CH556323A - Verfahren zur herstellung von neuen naphthylalkylaminen. - Google Patents
Verfahren zur herstellung von neuen naphthylalkylaminen.Info
- Publication number
- CH556323A CH556323A CH477673A CH477673A CH556323A CH 556323 A CH556323 A CH 556323A CH 477673 A CH477673 A CH 477673A CH 477673 A CH477673 A CH 477673A CH 556323 A CH556323 A CH 556323A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen atom
- formula
- radical
- lower alkyl
- acid addition
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- -1 alkylene radical Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims 1
- 239000003908 antipruritic agent Substances 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000000043 antiallergic agent Substances 0.000 abstract 1
- 230000000572 bronchospasmolytic effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 229940124549 vasodilator Drugs 0.000 abstract 1
- 239000003071 vasodilator agent Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical group CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- VTSPJLHFXSMCCC-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-2-(2-ethylimidazol-1-yl)ethanone;hydrochloride Chemical compound Cl.CCC1=NC=CN1CC(=O)C1=CC=C(O)C(O)=C1 VTSPJLHFXSMCCC-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- VEYCCHNUJNXSRR-UHFFFAOYSA-N 4-naphthalen-1-ylbutan-2-one Chemical compound C1=CC=C2C(CCC(=O)C)=CC=CC2=C1 VEYCCHNUJNXSRR-UHFFFAOYSA-N 0.000 description 1
- VZVBXISLBQEWKU-UHFFFAOYSA-N 5-(2-amino-1-hydroxyethyl)benzene-1,3-diol Chemical compound NCC(O)C1=CC(O)=CC(O)=C1 VZVBXISLBQEWKU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LPDOGIKTLWZIOL-UHFFFAOYSA-N OC1=CC=C(C=C1)C(CNC(CC1=CC=C(C2=CC=CC=C12)O)C)O Chemical compound OC1=CC=C(C=C1)C(CNC(CC1=CC=C(C2=CC=CC=C12)O)C)O LPDOGIKTLWZIOL-UHFFFAOYSA-N 0.000 description 1
- PLULGMYUFGQQLZ-UHFFFAOYSA-N OC=1C=C(C=C(C=1)O)C(CNC(C)CCC1=CC=CC2=CC=CC=C12)O Chemical compound OC=1C=C(C=C(C=1)O)C(CNC(C)CCC1=CC=CC2=CC=CC=C12)O PLULGMYUFGQQLZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001139 anti-pruritic effect Effects 0.000 description 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- VQXINLNPICQTLR-UHFFFAOYSA-N carbonyl diazide Chemical class [N-]=[N+]=NC(=O)N=[N+]=[N-] VQXINLNPICQTLR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical compound NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-BKFZFHPZSA-N platinum-200 Chemical compound [200Pt] BASFCYQUMIYNBI-BKFZFHPZSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962497A DE1962497C3 (de) | 1969-12-12 | 1969-12-12 | Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel |
| CH1818970A CH556322A (de) | 1969-12-12 | 1970-12-09 | Verfahren zur herstellung von neuen naphthylalkylaminen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH556323A true CH556323A (de) | 1974-11-29 |
Family
ID=25720616
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH477673A CH556323A (de) | 1969-12-12 | 1970-12-09 | Verfahren zur herstellung von neuen naphthylalkylaminen. |
| CH477773A CH564509A5 (enrdf_load_stackoverflow) | 1969-12-12 | 1970-12-09 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH477773A CH564509A5 (enrdf_load_stackoverflow) | 1969-12-12 | 1970-12-09 |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH556323A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2039646T3 (es) * | 1987-11-13 | 1993-10-01 | Glaxo Group Limited | Derivados de fenetanolamina. |
| US20100168245A1 (en) | 2006-08-10 | 2010-07-01 | Wainer Irving W | Preparation of (r,r)-fenoterol and (r,r)-or (r,s)-fenoterol analogues and their use in treating congestive heart failure |
| AU2011224241B2 (en) | 2010-03-10 | 2014-05-08 | Sri International | The use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas |
-
1970
- 1970-12-09 CH CH477673A patent/CH556323A/de not_active IP Right Cessation
- 1970-12-09 CH CH477773A patent/CH564509A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH564509A5 (enrdf_load_stackoverflow) | 1975-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |