GB1308259A - Phenethylamine derivatives and a process for the manufacture thereof - Google Patents
Phenethylamine derivatives and a process for the manufacture thereofInfo
- Publication number
- GB1308259A GB1308259A GB4033671A GB1308259DA GB1308259A GB 1308259 A GB1308259 A GB 1308259A GB 4033671 A GB4033671 A GB 4033671A GB 1308259D A GB1308259D A GB 1308259DA GB 1308259 A GB1308259 A GB 1308259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- alkyl
- formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 o-nitrophenylthio group Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000003342 alkenyl group Chemical group 0.000 abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- 229910021538 borax Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000004328 sodium tetraborate Substances 0.000 abstract 4
- 235000010339 sodium tetraborate Nutrition 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 3
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001266 acyl halides Chemical class 0.000 abstract 2
- 150000001540 azides Chemical class 0.000 abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- SGRSNYSOAPBTJP-UHFFFAOYSA-N 4-(2-aminoethyl)benzene-1,2-diol;hydron;bromide Chemical compound Br.NCCC1=CC=C(O)C(O)=C1 SGRSNYSOAPBTJP-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1308259 3,4-Dihydroxyphenethylamine derivatives; borax complex F HOFFMANN-LA ROCHE & CO AG 29 Oct 1971 [30 Oct 1970] 50336/71 Headings C2B and C2C Novel compounds of Formula I wherein R 1 represents a hydrogen atom, an alkanoyl group which may be substituted by alkoxy or by phenyl which may, in turn, be alkoxy- or halo-substituted, a benzoyl group which may be alkoxy or halo-substituted, an alkenoyl group, an alkoxycarbonyl group which may be phenyl-substituted, an aminocarbonyl group which may be alkyl-substituted or the o-nitrophenylthio group and R 2 represents an alkanoyl group containing at least 4 carbon atoms which may be substituted by alkoxy or by phenyl which may, in turn, be alkoxy- or halo-substituted, a benzoyl group which may be alkoxy- or halo-substituted, an alkenoyl or alkoxycarbonyl group, an aminocarbonyl group which may be alkyl-substituted, an alkylsulphonyl group, an alkyl group which is substituted by alkenyl, alkynyl, alkoxyalkyl, cyano, carboxy, alkoxycarbonyl (which may be alkenyl-, alkynyl- or phenyl-substituted) or aminocarbonyl (which may be alkyl-substituted), provided that R 1 is different from R 2 and salts thereof, are prepared by one of the following methods; (A) a compound of Formula II wherein R<SP>1</SP> 1 has any value of R 1 except H is reacted with an acyl halide, acid anhydride or acid azide to furnish the group R 2 except where R 2 is carboxy alkyl or (B) reducing a compound of formula wherein R 2 has the significance given earlier and R 3 represents the 2-nitrovinyl or cyanomethyl group or a group of the formulµ in which R<SP>11</SP> 1 has any of the values accorded to R 1 hereinbefore except o - nitrophenylthio, benzyloxycarbonyl or t-alkoxycarbonyl and R 4 represents a hydroxy, lower alkoxy or phenylamino group, provided that when R 3 represents a 2-nitrovinyl or cyanomethyl group R 2 represents other than a halo-substituted phenylalkanoyl or halo-substituted benzoyl group, when R 3 represents the group (a) R 2 represents an alkyl group which is substituted by alkenyl, alkynyl, alkoxyalkyl, cyano, carboxy, alkoxycarbonyl (which may be alkenyl-, alkynyl- or phenyl-substituted) or aminocarbonyl (which may be alkyl-substituted), when R 3 represents the group (b) R 2 represents other than a cyanosubstituted alkyl group and when R 3 represents the group (c) R 2 represents other than an alkenyl-, alkynyl-, or cyano-substituted alkyl group, or (C) hydrolysing a compound of formula wherein R<SP>1</SP> 2 denotes any value of R 2 other than carboxyalkyl or treating it with an alkanol which may be phenyl-substituted or with ammonia or an alkylamine or dialkylamine, or (D) reacting a compound of formula or a salt thereof with an acyl halide, acid anhydride or acid azide to furnish the group R<SP>1</SP> 1 and, if desired, cleaving off a benzyloxycarbonyl group brand to the nitrogen atom of a compound of Formula I obtained by reduction or by treatment with hydrogen bromide or trifluoroacetic acid or cleaving- off a t-alkoxycarbonyl group or the o-nitrophenylthio group bound to the nitrogen atom of a compound of Formula I obtained by treatment with an acidic agent or cleaving off an acid group R 1 from a compound of Formula I obtained in which R 2 represents an alkyl group which is substituted by alkenyl, alkynyl, alkoxyalkyl, cyano, carboxy, alkoxycarbonyl (which may be alkenyl-, alkynyl- or phenyl-substituted) or aminocarbonyl (which may be alkyl-substituted) by hydrolysis, and, also if desired, converting a product obtained into a salt. Intermediates of Formula II above wherein R<SP>1</SP> 1 is benzyloxycarbonyl, t-butoxycarbonyl or acetyl are prepared by reacting carbobenzoxychloride, t-butoxycarbonyl hydrazide or acetic anhydride respectively with an aqueous alkaline solution of a complex of borax and 3,4-dihydroxyphenethylamine in which the two hydroxy groups are in effect esterified by the borax, the complex being formed by adding borax to an aqueous solution of dopamine hydrobromide and adjusting to pH 10 with sodium hydroxide. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having hypotensive antipyretic and anti- Parkinson activity comprise an above novel compound or salt and a pharmaceutical carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1604970A CH550771A (en) | 1970-10-30 | 1970-10-30 | PROCESS FOR THE PRODUCTION OF PHENAETHYLAMINE DERIVATIVES. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1308259A true GB1308259A (en) | 1973-02-28 |
Family
ID=4414071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4033671A Expired GB1308259A (en) | 1970-10-30 | 1971-10-29 | Phenethylamine derivatives and a process for the manufacture thereof |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU3427171A (en) |
| BE (1) | BE774679A (en) |
| CH (1) | CH550771A (en) |
| DE (1) | DE2153801A1 (en) |
| FR (1) | FR2111946B1 (en) |
| GB (1) | GB1308259A (en) |
| IL (1) | IL37843A0 (en) |
| NL (1) | NL7114428A (en) |
| ZA (1) | ZA716516B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2391997A1 (en) * | 1977-05-23 | 1978-12-22 | Ici Ltd | NEW DERIVATIVES OF ALCANOLAMINES, THEIR PREPARATION PROCESS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
| EP1032559A1 (en) * | 1997-09-29 | 2000-09-06 | Aventis Pharmaceuticals Inc. | Aminoalkylphenol derivatives and related compounds |
| WO2007060886A1 (en) * | 2005-11-24 | 2007-05-31 | National University Corporation Hokkaido University | Therapeutic agent for neurodegenerative disease |
| JP2020040949A (en) * | 2017-12-28 | 2020-03-19 | テックフィールズ ファーマ カンパニー リミテッド | Novel high penetration drugs and compositions thereof for treatment of parkinson's disease |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275219A (en) * | 1979-09-24 | 1981-06-23 | Interx Research Corporation | Novel process and intermediates useful in the preparation of sympathomimetic amines |
| DE3163871D1 (en) | 1980-07-09 | 1984-07-05 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates |
| US4338455A (en) * | 1981-02-11 | 1982-07-06 | Merck & Co., Inc. | Novel process and intermediates useful in the preparation of sympathomimetic amines |
| US4454337A (en) * | 1981-06-29 | 1984-06-12 | Smithkline Beckman Corporation | Semicarbazide intermediates for preparing 4-substituted indoles |
| US4443473A (en) * | 1981-06-30 | 1984-04-17 | The Procter & Gamble Company | Carbamate derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE562714C (en) * | 1931-01-06 | 1932-10-28 | Karl Kindler Dr | Process for the preparation of primary ª ‰ -arylaethylamines from amides of hydrocinnamic acids |
-
1970
- 1970-10-30 CH CH1604970A patent/CH550771A/en not_active IP Right Cessation
-
1971
- 1971-09-28 ZA ZA716516A patent/ZA716516B/en unknown
- 1971-10-05 IL IL37843A patent/IL37843A0/en unknown
- 1971-10-06 AU AU34271/71A patent/AU3427171A/en not_active Expired
- 1971-10-20 NL NL7114428A patent/NL7114428A/xx unknown
- 1971-10-28 FR FR7138777A patent/FR2111946B1/fr not_active Expired
- 1971-10-28 DE DE19712153801 patent/DE2153801A1/en active Pending
- 1971-10-29 GB GB4033671A patent/GB1308259A/en not_active Expired
- 1971-10-29 BE BE774679A patent/BE774679A/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2391997A1 (en) * | 1977-05-23 | 1978-12-22 | Ici Ltd | NEW DERIVATIVES OF ALCANOLAMINES, THEIR PREPARATION PROCESS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
| EP1032559A1 (en) * | 1997-09-29 | 2000-09-06 | Aventis Pharmaceuticals Inc. | Aminoalkylphenol derivatives and related compounds |
| EP1032559A4 (en) * | 1997-09-29 | 2005-05-25 | Aventis Pharma Inc | Aminoalkylphenol derivatives and related compounds |
| WO2007060886A1 (en) * | 2005-11-24 | 2007-05-31 | National University Corporation Hokkaido University | Therapeutic agent for neurodegenerative disease |
| EP1974732A1 (en) * | 2005-11-24 | 2008-10-01 | National University Corporation Hokkaido University | Therapeutic agent for neurodegenerative disease |
| EP1974732A4 (en) * | 2005-11-24 | 2010-08-11 | Univ Hokkaido Nat Univ Corp | Therapeutic agent for neurodegenerative disease |
| US8318798B2 (en) | 2005-11-24 | 2012-11-27 | National University Corporation Hokkaldo University | Therapeutic agent for neurodegenerative disease |
| JP2020040949A (en) * | 2017-12-28 | 2020-03-19 | テックフィールズ ファーマ カンパニー リミテッド | Novel high penetration drugs and compositions thereof for treatment of parkinson's disease |
| JP2022020671A (en) * | 2017-12-28 | 2022-02-01 | テックフィールズ ファーマ カンパニー リミテッド | Novel high penetration drugs and compositions thereof for treatment of parkinson's disease |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2153801A1 (en) | 1972-05-04 |
| CH550771A (en) | 1974-06-28 |
| FR2111946A1 (en) | 1972-06-09 |
| BE774679A (en) | 1972-05-02 |
| FR2111946B1 (en) | 1975-08-01 |
| ZA716516B (en) | 1972-10-25 |
| AU3427171A (en) | 1973-04-12 |
| NL7114428A (en) | 1972-05-03 |
| IL37843A0 (en) | 1971-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |