JP2019535747A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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 |
|---|---|---|---|
| GB1619694.1 | 2016-11-22 | ||
| GBGB1619694.1A GB201619694D0 (en) | 2016-11-22 | 2016-11-22 | Compounds |
| 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 (enExample) | 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 (enExample) |
| EP (1) | EP3544981B1 (enExample) |
| JP (1) | JP6980014B2 (enExample) |
| KR (1) | KR102517273B1 (enExample) |
| CN (1) | CN110214141B (enExample) |
| AU (1) | AU2017364308B2 (enExample) |
| CA (1) | CA3043132A1 (enExample) |
| DK (1) | DK3544981T3 (enExample) |
| EA (1) | EA039607B1 (enExample) |
| ES (1) | ES2890226T3 (enExample) |
| GB (1) | GB201619694D0 (enExample) |
| HU (1) | HUE055692T2 (enExample) |
| IL (1) | IL266745B (enExample) |
| MA (1) | MA46878A (enExample) |
| MX (1) | MX389496B (enExample) |
| PL (1) | PL3544981T3 (enExample) |
| PT (1) | PT3544981T (enExample) |
| TW (1) | TWI756305B (enExample) |
| WO (1) | WO2018096325A1 (enExample) |
| ZA (1) | ZA201902710B (enExample) |
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 |
| AU2020290049A1 (en) | 2019-06-12 | 2022-02-03 | Tmem16A Limited | Compounds for treating respiratory disease |
| GB201910608D0 (en) | 2019-07-24 | 2019-09-04 | Enterprise Therapeutics Ltd | Compounds |
| JP2023552638A (ja) | 2020-12-11 | 2023-12-18 | ティーエムイーエム１６エー リミテッド | 呼吸器疾患を治療するためのベンゾイミダゾール誘導体 |
| 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 |
|---|---|---|---|---|
| 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 |
| CA2534569A1 (en) | 2003-08-18 | 2005-02-24 | Parion Sciences, Inc. | Cyclic pyrazinoylguanidine 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 |
| AU2004271945A1 (en) | 2003-08-18 | 2005-03-24 | Parion Sciences, Inc. | Aliphatic pyrazinoylguanidine sodium channel blockers |
| US7745442B2 (en) | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
| WO2005042497A2 (en) * | 2003-10-28 | 2005-05-12 | Vertex Pharmaceuticals, Incorporated | Benzimidazoles useful as modulators of ion channels |
| US7399766B2 (en) | 2004-08-18 | 2008-07-15 | Parion Sciences, Inc. | Soluble amide & ester pyrazinoylguanidine sodium channel blockers |
| CA2600570C (en) * | 2005-03-14 | 2011-12-06 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as .beta.-secretase inhibitors |
| US7807834B2 (en) | 2005-08-03 | 2010-10-05 | Parion Sciences, Inc. | Capped pyrazinoylguanidine sodium channel blockers |
| GB0526240D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| GB0526244D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| WO2008124491A1 (en) | 2007-04-03 | 2008-10-16 | Parion Sciences, Inc. | Pyrazinoylguanidine compounds for use taste modulators |
| US8318935B2 (en) | 2007-05-07 | 2012-11-27 | Novartis Ag | Organic compounds 75074 |
| WO2009019506A1 (en) | 2007-08-03 | 2009-02-12 | Astrazeneca Ab | Heterocyclyc sulfonamides having edg-1 antagonistic activity |
| EP2231280B1 (en) | 2007-12-10 | 2016-08-10 | Novartis AG | Amiloride-like Pyrazine-carboxamides as ENaC blockers |
| EP2257296B1 (en) | 2008-02-26 | 2014-05-07 | Parion Sciences, Inc. | Poly aromatic sodium channel blockers |
| CN102015662A (zh) | 2008-05-13 | 2011-04-13 | 诺瓦提斯公司 | 3,5-二氨基-6-氯-吡嗪-2-甲酸衍生物和它们作为上皮钠通道阻断剂用于治疗气道疾病的用途 |
| BRPI0915018A2 (pt) | 2008-06-10 | 2015-10-27 | Novartis Ag | compostos orgânicos |
| WO2011028740A1 (en) | 2009-09-03 | 2011-03-10 | Glaxo Group Limited | ENaC BLOCKERS |
| WO2011079087A1 (en) | 2009-12-23 | 2011-06-30 | Glaxo Group Limited | Enac blockers |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| TW201204353A (en) * | 2010-06-08 | 2012-02-01 | Vertex Pharma | Formulations of (R)-1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
| SI2773633T1 (sl) | 2011-11-02 | 2017-11-30 | Boehringer Ingelheim International Gmbh | Heterociklične spojine, zdravila, ki vsebujejo te spojine, njihova uporaba in postopki za njihovo pripravo |
| US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| EA201990616A3 (ru) | 2012-05-29 | 2019-12-30 | Парион Сайэнс, Инк. | Дендримероподобные аминоамиды, обладающие активностью блокаторов натриевых каналов, для лечения сухости глаз и других заболеваний слизистых оболочек |
| US8841309B2 (en) | 2012-09-24 | 2014-09-23 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| CN105073717B (zh) | 2012-12-17 | 2018-05-22 | 帕里昂科学公司 | 可用于治疗由黏膜水化不足造成的疾病的氯-吡嗪甲酰胺衍生物 |
| CN108658876A (zh) | 2012-12-17 | 2018-10-16 | 帕里昂科学公司 | 3,5-二氨基-6-氯-n-(n-(4-苯基丁基)甲脒基)吡嗪-2-甲酰胺化合物 |
| ES2674665T3 (es) | 2012-12-17 | 2018-07-03 | Parion Sciences, Inc. | Compuestos de 3,5-diamino-6-cloro-N-(N-(4-fenilbutilo)carbamimidoilo)-pirazina-2-carboxamida |
| EP2991981B1 (en) | 2013-04-30 | 2017-03-01 | Boehringer Ingelheim International GmbH | Diaminopyrazine compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof |
| CN105518000B (zh) | 2013-07-02 | 2018-09-14 | 加州生物医学研究所 | 用于治疗囊性纤维化的化合物 |
| JP6449870B2 (ja) | 2013-07-08 | 2019-01-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 肺および気道の疾患を処置するための上皮性ナトリウムチャネルの阻害剤としてのアミロライド型化合物 |
| EP3022197B1 (en) | 2013-07-15 | 2017-09-06 | Boehringer Ingelheim International GmbH | Novel tetra- and pentasubstituted benzimidazolium compounds |
| JP6461134B2 (ja) | 2013-07-15 | 2019-01-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ベンゾイミダゾリウム化合物 |
| EP3022198B1 (en) | 2013-07-15 | 2019-09-11 | Boehringer Ingelheim International GmbH | Novel 5-substituted benzimidazolium compounds |
| WO2015018754A1 (en) | 2013-08-08 | 2015-02-12 | Boehringer Ingelheim International Gmbh | Novel pyrazine amide compounds |
| JP6667538B2 (ja) | 2015-01-12 | 2020-03-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 呼吸器系疾患の治療に有用な置換ベンズイミダゾリウム化合物 |
| US10155749B2 (en) * | 2015-01-12 | 2018-12-18 | Boehringer Ingelheim International Gmbh | Substituted benzimidazolium compounds useful in the treatment of respiratory diseases |
| WO2016113169A1 (en) | 2015-01-12 | 2016-07-21 | Boehringer Ingelheim International Gmbh | Tetra- and pentasubstituted benzimidazolium compounds useful in the treatment of respiratory diseases |
| EP3245200B1 (en) | 2015-01-12 | 2021-03-10 | Boehringer Ingelheim International GmbH | 2-(pyrazin-2-ylcarbonylaminomethyl)benzimidazolium compounds as epithelial sodium channel inhibitors |
| JP6620171B2 (ja) | 2015-08-20 | 2019-12-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規縮環フェノキシアセトアミド |
| CN108135897B (zh) | 2015-08-20 | 2021-07-27 | 勃林格殷格翰国际有限公司 | 稠合的苯甲酰胺 |
| GB201610854D0 (en) * | 2016-06-21 | 2016-08-03 | Entpr Therapeutics Ltd | Compounds |
| GB201619694D0 (en) * | 2016-11-22 | 2017-01-04 | Entpr Therapeutics Ltd | Compounds |
-
2016
- 2016-11-22 GB GBGB1619694.1A patent/GB201619694D0/en not_active Ceased
-
2017
- 2017-11-22 CN CN201780084165.3A patent/CN110214141B/zh active Active
- 2017-11-22 ES ES17807900T patent/ES2890226T3/es active Active
- 2017-11-22 EP EP17807900.0A patent/EP3544981B1/en active Active
- 2017-11-22 US US16/462,794 patent/US10941149B2/en active Active
- 2017-11-22 EA EA201991253A patent/EA039607B1/ru unknown
- 2017-11-22 DK DK17807900.0T patent/DK3544981T3/da active
- 2017-11-22 WO PCT/GB2017/053499 patent/WO2018096325A1/en not_active Ceased
- 2017-11-22 MA MA046878A patent/MA46878A/fr unknown
- 2017-11-22 PL PL17807900T patent/PL3544981T3/pl unknown
- 2017-11-22 KR KR1020197016141A patent/KR102517273B1/ko active Active
- 2017-11-22 AU AU2017364308A patent/AU2017364308B2/en active Active
- 2017-11-22 HU HUE17807900A patent/HUE055692T2/hu unknown
- 2017-11-22 CA CA3043132A patent/CA3043132A1/en active Pending
- 2017-11-22 TW TW106140573A patent/TWI756305B/zh active
- 2017-11-22 MX MX2019005934A patent/MX389496B/es unknown
- 2017-11-22 PT PT178079000T patent/PT3544981T/pt unknown
- 2017-11-22 JP JP2019527365A patent/JP6980014B2/ja active Active
-
2019
- 2019-04-30 ZA ZA2019/02710A patent/ZA201902710B/en unknown
- 2019-05-20 IL IL266745A patent/IL266745B/en unknown
-
2020
- 2020-11-24 US US17/103,559 patent/US11739094B2/en active Active
-
2023
- 2023-06-30 US US18/345,840 patent/US12371436B2/en active Active
-
2025
- 2025-06-11 US US19/235,076 patent/US20250304590A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019535747A5 (enExample) | ||
| JP6363616B2 (ja) | オートタキシン阻害剤 | |
| KR102827138B1 (ko) | 화합물 | |
| CA2993918C (en) | 1,3,4-oxadiazole amide derivative compound as histone deacetylase 6 inhibitor, and pharmaceutical composition containing same | |
| JP2022009408A (ja) | カンナビノイド受容体モジュレーター | |
| CN113518618A (zh) | 化合物、组合物及方法 | |
| ES2298757T3 (es) | Derivados de z-amino-piridina como agonistas de adrecorreceptores beta-2. | |
| ES2384121T3 (es) | Compuestos de N-hidroxiacrilamida | |
| BRPI0912878A2 (pt) | derivados de indazóis substituídos por fenila e benzodioxinila | |
| JP6454418B2 (ja) | ピラゾール誘導体、またはその薬理学的に許容される塩 | |
| RS56424B1 (sr) | Piridin-2-amidi korisni kao cb2-agonisti | |
| EP2621275A1 (en) | Aryl-substituted imidazoles | |
| WO2020167994A1 (en) | Compounds, compositions and methods | |
| KR20230002483A (ko) | Bcl-2 단백질 억제제 | |
| WO2017040606A1 (en) | Isoxazole derivatives for use in the treatment of pulmonary diseases and disorders | |
| JPH0347172A (ja) | 脳内虚血症治療用剤 | |
| JP2013542267A5 (enExample) | ||
| KR20100122489A (ko) | 아제티딘-유도 화합물, 그의 제조 방법 및 그의 치료학적 용도 | |
| ES3057235T3 (en) | Isoxazolidines as ripk1 inhibitors and use thereof | |
| US20140171403A1 (en) | Autotaxin inhibitors | |
| JP2020537658A5 (enExample) | ||
| US20230181746A1 (en) | Benzoylhydrazide-derived hdac degraders as therapeutics for treating cancer and other human diseases | |
| MX2014000112A (es) | Bloqueantes de los canales de sodio dependientes de voltaje. | |
| CN102203060B (zh) | 3-(苄基氨基)-吡咯烷衍生物和它们作为nk-3 受体拮抗剂的应用 | |
| JP2008508251A5 (enExample) |