.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Details for Patent: 6,548,668

« Back to Dashboard

Details for Patent: 6,548,668

Title: Boronic ester and acid compounds, synthesis and uses
Abstract:Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.
Inventor(s): Adams; Julian (Brookline, MA), Ma; Yu-Ting (Lexington, MA), Stein; Ross (Sudbury, MA), Baevsky; Matthew (Boston, MA), Grenier; Louis (Medford, MA), Plamondon; Louis (Watertown, MA)
Assignee: Millennium Pharmaceuticals, Inc. (Cambridge, MA)
Filing Date:Mar 18, 2002
Application Number:10/100,295
Claims:1. A compound having the formula: ##STR52##

or a pharmaceutically acceptable salt thereof, wherein: P is R.sup.7 --C(O)-- or R.sup.7 --SO.sub.2 --, and R.sup.7 is heteroaryl or a saturated or partially unsaturated heterocycle; A is 1; B.sup.1 is CH; X.sup.1 is --C(O)--NH--; X.sup.2 is --C(O)--NH--; R is hydrogen or alkyl; R.sup.1 is hydrogen, C.sub.1-8 alkyl, C.sub.3-10 cycloalkyl, C.sub.6-10 aryl, or --CH.sub.2 --R.sup.5, where the ring portion of said aryl can be optionally substituted; R.sup.2 is hydrogen, C.sub.1-8 alkyl, C.sub.3-10 cycloalkyl, C.sub.6-10 aryl, or --CH.sub.2 --R.sup.5, where the ring portion of said aryl can be optionally substituted; R.sup.3 is C.sub.4 alkyl; R.sup.5 is one of C.sub.6-10 aryl, C.sub.6-10 ar(C.sub.1-6)alkyl, C.sub.1-6 alk(C.sub.6-10)aryl, C.sub.3-10 cycloalkyl, C.sub.1-8 alkoxy or --W--R.sup.6, where W is a chalcogen and R.sup.6 is alkyl, where the ring portion of any of said aryl, aralkyl, or alkaryl can be optionally substituted; and Z.sup.1 and Z.sup.2 are independently one of hydroxy, alkoxy, or aryloxy, or together Z.sup.1 and Z.sup.2 form a moiety derived from a dihydroxy compound having at least two hydroxy groups separated by at least two connecting atoms in a chain or ring, said chain or ring comprising carbon atoms and, optionally, a heteroatom or heteroatoms which can be N, S, or O.

2. The compound of claim 1, wherein P is R.sup.7 --C(O)--, and R.sup.7 is quinolinyl, pyrazinyl, pyridyl, quinoxalinyl or N-morpholinyl.

3. The compound of claim 1, wherein R.sup.3 is isobutyl.

4. The compound of claim 1, wherein Z.sup.1 and Z.sup.2 are independently one of hydroxy, C.sub.1-6 alkoxy, or C.sub.6-10 aryloxy.

5. The compound of claim 4, wherein Z.sup.1 and Z.sup.2 are both hydroxy.

6. A compound having the formula: ##STR53##

or a pharmaceutically acceptable salt thereof, wherein: P is R.sup.7 --C(O)-- or R.sup.7 --SO.sub.2 --, and R.sup.7 is heteroaryl or a saturated or partially unsaturated heterocycle; A is 1; B.sup.1 is CH; X.sup.1 is --C(O)--NH--; X.sup.2 is --C(O)--NH--; R is hydrogen or alkyl; R.sup.1 and R.sup.2 are each independently --CH.sub.2 --R.sup.5, where R.sup.5, in each instance, is one of aryl, aralkyl, alkaryl, cycloalkyl, or --W--R.sup.6, where W is a chalcogen and R.sup.6 is alkyl; where the ring portion of any of said aryl, aralkyl, or alkaryl in R.sup.1, R.sup.2 and R.sup.5 can be optionally substituted by one or two substitutes independently selected from the group consisting of C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.1-6 alkyl(C.sub.3-8)cycloalkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, cyano, amino, C.sub.1-6 alkylamino, di(C.sub.1-6)alkylamino, benzylamino, dibenzylamino, nitro, carboxy, carbo(C.sub.1-6)alkoxy, trifluoromethyl, halogen, C.sub.1-6 alkoxy, C.sub.6-10 aryl, C.sub.6-10 aryl(C.sub.1-6)alkyl, C.sub.6-10 aryl(C.sub.1-6)alkoxy, hydroxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfinyl, C.sub.1-6 alkylsulfonyl, C.sub.6-10 arylthio, C.sub.6-10 arylsulfinyl, C.sub.6-10 arylsulfonyl, C.sub.6-10 aryl, C.sub.1-6 alkyl(C.sub.6-10)aryl, and halo(C.sub.6-10)aryl; R.sup.3 is C.sub.4 alkyl; Z.sup.1 and Z.sup.2 are independently one of hydroxy, alkoxy, or aryloxy, or together Z.sup.1 and Z.sup.2 form a moiety derived from a dihydroxy compound having at least two hydroxy groups separated by at least two connecting atoms in a chain or ring, said chain or ring comprising carbon atoms and, optionally, a heteroatom or heteroatoms which can be N, S, or O.

7. The compound of claim 6, wherein P is R.sup.7 --C(O)--, and R.sup.7 is quinolinyl, pyrazinyl, pyridyl, quinoxalinyl or N-morpholinyl.

8. The compound of claim 6, wherein R.sup.3 is isobutyl.

9. The compound of claim 6, wherein Z.sup.1 and Z.sup.2 are independently one of hydroxy, C.sub.1-6 alkoxy, or C.sub.6-10 aryloxy.

10. The compound of claim 6, wherein Z.sup.1 and Z.sup.2 are both hydroxy.

11. The compound of claim 6, wherein R.sup.5 is C.sub.6-10 aryl.

12. A compound having the formula: ##STR54##

or a pharmaceutically acceptable salt thereof, wherein: P is R.sup.7 --C(O)-- and R.sup.7 is pyrazinyl; A is 1; B.sup.1 is CH; X.sup.1 is --C(O)--NH--; X.sup.2 is --C(O)--NH--; R is hydrogen or alkyl; R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, heterocycle, and --CH.sub.2 --R.sup.5, where R.sup.5, in each instance, is one of aryl, aralkyl, alkaryl, cycloalkyl, or --W--R.sup.6, where W is a chalcogen and R.sup.6 is alkyl; where the ring portion of any of said aryl, aralkyl, or alkaryl in R.sup.1, R.sup.2 and R.sup.5 can be optionally substituted by one or two substitutes independently selected from the group consisting of C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.1-6 alkyl(C.sub.3-8)cycloalkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, cyano, amino, C.sub.1-6 alkylamino, di(C.sub.1-6)alkylamino, benzylamino, dibenzylamino, nitro, carboxy, carbo(C.sub.1-6)alkoxy, trifluoromethyl, halogen, C.sub.1-6 alkoxy, C.sub.6-10 aryl, C.sub.6-10 aryl(C.sub.1-6)alkyl, C.sub.6-10 aryl(C.sub.1-6)alkoxy, hydroxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfinyl, C.sub.1-6 alkylsulfonyl, C.sub.6-10 arylthio, C.sub.6-10 arylsulfinyl, C.sub.6-10 arylsulfonyl, C.sub.6-10 aryl C.sub.1-6 alkyl(C.sub.6-10)aryl, and halo(C.sub.6-10)aryl; R.sup.3 is C.sub.4 alkyl; Z.sup.1 and Z.sup.2 are independently one of hydroxy, alkoxy, or aryloxy, or together Z.sup.1 and Z.sup.2 form a moiety derived from a dihydroxy compound having at least two hydroxy groups separated by at least two connecting atoms in a chain or ring, said chain or ring comprising carbon atoms and, optionally, a heteroatom or heteroatoms which can be N, S, or O.

13. A compound having the formula: ##STR55##

or a pharmaceutically acceptable salt thereof, wherein: P is R.sup.7 --C(O)-- or R.sup.7 --SO.sub.2 --, and R.sup.7 is heteroaryl or a saturated or partially unsaturated heterocycle; A is 1; B.sup.1 is CH; X.sup.1 is --C(O)--NH--; X.sup.2 is --C(O)--NH--; R is hydrogen; R.sup.1 --CH.sub.2 --R.sup.5, where R.sup.5 is C.sub.6-10 aryl; R.sup.2 is benzyl; R.sup.3 is C.sub.4 alkyl; and Z.sup.1 and Z.sup.2 are independently one of hydroxy, alkoxy, or aryloxy, or together Z.sup.1 and Z.sup.2 form a moiety derived from a dihydroxy compound having at least two hydroxy groups separated by at least two connecting atoms in a chain or ring, said chain or ring comprising carbon atoms and, optionally, a heteroatom or heteroatoms which can be N, S, or O.

14. The compound of claim 13, wherein P is R.sup.7 --C(O)--, and R.sup.7 is quinolinyl, pyrazinyl, pyridyl, quinoxalinyl or N-morpholinyl.

15. The compound of claim 13, wherein P is 2-pyrazinecarbonyl.

16. The compound of claim 13, wherein R.sup.3 is isobutyl.

17. The compound of claim 13, wherein R.sup.5 is phenyl.

18. The compound of claim 13, wherein Z.sup.1 and Z.sup.2 are both hydroxy.

19. A compound having the formula: ##STR56##

or a pharmaceutically acceptable salt thereof, wherein: P is 2-pyrazinecarbonyl; A is 1; B.sup.1 is CH; X.sup.1 is --C(O)--NH--; X.sup.2 is --C(O)--NH--; R is hydrogen; R.sup.1 is --CH.sub.2 --R.sup.5, where R.sup.5 is phenyl; R.sup.2 is benzyl; R.sup.3 is isobutyl; and Z.sup.1 and Z.sup.2 are both hydroxy.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

How are People Using DrugPatentWatch?

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

`abc