JPS6322565A - アルド−スレダクタ−ゼ抑制剤として有用なナフタレニルスルホニルイミダゾリジンジオンおよびそのチオキソ類似体 - Google Patents
アルド−スレダクタ−ゼ抑制剤として有用なナフタレニルスルホニルイミダゾリジンジオンおよびそのチオキソ類似体Info
- Publication number
- JPS6322565A JPS6322565A JP16513387A JP16513387A JPS6322565A JP S6322565 A JPS6322565 A JP S6322565A JP 16513387 A JP16513387 A JP 16513387A JP 16513387 A JP16513387 A JP 16513387A JP S6322565 A JPS6322565 A JP S6322565A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- sulfonyl
- naphthalenyl
- pharmaceutically acceptable
- 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.)
- Granted
Links
- XXBCGNGNWXBWNF-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)CN1S(=O)(=O)C1=CC=CC2=CC=CC=C12 XXBCGNGNWXBWNF-UHFFFAOYSA-N 0.000 title claims description 10
- 239000003288 aldose reductase inhibitor Substances 0.000 title description 4
- 229940118148 Aldose reductase inhibitor Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- -1 1-naphthalenyl Chemical group 0.000 claims description 29
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000004471 Glycine Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- LKSCCJOAZVHTSI-UHFFFAOYSA-N 1-(5-bromonaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C1=CC=C2C(Br)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=O LKSCCJOAZVHTSI-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 6
- 208000002177 Cataract Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 208000017169 kidney disease Diseases 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- DDMKOOIEEMCYNU-UHFFFAOYSA-N 1-(5-bromonaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC=C2C(Br)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=S DDMKOOIEEMCYNU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229940091173 hydantoin Drugs 0.000 claims description 3
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 3
- ORIPQEPCUIXFLF-UHFFFAOYSA-N 1-(4-bromonaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C12=CC=CC=C2C(Br)=CC=C1S(=O)(=O)N1CC(=O)NC1=S ORIPQEPCUIXFLF-UHFFFAOYSA-N 0.000 claims description 2
- PNFXFYFDDHVEJU-UHFFFAOYSA-N 1-(4-bromonaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C12=CC=CC=C2C(Br)=CC=C1S(=O)(=O)N1CC(=O)NC1=O PNFXFYFDDHVEJU-UHFFFAOYSA-N 0.000 claims description 2
- SCNCUTACGKEKPD-UHFFFAOYSA-N 1-(5-chloronaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=S SCNCUTACGKEKPD-UHFFFAOYSA-N 0.000 claims description 2
- RBTADHXQJPDFSG-UHFFFAOYSA-N 1-(5-iodonaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC=C2C(I)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=S RBTADHXQJPDFSG-UHFFFAOYSA-N 0.000 claims description 2
- MKCHDBWAFIFTBP-UHFFFAOYSA-N 1-(6-bromonaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C=1C=CC2=CC(Br)=CC=C2C=1S(=O)(=O)N1CC(=O)NC1=S MKCHDBWAFIFTBP-UHFFFAOYSA-N 0.000 claims description 2
- HCALBSLLLSXZHA-UHFFFAOYSA-N 1-(6-bromonaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C=1C=CC2=CC(Br)=CC=C2C=1S(=O)(=O)N1CC(=O)NC1=O HCALBSLLLSXZHA-UHFFFAOYSA-N 0.000 claims description 2
- AHGPCMBRIKAFKS-UHFFFAOYSA-N 1-(7-bromonaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C12=CC(Br)=CC=C2C=CC=C1S(=O)(=O)N1CC(=O)NC1=O AHGPCMBRIKAFKS-UHFFFAOYSA-N 0.000 claims description 2
- YYGSFNZDIIWREH-UHFFFAOYSA-N 1-[5-(dimethylamino)naphthalen-1-yl]sulfonylimidazolidine-2,4-dione Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=O YYGSFNZDIIWREH-UHFFFAOYSA-N 0.000 claims description 2
- RPLHEUGLBDRYCP-UHFFFAOYSA-N 1-[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]sulfonylimidazolidine-2,4-dione Chemical compound C=1C=CC2=C(C(F)(F)F)C(OC)=CC=C2C=1S(=O)(=O)N1CC(=O)NC1=O RPLHEUGLBDRYCP-UHFFFAOYSA-N 0.000 claims description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 8
- GSXYJNYJROKCIA-UHFFFAOYSA-N 1-(5-chloronaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=O GSXYJNYJROKCIA-UHFFFAOYSA-N 0.000 claims 1
- WAPHMSYETXSYFZ-UHFFFAOYSA-N 1-(5-iodonaphthalen-1-yl)sulfonylimidazolidine-2,4-dione Chemical compound C1=CC=C2C(I)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=O WAPHMSYETXSYFZ-UHFFFAOYSA-N 0.000 claims 1
- GGNDMFKILVVRFG-UHFFFAOYSA-N 1-(7-bromonaphthalen-1-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C12=CC(Br)=CC=C2C=CC=C1S(=O)(=O)N1CC(=O)NC1=S GGNDMFKILVVRFG-UHFFFAOYSA-N 0.000 claims 1
- WPYAOQAKGUWFKG-UHFFFAOYSA-N 1-[5-(dimethylamino)naphthalen-1-yl]sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)N1CC(=O)NC1=S WPYAOQAKGUWFKG-UHFFFAOYSA-N 0.000 claims 1
- KZZRQUFDHHFMET-UHFFFAOYSA-N 1-[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C=1C=CC2=C(C(F)(F)F)C(OC)=CC=C2C=1S(=O)(=O)N1CC(=O)NC1=S KZZRQUFDHHFMET-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002927 oxygen compounds Chemical group 0.000 claims 1
- 239000007787 solid Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 125000000464 thioxo group Chemical group S=* 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229930182830 galactose Natural products 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 210000000695 crystalline len Anatomy 0.000 description 6
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 6
- 102000016912 Aldehyde Reductase Human genes 0.000 description 5
- 108010053754 Aldehyde reductase Proteins 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 102000004877 Insulin Human genes 0.000 description 5
- 108090001061 Insulin Proteins 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 229940125396 insulin Drugs 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- 239000003538 oral antidiabetic agent Substances 0.000 description 4
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000001508 eye Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
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- 210000003497 sciatic nerve Anatomy 0.000 description 3
- DBCQNYRXPSAMGR-UHFFFAOYSA-N 1-(5-bromonaphthalen-2-yl)sulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound C=1C=C2C(Br)=CC=CC2=CC=1S(=O)(=O)N1CC(=O)NC1=S DBCQNYRXPSAMGR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- 239000003889 eye drop Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- WVKIFIROCHIWAY-UHFFFAOYSA-N hydron;2-(methylamino)acetic acid;chloride Chemical compound Cl.CNCC(O)=O WVKIFIROCHIWAY-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000008101 lactose 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- KQBHRQXHIZZHTO-UHFFFAOYSA-N 1-(5-bromonaphthalen-2-yl)sulfonylimidazolidine-2,4-dione Chemical compound C=1C=C2C(Br)=CC=CC2=CC=1S(=O)(=O)N1CC(=O)NC1=O KQBHRQXHIZZHTO-UHFFFAOYSA-N 0.000 description 1
- TYAVGKKQMQCEOW-UHFFFAOYSA-N 1-(benzenesulfonyl)imidazolidine-2,4-dione Chemical compound O=C1NC(=O)CN1S(=O)(=O)C1=CC=CC=C1 TYAVGKKQMQCEOW-UHFFFAOYSA-N 0.000 description 1
- LPSPZMPOYCAXAQ-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1NC(=O)CN1S(=O)(=O)C1=CC=CC2=CC=CC=C12 LPSPZMPOYCAXAQ-UHFFFAOYSA-N 0.000 description 1
- BJMRFOZZBBPXTL-UHFFFAOYSA-N 2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]acetamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCC(N)=O BJMRFOZZBBPXTL-UHFFFAOYSA-N 0.000 description 1
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 1
- WOUMHLGSMDVJHS-UHFFFAOYSA-L 3-benzyl-1-[6-(3-benzyl-1-azoniabicyclo[2.2.2]octan-1-yl)hexyl]-1-azoniabicyclo[2.2.2]octane;dichloride Chemical compound [Cl-].[Cl-].C1CC(C(CC=2C=CC=CC=2)C2)CC[N+]12CCCCCC[N+](CC1)(C2)CCC1C2CC1=CC=CC=C1 WOUMHLGSMDVJHS-UHFFFAOYSA-L 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- ORZVZEAGJANKBV-UHFFFAOYSA-N 5-sulfonylimidazolidine-2,4-dione Chemical class O=C1NC(=O)C(=S(=O)=O)N1 ORZVZEAGJANKBV-UHFFFAOYSA-N 0.000 description 1
- KVDCTYOFKIXXRQ-UHFFFAOYSA-N 6-methoxy-5-(trifluoromethyl)naphthalene-1-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 KVDCTYOFKIXXRQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- 101100129500 Caenorhabditis elegans max-2 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 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
- 241000270322 Lepidosauria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 150000007982 azolidines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical group OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 210000004283 incisor Anatomy 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88137786A | 1986-07-02 | 1986-07-02 | |
| US881377 | 1986-07-02 | ||
| US012592 | 1996-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6322565A true JPS6322565A (ja) | 1988-01-30 |
| JPH05390B2 JPH05390B2 (enrdf_load_stackoverflow) | 1993-01-05 |
Family
ID=25378357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16513387A Granted JPS6322565A (ja) | 1986-07-02 | 1987-06-30 | アルド−スレダクタ−ゼ抑制剤として有用なナフタレニルスルホニルイミダゾリジンジオンおよびそのチオキソ類似体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6322565A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6461465A (en) * | 1987-08-28 | 1989-03-08 | Mochida Pharm Co Ltd | Hydantoin derivative and medicine composition containing said derivative as active ingredient |
| JPH02201405A (ja) * | 1989-01-31 | 1990-08-09 | Mitsubishi Electric Corp | 光受信器 |
| JPH03294270A (ja) * | 1990-02-23 | 1991-12-25 | Mochida Pharmaceut Co Ltd | ヒダントイン誘導体を有効成分として含有する血糖低下剤 |
| WO1997002033A1 (fr) * | 1995-06-30 | 1997-01-23 | Mochida Pharmaceutical Co., Ltd. | Agent uricosurique |
| US6257772B1 (en) | 1998-09-18 | 2001-07-10 | Sumitomo Electric Industries, Ltd. | Photodiode module |
| JP2008534600A (ja) * | 2005-03-31 | 2008-08-28 | タケダ サン ディエゴ インコーポレイテッド | ヒドロキシステロイドデヒドロゲナーゼ阻害剤 |
-
1987
- 1987-06-30 JP JP16513387A patent/JPS6322565A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6461465A (en) * | 1987-08-28 | 1989-03-08 | Mochida Pharm Co Ltd | Hydantoin derivative and medicine composition containing said derivative as active ingredient |
| JPH02201405A (ja) * | 1989-01-31 | 1990-08-09 | Mitsubishi Electric Corp | 光受信器 |
| JPH03294270A (ja) * | 1990-02-23 | 1991-12-25 | Mochida Pharmaceut Co Ltd | ヒダントイン誘導体を有効成分として含有する血糖低下剤 |
| WO1997002033A1 (fr) * | 1995-06-30 | 1997-01-23 | Mochida Pharmaceutical Co., Ltd. | Agent uricosurique |
| US6257772B1 (en) | 1998-09-18 | 2001-07-10 | Sumitomo Electric Industries, Ltd. | Photodiode module |
| JP2008534600A (ja) * | 2005-03-31 | 2008-08-28 | タケダ サン ディエゴ インコーポレイテッド | ヒドロキシステロイドデヒドロゲナーゼ阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05390B2 (enrdf_load_stackoverflow) | 1993-01-05 |
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