CA2174731C - Derives de rapamycine utilises comme immonosuppresseurs - Google Patents
Derives de rapamycine utilises comme immonosuppresseurs Download PDFInfo
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- CA2174731C CA2174731C CA002174731A CA2174731A CA2174731C CA 2174731 C CA2174731 C CA 2174731C CA 002174731 A CA002174731 A CA 002174731A CA 2174731 A CA2174731 A CA 2174731A CA 2174731 C CA2174731 C CA 2174731C
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- Prior art keywords
- rapamycin
- formula
- iii
- alkyl
- compound according
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- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical class C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 title abstract description 41
- 229960003444 immunosuppressant agent Drugs 0.000 title abstract description 9
- 239000003018 immunosuppressive agent Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 83
- 229960002930 sirolimus Drugs 0.000 claims description 57
- -1 alkyenyl Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 230000001506 immunosuppresive effect Effects 0.000 claims description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 9
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 210000000056 organ Anatomy 0.000 claims description 9
- 125000004001 thioalkyl group Chemical group 0.000 claims description 9
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 8
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- 230000036457 multidrug resistance Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
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- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
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- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
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- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 3
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- ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 claims 1
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- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 31
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- 239000000243 solution Substances 0.000 description 16
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
L'invention concerne des nouveaux dérivés déméthoxy de la rapamycine de formule (I) utiles dans le domaine pharmaceutique, en particulier en tant qu'immunosuppresseurs. Dans cette formule (I), R¿2? est représenté par la formule (II) ou (III). Dans les formules (I), (II) et (III), X, Y, R¿1?, R¿3?, R¿4?, R¿5? sont tels que définis dans la demande.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9325800.2 | 1993-12-17 | ||
| GB9325802.8 | 1993-12-17 | ||
| GB939325800A GB9325800D0 (en) | 1993-12-17 | 1993-12-17 | Organic compounds |
| GB939325802A GB9325802D0 (en) | 1993-12-17 | 1993-12-17 | Organic compounds |
| GB9407138.8 | 1994-04-11 | ||
| GB9407138A GB9407138D0 (en) | 1994-04-11 | 1994-04-11 | Organic compounds |
| GB9421982A GB9421982D0 (en) | 1994-11-01 | 1994-11-01 | Organic compounds |
| GB9421982.1 | 1994-11-01 | ||
| PCT/EP1994/004191 WO1995016691A1 (fr) | 1993-12-17 | 1994-12-16 | Derives de rapamycine utilises comme immonosuppresseurs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2174731A1 CA2174731A1 (fr) | 1995-06-22 |
| CA2174731C true CA2174731C (fr) | 2006-10-31 |
Family
ID=37395713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002174731A Expired - Fee Related CA2174731C (fr) | 1993-12-17 | 1994-12-16 | Derives de rapamycine utilises comme immonosuppresseurs |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2174731C (fr) |
-
1994
- 1994-12-16 CA CA002174731A patent/CA2174731C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2174731A1 (fr) | 1995-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |