DK200300221U3 - New polymorphic form of olanzapine designated Form V. - Google Patents

New polymorphic form of olanzapine designated Form V. Download PDF

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Publication number: DK200300221U3
Authority: DK; Denmark
Prior art keywords: olanzapine; distances; polymorph; diffraction pattern; typical
Prior art date: 1999-12-28

Application number

DK200300221U

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Inventor

Yusuf Khwaja Hamied

Rajendra Narayanrao Kankan

Dharmaraj Ramachandra Rao

Original Assignee

Cipla Ltd

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.)

1999-12-28

Filing date

2003-08-25

Publication date

2003-12-12

1999-12-28 Priority claimed from IN977BO1999 external-priority patent/IN187439B/en

2000-03-31 Priority claimed from US09/540,749 external-priority patent/US6348458B1/en

2003-06-16 Priority claimed from DK200300161U external-priority patent/DK200300161U3/en

2003-08-25 Application filed by Cipla Ltd filed Critical Cipla Ltd

2003-08-25 Publication of DK200300221U1 publication Critical patent/DK200300221U1/en

2003-12-12 Application granted granted Critical

2003-12-12 Publication of DK200300221U3 publication Critical patent/DK200300221U3/en

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KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 title description 45
229960005017 olanzapine Drugs 0.000 title description 45
238000000634 powder X-ray diffraction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000002441 X-ray diffraction Methods 0.000 description 6
238000000034 method Methods 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
229910016523 CuKa Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
206010017943 Gastrointestinal conditions Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

DK 2003 00221 WDK 2003 00221 W

DK 2003 00221 WDK 2003 00221 W

BRUGSMODELKRAVUTILITY MODEL REQUIREMENTS

1. Form V olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstand (Å) 10,5932 10,2170 9,9503 8,5259 7,1016 6,0731 5,2041 4,9856 4,8153 4,7514 4,5302 4,4714 4,2271 4,1307 3,9880 3,7763 3,7167 3,5315.1. Form V olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d-distance (Å) 10.5932 10.2170 9.9503 8.5259 7.1016 6.0731 5.2041 4.9856 4.8153 4, 7514 4,5302 4,4714 4,2271 4,1307 3,9880 3,7763 3,7167 3,5315.

2. Form V olanzapinpolymorf ifølge krav l, yderligere karakteriseret ved i det væsentlige følgende røntgenpulverdiffraktionsmønster, hvor d betegner de interplanare afstande, og I/Ii betegner de typiske relative intensiteter:The Form V olanzapine polymorph of claim 1, further characterized by substantially the following X-ray powder diffraction pattern, wherein d represents the interplanar distances and I / Ii represents the typical relative intensities:

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d-afstand (Å) I/I 10,5932 17 10,2170 100 9,9503 57 8,5259 22 7,1016 17 6,0731 17 5,2041 19 4,9856 20 4,8153 62 4,7514 34 4,5302 24 4,4714 51 4,2271 91 4,1307 40 3,9880 31 3,7763 10 3,7167 62 3,5315 22 2 0 3. Form V olanzapinpolymorf ifølge krav 1 eller 2, yderligere karakteriseret ved at have et infrarødt spektrum med absorbanser ved følgende bølgetal: 604 671 25 746 758 847 928 1357 30 1369.d distance (Å) I / I 10,5932 17 10,2170 100 9,9503 57 8,5259 22 7,1016 17 6,0731 17 5,2041 19 4,9856 20 4,8153 62 4,7514 34 4 The form V olanzapine polymorph according to claim 1 or 2, further characterized by having a infrared spectrum with absorbances at the following wave numbers: 604 671 25 746 758 847 928 1357 30 1369.

4. Form V olanzapinpolymorf ifølge krav 1, 2 eller 3 fremstillet ved følgende fremgangsmåde: opløsning af Form I eller Form II olanzapin iForm V olanzapine polymorph according to claim 1, 2 or 3 prepared by the following method: solution of Form I or Form II olanzapine in

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ca. 10% vandig saltsyre og præcipitering af i det væsentlige ren Form V olanzapin under anvendelse af 10% vandig natriumhydroxid, hvor Form I olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 9,9463 8,5579 8,2445 6,8862 6,3787 6,2439 5,5895 5,3055 4,9815 4,8333 4,7255 4,6286 4,533 4,4624 4,2915 4,2346 4,0855 3,8254 3,7489 3,6983 3,5817 3,5064 3,3392 3,2806 3,2138ca. 10% aqueous hydrochloric acid and precipitation of substantially pure Form V olanzapine using 10% aqueous sodium hydroxide, wherein Form I olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d distances (Å) 9.9463 8, 5579 8,2445 6,8862 6,3787 6,2439 5,5895 5,3055 4,9815 4,8333 4,7255 4,6286 4,533 4,4624 4,2915 4,2346 4,0855 3,8254 3,7489 3,6983 3,5817 3,5064 3,3392 3,2806 3,2138

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d-afstande (Å) 3,1118 3,0507 2,948 2,8172 2,7589 2,6597 2,6336 2,5956; og Form II olanzapin er en olanzapinpolymorf med et typisk røntgendiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 10,2689 8,577 7,4721 7,125 6,1459 6,071 5,4849 5,2181 5,1251 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366d distances (Å) 3.1118 3.0507 2.948 2.8172 2.7589 2.6597 2.6336 2.5956; and Form II olanzapine is an olanzapine polymorph with a typical X-ray diffraction pattern represented by the following interplanar distances: d-distances (Δ) 10.2698 8.577 7.4721 7.425 6.1459 6.071 5.4849 5.2181 5.1251 4.9874 4.7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 3,3828 3,2516 3,134 3,0848 3,0638 3,0111 2,8739 2,8102 2,7217 2,6432 2,6007.d-distances (Å) 3.3828 3.2516 3.134 3.0848 3.0638 3.0111 2.8739 2.8102 2.7217 2.6432 2.6007.

5. Form V olanzpinpolymorf ifølge krav 1, 2 eller 3 fremstillet ved følgende fremgangsmåde: opløsning af Form I eller Form II olanzapin i ca. 40% eddikesyre, og præcipitering af i det væsentlige ren Form V olanzapin under anvendelse af ca. 50% vandig natriumhydroxid, hvor Form I olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 9,9463 8,5579 8,2445 6,8862 6,3787 6,2439 5,5895 5,3055 4,9815 4,8333The Form V olanzapine polymorph according to claim 1, 2 or 3 prepared by the following method: dissolving Form I or Form II olanzapine in ca. 40% acetic acid and precipitation of substantially pure Form V olanzapine using ca. 50% aqueous sodium hydroxide, wherein Form I olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d-distances (Å) 9.9463 8.5579 8.2445 6.8862 6.3787 6.2439 5.5895 5 , 3055 4.9815 4.8333

DK 2003 00221 WDK 2003 00221 W

d-afstande (A) 4,7255 4,6286 4,533 4,4624 4,2915 4,2346 4,0855 3,8254 3,7489 3,6983 3,5817 3,5064 3,3392 3,2806 3,2138 3,1118 3,0507 2,948 2,8172 2,7589 2,6597 2,6336 2,5956; og Form II olanzapin er en olanzapinpolymorf med et typisk røntgendiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 10,2689 8,577 7,4721 7,125 6,1459d-distances (A) 4.7255 4.6286 4.533 4.4624 4.2915 4.2346 4.0855 3.8254 3.7489 3.6983 3.5817 3.5064 3.3392 3.2806 3.2138 3 , 1118 3,0507 2,948 2.8172 2.7589 2.6597 2.6336 2.5956; and Form II olanzapine is an olanzapine polymorph with a typical X-ray diffraction pattern represented by the following interplanar distances: d-distances (Å) 10.26889 8.577 7.4721 7.125 6.1459

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 6,071 5,4849 5,2181 5,1251 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366 3,3828 3,2516 3,134 3,0848 3,0638 3,0111 2,8739 2,8102 2,7217 2,6432 2,6007.d-distances (Å) 6.071 5.4849 5.2181 5.1251 4.9874 4.7665 4.7158 4.4787 4.3307 4.22294 4.141 3.9873 3.7206 3.5645 3.5366 3.3828 3,2516 3,134 3,0848 3,0638 3,0111 2,8739 2,8102 2,7217 2,6432 2,6007.

6. Form V olanzapinpolymorf ifølge krav 1, 2 eller 3 fremstillet ved følgende fremgangsmåde: opløsning af Form I eller Form II olanzapin i ca. 20% vandig myresyre, og præcipitering af i det væsentlige ren Form V olanzapin under anvendelse af ca. 35% vandig ammoni-The Form V olanzapine polymorph according to claim 1, 2 or 3 prepared by the following method: dissolving Form I or Form II olanzapine in ca. 20% aqueous formic acid, and precipitation of substantially pure Form V olanzapine using approx. 35% aqueous ammonia

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ak, hvor Form I olanzapin er en olanzapinolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: 5 d-afstande (Å) 9,9463 8,5579 8,2445 6,8862 10 6,3787 6,2439 5,5895 5,3055 4,9815 15 4,8333 4,7255 4,6286 4,533 4,4624 20 4,2915 4,2346 4,0855 3,8254 3,7489 25 3,6983 3,5817 3,5064 3,3392 3,2806 30 3,2138 3,1118 3,0507 2,948ak, where Form I olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: 5 d distances (Å) 9.9463 8.5579 8.2445 6.8862 10 6.3787 6.2439 5.5895 5, 3055 4,9815 15 4,8333 4,7255 4,6286 4,533 4,4624 20 4,2915 4,2346 4,0855 3,8254 3,7489 25 3,6983 3,5817 3,5064 3,3392 3,2806 3,2138 3,1118 3,0507 2,948

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 2,8172 2,7589 2,6597 2,6336 2,5956,- og Form II olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 10,2689 8,577 7,4721 7,125 6,1459 6,071 5,4849 5,2181 5,1251 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366 3,3828 3,2516 3,134d-distances (Å) 2.8172 2.7589 2.6597 2.6336 2.5956, and Form II olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d-distances (Å) 10.26889 8.577 7,4721 7,125 6,1459 6,071 5,4849 5,2181 5,1251 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366 3, 3828 3,2516 3,134

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 3,0848 3,0638 3,0111 2,8739 2,8102 2,7217 2,6432 2,6007.d-distances (Å) 3.0848 3.0638 3.0111 2.8739 2.8102 2.7217 2.6432 2.6007.

7. Form V olanzapinpolymorf ifølge krav 1, 2 eller 3 fremstillet ved følgende fremgangsmåde: opløsning af Form I eller Form II olanzapin i ca. 50% vandig eddikesyre, og præcipitering af i det væsentlige ren Form V olanzapin under anvendelse af 25% vandig ammoniak, hvor Form I olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 9,9463 8,5579 8,2445 6,8862 6,3787 6,2439 5,5895 5,3055 4,9815 4,8333 4,7255 4,6286 4,533 4,4624The Form V olanzapine polymorph according to claim 1, 2 or 3 prepared by the following method: dissolving Form I or Form II olanzapine in ca. 50% aqueous acetic acid, and precipitation of substantially pure Form V olanzapine using 25% aqueous ammonia, wherein Form I olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d-distances (Å) 9.9463 8 , 5579 8,2445 6,8862 6,3787 6,2439 5,5895 5,3055 4,9815 4,8333 4,7255 4,6286 4,533 4,4624

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 4,2915 4,2346 4,0855 3,8254 3,7489 3,6983 3,5817 3,5064 3,3392 3,2806 3,2138 3,1118 3,0507 2,948 2,8172 2,7589 2,6597 2,6336 2,5956,- og Form II olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande: d-afstande (Å) 10,2689 8,577 7,4721 7,125 6,1459 6,071 5,4849 5,2181 5,1251d-distances (Å) 4.2915 4.2346 4.0855 3.8254 3.7489 3.6983 3.5817 3.5064 3.3392 3.2806 3.2138 3.1118 3.0507 2.948 2.8172 2 , And Form II olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented by the following interplanar distances: d-distances (Å) 10,2689 8,577 7,4721 7,125 6,1459 6,071 5, 4849 5,2181 5,1251

DK 2003 00221 WDK 2003 00221 W

d-afstande (Å) 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366 3,3828 3,2516 3,134 3,0848 3,0638 3,0111 2,8739 2,8102 2,7217 2,6432 2,6007.d-distances (Å) 4,9874 4,7665 4,7158 4,4787 4,3307 4,2294 4,141 3,9873 3,7206 3,5645 3,5366 3,3828 3,2516 3,134 3,0848 3,0638 3,0111 2.8739 2.8102 2.7217 2.6432 2.6007.

8. Farmaceutisk formulering, der som aktiv ingrediens indeholder mindst en olanzapinpolymorf i forbindelse med en eller flere farmaceutisk acceptable bærere, excipienser eller diluenter derfor, hvor nævnte mindst ene olanzapinpolymorf er udvalgt fra gruppen bestående af Form V olanzapin og salte og blandinger deraf, og hvor Form V olanzapin er en olanzapinpolymorf med et typisk røntgenpulverdiffraktionsmønster repræsenteret ved følgende interplanare afstande:A pharmaceutical formulation containing as active ingredient at least one olanzapine polymorph in association with one or more pharmaceutically acceptable carriers, excipients or diluents thereof, wherein said at least one olanzapine polymorph is selected from the group consisting of Form V olanzapine and salts and mixtures thereof, and wherein Form V olanzapine is an olanzapine polymorph with a typical X-ray powder diffraction pattern represented at the following interplanar distances:

DK 2003 00221 WDK 2003 00221 W

9. Anvendelse af mindst en olanzapinpolymorf til fremstilling af et lægemiddel til behandling af en tilstand udvalgt fra gruppen bestående af en psyko-5 tisk tilstand, mild angst og gastrointestinale tilstande, hvor nævnte mindst ene olanzapinpolymorf er udvalgt fra gruppen bestående af Form V olanzapin og salte og blandinger deraf, og hvor Form V olanzapin er olanzapinpolymorf med et typisk røntgenpulverdif -10 fraktionsmønster repræsenteret ved følgende interpla-nare afstande:Use of at least one olanzapine polymorph for the manufacture of a medicament for the treatment of a condition selected from the group consisting of a psychotic condition, mild anxiety and gastrointestinal conditions wherein said at least one olanzapine polymorph is selected from the group consisting of Form V olanzapine and salts and mixtures thereof, and wherein Form V olanzapine is olanzapine polymorph with a typical X-ray powder diffraction pattern represented at the following interplanar distances:

DK 2003 00221 WDK 2003 00221 W

DK 2003 00221 WDK 2003 00221 W

OLANZAPIN - FORM III (KBr) FT-IR SPEKTRUM 1/cm LlOLANZAPINE - FORM III (KBr) FT-IR SPECTRUM 1 / cm Ll

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OLANZAPIN - FORM IV (KBr) FT-IR SPEKTRUM 1/CmOLANZAPINE - FORM IV (KBr) FT-IR SPECTRUM 1 / Cm

didi

LLLL

DK 2003 00221 WDK 2003 00221 W

OLANZAPIN - FORM V (KBr) FT -IR SPEKTRUM -f/cm O)LlOLANZAPINE - FORM V (KBr) FT -IR SPECTRUM -f / cm O) Ll

DK 2003 00221 WDK 2003 00221 W

DK 2003 00221 WDK 2003 00221 W

Shimadzu XRD-6000 CuKa (1,54060 A) 30 kV, 30mA Spalter: DS 1,00 gr, SS:1,00 gr„ RS: 0,15 mm Theta-2Theta (gr.) 1 Firma: X-RAY DIFFRACTION : _Shimadzu XRD-6000 CuKa (1.54060 A) 30 kV, 30mA Columns: DS 1.00 gr, SS: 1.00 gr „RS: 0.15 mm Theta-2Theta (gr.) 1 Company: X-RAY DIFFRACTION : _

Therta-2Theta (gr.) Kont.Scan. 2,0 gr./min 0,60 sek 0,020 gr. RØNTGENDIFFRAKTIONSMØNSTER - FORM IV o o 'sr CM (SdO) I LQTherta-2Theta (gr.) Cont.Scan. 2.0 gr / min 0.60 sec 0.020 gr X-ray diffraction pattern - FORM IV o o 'sr CM (SdO) I LQ

cbLlcbLl

DK 2003 00221 WDK 2003 00221 W

Shimadzu XRD-6000 CuKa (1,54060 A) 30 kV, 30mA Spalter: DS 1,00 ar. SS:1,00 gr„ RS: 0,15 mm Theta-2Theta (gr.) Firma: X-RAY DIFFRACTIONShimadzu XRD-6000 CuKa (1.54060 A) 30 kV, 30mA Column: DS 1.00 ar. SS: 1.00 gr RS: 0.15 mm Theta-2Theta (gr.) Company: X-RAY DIFFRACTION

Therta-2Theta (gr.) Kont.Scan. 2,0 gr./min 0,60 sek 0,020 gr. RØNTGENDIFFRAKTIONSMØNSTER - FORM V w (SdO) ITherta-2Theta (gr.) Cont.Scan. 2.0 gr / min 0.60 sec 0.020 gr X-ray diffraction pattern - FORM V w (SdO) I

CD ri)LlCD ri) Ll

DK200300221U 1999-12-28 2003-08-25 New polymorphic form of olanzapine designated Form V. DK200300221U3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN977BO1999 IN187439B (en)	2000-03-31	1999-12-28
US09/540,749 US6348458B1 (en)	1999-12-28	2000-03-31	Polymorphic forms of olanzapine
DK200300161U DK200300161U3 (en)	1999-12-28	2003-06-16	New polymorphic form of olanzapine, designated Form III

Publications (2)

Publication Number	Publication Date
DK200300221U1 DK200300221U1 (en)	2003-08-25
DK200300221U3 true DK200300221U3 (en)	2003-12-12

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Application Number	Title	Priority Date	Filing Date
DK200300221U DK200300221U3 (en)	1999-12-28	2003-08-25	New polymorphic form of olanzapine designated Form V.
DK200300222U DK200300222U3 (en)	1999-12-28	2003-08-25	New polymorphic form of olanzapine designated Form IV.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DK200300222U DK200300222U3 (en)	1999-12-28	2003-08-25	New polymorphic form of olanzapine designated Form IV.

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- 2003-08-25 DK DK200300221U patent/DK200300221U3/en active
- 2003-08-25 DK DK200300222U patent/DK200300222U3/en active

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DK200300222U1 (en)	2003-08-25
DK200300222U3 (en)	2003-12-12
DK200300221U1 (en)	2003-08-25

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