OA10666A - Substituted benyzlaminopiperidine compounds - Google Patents

Substituted benyzlaminopiperidine compounds Download PDF

Info

Publication number: OA10666A
Authority: OA; OAPI
Prior art keywords: compound; salts; trifluoromethyl; halo; phenylpiperidine
Prior art date: 1995-08-24

Application number

OA9800023A

Other languages

English (en)

Inventor

Kunio Satake

Yuji Shishido

Hiroaki Wakabayashi

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.)

1995-08-24

Filing date

1998-02-23

Publication date

2002-11-25

1998-02-23 Application filed by Pfizer filed Critical Pfizer

2002-11-25 Publication of OA10666A publication Critical patent/OA10666A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 209
150000003839 salts Chemical class 0.000 claims abstract description 64
-1 halo C1-C6 alkoxy Chemical group 0.000 claims abstract description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
208000015114 central nervous system disease Diseases 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
208000035475 disorder Diseases 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 7
208000019695 Migraine disease Diseases 0.000 claims abstract description 7
208000002193 Pain Diseases 0.000 claims abstract description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
206010027599 migraine Diseases 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
206010046543 Urinary incontinence Diseases 0.000 claims abstract description 6
230000002411 adverse Effects 0.000 claims abstract description 6
230000033115 angiogenesis Effects 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 6
201000010099 disease Diseases 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
208000010643 digestive system disease Diseases 0.000 claims abstract description 4
208000018685 gastrointestinal system disease Diseases 0.000 claims abstract description 4
206010042496 Sunburn Diseases 0.000 claims abstract 2
125000005843 halogen group Chemical group 0.000 claims description 44
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims description 5
125000001118 alkylidene group Chemical group 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims description 3
208000012902 Nervous system disease Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
XQDSIGDVDWFZPP-UHFFFAOYSA-N 2-phenylpiperidin-1-amine Chemical compound NN1CCCCC1C1=CC=CC=C1 XQDSIGDVDWFZPP-UHFFFAOYSA-N 0.000 claims 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
206010047700 Vomiting Diseases 0.000 abstract description 7
210000003169 central nervous system Anatomy 0.000 abstract description 4
125000001475 halogen functional group Chemical group 0.000 abstract 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
241000590002 Helicobacter pylori Species 0.000 abstract 1
229940037467 helicobacter pylori Drugs 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 63
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
101150041968 CDC13 gene Proteins 0.000 description 55
239000000243 solution Substances 0.000 description 54
239000000203 mixture Substances 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
239000012043 crude product Substances 0.000 description 32
239000003921 oil Substances 0.000 description 31
235000019198 oils Nutrition 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000012267 brine Substances 0.000 description 19
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 18
229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
235000017557 sodium bicarbonate Nutrition 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
239000007787 solid Substances 0.000 description 17
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
238000000746 purification Methods 0.000 description 14
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
229940125797 compound 12 Drugs 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012458 free base Substances 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 11
229940093499 ethyl acetate Drugs 0.000 description 11
239000010410 layer Substances 0.000 description 11
150000003053 piperidines Chemical class 0.000 description 11
239000002904 solvent Substances 0.000 description 11
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 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
102100024304 Protachykinin-1 Human genes 0.000 description 10
101800003906 Substance P Proteins 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000000725 suspension Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
235000019439 ethyl acetate Nutrition 0.000 description 8
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 7
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229940125851 compound 27 Drugs 0.000 description 7
239000000284 extract Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000012065 filter cake Substances 0.000 description 6
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 5
241000282412 Homo Species 0.000 description 5
239000007832 Na2SO4 Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229910003074 TiCl4 Inorganic materials 0.000 description 5
230000027455 binding Effects 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
229940125844 compound 46 Drugs 0.000 description 5
GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
CYHZEBLRMBOVSV-UHFFFAOYSA-N 2-phenoxy-5-(trifluoromethyl)benzaldehyde Chemical compound O=CC1=CC(C(F)(F)F)=CC=C1OC1=CC=CC=C1 CYHZEBLRMBOVSV-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
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229940125782 compound 2 Drugs 0.000 description 4
229940126086 compound 21 Drugs 0.000 description 4
229940125961 compound 24 Drugs 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
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BWSDNRQVTFZQQD-AYVHNPTNSA-N phosphoramidon Chemical compound O([P@@](O)(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC=1[C]2C=CC=CC2=NC=1)C(O)=O)[C@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O BWSDNRQVTFZQQD-AYVHNPTNSA-N 0.000 description 1
108010072906 phosphoramidon Proteins 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
OHEDMAIVEXQCOZ-UHFFFAOYSA-N piperidine;dihydrochloride Chemical compound Cl.Cl.C1CCNCC1 OHEDMAIVEXQCOZ-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000010079 rubber tapping Methods 0.000 description 1
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
SCWLIHXXYXFUFV-UHFFFAOYSA-M sodium;2,2,3,3,3-pentafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)(F)F SCWLIHXXYXFUFV-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
238000006692 trifluoromethylation reaction Methods 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen 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
- A61P13/00—Drugs for disorders of the urinary 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
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (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)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Urology & Nephrology (AREA)
Psychiatry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

OA9800023A 1995-08-24 1998-02-23 Substituted benyzlaminopiperidine compounds OA10666A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IB9500683		1995-08-24

Publications (1)

Publication Number	Publication Date
OA10666A true OA10666A (en)	2002-11-25

Family

ID=11004362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9800023A OA10666A (en)	1995-08-24	1998-02-23	Substituted benyzlaminopiperidine compounds

Country Status (42)

Country	Link
US (1)	US6506775B1 (zh)
EP (2)	EP1114817B1 (zh)
JP (1)	JP3084069B2 (zh)
KR (1)	KR100288673B1 (zh)
CN (1)	CN1153764C (zh)
AP (1)	AP643A (zh)
AR (1)	AR006305A1 (zh)
AT (2)	ATE258166T1 (zh)
AU (1)	AU702698B2 (zh)
BG (1)	BG64126B1 (zh)
BR (1)	BR9609989A (zh)
CA (1)	CA2227814C (zh)
CO (1)	CO4480738A1 (zh)
CZ (1)	CZ297543B6 (zh)
DE (2)	DE69616817T2 (zh)
DK (2)	DK0861235T3 (zh)
DZ (1)	DZ2086A1 (zh)
ES (2)	ES2163017T3 (zh)
HK (1)	HK1014935A1 (zh)
HR (1)	HRP960386B1 (zh)
HU (1)	HU225480B1 (zh)
IL (1)	IL119078A (zh)
IS (1)	IS1947B (zh)
MA (1)	MA23961A1 (zh)
MX (1)	MX9801467A (zh)
MY (1)	MY114800A (zh)
NO (1)	NO310720B1 (zh)
NZ (1)	NZ308207A (zh)
OA (1)	OA10666A (zh)
PE (2)	PE20010700A1 (zh)
PL (1)	PL186773B1 (zh)
PT (2)	PT861235E (zh)
RO (1)	RO119299B1 (zh)
RU (1)	RU2152930C2 (zh)
SI (2)	SI1114817T1 (zh)
SK (1)	SK282925B6 (zh)
TN (1)	TNSN96107A1 (zh)
TR (1)	TR199800300T1 (zh)
TW (1)	TW340842B (zh)
UA (1)	UA48981C2 (zh)
WO (1)	WO1997008144A1 (zh)
YU (1)	YU49122B (zh)

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1996
- 1996-06-04 TW TW085106675A patent/TW340842B/zh active
- 1996-06-10 PL PL96325332A patent/PL186773B1/pl not_active IP Right Cessation
- 1996-06-10 TN TNTNSN96107A patent/TNSN96107A1/fr unknown
- 1996-06-10 DE DE69616817T patent/DE69616817T2/de not_active Expired - Fee Related
- 1996-06-10 DK DK96914375T patent/DK0861235T3/da active
- 1996-06-10 BR BR9609989A patent/BR9609989A/pt not_active Application Discontinuation
- 1996-06-10 AU AU57769/96A patent/AU702698B2/en not_active Ceased
- 1996-06-10 RU RU98102959/04A patent/RU2152930C2/ru not_active IP Right Cessation
- 1996-06-10 JP JP09510015A patent/JP3084069B2/ja not_active Expired - Fee Related
- 1996-06-10 TR TR1998/00300T patent/TR199800300T1/xx unknown
- 1996-06-10 HU HU9901159A patent/HU225480B1/hu not_active IP Right Cessation
- 1996-06-10 EP EP01108350A patent/EP1114817B1/en not_active Expired - Lifetime
- 1996-06-10 EP EP96914375A patent/EP0861235B1/en not_active Expired - Lifetime
- 1996-06-10 NZ NZ308207A patent/NZ308207A/en unknown
- 1996-06-10 CA CA002227814A patent/CA2227814C/en not_active Expired - Fee Related
- 1996-06-10 ES ES96914375T patent/ES2163017T3/es not_active Expired - Lifetime
- 1996-06-10 KR KR1019980701310A patent/KR100288673B1/ko not_active IP Right Cessation
- 1996-06-10 PT PT96914375T patent/PT861235E/pt unknown
- 1996-06-10 SI SI9630670T patent/SI1114817T1/xx unknown
- 1996-06-10 PT PT01108350T patent/PT1114817E/pt unknown
- 1996-06-10 DK DK01108350T patent/DK1114817T3/da active
- 1996-06-10 UA UA98020924A patent/UA48981C2/uk unknown
- 1996-06-10 ES ES01108350T patent/ES2211684T3/es not_active Expired - Lifetime
- 1996-06-10 AT AT01108350T patent/ATE258166T1/de not_active IP Right Cessation
- 1996-06-10 AT AT96914375T patent/ATE208377T1/de not_active IP Right Cessation
- 1996-06-10 CZ CZ0052198A patent/CZ297543B6/cs not_active IP Right Cessation
- 1996-06-10 DE DE69631390T patent/DE69631390T2/de not_active Expired - Fee Related
- 1996-06-10 MX MX9801467A patent/MX9801467A/es active IP Right Grant
- 1996-06-10 SI SI9630374T patent/SI0861235T1/xx unknown
- 1996-06-10 WO PCT/IB1996/000572 patent/WO1997008144A1/en active IP Right Grant
- 1996-06-10 SK SK207-98A patent/SK282925B6/sk not_active IP Right Cessation
- 1996-06-10 RO RO98-00334A patent/RO119299B1/ro unknown
- 1996-06-10 CN CNB961965037A patent/CN1153764C/zh not_active Expired - Fee Related
- 1996-08-15 IL IL11907896A patent/IL119078A/xx not_active IP Right Cessation
- 1996-08-20 AR ARP960104045A patent/AR006305A1/es active IP Right Grant
- 1996-08-21 PE PE2001000276A patent/PE20010700A1/es not_active Application Discontinuation
- 1996-08-21 DZ DZ960130A patent/DZ2086A1/fr active
- 1996-08-21 PE PE1996000625A patent/PE1398A1/es not_active Application Discontinuation
- 1996-08-22 HR HR960386A patent/HRP960386B1/xx not_active IP Right Cessation
- 1996-08-23 MY MYPI96003496A patent/MY114800A/en unknown
- 1996-08-23 YU YU47896A patent/YU49122B/sh unknown
- 1996-08-23 MA MA24339A patent/MA23961A1/fr unknown
- 1996-08-24 AP APAP/P/1996/000850A patent/AP643A/en active
- 1996-08-26 CO CO96045248A patent/CO4480738A1/es unknown
1997
- 1997-12-30 IS IS4644A patent/IS1947B/is unknown
1998
- 1998-02-23 OA OA9800023A patent/OA10666A/en unknown
- 1998-02-23 NO NO19980751A patent/NO310720B1/no unknown
- 1998-02-27 BG BG102288A patent/BG64126B1/bg unknown
- 1998-12-30 HK HK98119203A patent/HK1014935A1/xx not_active IP Right Cessation
2000
- 2000-05-01 US US09/564,398 patent/US6506775B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HRP960386B1 (en)	2002-04-30
DZ2086A1 (fr)	2002-07-22
CN1153764C (zh)	2004-06-16
MX9801467A (es)	1998-05-31
ES2211684T3 (es)	2004-07-16
PE20010700A1 (es)	2001-07-09
UA48981C2 (uk)	2002-09-16
US6506775B1 (en)	2003-01-14
EP1114817B1 (en)	2004-01-21
TR199800300T1 (xx)	1998-06-22
HK1014935A1 (en)	1999-10-08
YU47896A (sh)	1998-12-23
HRP960386A2 (en)	1998-04-30
DE69616817T2 (de)	2002-04-04
IL119078A0 (en)	1996-11-14
PE1398A1 (es)	1998-02-27
SK20798A3 (en)	1999-03-12
NO310720B1 (no)	2001-08-20
CZ297543B6 (cs)	2007-02-07
NO980751L (no)	1998-02-23
AR006305A1 (es)	1999-08-25
AU702698B2 (en)	1999-03-04
YU49122B (sh)	2004-03-12
IL119078A (en)	2003-11-23
TW340842B (en)	1998-09-21
JPH10510554A (ja)	1998-10-13
NZ308207A (en)	1998-07-28
BG102288A (en)	1998-09-30
CA2227814A1 (en)	1997-03-06
JP3084069B2 (ja)	2000-09-04
PT861235E (pt)	2002-03-28
BG64126B1 (bg)	2004-01-30
DE69631390D1 (de)	2004-02-26
HU225480B1 (en)	2006-12-28
BR9609989A (pt)	1999-07-06
CA2227814C (en)	2002-12-31
PT1114817E (pt)	2004-05-31
CZ52198A3 (cs)	1999-01-13
IS4644A (is)	1997-12-30
DK0861235T3 (da)	2001-12-27
CN1193961A (zh)	1998-09-23
IS1947B (is)	2004-10-13
KR19990044077A (ko)	1999-06-25
CO4480738A1 (es)	1997-07-09
PL325332A1 (en)	1998-07-20
SI1114817T1 (en)	2004-06-30
SK282925B6 (sk)	2003-01-09
AP9600850A0 (en)	1996-10-31
ES2163017T3 (es)	2002-01-16
EP1114817A1 (en)	2001-07-11
HUP9901159A3 (en)	2000-05-29
TNSN96107A1 (fr)	2005-03-15
EP0861235A1 (en)	1998-09-02
EP0861235B1 (en)	2001-11-07
KR100288673B1 (ko)	2001-05-02
DE69631390T2 (de)	2004-11-25
ATE258166T1 (de)	2004-02-15
AP643A (en)	1998-04-24
RU2152930C2 (ru)	2000-07-20
MY114800A (en)	2003-01-31
PL186773B1 (pl)	2004-02-27
HUP9901159A2 (hu)	1999-07-28
DK1114817T3 (da)	2004-04-26
ATE208377T1 (de)	2001-11-15
SI0861235T1 (en)	2002-04-30
AU5776996A (en)	1997-03-19
DE69616817D1 (de)	2001-12-13
RO119299B1 (ro)	2004-07-30
WO1997008144A1 (en)	1997-03-06
MA23961A1 (fr)	1997-04-01
NO980751D0 (no)	1998-02-23

Publication	Publication Date	Title
OA10666A (en)	2002-11-25	Substituted benyzlaminopiperidine compounds
EP0699199B1 (en)	2002-11-20	Heteroatom substituted alkyl benzylaminoquinuclidines as substance p antagonists
JP2500279B2 (ja)	1996-05-29	アザ二環式化合物、これを含有する医薬組成物及び治療のための使用方法
JPH0757748B2 (ja)	1995-06-21	３−アミノピペリジン誘導体及び関連する窒素含有複素環化合物
CA2310627C (en)	2005-08-09	Piperidinylaminomethyl trifluoromethyl cyclic ether compounds as substance p antagonists
US5789423A (en)	1998-08-04	3- 5-substituted benzyl)amino!-2-phenylpiperidines as substance P antagonists
EP1165528B1 (fr)	2004-09-01	Nouveaux derives de morpholine, procede pour leur preparation et compositions pharmaceutiques les contenant
US6329396B1 (en)	2001-12-11	Substituted benzylaminopiperidine compounds
US4705807A (en)	1987-11-10	Amine derivatives
IL93814A (en)	1995-07-31	History of benzothiophyranilamines, their preparation and pharmaceutical preparations containing them
MXPA06001194A (es)	2006-05-15	Derivado de bencilamina.
JP3172461B2 (ja)	2001-06-04	サブスタンスｐアンタゴニストとしての３−［（５−置換ベンジル）アミノ］−２−フェニルピペリジン
JP2756732B2 (ja)	1998-05-25	リポキシゲナーゼ阻害剤としてのフェニルチオフェニルシクロアルケニルヒドロキシ尿素
FR2729952A1 (fr)	1996-08-02	Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant
JP2500279C (zh)	1999-07-05
JPS5939419B2 (ja)	1984-09-22	カテコ−ル誘導体の製造法
DK159152B (da)	1990-09-10	Analogifremgangsmaade til fremstilling af terapeutisk virksomme pyrimidooe1,6-aaa-indolderivater eller salte deraf.