NO323095B1 - 3,4-Disubstituerte fenyletanolamintetralinkarboksamidderivater - Google Patents
3,4-Disubstituerte fenyletanolamintetralinkarboksamidderivater Download PDFInfo
- Publication number
- NO323095B1 NO323095B1 NO19983777A NO983777A NO323095B1 NO 323095 B1 NO323095 B1 NO 323095B1 NO 19983777 A NO19983777 A NO 19983777A NO 983777 A NO983777 A NO 983777A NO 323095 B1 NO323095 B1 NO 323095B1
- Authority
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- Norway
- Prior art keywords
- carbon atom
- configuration
- hydroxy
- amino group
- amino
- Prior art date
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- -1 3,4-Disubstituted phenylethanolamine tetralinecarboxamide Chemical class 0.000 title description 30
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 95
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 92
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 206010000242 Abortion threatened Diseases 0.000 claims abstract description 10
- 208000005985 Threatened Abortion Diseases 0.000 claims abstract description 10
- 229940124630 bronchodilator Drugs 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims description 35
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 206010007027 Calculus urinary Diseases 0.000 claims description 10
- 239000004575 stone Substances 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 208000008281 urolithiasis Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 206010043508 Threatened labour Diseases 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 208000000884 Airway Obstruction Diseases 0.000 claims description 3
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000036262 stenosis Effects 0.000 claims description 3
- 208000037804 stenosis Diseases 0.000 claims description 3
- 206010036600 Premature labour Diseases 0.000 claims description 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 4
- 206010000210 abortion Diseases 0.000 claims 1
- 231100000176 abortion Toxicity 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 76
- 150000001875 compounds Chemical class 0.000 abstract description 60
- 230000004936 stimulating effect Effects 0.000 abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 208000005107 Premature Birth Diseases 0.000 abstract 1
- 206010036590 Premature baby Diseases 0.000 abstract 1
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 abstract 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- 201000011086 ureterolithiasis Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 377
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- 239000000243 solution Substances 0.000 description 97
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- 238000005160 1H NMR spectroscopy Methods 0.000 description 64
- 229910001868 water Inorganic materials 0.000 description 52
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 44
- 239000002904 solvent Substances 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 35
- 238000003756 stirring Methods 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 29
- 238000001816 cooling Methods 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000003480 eluent Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 229940113088 dimethylacetamide Drugs 0.000 description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000004811 liquid chromatography Methods 0.000 description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- STZZNMCSJCFKHI-UGKGYDQZSA-N 2-[[(7s)-7-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]-n,n-dimethylacetamide Chemical compound C1([C@@H](O)CN[C@H]2CCC3=CC=C(C=C3C2)OCC(=O)N(C)C)=CC=C(O)C(CO)=C1 STZZNMCSJCFKHI-UGKGYDQZSA-N 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- IALTYGIQQNCQBN-URXFXBBRSA-N 2-[[(7s)-7-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]-1-pyrrolidin-1-ylethanone Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CN[C@@H]2CC3=CC(OCC(=O)N4CCCC4)=CC=C3CC2)=C1 IALTYGIQQNCQBN-URXFXBBRSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000008602 contraction Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- NIPXMZRWJWJPGM-SNVBAGLBSA-N (2r)-2-(2,2-dimethyl-4h-1,3-benzodioxin-6-yl)-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)C1=CC=C2OC(C)(C)OCC2=C1 NIPXMZRWJWJPGM-SNVBAGLBSA-N 0.000 description 4
- SJYXUPGLQCUYJS-UHFFFAOYSA-N 2-bromo-1-(2,2-dimethyl-4h-1,3-benzodioxin-6-yl)ethanone Chemical compound BrCC(=O)C1=CC=C2OC(C)(C)OCC2=C1 SJYXUPGLQCUYJS-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 210000000754 myometrium Anatomy 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- RTCUCQWIICFPOD-SECBINFHSA-N (1r)-1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C([C@H](N)C)=CC=CC2=C1 RTCUCQWIICFPOD-SECBINFHSA-N 0.000 description 3
- QPIOVNJLOVNTMW-UHFFFAOYSA-N 2-bromo-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CBr QPIOVNJLOVNTMW-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
- 101150041968 CDC13 gene Proteins 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000010934 O-alkylation reaction Methods 0.000 description 3
- 208000001871 Tachycardia Diseases 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- 239000002269 analeptic agent Substances 0.000 description 3
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000010575 fractional recrystallization Methods 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
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- 230000002269 spontaneous effect Effects 0.000 description 3
- 230000006794 tachycardia Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- HWTXUWOMIFGPMX-DITALETJSA-N (2s)-2-hydroxy-n-[(2s)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[4-phenylmethoxy-3-(2-phenylmethoxyethyl)phenyl]acetamide Chemical compound C=1C=CC=CC=1COCCC1=CC([C@@H](C(=O)N[C@@H]2CC3=CC(O)=CC=C3CC2)O)=CC=C1OCC1=CC=CC=C1 HWTXUWOMIFGPMX-DITALETJSA-N 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- ZCWQARFFINAXTB-LBPRGKRZSA-N tert-butyl n-[(2s)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1=C(O)C=C2C[C@@H](NC(=O)OC(C)(C)C)CCC2=C1 ZCWQARFFINAXTB-LBPRGKRZSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/08—Bronchodilators
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
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- 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
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- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
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- Organic Chemistry (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
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- Urology & Nephrology (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6888596 | 1996-02-19 | ||
| PCT/JP1997/000424 WO1997030023A1 (fr) | 1996-02-19 | 1997-02-18 | Derives de phenylethanolaminotetralinecarboxamide 3,4-disubstitue |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983777D0 NO983777D0 (no) | 1998-08-18 |
| NO983777L NO983777L (no) | 1998-10-19 |
| NO323095B1 true NO323095B1 (no) | 2007-01-02 |
Family
ID=13386565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983777A NO323095B1 (no) | 1996-02-19 | 1998-08-18 | 3,4-Disubstituerte fenyletanolamintetralinkarboksamidderivater |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6133266A (pt) |
| EP (1) | EP0882704B1 (pt) |
| JP (1) | JP3892045B2 (pt) |
| KR (1) | KR100491633B1 (pt) |
| CN (1) | CN1100032C (pt) |
| AT (1) | ATE225767T1 (pt) |
| AU (1) | AU725042B2 (pt) |
| BR (1) | BR9707566B1 (pt) |
| CA (1) | CA2245490C (pt) |
| CZ (1) | CZ293974B6 (pt) |
| DE (1) | DE69716242T2 (pt) |
| DK (1) | DK0882704T3 (pt) |
| EA (1) | EA002143B1 (pt) |
| ES (1) | ES2184989T3 (pt) |
| HU (1) | HU229400B1 (pt) |
| ID (1) | ID16091A (pt) |
| MY (1) | MY123853A (pt) |
| NO (1) | NO323095B1 (pt) |
| NZ (1) | NZ331445A (pt) |
| PL (1) | PL186411B1 (pt) |
| PT (1) | PT882704E (pt) |
| SG (1) | SG72727A1 (pt) |
| TW (1) | TW375604B (pt) |
| WO (1) | WO1997030023A1 (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999009001A1 (fr) * | 1997-08-19 | 1999-02-25 | Kissei Pharmaceutical Co., Ltd. | Derives de phenylethanolaminotetraline et bronchodilatateurs |
| ZA994264B (en) | 1998-07-01 | 2000-01-25 | Warner Lambert Co | Stereoisomers with high affinity for adrenergic receptors. |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| US7232837B2 (en) | 1999-06-29 | 2007-06-19 | Mcneil-Ppc, Inc. | Stereoisomers with high affinity for adrenergic receptors |
| FR2809725B1 (fr) * | 2000-06-06 | 2004-05-07 | Sanofi Synthelabo | Propanolaminotetralines, leur preparation et compositions pharmaceutiques en contenant |
| GB0029562D0 (en) | 2000-12-04 | 2001-01-17 | Novartis Ag | Organic compounds |
| KR101028496B1 (ko) * | 2003-01-22 | 2011-04-11 | 깃세이 야쿠힌 고교 가부시키가이샤 | 자궁내 태아 발육지연 또는 임신중독증의 예방 또는 치료제 |
| JPWO2006054513A1 (ja) * | 2004-11-19 | 2008-05-29 | キッセイ薬品工業株式会社 | 神経因性疼痛の予防又は治療剤 |
| JPWO2006054514A1 (ja) * | 2004-11-19 | 2008-05-29 | キッセイ薬品工業株式会社 | 神経因性疼痛の予防又は治療用医薬組成物 |
| EP2098511A1 (en) | 2008-03-07 | 2009-09-09 | Solvias AG | Process for preparing compounds containing a hydronaphtalene structure with an unsymmetrically substituted benzene ring |
| CA2781061A1 (en) * | 2009-11-18 | 2011-05-26 | Medicinova, Inc. | Treatment of acute exacerbation of asthma and reduction of likelihood of hospitalization of patients suffering therefrom |
| US20120035265A1 (en) * | 2010-03-08 | 2012-02-09 | Medicinova, Inc. | Compositions, methods, and devices for the treatment of dysmenorrhea |
| BR112012025703A2 (pt) * | 2010-04-08 | 2016-07-05 | Medicinova Inc | métodos e composições para o tratamento de síndrome de intestino irritável |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9107827D0 (en) * | 1991-04-12 | 1991-05-29 | Fujisawa Pharmaceutical Co | New ethanolamine derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| IL104567A (en) * | 1992-02-03 | 1997-03-18 | Fujisawa Pharmaceutical Co | Ethanolamine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| WO1993018007A1 (en) * | 1992-03-13 | 1993-09-16 | Tokyo Tanabe Company Limited | Novel carbostyril derivative |
-
1997
- 1997-02-17 SG SG1997000355A patent/SG72727A1/en unknown
- 1997-02-17 TW TW086102182A patent/TW375604B/zh not_active IP Right Cessation
- 1997-02-18 PT PT97902714T patent/PT882704E/pt unknown
- 1997-02-18 DE DE69716242T patent/DE69716242T2/de not_active Expired - Lifetime
- 1997-02-18 NZ NZ331445A patent/NZ331445A/xx not_active IP Right Cessation
- 1997-02-18 CN CN97193866A patent/CN1100032C/zh not_active Expired - Lifetime
- 1997-02-18 CA CA002245490A patent/CA2245490C/en not_active Expired - Lifetime
- 1997-02-18 MY MYPI97000600A patent/MY123853A/en unknown
- 1997-02-18 CZ CZ19982523A patent/CZ293974B6/cs not_active IP Right Cessation
- 1997-02-18 PL PL97328530A patent/PL186411B1/pl unknown
- 1997-02-18 US US09/125,429 patent/US6133266A/en not_active Expired - Lifetime
- 1997-02-18 DK DK97902714T patent/DK0882704T3/da active
- 1997-02-18 KR KR10-1998-0706378A patent/KR100491633B1/ko not_active IP Right Cessation
- 1997-02-18 WO PCT/JP1997/000424 patent/WO1997030023A1/ja active IP Right Grant
- 1997-02-18 EA EA199800644A patent/EA002143B1/ru not_active IP Right Cessation
- 1997-02-18 ES ES97902714T patent/ES2184989T3/es not_active Expired - Lifetime
- 1997-02-18 AU AU20014/97A patent/AU725042B2/en not_active Expired
- 1997-02-18 HU HU9900621A patent/HU229400B1/hu unknown
- 1997-02-18 EP EP97902714A patent/EP0882704B1/en not_active Expired - Lifetime
- 1997-02-18 AT AT97902714T patent/ATE225767T1/de active
- 1997-02-18 JP JP52920097A patent/JP3892045B2/ja not_active Expired - Lifetime
- 1997-02-18 BR BRPI9707566-3A patent/BR9707566B1/pt not_active IP Right Cessation
- 1997-02-19 ID IDP970478A patent/ID16091A/id unknown
-
1998
- 1998-08-18 NO NO19983777A patent/NO323095B1/no not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |