CA1082194A - Aliphatic sulfamates - Google Patents
Aliphatic sulfamatesInfo
- Publication number
- CA1082194A CA1082194A CA239,484A CA239484A CA1082194A CA 1082194 A CA1082194 A CA 1082194A CA 239484 A CA239484 A CA 239484A CA 1082194 A CA1082194 A CA 1082194A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- sulfamyl
- propanediol
- compound
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Aliphatic sulfamates Chemical class 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 16
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 13
- 229940035437 1,3-propanediol Drugs 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 11
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 11
- 239000012312 sodium hydride Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- WGBSTIRRHNSMRN-UHFFFAOYSA-N n-tert-butylsulfamoyl chloride Chemical group CC(C)(C)NS(Cl)(=O)=O WGBSTIRRHNSMRN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 6
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 4
- 230000035558 fertility Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 28
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- FUEBNTADACMZSM-UHFFFAOYSA-N 2-sulfamoyloxyethyl sulfamate Chemical compound NS(=O)(=O)OCCOS(N)(=O)=O FUEBNTADACMZSM-UHFFFAOYSA-N 0.000 description 5
- 201000010063 epididymitis Diseases 0.000 description 5
- 208000000509 infertility Diseases 0.000 description 5
- 230000036512 infertility Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004533 oil dispersion Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- NDYJEAUUNHDJMC-UHFFFAOYSA-N 2,2-diphenylpropane-1,3-diol Chemical compound C=1C=CC=CC=1C(CO)(CO)C1=CC=CC=C1 NDYJEAUUNHDJMC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZVPIIWCQFOHABK-UHFFFAOYSA-N (2,2-diphenyl-3-sulfamoyloxypropyl) sulfamate Chemical compound C=1C=CC=CC=1C(COS(N)(=O)=O)(COS(=O)(=O)N)C1=CC=CC=C1 ZVPIIWCQFOHABK-UHFFFAOYSA-N 0.000 description 3
- DFALGJJVPSYYCD-UHFFFAOYSA-N 3-sulfamoyloxypropyl sulfamate Chemical compound NS(=O)(=O)OCCCOS(N)(=O)=O DFALGJJVPSYYCD-UHFFFAOYSA-N 0.000 description 3
- XHCZRWMTVBHWQT-UHFFFAOYSA-N 4-sulfamoyloxybutyl sulfamate Chemical compound NS(=O)(=O)OCCCCOS(N)(=O)=O XHCZRWMTVBHWQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000013011 mating Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RLOLRLDKWZMQME-UHFFFAOYSA-N (2,2-dibenzyl-3-sulfamoyloxypropyl) sulfamate Chemical compound C=1C=CC=CC=1CC(COS(N)(=O)=O)(COS(=O)(=O)N)CC1=CC=CC=C1 RLOLRLDKWZMQME-UHFFFAOYSA-N 0.000 description 2
- BXPDYQDSZNQRLY-UHFFFAOYSA-N (2,2-dimethyl-3-sulfamoyloxypropyl) sulfamate Chemical compound NS(=O)(=O)OCC(C)(C)COS(N)(=O)=O BXPDYQDSZNQRLY-UHFFFAOYSA-N 0.000 description 2
- IUDLFTSIYDSEAU-UHFFFAOYSA-N (2-methyl-3-sulfamoyloxypropyl) sulfamate Chemical compound NS(=O)(=O)OCC(C)COS(N)(=O)=O IUDLFTSIYDSEAU-UHFFFAOYSA-N 0.000 description 2
- AZLRECYOMFCGTK-UHFFFAOYSA-N 2,2-dibenzylpropane-1,3-diol Chemical compound C=1C=CC=CC=1CC(CO)(CO)CC1=CC=CC=C1 AZLRECYOMFCGTK-UHFFFAOYSA-N 0.000 description 2
- OVOVXMVFDJXHAN-UHFFFAOYSA-N 2,2-dicyclohexylpropane-1,3-diol Chemical compound C1CCCCC1C(CO)(CO)C1CCCCC1 OVOVXMVFDJXHAN-UHFFFAOYSA-N 0.000 description 2
- QPIAAQDLOJNQMP-UHFFFAOYSA-N 2-ethyl-2-propylpropane-1,3-diol Chemical compound CCCC(CC)(CO)CO QPIAAQDLOJNQMP-UHFFFAOYSA-N 0.000 description 2
- AEARVEODHXFSKG-UHFFFAOYSA-N 6-sulfamoyloxyhexyl sulfamate Chemical compound NS(=O)(=O)OCCCCCCOS(N)(=O)=O AEARVEODHXFSKG-UHFFFAOYSA-N 0.000 description 2
- IPTXSYCLIWBHBX-UHFFFAOYSA-N 8-sulfamoyloxyoctyl sulfamate Chemical compound NS(=O)(=O)OCCCCCCCCOS(N)(=O)=O IPTXSYCLIWBHBX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QJQKZZCQOQXBQF-UHFFFAOYSA-N [2-methyl-2-(sulfamoyloxymethyl)pentyl] sulfamate Chemical compound NS(=O)(=O)OCC(C)(CCC)COS(N)(=O)=O QJQKZZCQOQXBQF-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- ASCHNMXUWBEZDM-UHFFFAOYSA-N chloridodioxygen(.) Chemical compound [O]OCl ASCHNMXUWBEZDM-UHFFFAOYSA-N 0.000 description 2
- 229960004926 chlorobutanol Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000004392 genitalia Anatomy 0.000 description 2
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 230000026234 pro-estrus Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 2
- DCDZQWVPDFADEZ-UHFFFAOYSA-N (2,2-dicyclohexyl-3-sulfamoyloxypropyl) sulfamate Chemical compound C1CCCCC1C(COS(N)(=O)=O)(COS(=O)(=O)N)C1CCCCC1 DCDZQWVPDFADEZ-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- OQKMEELIMCEPSK-UHFFFAOYSA-N 2-(diphenylsulfamoyloxy)ethyl n,n-diphenylsulfamate Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)S(=O)(=O)OCCOS(=O)(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 OQKMEELIMCEPSK-UHFFFAOYSA-N 0.000 description 1
- MYAHDWOJJFNUFH-UHFFFAOYSA-N 2-(ethylsulfamoyloxy)ethyl n-ethylsulfamate Chemical compound CCNS(=O)(=O)OCCOS(=O)(=O)NCC MYAHDWOJJFNUFH-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 description 1
- MTYMJEFSXKPRAY-UHFFFAOYSA-N 5-sulfamoyloxypentyl sulfamate Chemical compound NS(=O)(=O)OCCCCCOS(N)(=O)=O MTYMJEFSXKPRAY-UHFFFAOYSA-N 0.000 description 1
- GOJJWDOZNKBUSR-UHFFFAOYSA-N 7-sulfamoyloxyheptyl sulfamate Chemical compound NS(=O)(=O)OCCCCCCCOS(N)(=O)=O GOJJWDOZNKBUSR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UFFQSHLYQUQKEM-UHFFFAOYSA-N [2-ethyl-2-(sulfamoyloxymethyl)pentyl] sulfamate Chemical compound NS(=O)(=O)OCC(CC)(CCC)COS(N)(=O)=O UFFQSHLYQUQKEM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 239000000531 antispermatogenic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SQKZZFWTOOPCDQ-UHFFFAOYSA-N dichloromethane;ethyl acetate;hexane Chemical compound ClCCl.CCCCCC.CCOC(C)=O SQKZZFWTOOPCDQ-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000000918 epididymis Anatomy 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012735 histological processing Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- YTJDHKOQYOTSCN-UHFFFAOYSA-N n,n-dibenzylsulfamoyl chloride Chemical compound C=1C=CC=CC=1CN(S(=O)(=O)Cl)CC1=CC=CC=C1 YTJDHKOQYOTSCN-UHFFFAOYSA-N 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- MYCCMUDWFRCSME-UHFFFAOYSA-N n,n-diphenylsulfamoyl chloride Chemical compound C=1C=CC=CC=1N(S(=O)(=O)Cl)C1=CC=CC=C1 MYCCMUDWFRCSME-UHFFFAOYSA-N 0.000 description 1
- FGZSEUXOFDMNEL-UHFFFAOYSA-N n-cyclohexylsulfamoyl chloride Chemical compound ClS(=O)(=O)NC1CCCCC1 FGZSEUXOFDMNEL-UHFFFAOYSA-N 0.000 description 1
- BRLYCKMQJOQWPU-UHFFFAOYSA-N n-cyclopentylsulfamoyl chloride Chemical compound ClS(=O)(=O)NC1CCCC1 BRLYCKMQJOQWPU-UHFFFAOYSA-N 0.000 description 1
- JUDKSMSHAHXBFK-UHFFFAOYSA-N n-ethylsulfamoyl chloride Chemical compound CCNS(Cl)(=O)=O JUDKSMSHAHXBFK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940036051 sojourn Drugs 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011121 vaginal smear Methods 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US537,613 | 1974-12-30 | ||
| US05/537,613 US3997585A (en) | 1974-12-30 | 1974-12-30 | Aliphatic sulfamates |
| US618,998 | 1975-10-02 | ||
| US05/618,998 US4061663A (en) | 1975-10-02 | 1975-10-02 | Process for preparation of aliphatic primary sulfamates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082194A true CA1082194A (en) | 1980-07-22 |
Family
ID=27065556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,484A Expired CA1082194A (en) | 1974-12-30 | 1975-11-12 | Aliphatic sulfamates |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5198217A (sv) |
| AT (1) | AT357998B (sv) |
| CA (1) | CA1082194A (sv) |
| CH (1) | CH617184A5 (sv) |
| DE (1) | DE2559210A1 (sv) |
| DK (1) | DK579975A (sv) |
| FR (1) | FR2296410A1 (sv) |
| GB (1) | GB1524727A (sv) |
| NL (1) | NL7514794A (sv) |
| NO (1) | NO141607C (sv) |
| SE (1) | SE7514459L (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT94305B (pt) * | 1989-06-12 | 1997-02-28 | Robins Co Inc A H | Processo para a preparacao de compostos tendo um ou mais radicais aminossulfoniloxi uteis como produtos farmaceuticos |
| US5194446A (en) * | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| US5273993A (en) * | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| US6011024A (en) | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| US6476011B1 (en) | 1991-08-28 | 2002-11-05 | Sterix Limited | Methods for introducing an estrogenic compound |
| US6903084B2 (en) | 1991-08-29 | 2005-06-07 | Sterix Limited | Steroid sulphatase inhibitors |
| EP0801642B1 (en) * | 1995-11-02 | 2000-12-20 | Yukong Limited | Novel sulfamate compound containing n-substituted carbamoyl group and method for preparing the same |
| KR970027051A (ko) * | 1995-11-02 | 1997-06-24 | 조규향 | 카바모일기를 포함하는 신규한 설파메이트 화합물 |
| US7335650B2 (en) | 2000-01-14 | 2008-02-26 | Sterix Limited | Composition |
-
1975
- 1975-11-12 CA CA239,484A patent/CA1082194A/en not_active Expired
- 1975-11-27 NO NO754009A patent/NO141607C/no unknown
- 1975-11-27 GB GB48763/75A patent/GB1524727A/en not_active Expired
- 1975-12-04 CH CH1580475A patent/CH617184A5/de not_active IP Right Cessation
- 1975-12-16 FR FR7538528A patent/FR2296410A1/fr active Granted
- 1975-12-18 NL NL7514794A patent/NL7514794A/xx unknown
- 1975-12-19 DK DK579975A patent/DK579975A/da unknown
- 1975-12-19 SE SE7514459A patent/SE7514459L/sv unknown
- 1975-12-23 JP JP50152961A patent/JPS5198217A/ja active Pending
- 1975-12-29 AT AT986175A patent/AT357998B/de not_active IP Right Cessation
- 1975-12-30 DE DE19752559210 patent/DE2559210A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2559210A1 (de) | 1976-07-01 |
| FR2296410A1 (fr) | 1976-07-30 |
| NO141607C (no) | 1980-04-09 |
| SE7514459L (sv) | 1976-07-01 |
| GB1524727A (en) | 1978-09-13 |
| NO141607B (no) | 1980-01-02 |
| FR2296410B1 (sv) | 1979-09-21 |
| CH617184A5 (en) | 1980-05-14 |
| ATA986175A (de) | 1980-01-15 |
| NL7514794A (nl) | 1976-07-02 |
| JPS5198217A (sv) | 1976-08-30 |
| NO754009L (sv) | 1976-07-01 |
| DK579975A (da) | 1976-07-01 |
| AT357998B (de) | 1980-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |