ES2340441T3 - Compuestos de octahidrobencimidazolona como analgesicos. - Google Patents

Info

Publication number

ES2340441T3

ES2340441T3 ES08011371T ES08011371T ES2340441T3 ES 2340441 T3 ES2340441 T3 ES 2340441T3 ES 08011371 T ES08011371 T ES 08011371T ES 08011371 T ES08011371 T ES 08011371T ES 2340441 T3 ES2340441 T3 ES 2340441T3

Authority

ES

Spain

Prior art keywords

alkyl

cycloalkyl

quad

ring

halogen

Prior art date

2001-04-18

Legal status (The legal status 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 status listed.)

Expired - Lifetime

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 81
• 230000000202 analgesic effect Effects 0.000 title claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 203
• -1 - CH2OH Chemical group 0.000 claims abstract description 197
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 77
• 150000002367 halogens Chemical group 0.000 claims abstract description 68
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 62
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract description 52
• 239000001257 hydrogen Substances 0.000 claims abstract description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
• 125000001424 substituent group Chemical group 0.000 claims abstract description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 38
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 34
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
• 125000003118 aryl group Chemical group 0.000 claims abstract description 29
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 23
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 19
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 19
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims abstract description 18
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
• 125000005843 halogen group Chemical group 0.000 claims abstract description 13
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims abstract description 12
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
• 239000012453 solvate Substances 0.000 claims abstract description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 7
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims abstract description 7
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
• 150000001408 amides Chemical class 0.000 claims abstract description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
• 125000001475 halogen functional group Chemical group 0.000 claims abstract description 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 7
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 102000005962 receptors Human genes 0.000 claims description 22
• 108020003175 receptors Proteins 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 208000002193 Pain Diseases 0.000 claims description 11
• 108090000137 Opioid Receptors Proteins 0.000 claims description 9
• 102000003840 Opioid Receptors Human genes 0.000 claims description 9
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 230000036407 pain Effects 0.000 claims description 4
• 230000000144 pharmacologic effect Effects 0.000 claims description 4
• 230000004044 response Effects 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims 3
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 10
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 7
• 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 33
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• 239000003112 inhibitor Substances 0.000 description 22
• 239000003795 chemical substances by application Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000002552 dosage form Substances 0.000 description 13
• 238000000034 method Methods 0.000 description 13
• 239000000556 agonist Substances 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 150000002431 hydrogen Chemical group 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
• 239000005557 antagonist Substances 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 238000001914 filtration Methods 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• 150000003254 radicals Chemical class 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 229940083542 sodium Drugs 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000000730 antalgic agent Substances 0.000 description 6
• 125000006623 cyclooctylmethyl group Chemical group 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
• 108010020615 nociceptin receptor Proteins 0.000 description 6
• 235000015320 potassium carbonate Nutrition 0.000 description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 208000000094 Chronic Pain Diseases 0.000 description 5
• 239000001961 anticonvulsive agent Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 5
• 108090000765 processed proteins & peptides Proteins 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 229940124597 therapeutic agent Drugs 0.000 description 5
• 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 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 229940125681 anticonvulsant agent Drugs 0.000 description 4
• 239000000935 antidepressant agent Substances 0.000 description 4
• 229940005513 antidepressants Drugs 0.000 description 4
• 239000002246 antineoplastic agent Substances 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
• 238000013270 controlled release Methods 0.000 description 4
• XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 125000005842 heteroatom Chemical group 0.000 description 4
• OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
• 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 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 125000001624 naphthyl group Chemical group 0.000 description 4
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 4
• 125000004434 sulfur atom Chemical group 0.000 description 4
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 239000007995 HEPES buffer Substances 0.000 description 3
• 108010050904 Interferons Proteins 0.000 description 3
• 102000014150 Interferons Human genes 0.000 description 3
• 108010000817 Leuprolide Proteins 0.000 description 3
• OTKJDMGTUTTYMP-ROUUACIJSA-N Safingol ( L-threo-sphinganine) Chemical compound CCCCCCCCCCCCCCC[C@H](O)[C@@H](N)CO OTKJDMGTUTTYMP-ROUUACIJSA-N 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• QPWBZVAOCWJTFK-UHFFFAOYSA-L [2-(azanidylmethyl)-3-hydroxy-2-(hydroxymethyl)propyl]azanide;cyclobutane-1,1-dicarboxylate;platinum(4+) Chemical group [Pt+4].[NH-]CC(C[NH-])(CO)CO.[O-]C(=O)C1(C([O-])=O)CCC1 QPWBZVAOCWJTFK-UHFFFAOYSA-L 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 229940035676 analgesics Drugs 0.000 description 3
• 229940125683 antiemetic agent Drugs 0.000 description 3
• 239000002111 antiemetic agent Substances 0.000 description 3
• 239000002221 antipyretic Substances 0.000 description 3
• 239000012148 binding buffer Substances 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• UKTAZPQNNNJVKR-KJGYPYNMSA-N chembl2368925 Chemical compound C1=CC=C2C(C(O[C@@H]3C[C@@H]4C[C@H]5C[C@@H](N4CC5=O)C3)=O)=CNC2=C1 UKTAZPQNNNJVKR-KJGYPYNMSA-N 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 229960003413 dolasetron Drugs 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 239000006274 endogenous ligand Substances 0.000 description 3
• UJYGDMFEEDNVBF-UHFFFAOYSA-N ergocornin Chemical compound C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 3
• 235000019439 ethyl acetate Nutrition 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 3
• GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 3
• 229960004338 leuprorelin Drugs 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 229910001629 magnesium chloride Inorganic materials 0.000 description 3
• 229960005181 morphine Drugs 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 229940121367 non-opioid analgesics Drugs 0.000 description 3
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
• 239000006186 oral dosage form Substances 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
• 229950006050 spiromustine Drugs 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
• XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 3
• HZSBSRAVNBUZRA-RQDPQJJXSA-J (1r,2r)-cyclohexane-1,2-diamine;tetrachloroplatinum(2+) Chemical compound Cl[Pt+2](Cl)(Cl)Cl.N[C@@H]1CCCC[C@H]1N HZSBSRAVNBUZRA-RQDPQJJXSA-J 0.000 description 2
• FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 2
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 2
• TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 2
• BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
• FONKWHRXTPJODV-DNQXCXABSA-N 1,3-bis[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]urea Chemical compound C1([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C4=CC(O)=C5NC=C(C5=C4[C@H](CCl)C3)C)=C2C=C(O)C2=C1C(C)=CN2 FONKWHRXTPJODV-DNQXCXABSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• QNKJFXARIMSDBR-UHFFFAOYSA-N 3-[2-[bis(2-chloroethyl)amino]ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound O=C1N(CCN(CCCl)CCCl)C(=O)NC11CCCCC1 QNKJFXARIMSDBR-UHFFFAOYSA-N 0.000 description 2
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