HRP930752A2 - Indole derivatives - Google Patents

Indole derivatives Download PDF

Info

Publication number: HRP930752A2
Authority: HR; Croatia
Prior art keywords: compound; alkyl; aryl; hydrogen; formula
Prior art date: 1992-04-07

Application number

HR930752A

Other languages

English (en)

Croatian (hr)

Inventor

John E Macor

Martin James Wythes

Original Assignee

Pfizer

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.)

1992-04-07

Filing date

1993-04-02

Publication date

1994-10-31

1993-04-02 Application filed by Pfizer filed Critical Pfizer

1994-10-31 Publication of HRP930752A2 publication Critical patent/HRP930752A2/hr

Links

229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
150000002475 indoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 158
229910052739 hydrogen Inorganic materials 0.000 claims description 63
239000001257 hydrogen Substances 0.000 claims description 62
125000003118 aryl group Chemical group 0.000 claims description 61
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 46
229910052799 carbon Inorganic materials 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
238000011282 treatment Methods 0.000 claims description 31
238000000034 method Methods 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
-1 C 1 to C 3 alkylaryl Chemical group 0.000 claims description 18
206010019233 Headaches Diseases 0.000 claims description 17
208000019695 Migraine disease Diseases 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
231100000869 headache Toxicity 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
206010027599 migraine Diseases 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000002877 alkyl aryl group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
125000005518 carboxamido group Chemical group 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000004615 ingredient Substances 0.000 claims description 8
208000019553 vascular disease Diseases 0.000 claims description 8
208000019901 Anxiety disease Diseases 0.000 claims description 7
206010009094 Chronic paroxysmal hemicrania Diseases 0.000 claims description 7
208000030814 Eating disease Diseases 0.000 claims description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
208000008589 Obesity Diseases 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
230000036506 anxiety Effects 0.000 claims description 7
235000014632 disordered eating Nutrition 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
208000007777 paroxysmal Hemicrania Diseases 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
208000002193 Pain Diseases 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004404 heteroalkyl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
208000011117 substance-related disease Diseases 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
206010020772 Hypertension Diseases 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
230000002950 deficient Effects 0.000 claims description 5
230000000862 serotonergic effect Effects 0.000 claims description 5
230000005062 synaptic transmission Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
206010013663 drug dependence Diseases 0.000 claims description 4
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 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000002904 solvent Substances 0.000 description 29
239000000243 solution Substances 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
239000002585 base Substances 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004440 column chromatography Methods 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000011630 iodine Substances 0.000 description 5
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
125000003386 piperidinyl group Chemical group 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QDEZFSSAEVJNDS-UHFFFAOYSA-N 3-(pyrrolidin-2-ylmethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC1CCCN1 QDEZFSSAEVJNDS-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
229910052721 tungsten Inorganic materials 0.000 description 4
SAPQIENQEZURNZ-UHFFFAOYSA-N 2,2,2-trifluoro-n-phenylacetamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC=C1 SAPQIENQEZURNZ-UHFFFAOYSA-N 0.000 description 3
102000035038 5-HT1 receptors Human genes 0.000 description 3
108091005478 5-HT1 receptors Proteins 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
238000007341 Heck reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
XRVPHGWCSXRKAY-CQSZACIVSA-N benzyl (2r)-2-(3-hydroxyprop-1-enyl)pyrrolidine-1-carboxylate Chemical compound OCC=C[C@H]1CCCN1C(=O)OCC1=CC=CC=C1 XRVPHGWCSXRKAY-CQSZACIVSA-N 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
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 description 2
QDEZFSSAEVJNDS-LLVKDONJSA-N 3-[[(2r)-pyrrolidin-2-yl]methyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1C[C@H]1CCCN1 QDEZFSSAEVJNDS-LLVKDONJSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
206010013654 Drug abuse Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
239000012448 Lithium borohydride Substances 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000556 agonist Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000005604 azodicarboxylate group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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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
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
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- 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
- C07D403/14—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 three or more hetero rings
- 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
- C07D413/10—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 aromatic rings
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Hematology (AREA)
Diabetes (AREA)
Child & Adolescent Psychology (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

HR930752A 1992-04-07 1993-04-02 Indole derivatives HRP930752A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US86473792A	1992-04-07	1992-04-07

Publications (1)

Publication Number	Publication Date
HRP930752A2 true HRP930752A2 (en)	1994-10-31

Family

ID=25343950

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR930752A HRP930752A2 (en)	1992-04-07	1993-04-02	Indole derivatives

Country Status (26)

Country	Link
US (7)	US5747501A (zh)
EP (1)	EP0635017A1 (zh)
JP (1)	JP2644088B2 (zh)
KR (1)	KR0179072B1 (zh)
CN (2)	CN1050841C (zh)
AU (1)	AU670579B2 (zh)
BR (1)	BR9306201A (zh)
CA (1)	CA2133413C (zh)
CZ (1)	CZ281763B6 (zh)
EG (1)	EG20226A (zh)
FI (1)	FI931558A (zh)
HR (1)	HRP930752A2 (zh)
HU (1)	HUT64062A (zh)
IL (1)	IL105206A (zh)
MX (1)	MX9302011A (zh)
MY (1)	MY108909A (zh)
NO (1)	NO303388B1 (zh)
NZ (1)	NZ251086A (zh)
PL (1)	PL172405B1 (zh)
RU (1)	RU2101283C1 (zh)
SK (1)	SK280193B6 (zh)
TW (1)	TW341565B (zh)
UA (1)	UA27467C2 (zh)
WO (1)	WO1993020073A1 (zh)
YU (1)	YU48931B (zh)
ZA (1)	ZA932440B (zh)

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GB9415575D0 (en) *	1994-08-02	1994-09-21	Merck Sharp & Dohme	Therapeutic agents
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CN1064682C (zh) *	1995-07-31	2001-04-18	盐野义制药株式会社	具有磷脂酶a2抑制活性的吡咯烷衍生物
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JP2002519321A (ja) *	1998-06-30	2002-07-02	イーライ・リリー・アンド・カンパニー	セロトニン関連系に効果を有するピロリジン、及び、ピロリン誘導体
WO2000008018A1 (fr) *	1998-08-07	2000-02-17	Takeda Chemical Industries, Ltd.	Derives de benzothiepine, leur procede de preparation et leurs utilisations
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US6326388B1 (en) *	1999-12-21	2001-12-04	Celgene Corporation	Substituted 1,3,4-oxadiazoles and a method of reducing TNF-alpha level
US7041697B2 (en) *	2002-09-12	2006-05-09	Wyeth	Antidepressant cycloalkylamine derivatives of 2,3-dihydro-1,4-benzodioxan
US7781426B2 (en) *	2005-12-30	2010-08-24	Merck Sharp & Dohme Corp.	CETP inhibitors
JP5656848B2 (ja) *	2008-10-16	2015-01-21	ジャンセンファーマシューティカルズ，インコーポレイテッド．	代謝型グルタミン酸受容体モジュレーターとしてのインドールおよびベンゾモルホリンの誘導体
US20100217013A1 (en) *	2008-12-15	2010-08-26	Wenge Li	Enantioselective process for the preparation of zolmitriptan
CA2891122C (en)	2012-11-14	2021-07-20	The Johns Hopkins University	Methods and compositions for treating schizophrenia
EP3447051B1 (en)	2016-04-28	2021-12-15	Jiangsu Hengrui Medicine Co., Ltd.	Method for preparing tyrosine kinase inhibitor and derivative thereof
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1993
- 1993-03-10 CZ CZ942464A patent/CZ281763B6/cs not_active IP Right Cessation
- 1993-03-10 KR KR1019940703552A patent/KR0179072B1/ko not_active IP Right Cessation
- 1993-03-10 US US08/295,798 patent/US5747501A/en not_active Expired - Fee Related
- 1993-03-10 AU AU37898/93A patent/AU670579B2/en not_active Ceased
- 1993-03-10 WO PCT/US1993/001967 patent/WO1993020073A1/en not_active Application Discontinuation
- 1993-03-10 JP JP5517443A patent/JP2644088B2/ja not_active Expired - Fee Related
- 1993-03-10 RU RU94045897/04A patent/RU2101283C1/ru not_active IP Right Cessation
- 1993-03-10 CA CA002133413A patent/CA2133413C/en not_active Expired - Fee Related
- 1993-03-10 NZ NZ251086A patent/NZ251086A/en unknown
- 1993-03-10 BR BR9306201A patent/BR9306201A/pt not_active Application Discontinuation
- 1993-03-10 EP EP93907216A patent/EP0635017A1/en not_active Ceased
- 1993-03-10 PL PL93305555A patent/PL172405B1/pl not_active IP Right Cessation
- 1993-03-10 UA UA94105899A patent/UA27467C2/uk unknown
- 1993-03-10 SK SK1206-94A patent/SK280193B6/sk unknown
- 1993-03-29 IL IL10520693A patent/IL105206A/en not_active IP Right Cessation
- 1993-04-02 HR HR930752A patent/HRP930752A2/hr not_active Application Discontinuation
- 1993-04-05 MY MYPI93000616A patent/MY108909A/en unknown
- 1993-04-05 ZA ZA932440A patent/ZA932440B/xx unknown
- 1993-04-05 EG EG20593A patent/EG20226A/xx active
- 1993-04-06 MX MX9302011A patent/MX9302011A/es unknown
- 1993-04-06 YU YU23893A patent/YU48931B/sh unknown
- 1993-04-06 CN CN93105697A patent/CN1050841C/zh not_active Expired - Fee Related
- 1993-04-06 FI FI931558A patent/FI931558A/fi not_active IP Right Cessation
- 1993-04-06 HU HU9301003A patent/HUT64062A/hu unknown
- 1993-04-09 TW TW082102651A patent/TW341565B/zh active
1994
- 1994-10-06 NO NO943762A patent/NO303388B1/no not_active IP Right Cessation
1998
- 1998-04-14 US US09/059,799 patent/US6150388A/en not_active Expired - Fee Related
- 1998-07-08 CN CN98116024A patent/CN1083443C/zh not_active Expired - Fee Related
2000
- 2000-10-23 US US09/694,809 patent/US6387941B1/en not_active Expired - Fee Related
- 2000-10-23 US US09/694,588 patent/US6465500B1/en not_active Expired - Fee Related
- 2000-10-23 US US09/694,808 patent/US6410739B1/en not_active Expired - Fee Related
- 2000-10-23 US US09/694,387 patent/US6436957B1/en not_active Expired - Fee Related
- 2000-10-23 US US09/694,394 patent/US6387937B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EG20226A (en)	1997-12-31
HU9301003D0 (en)	1993-06-28
US5747501A (en)	1998-05-05
AU3789893A (en)	1993-11-08
CN1082543A (zh)	1994-02-23
SK280193B6 (sk)	1999-09-10
RU2101283C1 (ru)	1998-01-10
ZA932440B (en)	1994-10-05
MY108909A (en)	1996-11-30
CN1050841C (zh)	2000-03-29
IL105206A (en)	1999-04-11
TW341565B (en)	1998-10-01
YU48931B (sh)	2002-12-10
US6465500B1 (en)	2002-10-15
MX9302011A (es)	1994-03-31
JP2644088B2 (ja)	1997-08-25
WO1993020073A1 (en)	1993-10-14
UA27467C2 (uk)	2000-09-15
CZ281763B6 (cs)	1997-01-15
CA2133413C (en)	2001-04-10
FI931558A (fi)	1993-10-08
SK120694A3 (en)	1995-05-10
CN1083443C (zh)	2002-04-24
CA2133413A1 (en)	1993-10-14
JPH07504919A (ja)	1995-06-01
US6387937B1 (en)	2002-05-14
NO943762L (no)	1994-10-06
CN1225362A (zh)	1999-08-11
NZ251086A (en)	1996-09-25
US6387941B1 (en)	2002-05-14
NO303388B1 (no)	1998-07-06
FI931558A0 (fi)	1993-04-06
RU94045897A (ru)	1996-09-10
IL105206A0 (en)	1993-07-08
KR950700906A (ko)	1995-02-20
US6150388A (en)	2000-11-21
BR9306201A (pt)	1998-06-23
CZ246494A3 (en)	1995-06-14
YU23893A (sh)	1996-10-09
US6410739B1 (en)	2002-06-25
EP0635017A1 (en)	1995-01-25
KR0179072B1 (ko)	1999-03-20
US6436957B1 (en)	2002-08-20
HUT64062A (en)	1993-11-29
NO943762D0 (no)	1994-10-06
PL172405B1 (en)	1997-09-30
AU670579B2 (en)	1996-07-25

Legal Events

Date	Code	Title	Description
1994-10-31	A1OB	Publication of a patent application
1995-04-27	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2004-01-02	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20040102 Year of fee payment: 12
2007-01-18	ODBI	Application refused

Publication	Publication Date	Title
HRP930752A2 (en)	1994-10-31	Indole derivatives
EP0629199B1 (en)	2002-06-05	Indole derivatives as 5-ht1 agonists
EP0635015B1 (en)	1997-01-29	Acylaminoindole derivatives as 5-ht1 agonists
ES2257168B1 (es)	2007-06-01	Ligandos del receptor 5-ht7.
ES2370877T3 (es)	2011-12-23	Antagonistas del receptor 5-ht7
US6380233B1 (en)	2002-04-30	Indole derivatives as 5-HT1 agonists
KR101174980B1 (ko)	2012-08-17	Ｎｋ３ 수용체 길항제로서의 피페리딘 유도체
IL121326A (en)	2002-09-12	N-substituted pyrolidin-2-yl methyl indole derivatives
RU2059623C1 (ru)	1996-05-10	Тетрагидробензимидазольное производное или его фармацевтически приемлемая соль и фармацевтическая композиция на его основе, проявляющая активность 5-ht3-антагониста
IL118910A (en)	1999-01-26	Intermediates for the synthesis of indole derivatives