CA2439256A1 - (z)-styrylbenzylsulfones and pharmaceutical uses thereof - Google Patents
(z)-styrylbenzylsulfones and pharmaceutical uses thereof Download PDFInfo
- Publication number
- CA2439256A1 CA2439256A1 CA002439256A CA2439256A CA2439256A1 CA 2439256 A1 CA2439256 A1 CA 2439256A1 CA 002439256 A CA002439256 A CA 002439256A CA 2439256 A CA2439256 A CA 2439256A CA 2439256 A1 CA2439256 A1 CA 2439256A1
- Authority
- CA
- Canada
- Prior art keywords
- alkoxy
- group
- compound according
- alkyl
- halogen
- 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
- MRTIWTGAGMZREP-QXMHVHEDSA-N [(z)-2-phenylethenyl]sulfonylmethylbenzene Chemical class C=1C=CC=CC=1\C=C/S(=O)(=O)CC1=CC=CC=C1 MRTIWTGAGMZREP-QXMHVHEDSA-N 0.000 title abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- -1 for example Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 58
- 210000004027 cell Anatomy 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 11
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 210000004881 tumor cell Anatomy 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000006907 apoptotic process Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000009905 Neurofibromatoses Diseases 0.000 claims description 3
- 208000016738 bone Paget disease Diseases 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 208000011803 breast fibrocystic disease Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims description 3
- 230000007882 cirrhosis Effects 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 230000004761 fibrosis Effects 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 208000011379 keloid formation Diseases 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 201000004931 neurofibromatosis Diseases 0.000 claims description 3
- 230000000750 progressive effect Effects 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims description 3
- 230000002611 ovarian Effects 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000001028 anti-proliverative effect Effects 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 29
- 125000004429 atom Chemical group 0.000 description 23
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 22
- 230000003647 oxidation Effects 0.000 description 22
- 238000007254 oxidation reaction Methods 0.000 description 22
- 229910052708 sodium Inorganic materials 0.000 description 22
- 239000011734 sodium Substances 0.000 description 22
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 8
- WZDKIPVHBCBPCR-QXMHVHEDSA-N [(z)-2-benzylsulfanylethenyl]benzene Chemical class C=1C=CC=CC=1CS\C=C/C1=CC=CC=C1 WZDKIPVHBCBPCR-QXMHVHEDSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000007911 parenteral administration Methods 0.000 description 5
- WNRZZMBEORNQMB-UHFFFAOYSA-N (2-chloro-4-methoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C(Cl)=C1 WNRZZMBEORNQMB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HRUJQXRGWQWYDH-UHFFFAOYSA-N 1-ethynyl-2,4-difluorobenzene Chemical group FC1=CC=C(C#C)C(F)=C1 HRUJQXRGWQWYDH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- ZSPXTTVUJDSRNJ-UHFFFAOYSA-N (2,4-dichlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1Cl ZSPXTTVUJDSRNJ-UHFFFAOYSA-N 0.000 description 2
- DVAWWNQISAMREX-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)methanethiol Chemical compound FC1=CC=C(CS)C(Cl)=C1 DVAWWNQISAMREX-UHFFFAOYSA-N 0.000 description 2
- CUCKXDPCCYHFMQ-UHFFFAOYSA-N (4-bromophenyl)methanethiol Chemical compound SCC1=CC=C(Br)C=C1 CUCKXDPCCYHFMQ-UHFFFAOYSA-N 0.000 description 2
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 2
- UGPZOWXCYINLLF-UHFFFAOYSA-N (4-ethynyl-2-methoxyphenyl) acetate Chemical group COC1=CC(C#C)=CC=C1OC(C)=O UGPZOWXCYINLLF-UHFFFAOYSA-N 0.000 description 2
- RKTRHMNWVZRZJQ-UHFFFAOYSA-N (4-fluorophenyl)methanethiol Chemical compound FC1=CC=C(CS)C=C1 RKTRHMNWVZRZJQ-UHFFFAOYSA-N 0.000 description 2
- ZJBQVHITAJZERN-UHFFFAOYSA-N 1,2-dichloro-3-ethynylbenzene Chemical group ClC1=CC=CC(C#C)=C1Cl ZJBQVHITAJZERN-UHFFFAOYSA-N 0.000 description 2
- NFMXTOPFQVKEMY-UHFFFAOYSA-N 1-ethynyl-2,3-dimethylbenzene Chemical group CC1=CC=CC(C#C)=C1C NFMXTOPFQVKEMY-UHFFFAOYSA-N 0.000 description 2
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical group COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 2
- GMODJHLJRNXLMC-UHFFFAOYSA-N 1-ethynyl-2,4-dimethylbenzene Chemical group CC1=CC=C(C#C)C(C)=C1 GMODJHLJRNXLMC-UHFFFAOYSA-N 0.000 description 2
- RMSZXRRYRZBYTC-UHFFFAOYSA-N 2,4-dichloro-1-ethynylbenzene Chemical group ClC1=CC=C(C#C)C(Cl)=C1 RMSZXRRYRZBYTC-UHFFFAOYSA-N 0.000 description 2
- WMNRKIVJDZUMOE-UHFFFAOYSA-N 4-ethynyl-2-methoxyphenol Chemical group COC1=CC(C#C)=CC=C1O WMNRKIVJDZUMOE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- YPFVPWQTXAOXBW-UHFFFAOYSA-N Br.Br.C=CC1=CC=CC=C1 Chemical class Br.Br.C=CC1=CC=CC=C1 YPFVPWQTXAOXBW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- OUMRUWRPTBYLRS-UHFFFAOYSA-N phenylmethanethiol;sodium Chemical compound [Na].SCC1=CC=CC=C1 OUMRUWRPTBYLRS-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SNCHEDBJOUWPMJ-UHFFFAOYSA-M sodium;phenylmethanethiolate Chemical compound [Na+].[S-]CC1=CC=CC=C1 SNCHEDBJOUWPMJ-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CXXYXDKJRAOBKX-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C(OC)=C1 CXXYXDKJRAOBKX-UHFFFAOYSA-N 0.000 description 1
- JHPCOZJGZURWKB-UHFFFAOYSA-N (2,4-dimethylphenyl)methanethiol Chemical compound CC1=CC=C(CS)C(C)=C1 JHPCOZJGZURWKB-UHFFFAOYSA-N 0.000 description 1
- SKLZTWWBEAOCPB-UHFFFAOYSA-N (2-aminophenyl)methanethiol Chemical compound NC1=CC=CC=C1CS SKLZTWWBEAOCPB-UHFFFAOYSA-N 0.000 description 1
- KFUKQIJXSWCBIA-UHFFFAOYSA-N (2-chloro-4-methylphenyl)methanethiol Chemical compound CC1=CC=C(CS)C(Cl)=C1 KFUKQIJXSWCBIA-UHFFFAOYSA-N 0.000 description 1
- XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
- FWYJPCBQOURGOR-UHFFFAOYSA-N (4-ethynylphenyl)phosphonic acid Chemical group OP(O)(=O)C1=CC=C(C#C)C=C1 FWYJPCBQOURGOR-UHFFFAOYSA-N 0.000 description 1
- PTDVPWWJRCOIIO-UHFFFAOYSA-N (4-methoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C=C1 PTDVPWWJRCOIIO-UHFFFAOYSA-N 0.000 description 1
- AGFYZLVFPSGUIX-UHFFFAOYSA-N (4-methylphenyl)methanethiol Chemical compound CC1=CC=C(CS)C=C1 AGFYZLVFPSGUIX-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- UXXHPGZDKSWUAI-YZLQMOBTSA-N 1-[(z)-1-[(z)-1,3-bis(2,4-dimethoxyphenyl)prop-2-enyl]sulfanyl-3-(2,4-dimethoxyphenyl)prop-2-enyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1\C=C/C(C=1C(=CC(OC)=CC=1)OC)SC(C=1C(=CC(OC)=CC=1)OC)\C=C/C1=CC=C(OC)C=C1OC UXXHPGZDKSWUAI-YZLQMOBTSA-N 0.000 description 1
- JDRVDKZMAHCPSK-IKBKFCNISA-N 1-[(z)-1-[(z)-1,3-bis(2,4-dimethylphenyl)prop-2-enyl]sulfanyl-3-(2,4-dimethylphenyl)prop-2-enyl]-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1\C=C/C(C=1C(=CC(C)=CC=1)C)SC(C=1C(=CC(C)=CC=1)C)\C=C/C1=CC=C(C)C=C1C JDRVDKZMAHCPSK-IKBKFCNISA-N 0.000 description 1
- ZWRZICCUOCTHEX-AXPXABNXSA-N 1-[(z)-3-(2-chloro-4-methoxyphenyl)-3-[(z)-1-(2-chloro-4-methoxyphenyl)-3-(2,3-dimethylphenyl)prop-2-enyl]sulfanylprop-1-enyl]-2,3-dimethylbenzene Chemical compound ClC1=CC(OC)=CC=C1C(\C=C/C=1C(=C(C)C=CC=1)C)SC(C=1C(=CC(OC)=CC=1)Cl)\C=C/C1=CC=CC(C)=C1C ZWRZICCUOCTHEX-AXPXABNXSA-N 0.000 description 1
- WAPBEQWCSKYAGR-WHYMJUELSA-N 1-[(z)-3-(4-bromophenyl)-3-[(z)-1-(4-bromophenyl)-3-(2,3-dichlorophenyl)prop-2-enyl]sulfanylprop-1-enyl]-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(\C=C/C(SC(\C=C/C=2C(=C(Cl)C=CC=2)Cl)C=2C=CC(Br)=CC=2)C=2C=CC(Br)=CC=2)=C1Cl WAPBEQWCSKYAGR-WHYMJUELSA-N 0.000 description 1
- IHWPXKFDWFWDDD-BMJUYKDLSA-N 1-[(z)-3-(4-bromophenyl)-3-[(z)-1-(4-bromophenyl)-3-(2,3-dimethylphenyl)prop-2-enyl]sulfanylprop-1-enyl]-2,3-dimethylbenzene Chemical compound CC1=CC=CC(\C=C/C(SC(\C=C/C=2C(=C(C)C=CC=2)C)C=2C=CC(Br)=CC=2)C=2C=CC(Br)=CC=2)=C1C IHWPXKFDWFWDDD-BMJUYKDLSA-N 0.000 description 1
- TUJOQSJQFRDWHX-DUGOVBPYSA-N 1-[(z)-3-(4-chlorophenyl)-3-[(z)-1-(4-chlorophenyl)-3-(2,4-difluorophenyl)prop-2-enyl]sulfanylprop-1-enyl]-2,4-difluorobenzene Chemical compound FC1=CC(F)=CC=C1\C=C/C(C=1C=CC(Cl)=CC=1)SC(C=1C=CC(Cl)=CC=1)\C=C/C1=CC=C(F)C=C1F TUJOQSJQFRDWHX-DUGOVBPYSA-N 0.000 description 1
- ALEKDQZTNXPPJA-AXPXABNXSA-N 1-[(z)-3-(4-chlorophenyl)-3-[(z)-1-(4-chlorophenyl)-3-(2,4-dimethylphenyl)prop-2-enyl]sulfanylprop-1-enyl]-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1\C=C/C(C=1C=CC(Cl)=CC=1)SC(C=1C=CC(Cl)=CC=1)\C=C/C1=CC=C(C)C=C1C ALEKDQZTNXPPJA-AXPXABNXSA-N 0.000 description 1
- MELOGFKBWVNCMO-YZLQMOBTSA-N 1-[(z)-3-[(z)-3-(2,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-enyl]sulfanyl-3-(4-fluorophenyl)prop-1-enyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1\C=C/C(C=1C=CC(F)=CC=1)SC(C=1C=CC(F)=CC=1)\C=C/C1=CC=C(OC)C=C1OC MELOGFKBWVNCMO-YZLQMOBTSA-N 0.000 description 1
- HKRJRPOWFDPPIM-LPPGRIHKSA-N 2,4-dichloro-1-[(z)-1-[(z)-1-(2,4-dichlorophenyl)-3-(2,4-difluorophenyl)prop-2-enyl]sulfanyl-3-(2,4-difluorophenyl)prop-2-enyl]benzene Chemical compound FC1=CC(F)=CC=C1\C=C/C(C=1C(=CC(Cl)=CC=1)Cl)SC(C=1C(=CC(Cl)=CC=1)Cl)\C=C/C1=CC=C(F)C=C1F HKRJRPOWFDPPIM-LPPGRIHKSA-N 0.000 description 1
- VSINARGSOQLHQP-PVRNWPCDSA-N 2,4-dichloro-1-[(z)-3-(2-chloro-4-methylphenyl)-3-[(z)-1-(2-chloro-4-methylphenyl)-3-(2,4-dichlorophenyl)prop-2-enyl]sulfanylprop-1-enyl]benzene Chemical compound ClC1=CC(C)=CC=C1C(\C=C/C=1C(=CC(Cl)=CC=1)Cl)SC(C=1C(=CC(C)=CC=1)Cl)\C=C/C1=CC=C(Cl)C=C1Cl VSINARGSOQLHQP-PVRNWPCDSA-N 0.000 description 1
- SKAJYNAXVGRKBH-DUGOVBPYSA-N 2,4-dichloro-1-[(z)-3-[(z)-3-(2,4-dichlorophenyl)-1-(4-fluorophenyl)prop-2-enyl]sulfanyl-3-(4-fluorophenyl)prop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(\C=C/C=1C(=CC(Cl)=CC=1)Cl)SC(C=1C=CC(F)=CC=1)\C=C/C1=CC=C(Cl)C=C1Cl SKAJYNAXVGRKBH-DUGOVBPYSA-N 0.000 description 1
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- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001672 cytoproliferative effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002518 glial effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000020071 rectified spirit Nutrition 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27176201P | 2001-02-27 | 2001-02-27 | |
| US60/271,762 | 2001-02-27 | ||
| PCT/US2002/005817 WO2002067913A1 (en) | 2001-02-27 | 2002-02-26 | (z)-styrylbenzylsulfones and pharmaceutical uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2439256A1 true CA2439256A1 (en) | 2002-09-06 |
Family
ID=23036961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002439256A Abandoned CA2439256A1 (en) | 2001-02-27 | 2002-02-26 | (z)-styrylbenzylsulfones and pharmaceutical uses thereof |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6833480B2 (enExample) |
| EP (1) | EP1379228A4 (enExample) |
| JP (1) | JP2004521126A (enExample) |
| CA (1) | CA2439256A1 (enExample) |
| WO (1) | WO2002067913A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6767926B1 (en) * | 1999-10-12 | 2004-07-27 | Temple University - Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
| ATE525067T1 (de) * | 2002-02-28 | 2011-10-15 | Univ Temple | Amino-substituierte (e)-2,6-dialkoxystyryl 4- substituierte benzylsulfone zur behandlung von proliferierenden erkrankungen |
| WO2005046599A2 (en) * | 2003-11-14 | 2005-05-26 | Temple University - Of The Commonwealth System Of Higher Education | Alpha, beta-unsaturated sulfoxides for treating proliferative disorders |
| DK1740530T3 (da) | 2004-03-16 | 2017-01-09 | Temple Univ - Of The Commonwealth System Of Higher Education | Substituerede phenoxy- og phenylthioderivater til behandling af proliferative forstyrrelser |
| ATE529106T1 (de) | 2004-06-24 | 2011-11-15 | Univ Temple | Alpha-, beta-ungesättigte sulfone, sulfonoxide, sulfonimide, sulfinimide, acylsulfonamide und acylsulfinamide und therapeutische verwendungen damit |
| GB0604233D0 (en) * | 2006-03-02 | 2006-04-12 | Syngenta Participations Ag | Process |
| US8735620B2 (en) | 2008-12-17 | 2014-05-27 | Epr Pharmaceuticals Pvt. Ltd | Processes for preparing (E)-styrylbenzylsulfone compounds and uses thereof for treating proliferative disorders |
| WO2014047110A2 (en) | 2012-09-20 | 2014-03-27 | Temple University - Of The Commonwealth System Of Higher Education | Substituted alkyl diaryl derivatives, methods of preparation and uses |
| ES2864681T3 (es) | 2012-12-07 | 2021-10-14 | Onconova Therapeutics Inc | Tratamiento del cáncer hematológico refractario a un agente contra el cáncer |
| WO2017023912A1 (en) | 2015-08-03 | 2017-02-09 | Temple University - Of The Commonwealth System Of Higher Education | 2,4,6-trialkoxystryl aryl sulfones, sulfonamides and carboxamides, and methods of preparation and use |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2532612A (en) * | 1945-08-29 | 1950-12-05 | Union Oil Co | Preparation of unsaturated thio-ethers |
| US3185743A (en) | 1960-08-24 | 1965-05-25 | Union Carbide Corp | Production of olefinic compounds from allyl sulfones |
| US3463774A (en) * | 1963-03-18 | 1969-08-26 | Hoffmann La Roche | Novel 4,1-benzothiazepin-2-(1h)-ones and 4,1-benzothiazepines |
| US3418101A (en) | 1965-12-15 | 1968-12-24 | Pennsalt Chemicals Corp | Process for plant desiccation |
| US3514386A (en) * | 1967-12-11 | 1970-05-26 | Exxon Research Engineering Co | Stereoselective addition of thiols to acetylenic compounds |
| US3917714A (en) * | 1972-09-06 | 1975-11-04 | American Cyanamid Co | Bis(alkylsulfonyl)vinylbenzenes |
| US4161407A (en) * | 1977-10-06 | 1979-07-17 | Eastman Kodak Company | Crosslinkable polymers having vinylsulfonyl groups or styrylsulfonyl groups and their use as hardeners for gelatin |
| US4386221A (en) * | 1981-10-28 | 1983-05-31 | Eastman Kodak Company | Process for the preparation of aryl alkyl sulfones and aryl vinyl sulfones |
| US4937388A (en) * | 1985-08-09 | 1990-06-26 | Imperial Chemical Industries Plc | Insecticidal ethers |
| US5659087A (en) * | 1995-06-07 | 1997-08-19 | Eli Lilly And Company | Diarylvinyl sulfoxides |
| US5733909A (en) * | 1996-02-01 | 1998-03-31 | Merck Frosst Canada, Inc. | Diphenyl stilbenes as prodrugs to COX-2 inhibitors |
| EP1027330B1 (en) * | 1997-10-03 | 2004-12-08 | Temple University of the Commonwealth System of Higher Education | Styryl sulfone anticancer agents |
| US6201154B1 (en) | 1999-03-31 | 2001-03-13 | Temple University-Of The Commonwealth Of Higher Education | Z-styryl sulfone anticancer agents |
| DE60020954T2 (de) | 1999-04-02 | 2006-05-11 | Temple University Of The Commonwealth System Of Higher Education | (e)-styrylsulfone als krebsbestreitende mittel |
| US6185743B1 (en) * | 1999-06-10 | 2001-02-13 | John D. Mick | Beach toga with partial belt |
| US6418101B1 (en) * | 1999-09-03 | 2002-07-09 | Zen Research (Ireland), Ltd. | Digital read channel for optical disk reader |
| CA2387539C (en) * | 1999-10-12 | 2010-09-21 | Temple University - Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
| US6486210B2 (en) * | 2000-04-14 | 2002-11-26 | Temple University—Of the Commonwealth System of Higher Education | Substituted styryl benzylsulfones for treating proliferative disorders |
-
2002
- 2002-02-26 EP EP02714999A patent/EP1379228A4/en not_active Withdrawn
- 2002-02-26 WO PCT/US2002/005817 patent/WO2002067913A1/en not_active Ceased
- 2002-02-26 CA CA002439256A patent/CA2439256A1/en not_active Abandoned
- 2002-02-26 US US10/469,056 patent/US6833480B2/en not_active Expired - Lifetime
- 2002-02-26 JP JP2002567281A patent/JP2004521126A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1379228A1 (en) | 2004-01-14 |
| US20040133030A1 (en) | 2004-07-08 |
| EP1379228A4 (en) | 2006-01-04 |
| WO2002067913A8 (en) | 2002-11-14 |
| US6833480B2 (en) | 2004-12-21 |
| JP2004521126A (ja) | 2004-07-15 |
| WO2002067913A1 (en) | 2002-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20080226 |