SI9300486B - Priprava beta-metilkarbapenemskih intermediatov - Google Patents
Priprava beta-metilkarbapenemskih intermediatov Download PDFInfo
- Publication number
- SI9300486B SI9300486B SI9300486A SI9300486A SI9300486B SI 9300486 B SI9300486 B SI 9300486B SI 9300486 A SI9300486 A SI 9300486A SI 9300486 A SI9300486 A SI 9300486A SI 9300486 B SI9300486 B SI 9300486B
- Authority
- SI
- Slovenia
- Prior art keywords
- formula
- compound
- alkylsilyl
- tri
- alkyl
- Prior art date
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- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title claims 3
- 239000000543 intermediate Substances 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 20
- 238000000034 method Methods 0.000 claims abstract 6
- -1 methylmalonic acid ester Chemical class 0.000 claims abstract 6
- 125000006239 protecting group Chemical group 0.000 claims abstract 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000002585 base Substances 0.000 claims 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 235000010290 biphenyl Nutrition 0.000 claims 5
- 239000004305 biphenyl Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000006267 biphenyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 230000020477 pH reduction Effects 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 2
- 150000008045 alkali metal halides Chemical class 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- KJMCAXYHYPDRAV-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-dioxane-4,6-dione Chemical compound CC1C(=O)OC(C)(C)OC1=O KJMCAXYHYPDRAV-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (7)
- / ZAHTEVKI 1. Postopek nastanka karbapenem posrednika s formulo VI, OR'NuVI kjer Nu predstavlja CH2C02‘Bu, SR2 ali OR2, pri čemer je R2 izbran iz naslednjih skupin: vodik; Cm0 nerazvejan ali razvejan aklil; C3.6 cikloalkil; C2-10 nerazvejan ali razvejan alkenil; C2-10 nerazvejan ali razvejan alkinil; C3.6 cikloalkilC-Mo alkil; Ci-6 alkilC3.6 cilkoalkil; fenil ali naftil; benzil ali fentil; tiofen, imidazolil, tetrazolil in furil; tiofen C1-10 alkil, imidazolil C-mo alkil, tetrazolil Cmo alkil in furil Ci-10 alkil; pri čemer so vse te skupine nesubstituirane ali substituirane na N atomu, ki vsebuje deleže, ali disubstituirane na N atomu, ki vsebuje deleže, in kjer so vse zgornje skupine nesubstituirane ali substiuirane na ogljikovih ali N atomih z: amino, hidroksi, ciano, karboksil, nitro, kloro, bromo, fluoro, Ci-6 alkoksi, merkapto, perhalo Ci_6 alkil, guanidino, amidino, sulfamoil, N-substiuirano sulfamoil, N-substituirano amidino, N-substituirano guanidino skupino, pri čemer so omenjene N-substituirane skupine substiuirane z C1.6 alkil ali aril skupinami, ki imajo 6-10 ogljikovih atomov; O1 ali —S R je (a) vodik, (b) metil ali (c) hidroksi zaščitna skupina P' je dušikova zaščitna skupina, vsebujoč: reakcijo spojine s formulo IVkjer je P' definiran zgoraj, v nereaktivnem topilu ali C-i_6 alkanolu z bazo in nukleofilom , ki po nakisanju povzroči nastanek spojine s formulo Vv 3 kjer sta P' in Nu razložena zgoraj, in nato z reakcijo spojine s formulo V v estru ali blago kisli eterični raztopini da dobimo spojino s formulo VI.
- 2. Postopek po zahtevku 1 dalje vsebuje reakcijo spojine, označene s formulo IIIv aprotičnem topilu s čisto bazo, alkalijskim metalohalidom in tri-organo halo silanom za nastanek spojine s formulo IV
- 3. Postopek nastanka beta-metil karbapenem posrednika s formulo VI:vi kjer je Nu tak kot je označen v zahtevku 1; R je (a) vodik, (b) metil ali (c) hidroksi zaščitno skupino; P' je dušikova zaščitna skupina vsebujoč: (a) reakcijo spojine označene s formulo I, ORv kateri je j R1 je: (a) -0-C(0)-R", kjer R" je Ci^ alkil, alil ali substituiran fenil, pri katerem je substituent vodik, C1-3 alkil, halo, nitro, ciano ali C 1.3 alkiloksi, (b) -S(0)n-R2, kjer je n 1 ali 2 in R2 je fenil, bifenil, naftil, v danem primeru substituiran s halidom ali C1.4 alkilom in (c) halo, v nereaktivnem topilu z 2,2,5-trimetil-1,3-dioksan-4,6-dionom in bazo za nastanek spojine s formulo lil; r(b) reakcijo spojine označene s formulo III v aprotičnem topilu s čisto bazo, alkalijskim metalohalidom in tri-organo halosilanom za nastanek spojine s formulo IViv (c) reakcijo spojine, označene formulo IV v nereaktivnem topilu ali C1.6 alkanolu z bazo in nukleofilom, ki ju označimo s formulo NuX, za nastanek po nakisanju spojine s formulo Vv kjer je Nu tak kot je definiran v zahtevku 1 in je X izstopajoča skupina. ί
- 4. Postopek nastanka karbapenem posrednika s formulo V:V kjer je Nu tak kot je definiran v zahtevku 1, Rje (a) vodik, (b) metil ali (c) tri-organosilil izbran iz tri-Ci_4 alkilsilila, fenila di C1-4 alkilsilila in difenil mono C14 alkilsilila, P' predstavlja tri-organo silil, izbran iz tri-Ci_4 alkilsilila, fenil di C1.4 alkilsilila in difenil mono C1-4 alkilsilila; vsebujoč: (c) reakcijo spojine, označene s formulo IV:IV v nereaktivnim topilu ali Ci_6 alkanolu z bazo in spojino s formulo NuX , ki po nakisanju povzroči nastanek spojine s formulo Vv kjer je Nu tak kot je definiran v zahtevku 1 in je X izstopajoča skupina.
- 5. Spojina, označena s formulo III, IV, ali Vv kjer je Nu tak kot je definiran v zahtevku 1, R je (a) vodik, (b) metil ali (c) hidroksi zaščitna skupina; in P' je dušikova zaščitna skupina; s pridržkom, da ko je spojina formule V, Nu je vodik in P' je benzil takrat R ni TBDMS.
- 6. Spojina po zahtevku 5 kjer Rje (a) vodik, (b) metil ali (c) tri-organosilil izbran iz tri-Ci_4 alkilsilila, fenila di C-m alkilsilila in difenil mono C-u alkilsilila, in P' je tri-organo silil, Tri-C^ alkilsilil, fenil di Ci^ alkilsilil in difenil mono C1-4 alkilsilil;
- 7. Spojina označena s formulo V OR•NuO kjer je Nu tak kot je definiran v zahtevku 1, (d) vodik, (e) metil ali (f) hidroksi zaščitna skupina; in P' je dušikova zaščitna skupina s pridržkom da, ko je Nu vodik in P' je benzil takrat R ni TBDMS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94718692A | 1992-09-18 | 1992-09-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9300486A SI9300486A (en) | 1994-03-31 |
| SI9300486B true SI9300486B (sl) | 2003-02-28 |
Family
ID=25485687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300486A SI9300486B (sl) | 1992-09-18 | 1993-09-17 | Priprava beta-metilkarbapenemskih intermediatov |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6242596B1 (sl) |
| EP (1) | EP0589626B1 (sl) |
| JP (1) | JP3252032B2 (sl) |
| CN (2) | CN1066438C (sl) |
| AR (1) | AR000394A2 (sl) |
| AT (1) | ATE214048T1 (sl) |
| AU (1) | AU667571B2 (sl) |
| CA (1) | CA2106248A1 (sl) |
| CZ (1) | CZ286267B6 (sl) |
| DE (1) | DE69331650T2 (sl) |
| DK (1) | DK0589626T3 (sl) |
| ES (1) | ES2173884T3 (sl) |
| FI (1) | FI951212L (sl) |
| HK (1) | HK1008336A1 (sl) |
| HR (1) | HRP931199B1 (sl) |
| MX (1) | MX9305715A (sl) |
| PT (1) | PT589626E (sl) |
| RO (1) | RO116087B1 (sl) |
| RU (1) | RU2130927C1 (sl) |
| SI (1) | SI9300486B (sl) |
| SK (1) | SK282164B6 (sl) |
| TW (1) | TW406073B (sl) |
| UA (1) | UA50705C2 (sl) |
| WO (1) | WO1994006764A1 (sl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1061233C (zh) * | 1996-12-13 | 2001-01-31 | 高琳 | 一种保健口服液及其生产工艺 |
| KR100335848B1 (ko) * | 2000-03-31 | 2002-05-08 | 윤재승 | 아제티디논 유도체, 그 제조방법 및 이를 이용한1-β-알킬아제티디논의 제조방법 |
| US6625203B2 (en) * | 2001-04-30 | 2003-09-23 | Interdigital Technology Corporation | Fast joint detection |
| EP1878829A1 (de) | 2006-07-12 | 2008-01-16 | Papierfabriken Cham-Tenero AG | Beschichtetes Trägerpapier |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982001705A1 (en) * | 1980-11-13 | 1982-05-27 | Takeda Chemical Industries Ltd | 4-substituted-2-oxoazetidine derivatives and process for their preparation |
| AU548727B2 (en) * | 1981-03-12 | 1986-01-02 | Gruppo Lepetit S.P.A. | Beta-lactam acetic acid derivatives |
| US4576747A (en) * | 1984-05-07 | 1986-03-18 | The Upjohn Company | Isocyanato-azetidinediones |
| EP0177454B1 (de) * | 1984-10-04 | 1988-12-21 | Ciba-Geigy Ag | Silane, Verfahren zu deren Herstellung und deren Verwendung |
| DE3879791T2 (de) | 1987-07-17 | 1993-10-14 | Merck & Co Inc | 4-Substituierte 3-Oxobutanoat-Esterderivate. |
| ES2054604T3 (es) * | 1987-09-22 | 1995-12-01 | Shionogi & Co | Intermedios alquenilsililazetidinona para carbapenemes. |
| US4992545A (en) * | 1989-09-20 | 1991-02-12 | Eli Lilly And Company | Process for preparing 4-substituted azetidinones |
| EP0546742B1 (en) * | 1991-12-09 | 2001-06-20 | Takasago International Corporation | 4-(1,1-Dialkoxycarbonyl-alkyl)azetidin-2-one derivatives and synthesis of 4-(1-carboxy-alkyl)azetidin-2-one derivatives therefrom |
-
1993
- 1993-09-09 UA UA95038225A patent/UA50705C2/uk unknown
- 1993-09-09 RO RO95-00535A patent/RO116087B1/ro unknown
- 1993-09-09 WO PCT/US1993/008474 patent/WO1994006764A1/en active IP Right Grant
- 1993-09-09 SK SK349-95A patent/SK282164B6/sk unknown
- 1993-09-09 RU RU95108544/04A patent/RU2130927C1/ru not_active IP Right Cessation
- 1993-09-09 CZ CZ1995346A patent/CZ286267B6/cs not_active IP Right Cessation
- 1993-09-15 CA CA002106248A patent/CA2106248A1/en not_active Abandoned
- 1993-09-16 EP EP93307322A patent/EP0589626B1/en not_active Expired - Lifetime
- 1993-09-16 HR HR931199A patent/HRP931199B1/xx not_active IP Right Cessation
- 1993-09-16 DK DK93307322T patent/DK0589626T3/da active
- 1993-09-16 AT AT93307322T patent/ATE214048T1/de not_active IP Right Cessation
- 1993-09-16 ES ES93307322T patent/ES2173884T3/es not_active Expired - Lifetime
- 1993-09-16 DE DE69331650T patent/DE69331650T2/de not_active Expired - Fee Related
- 1993-09-16 PT PT93307322T patent/PT589626E/pt unknown
- 1993-09-17 TW TW082107633A patent/TW406073B/zh not_active IP Right Cessation
- 1993-09-17 JP JP23154793A patent/JP3252032B2/ja not_active Expired - Fee Related
- 1993-09-17 AU AU47433/93A patent/AU667571B2/en not_active Ceased
- 1993-09-17 MX MX9305715A patent/MX9305715A/es not_active IP Right Cessation
- 1993-09-17 SI SI9300486A patent/SI9300486B/sl not_active IP Right Cessation
- 1993-09-17 CN CN93119208A patent/CN1066438C/zh not_active Expired - Fee Related
-
1994
- 1994-05-12 US US08/241,958 patent/US6242596B1/en not_active Expired - Fee Related
-
1995
- 1995-03-15 FI FI951212A patent/FI951212L/fi not_active IP Right Cessation
- 1995-05-04 US US08/435,013 patent/US5654424A/en not_active Expired - Fee Related
- 1995-12-19 AR AR33470595A patent/AR000394A2/es unknown
-
1998
- 1998-07-20 HK HK98109271A patent/HK1008336A1/xx not_active IP Right Cessation
- 1998-12-17 CN CN98125797A patent/CN1101397C/zh not_active Expired - Fee Related
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| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20050608 |