US3055906A - Pyridylethylated d-alpha-methylphenethylamines - Google Patents
Pyridylethylated d-alpha-methylphenethylamines Download PDFInfo
- Publication number
- US3055906A US3055906A US63462A US6346260A US3055906A US 3055906 A US3055906 A US 3055906A US 63462 A US63462 A US 63462A US 6346260 A US6346260 A US 6346260A US 3055906 A US3055906 A US 3055906A
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- United States
- Prior art keywords
- compound
- pyridylethylated
- methylphenethylamines
- pyridyl
- alpha
- 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 - Lifetime
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- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- BGHVSZXZNPMDJV-UHFFFAOYSA-N 2-(5-ethylpyridin-2-yl)ethanamine Chemical compound CCC1=CC=C(CCN)N=C1 BGHVSZXZNPMDJV-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000272534 Struthio camelus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Definitions
- p and said substituted phenyl is selected from consisting of lower alkoxylphenyl and 3,4,5-t-rimethoxy.
- This invention is concerned with pyridylethylated d-u-methylphenethylamines and derivatives thereof which are effective agents in modifying central nervous system activity.
- the invention is concerned with pyridylethylated d-wmethylphenethylamines of the structure shown vinylpyridine being derived from the group consisting of 2- and 4-vinylpyridine and the ring alkylated derivatives of 2- and 4-vinylpyridines.
- the most eflicient procedure has proven to be the acetic acid catalyzed condensation as described by Reich and Levine, J. Am. Chem. Soc., 77: 5434 (1955).
- the amines are secondary amines and can be readily converted to their monoand dihydrochlorides and similar acid salts.
- the secondary amine is readily acylated or aroylated upon treatment with acid chlorides of the type RCOCI wherein R has the significance described above.
- acylated and aroylated derivatives upon treatment with mineral acids give the corresponding acid salts and upon treatment with lower alkyl halides or sulfates afford the corresponding quaternary ammonium salts.
- R is lower alkyl, phenyl and substituted phenyl the group and 4-pyridyl e compounds of this invention on testing show diverse yet unambiguous response in their effect on the central nervous system in that they either promote central nervous system activity or significantly depress such activity.
- pyridylethylated d-a-methylphenethylamines of this invention are conveniently prepared by condensation of d-a-methylphenethylamine with a vinylpyridine, said by Weller and Strauss, Oxford, England.
- Example I N-d-a-methylphenethyl 2-(5 ethyl 2 pyridyl)ethylamine (Compound 9).
- a mixture of one-third mole each of d-a-methylphenethylamine, Z-Vinyl 5 ethylpyridine, and acetic acid in ml. of methanol was heated under reflux for 8 hours and distilled. After removal of low boiling fractions, a forerun was collected at l28-l40 (0.3 mm), and the product (41.5 g.) was obtained, B.P. 148-l50 (0.4 mm.). The forerun, upon trituration with hexane, gave 2.4 g. (4.1% M.P. l26127, not depressing the melting point of authentic d-a-methylphenethylacetamide.
- Example I Acetamide of Compound 1 (Compound 2) .A mixture of 9.6 g. (0.04 mole) of Compound 1 and 10 ml. of acetic anhydride was heated under reflux for 1 hour. When cool, after addition of ml. of water, and basification, the formed oil was extracted with 100 ml. of benzene and the product was obtained by distillation, 9.77 g. (87%), B.P. 179 (0.16 mm).
- Example 111 3,4,5-trimethoxybenzamide of Compound 1 (Compound 6) .-A solution of 9.6 g. (0.04 mole) of compound 1 in 35 ml. of benzene was added dropwise under stirring over 1 hour to a solution of 4.6 g. (0.02 mole) of 3,4,5- trimethoxybenzoyl chloride in 65 ml. of benzene while maintaining the temperature at 25-30". When addition was complete, the reaction mixture was heated under reflux for 1 hour and then stored at 20 for 24 hours. After extraction with dilute hydrochloric acid, and basification, 8.6 g. (98%) of product was separated and recrystallized.
Description
p and said substituted phenyl is selected from consisting of lower alkoxylphenyl and 3,4,5-t-rimethoxy.
3,055,906 Patented Sept. 25, 1962 This invention is concerned with pyridylethylated d-u-methylphenethylamines and derivatives thereof which are effective agents in modifying central nervous system activity. 'In particular, the invention is concerned with pyridylethylated d-wmethylphenethylamines of the structure shown vinylpyridine being derived from the group consisting of 2- and 4-vinylpyridine and the ring alkylated derivatives of 2- and 4-vinylpyridines. The most eflicient procedure has proven to be the acetic acid catalyzed condensation as described by Reich and Levine, J. Am. Chem. Soc., 77: 5434 (1955).
After a suitable reaction period under reflux, the products are collected by fractional distillation. The amines are secondary amines and can be readily converted to their monoand dihydrochlorides and similar acid salts.
In turn, the secondary amine is readily acylated or aroylated upon treatment with acid chlorides of the type RCOCI wherein R has the significance described above.
The acylated and aroylated derivatives upon treatment with mineral acids give the corresponding acid salts and upon treatment with lower alkyl halides or sulfates afford the corresponding quaternary ammonium salts.
Typical compounds representing the structural ambit of this invention are described in the table below:
TABLE Analyses Yield, N o. R M.P. n or per- Formula Carbon, per- Hydrogen, per- Nitrogen, per- B.P., 0 cent cent cent cent Calcd. Found Calcd Found Calcd. Found 120 (0.05) E 66 C1eH2oN'2 80. 0 80. 1 8. 4 8. 2 11.7 12.0 170-179 (0.16) 87 ClsH22N.0 9. 9 10. 1 151-152 85 CreHzsINzO--. 53. 8 54. 0 5. 9 6. 0 6. 6 6. 8 p-OH3OCeH C O 238-242 (0.03)-- 39 Cz4H2uN202 77.0 77.0 7 0 6. 7 7. 5 7.0 o-C2H OOaH4CO.. 226-229 (0.03).- 47 OH28N202--- 7. 2 6. 8 Il\ IB 117-118 58 CzcHaoNzO-i. 71. 9 71.7 7.0 7. 2 6. 5 6.0 128-134 (0.08) E 53 CrsHzuNz 80.0 79. 5 8. 4 8. 4 11. 7 11. 7 103-106 Ob 57 Cz5HzaN2Oz 77.3 77.4 7. 3 7.1 7.2 6.9 148-150 (0.4) E 01s 24N2 80. 6 80. 7 9. 0 9. 1 l0. 4 9. 8
B Py=2-pyridyl unless otherwise indicated; b Melting points are not corrected and were 1w Py=4-pyridyl; Py=6-ethyl-2-pyridyl. established on a Fisher-Johns melting point block.
Recrystallizing solvent; M ethyl acetate; vb hexane-benzene. d Yields are expressed as recrystallized or distilled product.
8 Analyses are 1 Compound is s [111 in methanol; compound 11 TMB=3,4,5-tri.methoxybenzo methiodide of compound 2.
l @om-on-g-nm-om-m wherein R is lower alkyl, phenyl and substituted phenyl the group and 4-pyridyl e compounds of this invention on testing show diverse yet unambiguous response in their effect on the central nervous system in that they either promote central nervous system activity or significantly depress such activity.
While the exact mechanism of the pharmacological response to the compounds of this invention is as yet unknown, it would appear that they act and mediate central nervous system responses which, depending on the structure of the compound involved, are observable as a depressant or analeptic pharmacological response.
The pyridylethylated d-a-methylphenethylamines of this invention are conveniently prepared by condensation of d-a-methylphenethylamine with a vinylpyridine, said by Weller and Strauss, Oxford, England.
1, +21.40; compound 7, +2430; compound 9, +2230.
The invention will be further illustrated by description in connection with the following specific examples showing the preparation of compounds of the invention.
Example I N-d-a-methylphenethyl 2-(5 ethyl 2 pyridyl)ethylamine (Compound 9). A mixture of one-third mole each of d-a-methylphenethylamine, Z-Vinyl 5 ethylpyridine, and acetic acid in ml. of methanol was heated under reflux for 8 hours and distilled. After removal of low boiling fractions, a forerun was collected at l28-l40 (0.3 mm), and the product (41.5 g.) was obtained, B.P. 148-l50 (0.4 mm.). The forerun, upon trituration with hexane, gave 2.4 g. (4.1% M.P. l26127, not depressing the melting point of authentic d-a-methylphenethylacetamide.
Compounds 1 and 7 were similarly prepared.
Example I] Acetamide of Compound 1 (Compound 2) .A mixture of 9.6 g. (0.04 mole) of Compound 1 and 10 ml. of acetic anhydride was heated under reflux for 1 hour. When cool, after addition of ml. of water, and basification, the formed oil was extracted with 100 ml. of benzene and the product was obtained by distillation, 9.77 g. (87%), B.P. 179 (0.16 mm).
A solution of 2.8 g. (0.01 mole) of the compound in 25 ml. of acetonitrile and 2 ml. of methyl iodide was refluxed for 2 hours, and upon cooling, yielded 3.6 g. (85%) of the methiodide (Compound 3). Attempted hydrogenation with rhodium on carbon afforded only unconverted reactant.
Example 111 3,4,5-trimethoxybenzamide of Compound 1 (Compound 6) .-A solution of 9.6 g. (0.04 mole) of compound 1 in 35 ml. of benzene was added dropwise under stirring over 1 hour to a solution of 4.6 g. (0.02 mole) of 3,4,5- trimethoxybenzoyl chloride in 65 ml. of benzene while maintaining the temperature at 25-30". When addition was complete, the reaction mixture was heated under reflux for 1 hour and then stored at 20 for 24 hours. After extraction with dilute hydrochloric acid, and basification, 8.6 g. (98%) of product was separated and recrystallized.
It is to be noted that it is intended to cover all changes and modifications of the examples of the invention herein chosen for the purpose of illustration which do not constitute departures from the spirit and scope of the invention.
We claim:
1. The amide of the structure wherein Py is selected from the group consisting of 2- .pyridyl, 4-pyridyl, and 2-pyridyl-5-ethyl and R is selected from the group consisting of lower alkyl, phenyl, lower alkoxyphenyl, and 3,4,5-trimethoxyphenyl.
2. The compound of the formula 4. The compound of the formula N @om-thn-nuom-cmonto -00H3 I OCH! References Cited in the file of this patent UNITED STATES PATENTS 2,792,403 Blicke May 14, 1957 2,843,594 Leditschke et al. July 15, 1958 2,870,156 Perron et al. Jan. 20, 1959 OTHER REFERENCES Noller: The Chemistry of Organic Compounds, 2nd
Ed., page 244 (Saunders) (1957).
Claims (1)
1. THE AMIDE OF THE STRUCTURE
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63462A US3055906A (en) | 1960-10-19 | 1960-10-19 | Pyridylethylated d-alpha-methylphenethylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63462A US3055906A (en) | 1960-10-19 | 1960-10-19 | Pyridylethylated d-alpha-methylphenethylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3055906A true US3055906A (en) | 1962-09-25 |
Family
ID=22049365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US63462A Expired - Lifetime US3055906A (en) | 1960-10-19 | 1960-10-19 | Pyridylethylated d-alpha-methylphenethylamines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3055906A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133077A (en) * | 1964-05-12 | Z-pysudyl-alkylamines and their lower | ||
| US4358446A (en) * | 1979-07-19 | 1982-11-09 | Shell Oil Company | Use as fungicides of N-(3-pyridylmethyl)-N-acyl anilines |
| US4501746A (en) * | 1981-12-18 | 1985-02-26 | Eli Lilly And Company | N,N-disubstituted carboxamide derivatives, and fungicidal use thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792403A (en) * | 1955-01-05 | 1957-05-14 | Univ Michigan | 2-pyridylethyl-phenylethylalkylamines |
| US2843594A (en) * | 1958-07-15 | Substituted isonicotinic acid amides | ||
| US2870156A (en) * | 1958-03-03 | 1959-01-20 | Bristol Lab Inc | N-pyridylethyl-3, 4, 5 trimethoxybenzamide |
-
1960
- 1960-10-19 US US63462A patent/US3055906A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843594A (en) * | 1958-07-15 | Substituted isonicotinic acid amides | ||
| US2792403A (en) * | 1955-01-05 | 1957-05-14 | Univ Michigan | 2-pyridylethyl-phenylethylalkylamines |
| US2870156A (en) * | 1958-03-03 | 1959-01-20 | Bristol Lab Inc | N-pyridylethyl-3, 4, 5 trimethoxybenzamide |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133077A (en) * | 1964-05-12 | Z-pysudyl-alkylamines and their lower | ||
| US4358446A (en) * | 1979-07-19 | 1982-11-09 | Shell Oil Company | Use as fungicides of N-(3-pyridylmethyl)-N-acyl anilines |
| US4501746A (en) * | 1981-12-18 | 1985-02-26 | Eli Lilly And Company | N,N-disubstituted carboxamide derivatives, and fungicidal use thereof |
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