 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 2
150000003949 imides Chemical class 0.000 description 2
XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 2
OSWBZCCZJXCOGL-UHFFFAOYSA-N n,n-dibutylcarbamoyl chloride Chemical compound CCCCN(C(Cl)=O)CCCC OSWBZCCZJXCOGL-UHFFFAOYSA-N 0.000 description 2
OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 2
CHGVIQWWXDOWRN-UHFFFAOYSA-N n-butyl-n-methylcarbamoyl chloride Chemical compound CCCCN(C)C(Cl)=O CHGVIQWWXDOWRN-UHFFFAOYSA-N 0.000 description 2
XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 2
OCDPLMCWDJXNTG-UHFFFAOYSA-N n-methyl-n-pentylcarbamoyl chloride Chemical compound CCCCCN(C)C(Cl)=O OCDPLMCWDJXNTG-UHFFFAOYSA-N 0.000 description 2
YEMRRHHMLASGRQ-UHFFFAOYSA-N n-methyl-n-propylcarbamoyl chloride Chemical compound CCCN(C)C(Cl)=O YEMRRHHMLASGRQ-UHFFFAOYSA-N 0.000 description 2
UOIWOHLIGKIYFE-UHFFFAOYSA-N n-methylpentan-1-amine Chemical compound CCCCCNC UOIWOHLIGKIYFE-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
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 2
150000003512 tertiary amines Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
UNLVJVQEDSDPIN-UHFFFAOYSA-N 2-amino-3-(trifluoromethyl)benzoic acid Chemical compound NC1=C(C(O)=O)C=CC=C1C(F)(F)F UNLVJVQEDSDPIN-UHFFFAOYSA-N 0.000 description 1
NQTLZJODEOHALT-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)benzoic acid Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(O)=O NQTLZJODEOHALT-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
241001279009 Strychnos toxifera Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229950005228 bromoform Drugs 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
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000012043 crude product Substances 0.000 description 1
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000004907 flux Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZGONRPXUNVTWTA-UHFFFAOYSA-N methyl 2-isocyanatoacetate Chemical compound COC(=O)CN=C=O ZGONRPXUNVTWTA-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical group CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation

Landscapes

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

CH1212178A 1975-04-07 1976-04-06 Process for the preparation of new heterocyclic compounds CH614209A5 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR7510756A FR2321290A1 (fr)	1975-04-07	1975-04-07	Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent
FR7603774A FR2340731A1 (fr)	1976-02-11	1976-02-11	Nouveaux composes heterocycliques, leur preparation et les compositions qui les contiennent
FR7603773A FR2340733A2 (fr)	1976-02-11	1976-02-11	Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent

Publications (1)

Publication Number	Publication Date
CH614209A5 true CH614209A5 (en)	1979-11-15

Family

ID=27250439

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH430576A CH613453A5 (xx)	1975-04-07	1976-04-06
CH1212178A CH614209A5 (en)	1975-04-07	1976-04-06	Process for the preparation of new heterocyclic compounds

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH430576A CH613453A5 (xx)	1975-04-07	1976-04-06

Country Status (29)

Country	Link
US (1)	US4086348A (xx)
JP (1)	JPS51122094A (xx)
AR (3)	AR214286A1 (xx)
AT (1)	AT348524B (xx)
CA (1)	CA1072957A (xx)
CH (2)	CH613453A5 (xx)
CS (3)	CS186747B2 (xx)
CY (1)	CY1085A (xx)
DD (1)	DD123605A5 (xx)
DE (1)	DE2615067A1 (xx)
DK (1)	DK162976A (xx)
ES (2)	ES446762A1 (xx)
FI (1)	FI60012C (xx)
GB (1)	GB1483996A (xx)
HK (1)	HK54580A (xx)
HU (1)	HU176315B (xx)
IE (1)	IE42973B1 (xx)
IL (1)	IL49344A (xx)
LU (1)	LU74703A1 (xx)
MX (1)	MX3138E (xx)
NL (1)	NL7603307A (xx)
NO (1)	NO144019C (xx)
OA (1)	OA05287A (xx)
PH (1)	PH14015A (xx)
PL (3)	PL100184B1 (xx)
PT (1)	PT64976B (xx)
SE (2)	SE7604044L (xx)
SU (3)	SU648102A3 (xx)
YU (3)	YU86976A (xx)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1265803A (fr) *	1985-07-11	1990-02-13	Claude Cotrel	Amides substitues, leur preparation et les medicaments qui les contiennent
DE10042093A1 (de) *	2000-08-26	2002-03-07	Dresden Arzneimittel	Antikonvulsiv wirkende 6,7-Dihydro-pyrrolo[3,4-d]pyridin-5-one und Verfahren zu deren Darstellung
PL376890A1 (pl)	2002-11-26	2006-01-09	Maruishi Pharmaceutical Co., Ltd.	Pochodne izoindoliny
WO2007080430A1 (en) *	2006-01-16	2007-07-19	Generics [Uk] Limited	Novel process
EP2948147B1 (en) *	2013-01-28	2019-03-13	H. Lundbeck A/S	N-substituted-5-substituted phthalamic acids as sortilin inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
OA04700A (fr) *	1973-05-15	1980-07-31	Rhone Poulenc Sa	Nouveaux dérivés de la naphtyridine et leur procédé de préparation.

1976
- 1976-03-26 OA OA55782A patent/OA05287A/xx unknown
- 1976-03-30 NL NL7603307A patent/NL7603307A/xx not_active Application Discontinuation
- 1976-03-31 CS CS7700002623A patent/CS186747B2/cs unknown
- 1976-03-31 CS CS7600002084A patent/CS186734B2/cs unknown
- 1976-03-31 CS CS7700002624A patent/CS186748B2/cs unknown
- 1976-04-05 IL IL49344A patent/IL49344A/xx unknown
- 1976-04-05 CA CA249,577A patent/CA1072957A/fr not_active Expired
- 1976-04-05 US US05/673,868 patent/US4086348A/en not_active Expired - Lifetime
- 1976-04-05 JP JP51038103A patent/JPS51122094A/ja active Granted
- 1976-04-05 GB GB13703/76A patent/GB1483996A/en not_active Expired
- 1976-04-05 DD DD192209A patent/DD123605A5/xx unknown
- 1976-04-05 CY CY1085A patent/CY1085A/xx unknown
- 1976-04-05 PH PH18289A patent/PH14015A/en unknown
- 1976-04-05 IE IE704/76A patent/IE42973B1/en unknown
- 1976-04-06 LU LU74703A patent/LU74703A1/xx unknown
- 1976-04-06 SE SE7604044D patent/SE7604044L/xx not_active Application Discontinuation
- 1976-04-06 CH CH430576A patent/CH613453A5/xx not_active IP Right Cessation
- 1976-04-06 PT PT64976A patent/PT64976B/pt unknown
- 1976-04-06 NO NO761168A patent/NO144019C/no unknown
- 1976-04-06 CH CH1212178A patent/CH614209A5/fr not_active IP Right Cessation
- 1976-04-06 YU YU00869/76A patent/YU86976A/xx unknown
- 1976-04-06 DK DK162976A patent/DK162976A/da not_active IP Right Cessation
- 1976-04-06 MX MX14476U patent/MX3138E/es unknown
- 1976-04-06 SU SU762339152A patent/SU648102A3/ru active
- 1976-04-06 SE SE7604044A patent/SE421793B/xx not_active IP Right Cessation
- 1976-04-07 PL PL1976188560A patent/PL100184B1/pl unknown
- 1976-04-07 AR AR262814A patent/AR214286A1/es active
- 1976-04-07 PL PL1976202792A patent/PL100988B1/pl unknown
- 1976-04-07 HU HU76RO886A patent/HU176315B/hu unknown
- 1976-04-07 ES ES446762A patent/ES446762A1/es not_active Expired
- 1976-04-07 AT AT249776A patent/AT348524B/de not_active IP Right Cessation
- 1976-04-07 PL PL1976202791A patent/PL100987B1/pl unknown
- 1976-04-07 DE DE19762615067 patent/DE2615067A1/de not_active Ceased
- 1976-04-07 FI FI760937A patent/FI60012C/fi not_active IP Right Cessation
- 1976-06-14 ES ES448847A patent/ES448847A1/es not_active Expired
- 1976-09-28 AR AR264893A patent/AR213739A1/es active
- 1976-09-30 AR AR264924A patent/AR214055A1/es active
1977
- 1977-04-21 SU SU772473622A patent/SU637082A3/ru active
- 1977-04-21 SU SU772473623A patent/SU638258A3/ru active
1980
- 1980-09-25 HK HK545/80A patent/HK54580A/xx unknown
1982
- 1982-06-15 YU YU01305/82A patent/YU130582A/xx unknown
- 1982-06-15 YU YU01304/82A patent/YU130482A/xx unknown

Also Published As

Publication number	Publication date
HK54580A (en)	1980-10-03
YU130582A (en)	1983-02-28
JPS62149B2 (xx)	1987-01-06
IL49344A (en)	1979-05-31
ES448847A1 (es)	1977-10-01
AT348524B (de)	1979-02-26
NO761168L (xx)	1976-10-08
AR213739A1 (es)	1979-03-15
DK162976A (da)	1976-10-08
FI760937A (xx)	1976-10-08
IL49344A0 (en)	1976-06-30
AR214055A1 (es)	1979-04-30
MX3138E (es)	1980-05-06
SU638258A3 (ru)	1978-12-15
FI60012B (fi)	1981-07-31
US4086348A (en)	1978-04-25
PL100987B1 (pl)	1978-11-30
OA05287A (fr)	1981-02-28
IE42973B1 (en)	1980-11-19
NO144019C (no)	1981-06-03
NO144019B (no)	1981-02-23
PL100988B1 (pl)	1978-11-30
SE7604044L (sv)	1976-10-08
ATA249776A (de)	1978-07-15
PH14015A (en)	1980-12-08
JPS51122094A (en)	1976-10-25
ES446762A1 (es)	1977-06-01
LU74703A1 (xx)	1977-02-02
FI60012C (fi)	1981-11-10
CA1072957A (fr)	1980-03-04
SE421793B (sv)	1982-02-01
YU130482A (en)	1983-02-28
DE2615067A1 (de)	1976-10-28
DD123605A5 (xx)	1977-01-05
CS186747B2 (en)	1978-12-29
YU86976A (en)	1983-02-28
SU637082A3 (ru)	1978-12-05
PL100184B1 (pl)	1978-09-30
CY1085A (en)	1980-12-27
PT64976B (fr)	1977-09-07
CS186734B2 (en)	1978-12-29
CH613453A5 (xx)	1979-09-28
CS186748B2 (en)	1978-12-29
PT64976A (fr)	1976-05-01
IE42973L (en)	1976-10-07
HU176315B (en)	1981-01-28
GB1483996A (en)	1977-08-24
NL7603307A (nl)	1976-10-11
SU648102A3 (ru)	1979-02-15
AR214286A1 (es)	1979-05-31
AU1267476A (en)	1977-10-13

Legal Events

Date	Code	Title	Description
1987-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0432040B1 (fr)	1994-07-27	Dérivés hétérocycliques d'acylaminothiazoles, leur préparation et compositions pharmaceutiques en contenant
FR2676443A1 (fr)	1992-11-20	Nouveaux derives de perhydroisoindole et leur preparation.
CA2030570A1 (fr)	1991-05-24	Derives de l'isoindolone et leur preparation
CA2104883A1 (fr)	1994-02-28	Derives d'acide thienyl ou pyrrolyl carboxyliques, leur preparation et medicaments les contenant
EP0267111A1 (fr)	1988-05-11	Imidazopyridines, leur préparation et leur application en thérapeutique
CH618699A5 (xx)	1980-08-15
EP0147317A2 (fr)	1985-07-03	Nouveaux dérivés ortho-condensés du pyrrole, leur préparation et les médicaments qui les contiennent
CH614209A5 (en)	1979-11-15	Process for the preparation of new heterocyclic compounds
EP0115979A1 (fr)	1984-08-15	Nouveaux dérivés du 1H,3H-pyrrolo (1,2-c) thiazole leur préparation et les médicaments qui les contiennent
FR2468370A1 (fr)	1981-05-08	Nouvelles pyridothienotriazines et leur procede de preparation
CH661507A5 (fr)	1987-07-31	Derives de l'hydroxymethyl-5 oxazolidinone-2 n-arylee et leur procede de preparation.
CA1187879A (fr)	1985-05-28	Acylamino-4 aza-1 adamantanes, procede pour leur preparation et application en therapeutique
EP0124384B1 (fr)	1987-08-05	Nouveaux dérivés du pyrrole orthocondensé utiles pour la préparation de nouveaux médicaments et leur préparation
CA1091674A (fr)	1980-12-16	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent
FR2719843A1 (fr)	1995-11-17	Dérivés de 5,6-dihydro-4h-imidazo [2',1':2,3] imidazo-[4,5,1-ij] quinoléine et de 4,5-dihydroimidazo [1,2-a] pyrrolo-[1,2,3-cd] benzimidazole, leur préparation et leur application en thérapeutique.
FR2462429A1 (fr)	1981-02-13	Procede pour la preparation des 7-alcoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phtalazones et de leurs intermediaires et produits ainsi obtenus
EP0384843B1 (fr)	1994-08-31	Dérivés de la 1-arylsulfonyl 2-pipéridinone, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
EP0197230B1 (fr)	1990-01-31	Imidazo /1,2-a/ pyrimidines et leurs sels avec les acides, procédé et intermédiaires de préparation, application comme médicaments et compositions les renfermant
CA1073912A (fr)	1980-03-18	Derives de la dibenzo (de,h) quinoleine, leur preparation et les compositions qui les contiennent
EP0238411A1 (fr)	1987-09-23	Dihydro-1,2 méthyl-4 oxo-1 5-H pyrido (4,3-b) indoles et leur procédé de synthèse
EP0334289B1 (de)	1993-06-16	Heterocyclisch substituierte 5,7-Dihydro-pyrrolo[3,2-f]benzoxazol-6-one, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel
US4570001A (en)	1986-02-11	Process for synthesizing certain N-benzoylamino indolines
CH629198A5 (fr)	1982-04-15	Procede de preparation de nouveaux 2,3-alkylene-bis (oxy)-benzamides substitues.
CH609695A5 (en)	1979-03-15	Process for the preparation of new heterocyclic compounds