CA2792198A1 - Macrocyclic lactone derivatives for the treatment of cancer - Google Patents
Macrocyclic lactone derivatives for the treatment of cancer Download PDFInfo
- Publication number
- CA2792198A1 CA2792198A1 CA2792198A CA2792198A CA2792198A1 CA 2792198 A1 CA2792198 A1 CA 2792198A1 CA 2792198 A CA2792198 A CA 2792198A CA 2792198 A CA2792198 A CA 2792198A CA 2792198 A1 CA2792198 A1 CA 2792198A1
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- hydroxy
- alkyl
- alkoxy
- hydrogen
- 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
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 52
- 201000011510 cancer Diseases 0.000 title claims abstract description 36
- 238000011282 treatment Methods 0.000 title claims abstract description 29
- 150000002596 lactones Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 150000003839 salts Chemical class 0.000 claims abstract description 42
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- 239000000651 prodrug Substances 0.000 claims abstract description 33
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- 241000124008 Mammalia Species 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 246
- 125000000217 alkyl group Chemical group 0.000 claims description 211
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- 125000003545 alkoxy group Chemical group 0.000 claims description 142
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 138
- 229910052736 halogen Inorganic materials 0.000 claims description 127
- 150000002367 halogens Chemical group 0.000 claims description 127
- 125000003118 aryl group Chemical group 0.000 claims description 120
- 125000000623 heterocyclic group Chemical group 0.000 claims description 104
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- -1 -NHCH2R20 Chemical group 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 23
- 206010025557 Malignant fibrous histiocytoma of bone Diseases 0.000 claims 3
- 208000018417 undifferentiated high grade pleomorphic sarcoma of bone Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 abstract description 27
- 230000008569 process Effects 0.000 abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QJVSMHJWAOSBMD-MYXYZBIASA-L pemetrexed disodium heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 QJVSMHJWAOSBMD-MYXYZBIASA-L 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000011476 stem cell transplantation Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 238000002626 targeted therapy Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- RTKIYFITIVXBLE-QEQCGCAPSA-N trichostatin A Chemical compound ONC(=O)/C=C/C(/C)=C/[C@@H](C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-QEQCGCAPSA-N 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000004222 uncontrolled growth Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26185609P | 2009-11-17 | 2009-11-17 | |
| US61/261,856 | 2009-11-17 | ||
| PCT/IB2010/055161 WO2011061666A1 (en) | 2009-11-17 | 2010-11-15 | Macrocyclic lactone derivatives for the treatment of cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2792198A1 true CA2792198A1 (en) | 2011-05-26 |
Family
ID=43566625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2792198A Abandoned CA2792198A1 (en) | 2009-11-17 | 2010-11-15 | Macrocyclic lactone derivatives for the treatment of cancer |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8637683B2 (enExample) |
| EP (1) | EP2501689A1 (enExample) |
| JP (1) | JP2013510899A (enExample) |
| KR (1) | KR20120092677A (enExample) |
| CN (1) | CN102666523A (enExample) |
| AU (1) | AU2010320557A1 (enExample) |
| CA (1) | CA2792198A1 (enExample) |
| IL (1) | IL219807A0 (enExample) |
| MX (1) | MX2012005618A (enExample) |
| NZ (1) | NZ600660A (enExample) |
| RU (1) | RU2012124817A (enExample) |
| WO (1) | WO2011061666A1 (enExample) |
| ZA (1) | ZA201204488B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ600662A (en) * | 2009-11-17 | 2014-05-30 | Piramal Entpr Ltd | Use of macrocyclic lactone derivatives for the treatment of inflammatory disorders |
| WO2014118740A1 (en) * | 2013-02-04 | 2014-08-07 | Piramal Enterprises Limited | Macrocyclic lactone derivatives and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9504617D0 (sv) * | 1995-12-22 | 1995-12-22 | Astra Ab | Active compounds II |
| NZ600662A (en) * | 2009-11-17 | 2014-05-30 | Piramal Entpr Ltd | Use of macrocyclic lactone derivatives for the treatment of inflammatory disorders |
-
2010
- 2010-11-15 CA CA2792198A patent/CA2792198A1/en not_active Abandoned
- 2010-11-15 EP EP10798188A patent/EP2501689A1/en not_active Withdrawn
- 2010-11-15 CN CN201080057594XA patent/CN102666523A/zh active Pending
- 2010-11-15 NZ NZ600660A patent/NZ600660A/en not_active IP Right Cessation
- 2010-11-15 JP JP2012539450A patent/JP2013510899A/ja active Pending
- 2010-11-15 WO PCT/IB2010/055161 patent/WO2011061666A1/en not_active Ceased
- 2010-11-15 KR KR1020127015787A patent/KR20120092677A/ko not_active Withdrawn
- 2010-11-15 RU RU2012124817/04A patent/RU2012124817A/ru not_active Application Discontinuation
- 2010-11-15 US US13/510,458 patent/US8637683B2/en not_active Expired - Fee Related
- 2010-11-15 AU AU2010320557A patent/AU2010320557A1/en not_active Abandoned
- 2010-11-15 MX MX2012005618A patent/MX2012005618A/es not_active Application Discontinuation
-
2012
- 2012-05-15 IL IL219807A patent/IL219807A0/en unknown
- 2012-06-18 ZA ZA2012/04488A patent/ZA201204488B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ600660A (en) | 2014-02-28 |
| AU2010320557A1 (en) | 2012-07-05 |
| KR20120092677A (ko) | 2012-08-21 |
| RU2012124817A (ru) | 2013-12-27 |
| US8637683B2 (en) | 2014-01-28 |
| ZA201204488B (en) | 2014-08-27 |
| US20120245183A1 (en) | 2012-09-27 |
| JP2013510899A (ja) | 2013-03-28 |
| MX2012005618A (es) | 2012-08-15 |
| CN102666523A (zh) | 2012-09-12 |
| WO2011061666A1 (en) | 2011-05-26 |
| IL219807A0 (en) | 2012-07-31 |
| EP2501689A1 (en) | 2012-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20151117 |