DK174104B1 - 1-Tetrazol-5-yl-1H-indol-carboxamidderivater, fremgangsmåde til fremstilling deraf samt lægemidde indeholdende forbindelserne - Google Patents

1-Tetrazol-5-yl-1H-indol-carboxamidderivater, fremgangsmåde til fremstilling deraf samt lægemidde indeholdende forbindelserne Download PDF

Info

Publication number: DK174104B1
Authority: DK; Denmark
Prior art keywords: indole; carbon atoms; methoxy; carboxamide; phenyl
Prior art date: 1984-12-10

Application number

DK198505688A

Other languages

Danish (da)

English (en)

Other versions

DK568885A (da

DK568885D0 (da

Inventor

David T Connor

Paul C Unangst

S Russell Stabler

Original Assignee

Warner Lambert Co

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.)

1984-12-10

Filing date

1985-12-09

Publication date

2002-06-17

1985-12-09 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1985-12-09 Publication of DK568885D0 publication Critical patent/DK568885D0/da

1986-06-11 Publication of DK568885A publication Critical patent/DK568885A/da

2002-06-17 Application granted granted Critical

2002-06-17 Publication of DK174104B1 publication Critical patent/DK174104B1/da

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 76
238000000034 method Methods 0.000 title claims abstract description 44
230000008569 process Effects 0.000 title claims description 16
239000003814 drug Substances 0.000 title claims description 9
229940079593 drug Drugs 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 9
ZZDYHKJHPYLPJP-UHFFFAOYSA-N 1-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical class NC(=O)C1=CC2=CC=CC=C2N1C=1N=NNN=1 ZZDYHKJHPYLPJP-UHFFFAOYSA-N 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
-1 phenylsulphinyl radical Chemical class 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
AHVDOZRFBYRTKI-UHFFFAOYSA-N 3-ethoxy-5-methoxy-1-phenyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=C(OC)C=C2C(OCC)=C1C(=O)NC1=NN=NN1 AHVDOZRFBYRTKI-UHFFFAOYSA-N 0.000 claims description 4
JPTSIWRGXIZEOO-UHFFFAOYSA-N 5-methoxy-1-phenyl-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound CC(C)OC=1C2=CC(OC)=CC=C2N(C=2C=CC=CC=2)C=1C(=O)NC=1N=NNN=1 JPTSIWRGXIZEOO-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 3
239000007822 coupling agent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
NPOKKFJYMVHFBO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C2=CC=CC=C2C(OC(C)C)=C1C(=O)NC1=NN=NN1 NPOKKFJYMVHFBO-UHFFFAOYSA-N 0.000 claims description 2
SJRFJXUBFIIOQZ-UHFFFAOYSA-N 1-hexyl-3-methoxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound COC=1C2=CC=CC=C2N(CCCCCC)C=1C(=O)NC1=NN=NN1 SJRFJXUBFIIOQZ-UHFFFAOYSA-N 0.000 claims description 2
CJEQMVATXGSTRF-UHFFFAOYSA-N 1-phenyl-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=CC=C2C(OC(C)C)=C1C(=O)NC1=NN=NN1 CJEQMVATXGSTRF-UHFFFAOYSA-N 0.000 claims description 2
RNGDPHCTXKJOLI-UHFFFAOYSA-N 3,5-dimethoxy-1-phenyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=C(OC)C=C2C(OC)=C1C(=O)NC1=NN=NN1 RNGDPHCTXKJOLI-UHFFFAOYSA-N 0.000 claims description 2
HNKSRMIFSKKVAV-UHFFFAOYSA-N 5-methoxy-1-phenyl-3-phenylsulfanyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1SC=1C2=CC(OC)=CC=C2N(C=2C=CC=CC=2)C=1C(=O)NC1=NN=NN1 HNKSRMIFSKKVAV-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
GSOZKZKVLAUSAO-UHFFFAOYSA-N 3-dodecoxy-5-methoxy-1-phenyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=C(OC)C=C2C(OCCCCCCCCCCCC)=C1C(=O)NC=1N=NNN=1 GSOZKZKVLAUSAO-UHFFFAOYSA-N 0.000 claims 1
JUBKTWNCZBINGT-UHFFFAOYSA-N 3-methoxy-1-methyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical group CN1C2=CC=CC=C2C(OC)=C1C(=O)NC1=NN=NN1 JUBKTWNCZBINGT-UHFFFAOYSA-N 0.000 claims 1
MTZZZDXBMDXTQP-UHFFFAOYSA-N 3-methoxy-1-nonyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound COC=1C2=CC=CC=C2N(CCCCCCCCC)C=1C(=O)NC1=NN=NN1 MTZZZDXBMDXTQP-UHFFFAOYSA-N 0.000 claims 1
ZIYWYFBDWAGNLP-UHFFFAOYSA-N 3-methoxy-1-phenyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=CC=C2C(OC)=C1C(=O)NC1=NN=NN1 ZIYWYFBDWAGNLP-UHFFFAOYSA-N 0.000 claims 1
KFRYVBYOSYNWSQ-UHFFFAOYSA-N 3-methoxy-n-(2h-tetrazol-5-yl)-1h-indole-2-carboxamide Chemical group N1C2=CC=CC=C2C(OC)=C1C(=O)NC1=NN=NN1 KFRYVBYOSYNWSQ-UHFFFAOYSA-N 0.000 claims 1
XMYUQMPYLKXPAK-UHFFFAOYSA-N 5-chloro-1-phenyl-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=C(Cl)C=C2C(OC(C)C)=C1C(=O)NC1=NN=NN1 XMYUQMPYLKXPAK-UHFFFAOYSA-N 0.000 claims 1
RYOUDBDJJZJETN-UHFFFAOYSA-N 5-methoxy-1-methyl-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound CC(C)OC=1C2=CC(OC)=CC=C2N(C)C=1C(=O)NC=1N=NNN=1 RYOUDBDJJZJETN-UHFFFAOYSA-N 0.000 claims 1
UFGNCIJPKYWKPU-UHFFFAOYSA-N 5-methoxy-3-nonoxy-1-phenyl-n-(2h-tetrazol-5-yl)indole-2-carboxamide Chemical compound C=1C=CC=CC=1N1C2=CC=C(OC)C=C2C(OCCCCCCCCC)=C1C(=O)NC1=NN=NN1 UFGNCIJPKYWKPU-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 34
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 abstract description 3
125000003277 amino group Chemical group 0.000 abstract 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
150000003254 radicals Chemical class 0.000 abstract 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 32
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000000543 intermediate Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000000354 decomposition reaction Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
125000000623 heterocyclic group Chemical group 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000000746 purification Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
230000003266 anti-allergic effect Effects 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000020477 pH reduction Effects 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
FLABMTVDNODXQV-UHFFFAOYSA-N 2h-tetrazole-5-carboxamide Chemical compound NC(=O)C=1N=NNN=1 FLABMTVDNODXQV-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
210000003630 histaminocyte Anatomy 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
239000005457 ice water Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
CQVGHRNBLPXJBR-UHFFFAOYSA-N methyl 3-hydroxy-5-methoxy-1-phenylindole-2-carboxylate Chemical compound COC(=O)C1=C(O)C2=CC(OC)=CC=C2N1C1=CC=CC=C1 CQVGHRNBLPXJBR-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 2
MDIIHSHYJROUBF-UHFFFAOYSA-N 1-phenyl-3-propan-2-yloxyindole-2-carboxylic acid Chemical compound C12=CC=CC=C2C(OC(C)C)=C(C(O)=O)N1C1=CC=CC=C1 MDIIHSHYJROUBF-UHFFFAOYSA-N 0.000 description 2
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 2
TYSMHDXGGFSMQF-UHFFFAOYSA-N 5-chloro-1-phenyl-3-propan-2-yloxyindole-2-carboxylic acid Chemical compound C12=CC=C(Cl)C=C2C(OC(C)C)=C(C(O)=O)N1C1=CC=CC=C1 TYSMHDXGGFSMQF-UHFFFAOYSA-N 0.000 description 2
UUDMVVSMLJIBTQ-UHFFFAOYSA-N 5-methoxy-3-nonoxy-1-phenylindole-2-carboxylic acid Chemical compound C12=CC=C(OC)C=C2C(OCCCCCCCCC)=C(C(O)=O)N1C1=CC=CC=C1 UUDMVVSMLJIBTQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical class OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
229930064664 L-arginine Chemical class 0.000 description 2
235000014852 L-arginine Nutrition 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 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
230000000172 allergic effect Effects 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
239000002585 base Substances 0.000 description 2
210000003651 basophil Anatomy 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 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
210000004027 cell Anatomy 0.000 description 2
238000001816 cooling Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000002475 indoles Chemical class 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
WIHCDHFIANBLMI-UHFFFAOYSA-N methyl 3-hydroxy-1-phenylindole-2-carboxylate Chemical compound COC(=O)C1=C(O)C2=CC=CC=C2N1C1=CC=CC=C1 WIHCDHFIANBLMI-UHFFFAOYSA-N 0.000 description 2
ZNFVMWVZTJQTKL-UHFFFAOYSA-N methyl 5-methoxy-1-methyl-3-propan-2-yloxyindole-2-carboxylate Chemical compound COC1=CC=C2N(C)C(C(=O)OC)=C(OC(C)C)C2=C1 ZNFVMWVZTJQTKL-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
210000000440 neutrophil Anatomy 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Lubricants (AREA)
Cosmetics (AREA)

DK198505688A 1984-12-10 1985-12-09 1-Tetrazol-5-yl-1H-indol-carboxamidderivater, fremgangsmåde til fremstilling deraf samt lægemidde indeholdende forbindelserne DK174104B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US68011684A	1984-12-10	1984-12-10
US68011684		1984-12-10
US78811185		1985-10-21
US06/788,111 US4675332A (en)	1984-12-10	1985-10-21	Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents

Publications (3)

Publication Number	Publication Date
DK568885D0 DK568885D0 (da)	1985-12-09
DK568885A DK568885A (da)	1986-06-11
DK174104B1 true DK174104B1 (da)	2002-06-17

Family

ID=27102395

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198505688A DK174104B1 (da)	1984-12-10	1985-12-09	1-Tetrazol-5-yl-1H-indol-carboxamidderivater, fremgangsmåde til fremstilling deraf samt lægemidde indeholdende forbindelserne

Country Status (18)

Country	Link
US (1)	US4675332A (de)
EP (1)	EP0186367B1 (de)
JP (1)	JPH0653736B2 (de)
KR (1)	KR890000292B1 (de)
CN (1)	CN1005974B (de)
AT (1)	ATE86252T1 (de)
AU (1)	AU576131B2 (de)
CA (1)	CA1259317A (de)
DE (1)	DE3587148T2 (de)
DK (1)	DK174104B1 (de)
ES (1)	ES8700252A1 (de)
FI (1)	FI84719C (de)
GR (1)	GR852948B (de)
IE (1)	IE58554B1 (de)
NO (1)	NO159653C (de)
NZ (1)	NZ214480A (de)
PH (1)	PH24075A (de)
PT (1)	PT81637B (de)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE64995B1 (en) *	1987-07-14	1995-09-20	Warner Lambert Co	Novel benzothiophenes having antiallergic activity and both novel and other selected benzothiophenes having activity for treating acute respiratory distress syndrome
IT1228893B (it) *	1989-02-24	1991-07-09	Valeas Spa	Derivati tetrazol ammidici di acidi alchenil eterociclici e loroimpiego come sostanze antiallergiche
LU87611A1 (fr) *	1989-10-20	1991-05-07	Oreal	Composition tinctoriale pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs amino indoliques,procedes de teinture mettant en oeuvre ces compositions et composes nouveaux
US5051442A (en) *	1990-04-25	1991-09-24	Merrell Dow Pharmaceuticals Inc.	3-indolyl thioacetate derivatives and NMDA receptor antagonistic use thereof
US5095031A (en) *	1990-08-20	1992-03-10	Abbott Laboratories	Indole derivatives which inhibit leukotriene biosynthesis
US5189054A (en) *	1990-11-02	1993-02-23	Merrell Dow Pharmaceuticals Inc.	3-amidoindolyl derivatives and pharmaceutical compositions thereof
CA2054339C (en) *	1990-11-02	2002-12-24	Francesco G. Salituro	3-amidoindolyl derivatives
US5599774A (en) *	1992-01-22	1997-02-04	Imperial Chemical Industries Plc	N-arylindoles and their use as herbicides
US5395817A (en) *	1992-01-22	1995-03-07	Imperial Chemical Industries Plc	N-arylindoles and their use as herbicides
US5424329A (en) *	1993-08-18	1995-06-13	Warner-Lambert Company	Indole-2-carboxamides as inhibitors of cell adhesion
GB9716657D0 (en)	1997-08-07	1997-10-15	Zeneca Ltd	Chemical compounds
GB9803226D0 (en)	1998-02-17	1998-04-08	Zeneca Ltd	Chemical compounds
GB9902459D0 (en) *	1999-02-05	1999-03-24	Zeneca Ltd	Chemical compounds
GB9902461D0 (en)	1999-02-05	1999-03-24	Zeneca Ltd	Chemical compounds
GB9902455D0 (en) *	1999-02-05	1999-03-24	Zeneca Ltd	Chemical compounds
GB9902453D0 (en)	1999-02-05	1999-03-24	Zeneca Ltd	Chemical compounds
GB9902452D0 (en)	1999-02-05	1999-03-24	Zeneca Ltd	Chemical compounds
GB0000625D0 (en)	2000-01-13	2000-03-01	Zeneca Ltd	Chemical compounds
US6436965B1 (en)	2000-03-02	2002-08-20	Merck Frosst Canada & Co.	PDE IV inhibiting amides, compositions and methods of treatment
EP1314733A1 (de) *	2001-11-22	2003-05-28	Aventis Pharma Deutschland GmbH	Indol-2-carbonsäureamide als Faktor-Xa-Hemmer
GB0217920D0 (en) *	2002-04-23	2002-09-11	Aventis Pharm Prod Inc	Interleukin-4 Gene Expression inhibitors
ATE438621T1 (de) *	2002-04-23	2009-08-15	Aventis Pharma Inc	3-(substitutierte amino)-1h-indole-2- carbonsäureester und 3-(substitutierte amino)- benzoäbüthiophen-2-carbonsäureester verbindungen als inhibitoren der interleukin-4 genexpression
AU2003258145A1 (en) *	2002-08-07	2004-02-25	Idenix (Cayman) Limited	Substituted phenylindoles for the treatment of hiv
EP1479677A1 (de) *	2003-05-19	2004-11-24	Aventis Pharma Deutschland GmbH	Neue Indolderivate als Faktor Xa-Inhibitoren
EP1644360A1 (de) *	2003-06-05	2006-04-12	Warner-Lambert Company LLC	3-substituierte indole und ihre derivate als therapeutische mittel
DE602004020685D1 (de) *	2003-12-11	2009-05-28	Aventis Pharma Inc	Substituierte 1h-pyrroloä3,2-b, 3,2-c und 2,3-cüpyridin-2-carbonsäureamide und verwandte analoga als inhibitoren von caseinkinase-i-epsilon
MXPA06014535A (es)	2004-06-18	2007-06-05	Biolipox Ab	Indoles utiles en el tratamiento de la inflamacion.
BRPI0519774A2 (pt)	2005-01-19	2009-02-10	Biolipox Ab	composto ou um sal farmaceuticamente aceitÁvel do mesmo, formulaÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel do mesmo, mÉtodo de tratamento de uma doenÇa em que inibiÇço da atividade de um membro da famÍlia mapeg É desejada e/ou necessÁria, produto combinado, e, processo para a preparaÇço de um composto
PT1888548E (pt)	2005-05-26	2012-10-30	Neuron Systems Inc	Derivado de quinolina para o tratamento de doenças da retina
WO2011072141A1 (en)	2009-12-11	2011-06-16	Neuron Systems, Inc.	Compositions and methods for the treatment of macular degeneration
WO2012081893A2 (ko) *	2010-12-13	2012-06-21	한국화학연구원	신규한 3-인돌리논 유도체 및 이를 포함하는 조성물
RU2015120478A (ru)	2012-12-20	2017-01-25	Альдейра Терапьютикс, Инк.	Пери-карбинолы
CA2898631C (en)	2013-01-23	2023-06-13	Aldeyra Therapeutics, Inc.	Toxic aldehyde related diseases and treatment
SG11201505599YA (en)	2013-01-25	2015-08-28	Aldeyra Therapeutics Inc	Novel traps in the treatment of macular degeneration
CN118724806A (zh)	2015-08-21	2024-10-01	奥尔德拉医疗公司	氘化化合物和其用途
US11129823B2 (en)	2016-05-09	2021-09-28	Aldeyra Therapeutics, Inc.	Combination treatment of ocular inflammatory disorders and diseases
MX2019010576A (es)	2017-03-16	2019-10-07	Aldeyra Therapeutics Inc	Compuestos polimorficos y usos de los mismos.
JP7311162B2 (ja)	2017-10-10	2023-07-19	アルデイラセラピューティクス，インコーポレイテッド	炎症性障害の処置
US11690824B2 (en)	2018-04-10	2023-07-04	The General Hospital Corporation	Antibacterial compounds
WO2020033344A1 (en)	2018-08-06	2020-02-13	Aldeyra Therapeutics, Inc.	Polymorphic compounds and uses thereof
US12098132B2 (en)	2019-05-02	2024-09-24	Aldeyra Therapeutics, Inc.	Process for preparation of aldehyde scavenger and intermediates
CN113784954A (zh)	2019-05-02	2021-12-10	奥尔德拉医疗公司	多晶型化合物和其用途
CN112028815A (zh) *	2019-06-03	2020-12-04	中国药科大学	吲哚类衍生物及其医药用途
CA3175856A1 (en)	2020-05-13	2021-11-18	Todd Brady	Pharmaceutical formulations and uses thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3417096A (en) *	1965-07-01	1968-12-17	Bristol Myers Co	Certain 5(1-benzoyl-3-indolylmethyl) tetrazoles
US4316904A (en) *	1978-06-05	1982-02-23	Brown Richard E	Indolopyrone tetrazoles and carboxamidotetrazoles having antiallergic activity
US4432986A (en) *	1979-06-18	1984-02-21	Riker Laboratories, Inc.	Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof
US4333943A (en) *	1980-04-24	1982-06-08	Miles Laboratories, Inc.	Ethyl 3-(3-indolyl)-3-(5-tetrazolyl) propionate compounds used as anti-hypertensive agents
DE3131527A1 (de) *	1981-08-08	1983-02-24	Kali-Chemie Pharma Gmbh, 3000 Hannover	1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
GB2111050B (en) *	1981-11-19	1985-09-11	Ciba Geigy Ag	N-substituted-2-pyridylindoles
US4567201A (en) *	1981-11-25	1986-01-28	Takeda Chemical Industries, Ltd.	Diphenoxypropane derivatives and compositions of antiasthmatic and antiinflammatory agents thereof
US4436746A (en) *	1982-09-30	1984-03-13	Ciba-Geigy Corporation	Thromboxane synthetase inhibitory N-substituted-2-(1-imidazolyl)indoles
US4511573A (en) *	1983-05-17	1985-04-16	Ciba-Geigy Corporation	3-Substituted-2-(heteroaryl) indoles
US4536505A (en) *	1983-05-17	1985-08-20	Ciba-Geigy Corporation	Certain N-(pyridyl) indoles
EP0146243A1 (de) *	1983-10-31	1985-06-26	Merck Frosst Canada Inc.	Lipoxygenase-Inhibitoren
US4581354A (en) *	1984-08-06	1986-04-08	Sterling Drug Inc.	3-arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, compositions and use
IE58555B1 (en) *	1984-12-10	1993-10-06	Warner Almbert Company	Novel benzothiophenes and benzofurans having antiallergy activity

1985
- 1985-10-21 US US06/788,111 patent/US4675332A/en not_active Expired - Lifetime
- 1985-11-13 IE IE284185A patent/IE58554B1/en not_active IP Right Cessation
- 1985-11-29 AU AU50508/85A patent/AU576131B2/en not_active Ceased
- 1985-12-04 FI FI854821A patent/FI84719C/fi not_active IP Right Cessation
- 1985-12-06 PH PH33140A patent/PH24075A/en unknown
- 1985-12-09 NZ NZ214480A patent/NZ214480A/en unknown
- 1985-12-09 JP JP60275227A patent/JPH0653736B2/ja not_active Expired - Fee Related
- 1985-12-09 DK DK198505688A patent/DK174104B1/da not_active IP Right Cessation
- 1985-12-09 GR GR852948A patent/GR852948B/el unknown
- 1985-12-09 NO NO854941A patent/NO159653C/no unknown
- 1985-12-10 KR KR1019850009255A patent/KR890000292B1/ko not_active Expired
- 1985-12-10 ES ES549768A patent/ES8700252A1/es not_active Expired
- 1985-12-10 CA CA000497268A patent/CA1259317A/en not_active Expired
- 1985-12-10 DE DE8585308948T patent/DE3587148T2/de not_active Expired - Fee Related
- 1985-12-10 CN CN85109061.3A patent/CN1005974B/zh not_active Expired
- 1985-12-10 PT PT81637A patent/PT81637B/pt not_active IP Right Cessation
- 1985-12-10 EP EP85308948A patent/EP0186367B1/de not_active Expired - Lifetime
- 1985-12-10 AT AT85308948T patent/ATE86252T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU576131B2 (en)	1988-08-11
AU5050885A (en)	1986-06-19
PT81637B (pt)	1988-02-17
FI854821A7 (fi)	1986-06-11
NO854941L (no)	1986-06-11
CN1005974B (zh)	1989-12-06
ATE86252T1 (de)	1993-03-15
FI854821A0 (fi)	1985-12-04
PT81637A (en)	1986-01-01
NO159653C (no)	1989-01-25
NO159653B (no)	1988-10-17
DK568885A (da)	1986-06-11
FI84719C (fi)	1992-01-10
CA1259317A (en)	1989-09-12
DK568885D0 (da)	1985-12-09
ES8700252A1 (es)	1986-10-16
US4675332A (en)	1987-06-23
CN85109061A (zh)	1987-01-21
JPH0653736B2 (ja)	1994-07-20
FI84719B (fi)	1991-09-30
KR860004882A (ko)	1986-07-14
EP0186367A2 (de)	1986-07-02
IE58554B1 (en)	1993-10-06
NZ214480A (en)	1988-05-30
DE3587148D1 (de)	1993-04-08
EP0186367B1 (de)	1993-03-03
JPS61191683A (ja)	1986-08-26
ES549768A0 (es)	1986-04-16
GR852948B (de)	1986-04-11
DE3587148T2 (de)	1993-07-15
PH24075A (en)	1990-03-05
KR890000292B1 (ko)	1989-03-13
IE852841L (en)	1986-06-10
EP0186367A3 (en)	1988-01-07

Legal Events

Date	Code	Title	Description
2002-06-17	B1	Patent granted (law 1993)
2004-08-09	PBP	Patent lapsed	Country of ref document: DK

Publication	Publication Date	Title
DK174104B1 (da)	2002-06-17	1-Tetrazol-5-yl-1H-indol-carboxamidderivater, fremgangsmåde til fremstilling deraf samt lægemidde indeholdende forbindelserne
US5338756A (en)	1994-08-16	Benzimidazole compounds
US4818756A (en)	1989-04-04	2-pyrimidinyl-1-piperazine derivatives, processes for their preparation and medicaments containing them
US4788199A (en)	1988-11-29	Pharmacologically active amides, processes for their preparation and pharmaceutical compositions containing them
US5834463A (en)	1998-11-10	Condensed heterocyclic compounds, their production and use
NO151966B (no)	1985-04-01	Analogifremgangsmaate for fremstilling av terapeutisk virksomme imidazol-5-eddiksyrederivater
NO871879L (no)	1987-11-09	Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser.
EP0544821A1 (de)	1993-06-09	Indolderivate als antiallergische und antiinflammatorische mittel.
AU593605B2 (en)	1990-02-15	New dihydrobenzofuran- and chroman-carboxamide derivatives, processes for the preparation thereof and use thereof as neuroleptics
NO301929B1 (no)	1997-12-29	4-aryl-tiazol- eller -imidazol-derivater
FI80691C (fi)	1990-07-10	Foerfarande foer framstaellning av bensotiofener och bensofuraner med antiallergisk aktivitet.
FR2630328A1 (fr)	1989-10-27	Derive de l'histamine, sa preparation et son application en therapeutique
US4952584A (en)	1990-08-28	9H-pyrido[2,B-8]indole-3-carboxylic acid ester compounds having useful pharmaceutical activity
CS226021B2 (en)	1984-03-19	Method of presparing piperidine propylderivatives
IE61901B1 (en)	1994-11-30	"Substituted 1h-imidazoles"
US4444981A (en)	1984-04-24	10 Oxo-4,5-dihydro-10H-benzo 5,6 cycloheph[1,2-B]pyrryls
US4282360A (en)	1981-08-04	7-Methylthio or methylsulfinyl-5-oxo-5H-thiazolo[2,3-b]quinazoline-2-carboxylic acid
NO832810L (no)	1984-02-06	1,3-dioksolo(4,5-g)-kinoliner og fremgangsmaate for deres fremstilling.
EP0330340A1 (de)	1989-08-30	Therapeutische Mittel
SU1433411A3 (ru)	1988-10-23	Способ получени производных 2-(1Н)-хинолона или их фармацевтически приемлемых солей
IE52102B1 (en)	1987-06-24	Indole and indoline derivatives
EP0287971B1 (de)	1993-02-24	Benzimidazol-Derivate und Verfahren zu ihrer Herstellung
MX2007015070A (es)	2008-01-24	Compuestos novedosos de indolina.
US5112836A (en)	1992-05-12	Cyclic anthranililc acid carboxylic acid derivatives and medical therapeutic use thereof
US5475000A (en)	1995-12-12	3-(substituted tetrazolyl)-4-oxo-4H-pyrido-[1,2-a]pyrimidines, salts thereof, pharmaceutical compositions containing them and process for preparing same