CA2184695A1 - Increasing fetal hemoglobin levels using carboxylic esters - Google Patents
Increasing fetal hemoglobin levels using carboxylic estersInfo
- Publication number
- CA2184695A1 CA2184695A1 CA002184695A CA2184695A CA2184695A1 CA 2184695 A1 CA2184695 A1 CA 2184695A1 CA 002184695 A CA002184695 A CA 002184695A CA 2184695 A CA2184695 A CA 2184695A CA 2184695 A1 CA2184695 A1 CA 2184695A1
- Authority
- CA
- Canada
- Prior art keywords
- administering
- compound
- dibutyrate
- aryl
- butyroxy
- 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.)
- Abandoned
Links
- 108010044495 Fetal Hemoglobin Proteins 0.000 title abstract description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 56
- -1 ammoalkyl Chemical group 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 125000002541 furyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 239000000651 prodrug Substances 0.000 claims abstract description 5
- 229940002612 prodrug Drugs 0.000 claims abstract description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 30
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 208000007056 sickle cell anemia Diseases 0.000 claims description 9
- 201000004792 malaria Diseases 0.000 claims description 6
- PYRVZKVHVYUFHS-UHFFFAOYSA-N 1-butanoyloxybutyl butanoate Chemical compound CCCC(=O)OC(CCC)OC(=O)CCC PYRVZKVHVYUFHS-UHFFFAOYSA-N 0.000 claims description 5
- QWCZLICLKFKDBO-UHFFFAOYSA-N 1-butanoyloxyethyl butanoate Chemical compound CCCC(=O)OC(C)OC(=O)CCC QWCZLICLKFKDBO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- XRVKSDCOJNKYRH-UHFFFAOYSA-N (1-butanoyloxy-2,2-dimethylpropyl) butanoate Chemical compound CCCC(=O)OC(C(C)(C)C)OC(=O)CCC XRVKSDCOJNKYRH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- FERWQICGOAENLD-UHFFFAOYSA-N butanoyloxymethyl butanoate Chemical compound CCCC(=O)OCOC(=O)CCC FERWQICGOAENLD-UHFFFAOYSA-N 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 3
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims 6
- LZBZVXBQAJUKGA-UHFFFAOYSA-N (3-oxo-1h-2-benzofuran-1-yl) butanoate Chemical compound C1=CC=C2C(OC(=O)CCC)OC(=O)C2=C1 LZBZVXBQAJUKGA-UHFFFAOYSA-N 0.000 claims 3
- JETAWAMBWFMMDD-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl butanoate Chemical compound CCCC(=O)OC(C)OC(=O)OCC JETAWAMBWFMMDD-UHFFFAOYSA-N 0.000 claims 3
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims 3
- ZAKOWWREFLAJOT-ADUHFSDSSA-N [2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate Chemical group CC(=O)OC1=C(C)C(C)=C2OC(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-ADUHFSDSSA-N 0.000 claims 3
- GYKLFBYWXZYSOW-UHFFFAOYSA-N butanoyloxymethyl 2,2-dimethylpropanoate Chemical compound CCCC(=O)OCOC(=O)C(C)(C)C GYKLFBYWXZYSOW-UHFFFAOYSA-N 0.000 claims 3
- POSXGLRSYWUWNB-UHFFFAOYSA-N butanoyloxymethyl octanoate Chemical compound CCCCCCCC(=O)OCOC(=O)CCC POSXGLRSYWUWNB-UHFFFAOYSA-N 0.000 claims 3
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 3
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- 210000004027 cell Anatomy 0.000 description 18
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- A61K31/352—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 condensed with carbocyclic rings, e.g. methantheline
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
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- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
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- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US206,690 | 1994-03-07 | ||
| US08/206,690 US5569675A (en) | 1994-03-07 | 1994-03-07 | Methods of using carboxylic acid esters to increase fetal-hemoglobin levels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2184695A1 true CA2184695A1 (en) | 1995-09-14 |
Family
ID=22767519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002184695A Abandoned CA2184695A1 (en) | 1994-03-07 | 1995-03-06 | Increasing fetal hemoglobin levels using carboxylic esters |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5569675A (OSRAM) |
| EP (1) | EP0793488A1 (OSRAM) |
| JP (1) | JPH09510202A (OSRAM) |
| KR (1) | KR970701540A (OSRAM) |
| CN (1) | CN1148338A (OSRAM) |
| AU (1) | AU1980695A (OSRAM) |
| BR (1) | BR9507010A (OSRAM) |
| CA (1) | CA2184695A1 (OSRAM) |
| IL (1) | IL112896A0 (OSRAM) |
| MX (1) | MX9603885A (OSRAM) |
| WO (1) | WO1995024189A1 (OSRAM) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5880152A (en) * | 1995-10-06 | 1999-03-09 | Vertex Pharmaceuticals, Inc. | Butyrate prodrugs derived from lactic acid |
| US5883123A (en) * | 1995-10-06 | 1999-03-16 | Vertex Pharmaceuticals, Inc. | Butyrate prodrugs derived from lactic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5025029A (en) * | 1986-10-10 | 1991-06-18 | Children's Hospital Medical Center Of Northern California | Method for augmenting fetal hemoglobin |
| US4822821A (en) * | 1986-10-10 | 1989-04-18 | Children's Hospital Medical Center Of Northern California | Method for augmenting fetal hemoglobin |
| EP0302349B1 (en) * | 1987-07-30 | 1993-09-29 | Bar Ilan University | Biologically active carboxylic acid esters |
| US5216004A (en) * | 1990-09-13 | 1993-06-01 | Children's Hospital Medical Center Of North California | Method for preventing malaria |
| US5439939A (en) * | 1992-03-17 | 1995-08-08 | Children's Hospital Medical Center Of Northern California | Pharmaceutical compositions and methods using isobutyramide for treating betaglobin disorders |
| AU679818B2 (en) * | 1993-11-10 | 1997-07-10 | Sloan-Kettering Institute For Cancer Research | Butyric ester cyto-differentiating agents |
-
1994
- 1994-03-07 US US08/206,690 patent/US5569675A/en not_active Expired - Fee Related
-
1995
- 1995-03-06 IL IL11289695A patent/IL112896A0/xx unknown
- 1995-03-06 JP JP7523569A patent/JPH09510202A/ja active Pending
- 1995-03-06 KR KR1019960704912A patent/KR970701540A/ko not_active Withdrawn
- 1995-03-06 MX MX9603885A patent/MX9603885A/es unknown
- 1995-03-06 EP EP95912749A patent/EP0793488A1/en not_active Withdrawn
- 1995-03-06 WO PCT/US1995/002769 patent/WO1995024189A1/en not_active Ceased
- 1995-03-06 CA CA002184695A patent/CA2184695A1/en not_active Abandoned
- 1995-03-06 BR BR9507010A patent/BR9507010A/pt not_active Application Discontinuation
- 1995-03-06 CN CN95192966A patent/CN1148338A/zh active Pending
- 1995-03-06 AU AU19806/95A patent/AU1980695A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1148338A (zh) | 1997-04-23 |
| BR9507010A (pt) | 1997-09-16 |
| EP0793488A1 (en) | 1997-09-10 |
| MX9603885A (es) | 1997-05-31 |
| US5569675A (en) | 1996-10-29 |
| WO1995024189A1 (en) | 1995-09-14 |
| JPH09510202A (ja) | 1997-10-14 |
| IL112896A0 (en) | 1995-06-29 |
| KR970701540A (ko) | 1997-04-12 |
| EP0793488A4 (OSRAM) | 1997-09-10 |
| AU1980695A (en) | 1995-09-25 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20000306 |