RU95114847A - Heterocyclyl-benzoyl-guanidine, a method for their production, a pharmaceutical position, and a method for its production - Google Patents
Heterocyclyl-benzoyl-guanidine, a method for their production, a pharmaceutical position, and a method for its productionInfo
- Publication number
- RU95114847A RU95114847A RU95114847/04A RU95114847A RU95114847A RU 95114847 A RU95114847 A RU 95114847A RU 95114847/04 A RU95114847/04 A RU 95114847/04A RU 95114847 A RU95114847 A RU 95114847A RU 95114847 A RU95114847 A RU 95114847A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- diaminomethylene
- denotes
- atoms
- heterocyclyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000000969 carrier Substances 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- SVBDQDWHYZUZAF-UHFFFAOYSA-N N-(diaminomethylidene)-2-ethyl-3-methylsulfonyl-4-pyridin-3-ylbenzamide Chemical compound CCC1=C(C(=O)N=C(N)N)C=CC(C=2C=NC=CC=2)=C1S(C)(=O)=O SVBDQDWHYZUZAF-UHFFFAOYSA-N 0.000 claims 1
- YTBJGHKQYDDMGO-UHFFFAOYSA-N N-(diaminomethylidene)-2-ethyl-4-imidazol-1-yl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(N2C=NC=C2)=C1S(C)(=O)=O YTBJGHKQYDDMGO-UHFFFAOYSA-N 0.000 claims 1
- DAQFIYQQCCJXGQ-UHFFFAOYSA-N N-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-(4-oxopyridin-1-yl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(N2C=CC(=O)C=C2)=C1S(C)(=O)=O DAQFIYQQCCJXGQ-UHFFFAOYSA-N 0.000 claims 1
- MINJNLBSTNMFEU-UHFFFAOYSA-N N-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-pyridin-2-ylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(C=2N=CC=CC=2)=C1S(C)(=O)=O MINJNLBSTNMFEU-UHFFFAOYSA-N 0.000 claims 1
- VWRVECUCCWMVJN-UHFFFAOYSA-N N-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-pyridin-3-ylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(C=2C=NC=CC=2)=C1S(C)(=O)=O VWRVECUCCWMVJN-UHFFFAOYSA-N 0.000 claims 1
- DPPXWOYNMZGGCQ-UHFFFAOYSA-N N-(diaminomethylidene)-4-(3-hydroxypiperidin-1-yl)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(N2CC(O)CCC2)=C1S(C)(=O)=O DPPXWOYNMZGGCQ-UHFFFAOYSA-N 0.000 claims 1
- YNSUTRCHDNWBLJ-UHFFFAOYSA-N N-(diaminomethylidene)-4-imidazol-1-yl-3,6-dimethyl-5-sulfonylcyclohexa-1,3-diene-1-carboxamide Chemical compound O=S(=O)=C1C(C)C(C(=O)N=C(N)N)=CC(C)=C1N1C=NC=C1 YNSUTRCHDNWBLJ-UHFFFAOYSA-N 0.000 claims 1
- AJDQRQQNNLZLPM-UHFFFAOYSA-N N-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal cation Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 230000001413 cellular Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Claims (6)
где R1 обозначает A, CF3, CH2F, CHF2, C2F5, CN, NO2, Гал, C ≡ CH или -X-R4;
R2 и R3 каждый, независимо друг от друга, обозначают Н, Гал, А, -X-R4, CN, NO2, CF3, CH2F, CHF2, C2F5, CH2CF3, -SOn-R6, -SO2NR4R5, Ph или OPh;
R4 обозначает Н, А, циклоалкил с 5-7 С-атомами, циклоалкилметил с 6-8 С-атомами, CF3, CH2F, CHF2, CH2CF3, Ph или -CH2-Ph;
R5 обозначает Н или А или R4 и R5 вместе также обозначают алкилен с 4-5 С-атомами, причем одна CH2-группа может быть заменена также на O, S, NH, N-A или N-CH2-Ph;
R6 обозначает А или Ph;
Het обозначает одно- или двухъядерный, насыщенный, ненасыщенный или ароматический гетероцикл с 1-4 N-, O- и/или S-атомами, связанными через N или С, который незамещен или одно-, двух- или трехкратно может быть замещен с помощью Гал, CF3, A, -X-R4, CN, NO2 и/или кислорода карбонила;
А обозначает алкил с 1-6 С-атомами;
Х обозначает О, S или NR5;
Ph обозначает незамещенный или одно-, двух- или трехкратно замещенный с помощью А, ОА, NR4R5, F, Cl, Br, J или CF3 фенил;
n обозначает 1 или 2;
Гал обозначает фтор, хлор, бром или йод;
а также их физиологически приемлемые соли.1. Heterocyclyl-benzoyl-guanidines of the formula I
where R 1 denotes A, CF 3 , CH 2 F, CHF 2 , C 2 F 5 , CN, NO 2 , Gal, C ≡ CH or -XR 4 ;
R 2 and R 3 each, independently of one another, denote H, Gal, A, -XR 4 , CN, NO 2 , CF 3 , CH 2 F, CHF 2 , C 2 F 5 , CH 2 CF 3 , -SO n -R 6 , -SO 2 NR 4 R 5 , Ph or OPh;
R 4 is H, A, cycloalkyl with 5-7 C-atoms, cycloalkylmethyl with 6-8 C-atoms, CF 3 , CH 2 F, CHF 2 , CH 2 CF 3 , Ph or -CH 2 -Ph;
R 5 is H or A or R 4 and R 5 together also represent alkylene with 4-5 C-atoms, and one CH 2 -group can also be replaced with O, S, NH, NA or N-CH 2 -Ph;
R 6 is A or Ph;
Het denotes a single or dual-core, saturated, unsaturated or aromatic heterocycle with 1-4 N-, O- and / or S-atoms linked through N or C, which can be unsubstituted or substituted one-, two- or three-fold with Gal, CF 3 , A, -XR 4 , CN, NO 2 and / or carbonyl oxygen;
And denotes alkyl with 1-6 C-atoms;
X is O, S or NR 5 ;
Ph denotes unsubstituted or one-, two- or three-fold substituted with A, OA, NR 4 R 5 , F, Cl, Br, J, or CF 3 phenyl;
n is 1 or 2;
Gal refers to fluorine, chlorine, bromine or iodine;
and their physiologically acceptable salts.
(а) N-диаминометилен-2-этил-4-(1-имидазолил)-5-метилсульфонилбензамид;
(б) N-диаминометилен-2-метил-4-(1-имидазолил)-5-метилсульфонил-бензамид;
(в) N-диаминометилен-2-метил-4-(3-гидрокси-пиперидино)-5-метилсульфонил-бензамид;
(г) N-диаминометилен-2-этил-4-(3-пиридил)-5-метилсульфонил-бензамид;
(д) N-диаминометилен-2-этил-4-(2-пиридил)-5-метилсульфонил-бензамид;
(е) N-диаминометилен-2-этил-4-(1,4-дигидро-4-оксо-1-пиридил)-5- метилсульфонил-бензамид;
(ж) N-диаминометилен-2-этил-3-метилсульфонил-4-(3-пиридил)-бензамид,
а также их физиологически приемлемые соли.2. Heterocyclyl-benzoyl-guanidines according to claim 1, representing:
(a) N-diaminomethylene-2-ethyl-4- (1-imidazolyl) -5-methylsulfonylbenzamide;
(b) N-diaminomethylene-2-methyl-4- (1-imidazolyl) -5-methylsulfonyl-benzamide;
(c) N-diaminomethylene-2-methyl-4- (3-hydroxy-piperidino) -5-methylsulfonyl-benzamide;
(d) N-diaminomethylene-2-ethyl-4- (3-pyridyl) -5-methylsulfonylbenzamide;
(e) N-diaminomethylene-2-ethyl-4- (2-pyridyl) -5-methylsulfonylbenzamide;
(e) N-diaminomethylene-2-ethyl-4- (1,4-dihydro-4-oxo-1-pyridyl) -5-methylsulfonyl-benzamide;
(g) N-diaminomethylene-2-ethyl-3-methylsulfonyl-4- (3-pyridyl) -benzamide,
and their physiologically acceptable salts.
где R1, R2, R3 и Неt имеют вышеуказанные значения;
Q обозначает Сl, Вr, ОА, О-СО-А, О-СО-Рh, ОН или другую, реакционноспособную, этерифицированную до сложноэфирной ОН-группу, соответственно, легко нуклеофильно замещаемую удаляемую группу,
вводят во взаимодействие с гуанидином; или бензоилгуанидин формулы III
где R1, R2 и R3 имеют вышеуказанные значения, R7 обозначает F, Сl, Вr или J, вводят во взаимодействие с гетероциклическим соединением формулы IV
Неt - D
где Неt имеет вышеуказанное значение,
D обозначает Н; В(ОН)2, триалкилсилил, катион щелочного металла или аммоний, или легко замещаемый металлоорганический остаток, или соответствующее формуле I соединение, которое вместо одного или нескольких атомов водорода содержит одну или несколько восстанавливаемых групп и/или одну или несколько дополнительных С-С- и/или С-N-связей, обрабатывают восстановителем, или соответствующее формуле I соединение, которое вместо одного или нескольких атомов водорода содержит одну или несколько сольволизируемых групп, обрабатывают сольволизирующим средством, и/или полученное основание формул I путем обработки кислотой превращают в одну из его солей.4. The method of obtaining heterocyclyl-benzoylguanidines of the formula I according to claim 1, as well as their salts, characterized in that the compound of formula II
where R 1 , R 2 , R 3 and t have the above values;
Q denotes Cl, Br, OA, O-CO-A, O-CO-Ph, OH, or another, reactive, esterified to ester OH group, respectively, easily nucleophilically replaceable leaving group,
enter into interaction with guanidine; or benzoylguanidine of formula III
where R 1 , R 2 and R 3 have the above values, R 7 denotes F, Cl, Br or J, is introduced into interaction with a heterocyclic compound of formula IV
No - d
where Not has the above meaning,
D is H; In (OH) 2 , a trialkylsilyl, an alkali metal cation or ammonium, or an easily replaceable organometallic residue, or a compound corresponding to formula I, which instead of one or more hydrogen atoms contains one or more reducing groups and / or one or more additional C-C- and / or CNN bonds, are treated with a reducing agent, or a compound corresponding to formula I, which instead of one or several hydrogen atoms contains one or more solvolizable groups, is treated with a solvolysis agent, and / or the obtained base of formulas I is converted into one of its salts by treatment with acid.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4430861.2 | 1994-08-31 | ||
DE4430861A DE4430861A1 (en) | 1994-08-31 | 1994-08-31 | Heterocyclyl-benzoylguanidines |
Publications (2)
Publication Number | Publication Date |
---|---|
RU95114847A true RU95114847A (en) | 1997-08-10 |
RU2152390C1 RU2152390C1 (en) | 2000-07-10 |
Family
ID=6526985
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU95114847/04A RU2152390C1 (en) | 1994-08-31 | 1995-08-30 | Heterocyclyl-benzoylguanidines, method of their synthesis and pharmaceutical composition |
Country Status (22)
Country | Link |
---|---|
US (1) | US5753680A (en) |
EP (1) | EP0699666B1 (en) |
JP (1) | JP4023841B2 (en) |
KR (1) | KR100375788B1 (en) |
CN (1) | CN1058004C (en) |
AT (1) | ATE175406T1 (en) |
AU (1) | AU702258B2 (en) |
BR (1) | BR9503881A (en) |
CA (1) | CA2157146C (en) |
CZ (1) | CZ286400B6 (en) |
DE (2) | DE4430861A1 (en) |
DK (1) | DK0699666T3 (en) |
ES (1) | ES2129716T3 (en) |
GR (1) | GR3029894T3 (en) |
HU (1) | HUT73183A (en) |
NO (1) | NO305798B1 (en) |
PL (1) | PL183393B1 (en) |
RU (1) | RU2152390C1 (en) |
SK (1) | SK281446B6 (en) |
TW (1) | TW354783B (en) |
UA (1) | UA35609C2 (en) |
ZA (1) | ZA957284B (en) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4328352A1 (en) | 1993-08-24 | 1995-03-02 | Hoechst Ag | Substituted N, N'-di-benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them |
ZA967800B (en) * | 1995-09-20 | 1997-04-03 | Yamanouchi Pharma Co Ltd | Heteroaryllsubstituted acryloylguanidine derivatives and pharmaceutical compositions comprising them |
DE19601303A1 (en) * | 1996-01-16 | 1997-07-17 | Boehringer Ingelheim Kg | Novel benzoylguanidine derivatives, process for their preparation and their use in the manufacture of medicaments |
NZ314105A (en) | 1996-02-02 | 1997-12-19 | Sumitomo Pharma | Guanidine derivative substituted with a substituted indole which is peri condensed with a heterocyclic ring |
DE19608162A1 (en) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them |
DE19608161A1 (en) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them |
DE19624178A1 (en) * | 1996-06-18 | 1998-01-08 | Hoechst Ag | Ortho-substituted benzoylguanidines, processes for their preparation, their use as medicaments or diagnostic agents and medicaments containing them |
JP3652708B2 (en) * | 1997-03-06 | 2005-05-25 | トーアエイヨー株式会社 | Cycloalka [b] pyridine-3-carbonylguanidine derivative, process for producing the same, and pharmaceutical containing the same |
DE19738604A1 (en) * | 1997-09-04 | 1999-03-11 | Hoechst Marion Roussel De Gmbh | Use of Na<+>/H<+> exchange inhibitors |
DE19833118C2 (en) * | 1998-07-23 | 2000-07-27 | Merck Patent Gmbh | Process for the preparation of orthoalkylated benzoic acid derivatives |
JP2002530325A (en) * | 1998-11-26 | 2002-09-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Use of benzoylguanidine for the treatment of non-insulin-dependent diabetes mellitus |
DE19859727A1 (en) | 1998-12-23 | 2000-06-29 | Aventis Pharma Gmbh | The use of inhibitors of the sodium-hydrogen exchanger for the manufacture of a medicament for the prevention of age-related organ dysfunctions, age-related illnesses for the prolongation of life |
DE19903275A1 (en) * | 1999-01-28 | 2000-08-03 | Merck Patent Gmbh | Lyophilisates with improved reconstitutability |
DE19919349A1 (en) * | 1999-04-28 | 2000-11-02 | Merck Patent Gmbh | Process for the preparation of a benzoylguanidine derivative |
DE19929857A1 (en) * | 1999-06-29 | 2001-01-04 | Merck Patent Gmbh | Process for the preparation of a 4- (pyrrol-1-yl) benzoylguanidine derivative |
DE19950898A1 (en) | 1999-10-22 | 2001-04-26 | Aventis Pharma Gmbh | New heteroaryl substituted fluoroalkyl-benzoylguanidine derivatives useful for treatment of e.g. ischemias, cardiac infarction, angina, shock, atherosclerosis, cancer and metabolic disorders |
DE10001879A1 (en) * | 2000-01-19 | 2001-07-19 | Aventis Pharma Gmbh | New benzoylguanidine derivatives are Na+/H+ exchange inhibitors useful for the treatment and prevention of e.g. ischemic disorders, infarction, arrhythmia, angina pectoris and stroke |
IL147696A0 (en) * | 2001-01-25 | 2002-08-14 | Pfizer Prod Inc | Combination therapy |
CN101503393B (en) * | 2003-03-13 | 2015-08-19 | 出光兴产株式会社 | Nitrogen-containing heterocyclic derivative and organic electroluminescent element using same |
DE502004007841D1 (en) * | 2003-05-06 | 2008-09-25 | Merck Patent Gmbh | PROCESS FOR CRYSTALLIZING GUANIDINIUM SALTS |
CN101137641B (en) * | 2004-12-27 | 2010-11-24 | 韩国化学研究院 | Benzothiophen-2-carbonylguanidine derivatives, preparation thereof, and pharmaceutical composition containing the same |
CN101119971B (en) * | 2005-02-16 | 2010-09-08 | 东亚荣养株式会社 | Cyclohepta[b]pyridine-3-carbonylguanidine derivative and pharmaceutical product containing same |
CN100371328C (en) * | 2006-01-19 | 2008-02-27 | 中国药科大学 | Substituted benzoyl carbamidine derivative, its preparation method and medical uses |
US20110118262A1 (en) * | 2008-07-08 | 2011-05-19 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and Piperidinyl Compounds Useful as NHE-1 Inhibitiors |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3929582A1 (en) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | BENZOYLGUANIDINE, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS A MEDICINE AND THE MEDICINE CONTAINING IT |
DE59302959D1 (en) * | 1992-02-15 | 1996-07-25 | Hoechst Ag | 3,5-Substituted benzoylguanidines, with antiarrhythmic effects and inhibitory effects on cell proliferation |
ATE158278T1 (en) * | 1992-02-15 | 1997-10-15 | Hoechst Ag | ORTHO-SUBSTITUTED BENZOYLGUANIDINES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS A MEDICATION OR DIAGNOSTIC AND A MEDICINE CONTAINING THEM |
CZ284456B6 (en) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Amino substituted benzylguanidines, process of their preparation and their use for preparing medicaments |
DE4328869A1 (en) * | 1993-08-27 | 1995-03-02 | Hoechst Ag | Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them |
DE4404183A1 (en) * | 1994-02-10 | 1995-08-17 | Merck Patent Gmbh | 4-amino-1-piperidylbenzoylguanidine |
-
1994
- 1994-08-31 DE DE4430861A patent/DE4430861A1/en not_active Withdrawn
-
1995
- 1995-07-21 TW TW084107588A patent/TW354783B/en active
- 1995-08-21 SK SK1029-95A patent/SK281446B6/en unknown
- 1995-08-23 UA UA95083918A patent/UA35609C2/en unknown
- 1995-08-24 DE DE59504721T patent/DE59504721D1/en not_active Expired - Lifetime
- 1995-08-24 AU AU30250/95A patent/AU702258B2/en not_active Ceased
- 1995-08-24 DK DK95113307T patent/DK0699666T3/en active
- 1995-08-24 AT AT95113307T patent/ATE175406T1/en not_active IP Right Cessation
- 1995-08-24 ES ES95113307T patent/ES2129716T3/en not_active Expired - Lifetime
- 1995-08-24 EP EP95113307A patent/EP0699666B1/en not_active Expired - Lifetime
- 1995-08-29 CA CA002157146A patent/CA2157146C/en not_active Expired - Fee Related
- 1995-08-29 CZ CZ19952202A patent/CZ286400B6/en not_active IP Right Cessation
- 1995-08-30 HU HU9502548A patent/HUT73183A/en unknown
- 1995-08-30 RU RU95114847/04A patent/RU2152390C1/en not_active IP Right Cessation
- 1995-08-30 ZA ZA957284A patent/ZA957284B/en unknown
- 1995-08-30 CN CN95116901A patent/CN1058004C/en not_active Expired - Fee Related
- 1995-08-30 US US08/520,780 patent/US5753680A/en not_active Expired - Lifetime
- 1995-08-30 NO NO953404A patent/NO305798B1/en not_active IP Right Cessation
- 1995-08-30 PL PL95310224A patent/PL183393B1/en not_active IP Right Cessation
- 1995-08-31 JP JP24515195A patent/JP4023841B2/en not_active Expired - Fee Related
- 1995-08-31 BR BR9503881A patent/BR9503881A/en not_active Application Discontinuation
- 1995-08-31 KR KR1019950027957A patent/KR100375788B1/en not_active IP Right Cessation
-
1999
- 1999-04-07 GR GR990400985T patent/GR3029894T3/en unknown
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