ES2316559T3 - Compuestos espiroindeno y espiroindano. - Google Patents
Compuestos espiroindeno y espiroindano. Download PDFInfo
- Publication number
- ES2316559T3 ES2316559T3 ES02725733T ES02725733T ES2316559T3 ES 2316559 T3 ES2316559 T3 ES 2316559T3 ES 02725733 T ES02725733 T ES 02725733T ES 02725733 T ES02725733 T ES 02725733T ES 2316559 T3 ES2316559 T3 ES 2316559T3
- Authority
- ES
- Spain
- Prior art keywords
- spiro
- quad
- piperidine
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- compound according
- Prior art date
- 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 91
- -1 phenyloxy Chemical group 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 108010020615 nociceptin receptor Proteins 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 10
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 9
- 108090000137 Opioid Receptors Proteins 0.000 claims description 9
- 102000003840 Opioid Receptors Human genes 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000000144 pharmacologic effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- RNXPWRGCFBJEBC-UHFFFAOYSA-N 1'-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC2=CC=CC=C2C1(CC1)CCN1C1CC2CCCCC2CC1 RNXPWRGCFBJEBC-UHFFFAOYSA-N 0.000 claims description 3
- XQYSCVDRMWSQEL-UHFFFAOYSA-N 1'-(2,3-dihydro-1h-inden-2-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC11CCN(C2CC3=CC=CC=C3C2)CC1 XQYSCVDRMWSQEL-UHFFFAOYSA-N 0.000 claims description 3
- MPDHINFVEFHYFB-UHFFFAOYSA-N 1'-(2,3-dihydro-1h-inden-2-yl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC2=CC=CC=C2C1(CC1)CCN1C1CC2=CC=CC=C2C1 MPDHINFVEFHYFB-UHFFFAOYSA-N 0.000 claims description 3
- JUYHQLDPNTVZBQ-UHFFFAOYSA-N 1'-(3-bicyclo[2.2.1]heptanyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2=CC=CC=C2C1(CC1)CCN1C1CC2CC1CC2 JUYHQLDPNTVZBQ-UHFFFAOYSA-N 0.000 claims description 3
- YMFHWBXASJRUMY-UHFFFAOYSA-N 1'-(4-propan-2-ylcyclohexyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC(C(C)C)CCC1N1CCC2(C3=CC=CC=C3CC2)CC1 YMFHWBXASJRUMY-UHFFFAOYSA-N 0.000 claims description 3
- KRPSXNNVCBQCEC-UHFFFAOYSA-N 1'-(4-propylcyclohexyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC(CCC)CCC1N1CCC2(C3=CC=CC=C3CC2)CC1 KRPSXNNVCBQCEC-UHFFFAOYSA-N 0.000 claims description 3
- HVSPQHTVYBVQHM-UHFFFAOYSA-N 1'-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)spiro[indene-1,4'-piperidine] Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2C1N1CCC2(C3=CC=CC=C3C=C2)CC1 HVSPQHTVYBVQHM-UHFFFAOYSA-N 0.000 claims description 3
- AANJKKDEXNNEKD-UHFFFAOYSA-N 1'-[(4-phenylmethoxyphenyl)methyl]spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C=1C=C(CN2CCC3(C4=CC=CC=C4CC3)CC2)C=CC=1OCC1=CC=CC=C1 AANJKKDEXNNEKD-UHFFFAOYSA-N 0.000 claims description 3
- OQPGVLZDVOZJLJ-UHFFFAOYSA-N 1'-cyclodecylspiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1C1CCCCCCCCC1 OQPGVLZDVOZJLJ-UHFFFAOYSA-N 0.000 claims description 3
- URGFMBOYZAXORX-UHFFFAOYSA-N 1'-cyclooctylspiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1C1CCCCCCC1 URGFMBOYZAXORX-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- PNULDNFMKQSJDK-UHFFFAOYSA-N 1'-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC11CCN(C2CC3CCCCC3CC2)CC1 PNULDNFMKQSJDK-UHFFFAOYSA-N 0.000 claims description 2
- MWRSALXQUKNUKD-UHFFFAOYSA-N 1'-[(4-phenylmethoxyphenyl)methyl]spiro[indene-1,4'-piperidine] Chemical compound C=1C=C(CN2CCC3(CC2)C2=CC=CC=C2C=C3)C=CC=1OCC1=CC=CC=C1 MWRSALXQUKNUKD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 240000007313 Tilia cordata Species 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 27
- 239000003112 inhibitor Substances 0.000 description 24
- 102000005962 receptors Human genes 0.000 description 21
- 108020003175 receptors Proteins 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000005557 antagonist Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000000556 agonist Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 125000004429 atom Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229940083542 sodium Drugs 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000730 antalgic agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 229940035676 analgesics Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001914 filtration Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- YSSBJODGIYRAMI-UHFFFAOYSA-N vesamicol Chemical class OC1CCCCC1N1CCC(C=2C=CC=CC=2)CC1 YSSBJODGIYRAMI-UHFFFAOYSA-N 0.000 description 6
- 108010050904 Interferons Proteins 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 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 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000003342 alkenyl group Chemical group 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
- 239000012148 binding buffer Substances 0.000 description 4
- 210000004027 cell Anatomy 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
- 238000004440 column chromatography 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
- 235000019439 ethyl acetate Nutrition 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
- 229940079322 interferon Drugs 0.000 description 4
- 229940127240 opiate Drugs 0.000 description 4
- 239000006186 oral dosage form Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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
- 239000007995 HEPES buffer Substances 0.000 description 3
- 108010000817 Leuprolide Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 229910019142 PO4 Inorganic materials 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
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 3
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
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- Psychiatry (AREA)
- Pulmonology (AREA)
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- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
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- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28467001P | 2001-04-18 | 2001-04-18 | |
| US284670P | 2001-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2316559T3 true ES2316559T3 (es) | 2009-04-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02725733T Expired - Lifetime ES2316559T3 (es) | 2001-04-18 | 2002-04-18 | Compuestos espiroindeno y espiroindano. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6828440B2 (enExample) |
| EP (2) | EP1385514B9 (enExample) |
| JP (1) | JP4489354B2 (enExample) |
| AT (1) | ATE413175T1 (enExample) |
| AU (1) | AU2002256282C1 (enExample) |
| CA (1) | CA2443938C (enExample) |
| CY (1) | CY1108731T1 (enExample) |
| DE (1) | DE60229736D1 (enExample) |
| DK (1) | DK1385514T5 (enExample) |
| ES (1) | ES2316559T3 (enExample) |
| PT (1) | PT1385514E (enExample) |
| SI (1) | SI1385514T1 (enExample) |
| WO (1) | WO2002085354A1 (enExample) |
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| US6374762B1 (en) * | 1997-10-27 | 2002-04-23 | Correct Craft, Inc. | Water sport towing apparatus |
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| US7566728B2 (en) | 2002-03-29 | 2009-07-28 | Mitsubishi Tanabe Pharma Corporation | Remedy for sleep disturbance |
| EP1613601A4 (en) | 2003-04-04 | 2007-05-02 | Merck & Co Inc | ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS |
| GB0328906D0 (en) * | 2003-12-12 | 2004-01-14 | Syngenta Participations Ag | Chemical compounds |
| US20100009929A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and bortezomib and derivatives thereof and methods of use thereof |
| US8435959B2 (en) | 2004-03-29 | 2013-05-07 | University Of South Florida | Effective treatment of tumors and cancer with triciribine and related compounds |
| US20100028339A1 (en) | 2004-03-29 | 2010-02-04 | Cheng Jin Q | Compositions including triciribine and trastuzumab and methods of use thereof |
| US20110008327A1 (en) | 2004-03-29 | 2011-01-13 | Cheng Jin Q | Compositions including triciribine and epidermal growth factor receptor inhibitor compounds or salts thereof and methods of use thereof |
| US20100173864A1 (en) | 2004-03-29 | 2010-07-08 | Cheng Jin Q | Compositions including triciribine and one or more platinum compounds and methods of use thereof |
| US20100009928A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and taxanes and methods of use thereof |
| US7354925B2 (en) * | 2004-03-29 | 2008-04-08 | Pfizer Inc. | Alpha aryl or heteroaryl methyl beta piperidino propanamide compounds as ORL1-receptor antagonists |
| JP2008510728A (ja) * | 2004-08-19 | 2008-04-10 | バーテックス ファーマシューティカルズ インコーポレイテッド | ムスカリン受容体のモジュレーター |
| US7786141B2 (en) * | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| US7863449B2 (en) * | 2004-11-29 | 2011-01-04 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| US8193208B2 (en) * | 2005-09-09 | 2012-06-05 | Purdue Pharma L.P. | Fused and spirocycle compounds and the use thereof |
| CN1870631B (zh) * | 2005-11-11 | 2010-04-14 | 华为技术有限公司 | 媒体网关的门控方法 |
| CA2634456A1 (en) * | 2005-12-22 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| WO2007100664A2 (en) | 2006-02-22 | 2007-09-07 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| RU2008137583A (ru) * | 2006-02-22 | 2010-03-27 | Вертекс Фармасьютикалз Инкорпорейшн (Us) | Спиропиперидины в качестве модуляторов мускариновых рецепторов |
| CA2656183A1 (en) * | 2006-06-29 | 2008-01-10 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| AU2007284548A1 (en) | 2006-08-15 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| US7786107B2 (en) * | 2006-08-18 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| AU2008291823B2 (en) | 2007-08-31 | 2012-02-23 | Purdue Pharma L.P. | Substituted-quinoxaline-type-piperidine compounds and the uses thereof |
| AU2008307440A1 (en) * | 2007-10-03 | 2009-04-09 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| EP2265588B1 (en) * | 2008-02-27 | 2013-06-26 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF 11ß -HYDROXYSTEROID DEHYDROGENASE TYPE 1 |
| RU2500678C2 (ru) | 2008-07-21 | 2013-12-10 | Пэдью Фарма Л.П. | Замещенные хиноксалинового типа мостиковые пиперидиновые соединения и их применение |
| US8431700B2 (en) * | 2009-03-03 | 2013-04-30 | Vanderbilt University | Alkylsulfonyl-2,3-dihydrospiro[indene-1,4′-piperidine] analogs as GlyT1 inhibitors, methods for making same, and use of same in treating psychiatric disorders |
| AR078522A1 (es) * | 2009-10-15 | 2011-11-16 | Lilly Co Eli | Compuesto de espiropiperidina, composicion farmaceutica que lo comprende, su uso para preparar un medicamento util para tratar diabetes y compuesto intermediario para su sintesis |
| US10118927B2 (en) | 2012-12-27 | 2018-11-06 | Purdue Pharma L.P. | Substituted piperidin-4-amino-type compounds and uses thereof |
| US9963458B2 (en) | 2012-12-27 | 2018-05-08 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| WO2014102594A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| US9951038B2 (en) | 2012-12-27 | 2018-04-24 | Purdue Pharma L.P. | Quinazolin-4(3H)-one-type piperidine compounds and uses thereof |
| CN109640991A (zh) | 2016-07-29 | 2019-04-16 | 詹森药业有限公司 | 治疗前列腺癌的方法 |
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| FR1335831A (fr) * | 1962-10-09 | 1963-08-23 | Res Lab Dr C Janssen Nv | Procédé de préparation de nu-(3, 3-diphényl-3-alcanoyl)-propylspiro |
| US3161645A (en) | 1962-12-18 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds |
| US3318900A (en) | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| US3325499A (en) | 1964-11-02 | 1967-06-13 | Mcneilab Inc | 1-(1-hydrocarbyl-4-piperdyl)-2-indolinone |
| US3666764A (en) * | 1970-08-26 | 1972-05-30 | Mead Johnson & Co | Spiroindenylpiperidines |
| DE2609645A1 (de) | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| US4329353A (en) | 1980-10-22 | 1982-05-11 | Janssen Pharmaceutica, N.V. | 1-(4-Aryl-cyclohexyl)piperidine derivatives, method of use thereof and pharmaceutical compositions thereof |
| US4410528A (en) | 1980-05-16 | 1983-10-18 | Kyowa Hakko Kogyo Co., Ltd. | Hypotensive piperidine derivatives |
| JPS58180481A (ja) | 1982-04-15 | 1983-10-21 | Kyowa Hakko Kogyo Co Ltd | 新規なピペリジン誘導体 |
| JPS60120872A (ja) | 1983-12-01 | 1985-06-28 | Kyowa Hakko Kogyo Co Ltd | 新規なヘテロ環状化合物及び強心剤 |
| EP0445974A3 (en) * | 1990-03-05 | 1992-04-29 | Merck Sharp & Dohme Ltd. | Spirocyclic antipsychotic agents |
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| DE69412067T2 (de) | 1993-01-28 | 1999-03-25 | Merck & Co., Inc., Rahway, N.J. | Substituierte spiro-azaringen als tachykinine rezeptor antagonisten |
| US5457207A (en) * | 1993-10-05 | 1995-10-10 | Regents Of The University Of Minnesota | Spirovesamicols |
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| CA2187767A1 (en) | 1994-04-14 | 1995-10-26 | Joel R. Huff | Alpha1c adrenergic receptor antagonists |
| FR2722190B1 (fr) | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
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| JP3342478B2 (ja) | 1998-01-19 | 2002-11-11 | ファイザー製薬株式会社 | Ｏｒｌ１−レセプターアゴニストとしての４−（２−ケト−１−ベンズイミダゾリニル）ピペリジン化合物 |
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| MA26659A1 (fr) | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| JP2001011050A (ja) * | 1999-04-30 | 2001-01-16 | Sankyo Co Ltd | 含窒素飽和複素環化合物 |
| WO2001022919A2 (en) | 1999-09-30 | 2001-04-05 | Merck & Co., Inc. | Spiro[bicyclic -azacycloalkyl and -cycloalkyl] derivatives and uses thereof |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
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| WO2002026714A1 (en) * | 2000-09-27 | 2002-04-04 | Takeda Chemical Industries, Ltd. | Spiro compounds |
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2002
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- 2002-04-18 DK DK02725733T patent/DK1385514T5/da active
- 2002-04-18 PT PT02725733T patent/PT1385514E/pt unknown
- 2002-04-18 CA CA2443938A patent/CA2443938C/en not_active Expired - Fee Related
- 2002-04-18 WO PCT/US2002/012357 patent/WO2002085354A1/en not_active Ceased
- 2002-04-18 AU AU2002256282A patent/AU2002256282C1/en not_active Ceased
- 2002-04-18 JP JP2002582927A patent/JP4489354B2/ja not_active Expired - Fee Related
- 2002-04-18 EP EP02725733A patent/EP1385514B9/en not_active Expired - Lifetime
- 2002-04-18 DE DE60229736T patent/DE60229736D1/de not_active Expired - Lifetime
- 2002-04-18 AT AT02725733T patent/ATE413175T1/de active
- 2002-04-18 EP EP08168203A patent/EP2033644A1/en not_active Withdrawn
- 2002-04-18 ES ES02725733T patent/ES2316559T3/es not_active Expired - Lifetime
- 2002-04-18 SI SI200230789T patent/SI1385514T1/sl unknown
-
2009
- 2009-01-27 CY CY20091100103T patent/CY1108731T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20030018041A1 (en) | 2003-01-23 |
| EP2033644A1 (en) | 2009-03-11 |
| CY1108731T1 (el) | 2014-04-09 |
| EP1385514B9 (en) | 2009-08-12 |
| WO2002085354A1 (en) | 2002-10-31 |
| SI1385514T1 (sl) | 2009-04-30 |
| ATE413175T1 (de) | 2008-11-15 |
| AU2002256282C1 (en) | 2006-08-17 |
| AU2002256282B2 (en) | 2005-08-11 |
| EP1385514A1 (en) | 2004-02-04 |
| DE60229736D1 (de) | 2008-12-18 |
| CA2443938A1 (en) | 2002-10-31 |
| JP2004532223A (ja) | 2004-10-21 |
| US6828440B2 (en) | 2004-12-07 |
| CA2443938C (en) | 2010-06-22 |
| JP4489354B2 (ja) | 2010-06-23 |
| PT1385514E (pt) | 2009-02-04 |
| DK1385514T5 (da) | 2009-03-09 |
| DK1385514T3 (da) | 2009-01-19 |
| EP1385514A4 (en) | 2005-04-13 |
| EP1385514B1 (en) | 2008-11-05 |
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