CA2245578A1 - Derives de spirochetes et leur utilisation en tant qu'agents therapeutiques - Google Patents
Derives de spirochetes et leur utilisation en tant qu'agents therapeutiques Download PDFInfo
- Publication number
- CA2245578A1 CA2245578A1 CA 2245578 CA2245578A CA2245578A1 CA 2245578 A1 CA2245578 A1 CA 2245578A1 CA 2245578 CA2245578 CA 2245578 CA 2245578 A CA2245578 A CA 2245578A CA 2245578 A1 CA2245578 A1 CA 2245578A1
- Authority
- CA
- Canada
- Prior art keywords
- dioxa
- aza
- decane
- fluorophenyl
- spiro
- 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.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims description 16
- 229940124597 therapeutic agent Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 242
- -1 phenoxy, benzyloxy Chemical group 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical class 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 28
- 208000002193 Pain Diseases 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 230000002265 prevention Effects 0.000 claims abstract description 18
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- 206010027599 migraine Diseases 0.000 claims abstract description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 8
- 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 5
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 13
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- 238000000034 method Methods 0.000 claims description 71
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- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 claims description 28
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
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- 125000006413 ring segment Chemical group 0.000 claims description 9
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- 150000001412 amines Chemical class 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
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- 239000011737 fluorine Substances 0.000 claims description 8
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
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- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 claims description 4
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 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 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 13
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 84
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- 239000000243 solution Substances 0.000 description 46
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- 239000003921 oil Substances 0.000 description 41
- 235000019198 oils Nutrition 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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- 238000010626 work up procedure Methods 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention se rapporte à des composés représentés par la formule (I) dans laquelle R est hydroxy, alcoxy C¿1-6?, alcényloxy C¿3-6?, alcynyloxy C¿3-6?, fluoro alcoxy C¿1-6?, cycloalcoxy C¿3-7?, cycloalkyle C¿3-7? alcoxy C¿1-4?, phénoxy, benzyloxy ou halogène, la fraction phényle dudit phénoxy ou dudit benzyloxy étant éventuellement substituée par un, deux ou trois composés sélectionnés parmi un alkyle C¿1-6?, un alcoxy C¿1-6?, un halogène et un trifluorométhyle, R?1¿, R?2¿, R?3¿, R?4¿, R?5¿, R?6¿, R?9a¿ et R?9b¿ sont tels que définis dans le descriptif de l'invention, ou bien R et R?1¿ peuvent être liés de façon à ce que -R-R?1¿- soit une liaison sélectionnée parmi -O-CH¿2?- et -O-CH¿2?CH¿2?-, m est égal à 0, 1, 2 ou 3 et n est égal à 0, 1, 2 ou 3 à condition que la somme de m et n soit égale à 2 ou 3. L'invention se rapporte également à des sels pharmaceutiquement acceptables de ces composés. Lesdits composés sont particulièrement utiles au traitement ou à la prévention de la douleur, de l'inflammation, de la migraine, des vomissements et de la névralgie postherpétique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9603136.4A GB9603136D0 (en) | 1996-02-15 | 1996-02-15 | Therapeutic agents |
| GB9603136.4 | 1996-02-15 | ||
| PCT/GB1997/000404 WO1997030056A1 (fr) | 1996-02-15 | 1997-02-13 | Derives de spirochetes et leur utilisation en tant qu'agents therapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2245578A1 true CA2245578A1 (fr) | 1997-08-21 |
Family
ID=29422170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2245578 Abandoned CA2245578A1 (fr) | 1996-02-15 | 1997-02-13 | Derives de spirochetes et leur utilisation en tant qu'agents therapeutiques |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2245578A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115969834A (zh) * | 2023-01-06 | 2023-04-18 | 西北大学 | 一种螺环缩酮类化合物在制备抗肿瘤药物中的应用 |
-
1997
- 1997-02-13 CA CA 2245578 patent/CA2245578A1/fr not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115969834A (zh) * | 2023-01-06 | 2023-04-18 | 西北大学 | 一种螺环缩酮类化合物在制备抗肿瘤药物中的应用 |
| CN115969834B (zh) * | 2023-01-06 | 2024-08-13 | 西北大学 | 一种螺环缩酮类化合物在制备抗肿瘤药物中的应用 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |