NL7905507A - 1-fenylpropanol-1-derivaten, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten, die de derivaten bevatten. - Google Patents

1-fenylpropanol-1-derivaten, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten, die de derivaten bevatten. Download PDF

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Publication number: NL7905507A
Authority: NL; Netherlands
Prior art keywords: group; formula; derivatives; solvent; process according
Prior art date: 1978-07-13

Application number

NL7905507A

Other languages

English (en)

Dutch (nl)

Original Assignee

Continental Pharma

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

1979-07-13

Publication date

1980-01-15

1979-07-13 Application filed by Continental Pharma filed Critical Continental Pharma

1980-01-15 Publication of NL7905507A publication Critical patent/NL7905507A/nl

Links

238000000034 method Methods 0.000 title claims description 41
239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
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 58
-1 carbomethoxy group Chemical group 0.000 claims description 55
150000001875 compounds Chemical class 0.000 claims description 50
239000002904 solvent Substances 0.000 claims description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
230000009471 action Effects 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 23
230000008569 process Effects 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 21
230000009467 reduction Effects 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000006308 propyl amino group Chemical group 0.000 claims description 13
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 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
229910052782 aluminium Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
239000007800 oxidant agent Substances 0.000 claims description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 5
150000008046 alkali metal hydrides Chemical class 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
238000004821 distillation Methods 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910000103 lithium hydride Inorganic materials 0.000 claims description 4
239000002609 medium Substances 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
150000004678 hydrides Chemical class 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
239000012279 sodium borohydride Substances 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
101150009274 nhr-1 gene Proteins 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
238000010992 reflux Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims 2
229910000039 hydrogen halide Inorganic materials 0.000 claims 2
239000003849 aromatic solvent Substances 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
229910052987 metal hydride Inorganic materials 0.000 claims 1
150000004681 metal hydrides Chemical class 0.000 claims 1
150000002739 metals Chemical class 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
125000003396 thiol group Chemical group [H]S* 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
239000000047 product Substances 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
230000000694 effects Effects 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
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
229930008281 A03AD01 - Papaverine Natural products 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
230000005764 inhibitory process Effects 0.000 description 6
229960001789 papaverine Drugs 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
229910002012 Aerosil® Inorganic materials 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
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
239000000460 chlorine Substances 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
235000019341 magnesium sulphate Nutrition 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
230000000304 vasodilatating effect Effects 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
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
229910052801 chlorine Inorganic materials 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000011534 incubation Methods 0.000 description 3
229960004194 lidocaine Drugs 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229960004793 sucrose Drugs 0.000 description 3
210000003568 synaptosome Anatomy 0.000 description 3
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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229920003148 Eudragit® E polymer Polymers 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
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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239000002585 base Substances 0.000 description 2
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MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 2
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229910052794 bromium Inorganic materials 0.000 description 2
NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 2
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210000003191 femoral vein Anatomy 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
230000004130 lipolysis Effects 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
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229910017604 nitric acid Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000010412 perfusion Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
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KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008274 jelly Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000003170 musculotropic effect Effects 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 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
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
RZTDESRVPFKCBH-UHFFFAOYSA-N p-Tol-Tol-p Natural products C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000902 placebo Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
210000004623 platelet-rich plasma Anatomy 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
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BIZGMTWBKDPTLH-UHFFFAOYSA-N propan-2-yl hypochlorite Chemical compound CC(C)OCl BIZGMTWBKDPTLH-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011946 reduction process Methods 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
150000003283 rhodium Chemical class 0.000 description 1
238000007363 ring formation 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
229960004889 salicylic acid Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 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
229940076279 serotonin Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 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
239000000021 stimulant Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229950000244 sulfanilic acid Drugs 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
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 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
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 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
210000001519 tissue Anatomy 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000004474 valine Substances 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
210000003462 vein Anatomy 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)

NL7905507A 1978-07-13 1979-07-13 1-fenylpropanol-1-derivaten, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten, die de derivaten bevatten. NL7905507A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU79970A LU79970A1 (fr)	1978-07-13	1978-07-13	Procede de preparation de derives de 1-phenyl-1-propanol
LU79970		1978-07-13

Publications (1)

Publication Number	Publication Date
NL7905507A true NL7905507A (nl)	1980-01-15

Family

ID=19728955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7905507A NL7905507A (nl)	1978-07-13	1979-07-13	1-fenylpropanol-1-derivaten, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten, die de derivaten bevatten.

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)

Families Citing this family (8)

* 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
EP0066919B1 (fr) *	1981-05-27	1985-03-20	MAGGIONI FARMACEUTICI S.p.A.	Alcoyl-thio-4-phényl-éthanolamines, ayant une activité sur la circulation cérébrale, sur l'agrégation des plaquettes sanguines et sur la lipémie
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.
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
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 PT PT69909A patent/PT69909A/fr unknown
- 1979-07-12 NO NO792329A patent/NO148452C/no unknown
- 1979-07-12 GB GB7924292A patent/GB2025417B/en not_active Expired
- 1979-07-12 DK DK293779A patent/DK293779A/da not_active Application Discontinuation
- 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 FR FR7918156A patent/FR2438649A1/fr active Granted
- 1979-07-13 NL NL7905507A patent/NL7905507A/nl not_active Application Discontinuation
- 1979-07-13 ZA ZA00793554A patent/ZA793554B/xx unknown
- 1979-07-13 JP JP54088352A patent/JPS5943943B2/ja not_active Expired
- 1979-07-13 IT IT24357/79A patent/IT1122180B/it active
- 1979-07-13 BE BE0/196294A patent/BE877694A/fr not_active IP Right Cessation
1980
- 1980-02-13 FR FR8003187A patent/FR2443457A1/fr active Granted

Also Published As

Publication number	Publication date
GB2025417B (en)	1983-03-02
FR2438649B1 (fr)	1983-03-25
FR2443457A1 (fr)	1980-07-04
FI792123A7 (fi)	1981-01-01
IT1122180B (it)	1986-04-23
BE877694A (fr)	1979-11-05
PT69909A (fr)	1979-08-01
FR2443457B1 (fr)	1983-09-23
GB2025417A (en)	1980-01-23
CA1127164A (fr)	1982-07-06
ATA483579A (de)	1982-02-15
JPS5943943B2 (ja)	1984-10-25
NO792329L (no)	1980-01-15
SE446631B (sv)	1986-09-29
JPS5533467A (en)	1980-03-08
DK293779A (da)	1980-01-14
AT368491B (de)	1982-10-11
FR2438649A1 (fr)	1980-05-09
ZA793554B (en)	1980-06-25
LU79970A1 (fr)	1980-02-14
CH644355A5 (fr)	1984-07-31
SE7905992L (sv)	1980-01-14
NO148452B (no)	1983-07-04
IT7924357A0 (it)	1979-07-13
ES482432A1 (es)	1980-04-01
NO148452C (no)	1983-10-12
DE2927789A1 (de)	1980-01-24

Legal Events

Date	Code	Title	Description
1980-05-27	BA	A request for search or an international-type search has been filed
1981-03-25	BB	A search report has been drawn up
1981-08-03	BC	A request for examination has been filed
1985-01-01	A85	Still pending on 85-01-01
1985-05-17	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: CONTINENTAL PHARMA, INC.
1987-03-02	BI	The patent application has been withdrawn

Publication	Publication Date	Title
CS20192A3 (en)	1992-08-12	Amino acid derivatives, process of their preparation and use
JPH07504654A (ja)	1995-05-25	オキソ及びヒドロキシ置換炭化水素のアミン誘導体
US6563009B1 (en)	2003-05-13	Vasodilator cannabinoid analogs
CA2412368A1 (fr)	2002-02-14	Derives de benzimidazole, leur preparation et leur application en therapeutique
MC1639A1 (fr)	1986-01-09	Derives de la glycerine
JPH11501920A (ja)	1999-02-16	ヘテロシクロカルボニルアミノ酸ヒドロキシエチルアミノスルホンアミドレトロウイルスプロテアーゼインヒビター
ES2220043T3 (es)	2004-12-01	Derivados del indol y composiciones medicinales que los contienen.
EP3237384A1 (fr)	2017-11-01	Nouveaux composés antagonistes des récepteurs cxcr1 et cxcr2 aux chimiokines, et leur utilisation dans le traitement de pathologies médiées par des chimiokines
EP0341231B1 (fr)	1992-11-19	1-(1H-imidazol-4-yl)alkyl-benzamides substitués
KR840001552B1 (ko)	1984-10-05	시클로헥센 유도체의 제조방법
CA2110273C (fr)	2002-02-12	Composes derives de benzimidazole, leur procede de preparation et leur utilisation dans les domaines therapeutique et cosmetique
JPS6326099B2 (fr)	1988-05-27
FR2626175A1 (fr)	1989-07-28	Composes nouveaux de 1,2-ethylenediamine et composition pharmaceutique les contenant
FR2560195A1 (fr)	1985-08-30	Derives d'alanyl-proline, leur procede de preparation et leurs applications pharmaceutiques
EP0141222A1 (fr)	1985-05-15	Ester cyclique de l'acide dihydropyridine-phosphonique-5
CH644355A5 (fr)	1984-07-31	Derives de 1-phenyl-1-propanol.
EP1021442A1 (fr)	2000-07-26	Derives de 8-azabicyclo 3.2.1] octane-3-methanamine en tant que ligands des recepteurs de dopamine d2 et d3 et de serotonine 5ht1a et 5ht2
JPS6341460A (ja)	1988-02-22	新規なジヒドロピリジン誘導体
CA2027602A1 (fr)	1991-05-14	Derives pharmaceutiques de l'epinephrine-pilocarpine
EP0301936A1 (fr)	1989-02-01	Dérivés de pipéridine, leur préparation et leur application en thérapeutique
CH635570A5 (fr)	1983-04-15	Derives d'amino-alcools.
CA2151503C (fr)	1999-07-20	Derives du 2,3-dihydrobenzofurane
EP0215319A2 (fr)	1987-03-25	Gem-dihalo diamino-1,8 aza-4 octanes
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