JPWO2019220147A5 - - Google Patents
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- JPWO2019220147A5 JPWO2019220147A5 JP2020564577A JP2020564577A JPWO2019220147A5 JP WO2019220147 A5 JPWO2019220147 A5 JP WO2019220147A5 JP 2020564577 A JP2020564577 A JP 2020564577A JP 2020564577 A JP2020564577 A JP 2020564577A JP WO2019220147 A5 JPWO2019220147 A5 JP WO2019220147A5
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- Japan
- Prior art keywords
- general formula
- compound
- formula
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 17
- -1 4- {bis [(2S, 3R, 4R, 5R) -2, 3,4,5,6-pentahydroxyhexyl] amino} piperidine-1-carbonyl Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 10
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 10
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 10
- 229960002714 fluticasone Drugs 0.000 claims description 10
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 10
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 claims description 10
- 229960002657 orciprenaline Drugs 0.000 claims description 10
- 229960002052 salbutamol Drugs 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000001575 pathological effect Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 5
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 5
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 5
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 5
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims description 5
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims description 5
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 5
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 5
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 5
- 229940125715 antihistaminic agent Drugs 0.000 claims description 5
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims description 5
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 5
- 229960004436 budesonide Drugs 0.000 claims description 5
- 229960001803 cetirizine Drugs 0.000 claims description 5
- 229960003291 chlorphenamine Drugs 0.000 claims description 5
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003246 corticosteroid Substances 0.000 claims description 5
- 229960001334 corticosteroids Drugs 0.000 claims description 5
- 229960001271 desloratadine Drugs 0.000 claims description 5
- 229960000533 dornase alfa Drugs 0.000 claims description 5
- 108010067396 dornase alfa Proteins 0.000 claims description 5
- 229960003592 fexofenadine Drugs 0.000 claims description 5
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 5
- 229960000289 fluticasone propionate Drugs 0.000 claims description 5
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 5
- 229960002848 formoterol Drugs 0.000 claims description 5
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 5
- 229960001317 isoprenaline Drugs 0.000 claims description 5
- 229940039009 isoproterenol Drugs 0.000 claims description 5
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 5
- 229960003088 loratadine Drugs 0.000 claims description 5
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 5
- 229960005127 montelukast Drugs 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229960005414 pirbuterol Drugs 0.000 claims description 5
- 229960005205 prednisolone Drugs 0.000 claims description 5
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 5
- 229960004618 prednisone Drugs 0.000 claims description 5
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 5
- 229940044601 receptor agonist Drugs 0.000 claims description 5
- 239000000018 receptor agonist Substances 0.000 claims description 5
- 229960004017 salmeterol Drugs 0.000 claims description 5
- 229960000195 terbutaline Drugs 0.000 claims description 5
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 5
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 5
- 229960004764 zafirlukast Drugs 0.000 claims description 5
- 102000003787 Anoctamin-1 Human genes 0.000 claims description 4
- 108090000160 Anoctamin-1 Proteins 0.000 claims description 4
- IGHAUPGDVQMLLE-UHFFFAOYSA-N CC1=NNC2=NC(N)=C(NC=O)N=C12 Chemical compound CC1=NNC2=NC(N)=C(NC=O)N=C12 IGHAUPGDVQMLLE-UHFFFAOYSA-N 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
- VGTAFMLWDKAJLP-UHFFFAOYSA-N NC1=C(NC=O)N=C(C=NN2)C2=N1 Chemical compound NC1=C(NC=O)N=C(C=NN2)C2=N1 VGTAFMLWDKAJLP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 201000009267 bronchiectasis Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003623 enhancer Substances 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006268 reductive amination reaction Methods 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 3
- 230000000241 respiratory effect Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 2
- 206010014561 Emphysema Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 206010021198 ichthyosis Diseases 0.000 claims description 2
- 230000000155 isotopic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- 239000003396 histamine H4 receptor antagonist Substances 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- 229940044551 receptor antagonist Drugs 0.000 description 6
- 239000002464 receptor antagonist Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 description 3
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 3
- 229960004574 azelastine Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229960000676 flunisolide Drugs 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 229960001508 levocetirizine Drugs 0.000 description 3
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1808093.7A GB201808093D0 (en) | 2018-05-18 | 2018-05-18 | Compounds |
| GB1808093.7 | 2018-05-18 | ||
| PCT/GB2019/051383 WO2019220147A1 (en) | 2018-05-18 | 2019-05-17 | Compounds |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021524453A JP2021524453A (ja) | 2021-09-13 |
| JP2021524453A5 JP2021524453A5 (https=) | 2022-05-09 |
| JPWO2019220147A5 true JPWO2019220147A5 (https=) | 2022-05-09 |
| JP7333793B2 JP7333793B2 (ja) | 2023-08-25 |
Family
ID=62723333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020564577A Active JP7333793B2 (ja) | 2018-05-18 | 2019-05-17 | 化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US12037336B2 (https=) |
| EP (1) | EP3794002B1 (https=) |
| JP (1) | JP7333793B2 (https=) |
| GB (1) | GB201808093D0 (https=) |
| WO (1) | WO2019220147A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201908453D0 (en) | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
| PH12021553110A1 (en) | 2019-06-12 | 2022-08-01 | Tmem16A Ltd | Compounds for treating respiratory disease |
| EP4259607A1 (en) | 2020-12-11 | 2023-10-18 | Tmem16A Limited | Benzimidazole derivatives for treating respiratory disease |
| US12414916B2 (en) | 2021-06-10 | 2025-09-16 | Belhaven BioPharma Inc. | Dry powder formulations of epinephrine and associated methods |
| US11932648B2 (en) | 2021-06-28 | 2024-03-19 | Blueprint Medicines Corporation | CDK2 inhibitors |
| CN117946013B (zh) * | 2024-01-25 | 2024-07-02 | 白银康寓信生物科技有限公司 | 一锅法合成5,6-二卤代-3-氨基吡嗪-2-甲酸甲酯的方法 |
| US20260108686A1 (en) | 2024-10-21 | 2026-04-23 | Belhaven BioPharma Inc. | Compositions, devices, and methods for intranasal delivery of dry powder epinephrine |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858614B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenolic guanidine sodium channel blockers |
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US6903105B2 (en) | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| ES2432529T3 (es) | 2003-08-18 | 2013-12-04 | Parion Sciences, Inc. | Bloqueadores del canal de sodio de pirazinoilguanidina rematada |
| US7375107B2 (en) | 2003-08-18 | 2008-05-20 | Parion Sciences, Inc. | Alaphatic pyrazinoylguanidine sodium channel blockers |
| JP2007502829A (ja) | 2003-08-18 | 2007-02-15 | パリオン・サイエンシィズ・インコーポレーテッド | 環状ピラジノイルグアニジンナトリウムチャネルブロッカー |
| US20050090505A1 (en) | 2003-08-18 | 2005-04-28 | Johnson Michael R. | Methods of reducing risk of infection from pathogens |
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| GB201619694D0 (en) * | 2016-11-22 | 2017-01-04 | Entpr Therapeutics Ltd | Compounds |
-
2018
- 2018-05-18 GB GBGB1808093.7A patent/GB201808093D0/en not_active Ceased
-
2019
- 2019-05-17 WO PCT/GB2019/051383 patent/WO2019220147A1/en not_active Ceased
- 2019-05-17 EP EP19726121.7A patent/EP3794002B1/en active Active
- 2019-05-17 JP JP2020564577A patent/JP7333793B2/ja active Active
- 2019-05-17 US US17/056,370 patent/US12037336B2/en active Active
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