CA1246087A - Cyclic-disulfonic ester compounds - Google Patents
Cyclic-disulfonic ester compoundsInfo
- Publication number
- CA1246087A CA1246087A CA000472222A CA472222A CA1246087A CA 1246087 A CA1246087 A CA 1246087A CA 000472222 A CA000472222 A CA 000472222A CA 472222 A CA472222 A CA 472222A CA 1246087 A CA1246087 A CA 1246087A
- Authority
- CA
- Canada
- Prior art keywords
- ch2ch3
- formula
- chloride
- compound
- glyme
- 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.)
- Expired
Links
- -1 ester compounds Chemical class 0.000 title claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 8
- 229910052709 silver Inorganic materials 0.000 claims abstract description 8
- 239000004332 silver Substances 0.000 claims abstract description 8
- 229910001958 silver carbonate Inorganic materials 0.000 claims abstract description 8
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 18
- 241001465754 Metazoa Species 0.000 abstract description 17
- 125000000542 sulfonic acid group Chemical group 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 6
- 238000005804 alkylation reaction Methods 0.000 abstract description 5
- 238000007344 nucleophilic reaction Methods 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 14
- 208000003747 lymphoid leukemia Diseases 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 108020004414 DNA Proteins 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 8
- 206010033128 Ovarian cancer Diseases 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000007912 intraperitoneal administration Methods 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- DJSXAWRMVVSQDV-UHFFFAOYSA-L C(S(=O)(=O)[O-])S(=O)(=O)[O-].[Ag+2] Chemical compound C(S(=O)(=O)[O-])S(=O)(=O)[O-].[Ag+2] DJSXAWRMVVSQDV-UHFFFAOYSA-L 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 210000000481 breast Anatomy 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 208000032839 leukemia Diseases 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OPUAWDUYWRUIIL-UHFFFAOYSA-L methanedisulfonate Chemical compound [O-]S(=O)(=O)CS([O-])(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-L 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- GWAOOGWHPITOEY-UHFFFAOYSA-N 1,5,2,4-dioxadithiane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCO1 GWAOOGWHPITOEY-UHFFFAOYSA-N 0.000 description 3
- RYIRMSRYCSMGJA-UHFFFAOYSA-N 1,5,2,4-dioxadithiepane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCCO1 RYIRMSRYCSMGJA-UHFFFAOYSA-N 0.000 description 3
- APPZESCOGKWYIH-UHFFFAOYSA-N 1,5,2,4-dioxadithiocane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCCCO1 APPZESCOGKWYIH-UHFFFAOYSA-N 0.000 description 3
- FGNILISQKWJFES-UHFFFAOYSA-N 1,5,2,4-dioxadithionane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCCCCO1 FGNILISQKWJFES-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000000719 anti-leukaemic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- DKZQZHQHDMVGHE-UHFFFAOYSA-N methanedisulfonyl chloride Chemical compound ClS(=O)(=O)CS(Cl)(=O)=O DKZQZHQHDMVGHE-UHFFFAOYSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000400611 Eucalyptus deanei Species 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229960002092 busulfan Drugs 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- VWRZUKFQNHZBOK-UHFFFAOYSA-N 1,5,2,4-dioxadithiecane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCCCCCO1 VWRZUKFQNHZBOK-UHFFFAOYSA-N 0.000 description 1
- UUVVGFXVPHOAIV-UHFFFAOYSA-N 1,5,2,4-dioxadithiocane Chemical compound O1SCSOCCC1 UUVVGFXVPHOAIV-UHFFFAOYSA-N 0.000 description 1
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 1
- LKPFWCPZERQLFI-UHFFFAOYSA-N 2,4,6-trimethylpyridine;hydrochloride Chemical compound Cl.CC1=CC(C)=NC(C)=C1 LKPFWCPZERQLFI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000000970 DNA cross-linking effect Effects 0.000 description 1
- 231100001074 DNA strand break Toxicity 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- YFOUDCBQRHVVRR-UHFFFAOYSA-N OCCO.COCCOC Chemical compound OCCO.COCCOC YFOUDCBQRHVVRR-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000011102 Thera Species 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000005690 diesters Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- DBNBYVDVUHEYAX-UHFFFAOYSA-N ethane-1,1-disulfonate;hydron Chemical compound OS(=O)(=O)C(C)S(O)(=O)=O DBNBYVDVUHEYAX-UHFFFAOYSA-N 0.000 description 1
- XTEXMYNJEMCTNI-UHFFFAOYSA-N ethene;methane Chemical compound C.C=C XTEXMYNJEMCTNI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- JFUIHGAGFMFNRD-UHFFFAOYSA-N fica Chemical compound FC1=CC=C2NC(C(=O)NCCS)=CC2=C1 JFUIHGAGFMFNRD-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 229940090009 myleran Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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
- C07F7/0834—Compounds having one or more O-Si linkage
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/570,786 US4950768A (en) | 1984-01-16 | 1984-01-16 | Cyclic disulfonic ester cross-linking compounds |
| US570,786 | 1984-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1246087A true CA1246087A (en) | 1988-12-06 |
Family
ID=24281052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000472222A Expired CA1246087A (en) | 1984-01-16 | 1985-01-16 | Cyclic-disulfonic ester compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4950768A (https=) |
| EP (1) | EP0168478B1 (https=) |
| JP (1) | JPS61501089A (https=) |
| CA (1) | CA1246087A (https=) |
| DE (1) | DE3569237D1 (https=) |
| WO (1) | WO1985003075A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5849482A (en) * | 1988-09-28 | 1998-12-15 | Epoch Pharmaceuticals, Inc. | Crosslinking oligonucleotides |
| USRE38416E1 (en) | 1988-09-28 | 2004-02-03 | Epoch Biosciences, Inc. | Cross-linking oligonucleotides |
| US5824796A (en) * | 1988-09-28 | 1998-10-20 | Epoch Pharmaceuticals, Inc. | Cross-linking oligonucleotides |
| EP0472648A4 (en) * | 1989-05-18 | 1992-09-16 | Microprobe Corporation | Crosslinking oligonucleotides |
| US6136601A (en) * | 1991-08-21 | 2000-10-24 | Epoch Pharmaceuticals, Inc. | Targeted mutagenesis in living cells using modified oligonucleotides |
| TR200002243T2 (tr) * | 1997-11-10 | 2000-12-21 | Memorial Sloan-Kettering Cancer Center | Arsenik trioksitin hazırlanması için işlem ve bunların kanser tedavisi için kullanımı. |
| JP4033074B2 (ja) | 2002-08-29 | 2008-01-16 | 日本電気株式会社 | 二次電池用電解液およびそれを用いた二次電池 |
| WO2005029613A1 (ja) | 2003-09-16 | 2005-03-31 | Nec Corporation | 非水電解液二次電池 |
| JP4725728B2 (ja) * | 2003-12-15 | 2011-07-13 | 日本電気株式会社 | 二次電池 |
| US8445144B2 (en) | 2003-12-15 | 2013-05-21 | Nec Corporation | Additive for an electrolyte solution for an electrochemical device |
| JP4588407B2 (ja) * | 2004-04-28 | 2010-12-01 | 住友化学株式会社 | 環式ジスルホン酸エステルの製造方法 |
| JP2006188449A (ja) * | 2005-01-05 | 2006-07-20 | Sumitomo Chemical Co Ltd | 環式ジスルホン酸エステルの製造方法 |
| JP4577499B2 (ja) * | 2005-01-28 | 2010-11-10 | 日本電気株式会社 | メチレンジスルホニルクロライド及びその誘導体の製造方法 |
| TWI410413B (zh) * | 2006-04-26 | 2013-10-01 | Sumitomo Seika Chemicals | Preparation method of methylene disulfonate compound |
| TWI401250B (zh) | 2006-06-19 | 2013-07-11 | Wako Pure Chem Ind Ltd | 環狀二磺酸酯之製造方法 |
| CN101511782B (zh) | 2006-09-12 | 2013-08-07 | 和光纯药工业株式会社 | 磺酸酯的制造方法 |
| US8124793B2 (en) * | 2007-11-27 | 2012-02-28 | Gail Marie Cronyn, legal representative | Derivatives of ethylene methanedisulfonate as cancer chemotherapeutic agents |
| JP5169400B2 (ja) | 2008-04-07 | 2013-03-27 | Ｎｅｃエナジーデバイス株式会社 | 非水電解液およびそれを用いた非水電解液二次電池 |
| JP5408702B2 (ja) | 2009-01-23 | 2014-02-05 | Ｎｅｃエナジーデバイス株式会社 | リチウムイオン電池 |
| JP5305446B2 (ja) * | 2009-03-19 | 2013-10-02 | Ｎｅｃエナジーデバイス株式会社 | 非水電解液およびそれを用いた非水電解液二次電池 |
| US20120115037A1 (en) | 2009-07-09 | 2012-05-10 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Polymer gel electrolyte and polymer secondary battery using same |
| JPWO2011096572A1 (ja) | 2010-02-08 | 2013-06-13 | Ｎｅｃエナジーデバイス株式会社 | 非水電解液二次電池 |
| WO2011099580A1 (ja) | 2010-02-10 | 2011-08-18 | Ｎｅｃエナジーデバイス株式会社 | 非水系電解液およびそれを備えるリチウムイオン二次電池 |
| TWI508956B (zh) | 2010-08-25 | 2015-11-21 | Sumitomo Seika Chemicals | Preparation method of methylene disulfonate compound |
| JP5724366B2 (ja) * | 2010-12-21 | 2015-05-27 | セントラル硝子株式会社 | 環状ジスルホン酸エステル化合物の製造方法 |
| CA3148408A1 (en) | 2019-07-23 | 2021-01-28 | Sumitomo Seika Chemicals Co., Ltd. | Method for producing cyclic disulfonic acid ester compound |
| WO2021015219A1 (ja) | 2019-07-23 | 2021-01-28 | 住友精化株式会社 | メチレンジスルホネート化合物の製造方法 |
| CN112574167B (zh) * | 2020-12-07 | 2021-11-09 | 烟台海川化学制品有限公司 | 一种甲烷二磺酸亚甲酯的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB700677A (en) * | 1950-05-09 | 1953-12-09 | Wellcome Found | Improvements in or relating to aliphatic sulphonic acid esters of therapeutic value |
| AT210874B (de) * | 1959-02-13 | 1960-08-25 | Leuna Werke Veb | Verfahren zur Herstellung von neuen Polysulfosäureestern |
| DE1124032B (de) * | 1960-06-25 | 1962-02-22 | Basf Ag | Verfahren zur Herstellung von Salzen der Halbester der AEthandisulfonsaeure |
| DE1277247B (de) * | 1965-12-08 | 1968-09-12 | Basf Ag | Verfahren zur Herstellung von Vinylsulfonsaeurealkylestern |
| DE3004692A1 (de) * | 1980-02-08 | 1981-08-13 | Agfa-Gevaert Ag, 5090 Leverkusen | Hydroxyalkansulfonsaeure-sulfoalkylester |
-
1984
- 1984-01-16 US US06/570,786 patent/US4950768A/en not_active Expired - Lifetime
-
1985
- 1985-01-14 EP EP85900874A patent/EP0168478B1/en not_active Expired
- 1985-01-14 DE DE8585900874T patent/DE3569237D1/de not_active Expired
- 1985-01-14 WO PCT/US1985/000057 patent/WO1985003075A1/en not_active Ceased
- 1985-01-14 JP JP60500579A patent/JPS61501089A/ja active Granted
- 1985-01-16 CA CA000472222A patent/CA1246087A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3569237D1 (en) | 1989-05-11 |
| JPH0544946B2 (https=) | 1993-07-07 |
| EP0168478A1 (en) | 1986-01-22 |
| EP0168478A4 (en) | 1986-11-07 |
| US4950768A (en) | 1990-08-21 |
| EP0168478B1 (en) | 1989-04-05 |
| JPS61501089A (ja) | 1986-05-29 |
| WO1985003075A1 (en) | 1985-07-18 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |