SK17899A3 - Palladium catalyzed indolization - Google Patents

Palladium catalyzed indolization Download PDF

Info

Publication number: SK17899A3
Authority: SK; Slovakia
Prior art keywords: indol; triazol; propyl; ethyl; alkyl
Prior art date: 1996-08-13

Application number

SK178-99A

Other languages

English (en)

Slovak (sk)

Inventor

Cheng-Yi Chen

Robert D Larsen

Original Assignee

Merck & Co Inc

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.)

1996-08-13

Filing date

1997-08-08

Publication date

2000-02-14

1996-09-12 Priority claimed from GBGB9619064.0A external-priority patent/GB9619064D0/en

1997-08-08 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

2000-02-14 Publication of SK17899A3 publication Critical patent/SK17899A3/sk

Links

KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 76
229910052763 palladium Inorganic materials 0.000 title claims description 36
238000006919 indolization reaction Methods 0.000 title description 2
-1 acyl silane derivative Chemical class 0.000 claims abstract description 300
238000000034 method Methods 0.000 claims abstract description 58
125000001424 substituent group Chemical group 0.000 claims abstract description 37
230000008569 process Effects 0.000 claims abstract description 32
150000002475 indoles Chemical class 0.000 claims abstract description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
125000001425 triazolyl group Chemical group 0.000 claims abstract description 10
239000000543 intermediate Substances 0.000 claims abstract description 7
150000003852 triazoles Chemical class 0.000 claims abstract description 7
238000010511 deprotection reaction Methods 0.000 claims abstract description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 172
125000000217 alkyl group Chemical group 0.000 claims description 108
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 96
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 80
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 68
229910052757 nitrogen Inorganic materials 0.000 claims description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 29
125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 22
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 14
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 14
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
235000019441 ethanol Nutrition 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
238000005903 acid hydrolysis reaction Methods 0.000 claims description 8
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
150000003973 alkyl amines Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
VLUYUKJHWACEEG-UHFFFAOYSA-N [1-[2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethyl]pyrrolidin-2-yl]methanamine Chemical compound NCC1N(CCC1)CCC1=CNC2=CC=C(C=C12)N1C=NN=C1 VLUYUKJHWACEEG-UHFFFAOYSA-N 0.000 claims description 6
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
150000003536 tetrazoles Chemical class 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 6
IMEDVUXFLMWCMH-UHFFFAOYSA-N 5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1N1C=NN=C1 IMEDVUXFLMWCMH-UHFFFAOYSA-N 0.000 claims description 5
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
150000001539 azetidines Chemical class 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000004970 halomethyl group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 5
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
229930192474 thiophene Natural products 0.000 claims description 5
125000003944 tolyl group Chemical group 0.000 claims description 5
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
HQTKJKBMUWZMCC-HXUWFJFHSA-N 3-[2-[(3r)-3-(phenylmethoxymethyl)pyrrolidin-1-yl]ethyl]-5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C([C@H](COCC=1C=CC=CC=1)CC1)N1CCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 HQTKJKBMUWZMCC-HXUWFJFHSA-N 0.000 claims description 4
PPQXZSWFDQGWBH-UHFFFAOYSA-N 3-[3-(4-benzylpiperazin-1-yl)propyl]-5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C=1NC2=CC=C(N3C=NN=C3)C=C2C=1CCCN(CC1)CCN1CC1=CC=CC=C1 PPQXZSWFDQGWBH-UHFFFAOYSA-N 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 claims description 4
NLGOBWHIRBZNDY-UHFFFAOYSA-N 5-(1,2,4-triazol-1-ylmethyl)-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1CN1C=NC=N1 NLGOBWHIRBZNDY-UHFFFAOYSA-N 0.000 claims description 4
AESIUFPLRZOCKJ-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)C1CC(N(CC1)CCCC1=CNC2=CC=C(C=C12)N1C=NN=C1)NC Chemical compound C(C)(=O)NC1=CC=C(C=C1)C1CC(N(CC1)CCCC1=CNC2=CC=C(C=C12)N1C=NN=C1)NC AESIUFPLRZOCKJ-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
229940054051 antipsychotic indole derivative Drugs 0.000 claims description 4
150000004982 aromatic amines Chemical class 0.000 claims description 4
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
IGNXHSPBUUSUHB-UHFFFAOYSA-N n,n-dimethyl-2-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1N1C=NN=C1 IGNXHSPBUUSUHB-UHFFFAOYSA-N 0.000 claims description 4
JCFDYNJSFCXYRT-FQEVSTJZSA-N n-benzyl-1-[(3s)-1-[2-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]ethyl]pyrrolidin-3-yl]methanamine Chemical compound C([C@H](CNCC=1C=CC=CC=1)CC1)N1CCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 JCFDYNJSFCXYRT-FQEVSTJZSA-N 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 claims description 3
ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 claims description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
ZUNWDTDMTVKOTH-UHFFFAOYSA-N NCC1N(CCCC1)CCCC1=CNC2=CC=C(C=C12)N1C=NN=C1 Chemical compound NCC1N(CCCC1)CCCC1=CNC2=CC=C(C=C12)N1C=NN=C1 ZUNWDTDMTVKOTH-UHFFFAOYSA-N 0.000 claims description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
ULFRLSNUDGIQQP-UHFFFAOYSA-N rizatriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CN1C=NC=N1 ULFRLSNUDGIQQP-UHFFFAOYSA-N 0.000 claims description 3
HNKDAQNYMJNLCC-SANMLTNESA-N (2r)-2-(4-fluorophenyl)-2-[[1-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperidin-4-yl]amino]ethanol Chemical compound N([C@@H](CO)C=1C=CC(F)=CC=1)C(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 HNKDAQNYMJNLCC-SANMLTNESA-N 0.000 claims description 2
ZLFLXBCKFALASU-MHZLTWQESA-N (2r)-2-[[1-[3-(5-imidazol-1-yl-1h-indol-3-yl)propyl]piperidin-4-yl]amino]-2-phenylethanol Chemical compound N([C@@H](CO)C=1C=CC=CC=1)C(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=CN=C1 ZLFLXBCKFALASU-MHZLTWQESA-N 0.000 claims description 2
JCDNSQAJVDJBNH-MHZLTWQESA-N (2r)-2-phenyl-2-[[1-[3-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]propyl]piperidin-4-yl]amino]ethanol Chemical compound N([C@@H](CO)C=1C=CC=CC=1)C(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2CN1C=NC=N1 JCDNSQAJVDJBNH-MHZLTWQESA-N 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
LQALOSZXCJFXAO-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)ethyl]-4-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperazin-2-one Chemical compound FC1=CC=CC(CCN2C(CN(CCCC=3C4=CC(=CC=C4NC=3)N3C=NN=C3)CC2)=O)=C1 LQALOSZXCJFXAO-UHFFFAOYSA-N 0.000 claims description 2
MIEAXBUEPZRDHB-OAQYLSRUSA-N 1-[3-(5-imidazol-1-yl-1h-indol-3-yl)propyl]-n-[(1r)-1-phenylethyl]piperidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=CN=C1 MIEAXBUEPZRDHB-OAQYLSRUSA-N 0.000 claims description 2
MFHUVBVZMQDBAM-UHFFFAOYSA-N 1-benzyl-4-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperazin-2-one Chemical compound C1CN(CC=2C=CC=CC=2)C(=O)CN1CCCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 MFHUVBVZMQDBAM-UHFFFAOYSA-N 0.000 claims description 2
KFOPVLRSDNVWJO-UHFFFAOYSA-N 2-(benzylamino)-2-[1-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperidin-4-yl]ethanol Chemical compound C1CN(CCCC=2C3=CC(=CC=C3NC=2)N2C=NN=C2)CCC1C(CO)NCC1=CC=CC=C1 KFOPVLRSDNVWJO-UHFFFAOYSA-N 0.000 claims description 2
WXWBRTKSGCYLQS-UHFFFAOYSA-N 2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethanol Chemical compound C1=C2C(CCO)=CNC2=CC=C1CN1C=NC=N1 WXWBRTKSGCYLQS-UHFFFAOYSA-N 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
OTAVQVGDKQYPNZ-UHFFFAOYSA-N 2-phenyl-2-[[1-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperidin-4-yl]amino]ethanol Chemical compound C=1C=CC=CC=1C(CO)NC(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 OTAVQVGDKQYPNZ-UHFFFAOYSA-N 0.000 claims description 2
UXAIXCQWNCBANT-UHFFFAOYSA-N 2-phenyl-3-[4-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperazin-1-yl]propan-1-ol Chemical compound C=1C=CC=CC=1C(CO)CN(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 UXAIXCQWNCBANT-UHFFFAOYSA-N 0.000 claims description 2
VXEWHMQYWRWFDO-UHFFFAOYSA-N 3-(1-methylpiperidin-4-yl)-5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(N3C=NN=C3)C=C12 VXEWHMQYWRWFDO-UHFFFAOYSA-N 0.000 claims description 2
SGNYSBAWYXBXPR-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)-5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C1N(C)CCC1C1=CNC2=CC=C(N3C=NN=C3)C=C12 SGNYSBAWYXBXPR-UHFFFAOYSA-N 0.000 claims description 2
XWVLIZDDCHSLMT-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-[4-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCC=2C3=CC(=CC=C3NC=2)N2C=NN=C2)CCN1C(CO)CC1=CC=C(F)C=C1 XWVLIZDDCHSLMT-UHFFFAOYSA-N 0.000 claims description 2
NYNSVPFVHILFCW-UHFFFAOYSA-N 3-[(5-benzyl-1-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-2-yl)methyl]-5-imidazol-1-yl-1h-indole Chemical compound C1C2CN(CC=3C=CC=CC=3)CC2N(C)C1CC(C1=C2)=CNC1=CC=C2N1C=CN=C1 NYNSVPFVHILFCW-UHFFFAOYSA-N 0.000 claims description 2
LWOPCDREUMDJFO-UHFFFAOYSA-N 3-[(benzylamino)methyl]-1-[2-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]ethyl]pyrrolidin-3-ol Chemical compound C1CN(CCC=2C3=CC(=CC=C3NC=2)N2C=NN=C2)CC1(O)CNCC1=CC=CC=C1 LWOPCDREUMDJFO-UHFFFAOYSA-N 0.000 claims description 2
UZALKEQSASVSHS-CILPGNKCSA-N 3-[2-[(3R)-2-methoxy-3-(4-methoxyphenyl)pyrrolidin-1-yl]ethyl]-5-(1,2,4-triazol-4-yl)-1H-indole Chemical compound C([C@@H](C1OC)C=2C=CC(OC)=CC=2)CN1CCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 UZALKEQSASVSHS-CILPGNKCSA-N 0.000 claims description 2
WNZDBSDKJREJQN-VCUSLETLSA-N 3-[2-[(3R)-3-benzylsulfanyl-2-methylpyrrolidin-1-yl]ethyl]-5-(1,2,4-triazol-4-yl)-1H-indole Chemical compound C([C@H](C1C)SCC=2C=CC=CC=2)CN1CCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 WNZDBSDKJREJQN-VCUSLETLSA-N 0.000 claims description 2
ZIFAINJUDMIJOM-OAQYLSRUSA-N 3-[2-[(3r)-3-phenylmethoxypyrrolidin-1-yl]ethyl]-5-(1,2,4-triazol-4-yl)-1h-indole Chemical compound C([C@@H](CC1)OCC=2C=CC=CC=2)N1CCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 ZIFAINJUDMIJOM-OAQYLSRUSA-N 0.000 claims description 2
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125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
238000006200 ethylation reaction Methods 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000004795 grignard reagents Chemical class 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
150000002429 hydrazines Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000035800 maturation Effects 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
229940101209 mercuric oxide Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229910000474 mercury oxide Inorganic materials 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
CPRAXXVMEPXICI-UHFFFAOYSA-N n,n-diethyl-2-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN(CC)CC)=CNC2=CC=C1N1C=NN=C1 CPRAXXVMEPXICI-UHFFFAOYSA-N 0.000 description 1
MRSOGRAQIFJIDV-UHFFFAOYSA-N n,n-diethyl-2-[5-(1,2,4-triazol-4-ylmethyl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN(CC)CC)=CNC2=CC=C1CN1C=NN=C1 MRSOGRAQIFJIDV-UHFFFAOYSA-N 0.000 description 1
ORVWUZVNKPDYHT-MHZLTWQESA-N n-[(1r)-2-methoxy-1-phenylethyl]-1-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperidin-4-amine Chemical compound N([C@@H](COC)C=1C=CC=CC=1)C(CC1)CCN1CCCC(C1=C2)=CNC1=CC=C2N1C=NN=C1 ORVWUZVNKPDYHT-MHZLTWQESA-N 0.000 description 1
FXQIFPJUNZCNRZ-UHFFFAOYSA-N n-[3-[2-[4-[3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]piperazin-1-yl]ethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CCN2CCN(CCCC=3C4=CC(=CC=C4NC=3)N3C=NN=C3)CC2)=C1 FXQIFPJUNZCNRZ-UHFFFAOYSA-N 0.000 description 1
ZHPQQZJJWUOHFA-UHFFFAOYSA-N n-benzyl-1-[2-fluoro-3-[5-(1,2,4-triazol-4-yl)-1h-indol-3-yl]propyl]-n-methylpiperidin-4-amine Chemical compound C1CN(CC(F)CC=2C3=CC(=CC=C3NC=2)N2C=NN=C2)CCC1N(C)CC1=CC=CC=C1 ZHPQQZJJWUOHFA-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 description 1
ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical class P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
238000005192 partition Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
125000006513 pyridinyl methyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000017103 tryptophane Nutrition 0.000 description 1
150000003654 tryptophanes Chemical class 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

SK178-99A 1996-08-13 1997-08-08 Palladium catalyzed indolization SK17899A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US2386096P	1996-08-13	1996-08-13
GBGB9619064.0A GB9619064D0 (en)	1996-09-12	1996-09-12	Palladium catalyzed indolization
US3015596P	1996-10-31	1996-10-31
PCT/US1997/013799 WO1998006725A1 (en)	1996-08-13	1997-08-08	Palladium catalyzed indolization

Publications (1)

Publication Number	Publication Date
SK17899A3 true SK17899A3 (en)	2000-02-14

Family

ID=27268468

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK178-99A SK17899A3 (en)	1996-08-13	1997-08-08	Palladium catalyzed indolization

Country Status (13)

Country	Link
EP (1)	EP0925302B1 (cs)
CN (1)	CN1084751C (cs)
AR (1)	AR013833A1 (cs)
AT (1)	ATE228137T1 (cs)
AU (1)	AU4053497A (cs)
BR (1)	BR9711131A (cs)
CZ (1)	CZ48299A3 (cs)
DE (1)	DE69717287T2 (cs)
EA (1)	EA003244B1 (cs)
ES (1)	ES2185983T3 (cs)
SK (1)	SK17899A3 (cs)
TW (1)	TW429259B (cs)
WO (1)	WO1998006725A1 (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9523065D0 (en) *	1995-11-10	1996-01-10	Merck Sharp & Dohme	Therapeutic agents
GB9615658D0 (en) *	1996-07-25	1996-09-04	Merck Sharp & Dohme	Therapeutic agents
US6235936B1 (en)	1998-02-26	2001-05-22	Massachusetts Institute Of Technology	Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates
SE0100326D0 (sv)	2001-02-02	2001-02-02	Astrazeneca Ab	New compounds
ES2204303B2 (es) *	2002-08-07	2004-12-16	Laboratorios Vita, S.A.	Procedimiento para la obtencion de un compuesto farmaceuticamente activo.
ATE382623T1 (de)	2004-06-09	2008-01-15	Hoffmann La Roche	Octahydropyrrolo(3,4-c)pyrrolderivate und deren verwendung als antivirale mitteln
US7665658B2 (en)	2005-06-07	2010-02-23	First Data Corporation	Dynamic aggregation of payment transactions
DE102008030207A1 (de)	2008-06-25	2009-12-31	Bayer Schering Pharma Aktiengesellschaft	Substituierte 7-Sulfanylmethyl-, 7-Sulfinylmethyl- und 7-Sulfonylmethyl-Indole und ihre Verwendung
DE102008030206A1 (de)	2008-06-25	2009-12-31	Bayer Schering Pharma Aktiengesellschaft	3-Cyanoalky- und 3-Hydroxyalkyl-Indole und ihre Verwendung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5567824A (en) *	1994-05-24	1996-10-22	Merck & Co., Inc.	Palladium catalyzed ring closure of triazolyltryptamine

1997
- 1997-08-08 CZ CZ99482A patent/CZ48299A3/cs unknown
- 1997-08-08 BR BR9711131A patent/BR9711131A/pt not_active IP Right Cessation
- 1997-08-08 DE DE69717287T patent/DE69717287T2/de not_active Expired - Fee Related
- 1997-08-08 CN CN97197284A patent/CN1084751C/zh not_active Expired - Fee Related
- 1997-08-08 WO PCT/US1997/013799 patent/WO1998006725A1/en not_active Ceased
- 1997-08-08 EA EA199900202A patent/EA003244B1/ru not_active IP Right Cessation
- 1997-08-08 AT AT97938139T patent/ATE228137T1/de not_active IP Right Cessation
- 1997-08-08 AU AU40534/97A patent/AU4053497A/en not_active Abandoned
- 1997-08-08 EP EP97938139A patent/EP0925302B1/en not_active Expired - Lifetime
- 1997-08-08 SK SK178-99A patent/SK17899A3/sk unknown
- 1997-08-08 ES ES97938139T patent/ES2185983T3/es not_active Expired - Lifetime
- 1997-08-11 TW TW086111480A patent/TW429259B/zh active
- 1997-08-12 AR ARP970103669A patent/AR013833A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1084751C (zh)	2002-05-15
CZ48299A3 (cs)	1999-07-14
EA199900202A1 (ru)	1999-08-26
WO1998006725A1 (en)	1998-02-19
AU4053497A (en)	1998-03-06
EP0925302A1 (en)	1999-06-30
TW429259B (en)	2001-04-11
DE69717287T2 (de)	2003-09-11
EP0925302B1 (en)	2002-11-20
CN1228094A (zh)	1999-09-08
AR013833A1 (es)	2001-01-31
EA003244B1 (ru)	2003-02-27
DE69717287D1 (de)	2003-01-02
BR9711131A (pt)	1999-08-17
ATE228137T1 (de)	2002-12-15
ES2185983T3 (es)	2003-05-01

Publication	Publication Date	Title
JP3309982B2 (ja)	2002-07-29	イミダゾール，トリアゾールおよびテトラゾール誘導体
AU672802B2 (en)	1996-10-17	Imidazole, triazole and tetrazole derivatives
KR100212111B1 (ko)	1999-08-02	이미다졸, 트리아졸 및 테트라졸 유도체, 및 이를 포함하는 약제학적 조성물
ES2233557T3 (es)	2005-06-16	Derivados de 2-quinolona que inhiben la farnesil transferasa.
TWI452035B (zh)	2014-09-11	以５員雜環為主之ｐ３８激酶抑制劑
HRP960576A2 (en)	1998-02-28	Farnesyl protein transferase inhibiting (imidazol-5-yl) methyl-2-quinolinone derivatives
JP2001064263A (ja)	2001-03-13	トリアゾール及びイミダゾール誘導体
WO2000075131A1 (en)	2000-12-14	Substituted pyrazole compounds
JPH10501212A (ja)	1998-02-03	５−ｈｔ▲下１ｄ▼−アルファ作働薬としてのインドール−３−イルアルキルのピペラジン、ピペリジンおよびテトラヒドロピリジン誘導体
UA80184C2 (en)	2007-08-27	Heterocyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands
HK109695A (en)	1995-07-14	1-indolylalkyl-4-(alkoxy-pyrimidinyl)piperazines
ES2202453T3 (es)	2004-04-01	Agentes antifungicos de triazol.
US5808064A (en)	1998-09-15	Palladium catalyzed indolization
AU712257B2 (en)	1999-11-04	Piperidine and tetrahydropyridine derivatives
JP2599557B2 (ja)	1997-04-09	４−置換１，２，４−トリアゾール誘導体
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