WO2014150268A1 - Compounds and uses thereof for the modulation of hemoglobin - Google Patents

Compounds and uses thereof for the modulation of hemoglobin Download PDF

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Publication number
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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WIPO (PCT)
Prior art keywords
optionally substituted
independently
ring
group
hydrogen
Prior art date
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PCT/US2014/022769
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English (en)
French (fr)
Inventor
Qing Xu
Zhe Li
Stephen L. Gwaltney Ii
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Global Blood Therapeutics Inc
Original Assignee
Global Blood Therapeutics Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US13/815,735 external-priority patent/US8952171B2/en
Priority to CA2903220A priority Critical patent/CA2903220C/en
Priority to JP2016501058A priority patent/JP6426694B2/ja
Priority to ES14770695T priority patent/ES2852054T3/es
Priority to AU2014237340A priority patent/AU2014237340C1/en
Priority to CN201480015944.4A priority patent/CN105073728A/zh
Priority to KR1020157024781A priority patent/KR102280614B1/ko
Priority to BR112015021985-3A priority patent/BR112015021985B1/pt
Priority to US14/776,726 priority patent/US20160083343A1/en
Priority to SG11201507320QA priority patent/SG11201507320QA/en
Priority to EP14770695.6A priority patent/EP2970196B1/en
Priority to MYPI2015002271A priority patent/MY191087A/en
Application filed by Global Blood Therapeutics Inc filed Critical Global Blood Therapeutics Inc
Priority to EA201591432A priority patent/EA034922B1/ru
Priority to MX2015011445A priority patent/MX379228B/es
Priority to AP2015008721A priority patent/AP2015008721A0/xx
Publication of WO2014150268A1 publication Critical patent/WO2014150268A1/en
Priority to IL241060A priority patent/IL241060B/en
Priority to SA517382253A priority patent/SA517382253B1/ar
Priority to SA515361026A priority patent/SA515361026B1/ar
Anticipated expiration legal-status Critical
Priority to US16/127,776 priority patent/US20190010121A1/en
Priority to AU2018260808A priority patent/AU2018260808B2/en
Priority to US16/186,275 priority patent/US11053195B2/en
Priority to US16/446,331 priority patent/US10450269B1/en
Priority to AU2020203882A priority patent/AU2020203882A1/en
Ceased legal-status Critical Current

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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
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    • 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
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    • 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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  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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AP2015008721A AP2015008721A0 (en) 2013-03-15 2014-03-10 Compounds and uses thereof for the modulation of hemoglobin
EA201591432A EA034922B1 (ru) 2013-03-15 2014-03-10 Соединения и их применения для модуляции гемоглобина
ES14770695T ES2852054T3 (es) 2013-03-15 2014-03-10 Compuestos y usos de los mismos para la modulación de hemoglobina
AU2014237340A AU2014237340C1 (en) 2013-03-15 2014-03-10 Compounds and uses thereof for the modulation of hemoglobin
CN201480015944.4A CN105073728A (zh) 2013-03-15 2014-03-10 化合物及其用于调节血红蛋白的用途
KR1020157024781A KR102280614B1 (ko) 2013-03-15 2014-03-10 헤모글로빈 조정을 위한 화합물 및 이의 용도
BR112015021985-3A BR112015021985B1 (pt) 2013-03-15 2014-03-10 Compostos ou sais farmaceuticamente aceitáveis dos mesmos, respectivos usos e composição
JP2016501058A JP6426694B2 (ja) 2013-03-15 2014-03-10 ヘモグロビンの修飾のための化合物及びその使用
SG11201507320QA SG11201507320QA (en) 2013-03-15 2014-03-10 Compounds and uses thereof for the modulation of hemoglobin
EP14770695.6A EP2970196B1 (en) 2013-03-15 2014-03-10 Compounds and uses thereof for the modulation of hemoglobin
MYPI2015002271A MY191087A (en) 2013-03-15 2014-03-10 Compounds and uses thereof for the modulation of hemoglobin
CA2903220A CA2903220C (en) 2013-03-15 2014-03-10 Aldehyde compounds and uses thereof for the modulation of hemoglobin
MX2015011445A MX379228B (es) 2013-03-15 2014-03-10 Compuestos y usos de estos para la modulación de la hemoglobina.
US14/776,726 US20160083343A1 (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 Preparations and their use to regulate hemoglobin levels
SA515361026A SA515361026B1 (ar) 2013-03-15 2015-09-09 مركبات واستخداماتها لتعديل الهيموجلوبين
SA517382253A SA517382253B1 (ar) 2013-03-15 2015-09-09 مركبات واستخداماتها لتعديل الهيموجلوبين
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
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