NO313939B1 - Heterosykliske tioestere og -ketoner, farmasöytiske preparater omfattende slike, fremgangsmåte for fremstilling og anvendelse av slikeforbindelser - Google Patents
Heterosykliske tioestere og -ketoner, farmasöytiske preparater omfattende slike, fremgangsmåte for fremstilling og anvendelse av slikeforbindelser Download PDFInfo
- Publication number
- NO313939B1 NO313939B1 NO19991432A NO991432A NO313939B1 NO 313939 B1 NO313939 B1 NO 313939B1 NO 19991432 A NO19991432 A NO 19991432A NO 991432 A NO991432 A NO 991432A NO 313939 B1 NO313939 B1 NO 313939B1
- Authority
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- Norway
- Prior art keywords
- dimethyl
- phenyl
- propyl
- alkyl
- branched
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 129
- -1 Heterocyclic thioesters Chemical class 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 15
- 150000002576 ketones Chemical class 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
- 125000001624 naphthyl group Chemical group 0.000 claims description 41
- 125000004076 pyridyl group Chemical group 0.000 claims description 41
- 239000004305 biphenyl Substances 0.000 claims description 40
- 235000010290 biphenyl Nutrition 0.000 claims description 40
- 125000006267 biphenyl group Chemical group 0.000 claims description 40
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 21
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- 125000001424 substituent group Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
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- 230000001537 neural effect Effects 0.000 claims description 12
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- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 9
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- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- GBHSQMPDHDCQCE-UHFFFAOYSA-N o-(3-phenylpropyl) 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carbothioate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCCC1C(=S)OCCCC1=CC=CC=C1 GBHSQMPDHDCQCE-UHFFFAOYSA-N 0.000 claims description 5
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- WRVUVUSXKPMOPJ-UHFFFAOYSA-N 3,3-dimethyl-1-[2-(5-phenylpentanoyl)piperidin-1-yl]pentane-1,2-dione Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCCC1C(=O)CCCCC1=CC=CC=C1 WRVUVUSXKPMOPJ-UHFFFAOYSA-N 0.000 claims description 4
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- ZTYYAAUDVNUOHF-NRFANRHFSA-N o-(3-naphthalen-2-ylpropyl) (2s)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carbothioate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=S)OCCCC1=CC=C(C=CC=C2)C2=C1 ZTYYAAUDVNUOHF-NRFANRHFSA-N 0.000 claims description 3
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- LOKGYULZNQLSGJ-UHFFFAOYSA-N s-(1-benzothiophen-3-ylmethyl) 1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carbothioate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)SCC1=CSC2=CC=CC=C12 LOKGYULZNQLSGJ-UHFFFAOYSA-N 0.000 claims description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
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Classifications
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- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A—HUMAN NECESSITIES
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no double bonds between ring members or between ring members and non-ring members 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
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
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- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
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- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
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- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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PCT/US1997/015832 WO1998013343A1 (en) | 1996-09-25 | 1997-09-09 | Heterocyclic thioesters and ketones |
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NO991432D0 NO991432D0 (no) | 1999-03-24 |
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NO19991432A NO313939B1 (no) | 1996-09-25 | 1999-03-24 | Heterosykliske tioestere og -ketoner, farmasöytiske preparater omfattende slike, fremgangsmåte for fremstilling og anvendelse av slikeforbindelser |
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EP (3) | EP1900726A1 (cs) |
JP (1) | JP2001506231A (cs) |
KR (1) | KR100574109B1 (cs) |
CN (1) | CN1285575C (cs) |
AR (1) | AR009783A1 (cs) |
AT (2) | ATE380791T1 (cs) |
AU (1) | AU739361B2 (cs) |
BG (1) | BG103233A (cs) |
BR (1) | BR9713202A (cs) |
CA (1) | CA2263927C (cs) |
CZ (1) | CZ298120B6 (cs) |
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EA (2) | EA200100948A1 (cs) |
ES (1) | ES2298912T3 (cs) |
ID (1) | ID19615A (cs) |
IL (2) | IL128792A (cs) |
NO (1) | NO313939B1 (cs) |
NZ (3) | NZ334315A (cs) |
PA (1) | PA8438401A1 (cs) |
PE (1) | PE110498A1 (cs) |
PL (1) | PL194249B1 (cs) |
SG (1) | SG109418A1 (cs) |
SK (1) | SK26599A3 (cs) |
WO (1) | WO1998013343A1 (cs) |
ZA (1) | ZA977900B (cs) |
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-
1996
- 1996-09-25 US US08/721,765 patent/US5786378A/en not_active Expired - Fee Related
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1997
- 1997-08-01 US US08/904,461 patent/US5990131A/en not_active Expired - Fee Related
- 1997-09-03 ZA ZA977900A patent/ZA977900B/xx unknown
- 1997-09-09 CZ CZ0055699A patent/CZ298120B6/cs not_active IP Right Cessation
- 1997-09-09 BR BR9713202-0A patent/BR9713202A/pt not_active Application Discontinuation
- 1997-09-09 AU AU42590/97A patent/AU739361B2/en not_active Ceased
- 1997-09-09 EA EA200100948A patent/EA200100948A1/ru unknown
- 1997-09-09 EA EA199900182A patent/EA002982B1/ru not_active IP Right Cessation
- 1997-09-09 WO PCT/US1997/015832 patent/WO1998013343A1/en active IP Right Grant
- 1997-09-09 NZ NZ334315A patent/NZ334315A/xx unknown
- 1997-09-09 EP EP07023749A patent/EP1900726A1/en not_active Withdrawn
- 1997-09-09 AT AT05025042T patent/ATE380791T1/de not_active IP Right Cessation
- 1997-09-09 CN CNB97198199XA patent/CN1285575C/zh not_active Expired - Fee Related
- 1997-09-09 DE DE69738382T patent/DE69738382T2/de not_active Expired - Lifetime
- 1997-09-09 EP EP97940917A patent/EP0934263B8/en not_active Expired - Lifetime
- 1997-09-09 ES ES05025042T patent/ES2298912T3/es not_active Expired - Lifetime
- 1997-09-09 EP EP05025042A patent/EP1626043B1/en not_active Expired - Lifetime
- 1997-09-09 SK SK265-99A patent/SK26599A3/sk unknown
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- 1997-09-09 PL PL97332205A patent/PL194249B1/pl not_active IP Right Cessation
- 1997-09-09 AT AT97940917T patent/ATE310722T1/de not_active IP Right Cessation
- 1997-09-09 NZ NZ507720A patent/NZ507720A/xx unknown
- 1997-09-09 KR KR1019997002525A patent/KR100574109B1/ko not_active IP Right Cessation
- 1997-09-09 JP JP51566798A patent/JP2001506231A/ja not_active Ceased
- 1997-09-09 DE DE69734720T patent/DE69734720T2/de not_active Expired - Fee Related
- 1997-09-09 SG SG200001995A patent/SG109418A1/en unknown
- 1997-09-15 AR ARP970104219A patent/AR009783A1/es unknown
- 1997-09-18 PA PA19978438401A patent/PA8438401A1/es unknown
- 1997-09-24 PE PE1997000861A patent/PE110498A1/es not_active Application Discontinuation
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