CA2706914A1 - Biocompatible biodegradable fumagillin analog conjugates - Google Patents
Biocompatible biodegradable fumagillin analog conjugates Download PDFInfo
- Publication number
- CA2706914A1 CA2706914A1 CA2706914A CA2706914A CA2706914A1 CA 2706914 A1 CA2706914 A1 CA 2706914A1 CA 2706914 A CA2706914 A CA 2706914A CA 2706914 A CA2706914 A CA 2706914A CA 2706914 A1 CA2706914 A1 CA 2706914A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- conjugate
- fumagillin
- optionally substituted
- pharmaceutically acceptable
- 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
- NGGMYCMLYOUNGM-CSDLUJIJSA-N fumagillin Chemical class C([C@H]([C@H]([C@@H]1[C@]2(C)[C@H](O2)CC=C(C)C)OC)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)C[C@@]21CO2 NGGMYCMLYOUNGM-CSDLUJIJSA-N 0.000 title claims abstract description 292
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- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 167
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- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 68
- -1 substituted Chemical class 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- NGGMYCMLYOUNGM-UHFFFAOYSA-N (-)-fumagillin Natural products O1C(CC=C(C)C)C1(C)C1C(OC)C(OC(=O)C=CC=CC=CC=CC(O)=O)CCC21CO2 NGGMYCMLYOUNGM-UHFFFAOYSA-N 0.000 claims description 44
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- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 29
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- KRNJGCZJVCWXFN-JGVFFNPUSA-N (2s,3r)-2-methyl-3-(3-methylbut-2-enyl)oxirane Chemical group C[C@@H]1O[C@@H]1CC=C(C)C KRNJGCZJVCWXFN-JGVFFNPUSA-N 0.000 claims description 15
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- YAQYVSLBYMDWPD-JGVFFNPUSA-N (2s,3r)-2-methyl-3-(3-methylbutyl)oxirane Chemical group CC(C)CC[C@H]1O[C@H]1C YAQYVSLBYMDWPD-JGVFFNPUSA-N 0.000 claims description 12
- IILGVAQPFQYXIO-UHFFFAOYSA-N 2-methylhepta-2,5-diene Chemical group CC=CCC=C(C)C IILGVAQPFQYXIO-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
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- WXGOLMICHIGDMF-SGAXSIHGSA-N (z)-n-phenylmethoxyethanimine Chemical group C\C=N/OCC1=CC=CC=C1 WXGOLMICHIGDMF-SGAXSIHGSA-N 0.000 claims description 10
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 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 3
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- 231100000228 neurotoxicity Toxicity 0.000 claims description 3
- 230000007135 neurotoxicity Effects 0.000 claims description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 2
- 125000000466 oxiranyl group Chemical group 0.000 claims 2
- 102100023174 Methionine aminopeptidase 2 Human genes 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
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- Organic Chemistry (AREA)
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| US458207P | 2007-11-28 | 2007-11-28 | |
| US61/004,582 | 2007-11-28 | ||
| PCT/US2008/084539 WO2009073445A2 (en) | 2007-11-28 | 2008-11-24 | Biocompatible biodegradable fumagillin analog conjugates |
Publications (1)
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| CA2706914A1 true CA2706914A1 (en) | 2009-06-11 |
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| CA2706914A Abandoned CA2706914A1 (en) | 2007-11-28 | 2008-11-24 | Biocompatible biodegradable fumagillin analog conjugates |
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| EP (1) | EP2217283A2 (enExample) |
| JP (1) | JP5557746B2 (enExample) |
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| NZ (2) | NZ600039A (enExample) |
| WO (1) | WO2009073445A2 (enExample) |
| ZA (1) | ZA201003819B (enExample) |
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| EP2217283A2 (en) | 2010-08-18 |
| ZA201003819B (en) | 2013-09-25 |
| EA201070657A1 (ru) | 2010-12-30 |
| EA020251B1 (ru) | 2014-09-30 |
| BRPI0820229A2 (pt) | 2017-05-09 |
| NZ600039A (en) | 2013-11-29 |
| AU2008331516B2 (en) | 2014-01-09 |
| US20130158046A1 (en) | 2013-06-20 |
| WO2009073445A3 (en) | 2010-01-28 |
| CN101990441A (zh) | 2011-03-23 |
| AU2008331516A1 (en) | 2009-06-11 |
| JP2011504964A (ja) | 2011-02-17 |
| MX2010005857A (es) | 2010-11-22 |
| NZ585547A (en) | 2012-12-21 |
| IL206057A0 (en) | 2010-11-30 |
| US8399512B2 (en) | 2013-03-19 |
| JP5557746B2 (ja) | 2014-07-23 |
| US20090148396A1 (en) | 2009-06-11 |
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