HRP20100054T1 - Dobivanje pregabalina i njemu sličnih spojeva - Google Patents
Dobivanje pregabalina i njemu sličnih spojeva Download PDFInfo
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- HRP20100054T1 HRP20100054T1 HR20100054T HRP20100054T HRP20100054T1 HR P20100054 T1 HRP20100054 T1 HR P20100054T1 HR 20100054 T HR20100054 T HR 20100054T HR P20100054 T HRP20100054 T HR P20100054T HR P20100054 T1 HRP20100054 T1 HR P20100054T1
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- 150000001875 compounds Chemical class 0.000 title claims abstract 48
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title 1
- 229960001233 pregabalin Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 39
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 17
- 238000000034 method Methods 0.000 claims abstract 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 10
- 239000012453 solvate Substances 0.000 claims abstract 9
- 239000002253 acid Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 10
- 102000004190 Enzymes Human genes 0.000 claims 4
- 108090000790 Enzymes Proteins 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000000911 decarboxylating effect Effects 0.000 claims 2
- JHRWFZAGFWIERB-RKDXNWHRSA-N (2r,3s)-3-cyano-2-ethoxycarbonyl-5-methylhexanoic acid Chemical compound CCOC(=O)[C@@H](C(O)=O)[C@@H](C#N)CC(C)C JHRWFZAGFWIERB-RKDXNWHRSA-N 0.000 claims 1
- JHRWFZAGFWIERB-BDAKNGLRSA-N (2s,3s)-3-cyano-2-ethoxycarbonyl-5-methylhexanoic acid Chemical compound CCOC(=O)[C@H](C(O)=O)[C@@H](C#N)CC(C)C JHRWFZAGFWIERB-BDAKNGLRSA-N 0.000 claims 1
- JHRWFZAGFWIERB-VEDVMXKPSA-N (3s)-3-cyano-2-ethoxycarbonyl-5-methylhexanoic acid Chemical compound CCOC(=O)C(C(O)=O)[C@@H](C#N)CC(C)C JHRWFZAGFWIERB-VEDVMXKPSA-N 0.000 claims 1
- VOPQXWXHHIIKRZ-MLWJPKLSSA-N (3s)-4-(2-methylpropyl)-2-oxopyrrolidine-3-carboxylic acid Chemical class CC(C)CC1CNC(=O)[C@H]1C(O)=O VOPQXWXHHIIKRZ-MLWJPKLSSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- CMROGFZABRZODL-ZCFIWIBFSA-N 2-[(1s)-1-cyano-3-methylbutyl]propanedioic acid Chemical compound CC(C)C[C@H](C#N)C(C(O)=O)C(O)=O CMROGFZABRZODL-ZCFIWIBFSA-N 0.000 claims 1
- VPHWGVGMWFDYEM-ZCFIWIBFSA-N 2-[(2s)-1-amino-4-methylpentan-2-yl]propanedioic acid Chemical compound CC(C)C[C@H](CN)C(C(O)=O)C(O)=O VPHWGVGMWFDYEM-ZCFIWIBFSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- PZGIWBPMOSUKEV-JTQLQIEISA-N diethyl 2-[(1r)-1-cyano-3-methylbutyl]propanedioate Chemical compound CCOC(=O)C([C@@H](CC(C)C)C#N)C(=O)OCC PZGIWBPMOSUKEV-JTQLQIEISA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C227/20—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/002—Nitriles (-CN)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
Abstract
Postupak dobivanja spoja Formule 1ili njegovog farmaceutski prihvatljivog kompleksa, soli, solvata ili hidrata, u kojojR1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, naznačen time što navedeni postupak se sastoji u: (a) reakciji spoja Formule 2ili njegove soli, s kiselinom i vodom, kako bi se dobilo spoj Formule 1, ili njegovu sol; ili (b) izbornom prevođenju spoja Formule 1, ili njegove soli, u njegov farmaceutski prihvatljiv kompleks, sol, solvat ili hidrat, gdje R1 i R2 u Formuli 2 su definirani kao za Formulu 1. Patent sadrži još 12 patentnih zahtjeva.
Claims (13)
1. Postupak dobivanja spoja Formule 1
[image]
ili njegovog farmaceutski prihvatljivog kompleksa, soli, solvata ili hidrata, u kojoj
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila,
naznačen time što navedeni postupak se sastoji u:
(a) reakciji spoja Formule 2
[image]
ili njegove soli, s kiselinom i vodom, kako bi se dobilo spoj Formule 1, ili njegovu sol; ili
(b) izbornom prevođenju spoja Formule 1, ili njegove soli, u njegov farmaceutski prihvatljiv kompleks, sol, solvat ili hidrat, gdje R1 i R2 u Formuli 2 su definirani kao za Formulu 1.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se dodatno sastoji u redukciji cijano ostatka u spoju Formule 3
[image]
ili njegovoj soli, kako bi se dobilo spoj Formule 2, ili njegovu sol, gdje
R1 i R2 u Formuli 3 su definirani kao za Formulu 1; i
R3 u Formuli 3 je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
3. Postupak u skladu s patentnim zahtjevom 2, naznačen time što se dodatno sastoji u:
(a) miješanju spoja Formule 4
[image]
s enzimom, kako bi se dobilo spoj Formule 3, ili njegovu sol, i spoj Formule 5
[image]
gdje enzim je prilagođen tako da enantioselektivno hidrolizira spoj Formule 4 u spoj Formule 3, ili njegovu sol;
(b) izdvajanju spoja Formule 3, ili njegove soli; i
(c) izbornom racemiziranju spoja Formule 5, kako bi se dobilo spoj Formule 4, gdje
R1, R2 i R3 u Formuli 4 i Formuli 5 su definirani kao za Formulu 3; i
R4 u Formuli 4 i Formuli 5 je isti kao ili je različit od R3, te je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
4. Postupak dobivanja spoja Formule 1
[image]
ili njegovog farmaceutski prihvatljivog kompleksa, soli, solvata ili hidrata, u kojoj
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila,
naznačen time što navedeni postupak se sastoji u:
(a) redukciji cijano ostatka u spoju Formule 6
[image]
ili njegovoj soli, kako bi se dobilo spoj Formule 7
[image]
ili njegovu sol;
(b) dekarboksiliranju spoja Formule 7, ili njegove soli, kako bi se dobilo spoj Formule 1, ili njegovu sol; i
(c) izbornom prevođenju spoja Formule 1, ili njegove soli, u njegov farmaceutski prihvatljiv kompleks, sol, solvat ili hidrat, gdje R1 i R2 u Formuli 6 i Formuli 7 su definirani kao za Formulu 1.
5. Postupak dobivanja spoja Formule 1
[image]
ili njegovog farmaceutski prihvatljivog kompleksa, soli, solvata ili hidrata, u kojoj
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila,
naznačen time što navedeni postupak se sastoji u:
(a) dekarboksiliranju spoja Formule 3
[image]
ili njegove soli, ili hidrolizi i dekarboksiliranju spoja Formule 3, ili njegove soli, kako bi se dobilo spoj Formule 8
[image]
ili njegovu sol;
(b) redukciji cijano ostatka u spoju Formule 8, ili njegovoj soli, kako bi se dobilo spoj Formule 1, ili njegovu sol; i
(c) izbornom prevođenju spoja Formule 1, ili njegove soli, u njegov farmaceutski prihvatljiv kompleks, sol, solvat ili hidrat, gdje
svaki od R1 i R2 u Formuli 3 i Formuli 8 je definiran kao za Formulu 1;
R3 u Formuli 3 je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil; i
R5 u Formuli 8 je atom vodika, C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
6. Postupak dobivanja spoja Formule 3
[image]
ili njegovog farmaceutski prihvatljivog kompleksa, soli, solvata ili hidrata, u kojoj
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, i
R3 je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil,
naznačen time što navedeni postupak se sastoji u:
(a) miješanju spoja Formule 4
[image]
s enzimom, kako bi se dobilo spoj Formule 3, ili njegovu sol, i spoj Formule 5
[image]
gdje enzim je prilagođen tako da enantioselektivno hidrolizira spoj Formule 4 u spoj Formule 3, ili njegovu sol;
(b) izdvajanju spoja Formule 3, ili njegove soli; i
(c) izbornom racemiziranju spoja Formule 5, kako bi se dobilo spoj Formule 4, gdje
R1, R2 i R3 u Formuli 4 i Formuli 5 su definirani kao za Formulu 3; i
R4 u Formuli 4 i Formuli 5 je isti kao ili je različit od R3, te je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što R1 je atom vodika, a R2 je izobutil u spojevima Formule 1 do Formule 8.
8. Spoj Formule 2
[image]
uključujući njegove soli, naznačen time što
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, uz uvjet da kada jedan od supstituenata kojeg predstavlja R1 ili R2 je vodik, drugi supstituent nije C1-3 alkil ili C5 alkil.
9. Spoj Formule 3
[image]
uključujući njegove soli, naznačen time što
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, uz uvjet da kada jedan od supstituenata kojeg predstavlja R1 ili R2 je vodik, drugi supstituent nije metil; i
R3 je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
10. Spoj Formule 5
[image]
uključujući njegove soli, naznačen time što
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, uz uvjet da kada jedan od supstituenata kojeg predstavlja R1 ili R2 je vodik, drugi supstituent nije metil; i
svaki od R3 i R4 je C1-12 alkil, C3-12 cikloalkil ili aril-C1-6 alkil.
11. Spoj Formule 6
[image]
uključujući njegove soli, naznačen time što
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, uz uvjet da kada jedan od supstituenata kojeg predstavlja R1 ili R2 je vodik, drugi supstituent nije metil.
12. Spoj Formule 7
[image]
uključujući njegove soli, naznačen time što
R1 i R2 su različiti i svakog od njih se neovisno bira između atoma vodika, C1-12 alkila, C3-12 cikloalkila i supstituiranog C3-12 cikloalkila, uz uvjet da kada jedan od supstituenata kojeg predstavlja R1 ili R2 je vodik, drugi supstituent nije metil.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 8 do 12, naznačen time što ga se bira između:
(S)-4-izobutil-2-oksopirolidin-3-karboksilne kiseline;
(3S)-3-cijano-2-etoksikarbonil-5-metilheksanske kiseline,
(2S,3S)-3-cijano-2-etoksikarbonil-5-metilheksanske kiseline,
(2R,3S)-3-cijano-2-etoksikarbonil-5-metilheksanske kiseline;
etilnog estera (R)-3-cijano-2-etoksikarbonil-5-metilheksanske kiseline;
(S)-3-cijano-2-karboksi-5-metilheksanske kiseline; odnosno
(S)-3-aminometil-2-karboksi-5-metilheksanske kiseline;
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58167104P | 2004-06-21 | 2004-06-21 | |
| US62903404P | 2004-11-18 | 2004-11-18 | |
| PCT/IB2005/001924 WO2006000904A2 (en) | 2004-06-21 | 2005-06-09 | Preparation of pregabalin and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100054T1 true HRP20100054T1 (hr) | 2010-05-31 |
Family
ID=35295367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100054T HRP20100054T1 (hr) | 2004-06-21 | 2010-01-29 | Dobivanje pregabalina i njemu sličnih spojeva |
Country Status (33)
| Country | Link |
|---|---|
| US (4) | US20050283023A1 (hr) |
| EP (1) | EP1831154B1 (hr) |
| JP (5) | JP4174551B2 (hr) |
| KR (3) | KR100847928B1 (hr) |
| CN (2) | CN1972904B (hr) |
| AP (1) | AP2466A (hr) |
| AR (1) | AR049446A1 (hr) |
| AT (1) | ATE455093T1 (hr) |
| AU (1) | AU2005256945B2 (hr) |
| BR (1) | BRPI0512347B8 (hr) |
| CA (1) | CA2571040C (hr) |
| CR (2) | CR8765A (hr) |
| CY (1) | CY1110337T1 (hr) |
| DE (1) | DE602005018965D1 (hr) |
| DK (1) | DK1831154T3 (hr) |
| EA (3) | EA015418B1 (hr) |
| ES (1) | ES2336014T3 (hr) |
| GE (1) | GEP20104895B (hr) |
| HK (2) | HK1104024A1 (hr) |
| HR (1) | HRP20100054T1 (hr) |
| IL (1) | IL179614A0 (hr) |
| MA (1) | MA28674B1 (hr) |
| ME (1) | ME01067B (hr) |
| MX (1) | MXPA06014228A (hr) |
| NO (1) | NO338097B1 (hr) |
| NZ (1) | NZ552220A (hr) |
| PL (1) | PL1831154T3 (hr) |
| PT (1) | PT1831154E (hr) |
| RS (1) | RS51210B (hr) |
| SI (1) | SI1831154T1 (hr) |
| TW (6) | TWI377191B (hr) |
| UA (1) | UA83575C2 (hr) |
| WO (1) | WO2006000904A2 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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