DE2127352A1 - Tetrahydrocarbazone und Verfahren zu ihrer Herstellung - Google Patents
Tetrahydrocarbazone und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2127352A1 DE2127352A1 DE19712127352 DE2127352A DE2127352A1 DE 2127352 A1 DE2127352 A1 DE 2127352A1 DE 19712127352 DE19712127352 DE 19712127352 DE 2127352 A DE2127352 A DE 2127352A DE 2127352 A1 DE2127352 A1 DE 2127352A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydrocarbazole
- alkyl
- compound
- formula
- carboxylic 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 107
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 161
- -1 phenoxy, phenyl Chemical group 0.000 claims description 110
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical group N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- NHOAIPRHGSAFDL-UHFFFAOYSA-N 4-oxocyclohexane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC(=O)CC1 NHOAIPRHGSAFDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001805 chlorine compounds Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LSSKLEGFTVZDTJ-UHFFFAOYSA-N 9-(4-chlorobenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid Chemical compound C1C(C(=O)O)CCC2=C1C1=CC=CC=C1N2C(=O)C1=CC=C(Cl)C=C1 LSSKLEGFTVZDTJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- DJXJARQPGKYVNA-UHFFFAOYSA-N trifluoromethanolate Chemical group [O-]C(F)(F)F DJXJARQPGKYVNA-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- OWLXUYGCLDGHJJ-UHFFFAOYSA-N 4-oxocyclohexanecarboxylic acid Chemical compound OC(=O)C1CCC(=O)CC1 OWLXUYGCLDGHJJ-UHFFFAOYSA-N 0.000 description 27
- 235000019441 ethanol Nutrition 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- CGJLAUQMHSAAMY-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1CCC(C(=O)O)C2 CGJLAUQMHSAAMY-UHFFFAOYSA-N 0.000 description 16
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 16
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000012259 ether extract Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 241000700159 Rattus Species 0.000 description 9
- 125000005907 alkyl ester group Chemical group 0.000 description 9
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 9
- 235000015497 potassium bicarbonate Nutrition 0.000 description 9
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 9
- 239000011736 potassium bicarbonate Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011592 zinc chloride Substances 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000010561 standard procedure Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001649 bromium compounds Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- KURBTRNHGDQKOS-XNWCZRBMSA-N n-[(e)-ethylideneamino]aniline Chemical compound C\C=N\NC1=CC=CC=C1 KURBTRNHGDQKOS-XNWCZRBMSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 150000004031 phenylhydrazines Chemical class 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- AWMZFBYYIATTOW-UHFFFAOYSA-N 2-anilinocyclohexan-1-one Chemical compound O=C1CCCCC1NC1=CC=CC=C1 AWMZFBYYIATTOW-UHFFFAOYSA-N 0.000 description 3
- MMVMNZMLPWLVPF-UHFFFAOYSA-N 9-benzyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical class OC(=O)C1CCCC2=C1C1=CC=CC=C1N2CC1=CC=CC=C1 MMVMNZMLPWLVPF-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
- JXNAMWJFKJVULY-UHFFFAOYSA-N benzyl 2,3,4,9-tetrahydro-1h-carbazole-4-carboxylate Chemical compound C1CCC=2NC3=CC=CC=C3C=2C1C(=O)OCC1=CC=CC=C1 JXNAMWJFKJVULY-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 3
- LKJREFMWHBWKNF-UHFFFAOYSA-N n-(benzylideneamino)-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1N(C(=O)C=1C=CC=CC=1)N=CC1=CC=CC=C1 LKJREFMWHBWKNF-UHFFFAOYSA-N 0.000 description 3
- PCDRHQQNUZVJAV-UHFFFAOYSA-N n-phenylbenzohydrazide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N(N)C(=O)C1=CC=CC=C1 PCDRHQQNUZVJAV-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- GLDKSOIMQKTVTN-UHFFFAOYSA-N 6-methyl-2,3,4,9-tetrahydro-1h-carbazole-4-carboxylic acid Chemical compound C1CCC(C(O)=O)C2=C1NC1=CC=C(C)C=C12 GLDKSOIMQKTVTN-UHFFFAOYSA-N 0.000 description 2
- INFCKBHOIYWABK-UHFFFAOYSA-N 9-(3,4,5-trimethoxybenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2C3=CC=CC=C3C=3CC(CCC=32)C(O)=O)=C1 INFCKBHOIYWABK-UHFFFAOYSA-N 0.000 description 2
- KHGQJPUQXUAALX-UHFFFAOYSA-N 9-(3-methylbenzoyl)-2,4-dihydro-1h-carbazole-3,3-dicarboxylic acid Chemical compound CC1=CC=CC(C(=O)N2C3=CC=CC=C3C=3CC(CCC=32)(C(O)=O)C(O)=O)=C1 KHGQJPUQXUAALX-UHFFFAOYSA-N 0.000 description 2
- WMFKSJIGOOOJOX-UHFFFAOYSA-N 9-(4-fluorobenzoyl)-2,4-dihydro-1h-carbazole-3,3-dicarboxylic acid Chemical compound C1C(C(=O)O)(C(O)=O)CCC2=C1C1=CC=CC=C1N2C(=O)C1=CC=C(F)C=C1 WMFKSJIGOOOJOX-UHFFFAOYSA-N 0.000 description 2
- VNZMCVPMVJVEPJ-UHFFFAOYSA-N 9-benzoyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1C1=CC=CC=C1N2C(=O)C1=CC=CC=C1 VNZMCVPMVJVEPJ-UHFFFAOYSA-N 0.000 description 2
- JFQZEZNURSYVCP-UHFFFAOYSA-N 9-benzoyl-2,4-dihydro-1h-carbazole-3,3-dicarboxylic acid Chemical compound C1C(C(=O)O)(C(O)=O)CCC2=C1C1=CC=CC=C1N2C(=O)C1=CC=CC=C1 JFQZEZNURSYVCP-UHFFFAOYSA-N 0.000 description 2
- CYCDEUYLQQBNKW-UHFFFAOYSA-N 9-benzoyl-6,7-dimethoxy-2,4-dihydro-1h-carbazole-3,3-dicarboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2C=2CC(C(O)=O)(C(O)=O)CCC=2N1C(=O)C1=CC=CC=C1 CYCDEUYLQQBNKW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- WJBIYCLEZUXDIM-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methoxybenzohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(=O)N(N)C1=CC=C(F)C=C1 WJBIYCLEZUXDIM-UHFFFAOYSA-N 0.000 description 1
- YVPZHOAVAUUFTQ-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methylbenzohydrazide;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(=O)N(N)C1=CC=C(F)C=C1 YVPZHOAVAUUFTQ-UHFFFAOYSA-N 0.000 description 1
- DGMWNFUMSVPZGJ-UHFFFAOYSA-N n-(4-fluorophenyl)benzohydrazide;hydrochloride Chemical compound Cl.C=1C=C(F)C=CC=1N(N)C(=O)C1=CC=CC=C1 DGMWNFUMSVPZGJ-UHFFFAOYSA-N 0.000 description 1
- HYWHVCNVLIUDBX-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-methylbenzohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=C(C)C=C1 HYWHVCNVLIUDBX-UHFFFAOYSA-N 0.000 description 1
- UFRMEGUEJRNKBI-UHFFFAOYSA-N n-(4-methoxyphenyl)benzohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=CC=C1 UFRMEGUEJRNKBI-UHFFFAOYSA-N 0.000 description 1
- RZVHWULJOZYJLC-UHFFFAOYSA-N n-(4-methylphenyl)benzohydrazide;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1N(N)C(=O)C1=CC=CC=C1 RZVHWULJOZYJLC-UHFFFAOYSA-N 0.000 description 1
- KXWRAYYJNDJVHT-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)benzohydrazide;hydrochloride Chemical compound Cl.C=1C=C(OCC=2C=CC=CC=2)C=CC=1N(N)C(=O)C1=CC=CC=C1 KXWRAYYJNDJVHT-UHFFFAOYSA-N 0.000 description 1
- OPPAWZYFSHXJLA-UHFFFAOYSA-N n-(benzylideneamino)-2-fluoroaniline Chemical compound FC1=CC=CC=C1NN=CC1=CC=CC=C1 OPPAWZYFSHXJLA-UHFFFAOYSA-N 0.000 description 1
- ILWSAUNMQFNDPO-UHFFFAOYSA-N n-(benzylideneamino)-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NN=CC1=CC=CC=C1 ILWSAUNMQFNDPO-UHFFFAOYSA-N 0.000 description 1
- RILJYNNESBKLPN-UHFFFAOYSA-N n-(benzylideneamino)-n-phenylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)N=CC1=CC=CC=C1 RILJYNNESBKLPN-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DZUBLCBPKBYWBC-UHFFFAOYSA-N n-phenyl-1,3-benzodioxole-5-carbohydrazide;hydrochloride Chemical compound Cl.C=1C=C2OCOC2=CC=1C(=O)N(N)C1=CC=CC=C1 DZUBLCBPKBYWBC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SEFNHMSRQKRAIT-UHFFFAOYSA-N oxolane;pentane Chemical compound CCCCC.C1CCOC1 SEFNHMSRQKRAIT-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4262070A | 1970-06-02 | 1970-06-02 | |
| US20020571A | 1971-11-18 | 1971-11-18 | |
| US314099A US3905998A (en) | 1970-06-02 | 1972-12-11 | 1,2,3,4 Tetrahydrocarbazole-3-carboxylic and 4-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2127352A1 true DE2127352A1 (de) | 1972-01-27 |
Family
ID=27366172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712127352 Ceased DE2127352A1 (de) | 1970-06-02 | 1971-06-02 | Tetrahydrocarbazone und Verfahren zu ihrer Herstellung |
Country Status (8)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060550A (en) * | 1970-08-26 | 1977-11-29 | Sumitomo Chemical Company, Limited | Novel n'-acylated phenyl-hydrazine and -hydrazone derivatives |
| US3941805A (en) * | 1972-11-17 | 1976-03-02 | Sterling Drug Inc. | 3-Halomethylcarbonyl-9-benzoyl-1,2,3,4-tetrahydrocarbazoles |
| US3835152A (en) * | 1972-11-17 | 1974-09-10 | Sterling Drug Inc | 3-cyano-9-benzoyl-1,2,3,4-tetrahydro carbazole |
| US3948938A (en) * | 1972-12-29 | 1976-04-06 | American Color & Chemical Corporation | Polymeric materials colored with yellow methine dyes and pigments |
| ATE90076T1 (de) | 1986-03-27 | 1993-06-15 | Merck Frosst Canada Inc | Tetrahydrocarbazole ester. |
| US4775680A (en) * | 1987-07-21 | 1988-10-04 | Merck & Co., Inc. | Cyclohept[b]indolealkanoic acids, pharmaceutical compositions and use |
| CA2196046A1 (en) * | 1994-07-27 | 1996-02-08 | Nigel Birdsall | Heterocyclic compounds, useful as allosteric effectors at muscarinic receptors |
| PT1833791E (pt) * | 2004-12-27 | 2011-10-19 | Actelion Pharmaceuticals Ltd | Derivados de 2,3,4,9-tetra-hidro-1h-carbazol como antgonistas do receptor crth2 |
| US7662831B2 (en) * | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US7601856B2 (en) * | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US9346803B2 (en) | 2011-10-17 | 2016-05-24 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
-
1970
- 1970-06-02 US US42620A patent/US3687969A/en not_active Expired - Lifetime
-
1971
- 1971-05-28 CA CA114,287A patent/CA960665A/en not_active Expired
- 1971-06-01 GB GB1845971*[A patent/GB1335227A/en not_active Expired
- 1971-06-02 CH CH800471A patent/CH533112A/fr not_active IP Right Cessation
- 1971-06-02 BE BE767968A patent/BE767968A/xx unknown
- 1971-06-02 NL NL7107589A patent/NL7107589A/xx not_active Application Discontinuation
- 1971-06-02 FR FR7119972A patent/FR2100715B1/fr not_active Expired
- 1971-06-02 DE DE19712127352 patent/DE2127352A1/de not_active Ceased
- 1971-11-18 US US00200205A patent/US3758496A/en not_active Expired - Lifetime
-
1972
- 1972-12-11 US US314099A patent/US3905998A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1335227A (en) | 1973-10-24 |
| NL7107589A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-12-06 |
| FR2100715B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-23 |
| BE767968A (fr) | 1971-12-02 |
| US3905998A (en) | 1975-09-16 |
| FR2100715A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-03-24 |
| CA960665A (en) | 1975-01-07 |
| US3758496A (en) | 1973-09-11 |
| US3687969A (en) | 1972-08-29 |
| CH533112A (fr) | 1973-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |