FI83635C - Foerfarande foer framstaellning av 2 -hydroxi-5 1-hydroxi-2-/(1-metyl-3-fenylpropyl)-amino/etyl bensamid och dess farmaceutiskt laempliga syraadditionssalt. - Google Patents
Foerfarande foer framstaellning av 2 -hydroxi-5 1-hydroxi-2-/(1-metyl-3-fenylpropyl)-amino/etyl bensamid och dess farmaceutiskt laempliga syraadditionssalt. Download PDFInfo
- Publication number
- FI83635C FI83635C FI850229A FI850229A FI83635C FI 83635 C FI83635 C FI 83635C FI 850229 A FI850229 A FI 850229A FI 850229 A FI850229 A FI 850229A FI 83635 C FI83635 C FI 83635C
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- formula
- benzamide
- compound
- ethyl
- Prior art date
Links
- -1 (1-METHYL-3-PHENYLPROPYL) -AMINO Chemical class 0.000 title claims description 18
- BJISZDCMBMQNIY-UHFFFAOYSA-N benzene Chemical compound [C-]1=CC=CC=C1 BJISZDCMBMQNIY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 10
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims description 9
- 238000011065 in-situ storage Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 238000002955 isolation Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- BWHOZHOGCMHOBV-UHFFFAOYSA-N benzylideneacetone Chemical compound CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- WOEISFSYHVAQTR-UHFFFAOYSA-N 5-(2-amino-1-hydroxyethyl)-2-hydroxybenzamide Chemical compound NCC(O)C1=CC=C(O)C(C(N)=O)=C1 WOEISFSYHVAQTR-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WQVZLXWQESQGIF-UHFFFAOYSA-N Labetalol hydrochloride Chemical compound Cl.C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 WQVZLXWQESQGIF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007040 multi-step synthesis reaction Methods 0.000 description 2
- ZASBYHZJHQFLGN-UHFFFAOYSA-N n-benzyl-4-phenylbutan-2-amine Chemical compound C=1C=CC=CC=1CNC(C)CCC1=CC=CC=C1 ZASBYHZJHQFLGN-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LWAQTCWTCCNHJR-UHFFFAOYSA-N 5-acetyl-2-hydroxybenzamide Chemical compound CC(=O)C1=CC=C(O)C(C(N)=O)=C1 LWAQTCWTCCNHJR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- XNBPIZTUCVHIFW-UHFFFAOYSA-N CC(=O)C=CC1=CC=CC=C1.CC(=O)C=CC1=CC=CC=C1 Chemical compound CC(=O)C=CC1=CC=CC=C1.CC(=O)C=CC1=CC=CC=C1 XNBPIZTUCVHIFW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QMFLJLLJCJKVFL-UHFFFAOYSA-N N-[2-[benzyl(4-phenylbutan-2-yl)amino]acetyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC(CN(C(CCC1=CC=CC=C1)C)CC1=CC=CC=C1)=O QMFLJLLJCJKVFL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- CJJZCWJJAZMVCJ-UHFFFAOYSA-N n-benzyl-2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(NCC=2C=CC=CC=2)=C1 CJJZCWJJAZMVCJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU23484 | 1984-01-20 | ||
| HU23484A HU190867B (en) | 1984-01-20 | 1984-01-20 | Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI850229A0 FI850229A0 (fi) | 1985-01-18 |
| FI850229L FI850229L (fi) | 1985-07-21 |
| FI83635B FI83635B (fi) | 1991-04-30 |
| FI83635C true FI83635C (fi) | 1991-08-12 |
Family
ID=10948617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI850229A FI83635C (fi) | 1984-01-20 | 1985-01-18 | Foerfarande foer framstaellning av 2 -hydroxi-5 1-hydroxi-2-/(1-metyl-3-fenylpropyl)-amino/etyl bensamid och dess farmaceutiskt laempliga syraadditionssalt. |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS60231639A (cs) |
| AT (1) | AT390612B (cs) |
| CA (1) | CA1239938A (cs) |
| CH (1) | CH662810A5 (cs) |
| CS (1) | CS249536B2 (cs) |
| DD (1) | DD228245A5 (cs) |
| DE (1) | DE3501582A1 (cs) |
| DK (1) | DK26185A (cs) |
| ES (1) | ES8608481A1 (cs) |
| FI (1) | FI83635C (cs) |
| FR (1) | FR2558465B1 (cs) |
| GB (1) | GB2152931B (cs) |
| HU (1) | HU190867B (cs) |
| NL (1) | NL8500119A (cs) |
| NO (1) | NO165918C (cs) |
| PT (1) | PT79844B (cs) |
| SE (1) | SE8500236L (cs) |
| SU (1) | SU1521281A3 (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1247370A (en) * | 1968-12-31 | 1971-09-22 | Allen & Hanburys Ltd | Glyoxals and production thereof |
| ZA794872B (en) * | 1978-09-20 | 1980-11-26 | Schering Corp | A phenylalkylaminoethylsalicylamide,its preparation and pharmaceutical compositions containing it |
-
1984
- 1984-01-20 HU HU23484A patent/HU190867B/hu not_active IP Right Cessation
- 1984-12-17 CH CH598584A patent/CH662810A5/de not_active IP Right Cessation
-
1985
- 1985-01-18 GB GB08501246A patent/GB2152931B/en not_active Expired
- 1985-01-18 DK DK26185A patent/DK26185A/da not_active Application Discontinuation
- 1985-01-18 FR FR8500702A patent/FR2558465B1/fr not_active Expired
- 1985-01-18 PT PT7984485A patent/PT79844B/pt unknown
- 1985-01-18 AT AT11685A patent/AT390612B/de not_active IP Right Cessation
- 1985-01-18 SU SU853837675A patent/SU1521281A3/ru active
- 1985-01-18 NL NL8500119A patent/NL8500119A/nl not_active Application Discontinuation
- 1985-01-18 ES ES540121A patent/ES8608481A1/es not_active Expired
- 1985-01-18 FI FI850229A patent/FI83635C/fi not_active IP Right Cessation
- 1985-01-18 CS CS37785A patent/CS249536B2/cs unknown
- 1985-01-18 DD DD27264985A patent/DD228245A5/de not_active IP Right Cessation
- 1985-01-18 NO NO850225A patent/NO165918C/no unknown
- 1985-01-18 DE DE19853501582 patent/DE3501582A1/de not_active Withdrawn
- 1985-01-18 CA CA000472445A patent/CA1239938A/en not_active Expired
- 1985-01-18 JP JP597885A patent/JPS60231639A/ja active Pending
- 1985-06-06 SE SE8500236A patent/SE8500236L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUT36779A (en) | 1985-10-28 |
| GB8501246D0 (en) | 1985-02-20 |
| CA1239938A (en) | 1988-08-02 |
| AT390612B (de) | 1990-06-11 |
| SU1521281A3 (ru) | 1989-11-07 |
| FI850229L (fi) | 1985-07-21 |
| CS249536B2 (en) | 1987-03-12 |
| GB2152931B (en) | 1987-03-18 |
| ES8608481A1 (es) | 1986-07-16 |
| PT79844B (en) | 1986-10-23 |
| FR2558465A1 (fr) | 1985-07-26 |
| DE3501582A1 (de) | 1985-08-01 |
| SE8500236D0 (sv) | 1985-01-18 |
| HU190867B (en) | 1986-11-28 |
| PT79844A (en) | 1985-02-01 |
| NO165918C (no) | 1991-05-02 |
| DK26185A (da) | 1985-07-21 |
| FR2558465B1 (fr) | 1988-08-26 |
| ES540121A0 (es) | 1986-07-16 |
| DK26185D0 (da) | 1985-01-18 |
| JPS60231639A (ja) | 1985-11-18 |
| SE8500236L (sv) | 1985-07-21 |
| CH662810A5 (de) | 1987-10-30 |
| FI83635B (fi) | 1991-04-30 |
| DD228245A5 (de) | 1985-10-09 |
| NO165918B (no) | 1991-01-21 |
| ATA11685A (de) | 1989-11-15 |
| NO850225L (no) | 1985-07-22 |
| NL8500119A (nl) | 1985-08-16 |
| GB2152931A (en) | 1985-08-14 |
| FI850229A0 (fi) | 1985-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: EGIS GYOGYSZERGYAR |