CA1127164A - Derives des 1-phenyl-1-propanols - Google Patents

Derives des 1-phenyl-1-propanols

Info

Publication number: CA1127164A
Authority: CA; Canada
Prior art keywords: radical; group; propanol; ramified; linear
Prior art date: 1978-07-13
Legal status (The legal status 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 status listed.): Expired

Application number

CA331,500A

Other languages

English (en)

Inventor

Georges Lambelin

Romeo Roncucci

Joseph Roba

Claude Gillet

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Continental Pharma Inc

Original Assignee

Continental Pharma Inc

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.)

1978-07-13

Filing date

1979-07-10

Publication date

1982-07-06

1979-07-10 Application filed by Continental Pharma Inc filed Critical Continental Pharma Inc

1982-07-06 Application granted granted Critical

1982-07-06 Publication of CA1127164A publication Critical patent/CA1127164A/fr

Status Expired legal-status Critical Current

Links

DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical class CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 title claims abstract 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 15
150000002148 esters Chemical class 0.000 claims abstract description 10
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 7
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
231100000252 nontoxic Toxicity 0.000 claims abstract description 4
230000003000 nontoxic effect Effects 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 42
-1 carbomethoxy group Chemical group 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
238000000034 method Methods 0.000 claims description 32
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
230000009471 action Effects 0.000 claims description 28
230000008569 process Effects 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 24
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 19
230000009467 reduction Effects 0.000 claims description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 14
238000007254 oxidation reaction Methods 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
239000012279 sodium borohydride Substances 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
229910052987 metal hydride Inorganic materials 0.000 claims description 6
150000004681 metal hydrides Chemical class 0.000 claims description 6
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
229940095054 ammoniac Drugs 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
150000007529 inorganic bases Chemical class 0.000 claims description 5
150000002739 metals Chemical class 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
230000001131 transforming effect Effects 0.000 claims description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 3
239000004411 aluminium Substances 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
238000004821 distillation Methods 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
239000002516 radical scavenger Substances 0.000 claims description 3
XDJBXZARAXHDPH-UHFFFAOYSA-N 2-(octylamino)-1-(4-sulfanylphenyl)propan-1-ol Chemical compound SC1=CC=C(C=C1)C(C(C)NCCCCCCCC)O XDJBXZARAXHDPH-UHFFFAOYSA-N 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000004440 column chromatography Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
229910003446 platinum oxide Inorganic materials 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
241001565477 Aphyosemion omega Species 0.000 claims 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims 1
239000003849 aromatic solvent Substances 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
239000000047 product Substances 0.000 description 26
230000000694 effects Effects 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
229940044613 1-propanol Drugs 0.000 description 12
229960001701 chloroform Drugs 0.000 description 12
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
229960005335 propanol Drugs 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
125000006308 propyl amino group Chemical group 0.000 description 7
229930008281 A03AD01 - Papaverine Natural products 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
229960001789 papaverine Drugs 0.000 description 6
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
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 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000008101 lactose Substances 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
238000011534 incubation Methods 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229940057952 methanol Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000000810 peripheral vasodilating agent Substances 0.000 description 3
229960002116 peripheral vasodilator Drugs 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 3
229960004793 sucrose Drugs 0.000 description 3
210000003568 synaptosome Anatomy 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
WFVPERLEYPIUPH-UHFFFAOYSA-N 2-(octylamino)-1-(4-propan-2-ylsulfinylphenyl)propan-1-ol Chemical compound CCCCCCCCNC(C)C(O)C1=CC=C(S(=O)C(C)C)C=C1 WFVPERLEYPIUPH-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical class OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
229910002012 Aerosil® Inorganic materials 0.000 description 2
ZAZUIDXBORYCIK-UHFFFAOYSA-N CC1OC1C1=CC=C(C=C1)SC(C)C Chemical compound CC1OC1C1=CC=C(C=C1)SC(C)C ZAZUIDXBORYCIK-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
229920003148 Eudragit® E polymer Polymers 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
241001072983 Mentha Species 0.000 description 2
235000006679 Mentha X verticillata Nutrition 0.000 description 2
235000002899 Mentha suaveolens Nutrition 0.000 description 2
235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
229920000715 Mucilage Polymers 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
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235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
210000001772 blood platelet Anatomy 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000013270 controlled release Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
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239000012043 crude product Substances 0.000 description 2
235000013681 dietary sucrose Nutrition 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 2
229960004194 lidocaine Drugs 0.000 description 2
230000004130 lipolysis Effects 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
125000005476 oxopyrrolidinyl group Chemical group 0.000 description 2
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OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
239000000902 placebo Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000004044 response Effects 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000004873 systolic arterial blood pressure Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000004474 valine Substances 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003754 zirconium Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA331,500A 1978-07-13 1979-07-10 Derives des 1-phenyl-1-propanols Expired CA1127164A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU79.970		1978-07-13
LU79970A LU79970A1 (fr)	1978-07-13	1978-07-13	Procede de preparation de derives de 1-phenyl-1-propanol

Publications (1)

Publication Number	Publication Date
CA1127164A true CA1127164A (fr)	1982-07-06

Family

ID=19728955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA331,500A Expired CA1127164A (fr)	1978-07-13	1979-07-10	Derives des 1-phenyl-1-propanols

Country Status (18)

Country	Link
JP (1)	JPS5943943B2 (fr)
AT (1)	AT368491B (fr)
BE (1)	BE877694A (fr)
CA (1)	CA1127164A (fr)
CH (1)	CH644355A5 (fr)
DE (1)	DE2927789A1 (fr)
DK (1)	DK293779A (fr)
ES (1)	ES482432A1 (fr)
FI (1)	FI792123A7 (fr)
FR (2)	FR2438649A1 (fr)
GB (1)	GB2025417B (fr)
IT (1)	IT1122180B (fr)
LU (1)	LU79970A1 (fr)
NL (1)	NL7905507A (fr)
NO (1)	NO148452C (fr)
PT (1)	PT69909A (fr)
SE (1)	SE446631B (fr)
ZA (1)	ZA793554B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8178077B2 (en)	2004-10-19	2012-05-15	Reverse Proteomics Research Institute Co., Ltd.	Drug development target protein and target gene, and method of screening

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3128117A1 (de) *	1980-07-29	1982-03-11	Yamanouchi Pharmaceutical Co., Ltd., Tokyo	Neue phenyl-aethylaminderivate, verfahren zu ihrer herstellung
LU83039A1 (fr) *	1980-12-24	1982-07-07	Continental Pharma	Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol
DE3262620D1 (en) *	1981-05-27	1985-04-25	Maggioni Farma	4-alkyl-thiophenyl-ethanolamines, having an activity on the cerebral circulation, the blood platelet-aggregation and the lipemia
FR2537132B1 (fr) *	1982-12-06	1987-01-09	Lafon Labor	Nouveaux derives soufres de 2-amino-1-phenyl-1-ethanol, utilisation en therapeutique et procede de preparation
US4582918A (en) *	1984-09-19	1986-04-15	Schering Corporation	Preparation of intermediates for (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols
BE1014245A4 (fr) *	2001-04-03	2003-07-01	Malak Jean	Composes chimiques derives de l'octopamine et leurs utilisations en tant qu'agonistes beta 3-adrenergiques.
IL187245A0 (en) *	2007-11-08	2008-12-29	Hadasit Med Res Service	Synthetic sphingolipid analogs

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1366096A (fr) *	1962-05-28	1964-07-10	Castrol Ltd	Copolymères pour utilisation dans les compositions d'huiles lubrifiantes et leurs produits intermédiaires
FR1480780A (fr) *	1965-05-24	1967-05-12	Shell Int Research	Production de pyrrolidone

1978
- 1978-07-13 LU LU79970A patent/LU79970A1/fr unknown
1979
- 1979-07-05 FI FI792123A patent/FI792123A7/fi not_active Application Discontinuation
- 1979-07-10 DE DE19792927789 patent/DE2927789A1/de not_active Ceased
- 1979-07-10 CA CA331,500A patent/CA1127164A/fr not_active Expired
- 1979-07-10 SE SE7905992A patent/SE446631B/sv not_active Application Discontinuation
- 1979-07-11 AT AT0483579A patent/AT368491B/de not_active IP Right Cessation
- 1979-07-12 GB GB7924292A patent/GB2025417B/en not_active Expired
- 1979-07-12 NO NO792329A patent/NO148452C/no unknown
- 1979-07-12 FR FR7918156A patent/FR2438649A1/fr active Granted
- 1979-07-12 ES ES482432A patent/ES482432A1/es not_active Expired
- 1979-07-12 CH CH651479A patent/CH644355A5/fr not_active IP Right Cessation
- 1979-07-12 DK DK293779A patent/DK293779A/da not_active Application Discontinuation
- 1979-07-12 PT PT69909A patent/PT69909A/fr unknown
- 1979-07-13 NL NL7905507A patent/NL7905507A/nl not_active Application Discontinuation
- 1979-07-13 ZA ZA00793554A patent/ZA793554B/xx unknown
- 1979-07-13 IT IT24357/79A patent/IT1122180B/it active
- 1979-07-13 BE BE0/196294A patent/BE877694A/fr not_active IP Right Cessation
- 1979-07-13 JP JP54088352A patent/JPS5943943B2/ja not_active Expired
1980
- 1980-02-13 FR FR8003187A patent/FR2443457A1/fr active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8178077B2 (en)	2004-10-19	2012-05-15	Reverse Proteomics Research Institute Co., Ltd.	Drug development target protein and target gene, and method of screening

Also Published As

Publication number	Publication date
CH644355A5 (fr)	1984-07-31
IT7924357A0 (it)	1979-07-13
JPS5943943B2 (ja)	1984-10-25
ATA483579A (de)	1982-02-15
PT69909A (fr)	1979-08-01
FR2438649B1 (fr)	1983-03-25
FR2443457B1 (fr)	1983-09-23
NO792329L (no)	1980-01-15
BE877694A (fr)	1979-11-05
NO148452B (no)	1983-07-04
GB2025417A (en)	1980-01-23
AT368491B (de)	1982-10-11
ES482432A1 (es)	1980-04-01
FI792123A7 (fi)	1981-01-01
IT1122180B (it)	1986-04-23
DK293779A (da)	1980-01-14
JPS5533467A (en)	1980-03-08
DE2927789A1 (de)	1980-01-24
SE446631B (sv)	1986-09-29
LU79970A1 (fr)	1980-02-14
NO148452C (no)	1983-10-12
GB2025417B (en)	1983-03-02
FR2443457A1 (fr)	1980-07-04
NL7905507A (nl)	1980-01-15
FR2438649A1 (fr)	1980-05-09
ZA793554B (en)	1980-06-25
SE7905992L (sv)	1980-01-14

Legal Events

Date	Code	Title	Description
1999-07-06	MKEX	Expiry

Publication	Publication Date	Title
Gao et al.	1988	Asymmetric synthesis of both enantiomers of tomoxetine and fluoxetine. Selective reduction of 2, 3-epoxycinnamyl alcohol with Red-Al
AU699489B2 (en)	1998-12-03	Novel benzoxazoles
CA1127164A (fr)	1982-07-06	Derives des 1-phenyl-1-propanols
US4059622A (en)	1977-11-22	Alkanolamine derivatives
JPS6110528A (ja)	1986-01-18	フエノ−ル誘導体、その製造法、および該化合物を含有する抗エストロゲン作用を有する医薬組成物
CA1280416C (fr)	1991-02-19	Derives de phenol antiestrogeniques
EP0424244A1 (fr)	1991-04-24	Dérivés d'aryl-3 oxazolidinone, leur procédé de préparation et leur application en thérapeutique
KR840001552B1 (ko)	1984-10-05	시클로헥센 유도체의 제조방법
US4701542A (en)	1987-10-20	Resolution of hemiacetals and alcohols
Nuhrich et al.	1991	Cyclisation de N-tosyl oxiranes-propylamines: Synthese d'heterocycles azotes.
MC1516A1 (fr)	1984-02-10	Nouveaux derives d'aziridine et de phenethanolamine
Beacham et al.	1991	Acetonides of heptonolactones: powerful chirons
MC1693A1 (fr)	1986-07-18	Nouveaux composes,compositions les contenant et intermediaires pour leur preparation
CN109053496B (zh)	2020-10-20	一种3-Boc-氨甲基环丁酮的合成方法
SK14698A3 (en)	1998-10-07	Benzenesulphonamide derivatives, preparation thereof and therapeutical uses thereof
WO1998043964A1 (fr)	1998-10-08	Derives de 2-[(3-substitue)-5-isoxazolylmethylamino]alkanamide
Tomie et al.	1976	Synthesis of optically Active Prenylamine from (-)-Norephedrine
US4321201A (en)	1982-03-23	Optically active tert-alkyl 7-(2-oxo-5-carbonyloxypyrrolidinyl) heptanoates
JPS606653A (ja)	1985-01-14	抗高コレステロ−ル血症活性を有する５−チアアルカン酸誘導体
PT97858A (pt)	1992-03-31	Metodo para a preparacao de um composto dicloroanilina tendo um substituinte contendo um grupo piridinilo
EP0259228B1 (fr)	1992-06-03	Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique
CA1085841A (fr)	1980-09-16	Obtention et emploi d'aryloxypropylamines
PL163378B1 (pl)	1994-03-31	Sposób wytwarzania nowych pochodnych benzoksazolonu PL PL PL
FR2741071A1 (fr)	1997-05-16	Derives de 3-(benzofuran-5-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique
EP0213547A1 (fr)	1987-03-11	Acides cyclohexanealkanoiques

CA1127164A - Derives des 1-phenyl-1-propanols - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=19728955

Family Applications (1)

Country Status (18)

Cited By (1)

Families Citing this family (7)

Family Cites Families (2)

Cited By (1)

Also Published As

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