ES2207979T3 - Proceso para la sintesis de acido 1-(amino-metil)-ciclohexil-acetico. - Google Patents
Proceso para la sintesis de acido 1-(amino-metil)-ciclohexil-acetico.Info
- Publication number
- ES2207979T3 ES2207979T3 ES99963652T ES99963652T ES2207979T3 ES 2207979 T3 ES2207979 T3 ES 2207979T3 ES 99963652 T ES99963652 T ES 99963652T ES 99963652 T ES99963652 T ES 99963652T ES 2207979 T3 ES2207979 T3 ES 2207979T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- methyl
- acid
- nitro
- cyclohexyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 20
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 16
- 239000002253 acid Substances 0.000 title claims description 26
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 5
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 230000009466 transformation Effects 0.000 claims abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- -1 nitro-methyl Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- UKYISVNNIPKTNG-UHFFFAOYSA-N 2-cyclohexylideneacetic acid Chemical compound OC(=O)C=C1CCCCC1 UKYISVNNIPKTNG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- ZPHMHWZOMBHXDM-UHFFFAOYSA-N [1-(nitromethyl)cyclohexyl] acetate Chemical compound CC(=O)OC1(C[N+]([O-])=O)CCCCC1 ZPHMHWZOMBHXDM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010931 ester hydrolysis Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- KTVHUWOVEOQHPU-UHFFFAOYSA-N 2-[1-(nitromethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(C[N+]([O-])=O)CCCCC1 KTVHUWOVEOQHPU-UHFFFAOYSA-N 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229960002870 gabapentin Drugs 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- XBUDZAQEMFGLEU-UHFFFAOYSA-N 2-[1-(aminomethyl)cyclohexyl]acetic acid;hydron;chloride Chemical class Cl.OC(=O)CC1(CN)CCCCC1 XBUDZAQEMFGLEU-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JAWPQJDOQPSNIQ-UHFFFAOYSA-N 2-Azaspiro[4.5]decan-3-one Chemical class C1NC(=O)CC21CCCCC2 JAWPQJDOQPSNIQ-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 description 1
- QDSFNOHWQKVVEB-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)morpholine Chemical compound CCOP(=O)(OCC)CN1CCOCC1 QDSFNOHWQKVVEB-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/51—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9803034 | 1998-12-29 | ||
| HU9803034A HU225502B1 (en) | 1998-12-29 | 1998-12-29 | Process for producing 1-(amino-metyl)-cyclohexene-acetic-acid and intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2207979T3 true ES2207979T3 (es) | 2004-06-01 |
Family
ID=89997614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99963652T Expired - Lifetime ES2207979T3 (es) | 1998-12-29 | 1999-12-23 | Proceso para la sintesis de acido 1-(amino-metil)-ciclohexil-acetico. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6765114B1 (enExample) |
| JP (1) | JP2002533431A (enExample) |
| CN (1) | CN1221525C (enExample) |
| AT (1) | ATE250569T1 (enExample) |
| AU (1) | AU1996300A (enExample) |
| BG (1) | BG65056B1 (enExample) |
| CA (1) | CA2349826C (enExample) |
| CZ (1) | CZ301922B6 (enExample) |
| DE (1) | DE69911646T2 (enExample) |
| DK (1) | DK1140793T3 (enExample) |
| EA (1) | EA003555B1 (enExample) |
| EE (1) | EE04587B1 (enExample) |
| ES (1) | ES2207979T3 (enExample) |
| HU (1) | HU225502B1 (enExample) |
| PL (1) | PL196854B1 (enExample) |
| SK (1) | SK287019B6 (enExample) |
| UA (1) | UA73108C2 (enExample) |
| WO (1) | WO2000039074A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL363155A1 (en) * | 2000-06-16 | 2004-11-15 | Teva Pharmaceutical Industries, Ltd. | Stable gabapentin having ph within a controlled range |
| CA2660769C (en) * | 2006-06-30 | 2013-12-03 | Zach System S.P.A. | Process for preparing gabapentin |
| WO2009147434A1 (en) * | 2008-06-03 | 2009-12-10 | Generics [Uk] Limited | A novel and efficient method for the synthesis of an amino acid |
| CN104974037B (zh) * | 2014-04-13 | 2019-04-30 | 江苏康缘药业股份有限公司 | 一种含羧基多羰基姜黄素衍生物及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3253039A (en) * | 1962-02-05 | 1966-05-24 | Engelhard Ind Inc | Catalytic hydrogenation of organic nitrocompounds |
| US3594419A (en) * | 1968-04-15 | 1971-07-20 | Gulf Research Development Co | Process for converting nitroparaffins to amines |
| US3766271A (en) * | 1971-03-04 | 1973-10-16 | Texaco Inc | Homogeneous catalysts useful in the reduction of nitroparaffins to amines |
| DE2460891C2 (de) * | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4894476A (en) * | 1988-05-02 | 1990-01-16 | Warner-Lambert Company | Gabapentin monohydrate and a process for producing the same |
| DE3928182A1 (de) | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von gabapentin |
| DE3928183A1 (de) | 1989-08-25 | 1991-02-28 | Goedecke Ag | Lactamfreie cyclische aminosaeuren |
| FI905584A7 (fi) * | 1989-11-16 | 1991-05-17 | Lonza Ag | Menetelmä 1-(aminometyyli)sykloheksaanietikkahapon valmistamiseksi |
| CN1303059C (zh) | 1997-10-27 | 2007-03-07 | 沃尼尔·朗伯公司 | 作为药物的环状氨基酸及其衍生物 |
-
1998
- 1998-12-29 HU HU9803034A patent/HU225502B1/hu not_active IP Right Cessation
-
1999
- 1999-12-23 CZ CZ20012070A patent/CZ301922B6/cs not_active IP Right Cessation
- 1999-12-23 EE EEP200100295A patent/EE04587B1/xx not_active IP Right Cessation
- 1999-12-23 US US09/856,517 patent/US6765114B1/en not_active Expired - Fee Related
- 1999-12-23 ES ES99963652T patent/ES2207979T3/es not_active Expired - Lifetime
- 1999-12-23 EA EA200100723A patent/EA003555B1/ru not_active IP Right Cessation
- 1999-12-23 JP JP2000590987A patent/JP2002533431A/ja active Pending
- 1999-12-23 AU AU19963/00A patent/AU1996300A/en not_active Abandoned
- 1999-12-23 DK DK99963652T patent/DK1140793T3/da active
- 1999-12-23 UA UA2001075268A patent/UA73108C2/uk unknown
- 1999-12-23 PL PL348461A patent/PL196854B1/pl not_active IP Right Cessation
- 1999-12-23 CN CNB998129593A patent/CN1221525C/zh not_active Expired - Fee Related
- 1999-12-23 DE DE69911646T patent/DE69911646T2/de not_active Expired - Lifetime
- 1999-12-23 SK SK937-2001A patent/SK287019B6/sk not_active IP Right Cessation
- 1999-12-23 WO PCT/HU1999/000102 patent/WO2000039074A1/en not_active Ceased
- 1999-12-23 CA CA002349826A patent/CA2349826C/en not_active Expired - Fee Related
- 1999-12-23 AT AT99963652T patent/ATE250569T1/de not_active IP Right Cessation
-
2001
- 2001-05-07 BG BG105491A patent/BG65056B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000039074A1 (en) | 2000-07-06 |
| PL348461A1 (en) | 2002-05-20 |
| JP2002533431A (ja) | 2002-10-08 |
| DK1140793T3 (da) | 2004-02-02 |
| CA2349826A1 (en) | 2000-07-06 |
| SK9372001A3 (en) | 2002-01-07 |
| BG65056B1 (bg) | 2007-01-31 |
| HU225502B1 (en) | 2007-01-29 |
| CN1325378A (zh) | 2001-12-05 |
| PL196854B1 (pl) | 2008-02-29 |
| EA200100723A1 (ru) | 2001-12-24 |
| US6765114B1 (en) | 2004-07-20 |
| BG105491A (en) | 2001-12-29 |
| SK287019B6 (sk) | 2009-09-07 |
| EE04587B1 (et) | 2006-02-15 |
| AU1996300A (en) | 2000-07-31 |
| DE69911646T2 (de) | 2004-07-08 |
| CA2349826C (en) | 2009-05-12 |
| EE200100295A (et) | 2002-12-16 |
| CN1221525C (zh) | 2005-10-05 |
| HUP9803034A2 (hu) | 2001-02-28 |
| DE69911646D1 (de) | 2003-10-30 |
| HU9803034D0 (en) | 1999-02-01 |
| UA73108C2 (en) | 2005-06-15 |
| ATE250569T1 (de) | 2003-10-15 |
| EA003555B1 (ru) | 2003-06-26 |
| CZ301922B6 (cs) | 2010-07-28 |
| CZ20012070A3 (cs) | 2001-09-12 |
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