SE503805C2 - N-Derivat av (fenyletyl-beta-ol)amin, ett förfarande för deras framställning och läkemedelskompositioner som innehåller desamma - Google Patents
N-Derivat av (fenyletyl-beta-ol)amin, ett förfarande för deras framställning och läkemedelskompositioner som innehåller desammaInfo
- Publication number
- SE503805C2 SE503805C2 SE9302437A SE9302437A SE503805C2 SE 503805 C2 SE503805 C2 SE 503805C2 SE 9302437 A SE9302437 A SE 9302437A SE 9302437 A SE9302437 A SE 9302437A SE 503805 C2 SE503805 C2 SE 503805C2
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- trans
- cis
- tetrahydrofuran
- acoet
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims description 20
- 150000001412 amines Chemical class 0.000 title claims description 9
- 239000003814 drug Substances 0.000 title claims description 3
- 229940079593 drug Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 222
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006264 debenzylation reaction Methods 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 150000003939 benzylamines Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 172
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 130
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- -1 hydrochloric Chemical class 0.000 description 57
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 54
- 238000004809 thin layer chromatography Methods 0.000 description 53
- 238000005160 1H NMR spectroscopy Methods 0.000 description 45
- 229910052739 hydrogen Inorganic materials 0.000 description 44
- 239000003480 eluent Substances 0.000 description 37
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 35
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 23
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 239000012071 phase Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000001530 fumaric acid Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229910010084 LiAlH4 Inorganic materials 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 229910052754 neon Inorganic materials 0.000 description 4
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 4
- 229960002052 salbutamol Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 3
- 230000007885 bronchoconstriction Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- YRPHNSODVHXAOP-UHFFFAOYSA-N methyl 5-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C(=O)CBr)=CC=C1O YRPHNSODVHXAOP-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- WPVNVXPMXNQMOM-UHFFFAOYSA-N (2-ethyloxolan-2-yl)methanamine Chemical compound CCC1(CN)CCCO1 WPVNVXPMXNQMOM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- QRDAPCMJAOQZSU-KQQUZDAGSA-N (e)-3-[4-[(e)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(\C=C\C(=O)NO)N(C)C=C1\C=C\C(=O)C1=CC=CC(F)=C1 QRDAPCMJAOQZSU-KQQUZDAGSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- RZFJBSIAXYEPBX-UHFFFAOYSA-N 1-[4-[4-[2-[4-chloro-3-(diethylsulfamoyl)anilino]pyrimidin-4-yl]pyridin-2-yl]phenyl]-3-methylurea Chemical compound C1=C(Cl)C(S(=O)(=O)N(CC)CC)=CC(NC=2N=C(C=CN=2)C=2C=C(N=CC=2)C=2C=CC(NC(=O)NC)=CC=2)=C1 RZFJBSIAXYEPBX-UHFFFAOYSA-N 0.000 description 1
- ZCOIVJPCZLPQPT-UHFFFAOYSA-N 2-(oxolan-2-yl)ethanamine Chemical compound NCCC1CCCO1 ZCOIVJPCZLPQPT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- SGTKOERNGLWTLL-UHFFFAOYSA-N 4-(3,4,5-trimethoxyphenyl)pent-4-en-1-ol Chemical compound COC1=CC(=CC(OC)=C1OC)C(=C)CCCO SGTKOERNGLWTLL-UHFFFAOYSA-N 0.000 description 1
- JPIXESQNIOPGAQ-UHFFFAOYSA-N 4-(3,4,5-trimethoxyphenyl)pentanal Chemical compound COC=1C=C(C=C(C1OC)OC)C(C)CCC=O JPIXESQNIOPGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- FNBUZGRPJLEIMO-UHFFFAOYSA-N 5-[2-[5-chloro-2-[(5-ethoxyquinolin-8-yl)sulfonylamino]phenyl]ethynyl]-4-methoxypyridine-2-carboxylic acid Chemical compound ClC=1C=CC(=C(C=1)C#CC=1C(=CC(=NC=1)C(=O)O)OC)NS(=O)(=O)C=1C=CC(=C2C=CC=NC=12)OCC FNBUZGRPJLEIMO-UHFFFAOYSA-N 0.000 description 1
- NHCIXEPZNPKEAR-UHFFFAOYSA-N 6-(oxan-2-yloxy)hexan-1-ol Chemical compound OCCCCCCOC1CCCCO1 NHCIXEPZNPKEAR-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- FRRBOHVBOXCURC-UHFFFAOYSA-N [5-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)oxolan-2-yl]methanol Chemical compound C1=C(S(C)(=O)=O)C(OCCC)=C(OC)C=C1C1OC(CO)CC1 FRRBOHVBOXCURC-UHFFFAOYSA-N 0.000 description 1
- QABUURICQJOWID-MRXNPFEDSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[(2r)-2-ethylpiperidin-1-yl]methanone Chemical compound CC[C@@H]1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 QABUURICQJOWID-MRXNPFEDSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 101150108018 arv1 gene Proteins 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 description 1
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- PSEHHVRCDVOTID-VMAIWCPRSA-N chloro-bis[(1r,3r,4s,5r)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane Chemical compound C([C@H]([C@@H]1C)B(Cl)[C@H]2[C@H](C)[C@]3(C[C@@](C2)(C3(C)C)[H])[H])[C@@]2([H])C(C)(C)[C@]1([H])C2 PSEHHVRCDVOTID-VMAIWCPRSA-N 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126126 compound 18n Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000009518 sodium iodide 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229960004298 vecuronium bromide Drugs 0.000 description 1
- VEPSYABRBFXYIB-PWXDFCLTSA-M vecuronium bromide Chemical compound [Br-].N1([C@@H]2[C@@H](OC(C)=O)C[C@@H]3CC[C@H]4[C@@H]5C[C@@H]([C@@H]([C@]5(CC[C@@H]4[C@@]3(C)C2)C)OC(=O)C)[N+]2(C)CCCCC2)CCCCC1 VEPSYABRBFXYIB-PWXDFCLTSA-M 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929215274A GB9215274D0 (en) | 1992-07-17 | 1992-07-17 | Derivatives of(phenylethyl-beta-ol)amine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9302437D0 SE9302437D0 (sv) | 1993-07-16 |
| SE9302437L SE9302437L (sv) | 1994-01-18 |
| SE503805C2 true SE503805C2 (sv) | 1996-09-09 |
Family
ID=10718914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9302437A SE503805C2 (sv) | 1992-07-17 | 1993-07-16 | N-Derivat av (fenyletyl-beta-ol)amin, ett förfarande för deras framställning och läkemedelskompositioner som innehåller desamma |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5447942A (el) |
| JP (1) | JP3204811B2 (el) |
| AT (1) | AT403693B (el) |
| AU (1) | AU672791B2 (el) |
| BE (1) | BE1006429A3 (el) |
| CA (1) | CA2100381C (el) |
| CH (1) | CH687705A5 (el) |
| DE (1) | DE4323976C2 (el) |
| DK (1) | DK84793A (el) |
| DZ (1) | DZ1704A1 (el) |
| ES (1) | ES2067417B1 (el) |
| FI (1) | FI933235A (el) |
| FR (2) | FR2693653B1 (el) |
| GB (2) | GB9215274D0 (el) |
| GR (1) | GR1001565B (el) |
| HK (1) | HK52596A (el) |
| HU (1) | HUT64757A (el) |
| IE (1) | IE73266B1 (el) |
| IN (1) | IN183086B (el) |
| LU (1) | LU88383A1 (el) |
| MA (1) | MA22937A1 (el) |
| MY (1) | MY109395A (el) |
| NL (1) | NL9301241A (el) |
| NO (1) | NO302946B1 (el) |
| NZ (1) | NZ248041A (el) |
| OA (1) | OA09838A (el) |
| PL (1) | PL173783B1 (el) |
| PT (1) | PT101308B (el) |
| RU (1) | RU2060252C1 (el) |
| SE (1) | SE503805C2 (el) |
| TN (1) | TNSN93081A1 (el) |
| ZA (1) | ZA934667B (el) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006025920A2 (en) * | 2004-06-19 | 2006-03-09 | Human Biomolecular Research Institute | Modulators of central nervous system neurotransmitters |
| WO2020148325A1 (en) | 2019-01-15 | 2020-07-23 | Phenex-Fxr Gmbh | Neutral lxr modulators |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700692A (en) | 1971-06-04 | 1972-10-24 | Colgate Palmolive Co | 1-(4{40 -hydroxy-3{40 -(hydroxy methyl)-phenyl)-1-hydroxy-2-aralkylaminoethanes |
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| NZ211822A (en) * | 1984-04-17 | 1988-11-29 | Glaxo Group Ltd | Phenethanolamine derivatives and pharmaceutical compositions |
| DE3731198A1 (de) * | 1987-02-07 | 1988-08-18 | Bayer Ag | 2-aminomethyltetrahydrofurane |
| EP0286242A3 (en) * | 1987-03-12 | 1989-08-09 | Glaxo Group Limited | Ethanolamine derivates, processes for their preparation and pharmaceutical compositions containing them |
| GB2230525A (en) * | 1989-04-14 | 1990-10-24 | Glaxo Group Ltd | 1-(Hydroxyphenyl)-2-aminoethanol derivatives |
| GB2230775A (en) * | 1989-04-24 | 1990-10-31 | Glaxo Group Ltd | Phenethanolamine compounds |
| TW209832B (el) * | 1989-10-10 | 1993-07-21 | Glaxo Group Ltd |
-
1992
- 1992-07-17 GB GB929215274A patent/GB9215274D0/en active Pending
-
1993
- 1993-06-24 IE IE930472A patent/IE73266B1/en not_active IP Right Cessation
- 1993-06-25 GR GR930100276A patent/GR1001565B/el not_active IP Right Cessation
- 1993-06-29 NO NO932383A patent/NO302946B1/no unknown
- 1993-06-29 ZA ZA934667A patent/ZA934667B/xx unknown
- 1993-06-30 IN IN678DE1993 patent/IN183086B/en unknown
- 1993-07-01 NZ NZ248041A patent/NZ248041A/xx unknown
- 1993-07-06 MY MYPI93001317A patent/MY109395A/en unknown
- 1993-07-09 FR FR9308453A patent/FR2693653B1/fr not_active Expired - Fee Related
- 1993-07-09 BE BE9300712A patent/BE1006429A3/fr not_active IP Right Cessation
- 1993-07-09 CH CH02076/93A patent/CH687705A5/fr not_active IP Right Cessation
- 1993-07-09 FR FR9308452A patent/FR2693723B1/fr not_active Expired - Fee Related
- 1993-07-12 DZ DZ930084A patent/DZ1704A1/fr active
- 1993-07-13 CA CA002100381A patent/CA2100381C/en not_active Expired - Fee Related
- 1993-07-13 US US08/091,589 patent/US5447942A/en not_active Expired - Lifetime
- 1993-07-15 NL NL9301241A patent/NL9301241A/nl not_active Application Discontinuation
- 1993-07-15 GB GB9314718A patent/GB2268742B/en not_active Expired - Fee Related
- 1993-07-15 PL PL93299693A patent/PL173783B1/pl unknown
- 1993-07-15 PT PT101308A patent/PT101308B/pt not_active IP Right Cessation
- 1993-07-15 LU LU88383A patent/LU88383A1/fr unknown
- 1993-07-16 RU RU9393046412A patent/RU2060252C1/ru active
- 1993-07-16 JP JP17693293A patent/JP3204811B2/ja not_active Expired - Fee Related
- 1993-07-16 OA OA60392A patent/OA09838A/fr unknown
- 1993-07-16 DE DE4323976A patent/DE4323976C2/de not_active Expired - Fee Related
- 1993-07-16 FI FI933235A patent/FI933235A/fi unknown
- 1993-07-16 SE SE9302437A patent/SE503805C2/sv not_active IP Right Cessation
- 1993-07-16 TN TNTNSN93081A patent/TNSN93081A1/fr unknown
- 1993-07-16 ES ES09301603A patent/ES2067417B1/es not_active Expired - Fee Related
- 1993-07-16 AU AU42042/93A patent/AU672791B2/en not_active Ceased
- 1993-07-16 DK DK084793A patent/DK84793A/da not_active Application Discontinuation
- 1993-07-16 HU HU9302057A patent/HUT64757A/hu unknown
- 1993-07-16 MA MA23237A patent/MA22937A1/fr unknown
- 1993-07-19 AT AT0142793A patent/AT403693B/de not_active IP Right Cessation
-
1996
- 1996-03-28 HK HK52596A patent/HK52596A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1286682C (en) | (3s,4s)-7-hydroxy-___-tetra-hydrocannabinol homologes and derivatives | |
| US4356313A (en) | [(5,6,9a-substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoic and cycloalkanoic acid esters and their analogs, the parent acids and their salts | |
| Erhardt et al. | Ultra-short-acting. beta.-adrenergic receptor blocking agents. 1.(Aryloxy) propanolamines containing esters in the nitrogen substituent | |
| US4356314A (en) | [5,6,9A-Substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoic and cycloalkanoic acids, their analogs, esters, salts, and derivatives | |
| HU194858B (en) | Process for producing dibenzo/b,d/pirane derivatives and pharmaceutical compositions containing them | |
| Tanikaga et al. | Stereochemical behavior of intermediary compounds in the amine-catalyzed Knoevenagel reaction. | |
| US20240132482A1 (en) | Benzo seven-membered ring bifunctional compound and application thereof | |
| NZ198389A (en) | 2-(2-benzofuranyl) ethanolamines and pharmaceutical compositions | |
| Carter et al. | Analogs of oxybutynin. Synthesis and antimuscarinic and bladder activity of some substituted 7-amino-1-hydroxy-5-heptyn-2-ones and related compounds | |
| SE503805C2 (sv) | N-Derivat av (fenyletyl-beta-ol)amin, ett förfarande för deras framställning och läkemedelskompositioner som innehåller desamma | |
| Séquin | 13C‐NMR. Spectral Differences between Corresponding Methyl Esters, Phenyl Esters and 2‐Substituted Chromones | |
| YAMATO et al. | Chemical structure and sweet taste of isocoumarin and related compounds. IX | |
| WO2022063317A1 (zh) | 稠合的三并环衍生物及其在药学上的应用 | |
| FR2645532A1 (fr) | Composes ammonium quaternaire ayant une activite myorelaxante et leur procede de preparation | |
| AU674657B2 (en) | Orally active antiviral compounds | |
| NL8103710A (nl) | Heteroprostaglandine-derivaten en werkwijze voor de bereiding daarvan. | |
| JPH07506357A (ja) | 置換１，１，２−トリフェニルブテン及び癌の治療及び診断におけるその使用 | |
| US3322778A (en) | Novel ether derivatives of benzmorphans | |
| EP0027948A1 (en) | Tetrahydro-fluorene compounds, processes for their preparation and pharmaceutical compositions thereof | |
| EP0266246A1 (fr) | Dérivés d'imidazo[4,5-b]pyridinone-2, leur préparation et leur application en thérapeutique | |
| Hayashi et al. | Synthesis and herbicidal activity of geometrical isomers of methyl [[[1-[5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrophenyl]-2-methoxyethylidene] amino] oxy] acetate (AKH-7088) | |
| JPS5854139B2 (ja) | シンキナプロスタンサンルイエンカゴウブツノ セイホウ | |
| CA1194021A (en) | Heteroprostaglandin derivatives and processes for preparing them | |
| Ahmed, S. Asghari*, Hickmott, Peter W.** & Wood | Enamine chemistry: part 28: 1 reaction of?,?-unsaturated acid chlorides with 4, 4-disubstituts: cyclohexanone enamines | |
| 大和正利 et al. | Chemical structure and sweet taste of isocoumarin and related compounds. IX. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |