JP2019535747A5 - - Google Patents
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- Publication number
- JP2019535747A5 JP2019535747A5 JP2019527365A JP2019527365A JP2019535747A5 JP 2019535747 A5 JP2019535747 A5 JP 2019535747A5 JP 2019527365 A JP2019527365 A JP 2019527365A JP 2019527365 A JP2019527365 A JP 2019527365A JP 2019535747 A5 JP2019535747 A5 JP 2019535747A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- formamide
- pyrrolo
- pyrazine
- 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.)
- Granted
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 139
- RGMLCTHZPQDGJD-UHFFFAOYSA-N NC1=C(NC=O)N=C(C=CN2)C2=N1 Chemical compound NC1=C(NC=O)N=C(C=CN2)C2=N1 RGMLCTHZPQDGJD-UHFFFAOYSA-N 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- -1 2-methoxy-2-oxoethyl Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- JAFCYNLNCWHKOW-UHFFFAOYSA-N NC1=C(NC=O)N=C(C(Cl)=CN2)C2=N1 Chemical compound NC1=C(NC=O)N=C(C(Cl)=CN2)C2=N1 JAFCYNLNCWHKOW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- DCJCUIBKYBYGAF-UHFFFAOYSA-N NC1=C(NC=O)N=C(C(Br)=CN2)C2=N1 Chemical compound NC1=C(NC=O)N=C(C(Br)=CN2)C2=N1 DCJCUIBKYBYGAF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- KZBURGSNUWTOIZ-UHFFFAOYSA-N C1=C(C2=C(N1)N=C(C(=N2)NC=O)N)C#N Chemical compound C1=C(C2=C(N1)N=C(C(=N2)NC=O)N)C#N KZBURGSNUWTOIZ-UHFFFAOYSA-N 0.000 claims description 2
- IQVDGIHFADVNTI-UHFFFAOYSA-N CC1=CC2=C(N1)N=C(C(=N2)NC=O)N Chemical compound CC1=CC2=C(N1)N=C(C(=N2)NC=O)N IQVDGIHFADVNTI-UHFFFAOYSA-N 0.000 claims description 2
- YKCDWPWVJGHZQN-UHFFFAOYSA-N CC1=CNC2=C1N=C(C(=N2)N)NC=O Chemical compound CC1=CNC2=C1N=C(C(=N2)N)NC=O YKCDWPWVJGHZQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims 4
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229960002052 salbutamol Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 239000013543 active substance Substances 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 2
- 102000003787 Anoctamin-1 Human genes 0.000 claims 2
- 108090000160 Anoctamin-1 Proteins 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- 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 2
- 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 2
- 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 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 229940125715 antihistaminic agent Drugs 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 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 2
- 229960004574 azelastine Drugs 0.000 claims 2
- 229950000210 beclometasone dipropionate Drugs 0.000 claims 2
- 201000009267 bronchiectasis Diseases 0.000 claims 2
- 229960004436 budesonide Drugs 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229960001803 cetirizine Drugs 0.000 claims 2
- 229960003291 chlorphenamine Drugs 0.000 claims 2
- 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 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- 229960001334 corticosteroids Drugs 0.000 claims 2
- 229960001271 desloratadine Drugs 0.000 claims 2
- 229960000533 dornase alfa Drugs 0.000 claims 2
- 108010067396 dornase alfa Proteins 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 2
- 229960003592 fexofenadine Drugs 0.000 claims 2
- 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 2
- 229960000676 flunisolide Drugs 0.000 claims 2
- 229960001469 fluticasone furoate Drugs 0.000 claims 2
- XTULMSXFIHGYFS-VLSRWLAYSA-N fluticasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4[C@@H](F)C[C@H]3[C@@H]2C[C@H]1C)C(=O)SCF)C(=O)C1=CC=CO1 XTULMSXFIHGYFS-VLSRWLAYSA-N 0.000 claims 2
- 229960000289 fluticasone propionate Drugs 0.000 claims 2
- 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 2
- 229960002848 formoterol Drugs 0.000 claims 2
- 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 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- 229960004078 indacaterol Drugs 0.000 claims 2
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 claims 2
- 229960001317 isoprenaline Drugs 0.000 claims 2
- 229940039009 isoproterenol Drugs 0.000 claims 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 2
- 229960003088 loratadine Drugs 0.000 claims 2
- 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 2
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229960002744 mometasone furoate Drugs 0.000 claims 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims 2
- 229960005127 montelukast Drugs 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229960002657 orciprenaline Drugs 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229960005205 prednisolone Drugs 0.000 claims 2
- 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 2
- 229960004618 prednisone Drugs 0.000 claims 2
- 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 2
- 230000002265 prevention Effects 0.000 claims 2
- 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 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 238000006268 reductive amination reaction Methods 0.000 claims 2
- 229960004017 salmeterol Drugs 0.000 claims 2
- 229960000195 terbutaline Drugs 0.000 claims 2
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 2
- 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 2
- 229960004764 zafirlukast Drugs 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 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 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 206010021198 ichthyosis Diseases 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 102000016397 Methyltransferase Human genes 0.000 description 2
- 108060004795 Methyltransferase Proteins 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1619694.1A GB201619694D0 (en) | 2016-11-22 | 2016-11-22 | Compounds |
| GB1619694.1 | 2016-11-22 | ||
| PCT/GB2017/053499 WO2018096325A1 (en) | 2016-11-22 | 2017-11-22 | Benzodiazolium compounds as enac inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019535747A JP2019535747A (ja) | 2019-12-12 |
| JP2019535747A5 true JP2019535747A5 (https=) | 2021-05-06 |
| JP6980014B2 JP6980014B2 (ja) | 2021-12-15 |
Family
ID=57993838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019527365A Active JP6980014B2 (ja) | 2016-11-22 | 2017-11-22 | ＥＮａＣ阻害剤としてのベンゾジアゾリウム化合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US10941149B2 (https=) |
| EP (1) | EP3544981B1 (https=) |
| JP (1) | JP6980014B2 (https=) |
| KR (1) | KR102517273B1 (https=) |
| CN (1) | CN110214141B (https=) |
| AU (1) | AU2017364308B2 (https=) |
| CA (1) | CA3043132A1 (https=) |
| DK (1) | DK3544981T3 (https=) |
| EA (1) | EA039607B1 (https=) |
| ES (1) | ES2890226T3 (https=) |
| GB (1) | GB201619694D0 (https=) |
| HU (1) | HUE055692T2 (https=) |
| IL (1) | IL266745B (https=) |
| MA (1) | MA46878A (https=) |
| MX (1) | MX389496B (https=) |
| PL (1) | PL3544981T3 (https=) |
| PT (1) | PT3544981T (https=) |
| TW (1) | TWI756305B (https=) |
| WO (1) | WO2018096325A1 (https=) |
| ZA (1) | ZA201902710B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201610854D0 (en) | 2016-06-21 | 2016-08-03 | Entpr Therapeutics Ltd | Compounds |
| GB201619694D0 (en) | 2016-11-22 | 2017-01-04 | Entpr Therapeutics Ltd | Compounds |
| GB201717051D0 (en) * | 2017-10-17 | 2017-11-29 | Enterprise Therapeutics Ltd | Compounds |
| GB201801355D0 (en) | 2018-01-26 | 2018-03-14 | Enterprise Therapeutics Ltd | Compounds |
| GB201808093D0 (en) * | 2018-05-18 | 2018-07-04 | Enterprise Therapeutics Ltd | Compounds |
| GB201908453D0 (en) | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
| CR20220006A (es) | 2019-06-12 | 2022-06-06 | Tmem16A Ltd | Compuestos para tratar enfermedad respiratoria |
| GB201910608D0 (en) | 2019-07-24 | 2019-09-04 | Enterprise Therapeutics Ltd | Compounds |
| EP4259607A1 (en) * | 2020-12-11 | 2023-10-18 | Tmem16A Limited | Benzimidazole derivatives for treating respiratory disease |
| CN118852442A (zh) | 2023-04-26 | 2024-10-29 | 上海麦科思生物医药有限公司 | 抗ptk7抗体及其用途 |
| GB202406247D0 (en) | 2024-05-03 | 2024-06-19 | Enterprise Therapeutics Ltd | Compounds and pharmaceutical compositions |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US6858614B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenolic guanidine sodium channel blockers |
| US6903105B2 (en) | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| US20050090505A1 (en) | 2003-08-18 | 2005-04-28 | Johnson Michael R. | Methods of reducing risk of infection from pathogens |
| AU2004266704B2 (en) | 2003-08-18 | 2012-02-23 | Parion Sciences, Inc. | Capped pyrazinoylguanidine sodium channel blockers |
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