FR652M - Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels. - Google Patents
Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels. Download PDFInfo
- Publication number
- FR652M FR652M FR838483A FR838483A FR652M FR 652 M FR652 M FR 652M FR 838483 A FR838483 A FR 838483A FR 838483 A FR838483 A FR 838483A FR 652 M FR652 M FR 652M
- Authority
- FR
- France
- Prior art keywords
- indole
- phenyl
- groups
- methyl
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 150000003839 salts Chemical class 0.000 title claims description 6
- 150000002475 indoles Chemical class 0.000 title claims description 5
- 239000002547 new drug Substances 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- XZNGTBLWFCRXKR-UHFFFAOYSA-N 3-phenyl-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1C1=CC=CC=C1 XZNGTBLWFCRXKR-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229940095064 tartrate Drugs 0.000 claims description 3
- -1 1- (1'-methyl-2'-dimethylaminoethyl) -3-phenyl-indole hydrochloride Chemical compound 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- GFPJLZASIVURDY-UHFFFAOYSA-N (3-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1 GFPJLZASIVURDY-UHFFFAOYSA-N 0.000 claims 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims 1
- POIVWEXWFKSJHL-UHFFFAOYSA-N 2-(dimethylamino)propan-2-ol Chemical compound CN(C)C(C)(C)O POIVWEXWFKSJHL-UHFFFAOYSA-N 0.000 claims 1
- OFBUPSNPSADROC-UHFFFAOYSA-N CC=1NC2=CC(=CC=C2C=1C1=CC=CC=C1)Cl Chemical compound CC=1NC2=CC(=CC=C2C=1C1=CC=CC=C1)Cl OFBUPSNPSADROC-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 238000006683 Mannich reaction Methods 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims 1
- 229920001592 potato starch Polymers 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 12
- 230000000202 analgesic effect Effects 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 229960004126 codeine Drugs 0.000 description 6
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- IKPQAFLAPZFWEG-UHFFFAOYSA-N 2-chloro-3-phenyl-1H-indole Chemical compound ClC=1NC2=CC=CC=C2C1C1=CC=CC=C1 IKPQAFLAPZFWEG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 2
- FLOZFGKBZCCIHS-UHFFFAOYSA-N 2-methyl-3-phenyl-1h-indole Chemical compound CC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 FLOZFGKBZCCIHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- 229960004415 codeine phosphate Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229960005141 piperazine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000552 rheumatic effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- GSSOUQZDEUORCA-UHFFFAOYSA-N 3-(6-chloro-2-methyl-3-phenylindol-1-yl)-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCCN1C(C)=C(C2=CC=C(Cl)C=C12)C1=CC=CC=C1 GSSOUQZDEUORCA-UHFFFAOYSA-N 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- SSFFIPZNEBLYPP-UHFFFAOYSA-N C(C)N(CCN1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C)CC Chemical compound C(C)N(CCN1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C)CC SSFFIPZNEBLYPP-UHFFFAOYSA-N 0.000 description 1
- ZYXRHWRXMAHFGQ-UHFFFAOYSA-N CC(CN(C)C)N(C=C(C1=C2)C3=CC=CC=C3)C1=CC=C2OC Chemical compound CC(CN(C)C)N(C=C(C1=C2)C3=CC=CC=C3)C1=CC=C2OC ZYXRHWRXMAHFGQ-UHFFFAOYSA-N 0.000 description 1
- PERIJGZCAYQMPV-UHFFFAOYSA-N CC(CN(C)C)N1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C Chemical compound CC(CN(C)C)N1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C PERIJGZCAYQMPV-UHFFFAOYSA-N 0.000 description 1
- UFDKVARIUXRGHX-UHFFFAOYSA-N CC(CN(C)C)N1C(C2=CC=CC=C2)=C(C)C2=CC=CC=C12 Chemical compound CC(CN(C)C)N1C(C2=CC=CC=C2)=C(C)C2=CC=CC=C12 UFDKVARIUXRGHX-UHFFFAOYSA-N 0.000 description 1
- LNERDIQOPWXVRO-UHFFFAOYSA-N CC(CN(C)C)N1C2=CC=CC=C2C(C2=CC(Cl)=CC=C2)=C1 Chemical compound CC(CN(C)C)N1C2=CC=CC=C2C(C2=CC(Cl)=CC=C2)=C1 LNERDIQOPWXVRO-UHFFFAOYSA-N 0.000 description 1
- JFHJWJPATWAWRV-UHFFFAOYSA-N CCOC(C=CC=C12)=C1N(C(C)CN(C)C)C=C2C1=CC=CC=C1 Chemical compound CCOC(C=CC=C12)=C1N(C(C)CN(C)C)C=C2C1=CC=CC=C1 JFHJWJPATWAWRV-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- VONRYSNFLFAPHO-UHFFFAOYSA-N N,N-diethyl-2-(2-methyl-3-phenylindol-1-yl)propan-1-amine Chemical compound CC(CN(CC)CC)N1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C VONRYSNFLFAPHO-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Chemical group 0.000 description 1
- 239000002184 metal Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK326559AA DK96884C (da) | 1959-09-14 | 1959-09-14 | Fremgangsmåde til fremstilling af indolderivater eller salte heraf. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR652M true FR652M (fr) | 1961-06-19 |
Family
ID=8120951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR838483A Expired FR652M (fr) | 1959-09-14 | 1960-09-13 | Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels. |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE595038A (da) |
| CH (1) | CH398595A (da) |
| DK (1) | DK96884C (da) |
| FR (1) | FR652M (da) |
| GB (1) | GB959203A (da) |
| NL (1) | NL113675C (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460296A1 (fr) * | 1979-06-29 | 1981-01-23 | Sandoz Sa | Nouvelles 1-aminoalkyl-3-phenyl-indolines, leur preparation et leur application comme medicaments |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3429886A (en) * | 1964-11-11 | 1969-02-25 | Ciba Geigy Corp | 1-tertiaryaminoalkyl-3-(4-pyridyl)-indoles |
| DE2931323A1 (de) * | 1979-08-02 | 1981-02-26 | Kali Chemie Pharma Gmbh | Neue n-aminoalkylindol-derivate und ihre salze |
| US6265403B1 (en) * | 1999-01-20 | 2001-07-24 | Merck & Co., Inc. | Angiogenesis inhibitors |
| CN105218426A (zh) * | 2014-06-17 | 2016-01-06 | 中国科学院兰州化学物理研究所 | 一种高效合成吲哚和异喹啉衍生物的方法 |
-
1959
- 1959-09-14 DK DK326559AA patent/DK96884C/da active
-
1960
- 1960-09-12 GB GB31373/60A patent/GB959203A/en not_active Expired
- 1960-09-13 FR FR838483A patent/FR652M/fr not_active Expired
- 1960-09-13 CH CH1034060A patent/CH398595A/de unknown
- 1960-09-14 NL NL255890A patent/NL113675C/xx active
- 1960-09-14 BE BE595038A patent/BE595038A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460296A1 (fr) * | 1979-06-29 | 1981-01-23 | Sandoz Sa | Nouvelles 1-aminoalkyl-3-phenyl-indolines, leur preparation et leur application comme medicaments |
| FR2514352A1 (da) * | 1979-06-29 | 1983-04-15 | Sandoz Sa |
Also Published As
| Publication number | Publication date |
|---|---|
| DK96884C (da) | 1963-09-16 |
| NL113675C (nl) | 1967-05-16 |
| CH398595A (de) | 1966-03-15 |
| GB959203A (en) | 1964-05-27 |
| BE595038A (fr) | 1961-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR880002310B1 (ko) | 펜에탄올 아민류의 제조방법 | |
| CA1088939A (fr) | Medicaments derives de l'indole | |
| EP0371876A1 (fr) | Composés isoxazoles et isoxazolines à activité anticonvulsivante, procédé de préparation et compositions thérapeutiques les contenant | |
| FR2528038A2 (fr) | Derives de benzhydrylsulfinylacetamide et leur utilisation en therapeutique | |
| FR2500450A1 (fr) | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique | |
| CH637927A5 (fr) | Derives de 4-amino-5-alkylsulfonyl ortho-anisamides et leurs procedes de preparation. | |
| EP0233793B1 (fr) | Dérivés de la décahydroquinoléine, leur procédé de préparation, les intermédiaires de préparation, leur application à titre de médicaments et les compositions les renfermant | |
| FR2460919A1 (fr) | Amino-ethers oxydes, leur procede de preparation et leur application en therapeutique | |
| FR2510998A1 (fr) | Nouveaux derives amines de la pyridazine, leur procede de preparation et les medicaments, a action desinhibitrice, qui en comportent | |
| EP0522915A1 (fr) | Dérivés de pyrimidine-4-carboxamide, leur préparation et leur application en thérapeutique | |
| EP0073161B1 (fr) | Nouveaux dérivés de la pyrazine actifs sur le système nerveux central | |
| FR2493315A1 (fr) | Derive de piperazine, procede pour sa preparation et composition analgesique en contenant | |
| FR652M (fr) | Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels. | |
| CA2000091A1 (fr) | Derives de la benzoxazolinone, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
| LU82236A1 (fr) | 9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique | |
| EP0008249A2 (fr) | Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique | |
| FR2526434A1 (fr) | Nouveaux azepino-indoles, leur preparation et leur utilisation comme medicaments | |
| EP0024960A2 (fr) | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux | |
| CA2001686A1 (fr) | Nouveaux derives 1-azabicycloalkanes, leur procede de preparation et leur application comme medicaments | |
| FR2495470A1 (fr) | Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol | |
| EP0135406B1 (fr) | Pyrrolidinones actives sur le système nerveux central, leur procédé de préparation, les médicaments en contenant | |
| CH658786A5 (fr) | Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters. | |
| EP0078765B1 (fr) | Dérivés de p-acylaminophénol à effet thérapeutique, procédé pour leur préparation, et composition à effet thérapeutique contenant lesdits dérivés à titre d'ingrédients pharmacologiquement actifs | |
| FR2462438A1 (fr) | Nouveaux derives de la 6-alkyl-7-phenyl-1,6-naphtyridine-5(6h)-one, leur preparation et leur application comme medicaments | |
| CA1223595A (fr) | Derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanamine et de (quinolyl-4)-1 (piperidyl-4)-3 propanamine, procedes pour leur preparation et medicaments les contenant |