CA2492060A1 - Carvedilol phosphate salts and/or solvates thereof, corresponding compositions, and/or methods of treatment - Google Patents

Carvedilol phosphate salts and/or solvates thereof, corresponding compositions, and/or methods of treatment Download PDF

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Publication number
CA2492060A1
CA2492060A1 CA002492060A CA2492060A CA2492060A1 CA 2492060 A1 CA2492060 A1 CA 2492060A1 CA 002492060 A CA002492060 A CA 002492060A CA 2492060 A CA2492060 A CA 2492060A CA 2492060 A1 CA2492060 A1 CA 2492060A1
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CA
Canada
Prior art keywords
theta
compound according
degrees
characteristic peaks
angina
Prior art date
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Granted
Application number
CA002492060A
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French (fr)
Other versions
CA2492060C (en
Inventor
Christopher S. Brook
Wei Chen
Philip C. Dell'orco
Lee M. Katrincic
Ann Marie Louvet
Choon K. Oh
Paul G. Spoors
Christopher Werner
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SmithKline Beecham Cork Ltd
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Individual
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Application filed by Individual filed Critical Individual
Publication of CA2492060A1 publication Critical patent/CA2492060A1/en
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Publication of CA2492060C publication Critical patent/CA2492060C/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Abstract

The present invention relates to carvedilol phosphate salts, which include novel crystalline forms of carvedilol dihydrogen phosphate (i.e., dihydrogen phosphate salt of 1-(carbazol-4-yloxy-3-[[2-(o-methoxyphenoxy) ethyl]amino]- 2- propanol) and/or carvedilol hydrogen phosphate, etc.), and/or solvates thereof, compositions containing the aforementioned salts and/or solvates, a nd methods of using the aforementioned salts and/or solvates to treat hypertension, congestive heart failure and angina, etc.

Claims (31)

1. A compound which is crystalline carvedilol dihydrogen phosphate hemihydrate.
2. The compound according to claim 1 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta as shown in Figure 1.
3. The compound according to claim 2 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (2.theta.) at about 7.0 ~
0.2 (2.theta.), 11.4 ~ 0.2 (2.theta.), 15.9 ~ 0.2 (2.theta.), 18.8 ~ 0.2 (2.theta.), 20.6 ~ 0.2 (2.theta.), 22.8 ~
0.2 (2.theta.), and 25.4 ~ 0.2 (2.theta.).
4. The compound according to claim 1 having an infrared spectrum which comprises characteristic absortion bands expressed in wave numbers as shown in Figure 6.
5. The compound according to claim 1 having a Raman spectrum which comprises characteristic peaks as shown in Figure 3.
6. A compound which is carvedilol dihydrogen phosphate dehydrate.
7. The compound according to claim 6 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta (2.theta.) as shown in Figure 9.
8. The compound according to claim 7 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (2.theta.) at about 6.5 ~
0.2 (2.theta.), 7.1 ~ 0.2 (2.theta.), 13.5 ~ 0.2 (2.theta.), 14.0 ~ 0.2 (2.theta.), 17.8 ~ 0.2 (2.theta.), 18.9 ~
0.2 (2.theta.), and 21.0 ~ 0.2 (2.theta.).
9. The compound according to claim 6 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta (2.theta.) as shown in Figure 25.
10. The compound according to claim 9 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (28) at about 6.4 ~
0.2 (2.theta.), 9.6 ~ 0.2 (2.theta.), 16.0 ~ 0.2 (2.theta.), 18.4 ~ 0.2 (2.theta.), 20.7 ~ 0.2 (2.theta.), and 24.5 ~ 0.2 (2.theta.).
11. A compound which is carvedilol dihydrogen phosphate methanol solvate.
12. The compound according to claim 11 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta (2.theta.) as shown in Figure 24.
13. The compound according to claim 12 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (2.theta.) at about 6.9 ~
0.2 (2.theta.), 7.2 ~ 0.2 (2.theta.), 13.5 ~ 0.2 (2.theta.), 14.1 ~ 0.2 (2.theta.), 17.8 ~ 0.2 (2.theta.), and 34.0 ~ 0.2 (2.theta.).
14. A compound which is carvedilol dihydrogen phosphate.
15. The compound according to claim 14 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta (2.theta.) as shown in Figure 28.
16. The compound according to claim 15 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (2.theta.) at about 13.2 ~
0.2 (2.theta.), 15.8 ~ 0.2 (2.theta.), 16.3 ~ 0.2 (2.theta.), 21.2 ~ 0.2 (2.theta.), 23.7 ~ 0.2 (2.theta.), and 26.0 ~ 0.2 (2.theta.).
17. A compound which is carvedilol hydrogen phosphate.
18. The compound according to claim 17 having an x-ray diffraction pattern which comprises characteristic peaks in degrees two-theta (28) as shown in Figure 29.
19. The compound according to claim 18 having characteristic peaks from 0° degrees 2-theta (2.theta.) to 35° degrees 2-theta (2A) at about 5.5 ~
0.2 (2.theta.), 12.3 ~ 0.2 (2.theta.), 15.3 ~ 0.2 (2.theta.), 19.5 ~ 0.2 (2.theta.), 21.6 ~ 0.2 (2.theta.), and 24.9 ~ 0.2 (2.theta.).
20. A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.
21. A pharmaceutical composition comprising the compound according to claim 6 and a pharmaceutically acceptable carrier.
22. A pharmaceutical composition comprising the compound according to claim 14 and a pharmaceutically acceptable carrier.
23. A pharmaceutical composition comprising the compound according to claim 17 and a pharmaceutically acceptable carrier.
24. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the compound according to claim 1.
25. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the compound according to claim 6.
26. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the compound according to claim 14.
27. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the compound according to claim 17.
28. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the composition according to claim 20.
29. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the composition according to claim 21.
30. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the composition according to claim 22.
31. A method of treating hypertension, congestive heart failure or angina which comprises administering to a subject in need thereof an effective amount of the composition according to claim 23.
CA2492060A 2002-06-27 2003-06-27 Carvedilol phosphate salts and/or solvates thereof, corresponding compositions, and/or methods of treatment Expired - Lifetime CA2492060C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US39217502P 2002-06-27 2002-06-27
US60/392,175 2002-06-27
PCT/US2003/020408 WO2004002419A2 (en) 2002-06-27 2003-06-27 Carvedilol phosphate salts and/or solvates thereof, correspondinq compositions, and/or methods of treatment

Publications (2)

Publication Number Publication Date
CA2492060A1 true CA2492060A1 (en) 2004-01-08
CA2492060C CA2492060C (en) 2011-11-01

Family

ID=30000823

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2492060A Expired - Lifetime CA2492060C (en) 2002-06-27 2003-06-27 Carvedilol phosphate salts and/or solvates thereof, corresponding compositions, and/or methods of treatment

Country Status (15)

Country Link
US (6) US7268156B2 (en)
EP (1) EP1534270A4 (en)
JP (3) JP2005533823A (en)
KR (3) KR101468827B1 (en)
CN (6) CN103333099A (en)
AU (1) AU2003248746B2 (en)
BR (1) BR0312102A (en)
CA (1) CA2492060C (en)
EA (1) EA008384B1 (en)
IL (1) IL165814A (en)
MX (1) MXPA04012923A (en)
NO (1) NO329710B1 (en)
NZ (1) NZ537161A (en)
WO (1) WO2004002419A2 (en)
ZA (1) ZA200410011B (en)

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US7268156B2 (en) 2007-09-11
US20070244181A1 (en) 2007-10-18
AU2003248746B2 (en) 2009-01-08
CN1678305A (en) 2005-10-05
US7626041B2 (en) 2009-12-01
WO2004002419A2 (en) 2004-01-08
CN103288715A (en) 2013-09-11
IL165814A0 (en) 2006-01-15
NZ537161A (en) 2007-09-28
NO20050427L (en) 2005-01-25
CN103288714A (en) 2013-09-11
JP2005533823A (en) 2005-11-10
CN101898995A (en) 2010-12-01
CN101898995B (en) 2013-05-01
US7902378B2 (en) 2011-03-08
EA008384B1 (en) 2007-04-27
US7759384B2 (en) 2010-07-20
ZA200410011B (en) 2006-07-26
EP1534270A4 (en) 2006-05-17
US20070259940A1 (en) 2007-11-08
US20070244182A1 (en) 2007-10-18
BR0312102A (en) 2007-05-29
IL165814A (en) 2012-05-31
AU2003248746A1 (en) 2004-01-19
CN103333099A (en) 2013-10-02
KR101468827B1 (en) 2014-12-03
CA2492060C (en) 2011-11-01
EA200500091A1 (en) 2005-10-27
KR20110134952A (en) 2011-12-15
NO329710B1 (en) 2010-12-06
US20080262069A1 (en) 2008-10-23
WO2004002419A3 (en) 2004-06-03
US20070238774A1 (en) 2007-10-11
US7893100B2 (en) 2011-02-22
EP1534270A2 (en) 2005-06-01
KR20140006111A (en) 2014-01-15
MXPA04012923A (en) 2005-03-31
CN103254114A (en) 2013-08-21
KR20130042047A (en) 2013-04-25
JP2011088917A (en) 2011-05-06
US20050240027A1 (en) 2005-10-27
JP5422545B2 (en) 2014-02-19
JP2013241450A (en) 2013-12-05

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