DD202541A5 - Verfahren zur herstellung neuer indol-derivate - Google Patents

Verfahren zur herstellung neuer indol-derivate Download PDF

Info

Publication number: DD202541A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroxy; preparation; carboxylic acid; indole derivatives; indole
Prior art date: 1981-04-13

Application number

DD82238923A

Other languages

German (de)

English (en)

Inventor

Josef Heindl

Olaf Loge

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.)

1981-04-13

Filing date

1982-04-12

Publication date

1983-09-21

1982-04-12 Application filed by Schering Ag filed Critical Schering Ag

1983-09-21 Publication of DD202541A5 publication Critical patent/DD202541A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 59
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 3
150000002475 indoles Chemical class 0.000 claims abstract description 71
229940054051 antipsychotic indole derivative Drugs 0.000 claims abstract description 67
238000002360 preparation method Methods 0.000 claims abstract description 56
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
-1 alkyl radical Chemical class 0.000 claims description 132
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 89
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
OZMHRSZELZSVOX-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-1h-indole-2-carboxylic acid Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C2=C1C=C(C(O)=O)N2 OZMHRSZELZSVOX-UHFFFAOYSA-N 0.000 claims description 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
YWZRVEHFRBJSNL-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-1h-indole-2-carboxylate Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C2=C1C=C(C(=O)OCOC(=O)C(C)(C)C)N2 YWZRVEHFRBJSNL-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
GXSNKCVLJLJQCE-UHFFFAOYSA-N methyl 7-hydroxy-4-[1-hydroxy-2-(propan-2-ylamino)ethyl]-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OC)=CC2=C1C(O)CNC(C)C GXSNKCVLJLJQCE-UHFFFAOYSA-N 0.000 claims description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
125000004430 oxygen atom Chemical group O* 0.000 claims 2
HCUARRIEZVDMPT-UHFFFAOYSA-M 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)[O-])=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-M 0.000 claims 1
GIAAXCHYIFQRDK-UHFFFAOYSA-N 2-methylpropyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC(C)C)=CC2=C1C(O)CNC(C)(C)C GIAAXCHYIFQRDK-UHFFFAOYSA-N 0.000 claims 1
TUHBKHGVGKFOEQ-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-3-methyl-1h-indole-2-carboxylic acid Chemical compound C1=CC(C(O)CNC(C)(C)C)=C2C(C)=C(C(O)=O)NC2=C1O TUHBKHGVGKFOEQ-UHFFFAOYSA-N 0.000 claims 1
ZAIQWZQZEACHMP-UHFFFAOYSA-N 7-hydroxy-4-[1-hydroxy-2-(propan-2-ylamino)ethyl]-1h-indole-2-carboxylic acid Chemical compound CC(C)NCC(O)C1=CC=C(O)C2=C1C=C(C(O)=O)N2 ZAIQWZQZEACHMP-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
VNXWRUKGRLHMIT-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-3-methyl-1h-indole-2-carboxylate Chemical compound C1=CC(C(O)CNC(C)(C)C)=C2C(C)=C(C(=O)OCC)NC2=C1O VNXWRUKGRLHMIT-UHFFFAOYSA-N 0.000 claims 1
CSWKHWVEQGIFDC-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)-1-hydroxypropyl]-7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(O)C(C)NC(C)(C)C CSWKHWVEQGIFDC-UHFFFAOYSA-N 0.000 claims 1
229960002449 glycine Drugs 0.000 claims 1
235000013905 glycine and its sodium salt Nutrition 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
DUSHTEPQQPPJOO-UHFFFAOYSA-N methyl 7-hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]-1h-indole-2-carboxylate Chemical compound CNCC(O)C1=CC=C(O)C2=C1C=C(C(=O)OC)N2 DUSHTEPQQPPJOO-UHFFFAOYSA-N 0.000 claims 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
IOUZKKPQVTZQMK-UHFFFAOYSA-N phenyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-1h-indole-2-carboxylate Chemical compound C=1C=2C(C(O)CNC(C)(C)C)=CC=C(O)C=2NC=1C(=O)OC1=CC=CC=C1 IOUZKKPQVTZQMK-UHFFFAOYSA-N 0.000 claims 1
125000003884 phenylalkyl group Chemical group 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
238000001228 spectrum Methods 0.000 abstract description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
238000000354 decomposition reaction Methods 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
239000000243 solution Substances 0.000 description 58
239000000203 mixture Substances 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 40
238000002844 melting Methods 0.000 description 39
230000008018 melting Effects 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000012074 organic phase Substances 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
229960000583 acetic acid Drugs 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
150000002148 esters Chemical class 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
125000004494 ethyl ester group Chemical group 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000001816 cooling Methods 0.000 description 15
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
229910000041 hydrogen chloride Inorganic materials 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 11
239000005457 ice water Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
SUFWHESGARMYGI-UHFFFAOYSA-N ethyl 7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1 SUFWHESGARMYGI-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
WTGNOVIRAWZGDI-UHFFFAOYSA-N 2-(tert-butylamino)acetonitrile;hydrochloride Chemical compound Cl.CC(C)(C)NCC#N WTGNOVIRAWZGDI-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007789 gas Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
MUKNVPMLFAHORL-UHFFFAOYSA-N 7-phenylmethoxy-1h-indole-2-carboxylic acid Chemical compound C=12NC(C(=O)O)=CC2=CC=CC=1OCC1=CC=CC=C1 MUKNVPMLFAHORL-UHFFFAOYSA-N 0.000 description 5
239000012043 crude product Substances 0.000 description 5
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
QGDXKXZQRVFNAI-UHFFFAOYSA-N ethyl 4-(2-chloroacetyl)-7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CCl QGDXKXZQRVFNAI-UHFFFAOYSA-N 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
VQTQDVYIDANALW-UHFFFAOYSA-N methyl 7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OC)=CC2=C1 VQTQDVYIDANALW-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JGBRHQMNPJTBHP-UHFFFAOYSA-N 4-[2-[benzyl(tert-butyl)amino]acetyl]-7-phenylmethoxy-1h-indole-2-carboxylic acid;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CN(C(C)(C)C)CC(=O)C(C=1C=C(NC=11)C(O)=O)=CC=C1OCC1=CC=CC=C1 JGBRHQMNPJTBHP-UHFFFAOYSA-N 0.000 description 3
RKTALADUQKJJKU-UHFFFAOYSA-N 7-hydroxy-1h-indole-2-carboxylic acid Chemical compound C1=CC(O)=C2NC(C(=O)O)=CC2=C1 RKTALADUQKJJKU-UHFFFAOYSA-N 0.000 description 3
WYPRTJYUDCZXGF-UHFFFAOYSA-N 7-methoxy-1h-indole-2-carboxylic acid Chemical compound COC1=CC=CC2=C1NC(C(O)=O)=C2 WYPRTJYUDCZXGF-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
QHFOBIBNEVLXKO-UHFFFAOYSA-N butyl 7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCCCC)=CC2=C1 QHFOBIBNEVLXKO-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
OMKLIYMSJTUMRD-UHFFFAOYSA-N methyl 7-methoxy-1h-indole-2-carboxylate Chemical compound C1=CC(OC)=C2NC(C(=O)OC)=CC2=C1 OMKLIYMSJTUMRD-UHFFFAOYSA-N 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
ZUMJNYJMXBJJIC-UHFFFAOYSA-N 1-methyl-2-nitro-3-phenylmethoxybenzene Chemical compound CC1=CC=CC(OCC=2C=CC=CC=2)=C1[N+]([O-])=O ZUMJNYJMXBJJIC-UHFFFAOYSA-N 0.000 description 2
JVCSBFUJXVCBCX-UHFFFAOYSA-N 2-[benzyl(tert-butyl)amino]-1-[2-(hydroxymethyl)-7-phenylmethoxy-1h-indol-4-yl]ethanol Chemical compound C=1C=CC=CC=1CN(C(C)(C)C)CC(O)C(C=1C=C(CO)NC=11)=CC=C1OCC1=CC=CC=C1 JVCSBFUJXVCBCX-UHFFFAOYSA-N 0.000 description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
GBPCJHMDQYTRED-UHFFFAOYSA-N 2-methylpropyl 7-methoxy-1h-indole-2-carboxylate Chemical compound COC1=CC=CC2=C1NC(C(=O)OCC(C)C)=C2 GBPCJHMDQYTRED-UHFFFAOYSA-N 0.000 description 2
GWERANXNSVPLHE-UHFFFAOYSA-N 3-[benzyl(cyanomethyl)amino]butanoic acid Chemical compound OC(=O)CC(C)N(CC#N)CC1=CC=CC=C1 GWERANXNSVPLHE-UHFFFAOYSA-N 0.000 description 2
OZABZEVAOKMZMQ-UHFFFAOYSA-N 7-phenylmethoxy-1h-indole-4-carbaldehyde Chemical compound C1=2NC=CC=2C(C=O)=CC=C1OCC1=CC=CC=C1 OZABZEVAOKMZMQ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
VWGUYTTWHKXVEV-UHFFFAOYSA-N acetyloxymethyl 7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCOC(=O)C)=CC2=C1 VWGUYTTWHKXVEV-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
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LWNWDYCNTNSQCL-UHFFFAOYSA-N ethyl 4-[2-(cyclohexylamino)acetyl]-7-hydroxy-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CNC1CCCCC1 LWNWDYCNTNSQCL-UHFFFAOYSA-N 0.000 description 1
NJKLOTUTUUVPFG-UHFFFAOYSA-N ethyl 4-[2-(cyclohexylamino)acetyl]-7-hydroxy-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CNC1CCCCC1 NJKLOTUTUUVPFG-UHFFFAOYSA-N 0.000 description 1
UOQWEZAEHZTEJX-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-3-methyl-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(C(O)CNC(C)(C)C)=C2C(C)=C(C(=O)OCC)NC2=C1O UOQWEZAEHZTEJX-UHFFFAOYSA-N 0.000 description 1
CPSNZNROGIKVHW-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)-1-hydroxypropyl]-7-hydroxy-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(O)C(C)NC(C)(C)C CPSNZNROGIKVHW-UHFFFAOYSA-N 0.000 description 1
MBQKMUKASWOZFX-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)acetyl]-7-hydroxy-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CNC(C)(C)C MBQKMUKASWOZFX-UHFFFAOYSA-N 0.000 description 1
XZSQSSZIHGUSGI-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)acetyl]-7-hydroxy-3-methyl-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(C(=O)CNC(C)(C)C)=C2C(C)=C(C(=O)OCC)NC2=C1O XZSQSSZIHGUSGI-UHFFFAOYSA-N 0.000 description 1
NOUVPQOQKXOKEW-UHFFFAOYSA-N ethyl 4-[2-[benzyl(tert-butyl)amino]acetyl]-7-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=12NC(C(=O)OCC)=CC2=C(C(=O)CN(CC=2C=CC=CC=2)C(C)(C)C)C=CC=1OCC1=CC=CC=C1 NOUVPQOQKXOKEW-UHFFFAOYSA-N 0.000 description 1
RORNLMUSCTUNOH-UHFFFAOYSA-N ethyl 4-[2-[benzyl-(4-methoxy-4-oxobutan-2-yl)amino]acetyl]-7-hydroxy-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CN(C(C)CC(=O)OC)CC1=CC=CC=C1 RORNLMUSCTUNOH-UHFFFAOYSA-N 0.000 description 1
ZGRDQOHQYOADFX-UHFFFAOYSA-N ethyl 4-formyl-7-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=12NC(C(=O)OCC)=CC2=C(C=O)C=CC=1OCC1=CC=CC=C1 ZGRDQOHQYOADFX-UHFFFAOYSA-N 0.000 description 1
LLQYDPSCYTXRPX-UHFFFAOYSA-N ethyl 7-hydroxy-4-[2-[(4-oxo-4-phenylmethoxybutan-2-yl)amino]acetyl]-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2NC(C(=O)OCC)=CC2=C1C(=O)CNC(C)CC(=O)OCC1=CC=CC=C1 LLQYDPSCYTXRPX-UHFFFAOYSA-N 0.000 description 1
IMKSDZLFVYKGLY-UHFFFAOYSA-N ethyl 7-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=12NC(C(=O)OCC)=CC2=CC=CC=1OCC1=CC=CC=C1 IMKSDZLFVYKGLY-UHFFFAOYSA-N 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DFKBQHBEROHUNF-UHFFFAOYSA-N hydron;2-(methylamino)acetonitrile;chloride Chemical compound Cl.CNCC#N DFKBQHBEROHUNF-UHFFFAOYSA-N 0.000 description 1
DLDIDQIZPBIVNQ-UHFFFAOYSA-N hydron;2-methylpropan-2-amine;chloride Chemical compound Cl.CC(C)(C)N DLDIDQIZPBIVNQ-UHFFFAOYSA-N 0.000 description 1
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 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 class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960003134 mepindolol Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
ZHSDERYVVFKJSD-UHFFFAOYSA-N methoxymethyl 4-[2-[benzyl(tert-butyl)amino]acetyl]-7-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=12NC(C(=O)OCOC)=CC2=C(C(=O)CN(CC=2C=CC=CC=2)C(C)(C)C)C=CC=1OCC1=CC=CC=C1 ZHSDERYVVFKJSD-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
SKRWNEIVFJUNNN-UHFFFAOYSA-N methyl 3-[benzyl(cyanomethyl)amino]butanoate Chemical compound COC(=O)CC(C)N(CC#N)CC1=CC=CC=C1 SKRWNEIVFJUNNN-UHFFFAOYSA-N 0.000 description 1
GTAJQPCNVKWQTN-UHFFFAOYSA-N methyl 4-(2-bromoacetyl)-7-methoxy-1h-indole-2-carboxylate Chemical compound C1=CC(OC)=C2NC(C(=O)OC)=CC2=C1C(=O)CBr GTAJQPCNVKWQTN-UHFFFAOYSA-N 0.000 description 1
BZVWFZUVKYWJCH-UHFFFAOYSA-N methyl 4-[2-(tert-butylamino)-1-hydroxyethyl]-7-hydroxy-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(O)=C2NC(C(=O)OC)=CC2=C1C(O)CNC(C)(C)C BZVWFZUVKYWJCH-UHFFFAOYSA-N 0.000 description 1
NIPDBPIDJFXULF-UHFFFAOYSA-N methyl 7-hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]-1h-indole-2-carboxylate;hydrochloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C2=C1C=C(C(=O)OC)N2 NIPDBPIDJFXULF-UHFFFAOYSA-N 0.000 description 1
KNXBLEKQEBTKCB-UHFFFAOYSA-N n',n'-dibenzylhexane-1,6-diamine Chemical compound C=1C=CC=CC=1CN(CCCCCCN)CC1=CC=CC=C1 KNXBLEKQEBTKCB-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 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
229910017604 nitric acid Inorganic materials 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
WWIACWWKSXPEKU-UHFFFAOYSA-N phenyl 7-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=1C2=CC=CC(OCC=3C=CC=CC=3)=C2NC=1C(=O)OC1=CC=CC=C1 WWIACWWKSXPEKU-UHFFFAOYSA-N 0.000 description 1
JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
229910052697 platinum Inorganic materials 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
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
208000026440 premature labor Diseases 0.000 description 1
239000003380 propellant Substances 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 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
229940110410 thylox Drugs 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD82238923A 1981-04-13 1982-04-12 Verfahren zur herstellung neuer indol-derivate DD202541A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813115993 DE3115993A1 (de)	1981-04-13	1981-04-13	Neue indol-derivate, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten

Publications (1)

Publication Number	Publication Date
DD202541A5 true DD202541A5 (de)	1983-09-21

Family

ID=6130597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82238923A DD202541A5 (de)	1981-04-13	1982-04-12	Verfahren zur herstellung neuer indol-derivate

Country Status (19)

Country	Link
US (1)	US4835175A (fr)
EP (1)	EP0062919B1 (fr)
JP (1)	JPS584765A (fr)
AT (1)	ATE21100T1 (fr)
AU (1)	AU559684B2 (fr)
CA (1)	CA1202972A (fr)
DD (1)	DD202541A5 (fr)
DE (2)	DE3115993A1 (fr)
DK (1)	DK155280C (fr)
ES (1)	ES8303335A1 (fr)
GB (1)	GB2098205A (fr)
GR (1)	GR75471B (fr)
HU (1)	HU187675B (fr)
IE (1)	IE52875B1 (fr)
IL (1)	IL65483A0 (fr)
NO (1)	NO158940C (fr)
NZ (1)	NZ200258A (fr)
PT (1)	PT74732B (fr)
ZA (1)	ZA822488B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3440881A1 (de) *	1984-11-06	1986-05-15	Schering AG, Berlin und Bergkamen, 1000 Berlin	Pharmazeutische zusammensetzung, ihre herstellung und verwendung
JP2750441B2 (ja) *	1988-02-24	1998-05-13	川研ファインケミカル株式会社	７―ヒドロキシインドール―２―カルボン酸化合物の製造方法
GB9716657D0 (en) *	1997-08-07	1997-10-15	Zeneca Ltd	Chemical compounds
WO2002097923A1 (fr) *	2001-04-28	2002-12-05	Anyans	Antenne en coin
CA3130291A1 (fr)	2019-03-27	2020-10-01	Anthony P. FORD	Agonistes beta-adrenergique et leurs procedes d'utilisation
EP3993878A4 (fr) *	2019-07-01	2023-11-08	Curasen Therapeutics, Inc.	Agoniste bêta-adrénergique et procédés d'utilisation associés

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1532210A (fr) *	1963-06-21	1968-07-12	Ici Ltd	Composés hétérocycliques et leur procédé de préparation
BE754360A (fr) *	1969-08-05	1971-02-03	Sandoz Sa	Nouveaux derives de l'indole, leur preparation et medicaments contenantdes derives
US3705907A (en) *	1970-02-19	1972-12-12	Sandoz Ltd	4-(2-hydroxy)-3-aminopropoxy)-indole derivatives
US4076829A (en) *	1974-11-16	1978-02-28	Boehringer Mannheim Gmbh	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
FR2370472A2 (fr) *	1976-11-10	1978-06-09	Continental Pharma	Amino-alcool heterocyclique, son sel et son procede de preparation
WO1980000152A1 (fr) *	1978-07-03	1980-02-07	Sandoz Ag	Derives d'un 3-aminopropoxy-aryle, leur preparation et utilisation

1981
- 1981-04-13 DE DE19813115993 patent/DE3115993A1/de not_active Withdrawn
1982
- 1982-04-06 NO NO821168A patent/NO158940C/no unknown
- 1982-04-07 ES ES511255A patent/ES8303335A1/es not_active Expired
- 1982-04-07 NZ NZ200258A patent/NZ200258A/en unknown
- 1982-04-08 IE IE851/82A patent/IE52875B1/en unknown
- 1982-04-08 CA CA000400813A patent/CA1202972A/fr not_active Expired
- 1982-04-08 AU AU82509/82A patent/AU559684B2/en not_active Ceased
- 1982-04-08 PT PT74732A patent/PT74732B/pt unknown
- 1982-04-09 HU HU821105A patent/HU187675B/hu not_active IP Right Cessation
- 1982-04-12 IL IL65483A patent/IL65483A0/xx unknown
- 1982-04-12 JP JP57060854A patent/JPS584765A/ja active Pending
- 1982-04-12 DD DD82238923A patent/DD202541A5/de not_active IP Right Cessation
- 1982-04-13 GB GB8210671A patent/GB2098205A/en not_active Withdrawn
- 1982-04-13 ZA ZA822488A patent/ZA822488B/xx unknown
- 1982-04-13 EP EP82103106A patent/EP0062919B1/fr not_active Expired
- 1982-04-13 GR GR67916A patent/GR75471B/el unknown
- 1982-04-13 DE DE8282103106T patent/DE3272264D1/de not_active Expired
- 1982-04-13 AT AT82103106T patent/ATE21100T1/de not_active IP Right Cessation
- 1982-04-13 DK DK164282A patent/DK155280C/da active
1986
- 1986-10-10 US US06/917,445 patent/US4835175A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA1202972A (fr)	1986-04-08
NO158940B (no)	1988-08-08
IE820851L (en)	1982-10-13
ATE21100T1 (de)	1986-08-15
ES511255A0 (es)	1983-02-16
US4835175A (en)	1989-05-30
DK155280B (da)	1989-03-20
EP0062919B1 (fr)	1986-07-30
IL65483A0 (en)	1982-07-30
HU187675B (en)	1986-02-28
NO821168L (no)	1982-10-14
JPS584765A (ja)	1983-01-11
PT74732A (de)	1982-05-01
AU559684B2 (en)	1987-03-19
GB2098205A (en)	1982-11-17
DK155280C (da)	1989-08-07
NZ200258A (en)	1985-11-08
DE3115993A1 (de)	1982-11-11
AU8250982A (en)	1983-04-21
ES8303335A1 (es)	1983-02-16
DK164282A (da)	1982-10-14
NO158940C (no)	1988-11-16
IE52875B1 (en)	1988-03-30
GR75471B (fr)	1984-07-23
EP0062919A1 (fr)	1982-10-20
PT74732B (de)	1983-11-09
ZA822488B (en)	1983-02-23
DE3272264D1 (en)	1986-09-04

Legal Events

Date	Code	Title	Description
1996-02-01	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0079022B1 (fr)	1986-03-12	Dérivés de l'acide cis, endo-2-azabicyclo-(3.3.0)-octane-3-carboxylique, procédé pour leur préparation, medicaments les contenant et leur application
CH651561A5 (fr)	1985-09-30	Derives des nor-tropane et granatane et leur procede de preparation.
CH621115A5 (fr)	1981-01-15
DE69002474T2 (de)	1994-03-10	Carboxyalkyl-ether von 2-Amino-7-hydroxytetralin.
DD202541A5 (de)	1983-09-21	Verfahren zur herstellung neuer indol-derivate
EP0065295A1 (fr)	1982-11-24	Dérivés de la tryptamine et de la thiényloxypropanolamine, procédé pour leur préparation, compositions pharmaceutiques les contenant et préparation de celles-ci
IL27871A (en)	1971-05-26	History of benzomorphan and their preparation
EP0253171A1 (fr)	1988-01-20	Pyrido[1,8]naphtyridinones, leur procédé de préparation, leur utilisation et compositions les contenant
DE60112917T2 (de)	2006-06-08	Neue polyzyklische indanylimidazole mit alpha2 adrenergik aktivität
EP0071950B1 (fr)	1985-11-06	Hétéroarylpropanolamines, procédé pour leur fabrication et médicaments contenant ces composés
CH619213A5 (en)	1980-09-15	Process for the preparation of carbazole derivatives
JPH037280A (ja)	1991-01-14	新規ベンゾチオピラニルアミン
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