NZ758561A - Pyrrolo[2,1-f][1,2,4]triazines useful for treating respiratory syncitial virus infections - Google Patents
Pyrrolo[2,1-f][1,2,4]triazines useful for treating respiratory syncitial virus infectionsInfo
- Publication number
- NZ758561A NZ758561A NZ758561A NZ75856114A NZ758561A NZ 758561 A NZ758561 A NZ 758561A NZ 758561 A NZ758561 A NZ 758561A NZ 75856114 A NZ75856114 A NZ 75856114A NZ 758561 A NZ758561 A NZ 758561A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- alkyl
- salt according
- Prior art date
Links
- 230000009385 viral infection Effects 0.000 title claims abstract 4
- KGRPHHFLPMPUBB-UHFFFAOYSA-N pyrrolo[2,1-f][1,2,4]triazine Chemical class C1=NC=NN2C=CC=C21 KGRPHHFLPMPUBB-UHFFFAOYSA-N 0.000 title 1
- 230000000241 respiratory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 241000711904 Pneumoviridae Species 0.000 claims abstract 3
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000030925 respiratory syncytial virus infectious disease Diseases 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920002554 vinyl polymer Chemical group 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- UYZDOULEOAVJCL-QFOLPQNPSA-N (2R,3S,4R,5S)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-(chloromethyl)-2-(hydroxymethyl)oxolane-3,4-diol Chemical compound NC1=NC=NN2C1=CC=C2[C@H]2[C@@H]([C@@H]([C@](O2)(CO)CCl)O)O UYZDOULEOAVJCL-QFOLPQNPSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Provided herein are formulations, methods and substituted tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds of Formula (I) for treating Pneumovirinae virus infections, including respiratory syncytial virus infections, as well as methods and intermediates for synthesis of tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds. This includes compounds of formula (I) where R1 is H or F; R2 is H or F; R3 is OH; R4 is haloalkyl; R6 is OH and R5 is H, phosphoric acid or a derivative thereof. Representative compounds of formula (I) include (2R,3S,4R,5S)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2- (chloromethyl)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol.
Claims (21)
1. A compound of Formula (I): 5 or a pharmaceutically acceptable salt thereof, wherein: R is H or F; R is H or F; R is OH or F; R is C -C alkyl, C -C alkenyl, C -C alkynyl, C -C cycloalkyl, azido, halogen, or 1 4 2 4 2 4 3 4 10 C -C haloalkyl; R is OH; and R is selected from the group of H and: wherein: n’ is selected from 1, 2, 3, and 4; R is selected from C -C alkyl, O-C -C alkyl, benzyl, -O-benzyl, -CH -C -C cycloalkyl, - 1 8 1 8 2 3 6 5 O-CH -C -C cycloalkyl, and CF ; 2 3 6 3 R is selected from phenyl, 1-naphthyl, 2-naphthyl, R is selected from H and CH ; R is selected from H or C -C alkyl; and 10 R is selected from H, C -C alkyl, benzyl, C -C cycloalkyl, and –CH -C -C 1 8 3 6 2 3 6 cycloalkyl.
2. The compound or the pharmaceutically acceptable salt according to claim 1, wherein R is H.
3. The compound or the pharmaceutically acceptable salt according to claim 1 or 2, wherein R is H.
4. The compound or the pharmaceutically acceptable salt according to any one of claims 1-3, wherein the compound is of Formula (II):
5.5. The compound or the pharmaceutically acceptable salt according to any one of claims 1-4, wherein R is methyl, ethyl, ethenyl, azido, -CH Cl, -CH F, -CHF , or –CF . 2 2 2 3
6. The compound or the pharmaceutically acceptable salt according to any one of claims 1-5, wherein R is F.
7. The compound or the pharmaceutically acceptable salt according to any one of claims 1-5, wherein R is OH.
8. The compound or the pharmaceutically acceptable salt according to claim 4, 15 wherein R is methyl, ethyl, vinyl, or ethynyl.
9.The compound or the pharmaceutically acceptable salt according to claim 7, wherein R is halomethyl.
10. The compound or the pharmaceutically acceptable salt according to any one of claims 1-9, wherein R is H.
11. The compound or the pharmaceutically acceptable salt according to any one of 5 claims 1-9, wherein R is selected from the group of: wherein: R is selected from C -C alkyl, -O-C -C alkyl, benzyl, and -CH -C -C cycloalkyl; 1 8 1 8 2 3 6 10 and R is selected from C -C alkyl, benzyl, C -C cycloalkyl, and –CH -C -C 1 8 3 6 2 3 6 cycloalkyl.
12. The compound or the pharmaceutically acceptable salt according to any one of 15 claims 1 to 9 or 11, wherein either: (A) R is selected from C -C alkyl; or (B) R is selected from C -C alkyl; or (C) R is selected from C -C alkyl; or (D) R is selected from C -C alkyl; or (E) R is selected from C -C alkyl; or (F) R is selected from C -C alkyl.
13. The compound or the pharmaceutically acceptable salt according to any one of 5 claims 1-11, wherein R is selected from the group of H and:
14. The compound or the pharmaceutically acceptable salt according to any one of claims 1-9 or 11, wherein R is:
15. The compound or the pharmaceutically acceptable salt according to any one of claims 1-9 or 11, wherein R is:
16. The compound or the pharmaceutically acceptable salt according to any one of claims 1-9 or 11, wherein R is:
17. The compound or the pharmaceutically acceptable salt according to claim 1 selected from the group of:
18. A pharmaceutical formulation comprising a pharmaceutically effective amount of 5 the compound or the pharmaceutically acceptable salt of any one of claims 1-17 and a pharmaceutically acceptable carrier or excipient.
19. Use of the compound or the pharmaceutically acceptable salt of any one of claims 1-17 for the manufacture of a medicament for the treatment of a Pneumovirinae virus infection in a human. 5
20. The compound or the pharmaceutically acceptable salt of any one of claims 1-17 for use in the treatment of a Pneumovirinae virus infection or a respiratory syncytial virus infection in a human.
21. Use of the compound or the pharmaceutically acceptable salt of any one of claims 10 1-17 for the manufacture of a medicament for the treatment of a respiratory syncytial virus infection in a human.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361902544P | 2013-11-11 | 2013-11-11 | |
| NZ74649714 | 2014-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ758561A true NZ758561A (en) | 2023-11-24 |
| NZ758561B2 NZ758561B2 (en) | 2024-02-27 |
Family
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ERR | Error or correction |
Free format text: THE TITLE HAS BEEN CORRECTED TO TITLE: PYRROLO(2,1-F)(1,2,4)TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS; FILING DATE: 25 OCT 2019; STATUS: REJECTED; KIND CODE: A1 PUBLICATION DATE: 29 NOV 2019; TITLE: PYRROLO(2,1-F)(1,2,4)TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS; FILING DATE: 02 SEP 2021; STATUS: REJECTED; KIND CODE: TITLE: PYRROLO(2,1-F)(1,2,4)TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS; FILING DATE: 22 DEC 2021; STATUS: REJECTED; KIND CODE: TITLE: PYRROLO(2,1-F)(1,2,4)TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS; FILING DATE: 08 FEB 2022; STATUS: REJECTED; KIND CODE: TITLE: PYRROLO( Effective date: 20231108 |
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| PSEA | Patent sealed |