NZ758291A - Phenyl-2-hydroxy-acetylamino-2-methyl-phenyl compounds - Google Patents
Phenyl-2-hydroxy-acetylamino-2-methyl-phenyl compoundsInfo
- Publication number
- NZ758291A NZ758291A NZ758291A NZ75829118A NZ758291A NZ 758291 A NZ758291 A NZ 758291A NZ 758291 A NZ758291 A NZ 758291A NZ 75829118 A NZ75829118 A NZ 75829118A NZ 758291 A NZ758291 A NZ 758291A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- methyl
- amino
- formula
- phenyl
- Prior art date
Links
Classifications
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
- C07D241/28—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms in which said hetero-bound carbon atoms have double bonds to oxygen, sulfur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention provides phenyl-2-hydroxy-acetylamino-2-methyl-phenyl compounds, to pharmaceutical compositions comprising the compounds, to methods of using the compounds to treat physiological disorders such as cancer.
Claims (23)
1. A compound of the formula wherein R is ed from the group consisting of X is CH or N; R1 is hydrogen or fluoro; and R2 is C1 to C3 alkyl; or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 of the formula wherein R is selected from the group consisting of X is CH or N; R1 is hydrogen or fluoro; and R2 is C1 to C3 alkyl; or a ceutically acceptable salt thereof.
3. The compound or salt of either claim 1 or 2 wherein R is
4. The compound or salt of either claim 1 or 2 wherein X is CH or N; R1 is hydrogen or fluoro; and R2 is methyl or isopropyl.
5. The nd or salt of either claim 1 or 2 wherein R is
6. The compound of either claim 1 or 2 which is 3-amino[4-[[(2R)(3,5- difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N-methyl-pyrazine carboxamide which is represented by the formula or a pharmaceutically acceptable salt thereof.
7. The compound of either claim 1 or 2 which is o[4-[[(2R)(3,5- difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N-isopropyl-pyridine carboxamide which is represented by the formula or a pharmaceutically acceptable salt thereof.
8. The compound of claim 7 which is 2-amino[4-[[(2R)(3,5-difluorophenyl) hydroxy-acetyl]amino]methyl-phenyl]-N-isopropyl-pyridinecarboxamide which is represented by the formula
9. The compound of claim 7 which is a pharmaceutically acceptable salt of 2-amino [4-[[(2R)(3,5-difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N- isopropyl-pyridinecarboxamide which is ented by the formula
10. The compound of either claim 1 or 2 which is (2R)-N-[4-(4-aminomethylpyrrolo [2,3-d]pyrimidinyl)methyl-phenyl](3-fluorophenyl)hydroxyacetamide which is ented by the formula or a pharmaceutically acceptable salt thereof.
11. A pharmaceutical composition, sing a compound or a pharmaceutically able salt thereof according to any one of claims 1-10 with one or more pharmaceutically acceptable carriers, diluents, or excipients.
12. Use of a compound of the formula or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of cancer; R is selected from the group consisting of X is CH or N; R1 is hydrogen or fluoro; and R2 is C1 to C3 alkyl.
13. Use of a compound of the formula or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for ing antitumor activity by inhibiting n kinase R-like endoplasmic reticulum kinase (PERK); wherein R is selected from the group consisting of X is CH or N; R1 is hydrogen or fluoro; and R2 is C1 to C3 alkyl.
14. The use of claim 12 or 13, wherein the compound is of the formula wherein R is selected from the group consisting of X is CH or N; R1 is hydrogen or fluoro; and R2 is C1 to C3 alkyl; or a pharmaceutically able salt thereof.
15. The use of any of claims 12-14 wherein R is
16. The use of any of claims 12-14 wherein X is CH or N; R1 is hydrogen or fluoro; and R2 is methyl or isopropyl.
17. The use of any of claims 12-14 wherein R is
18. The use of any of claims 12-14, wherein the compound is 3-amino[4-[[(2R) (3,5-difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N-methyl-pyrazine- 2-carboxamide which is represented by the formula or a pharmaceutically acceptable salt thereof.
19. The use of any of claims 12-14, wherein the compound is 2-amino[4-[[(2R) (3,5-difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N-isopropylpyridinecarboxamide which is represented by the a or a pharmaceutically able salt thereof.
20. The use of claim 19, wherein the compound is 2-amino[4-[[(2R)(3,5- difluorophenyl)hydroxy-acetyl]amino]methyl-phenyl]-N-isopropyl-pyridine carboxamide which is ented by the formula
21. The use of claim 19, wherein the compound is a pharmaceutically acceptable salt of 2-amino[4-[[(2R)(3,5-difluorophenyl)hydroxy-acetyl]amino]methylphenyl ]-N-isopropyl-pyridinecarboxamide which is represented by the formula
22. The use of any of claims 12-14, wherein the compound is (2R)-N-[4-(4-amino methyl-pyrrolo[2,3-d]pyrimidinyl)methyl-phenyl](3-fluorophenyl) hydroxy-acetamide which is represented by the formula or a pharmaceutically acceptable salt f.
23. The use of any one of claims 12 or 14-22, wherein the cancer is pancreatic cancer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17382207 | 2017-04-18 | ||
| PCT/US2018/027005 WO2018194885A1 (en) | 2017-04-18 | 2018-04-11 | Phenyl-2-hydroxy-acetylamino-2-methyl-phenyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ758291A true NZ758291A (en) | 2025-11-28 |
| NZ758291B2 NZ758291B2 (en) | 2026-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 11 APR 2027 BY ANAQUA SERVICES Effective date: 20260320 |