US2417726A - Teteahybro- - Google Patents
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- US2417726A US2417726A US2417726DA US2417726A US 2417726 A US2417726 A US 2417726A US 2417726D A US2417726D A US 2417726DA US 2417726 A US2417726 A US 2417726A
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- Prior art keywords
- methoxy
- amino
- omega
- tetrahydro
- quinoline
- Prior art date
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- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- 150000003248 quinolines Chemical class 0.000 description 5
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- -1 methylbutylidene Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000002196 fr. b Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- VDMXPMYSWFDBJB-UHFFFAOYSA-N 1-ethoxypentane Chemical compound CCCCCOCC VDMXPMYSWFDBJB-UHFFFAOYSA-N 0.000 description 1
- 208000010362 Protozoan Infections Diseases 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
Definitions
- Examples are 1:2:324 tetrahydro-G-methoxy-S-(omega dial kylamino-propylamino) -quino1ines, 1 :2 :3 :4-tetrahydro-6-methoxy-8-(omega dialkylamino-butylamino) -quinolines and 1 :2 :3 :4-tetrahydro-6- methoxy-8-(omega-dialkylamino isopentylami no)-quinolines, specifically the B-(omega-diethylamino-propylamino), the 8-(omega-diethylamino-butylamino), and the 8-(omega-diethy1amino-isopentylamino) compounds.
- the invention further includes preparation of these new compounds by alkaline or neutral reduction of the anils obtained by condensation of 6-alkoxy-8-amino-quinoline with a ketal of an omega-dialkylamino-a1kanone, for instance a suitable ketal of omega-diethylamino-pentanone- 2.
- This reduction can be effected satisfactorily by use of metallic sodium in essentially anhydrous alcoholic solution.
- metallic sodium in ethyl or amyl alcohol can be employed.
- Anhydrous conditions are necessary because the anils are sensitive to hydrolysis.
- Another process within the purview of the present invention for preparing these novel compounds comprises the reaction of 1:2:3z4-tetrahydro-6-alkoxy-S-amino-quinolines in the presence of ammonium chloride or other slightly acidic salt with a compound having one of the following formulae:
- R and R4 are lower alkyl groups or hydrogen atoms
- R1, R2 and R3 are lower alkyl groups
- n is an integer more than 2 and less than 10, followed by reduction of the reaction products thus obtained.
- Catalytic hydrogenation or reduction with sodium in alcohol for example, ethyl or amyl alcohol
- Example I About 174 gm. of S-methoxy-B-amino-quinoline are reduced catalytically in the presence of 20% Raney nickel at 120 C. and 35 atmospheres pressureusing 200 cc. dioxane as solvent.
- Example II 200 gm. of fi-methoxy-S-aminoquinoline is reduced catalytically in the presence of 18% Raney nickel at C. and 40 atmospheres pressure using 200 c. c. dioxane as solvent.
- the product, 6-methoxy-8-amino- 1 t 2 3 z l-tetrahydro quinoline (B. P. l35/0.05 mm., 95% yield) is stored in an atmosphere of hydrogen.
- a mixture of 84.5 gm. of 1:2:3z-tetrahydro-6- methoxy-S-aminoquino-line, gm. of 5diethylamino-2:Z-diethoxypentane and 1.5 gm. of ammonium chloride are heated at -170 C. for 1 hour and then at ITO- C. for hour with vigorous stirring, in an atmosphere of hydrogen. Practically the theoretical quantity of alcohol is evolved.
- the reaction product mainly G-methoxy- B-N-(Qmega diethylamino-a-methyl butylidene) amino l:2:3:4-tetrahydroquinoline is poured quickly into 3 litres of absolutely anhydrous amyl alcohol at 80 0., to which 40 gm. of sodium has just previously been added. IA further 120 gm. of sodium is then added and the alcohol refluxed until all the sodium has dissolved. An atmosphere of hydrogen is maintained over the reaction mixture during the following operations. The reaction mixture is made acid to Congo red with concentrated hydrochloric acid and the amyl alcohol removed by steam distillation. The liquors remaining are basified with 50% caustic soda and ether extracted] On removal of the ether the product is carefully fractionated.
- Example III 36 gm. of G-methoxy-S-N-(omega diethylamino-a-methyl butyD-amino quinoline is refiuxed with 1.3 litres of anhydrous amyl alcohol and 100 gm. of sodium until all the sodium has dissolved.
- the reaction scheme may be indicated thus:
- R1, R2 and R3 are of the class consisting of lower alkyl groups and :c is an integer less than 10.
- R and R4 are of the class consisting of lower alkyl and hydrogen, R1, R2, and R3 are lower alkyl, and n is an integer more than 2 but less than 10; and reducing the reaction product to obtain a 1:2:3: i-tetrahydro-G-alkoxy- 8- (omega-dialky1amino-alkylamino) -quinoline.
- the process that comprises the following steps: catalytically reducing S-methoxy-B-aminoquinoline to produce 122:3:4-tetrahydro-6- methoXy-B-amino quinoiine, reacting the reduction product with omega-diethy1amino-p-,B-di ethoxy-pentane to produce 1:2:324-tetrahydro-6- methoxy 8 (a methyl omega diethylaminobutylideneamino)-quinoline, and reducing the reaction product to obtain 1:2:314-tetrahydro-6- methoxy-8-u-methyl-omega-diethylamino-butylamino) -quinoline.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
patented or. 18 1947 UNITED STATES PATENT OFFICE 1;2,3,4 TETBAHYDRO6-ALKOXY-8* (OMEGA- DIALKYL-AMINO-ALKYL-AMINO) QUINO- LINES AND METHOD FOR THEIR PREP- ARATION Harry James Barber, Gidea Park, and William Robert Wragg, Cockfosters, England, assignors to May & Baker Limited, Dagenham, England,
a British company No Drawing. Application March 14, 1944, Serial No. 526,474. In Great Britain March 1, 1943 Formula I HNCH(CHz)aN Formula 2 EN C H2) 3N CzHg Formula 3 CzHs Formula 4 A disadvantage of these compounds when used as antimalarial agents is that they exhibit substan- 11 Claims. (Cl. 260288) 2 tial toxicity toward the human organism, a factor of great importance in view of the long periods of treatment and relatively large dosages necessary to control the protozoan infection.
It is now found, pursuant to the present invention, that a class of related compounds possesses antimalarial activity comparable to the quinoline derivatives above mentioned but the compounds, unexpectedly, have materially reduced toxicity. These new compounds are 122:3:4-tetrahydro-G-alkoxy-S- (omega-dialkylamino-alkyl amino) -quinolines which can be represented by the general formula wherein R1, R2, and R3 are lower alkyl groups and a: is an integer less than 10. Examples are 1:2:324 tetrahydro-G-methoxy-S-(omega dial kylamino-propylamino) -quino1ines, 1 :2 :3 :4-tetrahydro-6-methoxy-8-(omega dialkylamino-butylamino) -quinolines and 1 :2 :3 :4-tetrahydro-6- methoxy-8-(omega-dialkylamino isopentylami no)-quinolines, specifically the B-(omega-diethylamino-propylamino), the 8-(omega-diethylamino-butylamino), and the 8-(omega-diethy1amino-isopentylamino) compounds.
These now compounds can be prepared in accordance with the present invention by reduction of the corresponding quinoline derivatives using catalytic hydrogenation, preferably with Raney nickel, or by chemical or electro-chemical methods of reduction which are conventional for the quinoline series.
It is also contemplated within the present invention to prepare these novel compounds by methods heretofore employed in manufacture of the corresponding quinoline compounds, with substitution of a tetrahydroquinoline intermediate for the corresponding quinoline intermediate.
The invention further includes preparation of these new compounds by alkaline or neutral reduction of the anils obtained by condensation of 6-alkoxy-8-amino-quinoline with a ketal of an omega-dialkylamino-a1kanone, for instance a suitable ketal of omega-diethylamino-pentanone- 2. This reduction can be effected satisfactorily by use of metallic sodium in essentially anhydrous alcoholic solution. Thus, for example, sodium in ethyl or amyl alcohol can be employed. Anhydrous conditions are necessary because the anils are sensitive to hydrolysis.
Another process within the purview of the present invention for preparing these novel compounds comprises the reaction of 1:2:3z4-tetrahydro-6-alkoxy-S-amino-quinolines in the presence of ammonium chloride or other slightly acidic salt with a compound having one of the following formulae:
wherein R and R4 are lower alkyl groups or hydrogen atoms, R1, R2 and R3 are lower alkyl groups, and n is an integer more than 2 and less than 10, followed by reduction of the reaction products thus obtained. Catalytic hydrogenation or reduction with sodium in alcohol (for example, ethyl or amyl alcohol) are satisfactory methods for this purpose.
It should be understood that the designations (CHzM and (CHz)n-1 used in this specification and in the appended claims include not only straight chain but also branched chain alkyl groups.
The following examples illustrate methods of carrying out the present invention, but it is to be understood that these examples are given by way of illustration and not of limitation;
Example I About 174 gm. of S-methoxy-B-amino-quinoline are reduced catalytically in the presence of 20% Raney nickel at 120 C. and 35 atmospheres pressureusing 200 cc. dioxane as solvent. The product, 6-methoxy-8-amino 1:2:3z4 tetrahydroquinoline, is distilled (B. P. 19D/3 mm.) and stored in an atmosphere of hydrogen.
About 17.8 gm. of fi-methoxy-S-amino-l:2z3z4- tetra-hydroquinoline thus prepared, 25.0 gm. of omega-diethylamino-p,e-di-ethoxy-pentane and approximately 0.2 gm. of ammonium chloride (as catalyst) are heated at a uniform rate from 135 C. to 195 C. over 2 hours with stirring. Practically the theoretical quantity of alcohol is evolved. The product is vacuum distilled, the fraction B. P. 184/.1 mm. which consists of 6- methoxy-B-N(-omega-diethylamino o: methylbutylidene) -amino-1 2 3 l-tetra-hydroquinoline, is stored in an atmosphere of hydrogen.
About 10 gm. of G-methoxy-fl-N (omega-diethylamino a methyl-butylidene) amino-1:2:3z4- tetrahydroquinoline obtained in this manner are thee s elvs n 9. 9- Q anhyd us et l we:
4 hol in an atmosphere of hydrogen. Approximately 4.5 gm. of sodium are added in small pieces over 1 hour, the reaction being completed by heating on a steam bath under reflux. The prodnot is made acid with concentrated hydrochloric acid, warmed to decompose unreduced anil, filtered to remove salt and the alcohol distilled from the filtrate under reduced pressure. The filtrate is then made basic and extracted with ether.
After evaporation of the other the product is distilled in an atmosphere of hydrogen and a fraction B. P, 175180/.1 mm. 6-methoxy-8-N (omega-diethylamino-a-methyl-butyl) amino- 1:2:3: l-tetrahydroquinoline, is collected. The product is stored in an atmosphere of hydrogen.
Example II 200 gm. of fi-methoxy-S-aminoquinoline is reduced catalytically in the presence of 18% Raney nickel at C. and 40 atmospheres pressure using 200 c. c. dioxane as solvent. The product, 6-methoxy-8-amino- 1 t 2 3 z l-tetrahydro quinoline (B. P. l35/0.05 mm., 95% yield) is stored in an atmosphere of hydrogen.
A mixture of 84.5 gm. of 1:2:3z-tetrahydro-6- methoxy-S-aminoquino-line, gm. of 5diethylamino-2:Z-diethoxypentane and 1.5 gm. of ammonium chloride are heated at -170 C. for 1 hour and then at ITO- C. for hour with vigorous stirring, in an atmosphere of hydrogen. Practically the theoretical quantity of alcohol is evolved. The reaction product, mainly G-methoxy- B-N-(Qmega diethylamino-a-methyl butylidene) amino l:2:3:4-tetrahydroquinoline is poured quickly into 3 litres of absolutely anhydrous amyl alcohol at 80 0., to which 40 gm. of sodium has just previously been added. IA further 120 gm. of sodium is then added and the alcohol refluxed until all the sodium has dissolved. An atmosphere of hydrogen is maintained over the reaction mixture during the following operations. The reaction mixture is made acid to Congo red with concentrated hydrochloric acid and the amyl alcohol removed by steam distillation. The liquors remaining are basified with 50% caustic soda and ether extracted] On removal of the ether the product is carefully fractionated. The fraction, B. P. l'75-l80/0.05 mm., B-methOXy-B-N-(Omega diethylamino-a-methyl butyl) amino-1: 2 :3 4- tetrahydro quinoline, in 74% yield, is stored in an atmosphere of hydrogen.
Example III 36 gm. of G-methoxy-S-N-(omega diethylamino-a-methyl butyD-amino quinoline is refiuxed with 1.3 litres of anhydrous amyl alcohol and 100 gm. of sodium until all the sodium has dissolved. The reaction scheme may be indicated thus:
An atmosphere of hydrogen is maintained over the reaction mixture during the following operations. The reaction is made acid to Congo red with concentrated hydrochloric acid and theamyl eehel r t eve by te m dist l tion, The
present invention without departing from the spirit and scope thereof and the invention is to be limited only by the appended claims.
What is claimed is:
1. A composition of matter represented by the formula:
wherein R1, R2 and R3 are of the class consisting of lower alkyl groups and :c is an integer less than 10.
2. A 1 :2 3 4-tetrahydro-6-a1koxy-8- (omegadialkyl-amino-alky1amino) -quinoline,
3. A 1 2 :3 4-tetrahydro-6-methoXy-8- (omegadialkyl-amino-propylamino) -quin0line.
4. A 1:2: :e-tetrahydro-fi-methoxy-8-(omegadialkyl-amino-butylamino) -quino1ine.
5. A 1 2 3 :4-tetrahydro-6-methoxy-8- (omegadialkyl-amino-isopentylamino) -quinoline.
6. 1:213:4-tetrahydro 6 methoxy-8-(omegadiethyl-amino-propylamino) -quino1ine.
7. 112:3:4-tetrahydro 6 methoXy-8-(omegadiethyl-amino-butylamino) -quino1ine.
8. 1 :2 23:4 tetrahydro-G-methoxy-S-(or-methyl omega-diethy1-amino-butylamino) -quinoline.
9. The process that comprises the step of reacting a 6-alkoxy-8-amino-quinoline with a substance selected from the class consisting of compounds of the formulae:
wherein R and R4 are of the class consisting of lower alkyl and hydrogen, R1, R2, and R3 are lower alkyl, and n is an integer more than 2 but less than 10; and reducing the reaction product to obtain a 1:2:3: i-tetrahydro-G-alkoxy- 8- (omega-dialky1amino-alkylamino) -quinoline.
10. The process that comprises condensing a G-alkoxy-S-amino-quinoline with a ketal of an omega-dialkylamino-alkanone to form an anil intermediate, and reducing this anil intermediate under anhydrous conditions to produce the corresponding 1 :2 3 i-tetrahydro-G-alkoxy-B- (omega-dialkylamino-alkylamino) -quinoline.
11. The process that comprises the following steps: catalytically reducing S-methoxy-B-aminoquinoline to produce 122:3:4-tetrahydro-6- methoXy-B-amino quinoiine, reacting the reduction product with omega-diethy1amino-p-,B-di ethoxy-pentane to produce 1:2:324-tetrahydro-6- methoxy 8 (a methyl omega diethylaminobutylideneamino)-quinoline, and reducing the reaction product to obtain 1:2:314-tetrahydro-6- methoxy-8-u-methyl-omega-diethylamino-butylamino) -quinoline.
HARRY JAMES BARBER. WILLIAM ROBERT WRAGG.
REFERENCES CITED The following references are of record in the file of thispatent:
UNITED STATES PATENTS Journal of The Indian Chemical Society, vol. 14, pages 468-473 (1937) Number
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2417726A true US2417726A (en) | 1947-03-18 |
Family
ID=3435431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2417726D Expired - Lifetime US2417726A (en) | Teteahybro- |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2417726A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1872826A (en) * | 1927-08-16 | 1932-08-23 | Winthrop Chem Co Inc | Soluble salts of organic bases and the process of preparing the same |
-
0
- US US2417726D patent/US2417726A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1872826A (en) * | 1927-08-16 | 1932-08-23 | Winthrop Chem Co Inc | Soluble salts of organic bases and the process of preparing the same |
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