KR20010013435A - 5-나프탈렌-1-일-1,3-디옥산 유도체, 제조 및 치료에의 이용 - Google Patents
5-나프탈렌-1-일-1,3-디옥산 유도체, 제조 및 치료에의 이용 Download PDFInfo
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- KR20010013435A KR20010013435A KR1019997011436A KR19997011436A KR20010013435A KR 20010013435 A KR20010013435 A KR 20010013435A KR 1019997011436 A KR1019997011436 A KR 1019997011436A KR 19997011436 A KR19997011436 A KR 19997011436A KR 20010013435 A KR20010013435 A KR 20010013435A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- naphthyl
- mmol
- mixture
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 5
- 230000001225 therapeutic effect Effects 0.000 title description 2
- XOGDPHJIDASIIN-UHFFFAOYSA-N 5-naphthalen-1-yl-1,3-dioxane Chemical class C1OCOCC1C1=CC=CC2=CC=CC=C12 XOGDPHJIDASIIN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- -1 carbamoylmethyl group Chemical group 0.000 claims abstract description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 99
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 7
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 5
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 abstract description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005936 piperidyl group Chemical group 0.000 abstract description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- 239000002585 base Substances 0.000 description 35
- 239000002904 solvent Substances 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000012074 organic phase Substances 0.000 description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000004587 chromatography analysis Methods 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- NFIRKFSLLJQYOU-UHFFFAOYSA-N 2-(6-methoxynaphthalen-1-yl)propane-1,3-diol Chemical compound OCC(CO)C1=CC=CC2=CC(OC)=CC=C21 NFIRKFSLLJQYOU-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- BPYUAAOXJAQFAX-UHFFFAOYSA-N 3-[5-(6-methoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1COC(CCCN)OC1 BPYUAAOXJAQFAX-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000004083 survival effect Effects 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000003880 polar aprotic solvent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- YRJFIPOBFIVAMZ-UHFFFAOYSA-N 2-(3-chloropropyl)-5-(6-methoxynaphthalen-1-yl)-1,3-dioxane Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1COC(CCCCl)OC1 YRJFIPOBFIVAMZ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- PIJTUMKXURFRNN-UHFFFAOYSA-N n-[3-[5-(6-hydroxynaphthalen-1-yl)-1,3-dioxan-2-yl]propyl]acetamide Chemical compound C1OC(CCCNC(=O)C)OCC1C1=CC=CC2=CC(O)=CC=C12 PIJTUMKXURFRNN-UHFFFAOYSA-N 0.000 description 3
- UYUKFWIZNMAUGJ-UHFFFAOYSA-N n-benzyl-3-[5-(6-ethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C=1C=CC2=CC(OCC)=CC=C2C=1C(CO1)COC1CCCNCC1=CC=CC=C1 UYUKFWIZNMAUGJ-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000004454 trace mineral analysis Methods 0.000 description 3
- ZBPUNVFDQXYNDY-UHFFFAOYSA-N 2-(3-chloropropyl)-1,3-dioxolane Chemical compound ClCCCC1OCCO1 ZBPUNVFDQXYNDY-UHFFFAOYSA-N 0.000 description 2
- PKWMVBFCENMPAX-UHFFFAOYSA-N 2-[benzyl-[3-[5-(6-ethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propyl]amino]-n-methylacetamide Chemical compound C=1C=CC2=CC(OCC)=CC=C2C=1C(CO1)COC1CCCN(CC(=O)NC)CC1=CC=CC=C1 PKWMVBFCENMPAX-UHFFFAOYSA-N 0.000 description 2
- ZPWIVSGEQGESFF-UHFFFAOYSA-N 2-chloro-n-cyclopropylacetamide Chemical compound ClCC(=O)NC1CC1 ZPWIVSGEQGESFF-UHFFFAOYSA-N 0.000 description 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 2
- PNJIPDXXCQOOSH-UHFFFAOYSA-N 3-[5-(6-cyclopentyloxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC1C1=CC=CC2=CC(OC3CCCC3)=CC=C12 PNJIPDXXCQOOSH-UHFFFAOYSA-N 0.000 description 2
- HSJRHEJARVCXML-UHFFFAOYSA-N 3-[5-(6-ethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C=1C=CC2=CC(OCC)=CC=C2C=1C1COC(CCCN)OC1 HSJRHEJARVCXML-UHFFFAOYSA-N 0.000 description 2
- WECALDNBKFZUTK-UHFFFAOYSA-N 3-[5-(6-methoxynaphthalen-1-yl)-1,3-dioxan-2-yl]-N-(pyridin-4-ylmethyl)propan-1-amine dihydrochloride Chemical compound Cl.Cl.COC=1C=C2C=CC=C(C2=CC1)C1COC(OC1)CCCNCC1=CC=NC=C1 WECALDNBKFZUTK-UHFFFAOYSA-N 0.000 description 2
- LOYYGCWIHQRWDO-UHFFFAOYSA-N 3-[5-(6-methoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC2=CC(OC)=CC=C2C=1C1COC(CCCN)OC1 LOYYGCWIHQRWDO-UHFFFAOYSA-N 0.000 description 2
- KFTMOGJEMZLSSC-UHFFFAOYSA-N 3-[5-(6-phenylmethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC1C1=CC=CC2=CC(OCC=3C=CC=CC=3)=CC=C12 KFTMOGJEMZLSSC-UHFFFAOYSA-N 0.000 description 2
- NSWOVINHJOWXGP-UHFFFAOYSA-N 3-[5-[6-(cyclopropylmethoxy)naphthalen-1-yl]-1,3-dioxan-2-yl]-n-methylpropan-1-amine Chemical compound C1OC(CCCNC)OCC1C1=CC=CC2=CC(OCC3CC3)=CC=C12 NSWOVINHJOWXGP-UHFFFAOYSA-N 0.000 description 2
- UNYHXFFPECOORM-UHFFFAOYSA-N C(C(=O)O)(=O)O.COC=1C=C2C=CC=C(C2=CC1)C1COC(OC1)CCCN1CC2=CC=CC=C2CC1C(=O)NC Chemical compound C(C(=O)O)(=O)O.COC=1C=C2C=CC=C(C2=CC1)C1COC(OC1)CCCN1CC2=CC=CC=C2CC1C(=O)NC UNYHXFFPECOORM-UHFFFAOYSA-N 0.000 description 2
- OETOPRBCQIWRGH-UHFFFAOYSA-N C1(CCCC1)OC=1C=C2C=CC=C(C2=CC1)C1COC(OC1)CCCNCC1=CC=CC=C1 Chemical compound C1(CCCC1)OC=1C=C2C=CC=C(C2=CC1)C1COC(OC1)CCCNCC1=CC=CC=C1 OETOPRBCQIWRGH-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 208000010496 Heart Arrest Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010038669 Respiratory arrest Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- TUDDIIVOPGBKNO-UHFFFAOYSA-N n-[3-[5-(6-ethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propyl]acetamide Chemical compound C=1C=CC2=CC(OCC)=CC=C2C=1C1COC(CCCNC(C)=O)OC1 TUDDIIVOPGBKNO-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/06944 | 1997-06-05 | ||
| FR97/06947 | 1997-06-05 | ||
| FR9706944A FR2764287B1 (fr) | 1997-06-05 | 1997-06-05 | Derives de 5-naphtalen-1-yl-1,3-dioxanes, leur preparation et leur application en therapeutique |
| FR97/06946 | 1997-06-05 | ||
| FR9706947A FR2764291B1 (fr) | 1997-06-05 | 1997-06-05 | Derives de 5-naphtalen-1-yl-1,3-dioxane, leur preparation et leur application en therapeutique |
| FR9706945A FR2764288B1 (fr) | 1997-06-05 | 1997-06-05 | Derives de 5-naphtalen-1-yl-1,3-dioxane, leur preparation et leur application en therapeutique |
| FR97/06945 | 1997-06-05 | ||
| FR9706946A FR2764289B1 (fr) | 1997-06-05 | 1997-06-05 | Derives de 5-naphtalen-1-yl-1,3-dioxane, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010013435A true KR20010013435A (ko) | 2001-02-26 |
Family
ID=27447000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997011436A KR20010013435A (ko) | 1997-06-05 | 1998-06-03 | 5-나프탈렌-1-일-1,3-디옥산 유도체, 제조 및 치료에의 이용 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0986552A1 (es) |
| JP (1) | JP2002502412A (es) |
| KR (1) | KR20010013435A (es) |
| CN (1) | CN1265658A (es) |
| AR (1) | AR012908A1 (es) |
| AU (1) | AU8025198A (es) |
| BG (1) | BG103937A (es) |
| BR (1) | BR9810742A (es) |
| CA (1) | CA2290695A1 (es) |
| CO (1) | CO4940480A1 (es) |
| EE (1) | EE9900560A (es) |
| HU (1) | HUP0002166A3 (es) |
| IL (1) | IL133242A0 (es) |
| NO (1) | NO995966L (es) |
| PL (1) | PL337234A1 (es) |
| SK (1) | SK166199A3 (es) |
| TR (1) | TR199903022T2 (es) |
| WO (1) | WO1998055474A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100792814B1 (ko) * | 2000-07-21 | 2008-01-14 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 신경병증 통증 및 군발성 및 편두통성 두통-관련 통증의예방 또는 치료를 위해 사용하기 위한 카바메이트 화합물 |
| FR2843964B1 (fr) | 2002-08-29 | 2004-10-01 | Sanofi Synthelabo | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0461958T3 (da) * | 1990-06-15 | 1995-02-20 | Synthelabo | 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanderivater, fremgangsmåde til fremstilling deraf og anvendelse deraf i terapien |
| FR2714055B1 (fr) * | 1993-12-22 | 1996-01-19 | Synthelabo | Dérivés de 5-(arylalkyl)-1,3-dioxane substitués en position 2, leur préparation et leur utilisation en thérapeutique. |
| FR2742152B1 (fr) * | 1995-12-06 | 1998-01-16 | Synthelabo | Derives de 5-naphtalen-1-yl-1,3-dioxanes, leur preparation et leur application en therapeutique |
-
1998
- 1998-06-03 CN CN98807817A patent/CN1265658A/zh active Pending
- 1998-06-03 AR ARP980102585A patent/AR012908A1/es unknown
- 1998-06-03 BR BR9810742-9A patent/BR9810742A/pt not_active IP Right Cessation
- 1998-06-03 EP EP98928419A patent/EP0986552A1/fr not_active Withdrawn
- 1998-06-03 HU HU0002166A patent/HUP0002166A3/hu unknown
- 1998-06-03 KR KR1019997011436A patent/KR20010013435A/ko not_active Application Discontinuation
- 1998-06-03 EE EEP199900560A patent/EE9900560A/xx unknown
- 1998-06-03 IL IL13324298A patent/IL133242A0/xx unknown
- 1998-06-03 AU AU80251/98A patent/AU8025198A/en not_active Abandoned
- 1998-06-03 TR TR1999/03022T patent/TR199903022T2/xx unknown
- 1998-06-03 SK SK1661-99A patent/SK166199A3/sk unknown
- 1998-06-03 PL PL98337234A patent/PL337234A1/xx unknown
- 1998-06-03 JP JP50172399A patent/JP2002502412A/ja active Pending
- 1998-06-03 WO PCT/FR1998/001113 patent/WO1998055474A1/fr not_active Application Discontinuation
- 1998-06-03 CA CA002290695A patent/CA2290695A1/en not_active Abandoned
- 1998-06-04 CO CO98031750A patent/CO4940480A1/es unknown
-
1999
- 1999-11-30 BG BG103937A patent/BG103937A/xx unknown
- 1999-12-03 NO NO995966A patent/NO995966L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BG103937A (en) | 2000-07-31 |
| NO995966D0 (no) | 1999-12-03 |
| HUP0002166A2 (hu) | 2001-06-28 |
| BR9810742A (pt) | 2000-09-12 |
| SK166199A3 (en) | 2000-06-12 |
| CO4940480A1 (es) | 2000-07-24 |
| IL133242A0 (en) | 2001-03-19 |
| AR012908A1 (es) | 2000-11-22 |
| EE9900560A (et) | 2000-06-15 |
| CA2290695A1 (en) | 1998-12-10 |
| NO995966L (no) | 2000-02-04 |
| PL337234A1 (en) | 2000-08-14 |
| HUP0002166A3 (en) | 2002-12-28 |
| EP0986552A1 (fr) | 2000-03-22 |
| WO1998055474A1 (fr) | 1998-12-10 |
| JP2002502412A (ja) | 2002-01-22 |
| CN1265658A (zh) | 2000-09-06 |
| AU8025198A (en) | 1998-12-21 |
| TR199903022T2 (xx) | 2000-04-21 |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |