NO742601L - - Google Patents
Info
- Publication number
- NO742601L NO742601L NO742601A NO742601A NO742601L NO 742601 L NO742601 L NO 742601L NO 742601 A NO742601 A NO 742601A NO 742601 A NO742601 A NO 742601A NO 742601 L NO742601 L NO 742601L
- Authority
- NO
- Norway
- Prior art keywords
- carboxylic acid
- carbazole
- methyl
- chloro
- ethyl ester
- Prior art date
Links
- -1 oximinocarbonyl Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 21
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 16
- 150000001298 alcohols Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 58
- 230000008018 melting Effects 0.000 description 58
- 238000001953 recrystallisation Methods 0.000 description 43
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 150000001716 carbazoles Chemical class 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 230000003110 anti-inflammatory effect Effects 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 150000002168 ethanoic acid esters Chemical class 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- NDRBUFWYCLTVBV-UHFFFAOYSA-N ethyl 7-chloro-8-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(C)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 NDRBUFWYCLTVBV-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 description 4
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- NAERWUXELMQKIT-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(C)=C(Cl)C=C2 NAERWUXELMQKIT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 230000000694 effects 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- WQWUWOFABYZAOC-UHFFFAOYSA-N 3-chloro-6,7,8,9-tetrahydro-5h-carbazole-1-carboxylic acid Chemical compound C1CCCC2=C1C(C=C(Cl)C=C1C(=O)O)=C1N2 WQWUWOFABYZAOC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LKZDXEIDUKUTMD-UHFFFAOYSA-N 7,8-dimethyl-9h-carbazole-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2NC3=C(C)C(C)=CC=C3C2=C1 LKZDXEIDUKUTMD-UHFFFAOYSA-N 0.000 description 2
- ALRRWAPRCLSXHX-UHFFFAOYSA-N 7-chloro-8-ethyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(CC)=C(Cl)C=C2 ALRRWAPRCLSXHX-UHFFFAOYSA-N 0.000 description 2
- FZTCDLZTKNSKCX-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carbonitrile Chemical compound C12=CC=CC(C#N)=C2NC2=C1C=CC(Cl)=C2C FZTCDLZTKNSKCX-UHFFFAOYSA-N 0.000 description 2
- ZAYRIWYHTHCTNP-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carboxamide Chemical compound N1C2=C(C(N)=O)C=CC=C2C2=C1C(C)=C(Cl)C=C2 ZAYRIWYHTHCTNP-UHFFFAOYSA-N 0.000 description 2
- TWYDFZZEERAMEH-UHFFFAOYSA-N 7-chloro-n-hydroxy-8-methyl-9h-carbazole-1-carboxamide Chemical compound N1C2=C(C(=O)NO)C=CC=C2C2=C1C(C)=C(Cl)C=C2 TWYDFZZEERAMEH-UHFFFAOYSA-N 0.000 description 2
- NIEJYFQQHMRGHX-UHFFFAOYSA-N 8-methyl-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2NC2=C1C=CC=C2C NIEJYFQQHMRGHX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MZELDQBKQWZTDJ-UHFFFAOYSA-N ethyl 11H-benzo[a]carbazole-1-carboxylate Chemical compound C1=CC=C2NC3=C4C(C(=O)OCC)=CC=CC4=CC=C3C2=C1 MZELDQBKQWZTDJ-UHFFFAOYSA-N 0.000 description 2
- JZPOPPJPVFOZKK-UHFFFAOYSA-N ethyl 5-chloro-8-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=C(C=CC(=C3NC12)OC)Cl JZPOPPJPVFOZKK-UHFFFAOYSA-N 0.000 description 2
- RNCXMGDBZYDSOE-UHFFFAOYSA-N ethyl 6-methoxy-9h-carbazole-1-carboxylate Chemical compound N1C2=CC=C(OC)C=C2C2=C1C(C(=O)OCC)=CC=C2 RNCXMGDBZYDSOE-UHFFFAOYSA-N 0.000 description 2
- DXDQBVWBDNRQFI-UHFFFAOYSA-N ethyl 7,8-dimethyl-9H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1=CC=CC=2C3=CC=C(C(=C3NC12)C)C DXDQBVWBDNRQFI-UHFFFAOYSA-N 0.000 description 2
- BKJULXAGOYSYHN-UHFFFAOYSA-N ethyl 7-chloro-6-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=CC(Cl)=C(C)C=C2C2=C1C(C(=O)OCC)=CC=C2 BKJULXAGOYSYHN-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- CANSWZHFWLNCPV-UHFFFAOYSA-N ethyl 3-bromo-5-methyl-2-oxocyclohexane-1-carboxylate Chemical compound C(C)OC(=O)C1C(C(CC(C1)C)Br)=O CANSWZHFWLNCPV-UHFFFAOYSA-N 0.000 description 1
- ULAGQQHXWCPBCD-UHFFFAOYSA-N ethyl 3-methoxy-9H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1=CC(=CC=2C3=CC=CC=C3NC1=2)OC ULAGQQHXWCPBCD-UHFFFAOYSA-N 0.000 description 1
- CLJXERHFEVKSGU-UHFFFAOYSA-N ethyl 5-chloro-6-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=C(C)C(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 CLJXERHFEVKSGU-UHFFFAOYSA-N 0.000 description 1
- FFZCZDLYNHBTKH-UHFFFAOYSA-N ethyl 5-chloro-8-methoxy-9H-carbazole-1-carboxylate Chemical compound N1C2=C(OC)C=CC(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 FFZCZDLYNHBTKH-UHFFFAOYSA-N 0.000 description 1
- URTVPXRFRXWSTG-UHFFFAOYSA-N ethyl 5-chloro-8-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=C(C=CC(=C3NC12)C)Cl URTVPXRFRXWSTG-UHFFFAOYSA-N 0.000 description 1
- VKWLMWIFIMGBRR-UHFFFAOYSA-N ethyl 5-chloro-8-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(C)C=CC(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 VKWLMWIFIMGBRR-UHFFFAOYSA-N 0.000 description 1
- NKFBFGUTZNPPJH-UHFFFAOYSA-N ethyl 6-fluoro-2,3,4,9-tetrahydro-1h-carbazole-1-carboxylate Chemical compound N1C2=CC=C(F)C=C2C2=C1C(C(=O)OCC)CCC2 NKFBFGUTZNPPJH-UHFFFAOYSA-N 0.000 description 1
- FOJPERZKPIUMTK-UHFFFAOYSA-N ethyl 6-fluoro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=C(F)C=C2C2=C1C(C(=O)OCC)=CC=C2 FOJPERZKPIUMTK-UHFFFAOYSA-N 0.000 description 1
- UUZWYPMJBQFACW-UHFFFAOYSA-N ethyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC(=CC=C3NC12)OC UUZWYPMJBQFACW-UHFFFAOYSA-N 0.000 description 1
- NCAFTQQSBUWCJT-UHFFFAOYSA-N ethyl 7,8-dichloro-9H-carbazole-1-carboxylate Chemical compound N1C2=C(Cl)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 NCAFTQQSBUWCJT-UHFFFAOYSA-N 0.000 description 1
- GLOZCCYBWSLPKY-UHFFFAOYSA-N ethyl 7,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)C)C GLOZCCYBWSLPKY-UHFFFAOYSA-N 0.000 description 1
- CXTSOVZJZKJWLZ-UHFFFAOYSA-N ethyl 7-(trifluoromethyl)-9h-carbazole-1-carboxylate Chemical compound N1C2=CC(C(F)(F)F)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 CXTSOVZJZKJWLZ-UHFFFAOYSA-N 0.000 description 1
- PHFXYUHXCNSTRG-UHFFFAOYSA-N ethyl 7-chloro-3,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CC(CC=2C3=CC=C(C(=C3NC12)C)Cl)C PHFXYUHXCNSTRG-UHFFFAOYSA-N 0.000 description 1
- LOJCPKIUNWUVBL-UHFFFAOYSA-N ethyl 7-chloro-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC(=C(C=C3NC12)Cl)C LOJCPKIUNWUVBL-UHFFFAOYSA-N 0.000 description 1
- AYTLNKFBPOVHFY-UHFFFAOYSA-N ethyl 7-chloro-8-ethyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(CC)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 AYTLNKFBPOVHFY-UHFFFAOYSA-N 0.000 description 1
- IGDIDRYAZLWWOG-UHFFFAOYSA-N ethyl 7-chloro-8-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)C)Cl IGDIDRYAZLWWOG-UHFFFAOYSA-N 0.000 description 1
- YURKAGDJOIRLFK-UHFFFAOYSA-N ethyl 8-chloro-7-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)Cl)C YURKAGDJOIRLFK-UHFFFAOYSA-N 0.000 description 1
- OKDJIWVZJOYKLB-UHFFFAOYSA-N ethyl 8-chloro-7-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(Cl)C(C)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 OKDJIWVZJOYKLB-UHFFFAOYSA-N 0.000 description 1
- IMVOMWYKXZDVCE-UHFFFAOYSA-N ethyl 8-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=CC(=C3NC12)OC IMVOMWYKXZDVCE-UHFFFAOYSA-N 0.000 description 1
- NXQHRDRYVHCDBM-UHFFFAOYSA-N ethyl 8-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=CC(=C3NC12)C NXQHRDRYVHCDBM-UHFFFAOYSA-N 0.000 description 1
- HKJKSNKBCAWPNJ-UHFFFAOYSA-N ethyl 9-benzyl-7-chloro-8-methylcarbazole-1-carboxylate Chemical compound C1=2C(C(=O)OCC)=CC=CC=2C2=CC=C(Cl)C(C)=C2N1CC1=CC=CC=C1 HKJKSNKBCAWPNJ-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- FCHAVHVICJJSTO-UHFFFAOYSA-N methyl 2,3,4,9-tetrahydro-1h-carbazole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OC)CCC2 FCHAVHVICJJSTO-UHFFFAOYSA-N 0.000 description 1
- VAQBJVZNPBNHGC-UHFFFAOYSA-N methyl 2-amino-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1N VAQBJVZNPBNHGC-UHFFFAOYSA-N 0.000 description 1
- IGHVUURTQGBABT-UHFFFAOYSA-N methyl 2-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1N IGHVUURTQGBABT-UHFFFAOYSA-N 0.000 description 1
- SSVMIMPSMYTRIF-UHFFFAOYSA-N methyl 3-chloro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OC)=CC(Cl)=C2 SSVMIMPSMYTRIF-UHFFFAOYSA-N 0.000 description 1
- QZLUKNZJAKEZOW-UHFFFAOYSA-N methyl 4-chloro-6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate Chemical compound COC(=O)C1=CC=C(C=2C=3CCCCC3NC12)Cl QZLUKNZJAKEZOW-UHFFFAOYSA-N 0.000 description 1
- XFMOTEIBBVTYND-UHFFFAOYSA-N methyl 4-chloro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OC)=CC=C2Cl XFMOTEIBBVTYND-UHFFFAOYSA-N 0.000 description 1
- YLBSTBPBIVGLIW-UHFFFAOYSA-N methyl 4-methyl-6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate Chemical compound COC(=O)C1=CC=C(C=2C=3CCCCC3NC12)C YLBSTBPBIVGLIW-UHFFFAOYSA-N 0.000 description 1
- UUQGGRYGFAPQAL-UHFFFAOYSA-N methyl 6,7,8,9-tetrahydro-5h-carbazole-1-carboxylate Chemical compound C1CCCC2=C1C(C=CC=C1C(=O)OC)=C1N2 UUQGGRYGFAPQAL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229920006395 saturated elastomer Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
- 238000005303 weighing Methods 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
- C07D209/56—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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2337154A DE2337154C2 (de) | 1973-07-18 | 1973-07-18 | Neue Carbazolderivate |
| DE2431292A DE2431292A1 (de) | 1974-06-27 | 1974-06-27 | Neue carbazol-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742601L true NO742601L (es) | 1975-02-17 |
Family
ID=25765532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742601A NO742601L (es) | 1973-07-18 | 1974-07-17 |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5069072A (es) |
| AT (1) | AT342583B (es) |
| BG (1) | BG25793A3 (es) |
| CA (1) | CA1053682A (es) |
| CH (1) | CH619213A5 (es) |
| CS (1) | CS190431B2 (es) |
| DD (1) | DD114075A5 (es) |
| DK (1) | DK388074A (es) |
| ES (1) | ES428379A1 (es) |
| FI (1) | FI218874A (es) |
| FR (1) | FR2237628B1 (es) |
| GB (1) | GB1482771A (es) |
| HU (1) | HU173115B (es) |
| IE (1) | IE39624B1 (es) |
| IL (1) | IL45298A (es) |
| NL (1) | NL7409715A (es) |
| NO (1) | NO742601L (es) |
| RO (1) | RO72713A (es) |
| SE (1) | SE396602B (es) |
| SU (1) | SU511855A3 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060074124A1 (en) * | 2003-09-12 | 2006-04-06 | Andrew Napper | Methods of treating a disorder |
| JP4908215B2 (ja) * | 2003-09-12 | 2012-04-04 | エリクサー ファーマスーティカルズ インコーポレイテッド | 疾患の治療法 |
| US8143257B2 (en) * | 2004-11-23 | 2012-03-27 | Ptc Therapeutics, Inc. | Substituted phenols as active agents inhibiting VEGF production |
| AR088377A1 (es) | 2011-10-20 | 2014-05-28 | Siena Biotech Spa | Proceso para la preparacion de 6-cloro-2,3,4,9-tetrahidro-1h-carbazol-1-carboxamida y compuestos intermedios de esta |
| CA3059631A1 (en) * | 2017-04-11 | 2018-10-18 | Saje Pharma, Llc | Carbazole compounds and methods of use thereof |
| JP2021134141A (ja) * | 2020-02-21 | 2021-09-13 | エヌ・イーケムキャット株式会社 | 不均一系貴金属触媒を用いた芳香族化合物の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7008628A (es) * | 1969-06-25 | 1970-12-29 |
-
1974
- 1974-07-15 BG BG027244A patent/BG25793A3/xx unknown
- 1974-07-16 DD DD179943A patent/DD114075A5/xx unknown
- 1974-07-17 ES ES428379A patent/ES428379A1/es not_active Expired
- 1974-07-17 HU HU24SC483A patent/HU173115B/hu unknown
- 1974-07-17 CS CS745109A patent/CS190431B2/cs unknown
- 1974-07-17 NO NO742601A patent/NO742601L/no unknown
- 1974-07-17 FI FI2188/74A patent/FI218874A/fi unknown
- 1974-07-17 SE SE7409330A patent/SE396602B/xx unknown
- 1974-07-18 JP JP49082669A patent/JPS5069072A/ja active Pending
- 1974-07-18 IE IE1519/74A patent/IE39624B1/xx unknown
- 1974-07-18 AT AT596074A patent/AT342583B/de active
- 1974-07-18 SU SU2048652A patent/SU511855A3/ru active
- 1974-07-18 CH CH990174A patent/CH619213A5/de not_active IP Right Cessation
- 1974-07-18 NL NL7409715A patent/NL7409715A/xx not_active Application Discontinuation
- 1974-07-18 CA CA205,063A patent/CA1053682A/en not_active Expired
- 1974-07-18 DK DK388074A patent/DK388074A/da not_active Application Discontinuation
- 1974-07-18 IL IL45298A patent/IL45298A/xx unknown
- 1974-07-18 RO RO7479524A patent/RO72713A/ro unknown
- 1974-07-18 GB GB31966/74A patent/GB1482771A/en not_active Expired
- 1974-07-18 FR FR7424991A patent/FR2237628B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BG25793A3 (en) | 1978-12-12 |
| ES428379A1 (es) | 1976-09-16 |
| DD114075A5 (es) | 1975-07-12 |
| GB1482771A (en) | 1977-08-17 |
| IL45298A (en) | 1980-01-31 |
| CH619213A5 (en) | 1980-09-15 |
| IE39624B1 (en) | 1978-11-22 |
| FI218874A (es) | 1975-01-19 |
| IE39624L (en) | 1975-01-18 |
| ATA596074A (de) | 1977-08-15 |
| SE7409330L (es) | 1975-01-20 |
| JPS5069072A (es) | 1975-06-09 |
| NL7409715A (nl) | 1975-01-21 |
| CA1053682A (en) | 1979-05-01 |
| FR2237628A1 (es) | 1975-02-14 |
| SE396602B (sv) | 1977-09-26 |
| DK388074A (es) | 1975-03-03 |
| CS190431B2 (en) | 1979-05-31 |
| RO72713A (ro) | 1982-09-09 |
| SU511855A3 (ru) | 1976-04-25 |
| HU173115B (hu) | 1979-02-28 |
| FR2237628B1 (es) | 1977-05-20 |
| AT342583B (de) | 1978-04-10 |
| IL45298A0 (en) | 1974-10-22 |
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