CH619213A5 - Process for the preparation of carbazole derivatives - Google Patents

Process for the preparation of carbazole derivatives Download PDF

Info

Publication number: CH619213A5
Authority: CH; Switzerland
Prior art keywords: carboxylic acid; carbazole; methyl; group; chloro
Prior art date: 1973-07-18

Application number

CH990174A

Other languages

German (de)

English (en)

Inventor

Helmut Dr Biere

Hanns Dr Ahrens

Clemens Dr Rufer

Eberhard Dr Schroeder

Henning Dr Koch

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1973-07-18

Filing date

1974-07-18

Publication date

1980-09-15

1973-07-18 Priority claimed from DE2337154A external-priority patent/DE2337154C2/de

1974-06-27 Priority claimed from DE2431292A external-priority patent/DE2431292A1/de

1974-07-18 Application filed by Schering Ag filed Critical Schering Ag

1980-09-15 Publication of CH619213A5 publication Critical patent/CH619213A5/de

Links

238000000034 method Methods 0.000 title claims description 33
238000002360 preparation method Methods 0.000 title claims description 7
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims description 3
-1 hydroxymethyl compound Chemical class 0.000 claims description 36
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
150000001298 alcohols Chemical class 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000003831 tetrazolyl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 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
229910052783 alkali metal Inorganic materials 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
239000003880 polar aprotic solvent Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
239000012024 dehydrating agents‎ Substances 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
239000000203 mixture Substances 0.000 description 26
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
239000003054 catalyst Substances 0.000 description 17
239000000243 solution Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 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
VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
230000003110 anti-inflammatory effect Effects 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
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
235000011121 sodium hydroxide Nutrition 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-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
238000010992 reflux Methods 0.000 description 6
238000003756 stirring 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
125000004494 ethyl ester group 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
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
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
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
230000002378 acidificating effect Effects 0.000 description 4
239000013543 active substance Substances 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
150000001805 chlorine compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
150000004031 phenylhydrazines Chemical class 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
239000000126 substance Substances 0.000 description 4
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 4
230000000699 topical effect Effects 0.000 description 4
WWKRQDIICDPJDD-UHFFFAOYSA-N 2-chloro-1-methyl-9H-carbazole Chemical compound ClC1=CC=C2C=3C=CC=CC3NC2=C1C WWKRQDIICDPJDD-UHFFFAOYSA-N 0.000 description 3
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 3
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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 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
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
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
239000011736 potassium bicarbonate Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
YZCKPIATAKJXRG-UHFFFAOYSA-N (7-chloro-8-methyl-9h-carbazol-1-yl)methanol Chemical compound N1C2=C(CO)C=CC=C2C2=C1C(C)=C(Cl)C=C2 YZCKPIATAKJXRG-UHFFFAOYSA-N 0.000 description 2
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
HWFUOXYUSCPVDD-UHFFFAOYSA-N 11h-benzo[a]carbazole-1-carboxylic acid Chemical compound C1=CC=C2NC3=C4C(C(=O)O)=CC=CC4=CC=C3C2=C1 HWFUOXYUSCPVDD-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
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
WPPQFLQYIQXLII-UHFFFAOYSA-N 2-(dimethylamino)ethyl 7,8-dichloro-9H-carbazole-1-carboxylate Chemical compound CN(CCOC(=O)C1=CC=CC=2C3=CC=C(C(=C3NC12)Cl)Cl)C WPPQFLQYIQXLII-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
BDONUPILRUXTQK-UHFFFAOYSA-N 4-chloro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C(Cl)=CC=C2C(=O)O BDONUPILRUXTQK-UHFFFAOYSA-N 0.000 description 2
YBBIZUZGZCWZBD-UHFFFAOYSA-N 6-fluoro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC(F)=CC=C2NC2=C1C=CC=C2C(=O)O YBBIZUZGZCWZBD-UHFFFAOYSA-N 0.000 description 2
BRYNDDZGTHSCCE-UHFFFAOYSA-N 7,8-dichloro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=C(Cl)C(Cl)=C2NC2=C1C=CC=C2C(=O)O BRYNDDZGTHSCCE-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
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
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
239000004480 active ingredient Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth 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
239000012298 atmosphere 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
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
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230000001580 bacterial effect Effects 0.000 description 1
WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
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
150000001649 bromium compounds Chemical class 0.000 description 1
PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 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
ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 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
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
125000002704 decyl 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])* 0.000 description 1
238000006356 dehydrogenation 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
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 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
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-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
VPAHJINUWOYFFG-UHFFFAOYSA-N ethyl 5-chloro-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=C(C(=CC=C3NC12)C)Cl VPAHJINUWOYFFG-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
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
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
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
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
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 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
SDNLPLNSCOFFQF-UHFFFAOYSA-N ethyl 7-fluoro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC(F)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 SDNLPLNSCOFFQF-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
DYEAIOQFDWDMLH-UHFFFAOYSA-N ethyl 8-methyl-9h-carbazole-1-carboxylate Chemical compound N1C2=C(C)C=CC=C2C2=C1C(C(=O)OCC)=CC=C2 DYEAIOQFDWDMLH-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
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 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
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])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
229960001067 hydrocortisone acetate Drugs 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
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 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
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-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
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
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
125000001400 nonyl 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])[H] 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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 Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 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
229910001923 silver oxide Inorganic materials 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
239000007858 starting material Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012085 test solution Substances 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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 Natural products 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)
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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH990174A 1973-07-18 1974-07-18 Process for the preparation of carbazole derivatives CH619213A5 (en)

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
CH619213A5 true CH619213A5 (en)	1980-09-15

Family

ID=25765532

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH990174A CH619213A5 (en)	1973-07-18	1974-07-18	Process for the preparation of carbazole derivatives

Country Status (20)

Country	Link
JP (1)	JPS5069072A (fr)
AT (1)	AT342583B (fr)
BG (1)	BG25793A3 (fr)
CA (1)	CA1053682A (fr)
CH (1)	CH619213A5 (fr)
CS (1)	CS190431B2 (fr)
DD (1)	DD114075A5 (fr)
DK (1)	DK388074A (fr)
ES (1)	ES428379A1 (fr)
FI (1)	FI218874A7 (fr)
FR (1)	FR2237628B1 (fr)
GB (1)	GB1482771A (fr)
HU (1)	HU173115B (fr)
IE (1)	IE39624B1 (fr)
IL (1)	IL45298A (fr)
NL (1)	NL7409715A (fr)
NO (1)	NO742601L (fr)
RO (1)	RO72713A (fr)
SE (1)	SE396602B (fr)
SU (1)	SU511855A3 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ533430A (en) *	2001-12-14	2005-12-23	Zentaris Gmbh	Tetrahydrocarbozole derivatives as ligands for G-protein coupled receptors (GPCR)
CA2538759C (fr) *	2003-09-12	2015-11-03	Elixir Pharmaceuticals, Inc.	Composes heterocycliques substitues en tant qu'inhibiteurs de sirtuines
US20060074124A1 (en) *	2003-09-12	2006-04-06	Andrew Napper	Methods of treating a disorder
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
CN110753683B (zh) *	2017-04-11	2024-02-09	吉斯诺治疗公司	咔唑化合物及其使用方法
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7008628A (fr) *	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 NO NO742601A patent/NO742601L/no unknown
- 1974-07-17 HU HU24SC483A patent/HU173115B/hu unknown
- 1974-07-17 FI FI2188/74A patent/FI218874A7/fi unknown
- 1974-07-17 CS CS745109A patent/CS190431B2/cs unknown
- 1974-07-17 SE SE7409330A patent/SE396602B/xx unknown
- 1974-07-18 DK DK388074A patent/DK388074A/da not_active Application Discontinuation
- 1974-07-18 CA CA205,063A patent/CA1053682A/fr not_active Expired
- 1974-07-18 IL IL45298A patent/IL45298A/xx unknown
- 1974-07-18 IE IE1519/74A patent/IE39624B1/xx unknown
- 1974-07-18 SU SU2048652A patent/SU511855A3/ru active
- 1974-07-18 NL NL7409715A patent/NL7409715A/xx not_active Application Discontinuation
- 1974-07-18 RO RO7479524A patent/RO72713A/fr unknown
- 1974-07-18 GB GB31966/74A patent/GB1482771A/en not_active Expired
- 1974-07-18 FR FR7424991A patent/FR2237628B1/fr not_active Expired
- 1974-07-18 AT AT596074A patent/AT342583B/de active
- 1974-07-18 CH CH990174A patent/CH619213A5/de not_active IP Right Cessation
- 1974-07-18 JP JP49082669A patent/JPS5069072A/ja active Pending

Also Published As

Publication number	Publication date
IE39624B1 (en)	1978-11-22
IE39624L (en)	1975-01-18
FR2237628A1 (fr)	1975-02-14
SE7409330L (fr)	1975-01-20
CA1053682A (fr)	1979-05-01
DD114075A5 (fr)	1975-07-12
JPS5069072A (fr)	1975-06-09
SE396602B (sv)	1977-09-26
RO72713A (fr)	1982-09-09
AT342583B (de)	1978-04-10
ES428379A1 (es)	1976-09-16
IL45298A (en)	1980-01-31
FI218874A7 (fr)	1975-01-19
NL7409715A (nl)	1975-01-21
ATA596074A (de)	1977-08-15
BG25793A3 (bg)	1978-12-12
FR2237628B1 (fr)	1977-05-20
HU173115B (hu)	1979-02-28
CS190431B2 (en)	1979-05-31
SU511855A3 (ru)	1976-04-25
GB1482771A (en)	1977-08-17
IL45298A0 (en)	1974-10-22
NO742601L (fr)	1975-02-17
DK388074A (fr)	1975-03-03

Legal Events

Date	Code	Title	Description
1990-03-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3324034C2 (fr)	1993-07-01
DD207714A5 (de)	1984-03-14	Verfahren zur herstellung von benzimidazolen
DE2162595A1 (de)	1972-07-06	Steroide der Androstanreihe und Verfahren zu ihrer Herstellung
DE1770595A1 (de)	1972-03-02	Substituierte Tetrahydrochinoline
CH619213A5 (en)	1980-09-15	Process for the preparation of carbazole derivatives
DE3103372A1 (de)	1982-09-02	Neue indanyl-derivate, ihre herstellung und verwendung
DE2431292A1 (de)	1976-01-15	Neue carbazol-derivate
EP0072960B1 (fr)	1989-06-07	Composés 1,5-diphénylpyrazolin-3-one, ainsi qu'un procédé et produits intermédiaires pour leur fabrication et médicaments contenant ces composés
EP0576906A1 (fr)	1994-01-05	Dérivés et thiénothiazine, procédé pour leur préparation et leur utilisation comme agents anti-inflammatoires et analgésiques.
EP0062919B1 (fr)	1986-07-30	Dérivés indoliques, procédé pour leur préparation et préparations pharmaceutiques les contenant
AT234103B (de)	1964-06-10	Verfahren zur Herstellung von neuen, benzylindolylsubstituierten niedrigen aliphatischen Säuren sowie deren Salzen und Estern
CH618447A5 (en)	1980-07-31	Process for the preparation of pregnanoic acid derivatives.
DE2427272A1 (de)	1976-01-08	1-(2-(beta-naphthyloxy)-aethyl)-3-methyl -pyrazolon-(5), verfahren sowie verwendung als antithrombotikum
DE2438019A1 (de)	1976-02-19	Neue carbazol-derivate
DE2137538A1 (de)	1972-06-29	Methoxyaminderivate und ihre Salze sowie ihre Verwendimg und Verfahren zur Herstellung derselben
DE2438018A1 (de)	1976-02-26	Neue carbazol-derivate
DE2640022A1 (de)	1977-03-24	Neue organische verbindungen, ihre herstellung und verwendung
DE2440880A1 (de)	1976-03-04	Neue 5, 6, 7, 8-tetrahydro-carbazolderivate
DE3020895A1 (de)	1980-12-18	Ergopeptinderivate, verfahren zu deren herstellung sowie diese ergopeptinderivate enthaltende pharmazeutischen zusammensetzungen
DD246299A5 (de)	1987-06-03	Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten
DE2029185A1 (en)	1971-12-30	2-azaquinolizidine derivs and salts neurotropic and anti - -histamine agents synthesis
DE2438021A1 (de)	1976-02-19	Neue carbazol-derivate
AT374166B (de)	1984-03-26	Verfahren zur herstellung von neuen indan-1 -carbonsaeure-derivaten und deren salzen
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
EP0008439A1 (fr)	1980-03-05	Hétérocycles pyraniques, procédé pour leur préparation et médicaments les contenant