RU96115179A - CASCADE POLYMERS WITH HYDROGEN CONTAINING AROMATIC HYDROCARBON GROUPS - Google Patents
CASCADE POLYMERS WITH HYDROGEN CONTAINING AROMATIC HYDROCARBON GROUPSInfo
- Publication number
- RU96115179A RU96115179A RU96115179/04A RU96115179A RU96115179A RU 96115179 A RU96115179 A RU 96115179A RU 96115179/04 A RU96115179/04 A RU 96115179/04A RU 96115179 A RU96115179 A RU 96115179A RU 96115179 A RU96115179 A RU 96115179A
- Authority
- RU
- Russia
- Prior art keywords
- denotes
- cooh
- group
- iodine
- necessary
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims 15
- 150000004945 aromatic hydrocarbons Chemical group 0.000 title 1
- 150000002431 hydrogen Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 title 1
- 239000001257 hydrogen Substances 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 25
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 13
- 229910052740 iodine Inorganic materials 0.000 claims 13
- 239000011630 iodine Substances 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims 7
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 7
- 201000002674 obstructive nephropathy Diseases 0.000 claims 6
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical group CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 claims 5
- 210000001787 Dendrites Anatomy 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000002872 contrast media Substances 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- -1 carboxy, sulfo Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 201000011528 vascular disease Diseases 0.000 claims 1
Claims (1)
A - (X)б,
где A обозначает азотсодержащее ядро базисной (основной) мультиплетности "б", причем "б" равно величине 1-8; и
X обозначает состоящий их структурных единиц S и максимально 2n дающих изображение остатков Z остаток, где "n" определяет число генераций и обозначает цифры 1-10;
S обозначает остаток формулы II:
где R и R10 независимо друг от друга, обозначают атом водорода или метильную группу;
w равна величине 1 или 2;
q равно величине 0 или 1; и положения α для 0 ≤ k ≤ n-1 заняты другими структурными единицами и для n-ной генерации заняты остатками Z, причем в случае необходимости не занятые остатками Z положения α заняты остатками -(CO)q-U-COOH, где q имеет вышеуказанное значение и U обозначает простую связь или алкиленовую цепь с количеством атомов углерода вплоть до 6, которая в случае необходимости прерывается 1-2 атомами кислорода и/или в случае необходимости замещена 1-4 гидроксильными группами и/или 1-2 карбоксильными группами, при условии, что максимально 20% положений α заняты этим остатком -(CO)q-U-COOH;
Z обозначает содержащий по меньшей мере одну алифатическую карбоксильную, сульфо- или фосфоновую группу и состоящий из соединительного звена Y и тииодзамещенной ароматической углеводородной группы B, дающий изображение остаток Y - B, причем
Y обозначает группу -CO-; -CONH-; -CSNH-;
-CHR-CHR-CONH- или
где R имеет вышеуказанное значение и R0 обозначает атом водорода; метильную или карбоксиметильную группу;
B обозначает бензольное кольцо
где R1 и R2, каждый независимо друг от друга, обозначают атом водорода, -CONR3R4- или -NR6 COR5 - группу, причем R3 и R4, независимо друг от друга, обозначают атом водорода; замещенную в случае необходимости с помощью 1-5 гидроксильных групп и/или 1-3 C1-C3 - алкоксильных групп и/или 1-3 карбоксильных, сульфо- или фосфоновых групп, линейную или разветвленную или циклическую группу с количеством атомов углерода вплоть до 12;
R3 и R4 вместе с атомом азота образуют 5-ти или 6-ти-членное кольцо, содержащее в случае необходимости атом кислорода, SO2-группу или остаток (N-CO-R7), где R7 имеет значения карбоксильной группы или алкильной группы с количеством атомов углерода вплоть до 12, содержащий в случае необходимости 1-5 гидроксильных групп, 1-3 C1-C3 - алкоксильных групп или 1-3 карбокси-, сульфо- или фосфоновых групп;
R5 обозначает карбоксильную группу или алкильную группу с количеством атомов углерода вплоть до 12, в случае необходимости прерываемую атомом кислорода и/или в случае необходимости замещенную 1-3 карбоксильными, сульфо- или фосфоновыми группами и/или 1-5 гидроксильными группами и/или 1-3 C1-C3 - алкоксильными группами;
R6 обозначает атом водорода или алкильную группу с количеством атомов углерода вплоть до 12, замещенную в случае необходимости 1-3 карбоксильными, сульфо- или фосфоновыми группами и/или в случае необходимости 1-3 гидроксильными группами и/или 1-3 C1-C3 - алкоксильными группами;
причем структурные единицы S должны быть идентичны только для одной генерации;
а также их соли с физиологически приемлемыми органическими и/или неорганическими основаниями, аминокислотами или амидами аминокислот.1. Iodine dendrimeric (with dendrite structure) polymers of general formula I:
A - (X) b ,
where A denotes a nitrogen-containing core of the basic (main) multiplicity "b", with "b" equal to the value of 1-8; and
X denotes consisting of them. structural units S and a maximum of 2 n image residues Z balance, where "n" defines the number of generations and denotes the numbers 1-10;
S denotes a residue of formula II:
where R and R 10 independently of each other, represent a hydrogen atom or a methyl group;
w is equal to 1 or 2;
q is 0 or 1; and α positions for 0 ≤ k ≤ n-1 are occupied by other structural units and for n-th generation are occupied by Z residues, and, if necessary, the α positions not occupied by Z residues are occupied by residues - (CO) q -U-COOH, where q has the above value and U stands for a simple bond or alkylene chain with up to 6 carbon atoms, which is interrupted if necessary by 1-2 oxygen atoms and / or, if necessary, substituted by 1-4 hydroxyl groups and / or 1-2 carboxyl groups, with provided that as many as 20% of the α provisions are occupied by this atcom - (CO) q -U-COOH;
Z denotes containing at least one aliphatic carboxyl, sulfo- or phosphonic group and consisting of a connecting link Y and a thiiodo-substituted aromatic hydrocarbon group B, giving the image the remainder Y - B, and
Y denotes the group -CO-; -CONH-; -CSNH-;
-CHR-CHR-CONH- or
where R has the above meaning and R 0 denotes a hydrogen atom; methyl or carboxymethyl group;
B stands for benzene ring
where R 1 and R 2 , each independently of one another, denote a hydrogen atom, —CONR 3 R 4 - or —NR 6 COR 5 - a group, and R 3 and R 4 , independently of one another, denote a hydrogen atom; substituted if necessary with the help of 1-5 hydroxyl groups and / or 1-3 C 1 -C 3 - alkoxy groups and / or 1-3 carboxyl, sulfo - or phosphonic groups, linear or branched or cyclic group with up to carbon atoms up to 12;
R 3 and R 4 together with the nitrogen atom form a 5 or 6-membered ring containing, if necessary, an oxygen atom, a SO 2 group or a residue (N – CO – R 7 ), where R 7 has the meaning of carboxyl group or an alkyl group with up to 12 carbon atoms, containing, if necessary, 1-5 hydroxyl groups, 1-3 C 1 -C 3 alkoxy groups or 1-3 carboxy, sulfo or phosphonic groups;
R 5 denotes a carboxyl group or an alkyl group with up to 12 carbon atoms, optionally interrupted by an oxygen atom and / or optionally substituted with 1-3 carboxyl, sulfo or phosphonic groups and / or 1-5 hydroxyl groups and / or 1-3 C 1 -C 3 - alkoxy groups;
R 6 denotes a hydrogen atom or an alkyl group with up to 12 carbon atoms, substituted if necessary by 1-3 carboxyl, sulfo or phosphonic groups and / or, if necessary, 1-3 hydroxyl groups and / or 1-3 C 1 - C 3 - alkoxy groups;
moreover, the structural units S must be identical for only one generation;
as well as their salts with physiologically acceptable organic and / or inorganic bases, amino acids or amides of amino acids.
где R8 и R9, независимо друг от друга, обозначают линейный или разветвленный алкильный, арильный или аралкильный остаток с количеством атомов углерода вплоть до 20, который в случае необходимости замещен 1-4 гидроксильными группами;
β обозначает место связи с остатком Х, причем число β должно быть равно базисной мультиплетности б;
V обозначает линейный или разветвленный алкиленовый, ариленовый или аралкиленовый остаток с количеством атомов углерода вплоть до 20, который в случае необходимости прерывается 1-4 атомами кислорода и/или замещен 1-4 гидроксильными группами;
r равно 1, 2 или 3;
w равно 1 или 2 и
m равно 0, 1, 2 или 3.2. Iodine-containing dendrimeric polymers according to claim 1, characterized in that core A is a nitrogen atom, a residue β - NR 8 -β, β - NR 8 R 9 or a residue of general formulas III, IV, V or VI:
where R 8 and R 9 , independently of one another, denote a linear or branched alkyl, aryl or aralkyl residue with up to 20 carbon atoms, which is optionally substituted with 1-4 hydroxyl groups;
β denotes the place of connection with the remainder X, and the number β must be equal to the base multiplicity b;
V denotes a linear or branched alkylene, arylene or aralkylene residue with up to 20 carbon atoms, which, if necessary, is interrupted by 1-4 oxygen atoms and / or substituted by 1-4 hydroxyl groups;
r is 1, 2 or 3;
w is 1 or 2 and
m is 0, 1, 2 or 3.
4. Иодсодержащие дендримерные полимеры по пп. 1 и 2, отличающиеся тем, что S обозначает: -CH(CH3)CH(CH3)CONH-CH2-CH2-N; -CH(CH3)CH(CH3)CH2N; -CH2CH2CH2N; -CH2CH(CH3)CH2-N; -CH2CH2-CONH-CH2CH2-N; -CH(CH3)CH2CH2N;
-CH(CH3)CH2CONH-CH2CH2-N; -CH2CH(CH3)CONH-CH2CH2-N.3. Iodine-containing dendrimeric polymers according to claim 1 or 2, characterized in that core A denotes a group β 2 N (CH 2 ) 2 Nβ 2 ; βN (CH 2 CH 2 Nβ 2 ) 2 N (CH 2 CH 2 Nβ 2 ) 3 ;
4. Iodine-containing dendrimeric polymers on PP. 1 and 2, characterized in that S denotes: -CH (CH 3 ) CH (CH 3 ) CONH-CH 2 -CH 2 -N; -CH (CH 3 ) CH (CH 3 ) CH 2 N; —CH 2 CH 2 CH 2 N; —CH 2 CH (CH 3 ) CH 2 —N; —CH 2 CH 2 —CONH — CH 2 CH 2 —N; -CH (CH 3 ) CH 2 CH 2 N;
—CH (CH 3 ) CH 2 CONH — CH 2 CH 2 —N; -CH 2 CH (CH 3 ) CONH-CH 2 CH 2 -N.
CONHCH2CH2SO3H; CON(CH2CH2SO3H);
7. Иодсодержащие дендримерные полимеры по пп. 1 и 2, отличающиеся тем, что R1, соответственно R2, обозначает группу NHCO(CH2)2-COOH; NHCOCOOH; NHCOCH2OCH2COOH; NHCOCH2OCH3; N(CH2COOH)COCH2OCH3; NHCOCH3; N(CH3)COCH2OCH3. 8. Иодсодержащие дендримерные полимеры по пп 1 и 2, отличающиеся тем, что V обозначает группу: -(CH2)4)-; -CH2-C6H4-CH2-; -(CH2)2; -(CH2)2-O-(CH2)2-O-(CH2)2-; -CH2CHOHCH2-; -(CH2)2-O-(CH2)2-.6. Iodine-containing dendrimeric polymers on PP. 1 and 2, characterized in that R 1 , respectively, R 2 , denotes the group: CONH 2 ; CONHCH 2 COOH; CON (CH 2 COOH) 2 ; CONHCH 2 CH (OH) CH 2 OH; CON (CH 3 ) CH 2 COOH; CONHCH 2 PO 3 H 2 ; CON (CH 2 PO 3 H 2 ) 2 ; CON (CH 2 COOH) CH 2 PO 3 H 2 ; CON (CH 3 ) CH 2 CH (OH) CH 2 OH;
CONHCH 2 CH 2 SO 3 H; CON (CH 2 CH 2 SO 3 H);
7. Iodine-containing dendrimeric polymers on PP. 1 and 2, characterized in that R 1 , respectively, R 2 , denotes the group NHCO (CH 2 ) 2 -COOH; NHCOCOOH; NHCOCH 2 OCH 2 COOH; NHCOCH 2 OCH 3 ; N (CH 2 COOH) COCH 2 OCH 3 ; NHCOCH 3 ; N (CH 3 ) COCH 2 OCH 3 . 8. Iodine-containing dendrimeric polymers in PP 1 and 2, characterized in that V denotes a group: - (CH 2 ) 4 ) -; -CH 2 -C 6 H 4 -CH 2 -; - (CH 2 ) 2 ; - (CH 2 ) 2 -O- (CH 2 ) 2 -O- (CH 2 ) 2 -; -CH 2 CHOHCH 2 -; - (CH 2 ) 2 -O- (CH 2 ) 2 -.
A - (X')б,
где A и б имеют указанное в пп. 1 и 2 значение;
X' имеет указанное для X в п. 1 значение, причем, однако, в отличие от X, для n-ной генерации положения α заняты не остатками Z и в случае необходимости -(CO)q-U-COOH, а атомами водорода, вводят во взаимодействие с соединениями общей формулы II
Y' - B',
где Y' обозначает остаток, содержащий карбонильную, тиокарбонильную, активированную карбонильную или CHR = CR - группу, где R имеет значение атома водорода или метильной группы, и превращаемый в Y;
B' имеет указанное для B значение трииодзамещенной ароматической углеводородной группы, причем содержащиеся в B карбоксильные и гидроксильные группы, однако, находятся в защищенной форме;
и затем, в случае необходимости, не занятые остатками Z положения α, ацилируют, соответственно, алкилируют с помощью вводящего остаток -(CO)q-U-COOH реагента.10. The method of obtaining iodine-containing dendrimeric polymers on PP. 1 and 2, characterized in that the dendrimeric polymers of General formula I '
A - (X ') b ,
where A and b are specified in paragraphs. 1 and 2 value;
X 'has the value indicated for X in item 1, and, in contrast to X, for the nth generation, the α position is occupied not by the Z residues and, if necessary, by (CO) q -U-COOH, but by hydrogen atoms, enter into interaction with compounds of the general formula II
Y '- B',
where Y 'denotes a residue containing a carbonyl, thiocarbonyl, activated carbonyl or CHR = CR - group, where R has the meaning of a hydrogen atom or a methyl group, and turns into Y;
B ′ has the tri-substituted aromatic hydrocarbon group indicated for B, the carboxy and hydroxyl groups contained in B, however, being in protected form;
and then, if necessary, the α positions that are not occupied by residues Z, are acylated, respectively, alkylated with a residue introducing - (CO) q -U-COOH reagent.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4344464A DE4344464A1 (en) | 1993-12-22 | 1993-12-22 | Cascade polymers with iodine aromatics |
DEP4344464.4 | 1993-12-22 | ||
PCT/EP1994/004245 WO1995017448A2 (en) | 1993-12-22 | 1994-12-21 | Cascade polymers with iodine aromatic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
RU96115179A true RU96115179A (en) | 1998-10-20 |
RU2147592C1 RU2147592C1 (en) | 2000-04-20 |
Family
ID=6506208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU96115179A RU2147592C1 (en) | 1993-12-22 | 1994-12-21 | Iodine-containing dendrimeric polymers, method of preparing thereof, and diagnostic agent for x-ray diagnostics |
Country Status (24)
Country | Link |
---|---|
US (1) | US5593660A (en) |
EP (1) | EP0736056B1 (en) |
JP (1) | JP3696620B2 (en) |
KR (1) | KR100339447B1 (en) |
CN (1) | CN1075388C (en) |
AT (1) | ATE217330T1 (en) |
AU (1) | AU690189B2 (en) |
CZ (1) | CZ291539B6 (en) |
DE (2) | DE4344464A1 (en) |
DK (1) | DK0736056T5 (en) |
ES (1) | ES2177624T3 (en) |
HU (1) | HU221517B (en) |
IL (1) | IL112128A (en) |
MY (1) | MY112125A (en) |
NO (1) | NO312037B1 (en) |
NZ (1) | NZ278380A (en) |
PL (1) | PL177795B1 (en) |
PT (1) | PT736056E (en) |
RU (1) | RU2147592C1 (en) |
SK (1) | SK284111B6 (en) |
TW (1) | TW380143B (en) |
UA (1) | UA54370C2 (en) |
WO (1) | WO1995017448A2 (en) |
ZA (1) | ZA9410290B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4344460A1 (en) * | 1993-12-22 | 1995-06-29 | Schering Ag | Metal complexes of dendrimeric macromolecules, diagnostic agents containing them and methods for producing the complexes and agents |
DE4425857A1 (en) * | 1994-07-07 | 1996-01-11 | Schering Ag | Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them |
US5756066A (en) * | 1995-06-07 | 1998-05-26 | Schering Aktiengesellschaft | Iodine-containing peptides |
DE19525924A1 (en) * | 1995-07-04 | 1997-01-09 | Schering Ag | Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them |
US6166200A (en) * | 1995-07-04 | 2000-12-26 | Schering Aktiengesellschaft | Cascade polymer complexes, process for their production and pharmaceutical agents containing said complexes |
WO1998006691A2 (en) | 1996-08-14 | 1998-02-19 | Warner-Lambert Company | Low molecular weight dendritic compounds as pharmaceutical agents |
DE10214217A1 (en) * | 2002-03-22 | 2003-10-09 | Schering Ag | Dendritic cascade polymers with hydrophilic iodineDendritic cascade polymers with hydrophilic iodine containing aromatics useful for preparation of X- containing aromatics useful for preparation of X-ray diagnostic agents for vascular diseases and foray diagnostic agents for vascular diseases and for cancer diagnosis r cancer diagnosis |
US20070073004A1 (en) * | 2003-09-12 | 2007-03-29 | Dendritic Nanotechnologies Inc. | Hyperbranched (pamam) polymers via a one pot process |
US8703113B2 (en) * | 2004-07-08 | 2014-04-22 | Reva Medical Inc. | Side-chain crystallizable polymers for medical applications |
MX2012005021A (en) * | 2009-10-29 | 2012-06-19 | Ge Healthcare As | Diagnostic composition comprising plasma cations having superior safety profile. |
KR101585751B1 (en) * | 2010-07-12 | 2016-01-14 | 지이 헬스케어 에이에스 | X-ray imaging at low contrast agent concentrations and/or low dose radiation |
US11213596B2 (en) | 2018-03-12 | 2022-01-04 | Boston Scientific Scimed, Inc. | Radiocontrast agents, scavenging methods, and scavenging system |
CN116425417A (en) * | 2023-04-17 | 2023-07-14 | 揭阳市栢轩顺陶瓷有限公司 | Antifouling and antibacterial porcelain glaze and preparation process thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5364613A (en) * | 1989-04-07 | 1994-11-15 | Sieving Paul F | Polychelants containing macrocyclic chelant moieties |
DE3938992A1 (en) * | 1989-11-21 | 1991-05-23 | Schering Ag | Cascade polymer-bound complex formers, their complexes and conjugates, process for their preparation and pharmaceutical compositions containing them |
EP0616538B1 (en) * | 1991-12-04 | 1999-04-21 | Guerbet S.A. | Novel macromolecular polyamine iodine-containing compound, process for its preparation and its use as a contrast agent |
DE4139962A1 (en) * | 1991-12-04 | 1993-06-09 | Basf Ag, 6700 Ludwigshafen, De | BLOCK COPOLYMERS FROM ACRYLATE AND METHACRYLATE UNITS |
EP0575596B2 (en) * | 1992-01-13 | 2001-05-16 | Dsm N.V. | Dendritic macromolecule and the preparation thereof |
FR2703055B1 (en) * | 1993-03-22 | 1995-07-07 | Guerbet Sa | New polyiodinated compounds, their preparation and their use as contrast agents for radiology. |
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1993
- 1993-12-22 DE DE4344464A patent/DE4344464A1/en not_active Withdrawn
-
1994
- 1994-12-12 TW TW083111570A patent/TW380143B/en not_active IP Right Cessation
- 1994-12-21 DE DE59410117T patent/DE59410117D1/en not_active Expired - Lifetime
- 1994-12-21 UA UA96062448A patent/UA54370C2/en unknown
- 1994-12-21 NZ NZ278380A patent/NZ278380A/en unknown
- 1994-12-21 ES ES95905095T patent/ES2177624T3/en not_active Expired - Lifetime
- 1994-12-21 WO PCT/EP1994/004245 patent/WO1995017448A2/en active IP Right Grant
- 1994-12-21 CN CN94194548A patent/CN1075388C/en not_active Expired - Fee Related
- 1994-12-21 EP EP95905095A patent/EP0736056B1/en not_active Expired - Lifetime
- 1994-12-21 DK DK95905095T patent/DK0736056T5/en active
- 1994-12-21 PT PT95905095T patent/PT736056E/en unknown
- 1994-12-21 RU RU96115179A patent/RU2147592C1/en not_active IP Right Cessation
- 1994-12-21 HU HU9601726A patent/HU221517B/en not_active IP Right Cessation
- 1994-12-21 PL PL94315145A patent/PL177795B1/en not_active IP Right Cessation
- 1994-12-21 SK SK803-96A patent/SK284111B6/en unknown
- 1994-12-21 US US08/360,934 patent/US5593660A/en not_active Expired - Fee Related
- 1994-12-21 AT AT95905095T patent/ATE217330T1/en not_active IP Right Cessation
- 1994-12-21 KR KR1019960703331A patent/KR100339447B1/en not_active IP Right Cessation
- 1994-12-21 JP JP51718695A patent/JP3696620B2/en not_active Expired - Fee Related
- 1994-12-21 CZ CZ19961652A patent/CZ291539B6/en not_active IP Right Cessation
- 1994-12-21 AU AU13845/95A patent/AU690189B2/en not_active Ceased
- 1994-12-21 MY MYPI94003446A patent/MY112125A/en unknown
- 1994-12-22 ZA ZA9410290A patent/ZA9410290B/en unknown
- 1994-12-22 IL IL11212894A patent/IL112128A/en not_active IP Right Cessation
-
1996
- 1996-06-21 NO NO19962662A patent/NO312037B1/en unknown
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