NL8002567A - Fenylethylaminederivaten, werkwijzen ter bereiding ervan, preparaten die de nieuwe derivaten bevatten, alsmede werkwijzen ter bereiding daarvan. - Google Patents

Fenylethylaminederivaten, werkwijzen ter bereiding ervan, preparaten die de nieuwe derivaten bevatten, alsmede werkwijzen ter bereiding daarvan. Download PDF

Info

Publication number: NL8002567A
Authority: NL; Netherlands
Prior art keywords: group; carbon atoms; formula; phenoxy; alkyl group
Prior art date: 1979-05-04

Application number

NL8002567A

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.)

1979-05-04

Filing date

1980-05-02

Publication date

1980-11-06

1980-05-02 Application filed by Continental Pharma filed Critical Continental Pharma

1980-11-06 Publication of NL8002567A publication Critical patent/NL8002567A/nl

Links

238000000034 method Methods 0.000 title claims description 54
238000002360 preparation method Methods 0.000 title claims description 16
150000007925 phenylethylamine derivatives Chemical class 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 98
125000004432 carbon atom Chemical group C* 0.000 claims description 94
125000000217 alkyl group Chemical group 0.000 claims description 72
-1 methylenedioxy group Chemical group 0.000 claims description 65
238000006243 chemical reaction Methods 0.000 claims description 59
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
230000008569 process Effects 0.000 claims description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
229910052794 bromium Inorganic materials 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
230000009467 reduction Effects 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 9
238000006467 substitution reaction Methods 0.000 claims description 9
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
150000002466 imines Chemical class 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000005518 carboxamido group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
238000001149 thermolysis Methods 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
XRTUHKHYQYDWAL-UHFFFAOYSA-N N-[1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propan-2-yl]octanamide Chemical compound C(CCCCCCC)(=O)NC(CC1=CC=C(OCC(CNC(C)C)O)C=C1)C XRTUHKHYQYDWAL-UHFFFAOYSA-N 0.000 claims description 2
SFJCSRMERHPRAK-UHFFFAOYSA-N N-[5-amino-4-hydroxy-5-[4-[2-(octylamino)ethyl]phenoxy]pentyl]-2-phenylacetamide Chemical compound C(CCCCCCC)NCCC1=CC=C(OC(C(CCCNC(CC2=CC=CC=C2)=O)O)N)C=C1 SFJCSRMERHPRAK-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
125000005596 alkyl carboxamido group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
229940093471 ethyl oleate Drugs 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000008223 sterile water Substances 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
239000006188 syrup Substances 0.000 claims description 2
235000020357 syrup Nutrition 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
241001331845 Equus asinus x caballus Species 0.000 claims 1
ZYTPOUNUXRBYGW-YUMQZZPRSA-N Met-Met Chemical compound CSCC[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CCSC ZYTPOUNUXRBYGW-YUMQZZPRSA-N 0.000 claims 1
UOPWBXMAPMSNBL-UHFFFAOYSA-N N-[5-amino-4-hydroxy-5-[4-[2-(octylamino)ethyl]phenoxy]pentyl]-2-methylpropanamide Chemical compound C(CCCCCCC)NCCC1=CC=C(OC(C(CCCNC(C(C)C)=O)O)N)C=C1 UOPWBXMAPMSNBL-UHFFFAOYSA-N 0.000 claims 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 claims 1
125000000068 chlorophenyl group Chemical group 0.000 claims 1
239000008298 dragée Substances 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
108010085203 methionylmethionine Proteins 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000003826 tablet Substances 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
230000007306 turnover Effects 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
230000000694 effects Effects 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 28
239000000047 product Substances 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
230000002829 reductive effect Effects 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
230000005764 inhibitory process Effects 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
229960004592 isopropanol Drugs 0.000 description 15
238000012360 testing method Methods 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
208000010110 spontaneous platelet aggregation Diseases 0.000 description 13
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000003960 organic solvent Substances 0.000 description 11
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
229960001138 acetylsalicylic acid Drugs 0.000 description 9
239000002585 base Substances 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
238000011282 treatment Methods 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
230000016571 aggressive behavior Effects 0.000 description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000011707 mineral Substances 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 5
229930008281 A03AD01 - Papaverine Natural products 0.000 description 5
102000008186 Collagen Human genes 0.000 description 5
108010035532 Collagen Proteins 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
230000009471 action Effects 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
230000000903 blocking effect Effects 0.000 description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
229920001436 collagen Polymers 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
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230000002093 peripheral effect Effects 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
241000700199 Cavia porcellus Species 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
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108010020828 Thrombofax Proteins 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
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229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
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230000000304 vasodilatating effect Effects 0.000 description 4
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 3
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238000007796 conventional method Methods 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
- 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Neurology (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Hematology (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Obesity (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

NL8002567A 1979-05-04 1980-05-02 Fenylethylaminederivaten, werkwijzen ter bereiding ervan, preparaten die de nieuwe derivaten bevatten, alsmede werkwijzen ter bereiding daarvan. NL8002567A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU81225		1979-05-04
LU81225		1979-05-04

Publications (1)

Publication Number	Publication Date
NL8002567A true NL8002567A (nl)	1980-11-06

Family

ID=19729148

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NL8002567A NL8002567A (nl)	1979-05-04	1980-05-02	Fenylethylaminederivaten, werkwijzen ter bereiding ervan, preparaten die de nieuwe derivaten bevatten, alsmede werkwijzen ter bereiding daarvan.
NL8002568A NL8002568A (nl)	1979-05-04	1980-05-02	Benzimidazoolderivaten, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de benzimida- zoolderivaten bevatten, alsmede werkwijzen ter bereiding van farmaceutische preparaten.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NL8002568A NL8002568A (nl)	1979-05-04	1980-05-02	Benzimidazoolderivaten, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de benzimida- zoolderivaten bevatten, alsmede werkwijzen ter bereiding van farmaceutische preparaten.

Country Status (22)

Country	Link
US (1)	US4338330A (de)
JP (2)	JPS565465A (de)
AT (2)	AT376418B (de)
AU (2)	AU542596B2 (de)
BE (2)	BE883069A (de)
CA (1)	CA1146563A (de)
CH (2)	CH644599A5 (de)
DE (2)	DE3016828A1 (de)
DK (2)	DK187880A (de)
ES (2)	ES491143A0 (de)
FI (2)	FI801428A7 (de)
FR (2)	FR2455587A1 (de)
GB (2)	GB2055091B (de)
GR (2)	GR68536B (de)
IE (1)	IE50218B1 (de)
IL (2)	IL59974A0 (de)
IT (2)	IT1150018B (de)
NL (2)	NL8002567A (de)
NO (2)	NO801286L (de)
PT (2)	PT71174A (de)
SE (2)	SE8003277L (de)
ZA (2)	ZA802695B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
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CA1156661A (en) *	1980-02-25	1983-11-08	Hoffmann-La Roche Limited	Phenoxy-aminopropanol derivatives
JPS582343A (ja) *	1981-06-30	1983-01-07	Osaka Soda Co Ltd	耐窒素酸化物性に優れた加硫性ゴム組成物
GB8310556D0 (en) *	1983-04-19	1983-05-25	Beecham Group Plc	Compounds
US4550119A (en) *	1983-05-23	1985-10-29	Warner-Lambert Company	2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones
US5104892A (en) *	1989-12-11	1992-04-14	American Home Products Corporation	Substituted benzimidazole derivatives possessing Class III antiarrhythmic activity
US5541204A (en) *	1994-12-02	1996-07-30	Bristol-Myers Squibb Company	Aryloxypropanolamine β 3 adrenergic agonists
CA2479338A1 (en) *	2002-03-20	2003-10-02	Metabolex, Inc.	Substituted phenylacetic acids
US7351719B2 (en)	2002-10-31	2008-04-01	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds
US7199259B2 (en) *	2003-06-20	2007-04-03	Metabolex, Inc.	Resolution of α-(phenoxy)phenylacetic acid derivatives
EP1749000A4 (de) *	2004-05-25	2009-12-30	Metabolex Inc	Bicyclische substituierte triazole als ppar-modulatoren und verfahren zu deren herstellung
AU2005247473A1 (en) *	2004-05-25	2005-12-08	Metabolex, Inc.	Substituted triazoles as modulators of PPAR and methods of their preparation
US7714131B2 (en) *	2005-09-23	2010-05-11	Metabolex, Inc.	Process for the stereoselective preparation of (−)-halofenate and derivatives thereof
EP2727911B1 (de) *	2012-10-31	2016-12-21	Medizinische Hochschule Hannover	Neuartiges Mittel und neuartige Verfahren zur Behandlung von Malaria und anderen parasitären Krankheiten

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1157556A (en) *	1966-06-09	1969-07-09	Egyt Gyogyszervegyeszeti Gyar	Novel Benzazole Derivatives and the Preparation thereof
FR1570892A (de) *	1968-06-18	1969-06-13
US3574218A (en) *	1969-08-11	1971-04-06	Egyt Gyogyszervegyeszeti Gyar	2-aryl- or aralkyl-substituted benzazole derivatives
JPS5231858B1 (de) *	1969-12-17	1977-08-17
CH624395A5 (de)	1976-01-08	1981-07-31	Ciba Geigy Ag
DE2609645A1 (de)	1976-03-09	1977-09-15	Boehringer Sohn Ingelheim	Aminoalkylheterocyclen
DE2640730C2 (de) *	1976-09-10	1983-08-25	Hoechst Ag, 6230 Frankfurt	Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel
DE2644833A1 (de) *	1976-10-05	1978-04-20	Boehringer Sohn Ingelheim	Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung
DE2737630A1 (de)	1977-08-20	1979-03-01	Boehringer Mannheim Gmbh	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2801953A1 (de)	1978-01-18	1979-07-19	Boehringer Mannheim Gmbh	4-hydroxy-2-benzimidazolinon-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
DE2801980A1 (de)	1978-01-18	1979-07-19	Boehringer Mannheim Gmbh	4-hydroxy-2-benzimidazolin-thion- derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
EP0003758A1 (de)	1978-02-09	1979-09-05	Ciba-Geigy Ag	Verätherte Hydroxy-benzodiheterocyclen und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE2905876A1 (de)	1979-02-16	1980-08-28	Boehringer Mannheim Gmbh	Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2905877A1 (de)	1979-02-16	1980-08-28	Boehringer Mannheim Gmbh	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1980
- 1980-04-30 PT PT71174A patent/PT71174A/pt unknown
- 1980-04-30 US US06/145,144 patent/US4338330A/en not_active Expired - Lifetime
- 1980-04-30 BE BE0/200433A patent/BE883069A/fr not_active IP Right Cessation
- 1980-04-30 SE SE8003277A patent/SE8003277L/xx not_active Application Discontinuation
- 1980-04-30 SE SE8003278A patent/SE8003278L/xx not_active Application Discontinuation
- 1980-04-30 PT PT71175A patent/PT71175A/pt unknown
- 1980-04-30 FR FR8009847A patent/FR2455587A1/fr active Granted
- 1980-04-30 DK DK187880A patent/DK187880A/da not_active Application Discontinuation
- 1980-04-30 FR FR8009846A patent/FR2455572B1/fr not_active Expired
- 1980-04-30 DK DK187980A patent/DK187980A/da not_active Application Discontinuation
- 1980-04-30 BE BE0/200432A patent/BE883068A/fr not_active IP Right Cessation
- 1980-05-01 IL IL59974A patent/IL59974A0/xx unknown
- 1980-05-01 IL IL59973A patent/IL59973A/xx unknown
- 1980-05-02 FI FI801428A patent/FI801428A7/fi not_active Application Discontinuation
- 1980-05-02 CH CH345380A patent/CH644599A5/fr not_active IP Right Cessation
- 1980-05-02 CH CH345280A patent/CH645090A5/fr not_active IP Right Cessation
- 1980-05-02 FI FI801429A patent/FI801429A7/fi not_active Application Discontinuation
- 1980-05-02 NL NL8002567A patent/NL8002567A/nl not_active Application Discontinuation
- 1980-05-02 NO NO801286A patent/NO801286L/no unknown
- 1980-05-02 ES ES491143A patent/ES491143A0/es active Granted
- 1980-05-02 CA CA000351169A patent/CA1146563A/en not_active Expired
- 1980-05-02 NO NO801285A patent/NO150916C/no unknown
- 1980-05-02 GB GB8014645A patent/GB2055091B/en not_active Expired
- 1980-05-02 IT IT8021779A patent/IT1150018B/it active
- 1980-05-02 ES ES491142A patent/ES491142A0/es active Granted
- 1980-05-02 DE DE19803016828 patent/DE3016828A1/de not_active Withdrawn
- 1980-05-02 NL NL8002568A patent/NL8002568A/nl not_active Application Discontinuation
- 1980-05-02 GR GR61836A patent/GR68536B/el unknown
- 1980-05-02 DE DE19803016827 patent/DE3016827A1/de not_active Withdrawn
- 1980-05-02 GR GR61835A patent/GR68535B/el unknown
- 1980-05-02 GB GB8014647A patent/GB2055360B/en not_active Expired
- 1980-05-02 IT IT8021780A patent/IT1159060B/it active
- 1980-05-05 AU AU58096/80A patent/AU542596B2/en not_active Ceased
- 1980-05-05 ZA ZA00802695A patent/ZA802695B/xx unknown
- 1980-05-05 AT AT0238680A patent/AT376418B/de not_active IP Right Cessation
- 1980-05-05 AT AT0238780A patent/AT376210B/de not_active IP Right Cessation
- 1980-05-05 IE IE918/80A patent/IE50218B1/en unknown
- 1980-05-05 AU AU58095/80A patent/AU537573B2/en not_active Ceased
- 1980-05-05 ZA ZA00802694A patent/ZA802694B/xx unknown
- 1980-05-06 JP JP5984680A patent/JPS565465A/ja active Pending
- 1980-05-06 JP JP55059847A patent/JPS6033424B2/ja not_active Expired

Also Published As

Publication number	Publication date
NO150916C (no)	1985-01-16
FR2455572A1 (fr)	1980-11-28
IT1159060B (it)	1987-02-25
IL59973A (en)	1985-03-31
IL59974A0 (en)	1980-07-31
CA1146563A (en)	1983-05-17
ZA802694B (en)	1981-08-26
GB2055091B (en)	1983-11-09
IT8021780A1 (it)	1981-11-02
JPS565465A (en)	1981-01-20
JPS5663946A (en)	1981-05-30
PT71174A (fr)	1980-05-01
CH644599A5 (fr)	1984-08-15
GB2055091A (en)	1981-02-25
ZA802695B (en)	1981-08-26
AU542596B2 (en)	1985-02-28
GR68536B (de)	1982-01-18
ES8104245A1 (es)	1981-04-16
FI801428A7 (fi)	1980-11-05
AT376210B (de)	1984-10-25
DK187980A (da)	1980-11-05
AU5809680A (en)	1980-11-06
IT1150018B (it)	1986-12-10
IE50218B1 (en)	1986-03-05
FR2455587B1 (de)	1983-06-24
IT8021780A0 (it)	1980-05-02
SE8003278L (sv)	1980-11-05
NO150916B (no)	1984-10-01
IL59973A0 (en)	1980-07-31
BE883069A (fr)	1980-08-18
NO801286L (no)	1980-11-05
DK187880A (da)	1980-11-05
PT71175A (fr)	1980-05-01
IE800918L (en)	1980-11-04
DE3016828A1 (de)	1980-11-13
GR68535B (de)	1982-01-18
JPS6033424B2 (ja)	1985-08-02
SE8003277L (sv)	1980-11-05
AU537573B2 (en)	1984-07-05
ES8103729A1 (es)	1981-03-16
GB2055360B (en)	1983-07-06
ATA238680A (de)	1984-04-15
FI801429A7 (fi)	1980-11-05
IT8021779A0 (it)	1980-05-02
ES491142A0 (es)	1981-03-16
NO801285L (no)	1980-11-05
AU5809580A (en)	1980-11-06
IT8021779A1 (it)	1981-11-02
FR2455587A1 (fr)	1980-11-28
GB2055360A (en)	1981-03-04
ES491143A0 (es)	1981-04-16
US4338330A (en)	1982-07-06
BE883068A (fr)	1980-08-18
AT376418B (de)	1984-11-26
FR2455572B1 (fr)	1986-07-25
ATA238780A (de)	1984-03-15
CH645090A5 (fr)	1984-09-14
NL8002568A (nl)	1980-11-06
DE3016827A1 (de)	1980-11-20

Publication	Publication Date	Title
Crowther et al.	1968	. beta.-Adrenergic blocking agents. II. Propranolol and related 3-amino-1-naphthoxy-2-propanols
NL8002567A (nl)	1980-11-06	Fenylethylaminederivaten, werkwijzen ter bereiding ervan, preparaten die de nieuwe derivaten bevatten, alsmede werkwijzen ter bereiding daarvan.
JP2637737B2 (ja)	1997-08-06	新規な薬剤
CA1066282A (en)	1979-11-13	.beta.-ADRENERGIC RECEPTOR BLOCKING AGENTS
JPS62167752A (ja)	1987-07-24	フエニルアセトニトリル誘導体その医薬組成物および哺乳動物におけるカルシウムイオンきつ抗作用または抗高圧作用促進方法
NL8003601A (nl)	1981-01-13	Amino-etheroxyden, werkwijze voor de bereiding hiervan en de toepassing als geneesmiddel.
EP0030861A2 (de)	1981-06-24	Isochinolinessigsäuren und sie enthaltende pharmazeutische Zusammensetzungen
CH617697A5 (de)	1980-06-13
CH542177A (fr)	1973-09-30	Procédé de préparation d'amino-alcools et de leurs sels
CA1120945A (en)	1982-03-30	Esters of 1,1,2-triphenylalkene derivatives
DK159425B (da)	1990-10-15	5-acyl-3-cyano-2-(1h)-pyridinoner eller syreadditionssalte deraf
Yamato et al.	1981	Synthesis and structure-activity relationship of spiro [isochromanpiperidine] analogs for inhibition of histamine release. 1
EP0028959A1 (de)	1981-05-20	5,8,13,13a -Tetrahydro-6H-dibenzo(a,g)chinolizin-Derivate, Verfahren zur Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4515814A (en)	1985-05-07	3-Phenoxypropan-2-ol derivatives for treating glaucoma
US4490392A (en)	1984-12-25	Benzylalcohol derivative and process for preparing
BE854655A (fr)	1977-11-16	9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
Brown et al.	1985	Chiral synthesis of 3-substituted morpholines via serine enantiomers and reductions of 5-oxomorpholine-3-carboxylates
CH652119A5 (fr)	1985-10-31	Derives de l'acide guanidinocyclohexanecarboxylique et leur procede de fabrication.
US3969363A (en)	1976-07-13	Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their production
JPS584026B2 (ja)	1983-01-24	ピラジンユウドウタイオヨビセイホウ
EP0173634A1 (de)	1986-03-05	4-(Arylpiperazinylethylaminoethoxy)-phenolderivate, Verfahren zu deren Herstellung und deren therapeutische Verwendung
US4201790A (en)	1980-05-06	Benzophenone derivatives
FR2567754A1 (fr)	1986-01-24	Application therapeutique d'aminomethylene-2 indanediones-1,3 substituees sur l'azote
KR840002005B1 (ko)	1984-10-27	피페라진 유도체의 제조방법
EP0179009A1 (de)	1986-04-23	N-1(Aminoalcoxy)-4-isopropyl-5 phenoxy)-2 ethyl-N-4-phenylpiperazine, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung

Legal Events

Date	Code	Title	Description
1980-11-25	A1A	A request for search or an international-type search has been filed
1982-04-01	BB	A search report has been drawn up
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.
1985-07-01	BC	A request for examination has been filed
1988-01-04	BV	The patent application has lapsed