CH557815A - Verfahren zur herstellung von 3-indol-aliphatischen saeuren. - Google Patents
Verfahren zur herstellung von 3-indol-aliphatischen saeuren.Info
- Publication number
- CH557815A CH557815A CH236268A CH236268A CH557815A CH 557815 A CH557815 A CH 557815A CH 236268 A CH236268 A CH 236268A CH 236268 A CH236268 A CH 236268A CH 557815 A CH557815 A CH 557815A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- lower alkyl
- indolyl
- substituted
- aryl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- -1 heteroaryl radical Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical class [H]N([H])C([H])([H])* 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 125000005363 dialkylsulfonamide group Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 4
- 206010018691 Granuloma Diseases 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000003973 alkyl amines Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KFYKZKISJBGVMR-ZCFIWIBFSA-N (2r)-n-ethylbutan-2-amine Chemical compound CCN[C@H](C)CC KFYKZKISJBGVMR-ZCFIWIBFSA-N 0.000 description 1
- MWUSAETYTBNPDG-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC(=O)C1=CC=C(Cl)C=C1 MWUSAETYTBNPDG-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- FDXOLWVATQFZJC-UHFFFAOYSA-N 2-(1-benzoyl-5-methoxy-2-methylindol-3-yl)acetamide Chemical compound CC1=C(CC(N)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=CC=C1 FDXOLWVATQFZJC-UHFFFAOYSA-N 0.000 description 1
- YNDQHILWWBPAPR-UHFFFAOYSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamide Chemical compound CC1=C(CC(N)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 YNDQHILWWBPAPR-UHFFFAOYSA-N 0.000 description 1
- ZFDZYMHUPHHSEZ-UHFFFAOYSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]propanoic acid Chemical compound CC1=C(C(C)C(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 ZFDZYMHUPHHSEZ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CIHCYOATKNZBGL-UHFFFAOYSA-N CC1=CC=C(C(=S)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 Chemical compound CC1=CC=C(C(=S)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 CIHCYOATKNZBGL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- NJASLAROWSIPFQ-UHFFFAOYSA-N tert-butyl 2-(5-methoxy-2-methyl-1h-indol-3-yl)acetate Chemical compound COC1=CC=C2NC(C)=C(CC(=O)OC(C)(C)C)C2=C1 NJASLAROWSIPFQ-UHFFFAOYSA-N 0.000 description 1
- JDNRBNRROYRSAG-UHFFFAOYSA-N tert-butyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound CC1=C(CC(=O)OC(C)(C)C)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 JDNRBNRROYRSAG-UHFFFAOYSA-N 0.000 description 1
- 230000009772 tissue formation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
-
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
-
- 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
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25564263A | 1963-02-01 | 1963-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH557815A true CH557815A (de) | 1975-01-15 |
Family
ID=22969254
Family Applications (16)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236268A CH557815A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur herstellung von 3-indol-aliphatischen saeuren. |
| CH419468A CH466284A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH1674468A CH466288A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH236468A CH466283A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-aliphatischen Säuren |
| CH235868A CH457434A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung des t-Butylesters von 3-indol-niederaliphatischen Säuren |
| CH1674568A CH466289A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Alcyl-3-Indolyl-aliphatischen Säuren |
| CH236668A CH457437A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH444166A CH466285A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-indolyl-essigsäure oder deren Ester |
| CH236168A CH464202A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indol-niederaliphatischen Säuren |
| CH490368A CH466287A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH1674768A CH466290A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-indolyl-aliphatischen Säuren |
| CH236568A CH464203A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-indolyl-aliphatischen Säuren oder deren t-Butyl-Estern |
| CH490268A CH466286A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-Indolyl-aliphatischen Säuren |
| CH236368A CH457436A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von Estern von 3-Indolyl-niederaliphatischen Säuren |
| CH236068A CH457435A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von Estern von 3-indol-aliphatischen Säuren |
| CH115364A CH489495A (de) | 1963-02-01 | 1967-02-23 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
Family Applications After (15)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH419468A CH466284A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH1674468A CH466288A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH236468A CH466283A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-aliphatischen Säuren |
| CH235868A CH457434A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung des t-Butylesters von 3-indol-niederaliphatischen Säuren |
| CH1674568A CH466289A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Alcyl-3-Indolyl-aliphatischen Säuren |
| CH236668A CH457437A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH444166A CH466285A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-indolyl-essigsäure oder deren Ester |
| CH236168A CH464202A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indol-niederaliphatischen Säuren |
| CH490368A CH466287A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
| CH1674768A CH466290A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-indolyl-aliphatischen Säuren |
| CH236568A CH464203A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-indolyl-aliphatischen Säuren oder deren t-Butyl-Estern |
| CH490268A CH466286A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von 1-Acyl-3-Indolyl-aliphatischen Säuren |
| CH236368A CH457436A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von Estern von 3-Indolyl-niederaliphatischen Säuren |
| CH236068A CH457435A (de) | 1963-02-01 | 1964-01-31 | Verfahren zur Herstellung von Estern von 3-indol-aliphatischen Säuren |
| CH115364A CH489495A (de) | 1963-02-01 | 1967-02-23 | Verfahren zur Herstellung von 3-Indolyl-niederaliphatischen Säuren |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT277992B (enExample) |
| BE (1) | BE643268A (enExample) |
| BR (1) | BR6456479D0 (enExample) |
| CH (16) | CH557815A (enExample) |
| DE (16) | DE1695492A1 (enExample) |
| DK (11) | DK109562C (enExample) |
| FI (9) | FI46955C (enExample) |
| FR (1) | FR1559559A (enExample) |
| GB (13) | GB1050729A (enExample) |
| NL (1) | NL6400813A (enExample) |
| SE (12) | SE307948B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU163233B (enExample) * | 1970-07-31 | 1973-07-28 | ||
| JP2934269B2 (ja) * | 1988-06-21 | 1999-08-16 | ビータ・ツェーンファブリーク・ハー・ラウテル・ゲーエムベーハー・ウント・コ・カーゲー | 分散セラミック組成物 |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
-
0
- GB GB1050740D patent/GB1050740A/en active Active
- GB GB1050733D patent/GB1050733A/en active Active
- GB GB1050734D patent/GB1050734A/en active Active
- GB GB1050737D patent/GB1050737A/en active Active
- GB GB1050735D patent/GB1050735A/en active Active
- GB GB1050739D patent/GB1050739A/en active Active
- GB GB1050730D patent/GB1050730A/en active Active
- GB GB1050728D patent/GB1050728A/en active Active
- GB GB1050736D patent/GB1050736A/en active Active
- GB GB1050732D patent/GB1050732A/en active Active
- GB GB1050738D patent/GB1050738A/en active Active
- GB GB1050731D patent/GB1050731A/en active Active
- GB GB1050729D patent/GB1050729A/en active Active
-
1964
- 1964-01-14 DE DE19641695492 patent/DE1695492A1/de active Pending
- 1964-01-24 DE DE19641695490 patent/DE1695490A1/de active Pending
- 1964-01-24 DE DE19641695485 patent/DE1695485A1/de active Pending
- 1964-01-24 DE DE19641793561 patent/DE1793561A1/de active Pending
- 1964-01-24 DE DE19641695486 patent/DE1695486A1/de active Pending
- 1964-01-24 DE DE19641770132 patent/DE1770132A1/de active Pending
- 1964-01-24 DE DE19641695491 patent/DE1695491A1/de active Pending
- 1964-01-24 DE DE19641770802 patent/DE1770802A1/de active Pending
- 1964-01-24 DE DE19641695488 patent/DE1695488A1/de active Pending
- 1964-01-24 DE DE19641695484 patent/DE1695484A1/de active Pending
- 1964-01-24 DE DE19641770134 patent/DE1770134A1/de active Pending
- 1964-01-24 DE DE19641695487 patent/DE1695487A1/de active Pending
- 1964-01-24 DE DE19641470059D patent/DE1470059B1/de active Pending
- 1964-01-24 DE DE19641695489 patent/DE1695489A1/de active Pending
- 1964-01-24 DE DE19641770116 patent/DE1770116A1/de active Pending
- 1964-01-24 DE DE19641695493 patent/DE1695493A1/de active Pending
- 1964-01-28 AT AT01821/67A patent/AT277992B/de not_active IP Right Cessation
- 1964-01-28 BR BR15647964A patent/BR6456479D0/pt unknown
- 1964-01-29 FI FI16964A patent/FI46955C/fi active
- 1964-01-31 CH CH236268A patent/CH557815A/de not_active IP Right Cessation
- 1964-01-31 CH CH419468A patent/CH466284A/de unknown
- 1964-01-31 FR FR1559559D patent/FR1559559A/fr not_active Expired
- 1964-01-31 NL NL6400813A patent/NL6400813A/xx unknown
- 1964-01-31 CH CH1674468A patent/CH466288A/de unknown
- 1964-01-31 CH CH236468A patent/CH466283A/de unknown
- 1964-01-31 BE BE643268D patent/BE643268A/xx unknown
- 1964-01-31 CH CH235868A patent/CH457434A/de unknown
- 1964-01-31 CH CH1674568A patent/CH466289A/de unknown
- 1964-01-31 CH CH236668A patent/CH457437A/de unknown
- 1964-01-31 DK DK598265A patent/DK109562C/da active
- 1964-01-31 CH CH444166A patent/CH466285A/de unknown
- 1964-01-31 CH CH236168A patent/CH464202A/de unknown
- 1964-01-31 CH CH490368A patent/CH466287A/de unknown
- 1964-01-31 CH CH1674768A patent/CH466290A/de unknown
- 1964-01-31 CH CH236568A patent/CH464203A/de unknown
- 1964-01-31 DK DK48964A patent/DK112238B/da unknown
- 1964-01-31 CH CH490268A patent/CH466286A/de unknown
- 1964-01-31 SE SE123764A patent/SE307948B/xx unknown
- 1964-01-31 CH CH236368A patent/CH457436A/de unknown
- 1964-01-31 DK DK598765A patent/DK109334C/da active
- 1964-01-31 SE SE89267A patent/SE302463B/xx unknown
- 1964-01-31 DK DK598565A patent/DK109514C/da active
- 1964-01-31 CH CH236068A patent/CH457435A/de unknown
- 1964-01-31 SE SE88967A patent/SE317975B/xx unknown
-
1965
- 1965-11-22 DK DK598965A patent/DK112314B/da unknown
- 1965-11-22 DK DK598665A patent/DK112239B/da unknown
- 1965-11-22 DK DK598465A patent/DK111751B/da unknown
- 1965-11-22 DK DK598365A patent/DK113501B/da unknown
- 1965-11-22 DK DK598865A patent/DK112313B/da unknown
-
1966
- 1966-02-23 DK DK93366A patent/DK112447B/da unknown
- 1966-02-23 DK DK93266A patent/DK112446B/da unknown
-
1967
- 1967-01-20 SE SE894/67A patent/SE320367B/xx unknown
- 1967-01-20 SE SE89367A patent/SE302133B/xx unknown
- 1967-01-20 SE SE890/67A patent/SE307133B/xx unknown
- 1967-01-20 SE SE88667A patent/SE302130B/xx unknown
- 1967-01-20 SE SE896/67A patent/SE320666B/xx unknown
- 1967-01-20 SE SE895/67A patent/SE320069B/xx unknown
- 1967-01-20 SE SE891/67A patent/SE304995B/xx unknown
- 1967-01-20 SE SE88867A patent/SE302132B/xx unknown
- 1967-01-31 SE SE88767A patent/SE302131B/xx unknown
- 1967-02-23 CH CH115364A patent/CH489495A/de not_active IP Right Cessation
-
1970
- 1970-09-21 FI FI257570A patent/FI47101C/fi active
- 1970-09-21 FI FI702570A patent/FI47097C/fi active
- 1970-09-21 FI FI257270A patent/FI47099C/fi active
- 1970-09-21 FI FI257170A patent/FI47098C/fi active
- 1970-09-21 FI FI256870A patent/FI47096C/fi active
- 1970-09-21 FI FI257070A patent/FI47097B/fi active
- 1970-09-21 FI FI257470A patent/FI47100C/fi active
- 1970-09-21 FI FI257370A patent/FI47185C/fi active
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased |