DK2303021T3 - RELATIONSHIPS FOR TREATING CANCER - Google Patents
RELATIONSHIPS FOR TREATING CANCER Download PDFInfo
- Publication number
- DK2303021T3 DK2303021T3 DK09835407.9T DK09835407T DK2303021T3 DK 2303021 T3 DK2303021 T3 DK 2303021T3 DK 09835407 T DK09835407 T DK 09835407T DK 2303021 T3 DK2303021 T3 DK 2303021T3
- Authority
- DK
- Denmark
- Prior art keywords
- compound
- methanone
- trimethoxyphenyl
- thiazol
- cancer
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 59
- 201000011510 cancer Diseases 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 168
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 49
- -1 mesylamino Chemical group 0.000 claims description 45
- 206010060862 Prostate cancer Diseases 0.000 claims description 36
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 36
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- LNESSNOGBADQPV-UHFFFAOYSA-N [2-(4-fluorophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(F)=CC=2)=C1 LNESSNOGBADQPV-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- WZEMDWPKLKAUOH-UHFFFAOYSA-N (2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC=CC=2)=C1 WZEMDWPKLKAUOH-UHFFFAOYSA-N 0.000 claims description 11
- OZVQTPZSBXLFRT-UHFFFAOYSA-N [2-(4-aminophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(N)=CC=2)=C1 OZVQTPZSBXLFRT-UHFFFAOYSA-N 0.000 claims description 11
- FNFDWGCEPDFHHD-UHFFFAOYSA-N [2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 FNFDWGCEPDFHHD-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- OGHQVBIGARGOHC-UHFFFAOYSA-N [2-(4-ethylphenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C1=NC(C(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=CS1 OGHQVBIGARGOHC-UHFFFAOYSA-N 0.000 claims description 10
- ROYIPIXFQBIZPN-UHFFFAOYSA-N [2-(4-methylphenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(C)=CC=2)=C1 ROYIPIXFQBIZPN-UHFFFAOYSA-N 0.000 claims description 10
- CRCDSSNETKMUKH-UHFFFAOYSA-N [2-(4-nitrophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 CRCDSSNETKMUKH-UHFFFAOYSA-N 0.000 claims description 10
- ZVEYCXZZSZYVNG-UHFFFAOYSA-N 4-[4-(3,4,5-trimethoxybenzoyl)-1,3-thiazol-2-yl]benzonitrile Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)C#N)=C1 ZVEYCXZZSZYVNG-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- ZQGOBXPCJJATRI-UHFFFAOYSA-N [2-(4-bromophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(Br)=CC=2)=C1 ZQGOBXPCJJATRI-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
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- 125000001041 indolyl group Chemical group 0.000 claims description 8
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- 208000032839 leukemia Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010038389 Renal cancer Diseases 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 201000007455 central nervous system cancer Diseases 0.000 claims description 5
- 201000010982 kidney cancer Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 201000000849 skin cancer Diseases 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims 9
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- 230000000694 effects Effects 0.000 description 36
- 201000001441 melanoma Diseases 0.000 description 36
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 21
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 230000001028 anti-proliverative effect Effects 0.000 description 14
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- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 12
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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| US6187508P | 2008-06-16 | 2008-06-16 | |
| PCT/US2009/047572 WO2010074776A2 (en) | 2008-06-16 | 2009-06-16 | Compounds for the treatment of cancer |
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| DK2303021T3 true DK2303021T3 (en) | 2019-04-08 |
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| DK15168526.0T DK2959900T3 (en) | 2008-06-16 | 2009-06-16 | CONNECTION TO TREATMENT OF CANCER |
| DK17196904.1T DK3289876T3 (da) | 2008-06-16 | 2009-06-16 | Forbindelser til behandling af cancer |
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- 2009-06-16 MX MX2010014066A patent/MX2010014066A/es active IP Right Grant
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- 2009-06-16 ES ES15168526.0T patent/ES2629927T3/es active Active
- 2009-06-16 KR KR1020177032778A patent/KR20170128623A/ko not_active Ceased
- 2009-06-16 AU AU2009330686A patent/AU2009330686B2/en active Active
- 2009-06-16 DK DK17196904.1T patent/DK3289876T3/da active
- 2009-06-16 US US12/485,881 patent/US8592465B2/en active Active
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2010
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2012
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2018
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2019
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