WO1989002741A1 - Inhibitors of hiv-reverse transcriptase to treat aids - Google Patents
Inhibitors of hiv-reverse transcriptase to treat aids Download PDFInfo
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- WO1989002741A1 WO1989002741A1 PCT/US1988/003114 US8803114W WO8902741A1 WO 1989002741 A1 WO1989002741 A1 WO 1989002741A1 US 8803114 W US8803114 W US 8803114W WO 8902741 A1 WO8902741 A1 WO 8902741A1
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- immunodeficiency virus
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
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- 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
- A61K31/075—Ethers or acetals
- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
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- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/66—Phosphorus compounds
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compounds selected from a group consisting of lomofungin, paulomycin A, mycorhodin, antibiotic 357b, phenolphthalein diacetate, phenolphthalexon, thymophthalexon, U-64161, U-46768, U-18230, U-21052A, U-23278D, U-45483, U-57057, U-62455, U-12978E, U-42529, U-23034, diazaquinomycin A, maduramycin, and chelocardin or salts thereof can be used to treat humans infected with one or more than one strain of a human immunodeficiency virus.
Description
INHIBITORS OF HIV-REVbRSE TRANSCRIPTASE TO TREAT AIDS Field of the Invention This invention is a novel treatment of patients infected with a human immunodeficiency virus. Background of the Invention The compounds used to practice the method claimed in this invention are all known in the art, however, none of the compounds are known to be useful to treat humans infected with human immunodeficiency virus or strains thereof. An estimated one to one and one-half million people in the United States are infected with a human retrovirus, the human immunodeficiency virus type I, HIV-1, which is the etiological agent of acquired immunodeficiency syndrome, AIDS, Norman, C., Science 661-662 (1986). Of those infected, an estimated two hundred and fifty thousands people will clevelop AIDS in the next five years, Curran, J.W., et al., Science, 1352-1357 (1985). On March 20, 1987, the FDA approved the use of the compound, zidovudine (AZT), to treat AIDS patients with Åa recent initial episode of pneumocystis carinii pneumonia, AIDS patients with conditions other than pneumocystis carinii pneumonia or patients infected with the virus with an absolute CD4 lymphocyte count of less than 200/mm3 in the peripheral blood. AZT is a known inhibitor of viral reverse transcriptase, an enzyme necessary for human immunodeficiency virus replication. It is known in the art that certain antibiotics and polyanionic dyes inhibit retrovirus reverse transcriptase. None of the compounds claimed in this invention were known to specifically inhibit human immunodeficiency virus reverse transcriptase. Summarv of the Invention This invention is a method for treating a human infected with one or more than one strain of a human immunodeficiency virus which comprises administering an effective amount of a compound selected from the group consisting of lomofungin, paulomycin A, mycorhodin, antibiotic 357b, phenolphthalein diacetate, phenolphthalexon, thymophthalexon, U-64161, U-46768, U-18230, U-21052A, U-23278D, U 45483,. U-57057, U-62455, U-12978E, U-42529, U-23034, diazaquinomycin A, maduramycin, and chelocardin or salts thereof, to the infected human. Detailed Description of the Invention In this document, the term human immunodeficiency virus means human immunodeficiency virus type I, human immunodeficiency virus type II, or strains, apparent to one skilled in the art, which belong to the same viral family and which create similar physiological effects in humans as human immunodeficiency virus types I or II. The structural formulas, if known, of each of the compounds used to practice the method claimed in this invention are given in the structure charts. The availability or preparation of these compounds is given or described in the following list: lomofungin, U.S. Patent 3,359,165; paulomycin A, U.S. Patent 4,335,108; mycorhodin, Chem. Ab. 67:52709r (1968); antibiotic 357b, U.S. Patent 4,267,112; phenolphthalein diacetate, J. Chromatogr. 45 324 (1969); phenolphthalexon, Chem. Abs. 71:108733w (1969); thymophthalexon, Chem. Abs. 63:6302b (1965); U-64164, commercially available; U-46768, J. Org. Chem., 5001-5002 (1986); U-18230, commercially available; U-21052A, Derwent Abstract No. 2550F; U-23278D, Derwent Abstract No. 35,121F; U-45483, commercially available; U-57057, U.S. Patent 3,530,152; U-62455; Chem Abs. 71:30144h (1969); U-12978E, U.S. Patent 3,311,638; U-42529, U.S. Patent 3,691,217; and U-23034, Chem. Abs. 97:34852x (1982); diazaquinomycin A, Tetrahedron Letters, 3643-3646 (1983); maduramycin, Derwent Abstract No. 32090X/18; chelocardin, Derwent Abstract No. 14390. These compounds as depicted in the structure charts or pharmacologically acceptable salts thereof can be used and administered in practicing the method claimed in this invention. Pharmacologically acceptable salts refers to those salts of the compounds claimed in this invention which would be readily apparent to a manufacturing pharmaceutical chemist to be equivalent to the parent compound in properties such as formulation, stability, patient acceptance and bioavailablility. Those skilled in the art would know how to formulate the compounds used to practice the method claimed in this invention into appropriate pharmaceutical dosage forms. Examples of the dosage forms include oral formulations, such as tablets or capsules, or parenteral formulations, such as sterile solutions. When the compounds used to practice the method claimed in this invention-are administered orally, an effective amount is from about 1 to 100 mg per kg per day. A typical unit dose for a 70 kg human would be from about 200 mg to 1000 mg taken one to four times per day. Either solid or fluid dosage forms can be prepared for oral administration. Solid compositions are prepared by mixing the compounds used to practice the method claimed in this invention with conventional ingredients such as talc, magnesium stearate, dicalcium phosphate, magnesium aluminum silicate, calcium sulfate, starch, lactose, acacia, methyl cellulose, or functionally similar pharmaceutical diluents and carriers. Capsules are prepared by mixing the compounds used to practice the method claimed in this invention with an inert pharmaceutical diluent and placing the mixture into an appropriately sized hard gelatin capsule. Soft gelatin capsules are prepared by machine encapsulation of a slurry of the compounds used to practice the method claimed in this invenition with an acceptable inert oil such as vegetable oil or light liquid petrolatum. Syrups are prepared by dissolving the compounds used to practice the method claimed in this invention in an aqueous vehicle and adding sugar; aromatic flavoring agents and preservatives. Elixirs are prepared using a hydroalcoholicvehicle such as ethanol, suitable,sweeteners such as sugar or saccharin and an aromatic flavoring agent. Suspensions are prepared with an aqueous vehicle and a suspending agent such as acacia, tragacanth, or methyl cellulose. When the compounds used to practice the method claimed in this invention are administered parenterally, it can be given by injection or by intravenous infusion. An effective amount is from about 1 to 100 mg per kg per day. Parenteral solutions are prepared by dissolving the compounds used to practice the method claimed in this invention in water and filter sterilizing the solution before placing in a suitable sealable vial or ampule. Parenteral suspensions are prepared in substantially the same way except a sterile suspension vehicle is used and the compounds used to practice the method claimed in this invention are sterilized with ethylene oxide or suitable gas before it is suspended in the vehicle. The exact route of administration, dose, or frequency of administration would be readily determined by those skill in the art and is dependant on the age, weight, general physical condition, or other clinical symptoms specific to the patient to be treated. Patients to be treated would be those ndividuals: 1) infected with one or more than one strain of a human immunodeficiency virus as determined by the presence of either measurable viral antibody or antigen in the serum and 2) having either a symptomatic AIDS defining infection such -as i) disseminated histoplasmosis, ii) isoporiasis, iii) bronchial and pulmonary candidiasis including pneumocystis pneumonia iv) non-Hodgkin's lymphoma or v) Kaposi's sarcoma and being less than sixty years old; or having an absolute CD4 lymphocyte count of less than 200/mm3 in the peripheral blood. Treatment would consist of maintaining an inhibitory level of the compounds of this invention in the patient at all times and would continue until the occurrence of a second symptomatic AIDS defining infection indicates alternate therapy is needed. Without further elaboration, those skilled in the art can practice the present invention to its fullest extent. The following detailed examples further describe how to the compounds claimed in this invention to treat humans infected with one or more than one strain of a human immunodeficiency virus. These examples are merely illustrative and are not limitations of the preceding disclosure. Those skilled'in the art will promptly recognize appropriate variations from the examples. In each example, any compound claimed in this invention could replace the compound used in the particular example. Example 1 Hard Gelatin Capsules One thousand two-piece hard gelatin capsules for oral use, each capsule containing 50 mg of phenolphthalein diacetate, are prepared from the following: Phenolphthalein diacetate 50 gm Lactose 100 gm Cornstarch 20 gm Talc 20 gm Magnesium Stearate 2 gm The phenolphthalein diacetate is added to the other ingredients, mixed and encapsulated in the usual manner. Examnle 2 Tablets One thousand tablets, each containing 50 mg of phenolphthalein diacetate, are prepared from the following: Phenolphthalein diacetate 50 gm Lactose 75 gm Cornstarch 50 gm Magnesium Stearate 4 gm Light liquid petrolatum 5 gm The phenolphthalein diacetate is added to the other ingredients, mixed and slugged. The slugs are broken down by forcing through a number sixteen screen. The resulting granules are then compressed into tablets. Example 3 Parenteral solution A sterile aqueous solution for parenteral intravenous injection containing 150 mg of phenolphthalein diacetate in one liter of solution is prepared from the following: Phenolphthalein diacetate 150 mg Water for injection, qs 1000 mg The phenolphthalein diacetate sodium salt is sterilized, added to the sterile water, filled into sterile containers and sealed. The utility of this invention is demonstrated by the ability of the compounds used to practice the method claimed in this invention to inhibit viral reverse transcriptase, an enzyme essential for human immunodeficiency virus replication. This enzyme has characteristics which differentiate it from other known cellular polymerases and it is a unique enzyme which is not found in uninfected cells. Viral reverse transcriptase is found in extracts from bacterial clones prepared according to the procedure described by Goff, S. P., et al., Journal of Virology, 743-745 (1986). Inhibition of this enzyme is determined in a cell free assay which measures the level of radioactive precursors incorporated into DNA. Extracts prepared according to the procedure of Kleid, D. G., et al., Science, 1125-1129 (1981) are incubated in a mixture of inhibitor, 20 mM dithiothreitol, 60 mM sodium chloride, 0.05% NP-40, 10 mM magnesium chloride, 50 mM Tris pH 8.3, 10 pM [355]-labeled deoxynuleoside-5'-triphosphate, 10 pg/ml RNA template (poly rC or poly rG) and 5 pg/ml DNA primer (oligo dG or oligo dT) for 30 minutes at 37"C. Incorporation of radio-labeled percursor is determined by spotting aliquots of the reaction mixture on DE81 paper, washing the papers to remove unincorporated percursor, drying and determining counts. Table 1 contains the results of the assay for the compounds used to practice the method claimed in this invention. TABLE 1 Compounds % Inhibition lomofungin 18 paulomycin A 22 mycorhodin 66 antibiotic 357b 31 pheno lphthalein diacetate 19 pheno lphthalexon 21 thymolphthalexon 30 U-64161 16 U-46768 21 U-18230 22 U-21052A 29 U-23278D 22 U-45483 23 U-57057 24 U-62455 21 U-12978E 18 U-42529 56 U-23034 27 D iaz aquinomycin A* 76/77 Maduramycin* 83/79 Chelocardin* 74/75 Diazaquinomycin A, which is rather insoluble in DMF or water, was tested as a suspension. * These data originate from two independent experiments. STRUCTURE CHART Name Structure lomofungin Structure unknown paulomycin A EMI7.1 antibiotic 357b EMI7.2 phenolphthalein diacetate EMI7.3 STRUCTURE CHART (continued) Name Structure phenolphthalexon EMI8.1 mycorhodin Structure unknown EMI8.2 isobenzofuranimine EMI8.3 Name U-46768 U-18230 U-21052A U-23278D STRUCTURE CHART (continued) Structure EMI9.1 STRUCTURE CHART (continued) Name Structure U-45483 U-57057 U-62455 U-12978E EMI10.1 STRUCTURE CHART (continued) Name Structure U-42529 U-23034 diazaquinomycin A EMI11.1 STRUCTURE CHART (continued) Name Structure maduramycin structure unknown chelocardin EMI12.1 or salt thereof.
Claims
1. A composition for treating a human infected with one or more than one strain of a human immunodeficiency virus comprising a compound selected from the group consisting of
lumofungin structure unknown
paulomycin A
EMI13.1
antibiotic 357b
EMI13.2
phenolphthale in diacetate
EMI13.3
phenolphthalexon
EMI14.1
mycorhodin Structure unknown
EMI14.2
isobenzofuranimine
EMI14.3
U-46768
U-18230
EMI15.1
U-21052A
EMI15.2
U-23278D
EMI15.3
U-45483
U-57057
U-62455
U-12978E
EMI16.1
U-42529
U-23034
EMI17.1
diazaquinomycin A
EMI17.2
maduramycin structure unknown chelocardin
EMI18.1
or salt thereof, 2. A composition according to claim 1 where the human is infected with human immunodeficiency virus type I.
3. A composition according to claim 1 where the human is infected with human immunodeficiency virus type II.
4. A composition according to claim 1 where the administration is oral.
5. A composition according to claim 1 where the effective amount is from about 1 to 100 mg per kg per day.
6. A composition according to claim 1 where the administration is parenteral.
7. A composition according to claim 4 where the administration is by injection.
8. A composition according to claim 4 where the administration is by intravenous fusion.
9. A composition according to claim 1 where the compound isselected from a group consisting of lomofungin, paulomycin A, mycorhodin, and antibiotic 357b or salts thereof.
10. A composition according to claim 1 where the compound is selected from a group consisting of phenolphthalein diacetate, phenolphthalexon, and thymophthalexon or salts thereof.
11. A composition according to claim 1 where the compound is selected from a group consisting of U-18230, U-21052A, U-23278D, U45483, U-57057, and U-62455 or salts thereof.
12. A composition according to claim 1 where the compound is selected from a group consisting of U-12978E, U-42529, and U-23034 or salts thereof.
13. A composition according to claim 1 where the compound is selected from a group consisting of U-64164 and U-46768.
14. A composition according to claim 1 where the compound is selected from a group consisting of diazaquinomycin A, maduramycin, and chelocardin or salts thereof.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US107,123 | 1979-12-26 | ||
US10170687A | 1987-09-28 | 1987-09-28 | |
US101,706 | 1987-09-28 | ||
US10712387A | 1987-10-09 | 1987-10-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1989002741A2 WO1989002741A2 (en) | 1989-04-06 |
WO1989002741A1 true WO1989002741A1 (en) | 1989-04-06 |
Family
ID=26798544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1988/003114 WO1989002741A1 (en) | 1987-09-28 | 1988-09-16 | Inhibitors of hiv-reverse transcriptase to treat aids |
Country Status (2)
Country | Link |
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AU (1) | AU2527488A (en) |
WO (1) | WO1989002741A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7342038B2 (en) * | 1997-11-20 | 2008-03-11 | President And Fellow Of Harvard College | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation |
US8754054B2 (en) | 2010-07-09 | 2014-06-17 | Albany Molecular Research, Inc. | Antibacterial compounds, methods of making them, and uses thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1617925A1 (en) * | 1966-11-02 | 1970-01-22 | Upjohn Co | Pharmaceutical preparation having an antibiotic effect and process for its manufacture |
-
1988
- 1988-09-16 WO PCT/US1988/003114 patent/WO1989002741A1/en unknown
- 1988-09-16 AU AU25274/88A patent/AU2527488A/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1617925A1 (en) * | 1966-11-02 | 1970-01-22 | Upjohn Co | Pharmaceutical preparation having an antibiotic effect and process for its manufacture |
Non-Patent Citations (2)
Title |
---|
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Vol. 3, No. 6, June 1973, F.R. CANO et al., "Lomofungin, an Inhibitor of Deoxyribonucleic Acid-Dependant Ribonucleic Acid Polymerases", pages 723-728. * |
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 92, No. 5, 11 March 1970, C.D. TIPTON & K.L. RINEHART, Jr.: "Lomofungin I. Degradative Studies of a New Phenazine Antibiotic", pages 1425-1426. * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7342038B2 (en) * | 1997-11-20 | 2008-03-11 | President And Fellow Of Harvard College | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation |
US8754054B2 (en) | 2010-07-09 | 2014-06-17 | Albany Molecular Research, Inc. | Antibacterial compounds, methods of making them, and uses thereof |
Also Published As
Publication number | Publication date |
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AU2527488A (en) | 1989-04-18 |
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