US1873732A - Bactericide applicable to acid-fast bacteria - Google Patents
Bactericide applicable to acid-fast bacteria Download PDFInfo
- Publication number
- US1873732A US1873732A US329077A US32907728A US1873732A US 1873732 A US1873732 A US 1873732A US 329077 A US329077 A US 329077A US 32907728 A US32907728 A US 32907728A US 1873732 A US1873732 A US 1873732A
- Authority
- US
- United States
- Prior art keywords
- acid
- applicable
- bactericide
- fast bacteria
- carbon atoms
- 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
Links
- 230000000844 anti-bacterial effect Effects 0.000 title description 9
- 241000894006 Bacteria Species 0.000 title description 6
- 239000003899 bactericide agent Substances 0.000 title description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000000126 substance Substances 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000000022 bacteriostatic agent Substances 0.000 description 5
- -1 alkaline earth metal salts Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 3
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- XMVQWNRDPAAMJB-UHFFFAOYSA-N (+)-13-Cyclopent-2-enyl-tridecansaeure Natural products OC(=O)CCCCCCCCCCCCC1CCC=C1 XMVQWNRDPAAMJB-UHFFFAOYSA-N 0.000 description 2
- XMVQWNRDPAAMJB-QGZVFWFLSA-N (S)-chaulmoogric acid Chemical compound OC(=O)CCCCCCCCCCCC[C@H]1CCC=C1 XMVQWNRDPAAMJB-QGZVFWFLSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 241000558306 Gynocardia odorata Species 0.000 description 1
- 241001179022 Hydnocarpus anthelminthicus Species 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XRCJOMAARACHTL-UHFFFAOYSA-N ethyl 2-heptylnonanoate Chemical compound CCCCCCCC(C(=O)OCC)CCCCCCC XRCJOMAARACHTL-UHFFFAOYSA-N 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
Definitions
- ROGER ADAMS OF URBANA, ILLINOIS, ASSIGNOR TO ABBOTT LABORATORIES, OF NORTH CHICAGO, ILLINOIS, A CORPORATION OF ILLINOIS BACTERICIDE APPLICABLE TO ACID-FAST BACTERIA No Drawing.
- This invention relates to the preparation of aliphatic acids and derivatives of these acids.
- These compounds have the general formula HOOOZ, R/ where R and R represent aliphatic-hydrocarbon radicals such as alkyl or alkylene, and m where Z represents a hydrogen atom, an alkali or alkaline earth metal or a hydrocarbon radical.
- Chaulmoogra oil, chaulmoogric acid, and homologues of chaulmoogric acid and their derivatives have long been known to be effective in combating certain diseases such as leprosy, produced by acid-fast bacteria.
- Such chaulmoogra derivatives contain an unsaturated five membered carbon ring to which the activity against the leper bacilli was formerly attributed. Recent discoveries have shown that a variety of other acids which contain other types of carbon rin are also effective against such acid-fast bac- 95 teria.
- esters may be prepared by introducing the hydrocarbon radicals successively into an ester with an active methylene group, which then on treatment with alkalies, can yield a substituted acetic acid.
- esters are malonic ester and acetoacetgic ester.
- the reactions involved are as follows, where R and R are aliphatic alkyl radicals, such as alkyl or alkylene ooocim coocun 00002115 RCH/ cooo m 00001115 ROB +NaBr+CzHH.
- the substance is administered in an equal mixture of olive oil, preferably with two per cent anesthesin, added to reduce the pain of injection, although the anesthesin is not required. That is to say, one part of the compound is mixed with an equal part of olive oil, and to this is added a quantity of anesthesin equal to two per cent of the total weight. About five to six cc. of the mixture is injected intramuscularly once a week. However, the administration can be varied substantially, both as to amount and the frequency. The quantities and method of administration of the other materials mentioned above will be similar.
- R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylene
- Z represents a hydrogen atom, an alkali or alkaline earth metal or a hydrocarbon radical
- R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylen-e, and where Z represents a hydrogen atom, an alkyli or alkaline earth metal or a hydrocarbon radical.
- R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylene, and where Z represents a hydrogen atom, an alkali or alkyline earth metal or a hydrocarbon radical, and Where the carboxyl group is attached near the middle of the chain.
- a new bactericidal or bacteriostatic agent especially applicable to acid-fast bacteria a substance which is a member of the group consisting of aliphatic acids, alkali and alkaline earth metal salts thereof and hydrocarbon esters thereof, in which the carboxyl group is located at a point removed from the end of the chain, said substance containing from 10 to 21 carbon atoms.
- composition as defined in claim 4 and containing from 15 to 18 carbon atoms.
- a new bactericidal or bacteriostatic agent especially applicable to acid-fast bacteria a substance which is a member of the group consisting of aliphatic acids, alkali and alkaline earth metal salts thereof, and
- hydrocarbon esters thereof in which the carboxyl group is attached to a carbon atom at approximately the center of the chain, said substance containing from 10 to 21 carbon atoms.
- ROGER ADAMS containing from 15 to 1 8 carbon atoms.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented-Aug. 23,; 1932- UNITED STATES PATENT m m:
ROGER ADAMS, OF URBANA, ILLINOIS, ASSIGNOR TO ABBOTT LABORATORIES, OF NORTH CHICAGO, ILLINOIS, A CORPORATION OF ILLINOIS BACTERICIDE APPLICABLE TO ACID-FAST BACTERIA No Drawing.
This invention relates to the preparation of aliphatic acids and derivatives of these acids. These compounds have the general formula HOOOZ, R/ where R and R represent aliphatic-hydrocarbon radicals such as alkyl or alkylene, and m where Z represents a hydrogen atom, an alkali or alkaline earth metal or a hydrocarbon radical. I v
Chaulmoogra oil, chaulmoogric acid, and homologues of chaulmoogric acid and their derivatives have long been known to be effective in combating certain diseases such as leprosy, produced by acid-fast bacteria.
Such chaulmoogra derivatives contain an unsaturated five membered carbon ring to which the activity against the leper bacilli was formerly attributed. Recent discoveries have shown that a variety of other acids which contain other types of carbon rin are also effective against such acid-fast bac- 95 teria.
My further discoveries seem to demonstrate that a ring structure is not necessary but that the number of carbon atoms, the molecular weight of the compounds, and the position of the carboxyl group in the chain, are the important factors in determining the bactericidal and bacteriostatic efiiciency of the products. (The term bacteriostatic means preventing growth of bacteria, as 8 distinguished from bactericidal which means bacteria destroying.) Compounds containing more than nine and less than twenty-two carbon atoms appear to be most efiicient, particularly those containing 15 to 18 carbon atoms. The presence or absence of a ring structure seems to be of minor importance.
The discovery of the bactericidal efiiciency of these acids described in this application is of particular importance since certain analogous compounds, which are very well known, such as stearic acid, show no appreciable germicidal efliciency whatsoever. In stearic acid, the carboxyl group is at the end of the chain of seventeen carbon atoms. I are prepared are given as illustrations of the 10f Application filed December 28, 1928. Serial No. 829,077.
have found that if the carboxyl group is removed from this position, and placed farther down towards the center of the chain, the efficiency is markedly increased. The highest efliciency seems to reside in such compounds in which the carboxyl group is attached to the middle carbon atom or to a .carbon atom that is near the middle.
These acids have the additional advantage that they may be prepared and made available for therapeutic use much more readily than is the case with the ring containing compounds previously studied.
These acids may be prepared by introducing the hydrocarbon radicals successively into an ester with an active methylene group, which then on treatment with alkalies, can yield a substituted acetic acid. Examples of such esters are malonic ester and acetoacetgic ester. Illustrating with malonic ester, the reactions involved are as follows, where R and R are aliphatic alkyl radicals, such as alkyl or alkylene ooocim coocun 00002115 RCH/ cooo m 00001115 ROB +NaBr+CzHH.
cooozm OOOCzHs ROB. +2NaOH- ROR ooooun ooom OOONa coon no R +2no1 ROR' +2Na01 COONa coon ROE coon heat R oooH The following examples of such acids and some of their intermediates from which they straight chains. Wherever two formulae are K invention. Unless otherwise indicated in the formula, the hydrocarbon radicals are given, the first mentioned formula refers to the intermediate diethyl dialkyl malonates.
Melting Boiling point point C4HBCH(COOH)C4HQ 153:]lfimm C4HoCH(COOCzH5) C4H 114-115 /15mm 1soC5HuCH(COOH)1so 158 15mm 146r149/2. 5mm 160162/2mm 187188/9mn1 196198/ 10mm 185186/9mm 148150/3mm 149-151/1mm 167l69/4mm 164-166/2mm 179-183/3mm 186138/1mm 175180/3mm 186-190/3mm 200204/3mm 205209/3mm As an example, ethyl di-n-heptyl acetate is representative of the group of compounds covered. by the application, which is being used clinically. The substance is administered in an equal mixture of olive oil, preferably with two per cent anesthesin, added to reduce the pain of injection, although the anesthesin is not required. That is to say, one part of the compound is mixed with an equal part of olive oil, and to this is added a quantity of anesthesin equal to two per cent of the total weight. About five to six cc. of the mixture is injected intramuscularly once a week. However, the administration can be varied substantially, both as to amount and the frequency. The quantities and method of administration of the other materials mentioned above will be similar.
The scope of the invention should be determined by reference to the appended claims, said claims being construed as broadly as possible consistent with the state of the art.
I claim as my invention:
1. As a new bactericidal or bacteriostatic agent, an aliphatic substance containing from 10 to 21 carbon atoms and having the general formula CHCOOZ, R!
where R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylene, and Where Z represents a hydrogen atom, an alkali or alkaline earth metal or a hydrocarbon radical.
2. As a new bactericidal or bacteriostatic agent, an aliphatic substance containing from 15 to 18 carbon atoms and having the general formula onoooz, RI
where R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylen-e, and where Z represents a hydrogen atom, an alkyli or alkaline earth metal or a hydrocarbon radical.
3. As a new bactericidal or bacteriostatic agent, an aliphatic substance containing from 10 to 21 carbon atoms and having the general formula CHCOOZ, R!
where R and R represent aliphatic hydrocarbon radicals such as alkyl or alkylene, and where Z represents a hydrogen atom, an alkali or alkyline earth metal or a hydrocarbon radical, and Where the carboxyl group is attached near the middle of the chain.
4. As a new bactericidal or bacteriostatic agent especially applicable to acid-fast bacteria, a substance which is a member of the group consisting of aliphatic acids, alkali and alkaline earth metal salts thereof and hydrocarbon esters thereof, in which the carboxyl group is located at a point removed from the end of the chain, said substance containing from 10 to 21 carbon atoms.
5. A composition as defined in claim 4, and containing from 15 to 18 carbon atoms.
6. As a new bactericidal or bacteriostatic agent especially applicable to acid-fast bacteria, a substance which is a member of the group consisting of aliphatic acids, alkali and alkaline earth metal salts thereof, and
hydrocarbon esters thereof, in which the carboxyl group is attached to a carbon atom at approximately the center of the chain, said substance containing from 10 to 21 carbon atoms.
7. A composition as defined in claim 6, and
containing from 15 to 1 8 carbon atoms. ROGER ADAMS.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US329077A US1873732A (en) | 1928-12-28 | 1928-12-28 | Bactericide applicable to acid-fast bacteria |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US329077A US1873732A (en) | 1928-12-28 | 1928-12-28 | Bactericide applicable to acid-fast bacteria |
Publications (1)
Publication Number | Publication Date |
---|---|
US1873732A true US1873732A (en) | 1932-08-23 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US329077A Expired - Lifetime US1873732A (en) | 1928-12-28 | 1928-12-28 | Bactericide applicable to acid-fast bacteria |
Country Status (1)
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US (1) | US1873732A (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2461336A (en) * | 1946-04-01 | 1949-02-08 | Standard Oil Dev Co | Manufacture of glutaric acid |
US2935973A (en) * | 1957-02-18 | 1960-05-10 | Du Pont | Hydrocarbon fuels having improved antiknock properties |
US2979455A (en) * | 1958-10-03 | 1961-04-11 | Commercial Solvents Corp | Process for the control of bacteria |
US3001935A (en) * | 1959-05-13 | 1961-09-26 | Commercial Solvents Corp | Process for the control of bacteria in water flooding operations |
US3003915A (en) * | 1961-10-10 | Method of destroying lactobacilli em- | ||
US20080188457A1 (en) * | 2007-02-02 | 2008-08-07 | Braincells, Inc. | Modulation of Neurogenesis with Biguanides and GSK3-beta Agents |
US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
EP2258358A2 (en) | 2005-08-26 | 2010-12-08 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
EP2275096A2 (en) | 2005-08-26 | 2011-01-19 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
WO2011063115A1 (en) | 2009-11-19 | 2011-05-26 | Braincells Inc. | Combination of nootropic agent with one or more neurogenic or neurogenic sensitizing agents for stimulating or increasing neurogenesis |
WO2011091033A1 (en) | 2010-01-20 | 2011-07-28 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
US7998971B2 (en) | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
EP2377530A2 (en) | 2005-10-21 | 2011-10-19 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
-
1928
- 1928-12-28 US US329077A patent/US1873732A/en not_active Expired - Lifetime
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3003915A (en) * | 1961-10-10 | Method of destroying lactobacilli em- | ||
US2461336A (en) * | 1946-04-01 | 1949-02-08 | Standard Oil Dev Co | Manufacture of glutaric acid |
US2935973A (en) * | 1957-02-18 | 1960-05-10 | Du Pont | Hydrocarbon fuels having improved antiknock properties |
US2979455A (en) * | 1958-10-03 | 1961-04-11 | Commercial Solvents Corp | Process for the control of bacteria |
US3001935A (en) * | 1959-05-13 | 1961-09-26 | Commercial Solvents Corp | Process for the control of bacteria in water flooding operations |
EP2258358A2 (en) | 2005-08-26 | 2010-12-08 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
EP2258359A2 (en) | 2005-08-26 | 2010-12-08 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
EP2258357A2 (en) | 2005-08-26 | 2010-12-08 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
EP2275096A2 (en) | 2005-08-26 | 2011-01-19 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
EP2275095A2 (en) | 2005-08-26 | 2011-01-19 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
EP2377530A2 (en) | 2005-10-21 | 2011-10-19 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
EP2382975A2 (en) | 2006-05-09 | 2011-11-02 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
US7998971B2 (en) | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
US20080188457A1 (en) * | 2007-02-02 | 2008-08-07 | Braincells, Inc. | Modulation of Neurogenesis with Biguanides and GSK3-beta Agents |
WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
WO2011063115A1 (en) | 2009-11-19 | 2011-05-26 | Braincells Inc. | Combination of nootropic agent with one or more neurogenic or neurogenic sensitizing agents for stimulating or increasing neurogenesis |
WO2011091033A1 (en) | 2010-01-20 | 2011-07-28 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
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