AU2008286325A1 - Preparation of a compound for the treatment of Duchenne muscular dystrophy - Google Patents
Preparation of a compound for the treatment of Duchenne muscular dystrophy Download PDFInfo
- Publication number
- AU2008286325A1 AU2008286325A1 AU2008286325A AU2008286325A AU2008286325A1 AU 2008286325 A1 AU2008286325 A1 AU 2008286325A1 AU 2008286325 A AU2008286325 A AU 2008286325A AU 2008286325 A AU2008286325 A AU 2008286325A AU 2008286325 A1 AU2008286325 A1 AU 2008286325A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- process according
- solvent
- muscular dystrophy
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 6
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 title description 17
- 238000000034 method Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- 239000008096 xylene Substances 0.000 claims description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003738 xylenes Chemical group 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 102000011856 Utrophin Human genes 0.000 description 19
- 108010075653 Utrophin Proteins 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 210000003205 muscle Anatomy 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000002560 therapeutic procedure Methods 0.000 description 9
- 108010069091 Dystrophin Proteins 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 102000001039 Dystrophin Human genes 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 230000003827 upregulation Effects 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- 108060001084 Luciferase Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 201000006938 muscular dystrophy Diseases 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- -1 4-Me-2-pentanone Chemical compound 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 238000003468 luciferase reporter gene assay Methods 0.000 description 3
- 210000003098 myoblast Anatomy 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- UPJVUFCLBYQKFH-UHFFFAOYSA-N 2-amino-4-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(O)C(N)=C1 UPJVUFCLBYQKFH-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KSGCNXAZROJSNW-UHFFFAOYSA-N 5-ethylsulfonyl-2-naphthalen-2-yl-1,3-benzoxazole Chemical compound C1=CC=CC2=CC(C=3OC4=CC=C(C=C4N=3)S(=O)(=O)CC)=CC=C21 KSGCNXAZROJSNW-UHFFFAOYSA-N 0.000 description 2
- 230000035495 ADMET Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 108010069440 Dystrophin-Associated Protein Complex Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010535 acyclic diene metathesis reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 230000004094 calcium homeostasis Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 101150015424 dmd gene Proteins 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000037433 frameshift Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OZOMQRBLCMDCEG-CHHVJCJISA-N 1-[(z)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N/N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-CHHVJCJISA-N 0.000 description 1
- 201000006935 Becker muscular dystrophy Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108700024394 Exon Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 208000035969 Genetic neuromuscular disease Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 238000003120 Steady-Glo Luciferase Assay System Methods 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 210000001766 X chromosome Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000013216 cat model Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 238000002659 cell therapy Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 210000003837 chick embryo Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 1
- 229960001117 clenbuterol Drugs 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 229960001987 dantrolene Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000011833 dog model Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 238000010448 genetic screening Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000003364 immunohistochemistry Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 238000002961 luciferase induction Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000011422 pharmacological therapy Methods 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 208000022587 qualitative or quantitative defects of dystrophin Diseases 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000000518 sarcolemma Anatomy 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000010473 stable expression Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000013603 viral vector Substances 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0715937.9 | 2007-08-15 | ||
| GBGB0715937.9A GB0715937D0 (en) | 2007-08-15 | 2007-08-15 | Method of treatment og duchenne muscular dystrophy |
| PCT/EP2008/006719 WO2009021749A2 (en) | 2007-08-15 | 2008-08-14 | Preparation of a compound for the treatment of duchenne muscular dystrophy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008286325A1 true AU2008286325A1 (en) | 2009-02-19 |
Family
ID=38566447
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008286325A Abandoned AU2008286325A1 (en) | 2007-08-15 | 2008-08-14 | Preparation of a compound for the treatment of Duchenne muscular dystrophy |
| AU2008286324A Abandoned AU2008286324A1 (en) | 2007-08-15 | 2008-08-14 | Polymorphs of a compound for the treatment of Duchenne muscular dystrophy |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008286324A Abandoned AU2008286324A1 (en) | 2007-08-15 | 2008-08-14 | Polymorphs of a compound for the treatment of Duchenne muscular dystrophy |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US8138351B2 (https=) |
| EP (2) | EP2176246A2 (https=) |
| JP (2) | JP2010535830A (https=) |
| KR (1) | KR20100075777A (https=) |
| CN (2) | CN101679323A (https=) |
| AR (1) | AR068810A1 (https=) |
| AU (2) | AU2008286325A1 (https=) |
| BR (2) | BRPI0811315A2 (https=) |
| CA (2) | CA2685590A1 (https=) |
| CL (1) | CL2008002391A1 (https=) |
| GB (1) | GB0715937D0 (https=) |
| IL (1) | IL201908A0 (https=) |
| MX (2) | MX2009011967A (https=) |
| PE (1) | PE20090604A1 (https=) |
| RU (1) | RU2009141831A (https=) |
| TW (1) | TW200911767A (https=) |
| WO (2) | WO2009021749A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2641880C (en) * | 2006-02-10 | 2014-09-09 | Summit Corporation Plc | Treatment of duchenne muscular dystrophy |
| GB201208178D0 (en) | 2012-05-10 | 2012-06-20 | Summit Corp Plc | Pharmaceutical composition for the treatment of duchenne muscular dystrophy |
| GB201412010D0 (en) | 2014-07-04 | 2014-08-20 | Summit Corp Plc | Treatment of hypertransaminasemia |
| EP3500245A1 (en) | 2016-03-30 | 2019-06-26 | Summit (Oxford) Limited | Composition for the treatment of duchenne muscular dystrophy |
| WO2017175842A1 (ja) * | 2016-04-07 | 2017-10-12 | 国立大学法人京都大学 | スプライシングの改変に関する化合物及び医薬組成物 |
| KR102019048B1 (ko) | 2017-02-06 | 2019-09-09 | 가톨릭대학교 산학협력단 | MG53과 Orai1의 결합을 이용한 근육긴장저하 치료제 스크리닝 방법 |
| KR101886788B1 (ko) | 2017-02-07 | 2018-08-09 | 가톨릭대학교 산학협력단 | MG53과 Orai1의 결합을 이용한 뒤시엔느 골격근 위축증 치료제 스크리닝 방법 |
| WO2018236879A1 (en) | 2017-06-19 | 2018-12-27 | University Of Maryland, Baltimore | Microtubule polymerization inhibitor prodrugs and methods of using the same |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3993659A (en) * | 1971-08-10 | 1976-11-23 | Ciba-Geigy Corporation | Bis-benzoxazolyl-naphthalenes as optical brighteners |
| CH617809GA3 (https=) * | 1975-10-10 | 1980-06-30 | ||
| US4110246A (en) * | 1976-05-13 | 1978-08-29 | Hoechst Aktiengesellschaft | Mixture of benzoxazole derivatives |
| DE3027479A1 (de) * | 1980-07-19 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | Mischungen von optischen aufhellern und deren verwendung |
| JPS615071A (ja) * | 1984-06-15 | 1986-01-10 | Fuji Photo Film Co Ltd | ベンゾオキサゾ−ル誘導体 |
| DE3617451A1 (de) * | 1986-05-23 | 1987-11-26 | Hoechst Ag | Sulfonat- oder sulfonamidgruppen-haltige bis-benzoxazolylnaphthaline, verfahren zu deren herstellung und deren verwendung |
| DE3819051A1 (de) * | 1988-06-04 | 1989-12-07 | Agfa Gevaert Ag | Farbfotografisches aufzeichnungsmaterial |
| EP0527704B1 (de) * | 1991-08-08 | 1996-08-28 | Ciba-Geigy Ag | Farbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| ES2157268T5 (es) * | 1994-02-24 | 2004-12-01 | SYMRISE GMBH & CO KG | Preparados cosmeticos y dermatologicos que contienen acidos fenilen-1,4-bisbencimidazolsulfonicos. |
| US6004719A (en) * | 1994-04-25 | 1999-12-21 | Polaroid Corporation | Imaging medium and process for producing an image |
| CA2192188C (en) * | 1994-06-30 | 2008-08-19 | Joel D. Oxman | Cure-indicating molding and coating composition |
| US5596025A (en) * | 1994-06-30 | 1997-01-21 | Minnesota Mining And Manufacturing Company | Dental impression material with cure-indicating dye |
| US5567843A (en) * | 1995-03-20 | 1996-10-22 | The Dow Chemical Company | Process for making 2-aryl benz (ox, thi, imid)azoles and 2-aminoaryl aminobenz(ox, thi, imid)azoles |
| US6222044B1 (en) * | 1995-03-20 | 2001-04-24 | The Dow Chemical Company | Process for making 2-aryl benz (ox, thi, imid) azoles and 2-aminoaryl aminobenz (ox, thi, imid) azoles |
| US5977101A (en) * | 1995-06-29 | 1999-11-02 | Smithkline Beecham Corporation | Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity |
| US5645948A (en) * | 1996-08-20 | 1997-07-08 | Eastman Kodak Company | Blue organic electroluminescent devices |
| US6110638A (en) * | 1996-11-27 | 2000-08-29 | Polaroid Corporation | Process and composition for generation of acid |
| US5914213A (en) * | 1996-11-27 | 1999-06-22 | Polaroid Corporation | Process and composition for generation of acid |
| US6177572B1 (en) * | 1997-08-20 | 2001-01-23 | Sepracor, Inc. | Solid and liquid-phase synthesis of benzoxazoles and benzothiazoles and their use |
| US6312822B1 (en) * | 1998-05-28 | 2001-11-06 | Eastman Chem Co | Dispersion aids for optical brighteners in polyolefins |
| GB9815880D0 (en) * | 1998-07-21 | 1998-09-16 | Pfizer Ltd | Heterocycles |
| US6436558B1 (en) * | 1998-08-07 | 2002-08-20 | Fuji Photo Film Co., Ltd. | Organic electroluminescence element |
| FR2789581B1 (fr) * | 1999-02-12 | 2001-05-04 | Oreal | Compositions photoprotectrices contenant un derive de benzotriazole, un derive de bis-resorcinyl triazine et un compose a groupements benzoazolyle ou benzodiazolyle |
| FR2789582B1 (fr) * | 1999-02-12 | 2001-05-04 | Oreal | Compositions photoprotectrices contenant un derive de bis-resorcinyl triazine et un compose a groupements benzoazolyle ou benzodiazolyle |
| DE50003732D1 (de) * | 1999-05-07 | 2003-10-23 | Basf Ag | 4-(3',4'-heterocyclylbenzoyl)pyrazole als herbizide |
| EP1177179A1 (de) * | 1999-05-07 | 2002-02-06 | Basf Aktiengesellschaft | Benzoheterocyclylcyclohexenone und ihre verwendung als herbizide |
| FR2794645B1 (fr) * | 1999-06-08 | 2001-08-10 | Oreal | Compositions photoprotectrices contenant un compose hydrocarbone bis-hydroxyphenylbenzotriazole et un compose a groupements benzoazolyle ou benzodiazolyle |
| AU7320100A (en) * | 1999-09-24 | 2001-04-24 | Ono Pharmaceutical Co. Ltd. | Hydroxamic acid derivatives, process for the production thereof and drugs containing the same as the active ingredient |
| US6565987B2 (en) * | 1999-11-12 | 2003-05-20 | Eastman Chemical Company | Non-exuding optically brightened polyolefin blends |
| US6716413B1 (en) * | 2000-10-16 | 2004-04-06 | Mallinckrodt, Inc. | Indole compounds as tissue-specific exogenous optical agents |
| EP1889891B1 (en) * | 2000-11-30 | 2017-11-22 | Canon Kabushiki Kaisha | Luminescence device and display apparatus |
| US20050113283A1 (en) * | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| US20050261298A1 (en) * | 2002-01-18 | 2005-11-24 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| DK1482931T3 (da) * | 2002-03-05 | 2011-12-19 | Transtech Pharma Inc | Mono- og bicycliske azolderivater der inhiberer interaktionen af ligander med RAGE |
| EP1547996A4 (en) * | 2002-08-30 | 2006-08-02 | Bf Res Inst Inc | DIAGNOSTIC PROBES AND REMEDIES FOR DISEASES IN WHICH PRION PROTEIN IS ACCUMULATED, AND ANIMAL FEVERING FOR PRION PROTEIN |
| WO2004103960A2 (en) * | 2003-05-16 | 2004-12-02 | Ambit Biosciences Corporation | Compounds and uses thereof |
| WO2005000295A1 (en) * | 2003-05-20 | 2005-01-06 | Transtech Pharma, Inc. | Rage antagonists as agents to reverse amyloidosis and diseases associated therewith |
| WO2005023761A2 (en) * | 2003-09-11 | 2005-03-17 | Kemia, Inc. | Cytokine inhibitors |
| CN1882879B (zh) * | 2003-09-22 | 2010-08-11 | 爱克发印艺公司 | 可光聚合的组合物 |
| US7097888B2 (en) * | 2003-12-15 | 2006-08-29 | Eastman Kodak Company | Aligned liquid crystal layer containing azolium salts and process for increasing the tilt |
| US7592373B2 (en) * | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| CA2555313A1 (en) * | 2004-02-06 | 2005-08-18 | Insight Biopharmaceuticals Ltd | Heparanase inhibitors and uses thereof |
| MY144903A (en) * | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
| EP1794255B1 (en) * | 2004-08-19 | 2016-11-16 | LG Chem, Ltd. | Organic light-emitting device comprising buffer layer and method for fabricating the same |
| US7723340B2 (en) * | 2005-01-13 | 2010-05-25 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
| US20060223849A1 (en) * | 2005-03-14 | 2006-10-05 | Mjalli Adnan M | Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors |
| JP2007086165A (ja) * | 2005-09-20 | 2007-04-05 | Fujifilm Corp | 感光性組成物、これを用いた平版印刷版原版及び画像記録方法 |
| KR101408026B1 (ko) * | 2005-12-02 | 2014-06-20 | 사켐,인코포레이티드 | 음이온-교환 치환 크로마토그래피 공정 및 음이온-교환치환 크로마토그래피 공정에서 디스플레이서 화합물들로서사용하기 위한 음이온성 유기 화합물들 |
| KR101213485B1 (ko) * | 2006-01-27 | 2012-12-18 | 삼성디스플레이 주식회사 | 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 |
| KR101213486B1 (ko) * | 2006-02-02 | 2012-12-20 | 삼성디스플레이 주식회사 | 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 |
| CA2641880C (en) * | 2006-02-10 | 2014-09-09 | Summit Corporation Plc | Treatment of duchenne muscular dystrophy |
| KR101325062B1 (ko) * | 2006-05-19 | 2013-11-05 | 삼성디스플레이 주식회사 | 발광 이종 핵 구리-이리듐 착체 및 이를 이용한 유기 전계발광 소자 |
-
2007
- 2007-08-15 GB GBGB0715937.9A patent/GB0715937D0/en not_active Ceased
-
2008
- 2008-08-14 AR ARP080103560A patent/AR068810A1/es not_active Application Discontinuation
- 2008-08-14 AU AU2008286325A patent/AU2008286325A1/en not_active Abandoned
- 2008-08-14 PE PE2008001385A patent/PE20090604A1/es not_active Application Discontinuation
- 2008-08-14 CN CN200880015864A patent/CN101679323A/zh active Pending
- 2008-08-14 KR KR1020097023605A patent/KR20100075777A/ko not_active Withdrawn
- 2008-08-14 TW TW097131010A patent/TW200911767A/zh unknown
- 2008-08-14 WO PCT/EP2008/006719 patent/WO2009021749A2/en not_active Ceased
- 2008-08-14 EP EP08785565A patent/EP2176246A2/en not_active Withdrawn
- 2008-08-14 AU AU2008286324A patent/AU2008286324A1/en not_active Abandoned
- 2008-08-14 US US12/599,970 patent/US8138351B2/en not_active Expired - Fee Related
- 2008-08-14 WO PCT/EP2008/006718 patent/WO2009021748A2/en not_active Ceased
- 2008-08-14 EP EP08785566A patent/EP2188270A2/en not_active Withdrawn
- 2008-08-14 CA CA002685590A patent/CA2685590A1/en not_active Abandoned
- 2008-08-14 CL CL2008002391A patent/CL2008002391A1/es unknown
- 2008-08-14 US US12/192,053 patent/US20090048314A1/en not_active Abandoned
- 2008-08-14 MX MX2009011967A patent/MX2009011967A/es not_active Application Discontinuation
- 2008-08-14 JP JP2010520499A patent/JP2010535830A/ja active Pending
- 2008-08-14 CN CN2008800158003A patent/CN101896475A/zh active Pending
- 2008-08-14 MX MX2009011916A patent/MX2009011916A/es not_active Application Discontinuation
- 2008-08-14 BR BRPI0811315-7A2A patent/BRPI0811315A2/pt not_active Application Discontinuation
- 2008-08-14 CA CA002685939A patent/CA2685939A1/en not_active Abandoned
- 2008-08-14 BR BRPI0811548-6A2A patent/BRPI0811548A2/pt not_active Application Discontinuation
- 2008-08-14 JP JP2010520498A patent/JP2010535829A/ja active Pending
- 2008-08-14 RU RU2009141831/04A patent/RU2009141831A/ru not_active Application Discontinuation
-
2009
- 2009-11-03 IL IL201908A patent/IL201908A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2685939A1 (en) | 2009-02-19 |
| WO2009021748A3 (en) | 2009-04-02 |
| TW200911767A (en) | 2009-03-16 |
| US20090048314A1 (en) | 2009-02-19 |
| IL201908A0 (en) | 2010-06-16 |
| JP2010535829A (ja) | 2010-11-25 |
| EP2188270A2 (en) | 2010-05-26 |
| AR068810A1 (es) | 2009-12-09 |
| WO2009021749A3 (en) | 2009-04-02 |
| EP2176246A2 (en) | 2010-04-21 |
| PE20090604A1 (es) | 2009-05-16 |
| MX2009011916A (es) | 2009-11-18 |
| MX2009011967A (es) | 2009-11-19 |
| WO2009021748A2 (en) | 2009-02-19 |
| CA2685590A1 (en) | 2009-02-19 |
| WO2009021749A8 (en) | 2009-09-11 |
| CL2008002391A1 (es) | 2009-05-22 |
| AU2008286324A1 (en) | 2009-02-19 |
| GB0715937D0 (en) | 2007-09-26 |
| KR20100075777A (ko) | 2010-07-05 |
| RU2009141831A (ru) | 2011-05-20 |
| JP2010535830A (ja) | 2010-11-25 |
| US8138351B2 (en) | 2012-03-20 |
| US20100267961A1 (en) | 2010-10-21 |
| BRPI0811548A2 (pt) | 2014-11-18 |
| CN101896475A (zh) | 2010-11-24 |
| WO2009021749A2 (en) | 2009-02-19 |
| CN101679323A (zh) | 2010-03-24 |
| BRPI0811315A2 (pt) | 2015-01-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8138351B2 (en) | Treatment of duchenne muscular dystrophy | |
| US20120149741A1 (en) | Treatment of duchenne muscular dystrophy | |
| EP2170396B1 (en) | Drug combinations for the treatment of duchenne muscular dystrophy | |
| WO2008029168A2 (en) | Treatment of duchenne muscular dystrophy | |
| CA2831342C (en) | Medicament for liver regeneration and for treatment of liver failure | |
| JP5376956B2 (ja) | デュシェンヌ型筋ジストロフィーの治療 | |
| US20100048660A1 (en) | Treatment of duchenne muscular dystrophy | |
| CN114502541B (zh) | 诱导抗老化基因klotho的表达的化合物及其用途 | |
| KR102792113B1 (ko) | Stat3 억제제 | |
| WO2008029152A2 (en) | Treatment of duchenne muscular dystrophy | |
| CA2843853A1 (en) | Macrocyclic insulin-degrading enzyme (ide) inhibitors and uses thereof | |
| Li et al. | Drug discovery against psoriasis: identification of a new potent FMS-like tyrosine kinase 3 (FLT3) inhibitor, 1-(4-((1 H-Pyrazolo [3, 4-d] pyrimidin-4-yl) oxy)-3-fluorophenyl)-3-(5-(tert-butyl) isoxazol-3-yl) urea, that showed potent activity in a psoriatic animal model | |
| EP4129297A1 (en) | Treatment of cognitive and mood symptoms in neurodegenerative and neuropsychiatric disorders with alpha5-containing gabaa receptor agonists | |
| EP1656360B1 (en) | Thiazoline derivatives as selective androgen receptor modulators (sarms) | |
| CN117384158A (zh) | 一种Wnt通路抑制剂化合物 | |
| US20230145868A1 (en) | Urea inhibitors of micro-rna | |
| WO2025229046A1 (en) | Substituted hydroquinolines for the treatment of glioblastoma multiforme | |
| CA2685599A1 (en) | Compounds for treating duchenne muscular dystrophy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BIOMARIN IGA LIMITED Free format text: FORMER APPLICANT(S): SUMMIT CORPORATION PLC |
|
| TH | Corrigenda |
Free format text: IN VOL 24, NO 10, PAGE(S) 1085 UNDER THE HEADING ASSIGNMENTS BEFORE GRANT, SECTION 113 - 2008 UNDERTHE NAME BIOMARIN IGA LIMITED, APPLICATION NO. 2008286325, UNDER INID(71), CORRECT THE APPLICANT NAME TO BIOMARIN IGA LIMITED |
|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |