JPS60197654A - 制癌剤としての（アルキルスルホニル）メタンスルホン酸エステル - Google Patents

制癌剤としての（アルキルスルホニル）メタンスルホン酸エステル

Info

Publication number: JPS60197654A
Authority: JP; Japan
Prior art keywords: methylsulfonyl; formula; methanesulfonate; methyl; chloroethyl
Prior art date: 1983-12-06
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.): Granted

Application number

JP25842684A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0463870B2 (da

Inventor

ワイ　フルマー　シエイリー

チヤールズ　エイ　クロース

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Southern Research Institute

Original Assignee

Southern Research Institute

Priority date (The priority date 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 date listed.)

1983-12-06

Filing date

1984-12-06

Publication date

1985-10-07

1984-12-06 Application filed by Southern Research Institute filed Critical Southern Research Institute

1985-10-07 Publication of JPS60197654A publication Critical patent/JPS60197654A/ja

1992-10-13 Publication of JPH0463870B2 publication Critical patent/JPH0463870B2/ja

Status Granted legal-status Critical Current

Links

AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title description 11
229940098779 methanesulfonic acid Drugs 0.000 title description 4
-1 methanesulfonic acid ester Chemical class 0.000 title description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 title description 3
230000001093 anti-cancer Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
SEHSPJCWCBQHPF-UHFFFAOYSA-N 2-chloroethyl methylsulfonylmethanesulfonate Chemical compound CS(=O)(=O)CS(=O)(=O)OCCCl SEHSPJCWCBQHPF-UHFFFAOYSA-N 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
DLOFSTTTWPYQRY-UHFFFAOYSA-N 2-bromoethyl methylsulfonylmethanesulfonate Chemical compound CS(=O)(=O)CS(=O)(=O)OCCBr DLOFSTTTWPYQRY-UHFFFAOYSA-N 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
VQTHGECRQVEXQR-UHFFFAOYSA-N 2-chloroethyl 2-methylsulfonylpropane-2-sulfonate Chemical compound CS(=O)(=O)C(C)(C)S(=O)(=O)OCCCl VQTHGECRQVEXQR-UHFFFAOYSA-N 0.000 claims 1
NHVXCGMNKRDRNT-UHFFFAOYSA-N 2-fluoroethyl methylsulfonylmethanesulfonate Chemical compound CS(=O)(=O)CS(=O)(=O)OCCF NHVXCGMNKRDRNT-UHFFFAOYSA-N 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000011734 sodium Substances 0.000 description 22
239000000243 solution Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
241000699670 Mus sp. Species 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
206010028980 Neoplasm Diseases 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
238000010521 absorption reaction Methods 0.000 description 12
239000000463 material Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
239000000706 filtrate Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
238000002329 infrared spectrum Methods 0.000 description 9
238000000034 method Methods 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
201000011510 cancer Diseases 0.000 description 8
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000012360 testing method Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000000523 sample Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
DQDYGBSUPOHHMW-UHFFFAOYSA-N methylsulfonylmethanesulfonyl chloride Chemical compound CS(=O)(=O)CS(Cl)(=O)=O DQDYGBSUPOHHMW-UHFFFAOYSA-N 0.000 description 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
208000032839 leukemia Diseases 0.000 description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
FNKDLMUQVBRGKO-UHFFFAOYSA-M sodium;methylsulfonylmethanesulfonate Chemical compound [Na+].CS(=O)(=O)CS([O-])(=O)=O FNKDLMUQVBRGKO-UHFFFAOYSA-M 0.000 description 5
238000005406 washing Methods 0.000 description 5
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
BYMKUFGVNOCUCC-UHFFFAOYSA-N methylsulfonylmethanesulfonic acid Chemical compound CS(=O)(=O)CS(O)(=O)=O BYMKUFGVNOCUCC-UHFFFAOYSA-N 0.000 description 4
PGBVMJYMDPTURZ-UHFFFAOYSA-M sodium;1-methylsulfonylethanesulfonate Chemical compound [Na+].CS(=O)(=O)C(C)S([O-])(=O)=O PGBVMJYMDPTURZ-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007792 addition Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
230000001613 neoplastic effect Effects 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
LZDOOWRDGIKKEX-UHFFFAOYSA-N 1-methylsulfonylethanesulfonyl chloride Chemical compound CS(=O)(=O)C(C)S(Cl)(=O)=O LZDOOWRDGIKKEX-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010058467 Lung neoplasm malignant Diseases 0.000 description 2
208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
201000005202 lung cancer Diseases 0.000 description 2
208000020816 lung neoplasm Diseases 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
OZYNXOHFXJNCRE-UHFFFAOYSA-M sodium;2-methylsulfonylpropane-2-sulfonate Chemical compound [Na+].CS(=O)(=O)C(C)(C)S([O-])(=O)=O OZYNXOHFXJNCRE-UHFFFAOYSA-M 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
150000003461 sulfonyl halides Chemical class 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
SSQATBAJIXVRRB-UHFFFAOYSA-N 1-methylsulfonylethanesulfonic acid Chemical compound CS(=O)(=O)C(C)S(O)(=O)=O SSQATBAJIXVRRB-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
YBRDBYGCEIDLBX-UHFFFAOYSA-N 2-[(4-nitrophenyl)methyl]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=CC=N1 YBRDBYGCEIDLBX-UHFFFAOYSA-N 0.000 description 1
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
XBIQCPDVGCQEAX-UHFFFAOYSA-N 2-chloroethyl 1-methylsulfonylethanesulfonate Chemical compound CS(=O)(=O)C(C)S(=O)(=O)OCCCl XBIQCPDVGCQEAX-UHFFFAOYSA-N 0.000 description 1
BYEULZSQJFKHIP-UHFFFAOYSA-N 2-chloroethyl chloromethanesulfonate Chemical compound ClCCOS(=O)(=O)CCl BYEULZSQJFKHIP-UHFFFAOYSA-N 0.000 description 1
FMMYTRQXHORTCU-UHFFFAOYSA-N 2-chloroethyl methanesulfonate Chemical compound CS(=O)(=O)OCCCl FMMYTRQXHORTCU-UHFFFAOYSA-N 0.000 description 1
GGDYAKVUZMZKRV-UHFFFAOYSA-N 2-fluoroethanol Chemical compound OCCF GGDYAKVUZMZKRV-UHFFFAOYSA-N 0.000 description 1
101150032866 CDC11 gene Proteins 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
108700018454 CDC15 Proteins 0.000 description 1
102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 description 1
208000001382 Experimental Melanoma Diseases 0.000 description 1
101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
230000000719 anti-leukaemic effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000005998 bromoethyl group Chemical group 0.000 description 1
101150081467 cdc15 gene Proteins 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
SJEWVQQNCSXMNO-UHFFFAOYSA-N ethyl methylsulfonylmethanesulfonate Chemical class CCOS(=O)(=O)CS(C)(=O)=O SJEWVQQNCSXMNO-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000010265 fast atom bombardment Methods 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 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
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
229960004961 mechlorethamine Drugs 0.000 description 1
230000000684 melanotic effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical class C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 description 1
NHTGFMDYCVWGFX-UHFFFAOYSA-N methyl methylsulfonylmethanesulfonate Chemical compound COS(=O)(=O)CS(C)(=O)=O NHTGFMDYCVWGFX-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP25842684A 1983-12-06 1984-12-06 制癌剤としての（アルキルスルホニル）メタンスルホン酸エステル Granted JPS60197654A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US55843583A	1983-12-06	1983-12-06
US558435		1983-12-06
US672831		1984-11-19

Publications (2)

Publication Number	Publication Date
JPS60197654A true JPS60197654A (ja)	1985-10-07
JPH0463870B2 JPH0463870B2 (da)	1992-10-13

Family

ID=24229527

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP25842684A Granted JPS60197654A (ja)	1983-12-06	1984-12-06	制癌剤としての（アルキルスルホニル）メタンスルホン酸エステル

Country Status (1)

Country	Link
JP (1)	JPS60197654A (da)

1984
- 1984-12-06 JP JP25842684A patent/JPS60197654A/ja active Granted

Also Published As

Publication number	Publication date
JPH0463870B2 (da)	1992-10-13

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Browne et al.	1952	Isomeric Amino Alcohols from the Reaction of Styrene Oxide with Benzylamine
PL173794B1 (pl)	1998-05-29	Sposób wytwarzania oktadecylo-[2-(N-metylopiperydyno)-etylo]-fosforanu
DE2850078A1 (de)	1980-05-29	Aminopropanolderivate des 6-hydroxy-2,3,4,5-tetrahydro-1h-1- benzazepin-2-ons
KR20020094000A (ko)	2002-12-16	항종양제로서비스-(ｎ,ｎ'-비스-(2-할로에틸)아미노)포스포라미데이트
EP0006718A1 (en)	1980-01-09	1.2.4-Triazolidine-3.5-dione derivatives, process for their preparation and pharmaceutical compositions containing them
JPS60146852A (ja)	1985-08-02	プロパノ−ルアミン誘導体