IL101248A - History of indole, their preparation and the pharmaceutical preparations containing them - Google Patents

History of indole, their preparation and the pharmaceutical preparations containing them

Info

Publication number: IL101248A
Authority: IL; Israel
Prior art keywords: indolyl; methyl; urea; diisopropylphenyl; alkyl
Prior art date: 1991-03-26

Application number

IL10124892A

Other languages

English (en)

Hebrew (he)

Other versions

IL101248A0 (en

Original Assignee

Lipha

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.)

1991-03-26

Filing date

1992-03-16

Publication date

1996-12-05

1992-03-16 Application filed by Lipha filed Critical Lipha

1992-11-15 Publication of IL101248A0 publication Critical patent/IL101248A0/xx

1996-12-05 Publication of IL101248A publication Critical patent/IL101248A/en

Links

229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 8
150000002475 indoles Chemical class 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
-1 alkyl radical Chemical class 0.000 claims description 164
150000001875 compounds Chemical class 0.000 claims description 148
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 99
239000004202 carbamide Substances 0.000 claims description 66
238000000034 method Methods 0.000 claims description 28
150000003254 radicals Chemical class 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 18
150000002825 nitriles Chemical class 0.000 claims description 16
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 12
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
229910052705 radium Inorganic materials 0.000 claims description 8
229910052701 rubidium Inorganic materials 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
229940127557 pharmaceutical product Drugs 0.000 claims description 7
201000001320 Atherosclerosis Diseases 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 5
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
230000000879 anti-atherosclerotic effect Effects 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
230000000055 hyoplipidemic effect Effects 0.000 claims description 4
150000002466 imines Chemical class 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 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 claims description 2
230000003178 anti-diabetic effect Effects 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims 1
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000006622 cycloheptylmethyl group Chemical group 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 9
125000004414 alkyl thio group Chemical group 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 92
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
239000002904 solvent Substances 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
239000000203 mixture Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
238000010992 reflux Methods 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 13
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000002798 polar solvent Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
235000012000 cholesterol Nutrition 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000005259 measurement Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000005303 weighing Methods 0.000 description 4
FEUFNKALUGDEMQ-UHFFFAOYSA-N 2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=O FEUFNKALUGDEMQ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
150000001840 cholesterol esters Chemical class 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
235000005911 diet Nutrition 0.000 description 3
230000000694 effects Effects 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000031891 intestinal absorption Effects 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
UGRVYFQFDZRNMQ-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonohydrazide Chemical compound CC(C)C1=CC(C(C)C)=C(S(=O)(=O)NN)C(C(C)C)=C1 UGRVYFQFDZRNMQ-UHFFFAOYSA-N 0.000 description 2
NHICYBBDVYPMCA-UHFFFAOYSA-N 2-(1-methylindol-3-yl)hexan-1-amine Chemical compound C1=CC=C2C(C(CN)CCCC)=CN(C)C2=C1 NHICYBBDVYPMCA-UHFFFAOYSA-N 0.000 description 2
FBUSGNUOURHYCP-UHFFFAOYSA-N 2-hydroxy-2-phenylacetic acid 2-(1-methylindol-3-yl)hexan-1-amine Chemical compound C(C(O)C1=CC=CC=C1)(=O)O.CN1C=C(C2=CC=CC=C12)C(CN)CCCC FBUSGNUOURHYCP-UHFFFAOYSA-N 0.000 description 2
GATAOJICMOPURT-UHFFFAOYSA-N 2-pentan-3-yl-1-propylbenzimidazole Chemical compound C1=CC=C2N(CCC)C(C(CC)CC)=NC2=C1 GATAOJICMOPURT-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
206010015719 Exsanguination Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
102100030817 Liver carboxylesterase 1 Human genes 0.000 description 2
101710181187 Liver carboxylesterase 1 Proteins 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
JJSCUXAFAJEQGB-QMMMGPOBSA-N [(1s)-1-isocyanatoethyl]benzene Chemical compound O=C=N[C@@H](C)C1=CC=CC=C1 JJSCUXAFAJEQGB-QMMMGPOBSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000004996 alkyl benzenes Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
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125000003373 pyrazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc 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
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
XQKBFQXWZCFNFF-UHFFFAOYSA-K triiodosamarium Chemical compound I[Sm](I)I XQKBFQXWZCFNFF-UHFFFAOYSA-K 0.000 description 1
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D209/16—Tryptamines
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10124892A 1991-03-26 1992-03-16 History of indole, their preparation and the pharmaceutical preparations containing them IL101248A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9103618A FR2674522B1 (fr)	1991-03-26	1991-03-26	Nouveaux derives de l'indole, procedes de preparation et medicaments les contenant.

Publications (2)

Publication Number	Publication Date
IL101248A0 IL101248A0 (en)	1992-11-15
IL101248A true IL101248A (en)	1996-12-05

Family

ID=9411107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10124892A IL101248A (en)	1991-03-26	1992-03-16	History of indole, their preparation and the pharmaceutical preparations containing them

Country Status (25)

Country	Link
US (1)	US5219859A (cs)
EP (1)	EP0506532B1 (cs)
JP (1)	JPH0597802A (cs)
KR (1)	KR950007753B1 (cs)
AT (1)	ATE111078T1 (cs)
AU (1)	AU658609B2 (cs)
CA (1)	CA2063170A1 (cs)
CS (1)	CS89592A3 (cs)
DE (1)	DE69200378T2 (cs)
DK (1)	DK0506532T3 (cs)
ES (1)	ES2064149T3 (cs)
FR (1)	FR2674522B1 (cs)
HU (1)	HUT65489A (cs)
IE (1)	IE65366B1 (cs)
IL (1)	IL101248A (cs)
MA (1)	MA22474A1 (cs)
MX (1)	MX9201365A (cs)
NO (1)	NO178260C (cs)
NZ (1)	NZ242078A (cs)
OA (1)	OA09573A (cs)
RU (1)	RU2074179C1 (cs)
SI (1)	SI9210305A (cs)
TN (1)	TNSN92022A1 (cs)
YU (1)	YU30592A (cs)
ZA (1)	ZA922163B (cs)

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IL109568A0 (en) *	1993-05-19	1994-08-26	Fujisawa Pharmaceutical Co	Urea derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof
US5952354A (en) *	1993-07-21	1999-09-14	American Home Products Corporation	Tris carbamic acid esters: inhibitors of cholesterol absorption
DE4401893A1 (de) *	1994-01-24	1995-07-27	Bayer Ag	Substituierte Arylharnstoffe
JP3720395B2 (ja) *	1994-09-20	2005-11-24	京都薬品工業株式会社	新規ヘテロ環誘導体、その製造方法およびその医薬用途
MY114711A (en) *	1995-06-06	2002-12-31	Pfizer	Substituted n-(indole-2-carbonyl)-b-alanmamides and derivatives as antidiabetic agents
FI974437A7 (fi)	1995-06-06	1997-12-05	Pfizer	Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogee nifosforylaasi-inhibiittoreina
DE69523182T2 (de) *	1995-06-06	2002-02-07	Pfizer	Substituierte n-(indol-2-carbonyl)-glycinamide und derivate als glycogen phosphorylase inhibitoren
AU679887B2 (en) *	1995-09-11	1997-07-10	Nihon Nohyaku Co., Ltd.	Azole derivatives, their use, production and usage
DK0866059T3 (da)	1995-10-05	2002-03-25	Kyoto Pharma Ind	Nye heterocykliske derivater og medicinsk anvendelse deraf
CA2190041A1 (en) *	1995-11-13	1997-05-14	Shinya Inoue	Urea derivatives
DE122010000020I1 (de) *	1996-04-25	2010-07-08	Prosidion Ltd	Verfahren zur Senkung des Blutglukosespiegels in Säugern
FR2763334A1 (fr) *	1997-05-13	1998-11-20	Lipha	Derives anthraniliques
US6518289B1 (en) *	1997-12-16	2003-02-11	Pfizer, Inc.	1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
NZ503980A (en) *	1997-12-16	2002-09-27	Warner Lambert Co	4(3)substituted-4(3)-aminomethyl-(thio)pyran or -piperidine derivatives (= gabapentin analogues), pharmaceuticals thereof, and their use in the treatment of neurological disorders
DK1045839T3 (da) *	1997-12-16	2004-07-05	Warner Lambert Co	Hidtil ukendte aminer som farmaceutiske midler
SK282727B6 (sk)	1997-12-19	2002-11-06	Slovakofarma, A. S.	1,3-Disubstituované močoviny - inhibítory ACAT a spôsob ich prípravy
US6277877B1 (en)	2000-08-15	2001-08-21	Pfizer, Inc.	Substituted n-(indole-2-carbonyl)glycinamides and derivates as glycogen phosphorylase inhibitors
EP1349858B1 (en)	2000-11-02	2008-08-27	THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES	Agents useful for reducing amyloid precursor protein and treating demantia and methods of use thereof
CA2484582A1 (en) *	2002-05-03	2003-11-13	Warner-Lambert Company Llc	Bombesin antagonists
BR0312734A (pt) *	2002-07-17	2005-04-26	Kyoto Pharma Ind	Composto de indolina e uso medicinal do mesmo
US7595403B2 (en)	2003-04-01	2009-09-29	Eli Lilly And Company	Benzisothiazol-3-one-carboxylic acid amides as phospholipase inhibitors
KR20060111898A (ko) *	2003-08-29	2006-10-30	교와 가부시키가이샤	지질-풍부-플라크의 안정화 방법 및 파열 예방방법
EP1960355A1 (en)	2005-11-30	2008-08-27	F.Hoffmann-La Roche Ag	3-amino-1-arylpropyl indoles and aza-substituted indoles
DE602006009138D1 (de)	2005-11-30	2009-10-22	Hoffmann La Roche	3-amino-2-arylpropylazaindole und anwendungen davon
RU2361581C2 (ru) *	2007-09-14	2009-07-20	Закрытое Акционерное Общество "Мастерклон"	Фармацевтическая композиция, обладающая противодиабетической, гиполипидемической, гипогликемической и гипохолестеринемической активностью, способ ее получения и способы лечения указанных заболеваний
SK287385B6 (sk)	2007-11-27	2010-08-09	Hameln-Rds, A. S.	1,3-Disubstituované močoviny, spôsob ich prípravy a použitia
CN104628621A (zh) *	2015-01-22	2015-05-20	湖南华腾制药有限公司	一种氟取代吲哚衍生物的制备方法
EP3519816A4 (en)	2016-09-29	2020-05-06	The Regents of the University of California	CONNECTIONS FOR INCREASING NEURONAL PLASTICITY
KR102854338B1 (ko)	2017-06-26	2025-09-03	루넬라 바이오테크 인코포레이티드	미토케토신: 암 세포에서 케톤 대사를 표적화하는 미토콘드리아-기반의 치료제
KR102946120B1 (ko)	2019-02-27	2026-03-30	더 리젠츠 오브 더 유니버시티 오브 캘리포니아	뇌 장애를 치료하기 위한 아제피노-인돌 및 다른 헤테로사이클
IL313455A (en)	2021-12-15	2024-08-01	Delix Therapeutics Inc	Phenoxy and benzyloxy modified psychroplastogens and their uses

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JPS55151505A (en) *	1979-05-14	1980-11-26	Kuraray Co Ltd	Indole agricultural and horticultural fungicide
CA1299174C (en) *	1987-02-02	1992-04-21	Michael Edward Flaugh	Alkylmelatonins
EP0375133A1 (en) *	1988-11-14	1990-06-27	The Upjohn Company	Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents
IE903206A1 (en) *	1989-09-07	1991-03-13	Abbott Lab	Indole-, benzofuran-, and benzothiophene-containing¹lipoxygenase-inhibiting compounds
WO1991004027A1 (en) *	1989-09-15	1991-04-04	Pfizer Inc.	New n-aryl and n-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme a: cholesterol acyl transferase (acat)
ES2079530T3 (es) *	1990-08-13	1996-01-16	Hoechst Roussel Pharma	1-(piridinilalquil)-1h-indoles, -indolinas y compuestos analogos relacionados.
FR2680366B1 (fr) *	1991-08-13	1995-01-20	Adir	Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
WO1993005020A1 (en) *	1991-09-06	1993-03-18	Merck & Co., Inc.	Indoles as inhibitors of hiv reverse transcriptase

1991
- 1991-03-26 FR FR9103618A patent/FR2674522B1/fr not_active Expired - Fee Related
1992
- 1992-03-16 IL IL10124892A patent/IL101248A/en not_active IP Right Cessation
- 1992-03-17 CA CA002063170A patent/CA2063170A1/en not_active Abandoned
- 1992-03-20 DE DE69200378T patent/DE69200378T2/de not_active Expired - Fee Related
- 1992-03-20 AT AT92400764T patent/ATE111078T1/de active
- 1992-03-20 ES ES92400764T patent/ES2064149T3/es not_active Expired - Lifetime
- 1992-03-20 NZ NZ242078A patent/NZ242078A/en unknown
- 1992-03-20 AU AU13094/92A patent/AU658609B2/en not_active Ceased
- 1992-03-20 US US07/855,544 patent/US5219859A/en not_active Expired - Fee Related
- 1992-03-20 DK DK92400764.4T patent/DK0506532T3/da active
- 1992-03-20 EP EP92400764A patent/EP0506532B1/fr not_active Expired - Lifetime
- 1992-03-23 MA MA22763A patent/MA22474A1/fr unknown
- 1992-03-24 NO NO921141A patent/NO178260C/no unknown
- 1992-03-24 IE IE920937A patent/IE65366B1/en not_active IP Right Cessation
- 1992-03-25 CS CS92895A patent/CS89592A3/cs unknown
- 1992-03-25 ZA ZA922163A patent/ZA922163B/xx unknown
- 1992-03-25 HU HU9200997A patent/HUT65489A/hu unknown
- 1992-03-25 RU SU925011235A patent/RU2074179C1/ru active
- 1992-03-25 JP JP4067252A patent/JPH0597802A/ja active Pending
- 1992-03-26 KR KR1019920005020A patent/KR950007753B1/ko not_active Expired - Fee Related
- 1992-03-26 OA OA60177A patent/OA09573A/fr unknown
- 1992-03-26 YU YU30592A patent/YU30592A/sh unknown
- 1992-03-26 MX MX9201365A patent/MX9201365A/es not_active IP Right Cessation
- 1992-03-26 SI SI9210305A patent/SI9210305A/sl unknown
- 1992-03-26 TN TNTNSN92022A patent/TNSN92022A1/fr unknown

Also Published As

Publication number	Publication date
US5219859A (en)	1993-06-15
CS89592A3 (en)	1992-10-14
NO921141D0 (no)	1992-03-24
DE69200378D1 (de)	1994-10-13
MX9201365A (es)	1992-10-01
EP0506532B1 (fr)	1994-09-07
KR920018022A (ko)	1992-10-21
DK0506532T3 (da)	1995-02-20
ZA922163B (en)	1993-09-27
IL101248A0 (en)	1992-11-15
IE65366B1 (en)	1995-10-18
MA22474A1 (fr)	1992-10-01
SI9210305A (en)	1996-02-29
RU2074179C1 (ru)	1997-02-27
FR2674522A1 (fr)	1992-10-02
IE920937A1 (en)	1992-10-07
CA2063170A1 (en)	1992-09-27
OA09573A (fr)	1993-01-31
AU658609B2 (en)	1995-04-27
NO178260B (no)	1995-11-13
EP0506532A1 (fr)	1992-09-30
FR2674522B1 (fr)	1993-07-16
NO178260C (no)	1996-02-21
ATE111078T1 (de)	1994-09-15
HUT65489A (en)	1994-06-28
JPH0597802A (ja)	1993-04-20
ES2064149T3 (es)	1995-01-16
NO921141L (no)	1992-09-28
TNSN92022A1 (fr)	1993-06-08
YU30592A (sh)	1994-12-28
KR950007753B1 (ko)	1995-07-14
NZ242078A (en)	1994-10-26
HU9200997D0 (en)	1992-05-28
AU1309492A (en)	1992-10-01
DE69200378T2 (de)	1995-03-09

Legal Events

Date	Code	Title	Description
1997-06-10	FF	Patent granted
1999-03-12	RH	Patent void

Publication	Publication Date	Title
IL101248A (en)	1996-12-05	History of indole, their preparation and the pharmaceutical preparations containing them
US5338849A (en)	1994-08-16	Azaindoles, preparation processes and medicinal products containing them
KR100359393B1 (ko)	2003-01-24	5-ht1a 길항제로서의 피페라진유도체 및 이의 제조방법
CN1997649B (zh)	2010-08-11	组蛋白脱乙酰基酶的抑制剂
CA2559733C (en)	2014-05-13	Inhibitors of histone deacetylase
KR101441146B1 (ko)	2014-09-17	Ｎｐｙｙ5 수용체 길항 작용을 갖는 아민 유도체
NZ230493A (en)	1991-03-26	N-substituted nicotinamide derivatives and pharmaceutical compositions
DK162629B (da)	1991-11-25	2-substituerede 1-aralkyl-imidazoler og farmaceutiske midler der indeholder disse, anvendelse heraf til fremstilling af farmaceutiske midler samt fremgangsmaade til fremstilling heraf
EP1567528A1 (en)	2005-08-31	Mixed lineage kinase modulators
AU2006239545A1 (en)	2006-11-02	Phenylacetylene derivatives having MGLUR5 receptor affinity
IE57057B1 (en)	1992-04-08	Carboxamides,process for their preparation and pharmaceutical preparations containing them
JP2008545686A (ja)	2008-12-18	５ｈｔ６受容体を調節する新規な８−スルホニルアミノ−３アミノ置換クロマンまたはテトラヒドロナフタレン誘導体
JP2006508090A (ja)	2006-03-09	新規β−アゴニスト、それらの製造方法及び医薬組成物としてのそれらの使用
JP4503549B2 (ja)	2010-07-14	インダニル−ピペラジン化合物、その製造方法及びこれらを含む医薬組成物
NZ286340A (en)	1997-06-24	Amides of 2-(4-indolyl piperazia-1-yl)-1-ph-enyl (and bemzyl)ethyl amine derivatives with various (cyclo) alkane carboxylic acids; pharmaceutical compositions
KR100248643B1 (ko)	2000-07-01	아릴 및 헤테로아릴 알콕시나프탈렌 유도체
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