NO323402B1 - Nye forbindelser - Google Patents
Nye forbindelser Download PDFInfo
- Publication number
- NO323402B1 NO323402B1 NO20022918A NO20022918A NO323402B1 NO 323402 B1 NO323402 B1 NO 323402B1 NO 20022918 A NO20022918 A NO 20022918A NO 20022918 A NO20022918 A NO 20022918A NO 323402 B1 NO323402 B1 NO 323402B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- methyl
- quinolinyl
- piperazinyl
- dihydrochloride
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 230000036407 pain Effects 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- -1 CF 3 Chemical group 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 15
- 229940125782 compound 2 Drugs 0.000 claims description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229940125898 compound 5 Drugs 0.000 claims description 4
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229940126657 Compound 17 Drugs 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 208000020339 Spinal injury Diseases 0.000 claims description 3
- 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 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229940125773 compound 10 Drugs 0.000 claims description 3
- 229940125797 compound 12 Drugs 0.000 claims description 3
- 229940126543 compound 14 Drugs 0.000 claims description 3
- 229940125758 compound 15 Drugs 0.000 claims description 3
- 229940126142 compound 16 Drugs 0.000 claims description 3
- 229940125810 compound 20 Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 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 claims description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 3
- 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 claims description 2
- RJMXBLRLBQGVHA-UHFFFAOYSA-N 4-[[4-[[2,4-bis(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-quinolin-8-ylmethyl]-n,n-diethylbenzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC=2C(=CC(=CC=2)C(F)(F)F)C(F)(F)F)CC1 RJMXBLRLBQGVHA-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- UDSRUCAJZSIRHZ-UHFFFAOYSA-N benzamide dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=CC=C1.NC(=O)C1=CC=CC=C1 UDSRUCAJZSIRHZ-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 210000002820 sympathetic nervous system Anatomy 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- CWMISXRFUQVUGJ-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)-quinolin-8-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC=2C=CC=CC=2)CC1 CWMISXRFUQVUGJ-UHFFFAOYSA-N 0.000 claims 2
- CPYQOADCQMZDKM-UHFFFAOYSA-N 4-[[4-[(4-tert-butylphenyl)methyl]piperazin-1-yl]-quinolin-8-ylmethyl]-n,n-diethylbenzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC=2C=CC(=CC=2)C(C)(C)C)CC1 CPYQOADCQMZDKM-UHFFFAOYSA-N 0.000 claims 2
- TXYBLSGPPWJJES-UHFFFAOYSA-N n,n-diethyl-4-[[4-[(4-methylphenyl)methyl]piperazin-1-yl]-quinolin-8-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC=2C=CC(C)=CC=2)CC1 TXYBLSGPPWJJES-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- KDXQDSHCSIRJQE-UHFFFAOYSA-N n,n-diethyl-4-[quinolin-8-yl-[4-(thiophen-3-ylmethyl)piperazin-1-yl]methyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC2=CSC=C2)CC1 KDXQDSHCSIRJQE-UHFFFAOYSA-N 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 abstract description 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 2
- 125000004076 pyridyl group Chemical group 0.000 abstract description 2
- 125000001544 thienyl group Chemical group 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- 238000000034 method Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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- 229940125904 compound 1 Drugs 0.000 description 9
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- HSLVPASQEKTPAP-UHFFFAOYSA-N n,n-diethyl-4-[[4-[(4-nitrophenyl)methyl]piperazin-1-yl]-quinolin-8-ylmethyl]benzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C2=NC=CC=C2C=CC=1)N1CCN(CC=2C=CC(=CC=2)[N+]([O-])=O)CC1 HSLVPASQEKTPAP-UHFFFAOYSA-N 0.000 description 3
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- C07D211/58—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9904673A SE9904673D0 (sv) | 1999-12-20 | 1999-12-20 | Novel compounds |
PCT/SE2000/002559 WO2001045637A2 (en) | 1999-12-20 | 2000-12-15 | Novel 4(piperazinyl (8-quinolinyl)metyl)benzamides |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20022918D0 NO20022918D0 (no) | 2002-06-18 |
NO20022918L NO20022918L (no) | 2002-08-02 |
NO323402B1 true NO323402B1 (no) | 2007-04-23 |
Family
ID=20418209
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20022918A NO323402B1 (no) | 1999-12-20 | 2002-06-18 | Nye forbindelser |
Country Status (34)
Country | Link |
---|---|
US (1) | US6784181B2 (pt) |
EP (1) | EP1242402B1 (pt) |
JP (1) | JP2003518022A (pt) |
KR (1) | KR100807515B1 (pt) |
CN (1) | CN1225465C (pt) |
AT (1) | ATE254120T1 (pt) |
AU (1) | AU780714B2 (pt) |
BG (1) | BG65456B1 (pt) |
BR (1) | BR0016578A (pt) |
CA (1) | CA2393568C (pt) |
CO (1) | CO5271646A1 (pt) |
CZ (1) | CZ20022122A3 (pt) |
DE (1) | DE60006583T2 (pt) |
DK (1) | DK1242402T3 (pt) |
EE (1) | EE05035B1 (pt) |
ES (1) | ES2210028T3 (pt) |
HK (1) | HK1048113B (pt) |
HU (1) | HUP0300298A2 (pt) |
IL (2) | IL150126A0 (pt) |
IS (1) | IS2194B (pt) |
MX (1) | MXPA02006062A (pt) |
MY (1) | MY125394A (pt) |
NO (1) | NO323402B1 (pt) |
NZ (1) | NZ519985A (pt) |
PL (1) | PL356797A1 (pt) |
PT (1) | PT1242402E (pt) |
RU (1) | RU2260006C2 (pt) |
SE (1) | SE9904673D0 (pt) |
SK (1) | SK285753B6 (pt) |
TR (1) | TR200400237T4 (pt) |
TW (1) | TWI238822B (pt) |
UA (1) | UA72945C2 (pt) |
WO (1) | WO2001045637A2 (pt) |
ZA (1) | ZA200204256B (pt) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8987736B2 (en) * | 2000-07-10 | 2015-03-24 | Amit Goyal | [100] or [110] aligned, semiconductor-based, large-area, flexible, electronic devices |
SE0100764D0 (sv) | 2001-03-07 | 2001-03-07 | Astrazeneca Ab | New assymetric process |
DE60230869D1 (de) * | 2001-05-18 | 2009-03-05 | Astrazeneca Ab | 4-(phenylpiperazinylmethyl) benzamidderivate und deren verwendung zur behandlung von schmerzen, angst oder gastrointestinalen störungen |
JP4892654B2 (ja) * | 2001-10-29 | 2012-03-07 | マウント クック ファーマ,インコーポレーテッド | デルタレセプターアゴニスト化合物によるうつ病の治療方法 |
SE0203302D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203303D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0400027D0 (sv) * | 2004-01-09 | 2004-01-09 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
DK1781631T3 (da) * | 2004-08-02 | 2012-05-14 | Astrazeneca Ab | Diarylmethylpiperazinderivater, præparater dermed og anvendelser deraf |
SE0401968D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
WO2007137417A1 (en) * | 2006-05-26 | 2007-12-06 | Neuromed Pharmaceuticals Ltd. | Heterocyclic compounds as calcium channel blockers |
MY148880A (en) * | 2006-10-20 | 2013-06-14 | Astrazeneca Ab | N-(2-hydroxyethyl)-n-methyl-4-(quinolin-8-yl(1-(thiazol-4-ylmethyl)piperidin-4-ylidene)methyl)benzamide, the process of making it as well as its use for the treatment of pain, anxiety and depression |
EP2296657A4 (en) * | 2008-05-20 | 2011-12-14 | Astrazeneca Ab | METHOD FOR TREATING HEAVY DEPRESSION WITH FEARING STATES |
EP3725815B1 (en) * | 2017-12-12 | 2022-10-05 | Tokyo University of Science Foundation | Active energy ray-curable composition |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH585209A5 (pt) | 1973-06-29 | 1977-02-28 | Cermol Sa | |
DE2900810A1 (de) | 1979-01-11 | 1980-07-24 | Cassella Ag | Substituierte n-benzhydryl-n'-p- hydroxybenzyl-piperazine und verfahren zu ihrer herstellung |
IT1140978B (it) | 1980-05-23 | 1986-10-10 | Selvi & C Spa | 1-(4-clorobenzidril)-4-(2,3-diidros sipropil)-piperazina, metodi per la sua preparazione e relative composizione farmaceutiche |
GB8320701D0 (en) | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agent |
IT1196150B (it) | 1984-06-19 | 1988-11-10 | Poli Ind Chimica Spa | Derivati di 1-(bis-(4-fluorofenil)metil)-4-(3-fenil-2-propenil)-esaidro-1h-1,4-diazepina ad attivita' calcio antagonista,sua preparazione e composizioni che lo contengono |
SE8500573D0 (sv) | 1985-02-08 | 1985-02-08 | Ferrosan Ab | Novel piperazinecarboxamides having a phenoxyalkyl or thiophenoxyalkyl side chain |
US5028610A (en) | 1987-03-18 | 1991-07-02 | Sankyo Company Limited | N-benzhydryl-substituted heterocyclic derivatives, their preparation and their use |
US4829065A (en) | 1987-04-24 | 1989-05-09 | Syntex Pharmaceuticals, Ltd. | Substituted imidazolyl-alkyl-piperazine and -diazepine derivatives |
US4826844A (en) | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
RU2093156C1 (ru) | 1989-11-22 | 1997-10-20 | Жансен Фармасетика Н.В. | L-(-)-2-(аминокарбонил)-n-(4-амино-2,6-дихлорфенил-4[5,5-бис(4-фторфенил)пентил]-1-пиперазинацетамид, его фармацевтически приемлемая кислотно-аддитивная соль или гидрат, способ его получения и средство для хранения сердца донора |
US5681830A (en) | 1992-02-03 | 1997-10-28 | Delta Pharmaceuticals, Inc. | Opioid compounds |
GB9202238D0 (en) | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
US5807858A (en) | 1996-06-05 | 1998-09-15 | Delta Pharmaceutical, Inc. | Compositions and methods for reducing respiratory depression |
US5574159A (en) | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
FR2696744B1 (fr) | 1992-10-12 | 1994-12-30 | Logeais Labor Jacques | Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique. |
PT711289E (pt) | 1993-07-30 | 2001-02-28 | Delta Pharmaceuticals Inc | Compostos piperazina utilizados em terapia |
JP3352184B2 (ja) | 1993-11-12 | 2002-12-03 | 株式会社アズウェル | ピペラジン不飽和脂肪酸誘導体 |
SE9504661D0 (sv) | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
TW548271B (en) | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
AU2009799A (en) | 1997-12-24 | 1999-07-19 | Ortho-Mcneil Pharmaceutical, Inc. | 4-(aryl(piperidin-4-yl)) aminobenzamides which bind to the delta-opioid receptor |
-
1999
- 1999-12-20 SE SE9904673A patent/SE9904673D0/xx unknown
-
2000
- 2000-12-14 TW TW089126669A patent/TWI238822B/zh not_active IP Right Cessation
- 2000-12-15 WO PCT/SE2000/002559 patent/WO2001045637A2/en active IP Right Grant
- 2000-12-15 DK DK00989096T patent/DK1242402T3/da active
- 2000-12-15 PL PL00356797A patent/PL356797A1/xx not_active IP Right Cessation
- 2000-12-15 JP JP2001546378A patent/JP2003518022A/ja active Pending
- 2000-12-15 CA CA002393568A patent/CA2393568C/en not_active Expired - Fee Related
- 2000-12-15 CZ CZ20022122A patent/CZ20022122A3/cs unknown
- 2000-12-15 DE DE60006583T patent/DE60006583T2/de not_active Expired - Fee Related
- 2000-12-15 SK SK885-2002A patent/SK285753B6/sk not_active IP Right Cessation
- 2000-12-15 AT AT00989096T patent/ATE254120T1/de not_active IP Right Cessation
- 2000-12-15 US US10/149,911 patent/US6784181B2/en not_active Expired - Fee Related
- 2000-12-15 MX MXPA02006062A patent/MXPA02006062A/es active IP Right Grant
- 2000-12-15 AU AU25643/01A patent/AU780714B2/en not_active Ceased
- 2000-12-15 NZ NZ519985A patent/NZ519985A/en unknown
- 2000-12-15 EE EEP200200334A patent/EE05035B1/xx not_active IP Right Cessation
- 2000-12-15 HU HU0300298A patent/HUP0300298A2/hu unknown
- 2000-12-15 BR BR0016578-6A patent/BR0016578A/pt not_active Application Discontinuation
- 2000-12-15 TR TR2004/00237T patent/TR200400237T4/xx unknown
- 2000-12-15 KR KR1020027007835A patent/KR100807515B1/ko not_active IP Right Cessation
- 2000-12-15 PT PT00989096T patent/PT1242402E/pt unknown
- 2000-12-15 CN CNB008189765A patent/CN1225465C/zh not_active Expired - Fee Related
- 2000-12-15 UA UA2002064508A patent/UA72945C2/uk unknown
- 2000-12-15 EP EP00989096A patent/EP1242402B1/en not_active Expired - Lifetime
- 2000-12-15 ES ES00989096T patent/ES2210028T3/es not_active Expired - Lifetime
- 2000-12-15 IL IL15012600A patent/IL150126A0/xx active IP Right Grant
- 2000-12-15 RU RU2002114345/04A patent/RU2260006C2/ru not_active IP Right Cessation
- 2000-12-18 MY MYPI20005939A patent/MY125394A/en unknown
- 2000-12-19 CO CO00096314A patent/CO5271646A1/es not_active Application Discontinuation
-
2002
- 2002-05-28 ZA ZA200204256A patent/ZA200204256B/en unknown
- 2002-06-10 BG BG106806A patent/BG65456B1/bg unknown
- 2002-06-10 IL IL150126A patent/IL150126A/en not_active IP Right Cessation
- 2002-06-14 IS IS6423A patent/IS2194B/is unknown
- 2002-06-18 NO NO20022918A patent/NO323402B1/no not_active IP Right Cessation
-
2003
- 2003-01-07 HK HK03100181.6A patent/HK1048113B/zh not_active IP Right Cessation
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