NO327638B1 - Krystallpolymorfisme av aminoetylfenoksyeddiksyre derivater - Google Patents

Krystallpolymorfisme av aminoetylfenoksyeddiksyre derivater Download PDF

Info

Publication number: NO327638B1
Authority: NO; Norway
Prior art keywords: ethyl; phenoxy; hydroxy; amino; hydroxyphenyl
Prior art date: 1999-01-21

Application number

NO20013537A

Other languages

English (en)

Norwegian (no)

Other versions

NO20013537D0 (no

NO20013537L (no

Inventor

Tetsuro Tamai

Nobuyuki Tanaka

Michio Toda

Kiyoshi Kasai

Junichi Sonehara

Eiji Tsuru

Original Assignee

Kissei Pharmaceutical Company

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.)

1999-01-21

Filing date

2001-07-17

Publication date

2009-09-07

2001-07-17 Application filed by Kissei Pharmaceutical Company filed Critical Kissei Pharmaceutical Company

2001-07-17 Publication of NO20013537D0 publication Critical patent/NO20013537D0/no

2001-09-18 Publication of NO20013537L publication Critical patent/NO20013537L/no

2009-09-07 Publication of NO327638B1 publication Critical patent/NO327638B1/no

Links

239000013078 crystal Substances 0.000 title description 11
FZBSFRTYISUPFO-UHFFFAOYSA-N 4-amino-2-phenoxybutanoic acid Chemical class NCCC(C(O)=O)OC1=CC=CC=C1 FZBSFRTYISUPFO-UHFFFAOYSA-N 0.000 title description 3
KKXPBQQLKHBRDA-DJJJIMSYSA-N 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetic acid Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(OCC(O)=O)C=C1 KKXPBQQLKHBRDA-DJJJIMSYSA-N 0.000 claims description 22
238000000634 powder X-ray diffraction Methods 0.000 claims description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003814 drug Substances 0.000 description 15
229940079593 drug Drugs 0.000 description 15
239000000243 solution Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000203 mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000001914 filtration Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012046 mixed solvent Substances 0.000 description 6
238000000034 method Methods 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000008602 contraction Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
QVFAFFSUDCLVCA-UHFFFAOYSA-N ethyl 2-[4-(2-hydroxyethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(CCO)C=C1 QVFAFFSUDCLVCA-UHFFFAOYSA-N 0.000 description 3
YVGDLZULUJKFPY-UHFFFAOYSA-N ethyl 2-[4-(2-methylsulfonyloxyethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(CCOS(C)(=O)=O)C=C1 YVGDLZULUJKFPY-UHFFFAOYSA-N 0.000 description 3
BNUXUQJQIOSXIJ-NVJCMEIXSA-N ethyl 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenoxy]acetate;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC(OCC(=O)OCC)=CC=C1CCN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 BNUXUQJQIOSXIJ-NVJCMEIXSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
108060003345 Adrenergic Receptor Proteins 0.000 description 2
102000017910 Adrenergic receptor Human genes 0.000 description 2
206010007027 Calculus urinary Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
210000000626 ureter Anatomy 0.000 description 2
208000008281 urolithiasis Diseases 0.000 description 2
JAYBQRKXEFDRER-RCOVLWMOSA-N 4-Hydroxynorephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=C(O)C=C1 JAYBQRKXEFDRER-RCOVLWMOSA-N 0.000 description 1
229910016523 CuKa Inorganic materials 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
241000282339 Mustela Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
239000012891 Ringer solution Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
IZQZNLBFNMTRMF-UHFFFAOYSA-N acetic acid;phosphoric acid Chemical compound CC(O)=O.OP(O)(O)=O IZQZNLBFNMTRMF-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
PEZBJHXXIFFJBI-UHFFFAOYSA-N ethanol;phosphoric acid Chemical compound CCO.OP(O)(O)=O PEZBJHXXIFFJBI-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
210000000754 myometrium Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO20013537A 1999-01-21 2001-07-17 Krystallpolymorfisme av aminoetylfenoksyeddiksyre derivater NO327638B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1363999		1999-01-21
PCT/JP2000/000168 WO2000043350A1 (fr)	1999-01-21	2000-01-17	Polymorphisme cristallin de derive d'acide aminoethylphenoxyacetique

Publications (3)

Publication Number	Publication Date
NO20013537D0 NO20013537D0 (no)	2001-07-17
NO20013537L NO20013537L (no)	2001-09-18
NO327638B1 true NO327638B1 (no)	2009-09-07

Family

ID=11838822

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20013537A NO327638B1 (no)	1999-01-21	2001-07-17	Krystallpolymorfisme av aminoetylfenoksyeddiksyre derivater

Country Status (23)

Country	Link
US (1)	US6376707B1 (de)
EP (1)	EP1146035B1 (de)
JP (1)	JP4005771B2 (de)
KR (1)	KR100604712B1 (de)
CN (1)	CN1216855C (de)
AR (1)	AR022319A1 (de)
AT (1)	ATE309978T1 (de)
AU (1)	AU778091B2 (de)
CA (1)	CA2359061C (de)
CO (1)	CO5160240A1 (de)
CZ (1)	CZ302572B6 (de)
DE (1)	DE60024053T2 (de)
DK (1)	DK1146035T3 (de)
ES (1)	ES2251956T3 (de)
IL (1)	IL144253A (de)
MY (1)	MY119093A (de)
NO (1)	NO327638B1 (de)
NZ (1)	NZ512965A (de)
PE (1)	PE20001398A1 (de)
RU (1)	RU2237656C2 (de)
TW (1)	TWI223647B (de)
WO (1)	WO2000043350A1 (de)
ZA (1)	ZA200105830B (de)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998013333A1 (fr) *	1996-09-26	1998-04-02	Kissei Pharmaceutical Co., Ltd.	Derives de 2-amino-1-(4-hydroxy-2-methylphenyl)propanol
ID24062A (id) *	1997-07-25	2000-07-06	Kissei Pharmaceutical	Turunan-turunan asam aminoetilfenoksiasetat dan obat untuk mengurangi nyeri dan membantu penyingkiran dalam litiasis saluran air kencing
NZ507486A (en) *	1998-04-14	2003-03-28	Kissei Pharmaceutical	2-methylpropionic acid derivatives and pharmaceutical uses thereof

2000
- 2000-01-17 EP EP00900407A patent/EP1146035B1/de not_active Expired - Lifetime
- 2000-01-17 US US09/889,857 patent/US6376707B1/en not_active Expired - Fee Related
- 2000-01-17 AU AU20047/00A patent/AU778091B2/en not_active Ceased
- 2000-01-17 ES ES00900407T patent/ES2251956T3/es not_active Expired - Lifetime
- 2000-01-17 NZ NZ512965A patent/NZ512965A/xx not_active IP Right Cessation
- 2000-01-17 CZ CZ20012621A patent/CZ302572B6/cs not_active IP Right Cessation
- 2000-01-17 AT AT00900407T patent/ATE309978T1/de active
- 2000-01-17 WO PCT/JP2000/000168 patent/WO2000043350A1/ja active IP Right Grant
- 2000-01-17 KR KR1020017009176A patent/KR100604712B1/ko not_active IP Right Cessation
- 2000-01-17 PE PE2000000030A patent/PE20001398A1/es not_active Application Discontinuation
- 2000-01-17 DK DK00900407T patent/DK1146035T3/da active
- 2000-01-17 CN CN008030251A patent/CN1216855C/zh not_active Expired - Fee Related
- 2000-01-17 RU RU2001120343A patent/RU2237656C2/ru not_active IP Right Cessation
- 2000-01-17 JP JP2000594768A patent/JP4005771B2/ja not_active Expired - Fee Related
- 2000-01-17 DE DE60024053T patent/DE60024053T2/de not_active Expired - Lifetime
- 2000-01-17 CA CA002359061A patent/CA2359061C/en not_active Expired - Fee Related
- 2000-01-17 IL IL14425300A patent/IL144253A/en not_active IP Right Cessation
- 2000-01-18 MY MYPI20000146A patent/MY119093A/en unknown
- 2000-01-20 CO CO00002898A patent/CO5160240A1/es unknown
- 2000-01-20 AR ARP000100247A patent/AR022319A1/es active IP Right Grant
- 2000-01-20 TW TW089100860A patent/TWI223647B/zh not_active IP Right Cessation
2001
- 2001-07-16 ZA ZA200105830A patent/ZA200105830B/xx unknown
- 2001-07-17 NO NO20013537A patent/NO327638B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AR022319A1 (es)	2002-09-04
TWI223647B (en)	2004-11-11
RU2237656C2 (ru)	2004-10-10
CZ20012621A3 (cs)	2002-02-13
AU778091B2 (en)	2004-11-18
DE60024053D1 (de)	2005-12-22
CA2359061C (en)	2004-04-06
DK1146035T3 (da)	2006-03-27
JP4005771B2 (ja)	2007-11-14
AU2004700A (en)	2000-08-07
CO5160240A1 (es)	2002-05-30
EP1146035B1 (de)	2005-11-16
CZ302572B6 (cs)	2011-07-20
MY119093A (en)	2005-03-31
EP1146035A1 (de)	2001-10-17
CN1216855C (zh)	2005-08-31
EP1146035A9 (de)	2001-12-05
NZ512965A (en)	2002-11-26
KR20010092790A (ko)	2001-10-26
NO20013537D0 (no)	2001-07-17
CN1337937A (zh)	2002-02-27
ZA200105830B (en)	2002-09-25
IL144253A0 (en)	2002-05-23
US6376707B1 (en)	2002-04-23
DE60024053T2 (de)	2006-07-20
PE20001398A1 (es)	2000-12-22
ES2251956T3 (es)	2006-05-16
KR100604712B1 (ko)	2006-07-28
NO20013537L (no)	2001-09-18
IL144253A (en)	2004-08-31
WO2000043350A1 (fr)	2000-07-27
CA2359061A1 (en)	2000-07-27
ATE309978T1 (de)	2005-12-15

Legal Events

Date	Code	Title	Description
2013-08-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US20220153700A1 (en)	2022-05-19	Salt of omecamtiv mecarbil and process for preparing salt
EA005588B1 (ru)	2005-04-28	Соли производных 3,3-дифенилпропиламинов
US8916559B2 (en)	2014-12-23	Crystalline compound of 7-[(3R)-3-amino-1-oxo-4-(2, 4, 5-trifluorophenyl)butyl]-5, 6, 7, 8-tetrahydro-3-(tri fluoromethyl)-1, 2, 4 -triazolo[4,3-A]pyrazin
TW202220962A (zh)	2022-06-01	選擇性NaV抑制劑的結晶形式及其製備方法
EP1861389A1 (de)	2007-12-05	7-(2-(4-(3-trifluormethylphenyl)-1,2,3,6-tetrahydropyrid-1-yl)ethyl)isochinolin-besylatsalz, dessen herstellung und dessen therapeutische verwendung
RU2006142768A (ru)	2008-06-10	Способ получения бисульфата атазанавира
JP2006528202A (ja)	2006-12-14	レバルブテロールヒドロクロリド多形ｂ
JP3215338B2 (ja)	2001-10-02	アミノベンゼンスルホン酸誘導体一水和物及びその製造方法
TW200900392A (en)	2009-01-01	Novel crystalline bepotastine metal salt hydrate, method for preparing same, and pharmaceutical composition comprising same
NO327638B1 (no)	2009-09-07	Krystallpolymorfisme av aminoetylfenoksyeddiksyre derivater
US11434226B2 (en)	2022-09-06	Salt and polymorph of benzopyrimidinone compound and pharmaceutical composition and use thereof
EP3398946A1 (de)	2018-11-07	Salz eines morpholinderivats und dessen kristalline form sowie herstellungsverfahren, pharmazeutische zusammensetzung und verwendung davon
OA12665A (en)	2006-06-19	New anhydrous crystalline forms of gabapentin.
KR100536750B1 (ko)	2005-12-16	시부트라민 메탄술폰산염의 결정성 반수화물을 포함하는약학 조성물
JP4005729B2 (ja)	2007-11-14	アミノエチルフェノキシ酢酸誘導体二水和物の結晶多形
JP4005731B2 (ja)	2007-11-14	アミノエチルフェノキシ酢酸誘導体の結晶多形
JP2008531510A (ja)	2008-08-14	６−ジメチルアミノメチル−１−（３−メトキシフェニル）−１，３−ジヒドロキシ−シクロヘキサン化合物のリン酸塩
KR101653816B1 (ko)	2016-09-06	결정형 사포그릴레이트 옥살산염 일수화물 또는 이의 무수물
US20110251286A1 (en)	2011-10-13	Crystalline salts and/or co-crystals of O-desmethyltramadol
WO1997001563A1 (fr)	1997-01-16	Cristaux de benzoates bicozamycine stables