NL9301241A - N-Derivaten van fenyl-beta-hydroxyethylamine, een werkwijze voor de bereiding daarvan en farmaceutische preparaten die ze bevatten. - Google Patents

N-Derivaten van fenyl-beta-hydroxyethylamine, een werkwijze voor de bereiding daarvan en farmaceutische preparaten die ze bevatten. Download PDF

Info

Publication number: NL9301241A
Authority: NL; Netherlands
Prior art keywords: compound; formula; trans; cis; acoet
Prior art date: 1992-07-17

Application number

NL9301241A

Other languages

English (en)

Dutch (nl)

Original Assignee

Scras

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-07-17

Filing date

1993-07-15

Publication date

1994-02-16

1993-07-15 Application filed by Scras filed Critical Scras

1994-02-16 Publication of NL9301241A publication Critical patent/NL9301241A/nl

Links

238000002360 preparation method Methods 0.000 title claims description 28
238000000034 method Methods 0.000 title claims description 25
230000008569 process Effects 0.000 title claims description 21
239000000825 pharmaceutical preparation Substances 0.000 title description 4
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical class OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 232
-1 β-hydroxyphenylethyl Chemical group 0.000 claims description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 8
WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
230000009467 reduction Effects 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
238000006264 debenzylation reaction Methods 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910019020 PtO2 Inorganic materials 0.000 claims description 4
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000003545 alkoxy 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
150000003939 benzylamines Chemical class 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 193
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 94
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 55
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 54
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 36
238000005160 1H NMR spectroscopy Methods 0.000 description 34
229910001868 water Inorganic materials 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 22
238000004128 high performance liquid chromatography Methods 0.000 description 21
238000005481 NMR spectroscopy Methods 0.000 description 20
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 20
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 20
239000012071 phase Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 19
239000003480 eluent Substances 0.000 description 18
239000001530 fumaric acid Substances 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
238000006467 substitution reaction Methods 0.000 description 15
229940125898 compound 5 Drugs 0.000 description 13
239000000047 product Substances 0.000 description 13
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 9
229940125904 compound 1 Drugs 0.000 description 9
229940125782 compound 2 Drugs 0.000 description 8
229910010084 LiAlH4 Inorganic materials 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
238000010626 work up procedure Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
238000000746 purification Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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 5
125000003118 aryl group Chemical group 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 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
238000001816 cooling Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229960002052 salbutamol Drugs 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000556 agonist Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 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
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
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
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
150000002009 diols Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
238000001727 in vivo Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-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
238000002953 preparative HPLC Methods 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
238000010992 reflux Methods 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 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
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 1
DIXMBHMNEHPFCX-MCMMXHMISA-N (2r)-2-[5-[6-amino-5-[(1r)-1-[5-fluoro-2-(triazol-2-yl)phenyl]ethoxy]pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl]propane-1,2-diol Chemical compound O([C@H](C)C=1C(=CC=C(F)C=1)N1N=CC=N1)C(C(=NC=1)N)=CC=1C=1SC([C@](C)(O)CO)=NC=1C DIXMBHMNEHPFCX-MCMMXHMISA-N 0.000 description 1
HPJGEESDHAUUQR-SKGSPYGFSA-N (2s)-2-[[(2s)-5-(diaminomethylideneamino)-2-[[(2s)-1-[(2s)-5-(diaminomethylideneamino)-2-[[(2s)-2-[[(2s)-3-naphthalen-2-yl-2-(3-pyridin-3-ylpropanoylamino)propanoyl]amino]-3-phenylpropanoyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]buta Chemical compound NC(=O)C[C@@H](C(N)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=C2C=CC=CC2=CC=1)NC(=O)CCC=1C=NC=CC=1)CC1=CC=CC=C1 HPJGEESDHAUUQR-SKGSPYGFSA-N 0.000 description 1
LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 1
VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 1
VPMIAOSOTOODMY-KJAPKAAFSA-N (4r)-6-[(e)-2-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1/C=C/C=1C(C(C)C)=NC(C(C)(C)C)=CC=1C1=CC=C(F)C=C1 VPMIAOSOTOODMY-KJAPKAAFSA-N 0.000 description 1
FRJJJAKBRKABFA-TYFAACHXSA-N (4r,6s)-6-[(e)-2-[6-chloro-4-(4-fluorophenyl)-2-propan-2-ylquinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=C(F)C=C1 FRJJJAKBRKABFA-TYFAACHXSA-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
WRDLTPMUGXTIAM-UHFFFAOYSA-N 1-(oxolan-2-yl)ethanamine Chemical compound CC(N)C1CCCO1 WRDLTPMUGXTIAM-UHFFFAOYSA-N 0.000 description 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
NQOZPTYIJQUKTJ-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)-4-oxo-6-(3-piperidin-1-ylpropoxy)quinazolin-3-yl]-n-propan-2-ylacetamide Chemical compound COC1=CC=CC(C=2N(C(=O)C3=CC(OCCCN4CCCCC4)=CC=C3N=2)CC(=O)NC(C)C)=C1 NQOZPTYIJQUKTJ-UHFFFAOYSA-N 0.000 description 1
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
LHASZEBEQGPCFM-CJFMBICVSA-N 2-amino-4-[(1r)-1-[[(6r)-6-[(5-chloro-2-methoxyphenyl)methyl]-7-oxo-3-(phenoxyamino)-5,6-dihydro-2h-1,4-diazepine-1-carbonyl]amino]propyl]benzoic acid Chemical compound C([C@@H]1CNC(CN(C1=O)C(=O)N[C@H](CC)C=1C=C(N)C(C(O)=O)=CC=1)=NOC=1C=CC=CC=1)C1=CC(Cl)=CC=C1OC LHASZEBEQGPCFM-CJFMBICVSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
LPHWCAUEPAUFHZ-UHFFFAOYSA-N 3,6-Dihydropyridine Chemical compound C1C=CCN=C1 LPHWCAUEPAUFHZ-UHFFFAOYSA-N 0.000 description 1
RVTMIVWSLUDRBP-UHFFFAOYSA-N 3-(oxolan-2-yl)propan-1-amine Chemical compound NCCCC1CCCO1 RVTMIVWSLUDRBP-UHFFFAOYSA-N 0.000 description 1
XVYHFICIWQBZDI-UHFFFAOYSA-N 3-(oxolan-2-yl)propan-1-ol Chemical class OCCCC1CCCO1 XVYHFICIWQBZDI-UHFFFAOYSA-N 0.000 description 1
QTBWCSQGBMPECM-UHFFFAOYSA-N 3-[4-[4-[2-[3-[(dimethylamino)methyl]phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-ethyl-3-pyrazolyl]phenyl]-1,1-dimethylurea Chemical compound N=1N(CC)C=C(C=2C=3C=C(NC=3N=CC=2)C=2C=C(CN(C)C)C=CC=2)C=1C1=CC=C(NC(=O)N(C)C)C=C1 QTBWCSQGBMPECM-UHFFFAOYSA-N 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
JOFDSYLCZIHGGO-UHFFFAOYSA-N 4-[(4-cyclohexylphenyl)methyl-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl-methylamino]acetyl]amino]-2-hydroxybenzoic acid Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)N(C)CC(=O)N(C=1C=C(O)C(C(O)=O)=CC=1)CC(C=C1)=CC=C1C1CCCCC1 JOFDSYLCZIHGGO-UHFFFAOYSA-N 0.000 description 1
DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-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
NHCIXEPZNPKEAR-UHFFFAOYSA-N 6-(oxan-2-yloxy)hexan-1-ol Chemical compound OCCCCCCOC1CCCCO1 NHCIXEPZNPKEAR-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
229940121786 Beta 2 adrenoreceptor agonist Drugs 0.000 description 1
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229910014033 C-OH Inorganic materials 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000700198 Cavia Species 0.000 description 1
CYSWUSAYJNCAKA-FYJFLYSWSA-N ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O Chemical compound ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O CYSWUSAYJNCAKA-FYJFLYSWSA-N 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
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239000012448 Lithium borohydride Substances 0.000 description 1
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239000002253 acid Substances 0.000 description 1
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238000011914 asymmetric synthesis Methods 0.000 description 1
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230000008901 benefit Effects 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 1
239000003638 chemical reducing agent Substances 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
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125801 compound 7f Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000001035 drying Methods 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
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
238000010438 heat treatment Methods 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
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
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 1
229960001047 methyl salicylate Drugs 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PHHRKRGXWSEXFZ-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-3-[[2-[(2,3,4-trifluorophenoxy)methyl]-1,3-benzoxazol-4-yl]oxy]propan-1-amine Chemical compound FC1=C(F)C(F)=CC=C1OCC(OC1=CC=C2)=NC1=C2OCCCNCC1=CC=CN=C1 PHHRKRGXWSEXFZ-UHFFFAOYSA-N 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
RCSBCWXPGSPJNF-UHFFFAOYSA-N n-[4-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-yl]butyl]-4-(1,8-naphthyridin-2-yl)butanamide Chemical compound C1=C(Cl)C(OC(F)(F)F)=CC=C1C(O1)=NN=C1CCCCNC(=O)CCCC1=CC=C(C=CC=N2)C2=N1 RCSBCWXPGSPJNF-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
HBEDNENASUYMPO-LJQANCHMSA-N n-hydroxy-4-[[(2r)-3-oxo-2-(thiophen-2-ylmethyl)-2,4-dihydroquinoxalin-1-yl]methyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CN1C2=CC=CC=C2NC(=O)[C@H]1CC1=CC=CS1 HBEDNENASUYMPO-LJQANCHMSA-N 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
150000007524 organic acids Chemical class 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
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 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
230000008707 rearrangement Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 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
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
238000010998 test method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 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
239000011345 viscous material Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
210000004885 white matter Anatomy 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)

NL9301241A 1992-07-17 1993-07-15 N-Derivaten van fenyl-beta-hydroxyethylamine, een werkwijze voor de bereiding daarvan en farmaceutische preparaten die ze bevatten. NL9301241A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929215274A GB9215274D0 (en)	1992-07-17	1992-07-17	Derivatives of(phenylethyl-beta-ol)amine
GB9215274		1992-07-17

Publications (1)

Publication Number	Publication Date
NL9301241A true NL9301241A (nl)	1994-02-16

Family

ID=10718914

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9301241A NL9301241A (nl)	1992-07-17	1993-07-15	N-Derivaten van fenyl-beta-hydroxyethylamine, een werkwijze voor de bereiding daarvan en farmaceutische preparaten die ze bevatten.

Country Status (32)

Country	Link
US (1)	US5447942A (fr)
JP (1)	JP3204811B2 (fr)
AT (1)	AT403693B (fr)
AU (1)	AU672791B2 (fr)
BE (1)	BE1006429A3 (fr)
CA (1)	CA2100381C (fr)
CH (1)	CH687705A5 (fr)
DE (1)	DE4323976C2 (fr)
DK (1)	DK84793A (fr)
DZ (1)	DZ1704A1 (fr)
ES (1)	ES2067417B1 (fr)
FI (1)	FI933235A (fr)
FR (2)	FR2693723B1 (fr)
GB (2)	GB9215274D0 (fr)
GR (1)	GR1001565B (fr)
HK (1)	HK52596A (fr)
HU (1)	HUT64757A (fr)
IE (1)	IE73266B1 (fr)
IN (1)	IN183086B (fr)
LU (1)	LU88383A1 (fr)
MA (1)	MA22937A1 (fr)
MY (1)	MY109395A (fr)
NL (1)	NL9301241A (fr)
NO (1)	NO302946B1 (fr)
NZ (1)	NZ248041A (fr)
OA (1)	OA09838A (fr)
PL (1)	PL173783B1 (fr)
PT (1)	PT101308B (fr)
RU (1)	RU2060252C1 (fr)
SE (1)	SE503805C2 (fr)
TN (1)	TNSN93081A1 (fr)
ZA (1)	ZA934667B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006025920A2 (fr) *	2004-06-19	2006-03-09	Human Biomolecular Research Institute	Modulateurs de neurotransmetteurs du systeme nerveux central
WO2020148325A1 (fr)	2019-01-15	2020-07-23	Phenex-Fxr Gmbh	Modulateurs de lxr neutres

Family Cites Families (8)

* Cited by examiner, † Cited by third party
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
GR850936B (fr) *	1984-04-17	1985-11-25	Glaxo Group Ltd
DE3731198A1 (de) *	1987-02-07	1988-08-18	Bayer Ag	2-aminomethyltetrahydrofurane
JPS6485964A (en) *	1987-03-12	1989-03-30	Glaxo Group Ltd	Compound
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
JPH03133946A (ja) *	1989-10-10	1991-06-07	Glaxo Group Ltd	フェンエタノールアミン化合物

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 ZA ZA934667A patent/ZA934667B/xx unknown
- 1993-06-29 NO NO932383A patent/NO302946B1/no 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 CH CH02076/93A patent/CH687705A5/fr not_active IP Right Cessation
- 1993-07-09 FR FR9308452A patent/FR2693723B1/fr not_active Expired - Fee Related
- 1993-07-09 BE BE9300712A patent/BE1006429A3/fr not_active IP Right Cessation
- 1993-07-09 FR FR9308453A patent/FR2693653B1/fr not_active Expired - Fee Related
- 1993-07-12 DZ DZ930084A patent/DZ1704A1/fr active
- 1993-07-13 US US08/091,589 patent/US5447942A/en not_active Expired - Lifetime
- 1993-07-13 CA CA002100381A patent/CA2100381C/fr not_active Expired - Fee Related
- 1993-07-15 PT PT101308A patent/PT101308B/pt not_active IP Right Cessation
- 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 LU LU88383A patent/LU88383A1/fr unknown
- 1993-07-16 DK DK084793A patent/DK84793A/da not_active Application Discontinuation
- 1993-07-16 JP JP17693293A patent/JP3204811B2/ja not_active Expired - Fee Related
- 1993-07-16 MA MA23237A patent/MA22937A1/fr unknown
- 1993-07-16 SE SE9302437A patent/SE503805C2/sv not_active IP Right Cessation
- 1993-07-16 ES ES09301603A patent/ES2067417B1/es 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 AU AU42042/93A patent/AU672791B2/en not_active Ceased
- 1993-07-16 RU RU9393046412A patent/RU2060252C1/ru active
- 1993-07-16 HU HU9302057A patent/HUT64757A/hu unknown
- 1993-07-16 FI FI933235A patent/FI933235A/fi unknown
- 1993-07-16 TN TNTNSN93081A patent/TNSN93081A1/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

Publication number	Publication date
SE9302437L (sv)	1994-01-18
NO932383D0 (no)	1993-06-29
NO932383L (no)	1994-01-18
FR2693653A1 (fr)	1994-01-21
GB9215274D0 (en)	1992-09-02
RU2060252C1 (ru)	1996-05-20
MY109395A (en)	1997-01-31
MA22937A1 (fr)	1994-04-01
JPH06157492A (ja)	1994-06-03
FR2693653B1 (fr)	1994-10-28
DK84793D0 (da)	1993-07-16
FI933235A (fi)	1994-01-18
GB2268742B (en)	1995-11-08
GR1001565B (el)	1994-05-31
IN183086B (fr)	1999-09-04
PT101308B (pt)	1999-10-29
TNSN93081A1 (fr)	1994-03-17
FI933235A0 (fi)	1993-07-16
DE4323976A1 (de)	1994-01-20
GB2268742A (en)	1994-01-19
HUT64757A (en)	1994-02-28
BE1006429A3 (fr)	1994-08-23
FR2693723B1 (fr)	1994-10-28
CA2100381A1 (fr)	1994-01-18
DK84793A (da)	1994-01-18
IE930472A1 (en)	1994-01-26
NZ248041A (en)	1994-06-27
HU9302057D0 (en)	1993-10-28
ES2067417A1 (es)	1995-03-16
FR2693723A1 (fr)	1994-01-21
PT101308A (pt)	1994-05-31
HK52596A (en)	1996-04-03
JP3204811B2 (ja)	2001-09-04
PL173783B1 (pl)	1998-04-30
PL299693A1 (en)	1994-03-21
CH687705A5 (fr)	1997-01-31
IE73266B1 (en)	1997-05-21
AU4204293A (en)	1994-01-20
AT403693B (de)	1998-04-27
DZ1704A1 (fr)	2002-02-17
NO302946B1 (no)	1998-05-11
ZA934667B (en)	1994-01-25
GB9314718D0 (en)	1993-08-25
OA09838A (fr)	1994-08-15
SE9302437D0 (sv)	1993-07-16
ES2067417B1 (es)	1995-11-16
US5447942A (en)	1995-09-05
CA2100381C (fr)	2004-09-21
ATA142793A (de)	1997-09-15
AU672791B2 (en)	1996-10-17
DE4323976C2 (de)	2003-05-28
SE503805C2 (sv)	1996-09-09
LU88383A1 (fr)	1994-04-01

Legal Events

Date	Code	Title
1996-05-01	BA	A request for search or an international-type search has been filed
1996-08-01	BB	A search report has been drawn up
1997-02-03	BC	A request for examination has been filed
2001-11-01	BI	The patent application has been withdrawn

Publication	Publication Date	Title
EP0465358B1 (fr)	1996-02-07	Dérivé thiényl-2 glycidique, son procédé de préparation et son utilisation comme intermédiaire de synthèse
FR2670491A1 (fr)	1992-06-19	Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant.
CH647520A5 (fr)	1985-01-31	Derives du nortropane, leur procede de preparation et composition pharmaceutique les contenant.
WO2002016339A1 (fr)	2002-02-28	Aminoalkylbenzoyl-benzofuranes ou benzothiophenes, leur procede de preparation et les compositions les contenant
EP0424243B1 (fr)	1995-08-23	Dérivés d'aryl-3 oxazolidinone, leur procédé de préparation et leur application en thérapeutique
FR2642065A1 (fr)	1990-07-27	Derives d'acides benzocycloalcenyl dihydroxy alcanoiques, procede de preparation et medicaments les contenant
JPH03101670A (ja)	1991-04-26	Ｐａｆ拮抗物質である新規な２，５‐ジアリールテトラヒドロフランおよびその類似体
EP0461958B1 (fr)	1994-09-14	Dérivés de 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanes, leur préparation et leur application en thérapeutique
FR2611139A1 (fr)	1988-08-26	Medicaments a base de nouveaux derives oxy-5 du tetrahydrofurane
NL9301241A (nl)	1994-02-16	N-Derivaten van fenyl-beta-hydroxyethylamine, een werkwijze voor de bereiding daarvan en farmaceutische preparaten die ze bevatten.
FR2634207A1 (fr)	1990-01-19	Derives de ((piperidinyl-4)methyl) benzazepines, leur preparation et leur application en therapeutique
CH635570A5 (fr)	1983-04-15	Derives d'amino-alcools.
CH646694A5 (fr)	1984-12-14	Derives de la 3,4,5-trimethoxy cinnamoyle piperazine et leur procede de preparation.
Li et al.	1981	Intramolecular. alpha.-amidoalkylation of an olefin for the synthesis of a useful prostaglandin intermediate
FR2518992A1 (fr)	1983-07-01	Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique
FR2508032A1 (fr)	1982-12-24	Nouveaux derives amino-3 aryloxymethyl-2 propanol-1, leur procede de preparation et leurs applications en therapeutique
EP0323303B1 (fr)	1992-08-12	Dérivés de nicotinoyl-pipérazine, procédé de préparation et utilisation en thérapeutique
Ahmed, S. Asghari, Hickmott, Peter W.* & Wood	1985	Enamine chemistry: part 28: 1 reaction of?,?-unsaturated acid chlorides with 4, 4-disubstituts: cyclohexanone enamines
FR2461497A1 (fr)	1981-02-06	Nouvelles compositions therapeutiques a base de certains derives de l'isoquinoleine
CH409939A (fr)	1966-03-31	Procédé de préparation d'amines dérivées du dibenzo (a,d) (1,4) cycloheptadiène
FR2663330A1 (fr)	1991-12-20	0derives de 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanes, leur preparation et leur application en therapeutique.
FR2714056A1 (fr)	1995-06-23	Dérivés de 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxane, leur préparation et leur application en thérapeutique.
FR2634205A2 (fr)	1990-01-19	Derives de me thyl-4 ((piperidinyl-4)methyl)-2 tetrahydro-1,2,3,4 isoquinoleine, leur preparation et leur application en therapeutique