WO2014150268A1 - Compounds and uses thereof for the modulation of hemoglobin - Google Patents
Compounds and uses thereof for the modulation of hemoglobin Download PDFInfo
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- WO2014150268A1 WO2014150268A1 PCT/US2014/022769 US2014022769W WO2014150268A1 WO 2014150268 A1 WO2014150268 A1 WO 2014150268A1 US 2014022769 W US2014022769 W US 2014022769W WO 2014150268 A1 WO2014150268 A1 WO 2014150268A1
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- optionally substituted
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- RUVPNKWEUVSVRG-QJDWYWKQSA-N CC(C)(CC1)C[C@@H]1[I](CC(C1)C1CC1C2=CCC=C2)([C@@]1(C)F)=[I]C Chemical compound CC(C)(CC1)C[C@@H]1[I](CC(C1)C1CC1C2=CCC=C2)([C@@]1(C)F)=[I]C RUVPNKWEUVSVRG-QJDWYWKQSA-N 0.000 description 1
- XFQGQDCPXKNECY-UHFFFAOYSA-N CNP(O)(OCOC(SC)=O)=O Chemical compound CNP(O)(OCOC(SC)=O)=O XFQGQDCPXKNECY-UHFFFAOYSA-N 0.000 description 1
- DFVCFSLAVONZDZ-UHFFFAOYSA-N IC1NCCOC1 Chemical compound IC1NCCOC1 DFVCFSLAVONZDZ-UHFFFAOYSA-N 0.000 description 1
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- ring b is joined to L 1 or L 2 via a nitrogen atom.
- R 3 is joined to L 2 via a nitrogen atom.
- salt refers to art sonic compound formed between an acid and a base.
- salts include, without limitation, alkali metal, alkaline earth metal, and ammonium salts.
- ammonium salts include, salts containing protonated nitrogen bases and alkylated nitrogen bases.
- Exemplary, and non-limiting cations useful in pharmaceutically acceptable salts include IMa, K, Rb, Cs, NH Ca, Ba, imidazollum, and ammonium cations based on naturally occurring amino acids.
- the terms also include relieving the disease or conditions, e.g., causing the regression of clinical symptoms.
- the terms further include achieving a therapeutic benefit and/or a prophylactic benefit.
- therapeutic benefit is meant eradication or amelioration of the underlying disorder being treated.
- a therapeutic benefit is achieved with the eradication or amelioration of one or more of the physiological symptoms associated with the underlying disorder such that an improvement is observed in the individual, notwithstanding that the individual is still be afflicted with the underlying disorder.
- the compositions are administered to an individual at risk of developing a particular disease, or to an Individual reporting one or more of the physiological symptoms of a disease, even though a diagnosis of this disease has not been made.
- a pharmaceutically active compound can be modified chemically to render it less active or inactive, but the chemical modification is such that an active form of the compound is generated by metabolic or other biological processes.
- a prodrug may have, relative to the drug, altered metabolic stability or transport characteristics, fewer side effects or lower toxicity. For example, see the reference Nogrady, 1985, Medicinal Chemistry A Biochemical Approach , Oxford University Press, New York, pages 388-392. Prodrugs can also be prepared using compounds that are not drugs.
- Y is a or ⁇ substituted relative to the -L 1 L 2 R 3 ;
- L l is a bond
- each R 1 and 2 independentl is hydrogen, d-Cg alkyl, C 3 -C 3 cycloalkyl, Cg-do aryl, 4- 10 roembered heterocycle or 5- 10 membered heteroaryl, each containing u p to 5 ring heteroatoms, wherein the heteroatom is selected from the group consisting of O, N, S, and oxidized forms of N and S, wherein each alkyl, cycloalkyl, heterocycle, aryi or heteroaryl is optionally substituted, or R 1 and R" together with the n itrogen atom they are attached to form an optionally substituted 4-7 membered heterocycle;
- ring B is a optionally substituted C 6 ⁇ Ci 0 aryl, optionally substituted 5-10 mem bered heteroaryl having 1-3 nitrogen atoms or oxidized forms of , or optionally su bstituted 4-10 mem bered heterocycle containing up to 5 ring heteroatoms, wherein the heteroatom is selected from the group consisting of O, , S, and oxidized forms of N and S;
- each Y and Z is independently CR 10 R" O, S, SO, S0 2, or NR 10 ; each 0 and R N
- V A and V " independentiy are C r C 6 alkoxy; or V 1 and V together with the ca rbon atom they are tached to form a ring of formula:
- L 2 is OO or S0 2 ;
- FT ' is hydrogen or a prodrug moiety R
- t is 0. in certain embodiments, t is 1. in certain embodiments, t is 2. in certain embodiments, t is 3,
- L 1 is a bond
- each P and Q is independently selected from CHR 17 , NCOR 15 , NC0 2 R 15 ; N-O, 0, S, SO, and S0 2 ;
- each R" Independently is d- alkyi; C3-C3 cycloalkyi, 4-9 membered heterocycie, or a 5-10 membered heteroaryl, containing at least 1 basic nitrogen moiety; or 2 R 13 together with the nitrogen atom they are bonded to for a 4-9 member heterocycie substituted with at least 1 amino, C r C 6 alkyi amino, or di C C 6 aSky!atnino group.
- preferred embodiments are compounds wherein NR 3 V 5 is morpholino.
- R s is lower alky! ⁇ e.g. r C 6 aikyi), aspect,.
- R is: wherein X 1 , Y" and X 2 are as defined herein.
- heterocyciyi C 6 --C 10 aryl, C3-C9 heteroaryi, C(W Z )X 3 , PO(X3 ⁇ 4, and S0 2 X 3 ;
- said moiety is selected from the group consisting of CQ 2 H, SO 3 ⁇ 4 H, S0 2 H,
- Step 2 To a solution of (S)-(2- ⁇ hydroxymethyl)pyrrolidin-l-yl) ⁇ l-isopropyl-lH- pyrazoi-5-yl)methanone (120 mg, 0.51 mmoi) and 2,6-dihydroxybenzaidehyde (0.09 g, 0.66 mmoi) in THF (4 mL) waas added PPh 3 (Polymer supported, 640 mg, 0.77 mmoi) and DIAD (0.16 mL, 0.77 mmoi) at 0 °C. After stirred at room temperature for 1 h, it was diluted with AcCN, the insoluble materia!
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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Abstract
Description
Claims
Priority Applications (22)
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MYPI2015002271A MY191087A (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
EA201591432A EA034922B1 (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
JP2016501058A JP6426694B2 (en) | 2013-03-15 | 2014-03-10 | Compounds for the modification of hemoglobin and their use |
CN201480015944.4A CN105073728A (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
US14/776,726 US20160083343A1 (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
MX2015011445A MX2015011445A (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin. |
BR112015021985-3A BR112015021985B1 (en) | 2013-03-15 | 2014-03-10 | PHARMACEUTICALLY ACCEPTABLE COMPOUNDS OR SALTS THEREOF, THEIR USES AND COMPOSITION |
CA2903220A CA2903220C (en) | 2013-03-15 | 2014-03-10 | Aldehyde compounds and uses thereof for the modulation of hemoglobin |
KR1020157024781A KR102280614B1 (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
ES14770695T ES2852054T3 (en) | 2013-03-15 | 2014-03-10 | Compounds and their uses for modulation of hemoglobin |
AU2014237340A AU2014237340C1 (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
SG11201507320QA SG11201507320QA (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
AP2015008721A AP2015008721A0 (en) | 2013-03-15 | 2014-03-10 | Compounds and uses thereof for the modulation of hemoglobin |
IL241060A IL241060B (en) | 2013-03-15 | 2015-09-02 | Compounds and uses thereof for the modulation of hemoglobin |
SA517382253A SA517382253B1 (en) | 2013-03-15 | 2015-09-09 | Compounds and Uses Thereof for the Modulation of Hemoglobin |
SA515361026A SA515361026B1 (en) | 2013-03-15 | 2015-09-09 | Compounds and uses thereof for the modulation of hemoglobin |
US16/127,776 US20190010121A1 (en) | 2013-03-15 | 2018-09-11 | Compounds and uses thereof for the modulation of hemoblogin |
AU2018260808A AU2018260808B2 (en) | 2013-03-15 | 2018-11-06 | Compounds and uses thereof for the modulation of hemoglobin |
US16/186,275 US11053195B2 (en) | 2013-03-15 | 2018-11-09 | Compounds and uses thereof for the modulation of hemoglobin |
US16/446,331 US10450269B1 (en) | 2013-11-18 | 2019-06-19 | Compounds and uses thereof for the modulation of hemoglobin |
AU2020203882A AU2020203882A1 (en) | 2013-03-15 | 2020-06-12 | Compounds and uses thereof for the modulation of hemoglobin |
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US16/186,275 Continuation US11053195B2 (en) | 2013-03-15 | 2018-11-09 | Compounds and uses thereof for the modulation of hemoglobin |
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