NO313588B1 - Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den - Google Patents

Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den Download PDF

Info

Publication number: NO313588B1
Authority: NO; Norway
Prior art keywords: carbazolyloxy; ethylamino; propanol; carvedilol; methoxyphenoxy
Prior art date: 1997-07-22

Application number

NO20000301A

Other languages

English (en)

Norwegian (no)

Other versions

NO20000301L (no

NO20000301D0 (no

Inventor

Erhard Reinholz

Peter Beyer

Original Assignee

Roche Diagnostics Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-07-22

Filing date

2000-01-21

Publication date

2002-10-28

2000-01-21 Application filed by Roche Diagnostics Gmbh filed Critical Roche Diagnostics Gmbh

2000-01-21 Publication of NO20000301L publication Critical patent/NO20000301L/no

2000-01-21 Publication of NO20000301D0 publication Critical patent/NO20000301D0/no

2002-10-28 Publication of NO313588B1 publication Critical patent/NO313588B1/no

Links

OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 title claims abstract description 24
238000000034 method Methods 0.000 title claims abstract description 14
238000012986 modification Methods 0.000 title claims abstract description 12
230000004048 modification Effects 0.000 title claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 title abstract description 9
238000002360 preparation method Methods 0.000 title abstract description 7
229960004195 carvedilol Drugs 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 11
238000002844 melting Methods 0.000 claims description 11
230000008018 melting Effects 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
238000002329 infrared spectrum Methods 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
208000019622 heart disease Diseases 0.000 claims description 3
229910016523 CuKa Inorganic materials 0.000 claims description 2
238000002441 X-ray diffraction Methods 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
230000005855 radiation Effects 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
230000008707 rearrangement Effects 0.000 claims 1
238000006462 rearrangement reaction Methods 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000000113 differential scanning calorimetry Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
108010010803 Gelatin Chemical class 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
238000001237 Raman spectrum Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000004927 fusion Effects 0.000 description 2
239000008273 gelatin Chemical class 0.000 description 2
229920000159 gelatin Chemical class 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
238000000634 powder X-ray diffraction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
238000002050 diffraction method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
-1 gums Polymers 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
230000010287 polarization Effects 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229940068984 polyvinyl alcohol Drugs 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

NO20000301A 1997-07-22 2000-01-21 Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den NO313588B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP97112491A EP0893440A1 (en)	1997-07-22	1997-07-22	Thermodynamically stable modification of 1-(4-carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it
PCT/EP1998/004475 WO1999005105A1 (en)	1997-07-22	1998-07-18	Thermodynamically stable modification of 1-(4-carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it

Publications (3)

Publication Number	Publication Date
NO20000301L NO20000301L (no)	2000-01-21
NO20000301D0 NO20000301D0 (no)	2000-01-21
NO313588B1 true NO313588B1 (no)	2002-10-28

Family

ID=8227094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20000301A NO313588B1 (no)	1997-07-22	2000-01-21	Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den

Country Status (31)

Country	Link
EP (2)	EP0893440A1 (cs)
JP (1)	JP2001510824A (cs)
KR (1)	KR100336229B1 (cs)
CN (1)	CN1125047C (cs)
AR (1)	AR015133A1 (cs)
AT (1)	ATE236123T1 (cs)
AU (1)	AU740453B2 (cs)
BR (1)	BR9810776A (cs)
CA (1)	CA2296637C (cs)
CZ (1)	CZ296947B6 (cs)
DE (1)	DE69812964T2 (cs)
DK (1)	DK1000027T3 (cs)
ES (1)	ES2195366T3 (cs)
HR (1)	HRP980406A2 (cs)
HU (1)	HUP0003198A3 (cs)
IL (1)	IL133677A (cs)
MA (1)	MA26523A1 (cs)
MY (1)	MY117734A (cs)
NO (1)	NO313588B1 (cs)
NZ (1)	NZ502136A (cs)
PE (1)	PE96999A1 (cs)
PL (1)	PL191602B1 (cs)
PT (1)	PT1000027E (cs)
RU (1)	RU2202542C2 (cs)
SI (1)	SI1000027T1 (cs)
TR (1)	TR200000148T2 (cs)
TW (1)	TW505631B (cs)
UY (1)	UY25108A1 (cs)
WO (1)	WO1999005105A1 (cs)
YU (1)	YU2200A (cs)
ZA (1)	ZA986475B (cs)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001074356A1 (en) *	2000-04-03	2001-10-11	F. Hoffmann-La Roche Ag	Concentrated solutions of carvedilol
CA2413702A1 (en)	2000-06-28	2002-01-03	Teva Pharmaceuticals Industries Ltd.	Carvedilol
EP1655285A1 (en) *	2000-06-28	2006-05-10	Teva Pharmaceutical Industries Ltd.	Method for preparation of a crystalline form of carvedilol (form II)
WO2003005970A2 (en) *	2001-07-13	2003-01-23	Smithkline Beecham Corporation	Carvedilol polymorph
US20050019399A1 (en)	2001-09-21	2005-01-27	Gina Fischer	Controlled release solid dispersions
PL370412A1 (en) *	2001-09-28	2005-05-30	F.Hoffmann-La Roche Ag	Pseudopolymorphic forms of carvedilol
US6710184B2 (en) *	2002-01-15	2004-03-23	Teva Pharmaceutical Industries Ltd.	Crystalline solids of carvedilol and processes for their preparation
JP2006500320A (ja) *	2002-04-30	2006-01-05	エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド	カルベジロール一クエン酸塩一水和物
CA2492084A1 (en) *	2002-06-27	2004-01-08	Sb Pharmco Puerto Rico Inc.	Carvedilol hydobromide
BR0312102A (pt)	2002-06-27	2007-05-29	Sb Pharmco Inc	sais de fosfato de carvedilol e/ou seus solvatos, composições correspondentes, e/ou métodos de tratamento
WO2004041252A1 (en) *	2002-11-08	2004-05-21	Egalet A/S	Controlled release carvedilol compositions
US8877241B2 (en)	2003-03-26	2014-11-04	Egalet Ltd.	Morphine controlled release system
WO2004094378A1 (en) *	2003-04-21	2004-11-04	Matrix Laboratories Ltd	Process for the preparation of carvedilol form-ii
SI21616A (sl) *	2003-09-02	2005-04-30	Krka, Tovarna Zdravil, D.D., Novo Mesto	Nove kristalne oblike karvedilola
JP2007512372A (ja) *	2003-11-25	2007-05-17	エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド	カルベジロール塩、対応する組成物、送達および／または治療方法
CA2589699A1 (en) *	2004-12-09	2006-06-15	Zach System S.P.A.	Process for the preparation of carvedilol and its enantiomers
EP1781611A1 (en) *	2005-06-09	2007-05-09	Teva Pharmaceutical Industries Ltd.	Crystalline forms of carvedilol and processes for their preparation
WO2008002683A2 (en)	2006-06-28	2008-01-03	Teva Pharmaceutical Industries Ltd.	Polymorphous forms of carvedilol phosphate
RU2366653C2 (ru) *	2006-07-03	2009-09-10	Ооо "Нанокриохимия"	Способ получения рентгеноаморфной модификации карведилола
US20080249317A1 (en) *	2007-04-04	2008-10-09	Apotex Inc.	Novel amorphous form of carvedilol phosphate and processes for the preparation thereof
US8821928B2 (en)	2007-06-04	2014-09-02	Egalet Ltd.	Controlled release pharmaceutical compositions for prolonged effect
NZ594207A (en)	2009-02-06	2013-03-28	Egalet Ltd	Immediate release composition resistant to abuse by intake of alcohol
AU2010265213B2 (en)	2009-06-24	2012-08-23	Egalet Ltd.	Controlled release formulations

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2815926A1 (de) *	1978-04-13	1979-10-18	Boehringer Mannheim Gmbh	Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2805404A1 (de) *	1978-02-09	1979-08-16	Merck Patent Gmbh	1-aryloxy-3-nitratoalkylamino-2-propanole und verfahren zu ihrer herstellung
DE3319027A1 (de) *	1983-05-26	1984-11-29	Boehringer Mannheim Gmbh, 6800 Mannheim	Verfahren zur herstellung von optisch aktiven carbazol-derivaten, neue r- und s-carbazol-derivate, sowie arzneimittel, die diese verbindungen enthalten

1997
- 1997-07-22 EP EP97112491A patent/EP0893440A1/en not_active Withdrawn
1998
- 1998-07-15 MY MYPI98003245A patent/MY117734A/en unknown
- 1998-07-15 PE PE1998000626A patent/PE96999A1/es not_active Application Discontinuation
- 1998-07-18 AU AU86319/98A patent/AU740453B2/en not_active Ceased
- 1998-07-18 ES ES98937576T patent/ES2195366T3/es not_active Expired - Lifetime
- 1998-07-18 JP JP2000504104A patent/JP2001510824A/ja active Pending
- 1998-07-18 WO PCT/EP1998/004475 patent/WO1999005105A1/en not_active Ceased
- 1998-07-18 TR TR2000/00148T patent/TR200000148T2/xx unknown
- 1998-07-18 AT AT98937576T patent/ATE236123T1/de not_active IP Right Cessation
- 1998-07-18 CZ CZ20000221A patent/CZ296947B6/cs not_active IP Right Cessation
- 1998-07-18 SI SI9830442T patent/SI1000027T1/xx unknown
- 1998-07-18 CN CN98807436A patent/CN1125047C/zh not_active Expired - Fee Related
- 1998-07-18 NZ NZ502136A patent/NZ502136A/en unknown
- 1998-07-18 PL PL338432A patent/PL191602B1/pl unknown
- 1998-07-18 YU YU2200A patent/YU2200A/sh unknown
- 1998-07-18 CA CA002296637A patent/CA2296637C/en not_active Expired - Fee Related
- 1998-07-18 DK DK98937576T patent/DK1000027T3/da active
- 1998-07-18 TW TW087111738A patent/TW505631B/zh not_active IP Right Cessation
- 1998-07-18 IL IL13367798A patent/IL133677A/en not_active IP Right Cessation
- 1998-07-18 KR KR1020007000667A patent/KR100336229B1/ko not_active Expired - Fee Related
- 1998-07-18 RU RU2000103033/04A patent/RU2202542C2/ru not_active IP Right Cessation
- 1998-07-18 HU HU0003198A patent/HUP0003198A3/hu unknown
- 1998-07-18 BR BR9810776-3A patent/BR9810776A/pt not_active Application Discontinuation
- 1998-07-18 DE DE69812964T patent/DE69812964T2/de not_active Expired - Fee Related
- 1998-07-18 EP EP98937576A patent/EP1000027B1/en not_active Expired - Lifetime
- 1998-07-18 PT PT98937576T patent/PT1000027E/pt unknown
- 1998-07-20 MA MA25178A patent/MA26523A1/fr unknown
- 1998-07-21 AR ARP980103547A patent/AR015133A1/es unknown
- 1998-07-21 ZA ZA9806475A patent/ZA986475B/xx unknown
- 1998-07-22 UY UY25108A patent/UY25108A1/es not_active IP Right Cessation
- 1998-07-22 HR HR97112491.2A patent/HRP980406A2/hr not_active Application Discontinuation
2000
- 2000-01-21 NO NO20000301A patent/NO313588B1/no unknown

Also Published As

Publication number	Publication date
HUP0003198A3 (en)	2002-10-28
KR100336229B1 (ko)	2002-05-09
CN1264366A (zh)	2000-08-23
TR200000148T2 (tr)	2000-07-21
HRP980406A2 (en)	1999-04-30
DK1000027T3 (da)	2003-07-21
NO20000301L (no)	2000-01-21
EP0893440A1 (en)	1999-01-27
NZ502136A (en)	2002-05-31
SI1000027T1 (en)	2003-10-31
DE69812964D1 (de)	2003-05-08
YU2200A (sh)	2002-03-18
ZA986475B (en)	2000-01-21
PL338432A1 (en)	2000-11-06
PT1000027E (pt)	2003-07-31
WO1999005105A1 (en)	1999-02-04
JP2001510824A (ja)	2001-08-07
MY117734A (en)	2004-07-31
CA2296637A1 (en)	1999-02-04
IL133677A0 (en)	2001-04-30
AR015133A1 (es)	2001-04-18
CZ2000221A3 (cs)	2000-05-17
DE69812964T2 (de)	2004-03-04
UY25108A1 (es)	2000-12-29
AU740453B2 (en)	2001-11-01
AU8631998A (en)	1999-02-16
HUP0003198A2 (en)	2001-03-28
PE96999A1 (es)	1999-10-12
RU2202542C2 (ru)	2003-04-20
EP1000027A1 (en)	2000-05-17
NO20000301D0 (no)	2000-01-21
TW505631B (en)	2002-10-11
CN1125047C (zh)	2003-10-22
KR20010022097A (ko)	2001-03-15
CZ296947B6 (cs)	2006-08-16
IL133677A (en)	2004-06-01
EP1000027B1 (en)	2003-04-02
ATE236123T1 (de)	2003-04-15
CA2296637C (en)	2005-11-15
ES2195366T3 (es)	2003-12-01
PL191602B1 (pl)	2006-06-30
HK1029339A1 (en)	2001-03-30
MA26523A1 (fr)	2004-12-20
BR9810776A (pt)	2000-09-19

Publication	Publication Date	Title
US6730326B2 (en)	2004-05-04	Thermodynamically stable modification of 1-(4-carbazolyl-oxy-3[2-(2-methoxyphenoxy)-ethylamino]-2-propanol process for its preparation and pharmaceutical compositions containing it
EP1000027B1 (en)	2003-04-02	Thermodynamically stable modification of 1-(4-carbazolyloxy)-3- 2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it
KR102442536B1 (ko)	2022-09-13	리나글립틴 결정형 및 이의 제조방법
KR20090048364A (ko)	2009-05-13	아고멜라틴의 결정형 ⅵ, 이의 제조 방법 및 이를 함유하는약제학적 조성물
KR20040077872A (ko)	2004-09-07	카베디롤의 결정질 고체 및 그 제조 방법
JP7168447B2 (ja)	2022-11-09	ビラスチンの結晶形態及びそれらの調製方法
TWI819279B (zh)	2023-10-21	2-[(4s)-8-氟-2-[4-(3-甲氧基苯基)哌嗪-1-基]-3-[2-甲氧基-5-(三氟甲基)苯基]-4h-喹唑啉-4-基]乙酸之鉀鹽
US7981897B2 (en)	2011-07-19	Crystal form of (3-cyano-1H-Indo1-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone, hydrochloride
JPH09110830A (ja)	1997-04-28	Ｎ−メチル−ｎ−［（１ｓ）−１−フェニル−２−｛（３ｓ）−３−ヒドロキシピロリジン−１−イル｝エチル］−２，２−ジフェニルアセトアミド
WO2012055163A1 (zh)	2012-05-03	来曲唑i型结晶及其制备方法
US6316672B1 (en)	2001-11-13	Form a of fluoxetine hydrochloride
JPS6219577A (ja)	1987-01-28	新規なベンジルピペラジン誘導体および該化合物を有効成分とする医薬組成物
JP2005539010A (ja)	2005-12-22	デスロラタジンヘミフマレートの新規な塩及び多形体
HU210879A9 (en)	1995-09-28	Pharmaceutical agents
KR101132949B1 (ko)	2012-04-10	베포타스틴 살리실산염, 이의 제조방법 및 이를 유효성분으로 포함하는 항히스타민 또는 항알레르기용 약학적 조성물
MXPA00000507A (en)	2001-05-07	Thermodynamically stable modification of 1-(4-carbazolyloxy)-3- [2-(2-methoxyphenoxy)ethylamino]-2- propanole, process for its preparation and pharmaceutical compositions containing it
US6310250B1 (en)	2001-10-30	Form A of fluoxetine hydrochloride
RU2772222C2 (ru)	2022-05-18	Кристаллические формы биластина и способы их получения
US6310251B1 (en)	2001-10-30	Form a of fluoxetine hydrochloride
HK1029339B (en)	2004-02-13	Thermodynamically stable modification of 1-(4-carbazoly-loxy)-3-(2-(2-methoxyphenoxy)ethylamino)-2-propanole, process for its preparation and pharmaceutical compositions containing it
JP2013507420A (ja)	2013-03-04	パルドプルノックスの多形