IL110793A - History of Benzopuran 2 Phenylpiperidine 3 Methylamine Ion Preparation and Pharmaceutical Preparations Containing Them - Google Patents

History of Benzopuran 2 Phenylpiperidine 3 Methylamine Ion Preparation and Pharmaceutical Preparations Containing Them

Info

Publication number: IL110793A
Authority: IL; Israel
Prior art keywords: benzofuran; phenyl; formula; compound; methyl
Prior art date: 1993-08-26

Application number

IL11079394A

Other languages

English (en)

Hebrew (he)

Other versions

IL110793A0 (en

Original Assignee

Glaxo Group Ltd

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.)

1993-08-26

Filing date

1994-08-26

Publication date

1998-09-24

1994-08-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1994-11-11 Publication of IL110793A0 publication Critical patent/IL110793A0/xx

1998-09-24 Publication of IL110793A publication Critical patent/IL110793A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 14
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
-1 2-phenylpiperidin-3-yl-methylamine benzofuran derivatives Chemical class 0.000 title description 30
150000003839 salts Chemical class 0.000 claims abstract description 34
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
239000012453 solvate Substances 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
238000011282 treatment Methods 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
239000005864 Sulphur Chemical group 0.000 claims abstract description 7
102000003141 Tachykinin Human genes 0.000 claims abstract description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
125000005842 heteroatom Chemical group 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
239000001301 oxygen Substances 0.000 claims abstract description 7
108060008037 tachykinin Proteins 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
230000001404 mediated effect Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 181
150000003536 tetrazoles Chemical group 0.000 claims description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 8
102100024304 Protachykinin-1 Human genes 0.000 claims description 8
101800003906 Substance P Proteins 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 7
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
238000010511 deprotection reaction Methods 0.000 claims description 5
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
150000003852 triazoles Chemical group 0.000 claims description 4
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 abstract description 22
230000008569 process Effects 0.000 abstract description 10
150000001907 coumarones Chemical class 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
239000000203 mixture Substances 0.000 description 77
239000000543 intermediate Substances 0.000 description 71
239000000243 solution Substances 0.000 description 61
239000003921 oil Substances 0.000 description 53
235000019198 oils Nutrition 0.000 description 53
229940093499 ethyl acetate Drugs 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
239000007787 solid Substances 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
NNAFFZPDGFKEFW-UHFFFAOYSA-N azane;dichloromethane;ethanol Chemical compound N.CCO.ClCCl NNAFFZPDGFKEFW-UHFFFAOYSA-N 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
235000019441 ethanol Nutrition 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 36
238000010992 reflux Methods 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
239000002904 solvent Substances 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
239000000706 filtrate Substances 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
239000012074 organic phase Substances 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
239000000843 powder Substances 0.000 description 20
238000000746 purification Methods 0.000 description 19
206010047700 Vomiting Diseases 0.000 description 16
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
239000003826 tablet Substances 0.000 description 15
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
238000003756 stirring Methods 0.000 description 14
229910021529 ammonia Inorganic materials 0.000 description 13
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
239000012267 brine Substances 0.000 description 11
239000000284 extract Substances 0.000 description 11
238000009472 formulation Methods 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
JDFPHOYYVVDYAH-UHFFFAOYSA-N 5-bromo-1-benzofuran-7-carbaldehyde Chemical compound BrC1=CC(C=O)=C2OC=CC2=C1 JDFPHOYYVVDYAH-UHFFFAOYSA-N 0.000 description 9
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 9
125000000623 heterocyclic group Chemical group 0.000 description 9
208000002193 Pain Diseases 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
201000006549 dyspepsia Diseases 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
239000012321 sodium triacetoxyborohydride Substances 0.000 description 7
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 7
DEPICKOSUIUOMZ-UHFFFAOYSA-N tributyl-[7-(1,3-dioxan-2-yl)-1-benzofuran-5-yl]stannane Chemical compound C=12OC=CC2=CC([Sn](CCCC)(CCCC)CCCC)=CC=1C1OCCCO1 DEPICKOSUIUOMZ-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000006071 cream Substances 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
125000001153 fluoro group Chemical group F* 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
239000012071 phase Substances 0.000 description 6
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
GFMAFYNUQDLPBP-QWRGUYRKSA-N (2s,3s)-2-phenylpiperidin-3-amine Chemical compound N[C@H]1CCCN[C@H]1C1=CC=CC=C1 GFMAFYNUQDLPBP-QWRGUYRKSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
230000005855 radiation Effects 0.000 description 5
SWVDNQQJGHNFSU-UHFFFAOYSA-N 5-azido-7-(1,3-dioxan-5-yl)-1-benzofuran Chemical compound C=12OC=CC2=CC(N=[N+]=[N-])=CC=1C1COCOC1 SWVDNQQJGHNFSU-UHFFFAOYSA-N 0.000 description 4
229920003084 Avicel® PH-102 Polymers 0.000 description 4
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000013058 crude material Substances 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000001640 fractional crystallisation Methods 0.000 description 4
208000024798 heartburn Diseases 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
239000012528 membrane Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000001665 trituration Methods 0.000 description 4
239000008215 water for injection Substances 0.000 description 4
JXLWLMUYNWAOOD-UHFFFAOYSA-N 5-bromo-7-(1,3-dioxan-2-yl)-1-benzofuran Chemical compound C=12OC=CC2=CC(Br)=CC=1C1OCCCO1 JXLWLMUYNWAOOD-UHFFFAOYSA-N 0.000 description 3
QDEMNRTYZBBVAI-UHFFFAOYSA-N 7-methyl-1-benzofuran-5-amine Chemical compound CC1=CC(N)=CC2=C1OC=C2 QDEMNRTYZBBVAI-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000004342 Benzoyl peroxide Substances 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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 3
208000019695 Migraine disease Diseases 0.000 description 3
241000282341 Mustela putorius furo Species 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
230000000172 allergic effect Effects 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000007429 general method Methods 0.000 description 3
230000008570 general process Effects 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
208000027866 inflammatory disease Diseases 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
206010027599 migraine Diseases 0.000 description 3
239000002674 ointment Substances 0.000 description 3
208000033808 peripheral neuropathy Diseases 0.000 description 3
239000011698 potassium fluoride Substances 0.000 description 3
235000003270 potassium fluoride Nutrition 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
125000003226 pyrazolyl group Chemical group 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
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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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- 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
- C07D405/12—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 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
- C07D405/14—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 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
- C07D413/14—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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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

IL11079394A 1993-08-26 1994-08-26 History of Benzopuran 2 Phenylpiperidine 3 Methylamine Ion Preparation and Pharmaceutical Preparations Containing Them IL110793A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939317987A GB9317987D0 (en)	1993-08-26	1993-08-26	Chemical compounds

Publications (2)

Publication Number	Publication Date
IL110793A0 IL110793A0 (en)	1994-11-11
IL110793A true IL110793A (en)	1998-09-24

Family

ID=10741251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11079394A IL110793A (en)	1993-08-26	1994-08-26	History of Benzopuran 2 Phenylpiperidine 3 Methylamine Ion Preparation and Pharmaceutical Preparations Containing Them

Country Status (16)

Country	Link
US (1)	US5935972A (de)
EP (1)	EP0783499B1 (de)
JP (1)	JP3499243B2 (de)
AP (1)	AP9400666A0 (de)
AT (1)	ATE226578T1 (de)
AU (1)	AU7655094A (de)
CO (1)	CO4230233A1 (de)
DE (1)	DE69431604T2 (de)
EC (1)	ECSP941146A (de)
ES (1)	ES2185665T3 (de)
GB (1)	GB9317987D0 (de)
IL (1)	IL110793A (de)
IS (1)	IS4201A (de)
PE (1)	PE14995A1 (de)
WO (1)	WO1995006645A1 (de)
ZA (1)	ZA946470B (de)

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1993
- 1993-08-26 GB GB939317987A patent/GB9317987D0/en active Pending
1994
- 1994-08-23 EC EC1994001146A patent/ECSP941146A/es unknown
- 1994-08-24 ZA ZA946470A patent/ZA946470B/xx unknown
- 1994-08-25 CO CO94037843A patent/CO4230233A1/es unknown
- 1994-08-25 JP JP50792395A patent/JP3499243B2/ja not_active Expired - Fee Related
- 1994-08-25 AT AT94926877T patent/ATE226578T1/de not_active IP Right Cessation
- 1994-08-25 DE DE69431604T patent/DE69431604T2/de not_active Expired - Fee Related
- 1994-08-25 WO PCT/EP1994/002804 patent/WO1995006645A1/en not_active Ceased
- 1994-08-25 EP EP94926877A patent/EP0783499B1/de not_active Expired - Lifetime
- 1994-08-25 US US08/793,099 patent/US5935972A/en not_active Expired - Fee Related
- 1994-08-25 AU AU76550/94A patent/AU7655094A/en not_active Abandoned
- 1994-08-25 ES ES94926877T patent/ES2185665T3/es not_active Expired - Lifetime
- 1994-08-25 AP APAP/P/1994/000666A patent/AP9400666A0/en unknown
- 1994-08-25 IS IS4201A patent/IS4201A/is unknown
- 1994-08-25 PE PE1994249244A patent/PE14995A1/es not_active Application Discontinuation
- 1994-08-26 IL IL11079394A patent/IL110793A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
CO4230233A1 (es)	1995-10-19
JPH10508824A (ja)	1998-09-02
GB9317987D0 (en)	1993-10-13
ZA946470B (en)	1995-11-14
EP0783499B1 (de)	2002-10-23
WO1995006645A1 (en)	1995-03-09
PE14995A1 (es)	1995-06-04
AP9400666A0 (en)	1994-10-31
IS4201A (is)	1995-03-01
ECSP941146A (es)	1995-01-16
ATE226578T1 (de)	2002-11-15
DE69431604T2 (de)	2003-06-26
JP3499243B2 (ja)	2004-02-23
EP0783499A1 (de)	1997-07-16
ES2185665T3 (es)	2003-05-01
US5935972A (en)	1999-08-10
IL110793A0 (en)	1994-11-11
DE69431604D1 (de)	2002-11-28
AU7655094A (en)	1995-03-22

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-07-14	KB	Patent renewed
2000-10-31	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0783499B1 (de)	2002-10-23	Benzofuranderivate als tachykininantagonisten
US12291529B2 (en)	2025-05-06	Heterocyclic GLP-1 agonists
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AP495A (en)	1996-05-28	Piperidine derivatives
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AU2004228120B2 (en)	2010-12-02	Substituted pyrazoles
EP0799231B1 (de)	1999-03-17	Spiroketalderivate, diese enthaltende zusammensetzungen und ihre verwendung als arzneimittel
TW200825071A (en)	2008-06-16	Indole compound
WO1997001553A1 (en)	1997-01-16	Piperidine and morpholine derivatives and their use as therapeutic agents
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JP2001513764A (ja)	2001-09-04	５−ｈｔ２ａ拮抗剤としてのオキサゾリジン類
US5444074A (en)	1995-08-22	Piperidine tachykinin receptor antagonists
EP0501568B1 (de)	1997-08-20	Substituiertes cyclisches Sulfamidderivat
EP0347229A1 (de)	1989-12-20	Indol-Derivate
JPH10513172A (ja)	1998-12-15	５−ｈｔ▲下１ｄ▼受容体アゴニストとしての置換１，４−ピペラジン−ヘテロアリール誘導体
JP3752130B2 (ja)	2006-03-08	掻痒治療用新規４−アリールピペリジン誘導体
JP2002535308A (ja)	2002-10-22	５−ｈｔ受容体リガンドとしてのフェニルスルホニル誘導体
JPS60214784A (ja)	1985-10-28	複素環式化合物
CA2245579A1 (en)	1997-08-21	Spiro-ketal derivatives and their use as therapeutic agents