WO2014207082A1 - Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases - Google Patents

Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases Download PDF

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Publication number
WO2014207082A1
WO2014207082A1 PCT/EP2014/063467 EP2014063467W WO2014207082A1 WO 2014207082 A1 WO2014207082 A1 WO 2014207082A1 EP 2014063467 W EP2014063467 W EP 2014063467W WO 2014207082 A1 WO2014207082 A1 WO 2014207082A1
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Prior art keywords
compound
alkyl
formula
pharmaceutically acceptable
polymorph
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PCT/EP2014/063467
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English (en)
French (fr)
Inventor
David Craig Mc Gowan
Serge Maria Aloysius Pieters
Stefaan Julien Last
Werner Embrechts
Tim Hugo Maria Jonckers
Pierre Jean-Marie Bernard Raboisson
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Janssen R&D Ireland ULC
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Janssen R&D Ireland ULC
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Priority to SG11201510637UA priority Critical patent/SG11201510637UA/en
Priority to CA2913028A priority patent/CA2913028C/en
Priority to NO14738751A priority patent/NO3030563T3/no
Priority to PL14738751T priority patent/PL3030563T3/pl
Priority to SI201430476T priority patent/SI3030563T1/sl
Priority to DK14738751.8T priority patent/DK3030563T3/da
Priority to MX2018015053A priority patent/MX392130B/es
Priority to KR1020157035575A priority patent/KR102311234B1/ko
Priority to BR112015032546-7A priority patent/BR112015032546B1/pt
Priority to HK16106040.9A priority patent/HK1218116B/zh
Priority to JP2016522487A priority patent/JP6763769B2/ja
Priority to HRP20171720TT priority patent/HRP20171720T1/hr
Priority to EP14738751.8A priority patent/EP3030563B1/en
Priority to UAA201600620A priority patent/UA117590C2/uk
Priority to AU2014301089A priority patent/AU2014301089B2/en
Application filed by Janssen R&D Ireland ULC filed Critical Janssen R&D Ireland ULC
Priority to ES14738751.8T priority patent/ES2645950T3/es
Priority to NZ714267A priority patent/NZ714267B2/en
Priority to MX2015017671A priority patent/MX361527B/es
Priority to EA201690093A priority patent/EA034893B1/ru
Priority to US14/392,214 priority patent/US10385054B2/en
Priority to CN201480036233.5A priority patent/CN105473592B/zh
Publication of WO2014207082A1 publication Critical patent/WO2014207082A1/en
Priority to IL242655A priority patent/IL242655B/en
Priority to PH12015502780A priority patent/PH12015502780B1/en
Anticipated expiration legal-status Critical
Priority to IL258253A priority patent/IL258253B/en
Priority to AU2018274911A priority patent/AU2018274911B2/en
Priority to IL264402A priority patent/IL264402B/en
Priority to US16/441,213 priority patent/US10781216B2/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • This invention relates to pyrrolo[3,2-c/]pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treatment and /or therapy of diseases.
  • the present invention relates to the use of pyrrolo[3,2-c/]pyrimidine derivatives , more specifically to the use of pyrrolo[3,2-c/]pyrimidine derivatives in the treatment of viral infections, immune or inflammatory disorders, whereby the modulation, or agonism, of toll -I ike-receptors (TLRs) is involved.
  • TLRs toll -I ike-receptors
  • Toll-Like Receptors are primary transmembrane proteins characterized by an extracellular leucine rich domain and a cytoplasmic extension that contains a conserved region.
  • the innate immune system can recognize pathogen-associated molecular patterns via these TLRs expressed on the cell surface of certain types of immune cells. Recognition of foreign pathogens activates the production of cytokines and upregulation of co-stimulatory molecules on phagocytes. This leads to the modulation of T cell behaviour.
  • TLRs TLRs
  • TLR14 TLR14
  • TLR14 TLR14
  • IFN-alfa interferon
  • HCV hepatitis C virus
  • Interferon a is also given to patients in combination with other drugs in the treatment of certain types of cancer.
  • TLR 7/8 agonists are also of interest as vaccine adjuvants because of their ability to induce pronounced Th1 response.
  • Ri is H, fluorine or methyl
  • R2 is H, halogen or d-3 alkyl
  • R3 is C-i-6 alkyl optionally substituted by one or more substituents independently selected from aryloxy, heterocycle, halogen, aryl, alkylamino, dialkylamino, C-i-6 alkyl, carboxylic acid, carboxylic ester, carboxylic amide, nitrile, or C-i-6 alkoxy;
  • R3 is an alkylaryl optionally substituted by one or more substituents independently selected from halogen, aryloxy, aryl, alkylamino, dialkylamino, C-i-6 alkyl, carboxylic acid, carboxylic ester, carboxylic amide, sulfonamide, nitrile, or C-i-6 alkoxy;
  • R 4 is C-i-6 alkyl optionally substituted by one or more substituents independently selected from hydroxyl, C-i-6 alkyl, C3-7 cycloalkyl, C2-6 alkenyl or aryl optionally further substituted by C-i-6 alkyl, and C3-7 cycloalkyl optionally further substituted by C1-6 alkyl; or wherein
  • R 4 is an alkylaryl optionally substituted by one or more substituents independently selected from halogen, aryloxy, aryl, alkylamino, dialkylamino, C h alky!, carboxylic acid, carboxylic ester, carboxylic amide, sulfonamide, nitrile, or C-i ⁇ alkoxy.
  • Preferred compounds are those of formula (I) wherein R 3 is a CH 2 -aryl group (substituted or unsubstituted), and R-i, R 2 , and R 4 are described as above.
  • the compounds of formula (I) and (II) and their pharmaceutically acceptable salt, solvate or polymorph thereof have activity as pharmaceuticals, in particular as modulators of Toll-Like Receptor (especially TLR7) activity.
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of formula (I) or (II) or a pharmaceutically acceptable salt, solvate or polymorph thereof together with one or more pharmaceutically acceptable excipients, diluents or carriers.
  • a compound of formula (I) or (II) or a pharmaceutically acceptable salt, solvate or polymorph thereof according to the current invention, or a pharmaceutical composition comprising said compound of formula (I) or (II) or a pharmaceutically acceptable salt, solvate or polymorph thereof can be used as a medicament.
  • Another aspect of the invention is that a compound of formula (I) or (II) or a pharmaceutically acceptable salt, solvate or polymorph thereof, or said pharmaceutical composition comprising said compound of formula (I) or ⁇ ) or a pharmaceutically acceptable salt, solvate or polymorph thereof can be used accordingly in the treatment of any disorder in which the modulation of TLR7 is involved.
  • alkyl refers to a straight-chain or branched-chain saturated aliphatic hydrocarbon containing the specified number of carbon atoms.
  • halogen refers to fluorine, chlorine, bromine or iodine.
  • alkylaryl refers to a straight-chain or branched-chain saturated aliphatic hydrocarbon containing the specified number of carbon atoms substituted by an aryl wherein “aryl” is defined as below.
  • alkenyl refers to an alkyl as defined above consisting of at least two carbon atoms and at least one carbon-carbon double bond.
  • cycloalkyl refers to a carbocyclic ring containing the specified number of carbon atoms.
  • alkoxy refers to an alkyl (carbon and hydrogen chain) group singular bonded to oxygen like for instance a methoxy group or ethoxy group.
  • aryl means an aromatic ring structure optionally comprising one or two heteroatoms selected from N, O and S, in particular from N and O. Said aromatic ring structure may have 5, 6 or 7 ring atoms. In particular, said aromatic ring structure may have 5 or 6 ring atoms.
  • aryloxy refers to an aromatic ring structure. Said aromatic group is singularly bonded to oxygen.
  • heterocycle refers to molecules that are saturated or partially saturated and include tetrahydrofuran, dioxane or other cyclic ethers.
  • Heterocycles containing nitrogen include, for example azetidine, morpholine, piperidine, piperazine, pyrrolidine, and the like.
  • Other heterocycles include, for example, thiomorpholine, dioxolinyl, and cyclic sulfones.
  • Pharmaceutically acceptable salts of the compounds of formula (I) and (II) include the acid addition and base salts thereof. Suitable acid addition salts are formed from acids which form non-toxic salts. Suitable base salts are formed from bases which form nontoxic salts.
  • the compounds of the invention may also exist in unsolvated and solvated forms.
  • solvate is used herein to describe a molecular complex comprising the compound of the invention and one or more pharmaceutically acceptable solvent molecules, for example, ethanol.
  • polymorph refers to the ability of the compound of the invention to exist in more than one form or crystal structure.
  • the compounds of the present invention may be administered as crystalline or amorphous products. They may be obtained for example as solid plugs, powders, or films by methods such as precipitation, crystallization, freeze drying, spray drying, or evaporative drying. They may be administered alone or in combination with one or more other compounds of the invention or in combination with one or more other drugs. Generally, they will be administered as a formulation in association with one or more pharmaceutically acceptable excipients.
  • excipient is used herein to describe any ingredient other than the compound(s) of the invention. The choice of excipient depends largely on factors such as the particular mode of administration, the effect of the excipient on solubility and stability, and the nature of the dosage form.
  • compositions of the present invention may be formulated into various pharmaceutical forms for administration purposes.
  • compositions there may be cited all compositions usually employed for systemically administering drugs.
  • an effective amount of the particular compound, optionally in addition salt form, as the active ingredient is combined in intimate admixture with a pharmaceutically acceptable carrier, which carrier may take a wide variety of forms depending on the form of preparation desired for administration.
  • a pharmaceutically acceptable carrier which carrier may take a wide variety of forms depending on the form of preparation desired for administration.
  • These pharmaceutical compositions are desirably in unitary dosage form suitable, for example, for oral, rectal, or percutaneous administration.
  • any of the usual pharmaceutical media may be employed such as, for example, water, glycols, oils, alcohols and the like in the case of oral liquid preparations such as suspensions, syrups, elixirs, emulsions, and solutions; or solid carriers such as starches, sugars, kaolin, diluents, lubricants, binders, disintegrating agents and the like in the case of powders, pills, capsules, and tablets. Because of their ease in administration, tablets and capsules represent the most advantageous oral dosage unit forms, in which case solid pharmaceutical carriers are obviously employed. Also included are solid form preparations that can be converted, shortly before use, to liquid forms.
  • the carrier optionally comprises a penetration enhancing agent and/or a suitable wetting agent, optionally combined with suitable additives of any nature in minor proportions, which additives do not introduce a significant deleterious effect on the skin. Said additives may facilitate the administration to the skin and/or may be helpful for preparing the desired compositions.
  • These compositions may be administered in various ways, e.g., as a transdermal patch, as a spot-on, as an ointment.
  • the compounds of the present invention may also be administered via inhalation or insufflation by means of methods and formulations employed in the art for administration via this way.
  • the compounds of the present invention may be administered to the lungs in the form of a solution, a suspension or a dry powder.
  • Unit dosage form refers to physically discrete units suitable as unitary dosages, each unit containing a predetermined quantity of active ingredient calculated to produce the desired therapeutic effect in association with the required pharmaceutical carrier.
  • unit dosage forms are tablets (including scored or coated tablets), capsules, pills, powder packets, wafers, suppositories, injectable solutions or suspensions and the like, and segregated multiples thereof.
  • an effective daily amount would be from 0.01 mg/kg to 50 mg/kg body weight, more preferably from 0.1 mg/kg to 10 mg/kg body weight. It may be appropriate to administer the required dose as two, three, four or more sub-doses at appropriate intervals throughout the day. Said sub-doses may be formulated as unit dosage forms, for example, containing 1 to 1000 mg, and in particular 5 to 200 mg of active ingredient per unit dosage form.
  • the exact dosage and frequency of administration depends on the particular compound of formula (I) used, the particular condition being treated, the severity of the condition being treated, the age, weight and general physical condition of the particular patient as well as other medication the individual may be taking, as is well known to those skilled in the art. Furthermore, it is evident that the effective amount may be lowered or increased depending on the response of the treated subject and/or depending on the evaluation of the physician prescribing the compounds of the instant invention. The effective amount ranges mentioned above are therefore only guidelines and are not intended to limit the scope or use of the invention to any extent.
  • Compounds of type A in scheme 1 can be functionalized with alcohols using Mitsunobu conditions in a polar aprotic solvent, for example THF.
  • a polar aprotic solvent for example THF.
  • the cleavage of the methyl carbamate was performed under basic conditions in 1 ,4-dioxane to form intermediate C.
  • the displacement of the chlorine in C was performed with an alcohol and a base (e.g. NaH) in a polar aprotic solvent (e.g. NMP) to form compounds of the type D.
  • the product was purified via silica gel column chromatography using a dichloromethane-methanol;100-0 to 95-5 gradient. The best fractions were collected and concentrated under reduced pressure. The product was triturated in diisopropylether and the solid was isolated by filtration and dried under vacuum to afford 1 as a white solid. Method 2.
  • HPLC High Performance Liquid Chromatography
  • MS Mass Spectrometer
  • SQL Single Quadrupole Detector
  • MSD Mass Selective Detector
  • RT room temperature
  • BEH bridged ethylsiloxane/silica hybrid
  • DAD Diode Array Detector
  • HSS High Strength silica.
  • Q-Tof Quadrupole Time-of-flight mass spectrometers CLND
  • HEK293 cells transiently transfected with a TLR7 or TLR8 expression vector and NFKB-IUC reporter construct. Briefly, HEK293 cells were grown in culture medium (DMEM supplemented with 10% FCS and 2 mM Glutamine). For transfection of cells in 15 cm dishes, cells were detached with Trypsin-EDTA, transfected with a mix of CMV-TLR7 or TLR8 plasmid (1700 ng), N FKB-IUC plasmid (850 ng) and a transfection reagent and incubated for 48 h at 37°C in a humidified 5% CO2 atmosphere.
  • Transfected cells were then washed in PBS, detached with Trypsin-EDTA and resuspended in medium to a density of 1 .25 x 10 5 cells/mL. Forty microliters of cells were then dispensed into each well in 384-well plates, where 200 nl_ of compound in 100% DMSO was already present. Following 6 hours incubation at 37°C, 5% CO2, the luciferase activity was determined by adding 15 ⁇ _ of Steady Lite Plus substrate (Perkin Elmer) to each well and readout performed on a ViewLux ultraHTS microplate imager (Perkin Elmer). Dose response curves were generated from measurements performed in quadruplicates. Lowest effective concentrations (LEC) values, defined as the concentration that induces an effect which is at least two fold above the standard deviation of the assay, were determined for each compound.
  • LEC Lowest effective concentrations
  • Compound toxicity was determined in parallel using a similar dilution series of compound with 40 ⁇ per well of cells transfected with the CMV-TLR7 construct alone (1 .25 x 10 5 cells/mL), in 384-well plates. Cell viability was measured after 6 hours incubation at 37°C, 5% CO2 by adding 15 ⁇ of ATP lite (Perkin Elmer) per well and reading on a ViewLux ultraHTS microplate imager (Perkin Elmer). Data was reported as
  • the potential of compounds to induce IFN-I was also evaluated by measuring the activation of interferon-stimulated responsive elements (ISRE) by conditioned media from PBMC.
  • ISRE interferon-stimulated responsive elements
  • the ISRE element of sequence GAAACTGAAACT is highly responsive to the STAT1 -STAT2-IRF9 transcription factor, activated upon binding of IFN-I to their receptor IFNAR (Clontech, PT3372-5W).
  • the plasmid pISRE-Luc from Clontech contains 5 copies of this ISRE element, followed by the firefly luciferase ORF.
  • a HEK293 cell line stably transfected with pISRE-Luc (HEK-ISREluc) was established to profile the conditioned PBMC cell culture media.
  • PBMCs were prepared from buffy coats of at least two donors using a standard Ficoll centrifugation protocol. Isolated PBMCs were resuspended in RPMI medium supplemented with 10% human AB serum and 2 x 10 5 cells/well were dispensed into 384-well plates containing compounds (70 ⁇ _ total volume). After overnight incubation, 10 ⁇ _ of supernatant was transferred to 384-well plates containing 5 x 10 3 HEK-ISREluc cells/well in 30 ⁇ _ (plated the day before).
  • Human TLR 7 Human TLR 8 HEK-ISRE luc

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  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/EP2014/063467 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases Ceased WO2014207082A1 (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
AU2014301089A AU2014301089B2 (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
NO14738751A NO3030563T3 (enExample) 2013-06-27 2014-06-26
PL14738751T PL3030563T3 (pl) 2013-06-27 2014-06-26 Pochodne pirolo [3,2-d] pirymidyny do leczenia zakażeń wirusowych i innych chorób
SI201430476T SI3030563T1 (sl) 2013-06-27 2014-06-26 Derivati pirolo (3,2-d) pirimidina za zdravljenje virusnih okužb in drugih bolezni
DK14738751.8T DK3030563T3 (da) 2013-06-27 2014-06-26 Pyrrolo-[3,2-d]-pyrimidin-derivater til behandling af virale infektioner og andre sygdomme
MX2018015053A MX392130B (es) 2013-06-27 2014-06-26 Derivados de pirrolo[3,2-d]pirimidina para el tratamiento de infecciones víricas y otras enfermedades.
KR1020157035575A KR102311234B1 (ko) 2013-06-27 2014-06-26 바이러스 감염 및 기타 질환의 치료를 위한 피롤로[3,2-d]피리미딘 유도체
BR112015032546-7A BR112015032546B1 (pt) 2013-06-27 2014-06-26 Derivados de pirrolo[3,2-d]pirimidina e composição farmacêutica que os compreende para o tratamento de infecções virais e outras doenças
HK16106040.9A HK1218116B (zh) 2013-06-27 2014-06-26 用於治疗病毒感染和其他疾病的吡咯并[3，2-d]嘧啶衍生物
JP2016522487A JP6763769B2 (ja) 2013-06-27 2014-06-26 ウイルス感染症および他の疾病の処置のためのピロロ［３，２−ｄ］ピリミジン誘導体
HRP20171720TT HRP20171720T1 (hr) 2013-06-27 2014-06-26 Derivati pirolo [3,2-d] pirimidina za liječenje virusnih infekcija i drugih bolesti
EP14738751.8A EP3030563B1 (en) 2013-06-27 2014-06-26 Pyrrolo [3,2-d] pyrimidine derivatives for the treatment of viral infections and other diseases
UAA201600620A UA117590C2 (uk) 2013-06-27 2014-06-26 ПОХІДНІ ПІРОЛО[3,2-d]ПІРИМІДИНУ ДЛЯ ЛІКУВАННЯ ВІРУСНИХ ІНФЕКЦІЙ ТА ІНШИХ ЗАХВОРЮВАНЬ
SG11201510637UA SG11201510637UA (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
MX2015017671A MX361527B (es) 2013-06-27 2014-06-26 Derivados de pirrolo[3,2-d]pirimidina para el tratamiento de infecciones víricas y otras enfermedades.
CA2913028A CA2913028C (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
NZ714267A NZ714267B2 (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
ES14738751.8T ES2645950T3 (es) 2013-06-27 2014-06-26 Derivados de pirrolo[3,2-d]pirimidina para el tratamiento de infecciones víricas y otras enfermedades
EA201690093A EA034893B1 (ru) 2013-06-27 2014-06-26 Производные пирроло[3,2-d]пиримидина для лечения вирусных инфекций и других заболеваний
US14/392,214 US10385054B2 (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
CN201480036233.5A CN105473592B (zh) 2013-06-27 2014-06-26 用于治疗病毒感染和其他疾病的吡咯并[3,2-d]嘧啶衍生物
IL242655A IL242655B (en) 2013-06-27 2015-11-18 A history of pyrrolo(3,2–d)pyrimidine for the treatment of viral infections and other diseases
PH12015502780A PH12015502780B1 (en) 2013-06-27 2015-12-14 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
IL258253A IL258253B (en) 2013-06-27 2018-03-20 History of pyrrolo(2,3–d)pyrimidine for the treatment of viral infections and other diseases
AU2018274911A AU2018274911B2 (en) 2013-06-27 2018-12-05 Pyrrolo[3,2-c]Pyrimidine derivatives for the treatment of viral infections and other diseases
IL264402A IL264402B (en) 2013-06-27 2019-01-22 History of pyrrolo(2,3–d)pyrimidine for the treatment of viral infections and other diseases
US16/441,213 US10781216B2 (en) 2013-06-27 2019-06-14 Pyrrolo [3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13174108 2013-06-27
EP13174108.4 2013-06-27

Related Child Applications (2)

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US14/392,214 A-371-Of-International US10385054B2 (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases
US16/441,213 Continuation US10781216B2 (en) 2013-06-27 2019-06-14 Pyrrolo [3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases

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WO2014207082A1 true WO2014207082A1 (en) 2014-12-31

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PCT/EP2014/063467 Ceased WO2014207082A1 (en) 2013-06-27 2014-06-26 Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases

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US (2) US10385054B2 (enExample)
EP (1) EP3030563B1 (enExample)
JP (2) JP6763769B2 (enExample)
KR (1) KR102311234B1 (enExample)
CN (2) CN105473592B (enExample)
AU (2) AU2014301089B2 (enExample)
BR (1) BR112015032546B1 (enExample)
CA (1) CA2913028C (enExample)
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DK (1) DK3030563T3 (enExample)
EA (2) EA202090258A3 (enExample)
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HR (1) HRP20171720T1 (enExample)
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IL (3) IL242655B (enExample)
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