ITMI992711A1 - Composti organici - Google Patents

Info

Publication number

ITMI992711A1

ITMI992711A1 IT1999MI002711A ITMI992711A ITMI992711A1 IT MI992711 A1 ITMI992711 A1 IT MI992711A1 IT 1999MI002711 A IT1999MI002711 A IT 1999MI002711A IT MI992711 A ITMI992711 A IT MI992711A IT MI992711 A1 ITMI992711 A1 IT MI992711A1

Authority

IT

Italy

Prior art keywords

group

alkyl

receptor

amino

abl

Prior art date

1999-12-27

Links

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• 150000002894 organic compounds Chemical class 0.000 title claims description 35
• -1 lower-alkoxycarbonyl Chemical group 0.000 claims description 107
• 150000001875 compounds Chemical class 0.000 claims description 86
• 238000011282 treatment Methods 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 70
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
• 201000010099 disease Diseases 0.000 claims description 63
• 108091008606 PDGF receptors Proteins 0.000 claims description 59
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 58
• 230000027455 binding Effects 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 48
• 239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 239000002253 acid Substances 0.000 claims description 40
• 230000002062 proliferating effect Effects 0.000 claims description 40
• 150000003254 radicals Chemical class 0.000 claims description 35
• 229960003276 erythromycin Drugs 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 239000000203 mixture Substances 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 102000003886 Glycoproteins Human genes 0.000 claims description 22
• 108090000288 Glycoproteins Proteins 0.000 claims description 22
• 239000000126 substance Substances 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical group 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 239000003112 inhibitor Substances 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 18
• 125000003277 amino group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 108091000080 Phosphotransferase Proteins 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 102000020233 phosphotransferase Human genes 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
• 102000005962 receptors Human genes 0.000 claims description 11
• 108020003175 receptors Proteins 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 8
• HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 claims description 8
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229950010883 phencyclidine Drugs 0.000 claims description 8
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 8
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 8
• HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 claims description 8
• PBCZSGKMGDDXIJ-UHFFFAOYSA-N 7beta-hydroxystaurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3C(O)NC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 PBCZSGKMGDDXIJ-UHFFFAOYSA-N 0.000 claims description 7
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 6
• 230000001028 anti-proliverative effect Effects 0.000 claims description 6
• 229960003914 desipramine Drugs 0.000 claims description 6
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 6
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 6
• 239000003242 anti bacterial agent Substances 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 239000002207 metabolite Substances 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 4
• AZFZKANGXPSDEA-NVNXTCNLSA-N (z)-3-(4-bromophenyl)-n-methyl-3-pyridin-3-ylprop-2-en-1-amine Chemical compound C=1C=CN=CC=1C(=C/CNC)\C1=CC=C(Br)C=C1 AZFZKANGXPSDEA-NVNXTCNLSA-N 0.000 claims description 4
• LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 claims description 4
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 4
• FHIKZROVIDCMJA-UHFFFAOYSA-N 2-(2,2-diphenylpentanoyloxy)ethyl-diethylazanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)OCCN(CC)CC)(CCC)C1=CC=CC=C1 FHIKZROVIDCMJA-UHFFFAOYSA-N 0.000 claims description 4
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 4
• USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 4
• 235000001258 Cinchona calisaya Nutrition 0.000 claims description 4
• VTUSIVBDOCDNHS-UHFFFAOYSA-N Etidocaine Chemical compound CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C VTUSIVBDOCDNHS-UHFFFAOYSA-N 0.000 claims description 4
• JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 claims description 4
• YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 claims description 4
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 4
• XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 4
• JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 claims description 4
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 4
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
• MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 4
• GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 claims description 4
• HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 229960002213 alprenolol Drugs 0.000 claims description 4
• PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 4
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims description 4
• 229960001220 amsacrine Drugs 0.000 claims description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 229960004957 aprindine Drugs 0.000 claims description 4
• NZLBHDRPUJLHCE-UHFFFAOYSA-N aprindine Chemical compound C1C2=CC=CC=C2CC1N(CCCN(CC)CC)C1=CC=CC=C1 NZLBHDRPUJLHCE-UHFFFAOYSA-N 0.000 claims description 4
• JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 claims description 4
• WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 claims description 4
• 229960001671 azapropazone Drugs 0.000 claims description 4
• UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 claims description 4
• 229960003665 bepridil Drugs 0.000 claims description 4
• 230000003115 biocidal effect Effects 0.000 claims description 4
• YSXKPIUOCJLQIE-UHFFFAOYSA-N biperiden Chemical compound C1C(C=C2)CC2C1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 YSXKPIUOCJLQIE-UHFFFAOYSA-N 0.000 claims description 4
• 229960003003 biperiden Drugs 0.000 claims description 4
• 229960003150 bupivacaine Drugs 0.000 claims description 4
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims description 4
• 229960001058 bupropion Drugs 0.000 claims description 4
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 4
• 229960000623 carbamazepine Drugs 0.000 claims description 4
• 229960004782 chlordiazepoxide Drugs 0.000 claims description 4
• ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 claims description 4
• VKQDZNZTPGLGFD-UHFFFAOYSA-N ciclazindol Chemical compound C12=NCCCN2C2=CC=CC=C2C1(O)C1=CC=CC(Cl)=C1 VKQDZNZTPGLGFD-UHFFFAOYSA-N 0.000 claims description 4
• 229950009468 ciclazindol Drugs 0.000 claims description 4
• 229960000520 diphenhydramine Drugs 0.000 claims description 4
• UVTNFZQICZKOEM-UHFFFAOYSA-N disopyramide Chemical compound C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 UVTNFZQICZKOEM-UHFFFAOYSA-N 0.000 claims description 4
• 229960001066 disopyramide Drugs 0.000 claims description 4
• RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 claims description 4
• 229960001389 doxazosin Drugs 0.000 claims description 4
• 229960005309 estradiol Drugs 0.000 claims description 4
• 229930182833 estradiol Natural products 0.000 claims description 4
• 229960003976 etidocaine Drugs 0.000 claims description 4
• 229960002428 fentanyl Drugs 0.000 claims description 4
• 229960002972 glutethimide Drugs 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 229960003299 ketamine Drugs 0.000 claims description 4
• 229960004194 lidocaine Drugs 0.000 claims description 4
• 229950010274 lofentanil Drugs 0.000 claims description 4
• IMYHGORQCPYVBZ-NLFFAJNJSA-N lofentanil Chemical compound CCC(=O)N([C@@]1([C@@H](CN(CCC=2C=CC=CC=2)CC1)C)C(=O)OC)C1=CC=CC=C1 IMYHGORQCPYVBZ-NLFFAJNJSA-N 0.000 claims description 4
• 229960001074 lorcainide Drugs 0.000 claims description 4
• XHOJAWVAWFHGHL-UHFFFAOYSA-N lorcainide Chemical compound C1CN(C(C)C)CCC1N(C=1C=CC(Cl)=CC=1)C(=O)CC1=CC=CC=C1 XHOJAWVAWFHGHL-UHFFFAOYSA-N 0.000 claims description 4
• 229960000423 loxapine Drugs 0.000 claims description 4
• XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims description 4
• 229960001797 methadone Drugs 0.000 claims description 4
• 229960002803 methaqualone Drugs 0.000 claims description 4
• TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 4
• 229960004503 metoclopramide Drugs 0.000 claims description 4
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 4
• 229960002237 metoprolol Drugs 0.000 claims description 4
• 229960003955 mianserin Drugs 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 229950000663 moxaprindine Drugs 0.000 claims description 4
• QQGGXAOUSKREAE-UHFFFAOYSA-N n,n-diethyl-n'-(1-methoxy-2,3-dihydro-1h-inden-2-yl)-n'-phenylpropane-1,3-diamine Chemical compound C1C2=CC=CC=C2C(OC)C1N(CCCN(CC)CC)C1=CC=CC=C1 QQGGXAOUSKREAE-UHFFFAOYSA-N 0.000 claims description 4
• XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 229960002009 naproxen Drugs 0.000 claims description 4
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 4
• 229960001073 nomifensine Drugs 0.000 claims description 4
• XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 claims description 4
• 229960000482 pethidine Drugs 0.000 claims description 4
• 229960002895 phenylbutazone Drugs 0.000 claims description 4
• VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 4
• 229960002508 pindolol Drugs 0.000 claims description 4
• PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 4
• 229960001289 prazosin Drugs 0.000 claims description 4
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 4
• 229960005205 prednisolone Drugs 0.000 claims description 4
• 229960003387 progesterone Drugs 0.000 claims description 4
• 239000000186 progesterone Substances 0.000 claims description 4
• 229960003712 propranolol Drugs 0.000 claims description 4
• 229960000957 prothipendyl Drugs 0.000 claims description 4
• JTTAUPUMOLRVRA-UHFFFAOYSA-N prothipendyl Chemical group C1=CN=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 JTTAUPUMOLRVRA-UHFFFAOYSA-N 0.000 claims description 4
• 229960002601 protriptyline Drugs 0.000 claims description 4
• BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 claims description 4
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