CH646165A5 - Derives de l'amino-1 propanol-2, leur procede de preparation. - Google Patents
Derives de l'amino-1 propanol-2, leur procede de preparation. Download PDFInfo
- Publication number
- CH646165A5 CH646165A5 CH893680A CH893680A CH646165A5 CH 646165 A5 CH646165 A5 CH 646165A5 CH 893680 A CH893680 A CH 893680A CH 893680 A CH893680 A CH 893680A CH 646165 A5 CH646165 A5 CH 646165A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- group
- alkyl
- linear
- alkyl group
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- -1 pyrrolidino, morpholino Chemical group 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 150000007522 mineralic acids Chemical class 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- 235000005985 organic acids Nutrition 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 22
- 238000009833 condensation Methods 0.000 description 20
- 230000005494 condensation Effects 0.000 description 20
- HUUJEEJATAODFP-UHFFFAOYSA-N C1CC2=C(C=C(S2)OCC3CO3)C(=N)C1 Chemical compound C1CC2=C(C=C(S2)OCC3CO3)C(=N)C1 HUUJEEJATAODFP-UHFFFAOYSA-N 0.000 description 17
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- 230000008602 contraction Effects 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- YRMWVRKJJXTRCB-UHFFFAOYSA-N 6,7-dihydro-5h-1-benzothiophen-4-imine Chemical compound N=C1CCCC2=C1C=CS2 YRMWVRKJJXTRCB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 229960001317 isoprenaline Drugs 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- JCCFKRNCMIHDFF-UHFFFAOYSA-N 4h-cyclohepta[b]thiophene Chemical compound C1C=CC=CC2=C1C=CS2 JCCFKRNCMIHDFF-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000009090 positive inotropic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- UCTWMZQNUQWSLP-SECBINFHSA-N (S)-adrenaline Chemical compound CNC[C@@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-SECBINFHSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- NFEPWWCVSNKOQV-UHFFFAOYSA-N C1CC2=C(C=C(S2)OCC(C(CC3=CN=CC=C3)N)O)C(=N)C1 Chemical compound C1CC2=C(C=C(S2)OCC(C(CC3=CN=CC=C3)N)O)C(=N)C1 NFEPWWCVSNKOQV-UHFFFAOYSA-N 0.000 description 1
- YDXYZRPJSGQDPT-UHFFFAOYSA-N C1CC2=C(C=C(S2)OCC(CN3CCOCC3)O)C(=N)C1 Chemical compound C1CC2=C(C=C(S2)OCC(CN3CCOCC3)O)C(=N)C1 YDXYZRPJSGQDPT-UHFFFAOYSA-N 0.000 description 1
- YLZLEQSUTGVIJJ-UHFFFAOYSA-N C1CCC(CC1)NCC(COC2=CC3=C(S2)CCCC3=N)O Chemical compound C1CCC(CC1)NCC(COC2=CC3=C(S2)CCCC3=N)O YLZLEQSUTGVIJJ-UHFFFAOYSA-N 0.000 description 1
- FUBIBKJOUCXKST-UHFFFAOYSA-N CC(C)NCC(COC1=CC2=C(S1)CCCC2=N)O Chemical compound CC(C)NCC(COC1=CC2=C(S1)CCCC2=N)O FUBIBKJOUCXKST-UHFFFAOYSA-N 0.000 description 1
- 101100028482 Caenorhabditis elegans pal-1 gene Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-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
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 229940082483 carnauba wax Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical compound NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940015849 thiophene Drugs 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7931402A FR2471980A1 (fr) | 1979-12-21 | 1979-12-21 | Nouveaux derives de l'amino-1 propanol-2, leur procede de preparation et leur application therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH646165A5 true CH646165A5 (fr) | 1984-11-15 |
Family
ID=9233060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH893680A CH646165A5 (fr) | 1979-12-21 | 1980-12-02 | Derives de l'amino-1 propanol-2, leur procede de preparation. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4339450A (OSRAM) |
| EP (1) | EP0031266B1 (OSRAM) |
| JP (1) | JPS5699472A (OSRAM) |
| AR (1) | AR225937A1 (OSRAM) |
| AU (1) | AU541684B2 (OSRAM) |
| BE (1) | BE886471A (OSRAM) |
| BG (1) | BG35047A3 (OSRAM) |
| CA (1) | CA1158643A (OSRAM) |
| CH (1) | CH646165A5 (OSRAM) |
| CS (1) | CS228143B2 (OSRAM) |
| DE (1) | DE3061928D1 (OSRAM) |
| DK (1) | DK536180A (OSRAM) |
| ES (1) | ES497563A0 (OSRAM) |
| FR (1) | FR2471980A1 (OSRAM) |
| GB (1) | GB2066808B (OSRAM) |
| GR (1) | GR72831B (OSRAM) |
| HU (1) | HU181774B (OSRAM) |
| IE (1) | IE50546B1 (OSRAM) |
| IL (1) | IL61602A (OSRAM) |
| IN (1) | IN150867B (OSRAM) |
| IT (1) | IT1141642B (OSRAM) |
| LU (1) | LU83021A1 (OSRAM) |
| NZ (1) | NZ195786A (OSRAM) |
| PL (1) | PL127009B1 (OSRAM) |
| PT (1) | PT72247B (OSRAM) |
| RO (1) | RO80266B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704604A1 (de) * | 1987-02-13 | 1988-08-25 | Mack Chem Pharm | Oximether von 2,6-dioxabicyclo(3.3.0)octanonen, herstellungsverfahren und anwendung als arzneimittel |
| US4803286A (en) * | 1987-08-19 | 1989-02-07 | Merck & Co., Inc. | Amino-2-hydroxypropyloximinoheterocycle α-blockers |
| EP0347378A1 (de) * | 1988-06-13 | 1989-12-20 | Ciba-Geigy Ag | Imidazol-Derivate |
| IL103106A (en) | 1991-09-25 | 1998-06-15 | Sanofi Elf | Ethers of thienocyclopentanone oximes, their preparation and pharmaceutical compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3398161A (en) * | 1965-06-30 | 1968-08-20 | Ici Ltd | Benzo (b) thiophen derivatives which have beta-adrenergic blocking activity |
| NL6810133A (OSRAM) * | 1968-07-18 | 1970-01-20 |
-
1979
- 1979-12-21 FR FR7931402A patent/FR2471980A1/fr active Granted
-
1980
- 1980-11-15 GR GR63372A patent/GR72831B/el unknown
- 1980-11-18 GB GB8036920A patent/GB2066808B/en not_active Expired
- 1980-12-01 IL IL8061602A patent/IL61602A/xx unknown
- 1980-12-01 DE DE8080401713T patent/DE3061928D1/de not_active Expired
- 1980-12-01 EP EP80401713A patent/EP0031266B1/fr not_active Expired
- 1980-12-02 CH CH893680A patent/CH646165A5/fr not_active IP Right Cessation
- 1980-12-03 BE BE0/203024A patent/BE886471A/fr not_active IP Right Cessation
- 1980-12-04 IE IE2535/80A patent/IE50546B1/en unknown
- 1980-12-09 NZ NZ195786A patent/NZ195786A/xx unknown
- 1980-12-10 ES ES497563A patent/ES497563A0/es active Granted
- 1980-12-12 BG BG049969A patent/BG35047A3/xx unknown
- 1980-12-16 RO RO102863A patent/RO80266B/ro unknown
- 1980-12-17 AR AR283678A patent/AR225937A1/es active
- 1980-12-17 DK DK536180A patent/DK536180A/da not_active Application Discontinuation
- 1980-12-18 IT IT68942/80A patent/IT1141642B/it active
- 1980-12-18 CA CA000367082A patent/CA1158643A/en not_active Expired
- 1980-12-19 HU HU803060A patent/HU181774B/hu unknown
- 1980-12-19 PL PL1980228606A patent/PL127009B1/pl unknown
- 1980-12-19 LU LU83021A patent/LU83021A1/fr unknown
- 1980-12-19 CS CS809065A patent/CS228143B2/cs unknown
- 1980-12-19 AU AU65587/80A patent/AU541684B2/en not_active Ceased
- 1980-12-19 PT PT72247A patent/PT72247B/pt unknown
- 1980-12-22 US US06/219,213 patent/US4339450A/en not_active Expired - Fee Related
- 1980-12-22 JP JP18180280A patent/JPS5699472A/ja active Pending
-
1981
- 1981-01-17 IN IN54/CAL/81A patent/IN150867B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0527687B1 (fr) | Nouveaux dérivés d'aryléthylamines, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent | |
| DE60129806T2 (de) | Neue bizyklische verbindungen | |
| EP0506539B1 (fr) | Amides alkyl hétérocycliques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| FR2665444A1 (fr) | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. | |
| PL121297B1 (en) | Process for preparing novel derivatives of phenethanolamine | |
| FR2479825A1 (fr) | Benzodioxanne 1,4 methoxy-2 propanolamines, leur preparation et leur application en tant que medicaments | |
| EP0092458A2 (fr) | Dérives d'imidazo(1,2-a)pyridine, leur préparation et leur application en thérapeutique | |
| CH641759A5 (fr) | Phenethanolamines et composition pharmaceutique antineoplastique les contenant. | |
| CH617697A5 (OSRAM) | ||
| FR2639044A1 (fr) | Derives de la butynylamine | |
| EP0068998B1 (fr) | Aryl-1 aminométhyl-2 cyclopropanes carboxylates (Z), leur préparation et leur application en tant que médicaments utiles dans le traitement d'algies diverses | |
| FR2463765A1 (fr) | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire | |
| EP0031266B1 (fr) | Nouveaux dérivés de l'amino-1 propanol-2, leur procédé de préparation et leur application thérapeutique | |
| FR2550091A1 (fr) | Composition pharmaceutique ou veterinaire destinee a combattre des troubles ischemiques cardiaques contenant un derive du benzofuranne | |
| FR2646349A1 (fr) | Derives du 4-phenylmethyl lh-indole, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant | |
| EP0002635B1 (fr) | Procédé de préparation de dérivés de thiéno (2,3-c) et (3,2-c) pyridines, nouveaux dérivés de la thiéno (2,3-c) pyridine obtenus et leur application thérapeutique | |
| EP1957490B1 (fr) | Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant | |
| EP0117171B1 (fr) | Dérivés aminés de la pyridazine substitués en position 6 par un hétérocycle ou un alicycle, procédé d'obtention et médicaments les contenant | |
| EP0183577B1 (fr) | Dérivés du thiadiazole actifs sur le système nerveux central, procédé d'obtension et compositions pharmaceutiques les contenant | |
| FR2559771A1 (fr) | Derives de la 3-pyrrolidinopropiophenone et procede pour leur preparation | |
| CH631713A5 (fr) | Derives de chromones a activite medicamenteuse et leur preparation. | |
| EP0244318B1 (fr) | Nouveaux dérivés de la N-[(triméthoxy-2,4,6-benzoyl)-3 propyl] pipéridine, leurs procédés de préparation et leur application en thérapeutique | |
| FR2518537A1 (fr) | Nouveaux derives de l'acide phenylacetique, leur preparation et compositions les contenant | |
| FR2537583A1 (fr) | Enantiomeres levogyres des derives de la tetrahydro-5, 6, 13, 13a 8h-dibenzo (a,g-) quinolizine, procedes d'obtention, compositions pharmaceutiques les contenant et application | |
| CH623046A5 (OSRAM) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |