NO881388L - Fremgangsmaate for fremstilling av 4-fenylpiperidinforbindelser. - Google Patents

Fremgangsmaate for fremstilling av 4-fenylpiperidinforbindelser.

Info

Publication number: NO881388L
Authority: NO; Norway
Prior art keywords: compound; general formula; alkyl; phenylpiperidine; meaning
Prior art date: 1987-03-31

Application number

NO881388A

Other languages

English (en)

Norwegian (no)

Other versions

NO881388D0 (no

Inventor

Frank Waetjen

Original Assignee

Ferrosan As

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.)

1987-03-31

Filing date

1988-03-29

Publication date

1988-10-03

1988-03-29 Application filed by Ferrosan As filed Critical Ferrosan As

1988-03-29 Publication of NO881388D0 publication Critical patent/NO881388D0/no

1988-10-03 Publication of NO881388L publication Critical patent/NO881388L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 68
238000000034 method Methods 0.000 title description 4
238000002360 preparation method Methods 0.000 title description 2
208000002193 Pain Diseases 0.000 claims description 19
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
-1 4-Phenylpiperidine compound Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
GXUMKNVWYXEBHC-UHFFFAOYSA-N 3-cyclopropyl-5-(4-phenylpiperidin-4-yl)-1,2,4-oxadiazole Chemical group C1CC1C1=NOC(C2(CCNCC2)C=2C=CC=CC=2)=N1 GXUMKNVWYXEBHC-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000012380 dealkylating agent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
QJMFFSOZBGDBTE-UHFFFAOYSA-N 3-cyclopropyl-5-[1-(2-ethoxyethyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole Chemical group C1CN(CCOCC)CCC1(C=1C=CC=CC=1)C1=NC(C2CC2)=NO1 QJMFFSOZBGDBTE-UHFFFAOYSA-N 0.000 claims 1
FSGWOZSKAFADSY-UHFFFAOYSA-N 5-(1-methyl-4-phenylpiperidin-4-yl)-3-phenyl-1,2,4-oxadiazole Chemical group C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C=2C=CC=CC=2)=NO1 FSGWOZSKAFADSY-UHFFFAOYSA-N 0.000 claims 1
125000004171 alkoxy aryl group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
BTNNHDOOHOMCLX-UHFFFAOYSA-N n-methoxy-1-(1-methyl-4-phenylpiperidin-4-yl)methanimine Chemical group C=1C=CC=CC=1C1(C=NOC)CCN(C)CC1 BTNNHDOOHOMCLX-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 8
239000000203 mixture Substances 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 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
239000002775 capsule Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
150000003053 piperidines Chemical class 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
208000011580 syndromic disease Diseases 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VZJYRFYOYJFCMV-UHFFFAOYSA-N 1-methyl-4-phenylpiperidine-4-carbaldehyde Chemical compound C1CN(C)CCC1(C=O)C1=CC=CC=C1 VZJYRFYOYJFCMV-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
206010038419 Renal colic Diseases 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
208000005298 acute pain Diseases 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000012458 free base Substances 0.000 description 2
208000001130 gallstones Diseases 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 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
AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
229960000482 pethidine Drugs 0.000 description 2
KHUPPYUUMRDAAX-UHFFFAOYSA-N pethidinic acid Chemical compound C1CN(C)CCC1(C(O)=O)C1=CC=CC=C1 KHUPPYUUMRDAAX-UHFFFAOYSA-N 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FDIJINBEVKPNEC-UHFFFAOYSA-N (1-methyl-4-phenylpiperidin-4-yl)methanol Chemical compound C1CN(C)CCC1(CO)C1=CC=CC=C1 FDIJINBEVKPNEC-UHFFFAOYSA-N 0.000 description 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
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 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
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 1
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 1
IGJUYVFAGFNDBJ-UHFFFAOYSA-N 2-chloro-6-fluoro-n'-hydroxybenzenecarboximidamide Chemical compound ON=C(N)C1=C(F)C=CC=C1Cl IGJUYVFAGFNDBJ-UHFFFAOYSA-N 0.000 description 1
UQVCPKNHQRKCGJ-UHFFFAOYSA-N 2-fluoro-n'-hydroxybenzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC=C1F UQVCPKNHQRKCGJ-UHFFFAOYSA-N 0.000 description 1
QKPVEISEHYYHRH-UHFFFAOYSA-N 2-methoxyacetonitrile Chemical compound COCC#N QKPVEISEHYYHRH-UHFFFAOYSA-N 0.000 description 1
MIVSVNDQRYMELF-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C=2C(=CC=CC=2F)Cl)=NO1 MIVSVNDQRYMELF-UHFFFAOYSA-N 0.000 description 1
RYBFCFIDBMLMOF-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-(1-methyl-4-phenylpiperidin-2-yl)-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.CN1CCC(C=2C=CC=CC=2)CC1C(ON=1)=NC=1C1=CC=CC=C1F RYBFCFIDBMLMOF-UHFFFAOYSA-N 0.000 description 1
HVRHIMREMYDICA-UHFFFAOYSA-N 3-(methoxymethyl)-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;hydrochloride Chemical compound Cl.COCC1=NOC(C2(CCN(C)CC2)C=2C=CC=CC=2)=N1 HVRHIMREMYDICA-UHFFFAOYSA-N 0.000 description 1
KUVOAFHBCHHXKB-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.COC1=CC=CC=C1CC1=NOC(C2(CCN(C)CC2)C=2C=CC=CC=2)=N1 KUVOAFHBCHHXKB-UHFFFAOYSA-N 0.000 description 1
VQZMMPXSRBEDMK-UHFFFAOYSA-N 3-cyclopropyl-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;hydrochloride Chemical compound Cl.C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C2CC2)=NO1 VQZMMPXSRBEDMK-UHFFFAOYSA-N 0.000 description 1
WAKQVEOLPDDXKN-UHFFFAOYSA-N 3-cyclopropyl-5-[1-(2-ethoxyethyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCOCC)CCC1(C=1C=CC=CC=1)C1=NC(C2CC2)=NO1 WAKQVEOLPDDXKN-UHFFFAOYSA-N 0.000 description 1
ABDWCQVVTDDBGN-UHFFFAOYSA-N 3-cyclopropyl-5-[1-(2-methoxyethyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCOC)CCC1(C=1C=CC=CC=1)C1=NC(C2CC2)=NO1 ABDWCQVVTDDBGN-UHFFFAOYSA-N 0.000 description 1
VQMHLIUAJWINEI-UHFFFAOYSA-N 3-cyclopropyl-5-[1-(4-phenoxybutyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1OCCCCN(CC1)CCC1(C=1C=CC=CC=1)C(ON=1)=NC=1C1CC1 VQMHLIUAJWINEI-UHFFFAOYSA-N 0.000 description 1
IFJNCYMQDOUSJR-UHFFFAOYSA-N 3-cyclopropyl-5-[1-(cyclopropylmethyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole;hydrochloride Chemical compound Cl.C1CC(C=2C=CC=CC=2)(C=2ON=C(N=2)C2CC2)CCN1CC1CC1 IFJNCYMQDOUSJR-UHFFFAOYSA-N 0.000 description 1
NNOHSABFKOOKBD-UHFFFAOYSA-N 3-methyl-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole Chemical compound C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C)=NO1 NNOHSABFKOOKBD-UHFFFAOYSA-N 0.000 description 1
FUBGHDHGUJBJBJ-UHFFFAOYSA-N 3-methyl-5-(1-methyl-4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;hydrochloride Chemical compound Cl.C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C)=NO1 FUBGHDHGUJBJBJ-UHFFFAOYSA-N 0.000 description 1
LUXXRZFTIFORQC-UHFFFAOYSA-N 3-methyl-5-(4-phenylpiperidin-4-yl)-1,2,4-oxadiazole Chemical compound CC1=NOC(C2(CCNCC2)C=2C=CC=CC=2)=N1 LUXXRZFTIFORQC-UHFFFAOYSA-N 0.000 description 1
UTDYNUAXXWTKCW-UHFFFAOYSA-N 3-methyl-5-[1-(2-phenoxyethyl)-4-phenylpiperidin-4-yl]-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.CC1=NOC(C2(CCN(CCOC=3C=CC=CC=3)CC2)C=2C=CC=CC=2)=N1 UTDYNUAXXWTKCW-UHFFFAOYSA-N 0.000 description 1
RVUARTRAWZXFQA-UHFFFAOYSA-N 3-phenyl-5-(4-phenylpiperidin-4-yl)-1,2,4-oxadiazole;hydrochloride Chemical compound Cl.C1CNCCC1(C=1C=CC=CC=1)C1=NC(C=2C=CC=CC=2)=NO1 RVUARTRAWZXFQA-UHFFFAOYSA-N 0.000 description 1
UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical class C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 1
XVYJDMRUOHOLSQ-UHFFFAOYSA-N 5-(1-methyl-4-phenylpiperidin-4-yl)-3-thiophen-2-yl-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C)CCC1(C=1C=CC=CC=1)C1=NC(C=2SC=CC=2)=NO1 XVYJDMRUOHOLSQ-UHFFFAOYSA-N 0.000 description 1
DVOZVTUDVDURAE-UHFFFAOYSA-N 5-[1-(2-benzhydryloxyethyl)-4-phenylpiperidin-4-yl]-3-methyl-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.CC1=NOC(C2(CCN(CCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)C=2C=CC=CC=2)=N1 DVOZVTUDVDURAE-UHFFFAOYSA-N 0.000 description 1
SOOYTBMUKKIAST-UHFFFAOYSA-N 5-[1-(2-ethoxyethyl)-4-phenylpiperidin-4-yl]-3-methyl-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCOCC)CCC1(C=1C=CC=CC=1)C1=NC(C)=NO1 SOOYTBMUKKIAST-UHFFFAOYSA-N 0.000 description 1
HKUOSNUZYBCGSB-UHFFFAOYSA-N 5-[1-(2-ethoxyethyl)-4-phenylpiperidin-4-yl]-3-phenyl-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCOCC)CCC1(C=1C=CC=CC=1)C1=NC(C=2C=CC=CC=2)=NO1 HKUOSNUZYBCGSB-UHFFFAOYSA-N 0.000 description 1
ZEEWJAUWZNIJCB-UHFFFAOYSA-N 5-[1-[2-(4-methoxyphenyl)ethyl]-4-phenylpiperidin-4-yl]-3-phenyl-1,2,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1CCN1CCC(C=2C=CC=CC=2)(C=2ON=C(N=2)C=2C=CC=CC=2)CC1 ZEEWJAUWZNIJCB-UHFFFAOYSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
206010058019 Cancer Pain Diseases 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
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LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
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 1
239000012298 atmosphere Substances 0.000 description 1
MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
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235000011852 gelatine desserts Nutrition 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
OEXWNUSXRCKEQM-UHFFFAOYSA-N n'-hydroxy-2-(2-methoxyphenyl)ethanimidamide Chemical compound COC1=CC=CC=C1CC(N)=NO OEXWNUSXRCKEQM-UHFFFAOYSA-N 0.000 description 1
UNKQCVYVFHGUTQ-UHFFFAOYSA-N n'-hydroxy-2-methoxyethanimidamide Chemical compound COCC(N)=NO UNKQCVYVFHGUTQ-UHFFFAOYSA-N 0.000 description 1
JHRDEHLFNLLCQS-UHFFFAOYSA-N n'-hydroxy-2-methylpropanimidamide Chemical compound CC(C)C(N)=NO JHRDEHLFNLLCQS-UHFFFAOYSA-N 0.000 description 1
OMCUPXRCMTUDHI-UHFFFAOYSA-N n'-hydroxycyclopropanecarboximidamide Chemical compound ON=C(N)C1CC1 OMCUPXRCMTUDHI-UHFFFAOYSA-N 0.000 description 1
XCCXRWMQIFDSFC-UHFFFAOYSA-N n'-hydroxynaphthalene-1-carboximidamide Chemical compound C1=CC=C2C(C(=N/O)/N)=CC=CC2=C1 XCCXRWMQIFDSFC-UHFFFAOYSA-N 0.000 description 1
RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 description 1
NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical compound ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
HMMFZNBOQJOULD-UHFFFAOYSA-N o-(cyclopropylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1CC1 HMMFZNBOQJOULD-UHFFFAOYSA-N 0.000 description 1
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229920001223 polyethylene glycol Polymers 0.000 description 1
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229910052708 sodium Inorganic materials 0.000 description 1
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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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

NO881388A 1987-03-31 1988-03-29 Fremgangsmaate for fremstilling av 4-fenylpiperidinforbindelser. NO881388L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK162087A DK162087D0 (da)	1987-03-31	1987-03-31	Piperidinforbindelser, deres fremstilling og anvendelse

Publications (2)

Publication Number	Publication Date
NO881388D0 NO881388D0 (no)	1988-03-29
NO881388L true NO881388L (no)	1988-10-03

Family

ID=8106610

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO881388A NO881388L (no)	1987-03-31	1988-03-29	Fremgangsmaate for fremstilling av 4-fenylpiperidinforbindelser.

Country Status (12)

Country	Link
US (1)	US4845095A (fi)
EP (1)	EP0285032A1 (fi)
JP (1)	JPS63258456A (fi)
KR (1)	KR880011098A (fi)
AU (1)	AU1379488A (fi)
DK (1)	DK162087D0 (fi)
FI (1)	FI881410A (fi)
IL (1)	IL85612A0 (fi)
NO (1)	NO881388L (fi)
PH (1)	PH24620A (fi)
PT (1)	PT87031B (fi)
ZA (1)	ZA881799B (fi)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU685212B2 (en) *	1994-01-13	1998-01-15	Merck Sharp & Dohme Limited	Gem-disubstituted azacyclic tachykinin antagonists
US6107313A (en) *	1998-10-02	2000-08-22	Combichem, Inc.	Dopamine receptor antagonists
TW200403058A (en) *	2002-04-19	2004-03-01	Bristol Myers Squibb Co	Heterocyclo inhibitors of potassium channel function
US7202259B2 (en) *	2002-11-18	2007-04-10	Euro-Celtique S.A.	Therapeutic agents useful for treating pain
GB0510142D0 (en) *	2005-05-18	2005-06-22	Addex Pharmaceuticals Sa	Novel compounds A1
US11976050B1 (en)	2023-10-11	2024-05-07	King Faisal University	N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-1-naphthimidamide as an antimicrobial compound

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4016170A (en) *	1975-07-28	1977-04-05	Sandoz, Inc.	Oxadiazolyl benzamides

1987
- 1987-03-31 DK DK162087A patent/DK162087D0/da not_active Application Discontinuation
1988
- 1988-03-02 IL IL85612A patent/IL85612A0/xx unknown
- 1988-03-14 ZA ZA881799A patent/ZA881799B/xx unknown
- 1988-03-15 PH PH36639A patent/PH24620A/en unknown
- 1988-03-21 PT PT87031A patent/PT87031B/pt not_active IP Right Cessation
- 1988-03-23 US US07/172,197 patent/US4845095A/en not_active Expired - Fee Related
- 1988-03-24 FI FI881410A patent/FI881410A/fi not_active Application Discontinuation
- 1988-03-25 EP EP88104864A patent/EP0285032A1/en not_active Withdrawn
- 1988-03-28 AU AU13794/88A patent/AU1379488A/en not_active Abandoned
- 1988-03-28 KR KR1019880003338A patent/KR880011098A/ko not_active Application Discontinuation
- 1988-03-29 NO NO881388A patent/NO881388L/no unknown
- 1988-03-30 JP JP63074909A patent/JPS63258456A/ja active Pending

Also Published As

Publication number	Publication date
KR880011098A (ko)	1988-10-26
FI881410A (fi)	1988-10-01
IL85612A0 (en)	1988-08-31
NO881388D0 (no)	1988-03-29
AU1379488A (en)	1988-09-29
PT87031A (pt)	1988-04-01
PH24620A (en)	1990-08-17
DK162087D0 (da)	1987-03-31
ZA881799B (en)	1988-09-05
EP0285032A1 (en)	1988-10-05
JPS63258456A (ja)	1988-10-25
FI881410A0 (fi)	1988-03-24
US4845095A (en)	1989-07-04
PT87031B (pt)	1992-06-30

Publication	Publication Date	Title
DE69229674T2 (de)	2000-04-06	5-ht4 rezeptor antagonisten
EP0296560B1 (en)	1996-02-28	1,4-Substituted piperidines as acetylcholinesterase inhibitors and their use for the treatment of Alzheimer's disease
JP2001508798A (ja)	2001-07-03	ケモカインレセプター活性のモジュレーターとしての３，３−二置換ピペリジン類
SK286917B6 (sk)	2009-07-06	4-Substituované N-acylované deriváty piperidínu, farmaceutický prípravok s ich obsahom a ich použitie
JP2007508359A (ja)	2007-04-05	Ｎ−［ヘテロアリル（ピペリジン−２−イル）メチル］ベンズアミドの誘導体、この調製方法およびこの治療法における使用
JP2002532427A (ja)	2002-10-02	ケモカイン受容体活性のモジュレーターとしてのｎ−ウレイドアルキルピペリジン
CN103068800B (zh)	2014-10-29	作为趋化因子受体活性调节剂的哌啶基化合物
JP2002541104A (ja)	2002-12-03	ピロリジン系ケモカイン受容体活性調節剤
CN1037840C (zh)	1998-03-25	二苯甲基哌嗪衍生物的制备方法
NO174342B (no)	1994-01-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive aryloksyfenylpropylaminer
CA2123216A1 (en)	1993-06-10	Novel n-hydroxyalkyl-substituted 1,2,3,6-tetrahydropyridine and piperidine derivatives
MXPA05009290A (es)	2006-05-31	Derivados heterociclicos que contienen nitrogeno que tienen estirilo 2,6-disustituido.
NO881388L (no)	1988-10-03	Fremgangsmaate for fremstilling av 4-fenylpiperidinforbindelser.
EP0398326B1 (en)	1994-08-24	Serotonin antagonist
US4251655A (en)	1981-02-17	Substituted N-iminomethylpiperidines
CA2675450A1 (en)	2008-08-07	Soluble epoxide hydrolase inhibitors for treatment of metabolic syndrome and related disorders
WO1994029298A1 (en)	1994-12-22	8-amino-7-chloro-1,4-benzodioxan-5-carboxylic acid, -1-butyl-4-piperidinyl ester as a 5-ht4-receptor antagonist
JP2650847B2 (ja)	1997-09-10	心臓保護活性を有する薬理組成物
US3481935A (en)	1969-12-02	1-substituted-aminoloweralkyl-4-substituted-phenyl-piperidines
NO300843B1 (no)	1997-08-04	Aryliden-l-azacykloalkaner og arylalkyl-l-azacykloalkaner, salter av disse, og legemidler som inneholder disse forbindelser
DE69327077T2 (de)	2000-07-06	Carbamoylpyrrolidon-Derivate zur Behandlung von Depressionen und cerebrovasculären Störungen
IL103138A (en)	1999-05-09	History of traumatic acid process for their preparation and pharmaceutical preparations containing them
NO811212L (no)	1981-10-12	Fremgangsmaate ved fremstilling av antidepressive pyrrolypiperidiner.
AU668102C (en)	1997-05-15	5-HT4 receptor antagonists
US6365604B1 (en)	2002-04-02	Antipsychotic substituted piperidine derivatives