IL120056A - Naphthalene derivatives - Google Patents
Naphthalene derivativesInfo
- Publication number
- IL120056A IL120056A IL120056A IL12005693A IL120056A IL 120056 A IL120056 A IL 120056A IL 120056 A IL120056 A IL 120056A IL 12005693 A IL12005693 A IL 12005693A IL 120056 A IL120056 A IL 120056A
- Authority
- IL
- Israel
- Prior art keywords
- mixture
- ch3o
- bis
- give
- group
- Prior art date
Links
- 150000002790 naphthalenes Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 abstract description 2
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 87
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 229960001701 chloroform Drugs 0.000 description 35
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- -1 benzaldehyde compound Chemical class 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 3
- QVUVEEKONLXEOI-UHFFFAOYSA-N 1-bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzene Chemical compound COC(OC)C1=CC(OC)=C(OC)C=C1Br QVUVEEKONLXEOI-UHFFFAOYSA-N 0.000 description 2
- SZCAORBAQHOJQI-UHFFFAOYSA-N 1-iodo-2-methoxyethane Chemical compound COCCI SZCAORBAQHOJQI-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- BXKJSYCGIVLVLA-UHFFFAOYSA-N [2-(dimethoxymethyl)-5,6-dimethoxy-3-pyridin-4-ylphenyl]methanol Chemical compound COC(OC)C1=C(CO)C(OC)=C(OC)C=C1C1=CC=NC=C1 BXKJSYCGIVLVLA-UHFFFAOYSA-N 0.000 description 2
- JFVBCOPZIGRGOL-UHFFFAOYSA-N [3-(acetyloxymethyl)-6,7-dimethoxy-4-(6-methoxypyridin-3-yl)naphthalen-2-yl]methyl acetate Chemical compound C1=NC(OC)=CC=C1C1=C(COC(C)=O)C(COC(C)=O)=CC2=CC(OC)=C(OC)C=C12 JFVBCOPZIGRGOL-UHFFFAOYSA-N 0.000 description 2
- QQOFKDUCHCDOBV-UHFFFAOYSA-N [3-(acetyloxymethyl)-6,7-dimethoxy-4-methylnaphthalen-2-yl]methyl acetate Chemical compound CC(=O)OCC1=C(COC(C)=O)C(C)=C2C=C(OC)C(OC)=CC2=C1 QQOFKDUCHCDOBV-UHFFFAOYSA-N 0.000 description 2
- UNAPDUHNRLGSII-UHFFFAOYSA-N [3-(acetyloxymethyl)-6,7-dimethoxy-4-pyridin-4-ylnaphthalen-2-yl]methyl acetate Chemical compound C=12C=C(OC)C(OC)=CC2=CC(COC(C)=O)=C(COC(C)=O)C=1C1=CC=NC=C1 UNAPDUHNRLGSII-UHFFFAOYSA-N 0.000 description 2
- OQKWJBOBNOGLIJ-UHFFFAOYSA-N [6,7-diethoxy-3-(hydroxymethyl)-4-pyridin-4-ylnaphthalen-2-yl]methanol Chemical compound C=12C=C(OCC)C(OCC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC=C1 OQKWJBOBNOGLIJ-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000001088 anti-asthma Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- SQTHNXSOZXQVPF-UHFFFAOYSA-N dimethyl 6,7-dimethoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=CC2=CC(OC)=C(OC)C=C2C=1C1=CC=NC=C1 SQTHNXSOZXQVPF-UHFFFAOYSA-N 0.000 description 2
- JWFKPRAZXUWSQL-UHFFFAOYSA-N dimethyl 6-hydroxy-7-methoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=CC2=CC(O)=C(OC)C=C2C=1C1=CC=NC=C1 JWFKPRAZXUWSQL-UHFFFAOYSA-N 0.000 description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ABUFDGVEWUKKEY-UHFFFAOYSA-N ethyl 4-[2,3-bis(acetyloxymethyl)-6,7-dimethoxynaphthalen-1-yl]-4-oxobutanoate Chemical compound COC1=C(OC)C=C2C(C(=O)CCC(=O)OCC)=C(COC(C)=O)C(COC(C)=O)=CC2=C1 ABUFDGVEWUKKEY-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- BZMMRNKDONDVIB-UHFFFAOYSA-N (1-ethoxycyclopropyl)oxy-trimethylsilane Chemical compound CCOC1(O[Si](C)(C)C)CC1 BZMMRNKDONDVIB-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- PQQJWADWGSSDBO-UHFFFAOYSA-N (6,7-dimethoxynaphthalen-1-yl)methanol Chemical compound C1=CC(CO)=C2C=C(OC)C(OC)=CC2=C1 PQQJWADWGSSDBO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OJZJNCRFBUXQPP-UHFFFAOYSA-N 1-(4-pyridyl)- 2,3-bis(methoxycarbonyl)-6,7-dimethoxy-1,4-epoxy-1,4-dihydronaphthalene Chemical compound O1C(C=2C3=CC(OC)=C(OC)C=2)C(C(=O)OC)=C(C(=O)OC)C31C1=CC=NC=C1 OJZJNCRFBUXQPP-UHFFFAOYSA-N 0.000 description 1
- IEVDXKDUXWWZLS-UHFFFAOYSA-N 1-[2-(dimethoxymethyl)-4,5-dimethoxyphenyl]ethanol Chemical compound COC(OC)C1=CC(OC)=C(OC)C=C1C(C)O IEVDXKDUXWWZLS-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- ZIUSUDLSXJPGTD-UHFFFAOYSA-N 2,2-dimethylpropyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(C)(C)C)C=C1 ZIUSUDLSXJPGTD-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- BUIQRTDBPCHRIR-UHFFFAOYSA-L O[Cr](Cl)(=O)=O Chemical compound O[Cr](Cl)(=O)=O BUIQRTDBPCHRIR-UHFFFAOYSA-L 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- YSDZPEBAAAEVID-UHFFFAOYSA-N [3-(2,2-dimethylpropoxymethyl)-6,7-dimethoxy-1-pyridin-3-ylnaphthalen-2-yl]methanol Chemical compound C=12C=C(OC)C(OC)=CC2=CC(COCC(C)(C)C)=C(CO)C=1C1=CC=CN=C1 YSDZPEBAAAEVID-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- NRVDARSFEJNIGI-UHFFFAOYSA-N [3-(acetyloxymethyl)-4-formyl-6,7-dimethoxynaphthalen-2-yl]methyl acetate Chemical compound CC(=O)OCC1=C(COC(C)=O)C(C=O)=C2C=C(OC)C(OC)=CC2=C1 NRVDARSFEJNIGI-UHFFFAOYSA-N 0.000 description 1
- OGZPWRXOTKJAQX-UHFFFAOYSA-N [3-(acetyloxymethyl)-6,7-dimethoxy-4-(2-methoxypyridin-4-yl)naphthalen-2-yl]methyl acetate Chemical compound C1=NC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3C=C(COC(C)=O)C=2COC(C)=O)=C1 OGZPWRXOTKJAQX-UHFFFAOYSA-N 0.000 description 1
- GJZINVKEOAVOSP-UHFFFAOYSA-N [3-(hydroxymethyl)-6,7-dimethoxy-4-(6-methoxypyridin-3-yl)naphthalen-2-yl]methanol Chemical compound C1=NC(OC)=CC=C1C1=C(CO)C(CO)=CC2=CC(OC)=C(OC)C=C12 GJZINVKEOAVOSP-UHFFFAOYSA-N 0.000 description 1
- KMRVDAQOCUXESC-UHFFFAOYSA-N [3-(hydroxymethyl)-6,7-dimethoxy-4-methylnaphthalen-2-yl]methanol Chemical compound OCC1=C(CO)C(C)=C2C=C(OC)C(OC)=CC2=C1 KMRVDAQOCUXESC-UHFFFAOYSA-N 0.000 description 1
- LMVXJSQKOVPOSJ-UHFFFAOYSA-N [3-(hydroxymethyl)-6,7-dimethoxy-4-pyridin-3-ylnaphthalen-2-yl]methanol Chemical compound C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C1=CC=CN=C1 LMVXJSQKOVPOSJ-UHFFFAOYSA-N 0.000 description 1
- XQDTWCZBLBRQHO-UHFFFAOYSA-N [3-(hydroxymethyl)-6,7-dimethoxy-4-pyridin-4-ylnaphthalen-2-yl]methanol Chemical compound C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC=C1 XQDTWCZBLBRQHO-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- GEILZOBXTCOHHM-UHFFFAOYSA-N dimethyl 6,7-diethoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound C=12C=C(OCC)C(OCC)=CC2=CC(C(=O)OC)=C(C(=O)OC)C=1C1=CC=NC=C1 GEILZOBXTCOHHM-UHFFFAOYSA-N 0.000 description 1
- XGIYVMYUYNETRI-UHFFFAOYSA-N dimethyl 7-methoxy-6-(2-methoxyethoxy)-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound C=12C=C(OC)C(OCCOC)=CC2=CC(C(=O)OC)=C(C(=O)OC)C=1C1=CC=NC=C1 XGIYVMYUYNETRI-UHFFFAOYSA-N 0.000 description 1
- FEDHHVOFCYIGEO-UHFFFAOYSA-N dimethyl 7-methoxy-6-phenylmethoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound COC=1C=C2C(C=3C=CN=CC=3)=C(C(=O)OC)C(C(=O)OC)=CC2=CC=1OCC1=CC=CC=C1 FEDHHVOFCYIGEO-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VHCAWYMPXNGBTH-UHFFFAOYSA-N methyl 6,7-dimethoxynaphthalene-1-carboxylate Chemical compound COC(=O)C1=CC=CC2=CC(=C(C=C12)OC)OC VHCAWYMPXNGBTH-UHFFFAOYSA-N 0.000 description 1
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4085118A JP3042156B2 (ja) | 1992-02-20 | 1992-02-20 | ナフタレン誘導体、その製法及びその合成中間体 |
| IL104773A IL104773A (en) | 1992-02-20 | 1993-02-18 | Naphthalene derivatives, their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL120056A true IL120056A (en) | 1998-02-08 |
Family
ID=13849719
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL120056A IL120056A (en) | 1992-02-20 | 1993-02-18 | Naphthalene derivatives |
| IL104773A IL104773A (en) | 1992-02-20 | 1993-02-18 | Naphthalene derivatives, their preparation and pharmaceutical compositions containing them |
| IL12005797A IL120057A0 (en) | 1992-02-20 | 1997-01-23 | Naphthalene derivatives |
| IL12005697A IL120056A0 (en) | 1992-02-20 | 1997-01-23 | Naphthalene derivatives |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL104773A IL104773A (en) | 1992-02-20 | 1993-02-18 | Naphthalene derivatives, their preparation and pharmaceutical compositions containing them |
| IL12005797A IL120057A0 (en) | 1992-02-20 | 1997-01-23 | Naphthalene derivatives |
| IL12005697A IL120056A0 (en) | 1992-02-20 | 1997-01-23 | Naphthalene derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5342941A (de) |
| EP (1) | EP0557016B1 (de) |
| JP (1) | JP3042156B2 (de) |
| KR (1) | KR100199121B1 (de) |
| CN (1) | CN1045435C (de) |
| AT (1) | ATE139528T1 (de) |
| AU (1) | AU658046B2 (de) |
| CA (1) | CA2089906C (de) |
| DE (1) | DE69303191T2 (de) |
| DK (1) | DK0557016T3 (de) |
| ES (1) | ES2090855T3 (de) |
| FI (1) | FI102277B1 (de) |
| GR (1) | GR3020294T3 (de) |
| HK (1) | HK98997A (de) |
| IL (4) | IL120056A (de) |
| MY (1) | MY108891A (de) |
| TW (1) | TW224458B (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL118469A (en) * | 1995-06-15 | 2000-08-13 | Tanabe Seiyaku Co | Naphthalene derivatives their preparation and intermediates thereof |
| ID19155A (id) * | 1996-12-13 | 1998-06-18 | Tanabe Seiyaku Co | Turunan-turunan piridin, pembuatannya dan intermediet untuk pembuatannya |
| DE19755480A1 (de) * | 1997-12-13 | 1999-06-24 | Gruenenthal Gmbh | Substituierte heterocyclische Benzocycloalkene und ihre Verwendung als analgetisch wirksame Substanzen |
| JPH11209350A (ja) | 1998-01-26 | 1999-08-03 | Eisai Co Ltd | 含窒素複素環誘導体およびその医薬 |
| US6465495B1 (en) * | 1998-07-30 | 2002-10-15 | Osi Pharmaceuticals, Inc. | Preparation of pyridone-based phosphotyrosine mimetics and uses thereof |
| CA2715683A1 (en) | 1999-08-21 | 2001-03-01 | Nycomed Gmbh | Synergistic combination |
| EP1389468A4 (de) * | 2001-05-23 | 2007-01-10 | Tanabe Seiyaku Co | Zusammensetzungen zur förderung der knochenfrakturheilung |
| CN1537018A (zh) | 2001-05-23 | 2004-10-13 | 田边制药株式会社 | 一种用于软骨疾病再生治疗的组合物 |
| TWI221838B (en) * | 2001-08-09 | 2004-10-11 | Tanabe Seiyaku Co | Pyrazinoisoquinoline compound or naphthalene compound |
| US7153824B2 (en) | 2003-04-01 | 2006-12-26 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| TWI339578B (en) * | 2004-10-29 | 2011-04-01 | Mitsubishi Tanabe Pharma Corp | Use of a pyridine compound for the preparation of a medicament for the treatment of skin lesions |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| WO2007112347A1 (en) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| SI2203439T1 (sl) | 2007-09-14 | 2011-05-31 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni |
| EP2344470B1 (de) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexylderivate als modulatoren von metabotropen glutamatrezeptoren |
| JP5690277B2 (ja) | 2008-11-28 | 2015-03-25 | ジャンセン ファーマシューティカルズ, インコーポレイテッド. | 代謝型グルタミン酸受容体の調節因子としてのインドールおよびベンゾオキサジン誘導体 |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| MX386697B (es) | 2014-01-21 | 2025-03-19 | Janssen Pharmaceutica Nv | Combinaciones que comprenden agonistas ortostericos o moduladores alostericos positivos del receptor glutamatergico metabotropico de subtipo 2 y su uso |
| ME03518B (de) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinationen mit positiven allosterischen modulatoren von metabotropem glutamatergen rezeptor vom subtyp 2 und deren verwendung |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA825413B (en) * | 1981-08-26 | 1983-06-29 | Pfizer | Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them |
| US4503061A (en) * | 1983-07-22 | 1985-03-05 | Warner-Lambert Company | Substituted phenyl-pyridinones as cardiotonic agents |
| US4661596A (en) * | 1985-02-21 | 1987-04-28 | American Home Products Corporation | Quinolinyl (or pyridinyl) methoxy substituted naphthalene compounds as antiallergic agents |
| US4792556A (en) * | 1985-09-09 | 1988-12-20 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
| RU2073673C1 (ru) * | 1987-10-19 | 1997-02-20 | Пфайзер Инк. | Рацемические и оптические активные производные тетралина и 7-гидрокситетралина |
| GB8809481D0 (en) * | 1988-04-21 | 1988-05-25 | Smith Kline French Lab | Chemical compounds |
| DE3837464A1 (de) * | 1988-11-04 | 1990-05-10 | Bayer Ag | (hetero)aryloxynaphthalinderivate, verfahren und neue (hetero)aryloxynaphthylamine zu ihrer herstellung sowie ihre verwendung als herbizide |
| GB8916683D0 (en) * | 1989-07-21 | 1989-09-06 | Beecham Group Plc | Novel compounds |
| US5182296A (en) * | 1989-10-26 | 1993-01-26 | Tanabe Seiyaky Co., Ltd. | Naphthyloxazolidone derivatives |
| AU641769B2 (en) * | 1990-06-18 | 1993-09-30 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| US5272170A (en) * | 1990-12-05 | 1993-12-21 | J. Uriach & Cia., S.A. | Tetralones with pharmacological activity |
| EP0489300A3 (en) * | 1990-12-05 | 1993-03-17 | J. Uriach & Cia. S.A. | New tetralones with pharmacological activity |
| FR2671551B1 (fr) * | 1991-01-15 | 1993-03-12 | Adir | Nouveaux composes de structure aryl triazinique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| RU2059603C1 (ru) * | 1991-05-09 | 1996-05-10 | Хоффманн-Ля Рош АГ | ПРОИЗВОДНЫЕ α -ЗАМЕЩЕННЫХ АРИЛУКСУСНЫХ КИСЛОТ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ |
-
1992
- 1992-02-20 JP JP4085118A patent/JP3042156B2/ja not_active Expired - Lifetime
-
1993
- 1993-02-11 EP EP93300998A patent/EP0557016B1/de not_active Expired - Lifetime
- 1993-02-11 AT AT93300998T patent/ATE139528T1/de not_active IP Right Cessation
- 1993-02-11 DK DK93300998.7T patent/DK0557016T3/da active
- 1993-02-11 AU AU32952/93A patent/AU658046B2/en not_active Ceased
- 1993-02-11 ES ES93300998T patent/ES2090855T3/es not_active Expired - Lifetime
- 1993-02-11 DE DE69303191T patent/DE69303191T2/de not_active Expired - Fee Related
- 1993-02-18 FI FI930711A patent/FI102277B1/fi active
- 1993-02-18 IL IL120056A patent/IL120056A/en not_active IP Right Cessation
- 1993-02-18 KR KR1019930002269A patent/KR100199121B1/ko not_active Expired - Fee Related
- 1993-02-18 IL IL104773A patent/IL104773A/xx not_active IP Right Cessation
- 1993-02-18 TW TW082101129A patent/TW224458B/zh active
- 1993-02-18 MY MYPI93000270A patent/MY108891A/en unknown
- 1993-02-19 CA CA002089906A patent/CA2089906C/en not_active Expired - Fee Related
- 1993-02-19 US US08/019,885 patent/US5342941A/en not_active Expired - Fee Related
- 1993-02-20 CN CN93102013A patent/CN1045435C/zh not_active Expired - Fee Related
-
1996
- 1996-06-20 GR GR960401544T patent/GR3020294T3/el unknown
-
1997
- 1997-01-23 IL IL12005797A patent/IL120057A0/xx unknown
- 1997-01-23 IL IL12005697A patent/IL120056A0/xx unknown
- 1997-06-26 HK HK98997A patent/HK98997A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW224458B (de) | 1994-06-01 |
| FI102277B (fi) | 1998-11-13 |
| AU658046B2 (en) | 1995-03-30 |
| FI102277B1 (fi) | 1998-11-13 |
| CA2089906A1 (en) | 1993-08-21 |
| JPH05229987A (ja) | 1993-09-07 |
| EP0557016B1 (de) | 1996-06-19 |
| AU3295293A (en) | 1993-08-26 |
| DE69303191T2 (de) | 1996-11-14 |
| CA2089906C (en) | 1998-08-18 |
| CN1075957A (zh) | 1993-09-08 |
| GR3020294T3 (en) | 1996-09-30 |
| ATE139528T1 (de) | 1996-07-15 |
| IL104773A0 (en) | 1993-06-10 |
| DE69303191D1 (de) | 1996-07-25 |
| IL120056A0 (en) | 1997-04-15 |
| ES2090855T3 (es) | 1996-10-16 |
| FI930711A0 (fi) | 1993-02-18 |
| EP0557016A1 (de) | 1993-08-25 |
| JP3042156B2 (ja) | 2000-05-15 |
| HK98997A (en) | 1997-08-08 |
| KR930017851A (ko) | 1993-09-20 |
| MY108891A (en) | 1996-11-30 |
| CN1045435C (zh) | 1999-10-06 |
| DK0557016T3 (da) | 1996-07-15 |
| IL104773A (en) | 1997-07-13 |
| KR100199121B1 (ko) | 1999-06-15 |
| IL120057A0 (en) | 1997-04-15 |
| US5342941A (en) | 1994-08-30 |
| FI930711L (fi) | 1993-08-21 |
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| FF | Patent granted | ||
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