SK6222003A3 - Naphthalene derivatives, process for their preparation and their use in pharmaceutical compositions - Google Patents
Naphthalene derivatives, process for their preparation and their use in pharmaceutical compositions Download PDFInfo
- Publication number
- SK6222003A3 SK6222003A3 SK622-2003A SK6222003A SK6222003A3 SK 6222003 A3 SK6222003 A3 SK 6222003A3 SK 6222003 A SK6222003 A SK 6222003A SK 6222003 A3 SK6222003 A3 SK 6222003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- carbon atoms
- hydrogen
- naphthyl
- alkyl
- mmol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000002790 naphthalenes Chemical class 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 189
- 150000001875 compounds Chemical class 0.000 claims description 91
- 125000001624 naphthyl group Chemical group 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 10
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims description 9
- 108050007331 Cannabinoid receptor Proteins 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000027455 binding Effects 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000006806 disease prevention Effects 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000004760 Tenosynovitis Diseases 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940121376 cannabinoid receptor agonist Drugs 0.000 abstract description 3
- 239000003537 cannabinoid receptor agonist Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 78
- 239000000243 solution Substances 0.000 description 78
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- 235000019341 magnesium sulphate Nutrition 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000002500 ions Chemical class 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- 239000000284 extract Substances 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229930003827 cannabinoid Natural products 0.000 description 9
- 239000003557 cannabinoid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 239000002027 dichloromethane extract Substances 0.000 description 8
- 239000002024 ethyl acetate extract Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 7
- 125000002757 morpholinyl group Chemical group 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- MWDDULCMFVSEEX-UHFFFAOYSA-N 1-iodo-4-pentoxynaphthalene Chemical compound C1=CC=C2C(OCCCCC)=CC=C(I)C2=C1 MWDDULCMFVSEEX-UHFFFAOYSA-N 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 230000007306 turnover Effects 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 208000004454 Hyperalgesia Diseases 0.000 description 5
- 101150003085 Pdcl gene Proteins 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 5
- 235000019345 sodium thiosulphate Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- YIQPLIQXWUJYTO-UHFFFAOYSA-N 4-pentoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OCCCCC)=CC=C(C=O)C2=C1 YIQPLIQXWUJYTO-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- 208000035154 Hyperesthesia Diseases 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000003447 ipsilateral effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 4
- 208000004296 neuralgia Diseases 0.000 description 4
- 208000021722 neuropathic pain Diseases 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- OYXUGKNLJGYJRR-UHFFFAOYSA-N 1-naphthalen-1-ylsulfanyl-4-pentoxynaphthalene Chemical compound C12=CC=CC=C2C(OCCCCC)=CC=C1SC1=CC=CC2=CC=CC=C12 OYXUGKNLJGYJRR-UHFFFAOYSA-N 0.000 description 3
- LYVSDOLBBDJEMK-UHFFFAOYSA-N 3-pentoxybenzene-1,2-diamine Chemical compound CCCCCOC1=CC=CC(N)=C1N LYVSDOLBBDJEMK-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- JIOPJAHYUCTWNP-UHFFFAOYSA-N 4-pentoxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(OCCCCC)=CC=C(C(O)=O)C2=C1 JIOPJAHYUCTWNP-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 206010065390 Inflammatory pain Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- IWGGTBYTGVLEET-UHFFFAOYSA-N [8-(naphthalene-1-carbonyl)-5-pentoxynaphthalen-2-yl] trifluoromethanesulfonate Chemical compound C12=CC(OS(=O)(=O)C(F)(F)F)=CC=C2C(OCCCCC)=CC=C1C(=O)C1=CC=CC2=CC=CC=C12 IWGGTBYTGVLEET-UHFFFAOYSA-N 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- MNZMFKCQTRWMLC-UHFFFAOYSA-N n-(2-acetamido-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(O)=C1NC(C)=O MNZMFKCQTRWMLC-UHFFFAOYSA-N 0.000 description 3
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- JGOFIIZNFBCVAV-UHFFFAOYSA-N periodic acid;hydrate Chemical compound O.OI(=O)(=O)=O JGOFIIZNFBCVAV-UHFFFAOYSA-N 0.000 description 3
- 125000005936 piperidyl group Chemical group 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- LEAHQNMVEGMQAX-UHFFFAOYSA-N (2-acetamido-3-nitrophenyl) acetate Chemical compound CC(=O)NC1=C(OC(C)=O)C=CC=C1[N+]([O-])=O LEAHQNMVEGMQAX-UHFFFAOYSA-N 0.000 description 2
- YQRWCMPNLITCAP-UHFFFAOYSA-N (5-pentoxynaphthalen-2-yl) acetate Chemical compound CC(=O)OC1=CC=C2C(OCCCCC)=CC=CC2=C1 YQRWCMPNLITCAP-UHFFFAOYSA-N 0.000 description 2
- RPGJSOFRWXGECY-UHFFFAOYSA-N (7-hydroxy-4-pentoxynaphthalen-1-yl)-naphthalen-1-ylmethanone Chemical compound C12=CC(O)=CC=C2C(OCCCCC)=CC=C1C(=O)C1=CC=CC2=CC=CC=C12 RPGJSOFRWXGECY-UHFFFAOYSA-N 0.000 description 2
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/304—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Surgery (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0028702.9A GB0028702D0 (en) | 2000-11-24 | 2000-11-24 | Organic compounds |
PCT/EP2001/013605 WO2002042248A2 (en) | 2000-11-24 | 2001-11-22 | Naphthalene derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
SK6222003A3 true SK6222003A3 (en) | 2003-10-07 |
Family
ID=9903825
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK622-2003A SK6222003A3 (en) | 2000-11-24 | 2001-11-22 | Naphthalene derivatives, process for their preparation and their use in pharmaceutical compositions |
Country Status (27)
Country | Link |
---|---|
US (1) | US7045533B2 (de) |
EP (2) | EP2338886A3 (de) |
JP (2) | JP4836396B2 (de) |
KR (1) | KR100810948B1 (de) |
CN (1) | CN1224598C (de) |
AR (1) | AR035505A1 (de) |
AT (1) | ATE540013T1 (de) |
AU (1) | AU2002226350A1 (de) |
BR (1) | BR0115605A (de) |
CA (1) | CA2427844C (de) |
CZ (1) | CZ20031424A3 (de) |
EC (1) | ECSP034574A (de) |
ES (1) | ES2378881T3 (de) |
GB (1) | GB0028702D0 (de) |
HU (1) | HUP0302125A3 (de) |
IL (1) | IL155235A0 (de) |
MX (1) | MXPA03004593A (de) |
MY (1) | MY129613A (de) |
NO (1) | NO330005B1 (de) |
NZ (1) | NZ548553A (de) |
PE (1) | PE20020532A1 (de) |
PT (1) | PT1339663E (de) |
RU (1) | RU2354646C2 (de) |
SK (1) | SK6222003A3 (de) |
TW (1) | TWI314140B (de) |
WO (1) | WO2002042248A2 (de) |
ZA (1) | ZA200302916B (de) |
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GB0028702D0 (en) * | 2000-11-24 | 2001-01-10 | Novartis Ag | Organic compounds |
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US7067539B2 (en) * | 2001-02-08 | 2006-06-27 | Schering Corporation | Cannabinoid receptor ligands |
EP2130820A1 (de) | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antipruriginosa |
AU2003250117B2 (en) * | 2002-07-29 | 2007-05-10 | F. Hoffmann-La Roche Ag | Novel benzodioxoles |
AU2003278929A1 (en) * | 2002-10-18 | 2004-05-13 | Amylin Pharmaceuticals, Inc. | Treatment of pancreatitis with amylin |
WO2004052846A1 (en) * | 2002-12-06 | 2004-06-24 | Bayer Healthcare Ag | Tetrahydro-naphthalene derivatives |
DK1572632T3 (da) * | 2002-12-09 | 2008-10-27 | Xention Ltd | Tetrahydro-naphthalenderivater som vanilloidreceptorantagonister |
AR043633A1 (es) | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
NZ542491A (en) | 2003-03-28 | 2009-04-30 | Janssen Pharmaceutica Nv | Benzo[1,2,5]thiadiazole compounds as CCK2 modulators |
SG146624A1 (en) | 2003-09-11 | 2008-10-30 | Kemia Inc | Cytokine inhibitors |
SE0303490D0 (sv) * | 2003-12-19 | 2003-12-19 | Astrazeneca Ab | New use V |
GB0504950D0 (en) * | 2005-03-10 | 2005-04-20 | Novartis Ag | Organic compositions |
WO2007045593A2 (en) * | 2005-10-18 | 2007-04-26 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Naphthyl derivatives as inhibitors of beta-amyloid aggregation |
GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
IE20070928A1 (en) * | 2007-12-21 | 2009-09-30 | Giuliani Int Ltd | Multi target ligands |
BRPI0907805A2 (pt) * | 2008-02-28 | 2015-07-14 | Novartis Ag | Combinações para tratar dor associada à hiv |
KR101294872B1 (ko) * | 2008-09-04 | 2013-08-08 | 아디아 바이오사이언스즈 인크. | 요산 수치를 조절하기 위한 화합물, 조성물 및 이들의 사용 방법 |
JP5164755B2 (ja) * | 2008-09-09 | 2013-03-21 | キヤノン株式会社 | ビス−アセチルアミノフェニル化合物の結晶の製造方法 |
BRPI0921038A2 (pt) * | 2008-11-17 | 2019-09-24 | Hoffmann La Roche | ácido naftilacéticos |
US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
DK2522658T3 (en) | 2010-01-04 | 2018-11-19 | Nippon Soda Co | NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND AGRICULTURAL / Horticulture Bactericidal Agents |
AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
AR080055A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de pirazolo-[5,1-b]-oxazol como antagonistas de los receptores de crf -1 |
EP2531490B1 (de) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexylamidderivate als crf-rezeptorantagonisten |
WO2012090179A2 (en) | 2010-12-30 | 2012-07-05 | Lupin Limited | Isoquinoline derivatives as cannabinoid receptor modulators |
WO2012090177A2 (en) | 2010-12-30 | 2012-07-05 | Lupin Limited | Cannabinoid receptor modulators |
AR086411A1 (es) | 2011-05-20 | 2013-12-11 | Nippon Soda Co | Compuesto heterociclico conteniendo nitrogeno y fungicida para el uso en agricultura y jardineria |
US8546416B2 (en) | 2011-05-27 | 2013-10-01 | Novartis Ag | 3-spirocyclic piperidine derivatives as ghrelin receptor agonists |
WO2013005168A2 (en) | 2011-07-05 | 2013-01-10 | Lupin Limited | Cannabinoid receptor modulators |
EP2852591A1 (de) | 2012-05-03 | 2015-04-01 | Novartis AG | L-malatsalz aus 2,7-diaza-spiro[4.5]dec-7-yl-derivaten und kristalline formen davon als ghrelin-rezeptoragonisten |
GB2532990A (en) | 2014-12-05 | 2016-06-08 | Schlumberger Holdings | Corrosion inhibition |
GB2543498A (en) | 2015-10-19 | 2017-04-26 | Schlumberger Holdings | Corrosion inhibition |
WO2017103932A1 (en) | 2015-12-17 | 2017-06-22 | Biokine Therapeutics Ltd. | Small molecules for inhibiting chemokine activity, a kinase activity and/or cancer cells growth |
WO2017103931A1 (en) * | 2015-12-17 | 2017-06-22 | Biokine Therapeutics Ltd. | Small molecules against cancer |
CN109316479B (zh) * | 2018-10-22 | 2023-09-05 | 河南省锐达医药科技有限公司 | 一种萘酚类化合物的制备及其在癌症治疗方面的应用 |
RU2684117C1 (ru) * | 2018-10-29 | 2019-04-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный химико-фармацевтический университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФУ Минздрава России) | Способ получения N-(нафталин-2-ил)бензамидина |
RU2694263C1 (ru) * | 2019-02-14 | 2019-07-11 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный химико-фармацевтический университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФУ Минздрава России) | Анальгезирующее и противовоспалительное средство с противомикробной активностью |
BR112021022775A2 (pt) | 2019-05-15 | 2022-02-01 | Alonbio Ltd | Moléculas pequenas para tratamento do câncer, inibição da atividade da quimiocina e/ou indução da morte celular |
JP7158028B2 (ja) | 2019-07-09 | 2022-10-21 | タカラベルモント株式会社 | 頭部載置具および椅子 |
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FR1110460A (fr) * | 1954-09-03 | 1956-02-13 | Cfmc | Nouveaux colorants azoïques, complexes métallifères en dérivant et produits intermédiaires utilisables pour leur préparation |
DE1016717B (de) | 1956-04-30 | 1957-10-03 | Kalle & Co Ag | Verfahren zur Herstellung aromatischer Amine mit sekundaerer Aminogruppe |
CH505152A (de) | 1968-11-21 | 1971-03-31 | Shell Int Research | Verfahren zur Herstellung von Phosphonsäureestern, Phosphinsäureestern bzw. Phosphinoxiden |
US3932381A (en) * | 1973-02-12 | 1976-01-13 | Eastman Kodak Company | Magenta image-providing phenylazo-naphthyl dyes |
US4067903A (en) * | 1975-10-04 | 1978-01-10 | Basf Aktiengesellschaft | Manufacture of arylamines |
EP0264883A3 (de) * | 1986-10-21 | 1990-04-04 | Banyu Pharmaceutical Co., Ltd. | Substituierte Pyridinderivate |
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US5679866A (en) * | 1995-01-20 | 1997-10-21 | American Cyanamid Company | Fungicidal methods, compounds and compositions containing benzophenones |
US6090850A (en) * | 1996-02-05 | 2000-07-18 | Eli Lilly And Company | Naphthyl glyoxamides as SPLA2 inhibitors |
KR100539030B1 (ko) * | 1996-08-12 | 2005-12-27 | 셀진 코포레이션 | 면역치료제 및 이를 이용하여 사이토카인 농도를 감소시키는 방법 |
PT966436E (pt) | 1997-02-21 | 2003-03-31 | Bayer Ag | Arilsulfonamidas e analogos e sua aplicacao para o tratamento de doencas neurodegenerativas |
FR2760744B1 (fr) * | 1997-03-12 | 1999-04-23 | Rhodia Chimie Sa | Procede d'acylation d'un compose aromatique |
US5945567A (en) * | 1997-08-20 | 1999-08-31 | American Cyanamid Company | Fungicidal 2-methoxybenzophenones |
US5939429A (en) * | 1997-09-30 | 1999-08-17 | Virginia Commonwealth University | Cardiovascular uses of cannabinoid compounds |
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GB0028702D0 (en) * | 2000-11-24 | 2001-01-10 | Novartis Ag | Organic compounds |
-
2000
- 2000-11-24 GB GBGB0028702.9A patent/GB0028702D0/en not_active Ceased
-
2001
- 2001-11-20 TW TW090128718A patent/TWI314140B/zh active
- 2001-11-21 MY MYPI20015337A patent/MY129613A/en unknown
- 2001-11-22 AT AT01995657T patent/ATE540013T1/de active
- 2001-11-22 CZ CZ20031424A patent/CZ20031424A3/cs unknown
- 2001-11-22 HU HU0302125A patent/HUP0302125A3/hu unknown
- 2001-11-22 ES ES01995657T patent/ES2378881T3/es not_active Expired - Lifetime
- 2001-11-22 PT PT01995657T patent/PT1339663E/pt unknown
- 2001-11-22 CA CA2427844A patent/CA2427844C/en not_active Expired - Fee Related
- 2001-11-22 US US10/432,120 patent/US7045533B2/en not_active Expired - Fee Related
- 2001-11-22 PE PE2001001166A patent/PE20020532A1/es not_active Application Discontinuation
- 2001-11-22 CN CNB018194389A patent/CN1224598C/zh not_active Expired - Fee Related
- 2001-11-22 AU AU2002226350A patent/AU2002226350A1/en not_active Abandoned
- 2001-11-22 EP EP10175729.2A patent/EP2338886A3/de not_active Withdrawn
- 2001-11-22 NZ NZ548553A patent/NZ548553A/en unknown
- 2001-11-22 RU RU2003117459/04A patent/RU2354646C2/ru not_active IP Right Cessation
- 2001-11-22 JP JP2002544387A patent/JP4836396B2/ja not_active Expired - Fee Related
- 2001-11-22 AR ARP010105448A patent/AR035505A1/es not_active Application Discontinuation
- 2001-11-22 WO PCT/EP2001/013605 patent/WO2002042248A2/en not_active Application Discontinuation
- 2001-11-22 EP EP01995657A patent/EP1339663B1/de not_active Expired - Lifetime
- 2001-11-22 IL IL15523501A patent/IL155235A0/xx not_active IP Right Cessation
- 2001-11-22 KR KR1020037005038A patent/KR100810948B1/ko not_active IP Right Cessation
- 2001-11-22 SK SK622-2003A patent/SK6222003A3/sk not_active Application Discontinuation
- 2001-11-22 MX MXPA03004593A patent/MXPA03004593A/es active IP Right Grant
- 2001-11-22 BR BR0115605-5A patent/BR0115605A/pt active Search and Examination
-
2003
- 2003-04-11 ZA ZA200302916A patent/ZA200302916B/en unknown
- 2003-04-29 EC EC2003004574A patent/ECSP034574A/es unknown
- 2003-05-22 NO NO20032327A patent/NO330005B1/no not_active IP Right Cessation
-
2007
- 2007-09-12 JP JP2007236718A patent/JP2008050361A/ja active Pending
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