DE2008692A1 - Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue Verbindungen - Google Patents
Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue VerbindungenInfo
- Publication number
- DE2008692A1 DE2008692A1 DE19702008692 DE2008692A DE2008692A1 DE 2008692 A1 DE2008692 A1 DE 2008692A1 DE 19702008692 DE19702008692 DE 19702008692 DE 2008692 A DE2008692 A DE 2008692A DE 2008692 A1 DE2008692 A1 DE 2008692A1
- Authority
- DE
- Germany
- Prior art keywords
- indole
- carboxylic acid
- deep
- group
- acid
- 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.)
- Pending
Links
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title description 14
- -1 alkoxy radical Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- MUFSVCLYKZROLW-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-indole-3-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2C(C(=O)O)=CNC2=C1 MUFSVCLYKZROLW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- WGBRWCPAKNJFLM-UHFFFAOYSA-N 2-cyano-2-(2-nitrophenyl)acetic acid Chemical class OC(=O)C(C#N)C1=CC=CC=C1[N+]([O-])=O WGBRWCPAKNJFLM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- JFJPBRVVIYIRDB-UHFFFAOYSA-N 2-(2-aminophenyl)-2-cyanoacetic acid Chemical class NC1=C(C=CC=C1)C(C(=O)O)C#N JFJPBRVVIYIRDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- LOPPIPLZGUYXJD-UHFFFAOYSA-N 6-amino-1h-indole-3-carboxylic acid Chemical compound NC1=CC=C2C(C(O)=O)=CNC2=C1 LOPPIPLZGUYXJD-UHFFFAOYSA-N 0.000 claims description 3
- LPBGVZVDBKMWFS-UHFFFAOYSA-N 6-methoxy-1h-indole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=CNC2=C1 LPBGVZVDBKMWFS-UHFFFAOYSA-N 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- PHHZCIOPSFQASN-UHFFFAOYSA-N 6-methyl-1h-indole-3-carboxylic acid Chemical compound CC1=CC=C2C(C(O)=O)=CNC2=C1 PHHZCIOPSFQASN-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- RIEPUMJCURGSOB-UHFFFAOYSA-N 2-cyano-2-[2-nitro-4-(trifluoromethyl)phenyl]acetic acid Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)C(F)(F)F)C(C(=O)O)C#N RIEPUMJCURGSOB-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 3
- MATJPVGBSAQWAC-UHFFFAOYSA-N 2-cyano-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC#N MATJPVGBSAQWAC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
- PVNVYFNJBRZZGZ-UHFFFAOYSA-N 2-cyano-2-(4-methoxy-2-nitrophenyl)acetic acid Chemical compound C(#N)C(C(=O)O)C1=C(C=C(C=C1)OC)[N+](=O)[O-] PVNVYFNJBRZZGZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
- XNJAYQHWXYJBBD-UHFFFAOYSA-N 1,4-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1F XNJAYQHWXYJBBD-UHFFFAOYSA-N 0.000 description 1
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
- HISHUMDTGXICEZ-UHFFFAOYSA-N 1-chloro-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Cl)C([N+]([O-])=O)=C1 HISHUMDTGXICEZ-UHFFFAOYSA-N 0.000 description 1
- DUDZAZPWJFTDPV-UHFFFAOYSA-N 1735-91-7 Chemical compound OC(=O)CC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O DUDZAZPWJFTDPV-UHFFFAOYSA-N 0.000 description 1
- KCNISYPADDTFDO-UHFFFAOYSA-N 2,4-dinitrophenylacetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O KCNISYPADDTFDO-UHFFFAOYSA-N 0.000 description 1
- RQQGKHZHIROOGO-UHFFFAOYSA-N 2-(2,6-dinitrophenyl)acetic acid Chemical compound OC(=O)CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O RQQGKHZHIROOGO-UHFFFAOYSA-N 0.000 description 1
- KTHGBTRAQOAOBS-UHFFFAOYSA-N 2-(2-chloro-6-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=C(Cl)C=CC=C1[N+]([O-])=O KTHGBTRAQOAOBS-UHFFFAOYSA-N 0.000 description 1
- WWZXCZMODVFKSK-UHFFFAOYSA-N 2-(2-methoxy-6-nitrophenyl)acetic acid Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CC(O)=O WWZXCZMODVFKSK-UHFFFAOYSA-N 0.000 description 1
- FLZUSUKBKOZJLG-UHFFFAOYSA-N 2-(4-chloro-2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1[N+]([O-])=O FLZUSUKBKOZJLG-UHFFFAOYSA-N 0.000 description 1
- DXXWGXHJDCZCSN-UHFFFAOYSA-N 2-(4-methyl-2-nitrophenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C([N+]([O-])=O)=C1 DXXWGXHJDCZCSN-UHFFFAOYSA-N 0.000 description 1
- PYJHXGBGSPGUMI-UHFFFAOYSA-N 2-cyano-2-(2,4-dinitrophenyl)acetic acid Chemical compound C(#N)C(C(=O)O)C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-] PYJHXGBGSPGUMI-UHFFFAOYSA-N 0.000 description 1
- IJSJJEBIRSSHFS-UHFFFAOYSA-N 2-cyano-2-(5-methoxy-2-nitrophenyl)acetic acid Chemical compound COC1=CC=C([N+]([O-])=O)C(C(C#N)C(O)=O)=C1 IJSJJEBIRSSHFS-UHFFFAOYSA-N 0.000 description 1
- TUUCAVHDDJJYMX-UHFFFAOYSA-N 2-cyano-2-[2-nitro-4-(trifluoromethyl)phenyl]-n-phenylacetamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1C(C#N)C(=O)NC1=CC=CC=C1 TUUCAVHDDJJYMX-UHFFFAOYSA-N 0.000 description 1
- XCTQPMCULSZKLT-UHFFFAOYSA-N 2-cyano-n-phenylacetamide Chemical compound N#CCC(=O)NC1=CC=CC=C1 XCTQPMCULSZKLT-UHFFFAOYSA-N 0.000 description 1
- XCGMUHYKYLADKO-UHFFFAOYSA-N 20876-30-6 Chemical compound COC1=CC=C(CC(O)=O)C([N+]([O-])=O)=C1 XCGMUHYKYLADKO-UHFFFAOYSA-N 0.000 description 1
- ITDFSNLFIZWJDB-UHFFFAOYSA-N 6-fluoro-1h-indole-3-carboxylic acid Chemical compound FC1=CC=C2C(C(=O)O)=CNC2=C1 ITDFSNLFIZWJDB-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6904964A FR2034217A1 (en) | 1969-02-26 | 1969-02-26 | Indol-3-carboxylic acid derivatives |
| FR7005895A FR2080854A6 (en) | 1970-02-19 | 1970-02-19 | Indol-3-carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2008692A1 true DE2008692A1 (de) | 1970-09-17 |
Family
ID=26214862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702008692 Pending DE2008692A1 (de) | 1969-02-26 | 1970-02-25 | Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue Verbindungen |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH510017A (enrdf_load_stackoverflow) |
| DE (1) | DE2008692A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1305458A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993025524A1 (en) * | 1992-06-05 | 1993-12-23 | Shell Internationale Research Maatschappij B.V. | Fungicidal indole derivatives |
| WO1998006715A1 (en) * | 1996-08-09 | 1998-02-19 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
| WO1999041239A1 (en) * | 1998-02-10 | 1999-08-19 | Novartis Ag | B cell inhibitors |
| WO2000051431A1 (de) * | 1999-03-02 | 2000-09-08 | Basf Aktiengesellschaft | Verwendung von phenylessigsaüreamide als pflanzenschutzmittel mit herbizider und fungizider wirkung |
| EP2392571A3 (en) * | 2005-07-29 | 2012-03-14 | F. Hoffmann-La Roche AG | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL150651A0 (en) * | 2000-01-20 | 2003-02-12 | Eisai Co Ltd | Nitrogen-containing cyclic compound and pharmaceutical compositions containing the same |
| US7875605B2 (en) | 2002-11-28 | 2011-01-25 | Suven Life Sciences Limited | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
-
1970
- 1970-02-20 GB GB833070A patent/GB1305458A/en not_active Expired
- 1970-02-23 CH CH258470A patent/CH510017A/fr not_active IP Right Cessation
- 1970-02-25 DE DE19702008692 patent/DE2008692A1/de active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993025524A1 (en) * | 1992-06-05 | 1993-12-23 | Shell Internationale Research Maatschappij B.V. | Fungicidal indole derivatives |
| MD1743B2 (ro) * | 1992-06-05 | 2001-09-30 | Shell Internationale Research Maatschappij B.V. | Derivaţi ai indolului, procedeu de obţinere a lor, compoziţie fungicidă şi procedeu de combatere a fungilor |
| WO1998006715A1 (en) * | 1996-08-09 | 1998-02-19 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
| WO1999041239A1 (en) * | 1998-02-10 | 1999-08-19 | Novartis Ag | B cell inhibitors |
| WO2000051431A1 (de) * | 1999-03-02 | 2000-09-08 | Basf Aktiengesellschaft | Verwendung von phenylessigsaüreamide als pflanzenschutzmittel mit herbizider und fungizider wirkung |
| EP2392571A3 (en) * | 2005-07-29 | 2012-03-14 | F. Hoffmann-La Roche AG | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1305458A (enrdf_load_stackoverflow) | 1973-01-31 |
| CH510017A (fr) | 1971-07-15 |
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