USRE22264E - Secondary and tertiary j-amino - Google Patents
Secondary and tertiary j-amino Download PDFInfo
- Publication number
- USRE22264E USRE22264E US22264DE USRE22264E US RE22264 E USRE22264 E US RE22264E US 22264D E US22264D E US 22264DE US RE22264 E USRE22264 E US RE22264E
- Authority
- US
- United States
- Prior art keywords
- amino
- compound
- tertiary
- alkyl
- group
- 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
- 150000001875 compounds Chemical class 0.000 description 7
- PTWPWUVEQZXOFJ-UHFFFAOYSA-N 7-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2 PTWPWUVEQZXOFJ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- -1 alkyl radicals Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- HWIZGBVJDMPJRO-UHFFFAOYSA-N 6-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C2COC(=O)C2=C1 HWIZGBVJDMPJRO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ONGYYRQSCJYQHL-UHFFFAOYSA-N 2-(benzylamino)acetaldehyde Chemical compound O=CCNCC1=CC=CC=C1 ONGYYRQSCJYQHL-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
Definitions
- R may be hydrogen, alkyl or aryl radical, R may be aryl or alkyl with more than one carbon atom, and any two or three R" H, the remaining R"
- a convenient method Mitchells reagent Mitchells reagent.
- R is taken from the group consisting of H, alkyl and aryl radicals contain ing not more than 6 carbon atoms
- R. is taken from the group consisting of aryl and alkyl radicals having at least two carbon atoms, and not more than 6 and at least two and no more than three R" are OH, the remaining being H. said substance being prepared as a therapeutic agent.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Reissued Feb. 9, 1943 UNITED STATES PATENT OFFICE SECONDARY AND TERTIARY S-AMINO- BIETHYL-POLYHYDROXY-PHTHALIDES Walter Siegfried Loewe, New
Neumann, Scarsdale, N. Y.
signor to Walter Rochelle, N. Y., as-
No Drawing. Original No. 2,268,990, dated January 6, 1942, Serial No. 291,30 Application for reissue June 4, August 22, 1939. 8, 1942, Serial No.
4 Claims. (Cl. 260-344) 3 amino methyl polyhydroxy organic bases.
I have discovered that the primary and the mono-methyl amines of this class of chemicals tious diseases, and the like.
My novel compounds can be expressed by the general formula:
where R may be hydrogen, alkyl or aryl radical, R may be aryl or alkyl with more than one carbon atom, and any two or three R" H, the remaining R" A convenient method Mitchells reagent.
Example II.Method of preparing 3-(benzylaminomethyl) -5,7-hydroxy-phthalide.
17 gm. of 2,4-hydroxybenzoic acid, 15 gm. 01' benzylaminoacetaldehyde, 300 cc. of glacial acetic concentrated hydrochloric acid and 30 cc. of water are heated together for about fifteen hours at C. The mixture is evaporated, the residue dissolved in water, filtered, and the base precipitated from the filtrate by amwhen added to the solution of the base in a dilute hydrochloric acid, produces a reddish-brown precipitate.
Example IIL-Method for preparing 3-(di-nbutyl) -aminomethyl-4,5,B-hydroxy-phthalide.
11.5 gm. of gallic acid, 12 gm. of di-n-butyl- 300 cc. of glacial acetic acid, 93 cc.
brownish powder.
The foregoing description of ployed is merely illustrative of the invention.
polyhydroxy-phthalides, as, for example, substitution of monoor di-alkyl or -aryl-amine in place of the halogen in halogenmethyl-polyhydroxy-phthalides, without departing from the spirit of my invention as set forth in the appended claims.
I claim as my 1. A substance represented by the formula:
invention and salts thereof where R is taken from the group consisting of H, alkyl and aryl radicals contain ing not more than 6 carbon atoms, R. is taken from the group consisting of aryl and alkyl radicals having at least two carbon atoms, and not more than 6 and at least two and no more than three R" are OH, the remaining being H. said substance being prepared as a therapeutic agent.
2. A compound of the group consisting in 3- (n-propyl-aminomethyl) -4,5 ,6 hydroxy-phthalide and salts thereof, said compound being preared as a therapeutic agent.
3. A compound of the group consisting in 3- (benzylaminomethyl) 5,7 hydroxy phthalide and salts thereof, said compound being prepared as a therapeutic agent.
'4. A compound of the group consisting in 3- (di n butyl') aminomethyl 4,5,6 hydroxyphthal-ide and salts thereof, said compound being therapeutic agent.
WALTER SIEGFRIED LOEWE.
prepared as a
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE22264E true USRE22264E (en) | 1943-02-09 |
Family
ID=2088678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US22264D Expired USRE22264E (en) | Secondary and tertiary j-amino |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE22264E (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473484A (en) * | 1946-09-12 | 1949-06-14 | Smith Kline French Lab | Method for the preparation of aminophthalidylalkanes |
| US2513698A (en) * | 1945-03-09 | 1950-07-04 | Abbott Lab | 2 (3) benxofuranone derivatives and methods of making them |
| US2581986A (en) * | 1946-02-02 | 1952-01-08 | Smith Kline French Lab | Method for the preparation of aminophthalidylalkane salts |
-
0
- US US22264D patent/USRE22264E/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513698A (en) * | 1945-03-09 | 1950-07-04 | Abbott Lab | 2 (3) benxofuranone derivatives and methods of making them |
| US2581986A (en) * | 1946-02-02 | 1952-01-08 | Smith Kline French Lab | Method for the preparation of aminophthalidylalkane salts |
| US2473484A (en) * | 1946-09-12 | 1949-06-14 | Smith Kline French Lab | Method for the preparation of aminophthalidylalkanes |
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