NZ767738B2 - Arginase inhibitors and methods of use thereof - Google Patents
Arginase inhibitors and methods of use thereofInfo
- Publication number
- NZ767738B2 NZ767738B2 NZ767738A NZ76773819A NZ767738B2 NZ 767738 B2 NZ767738 B2 NZ 767738B2 NZ 767738 A NZ767738 A NZ 767738A NZ 76773819 A NZ76773819 A NZ 76773819A NZ 767738 B2 NZ767738 B2 NZ 767738B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- formula
- treating
- Prior art date
Links
- 102000004452 Arginase Human genes 0.000 title abstract 2
- 108700024123 Arginases Proteins 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 208000027866 inflammatory disease Diseases 0.000 claims abstract 4
- 230000000241 respiratory effect Effects 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract 3
- 201000011510 cancer Diseases 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 2
- IVDBGHPEQSTHRK-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOO IVDBGHPEQSTHRK-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
Classifications
-
- 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
- A61K31/69—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Abstract
Disclosed are compounds of formula (Ia) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of formula (Ia) and methods of using the same for treating cancer or a respiratory inflammatory disease and inhibiting arginase, wherein R1is -NHR1a; R1ais -H or -C(O)CH(R1b)NHR1c; and R1bis selected from -H, -(C1-C4) alkyl and CH2OR1dand R1cis -H; or R1band R1c, together with the atom to which they are attached, form a 5-membered heterocyclic ring; and R1dis H or -CH3.
Claims (16)
1. A compound of formula (I), or a pharmaceutically able salt thereof: wherein R1 is -NHR1a; R1a is -H or -C(O)CH(R1b)NH2; and R1b is selected from -CH3 or -CH(CH3)2.
2. A compound of formula (II), or a pharmaceutically acceptable salt f: wherein R2 is -OH or -NHR2a; R2a is -H or -C(O)CH(R2b)NH2; R2b is -CH3 or -CH(CH3)2.
3. The compound of claim 2, wherein the compound is a compound of formula (III), or a pharmaceutically acceptable salt thereof: R3 (III) wherein R3 is -CH3 or -CH(CH3)2.
4. A compound of formula (Ib), or a pharmaceutically acceptable salt thereof: wherein R1 is -NHR1a; R1a is -H or -C(O)CH(R1b)NH2; and R1b is selected from -CH3 or -CH(CH3)2.
5. A compound of formula (IIb), or a pharmaceutically acceptable salt thereof: (IIb) wherein R2 is -OH or -NHR2a; R2a is -H or -C(O)CH(R2b)NH2; R2b is -CH3 or -CH(CH3).
6. The compound of claim 5, wherein the compound is a compound of a (IIIb), or a pharmaceutically able salt thereof: (IIIb) R3 is -CH3 or -CH(CH3)2.
7. The compound of claim 1, wherein the compound is selected from: or a pharmaceutically acceptable salt thereof.
8. The compound of claim 2, wherein the compound is: or a pharmaceutically acceptable salt thereof.
9. The compound of claim 4, wherein the nd is: or a pharmaceutically acceptable salt thereof.
10. A pharmaceutical composition comprising a compound of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
11. A compound of any one of Claims 1 to 9, or a ceutically acceptable salt thereof, for use in treating cancer.
12. Use of a compound of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for treating .
13. A pharmaceutical ition comprising a compound of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof, for use in treating cancer.
14. A nd of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof, for use in treating a respiratory inflammatory disease.
15. Use of a compound of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof in the manufacture of a ment for treating a respiratory inflammatory disease.
16. A pharmaceutical composition comprising a compound of any one of Claims 1 to 9, or a pharmaceutically acceptable salt thereof, for use in treating a respiratory inflammatory disease. Egg Egg 2535 Egg Egg :5 :5 Em Em Em E SEE S SEE S SE 3 SE5 3 SE5 3 3 3 3 3 om ON 3 ON o. mm mm 2 mm LO. 3 3, 3 3 3, mm mm mm mm mm 3 3 3 3 3 3 3 3 3 3 om, on 3 on 3 mm mm, mm 3 mm 3 3 3 3 3 3 3 E 8 3 S S E S E < 3 E 0 E a E 3 3 3 3 3 3 09.0 mmod 080 $5 08.0 33 mooBo 5.0 3 o So 08.0 33 r939“— on 85er .®_n_ mmoo omod mmod omod mad 05.0 mood md md ca 09 me me ON ON mm 0N o. o. 03 m m. m. Oa) 259 m Egg ocn Em Qv Em m; SE96 min «2:55 WSmE on Qm mam mam Om ob no we OK ox m ?-mmro v mmx—o x—omoolxco lxmm ooooooooooo ooooooooooo
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862631659P | 2018-02-17 | 2018-02-17 | |
| US201862671576P | 2018-05-15 | 2018-05-15 | |
| US201862721113P | 2018-08-22 | 2018-08-22 | |
| US201862778002P | 2018-12-11 | 2018-12-11 | |
| PCT/IB2019/051236 WO2019159120A1 (en) | 2018-02-17 | 2019-02-15 | Arginase inhibitors and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ767738A NZ767738A (en) | 2023-12-22 |
| NZ767738B2 true NZ767738B2 (en) | 2024-03-26 |
Family
ID=
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