NZ757929B2 - Benzoazepine analogs as inhibiting agents for bruton's tyrosine kinase - Google Patents
Benzoazepine analogs as inhibiting agents for bruton's tyrosine kinaseInfo
- Publication number
- NZ757929B2 NZ757929B2 NZ757929A NZ75792918A NZ757929B2 NZ 757929 B2 NZ757929 B2 NZ 757929B2 NZ 757929 A NZ757929 A NZ 757929A NZ 75792918 A NZ75792918 A NZ 75792918A NZ 757929 B2 NZ757929 B2 NZ 757929B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- crystalline form
- angles
- rule
- substitute sheet
- pxrd peaks
- Prior art date
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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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
Provided are compounds of Formula (I), or pharmaceutically acceptable salts thereof, and methods for their production and compounds of formula (I) for use in treating a disease responsive to the inhibition of Bruton's tyrosine.
Claims (23)
1. A compound represented by the following formula: H N N O N N N N H , or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1, or a pharmaceutically acceptable salt f, wherein the nd is represented by the following formula: O N N N N H , or a pharmaceutically acceptable salt thereof.
3. Crystalline Form A of (R)(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol yl)amino)pyrimidinyl)(oxetanyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepinyl)-1H-1,2,3- lecarboxamide, wherein the crystalline form is characterized by at least three powder X- ray diffraction (PXRD) peaks at 2? angles selected from 5.7°, 7.9°, 9.7°, 18.2°, 19.0° and 22.4°.
4. The crystalline Form A of claim 3, wherein the crystalline form is characterized by at least four PXRD peaks at 2? angles selected from 5.7°, 7.9°, 9.7°, 18.2°, 19.0° and 22.4°.
5. The crystalline Form A of claim 3, n the crystalline form is characterized by at least five PXRD peaks at 2? angles selected from 5.7°, 7.9°, 9.7°, 18.2°, 19.0° and 22.4°.
6. The crystalline Form A of claim 3, wherein the crystalline form is characterized by PXRD peaks at 2? angles of 5.7°, 7.9°, 9.7°, 18.2°, 19.0° and 22.4°.
7. The crystalline Form A of claim 3, wherein the crystalline form is characterized by PXRD peaks at 2? angles of 4.3°, 5.7°, 7.9°, 8.7°, 9.7°, 11.9°, 13.1°, 14.8°, 15.2°, 16.1°, 17.0°, 17.8°, 18.2°, 19.0°, 20.5°, 21.2°, 22.4°, 22.8°, 23.8°, and 25.6°.
8. The lline Form A of any one of claims 3-7, wherein the crystalline form A is characterized by a melting temperature of 186.0 °C ± 2 °C determined by differential scanning calorimetry (DSC) analysis.
9. The crystalline Form A of any one of claims 3-8, wherein the crystalline form has a DSC profile that is substantially the same as DSC profile shown in
10. The crystalline Form A of any one of claims 3-9, wherein the crystalline form A is a hydrate.
11. The crystalline Form A of any one of claims 3-10, wherein the crystalline Form A is at least 70%, 80%, 85%, 90%, 95%, 97%, 99%, 99.5% or 99.9% pure.
12. Crystalline Form G of (R)(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol no)pyrimidinyl)(oxetanyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepinyl)-1H-1,2,3- triazolecarboxamide, n the crystalline form is characterized by at least three PXRD peaks at 2? angles selected from 3.6°, 8.9°, 10.9°, 12.6°, 20.2° and 21.8°.
13. The crystalline Form G of claim 12, wherein the crystalline form is characterized by at least four PXRD peaks at 2? angles selected from 3.6°, 8.9°, 10.9°, 12.6°, 20.2° and 21.8°.
14. The crystalline Form G of claim 12, wherein the crystalline form is characterized by PXRD peaks at 2? angles of 3.6°, 8.9°, 10.9°, 12.6°, 20.2° and 21.8°.
15. The crystalline Form G of claim 12, wherein the crystalline form is characterized by PXRD peaks at 2? angles of 3.6°, 8.9°, 11.0°, 12.6°, 14.5°, 15.4°, 16.3°, 18.4°, 20.2°, 21.8°, 23.4°, 25.4°, 26.8°, and 34.2°.
16. The crystalline Form G of any one of claims 12-15, wherein the crystalline Form G has a g temperature of 217.3 °C ± 2 °C determined by differential scanning calorimetry (DSC) is.
17. The crystalline Form G of any one of claims 12-16, wherein the crystalline Form G has a DSC profile that is substantially the same as the DSC profile shown in
18. The crystalline Form G of any one of claims 12-17, wherein the crystalline Form G is an anhydrate.
19. The crystalline Form G of any one of claims 12-18, wherein the crystalline Form G is at least 70%, 80%, 85%, 90%, 95%, 97%, 99%, 99.5% or 99.9% pure .
20. A pharmaceutical composition comprising (i) a compound of any one of claims 1- 2, or a pharmaceutically acceptable salt thereof, (ii) a crystalline Form A of any one of claims 3- 11, or (iii) a crystalline Form G of any one of claims 12-19, and a pharmaceutically able
21. Use of (i) a compound of any one of claims 1 -2 or a pharmaceutically acceptable salt thereof, (ii) a crystalline Form A of any one of claims 3-11, or (iii) a crystalline Form G of any one of claims 12-19 for the manufacture of a medicament for the treatment of a disorder responsive to inhibition of Bruton’s tyrosine kinase in a human t.
22. The useof claim 21, wherein the disorder is an autoimmune disorder.
23. The use of claim 22, wherein the autoimmune disorder is multiple sclerosis. Form 33 27 1.54060 25 WL= 88’? 19 Tonheta/Theta) 17 ed 15 2Theta 006 008 001 009 009 0017 008 OOZ 00L 0 s1un03 SUBSTITUTE SHEET (RULE 26) (61M) M0|:l JEGH v .®_u_ Foo.<-mo-mo Foo.<-mo-mo 0mm Fm Fm rm Fm UmQ Gav 0&6: 933mm 2323—:8. Ooodmw om? 00? mm om mm ow mp (%) M EE>> SUBSTITUTE SHEET (RULE 26) 8 2: Enos: .®_n_ .®_n_ m8 SUBSTITUTE SHEET (RULE 26) Zl9 mm Show mm QVV R 88m. mm ids mm v 898 L‘ L01 a .®_u_ 66Z z.___:____:_::_::_ 2 Emct?m?oé €9Z :2 ___: t :__: :7: m; .8338 6LZ « 325 SUBSTITUTE SHEET (RULE 26) (61M) M0|:l leeH 358355 omm <._. m<-N m<-N Tmo Tmo Fm Fm oom Regs: Fm Fm UmQ 0mm 000.com oatma 9,28 oom GOV m... m.®_u_ om? oow om on om oxm SUBSTITUTE SHEET (RULE 26) 2: 23.3: :_ mm? 7g 09 L om? 0.|r.9/_.0.L900.77 LuLL mm? i: 99 ow? :0.0.9}. .77 LL mvr <© mo mm? .®_n_ .®_n_ om? SUBSTITUTE SHEET (RULE 26)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ798969A NZ798969B2 (en) | 2018-04-13 | Benzoazepine analogs as inhibiting agents for bruton's tyrosine kinase |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762485745P | 2017-04-14 | 2017-04-14 | |
| PCT/US2018/027415 WO2018191577A1 (en) | 2017-04-14 | 2018-04-13 | Benzoazepine analogs as inhibiting agents for bruton's tyrosine kinase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ757929A NZ757929A (en) | 2025-10-31 |
| NZ757929B2 true NZ757929B2 (en) | 2026-02-03 |
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