FI68042C - 5-amino-2,4,6-trijod-isoftalsyra-bis-amid-derivat foer anvaendning i roentgenkontrastmedel - Google Patents
5-amino-2,4,6-trijod-isoftalsyra-bis-amid-derivat foer anvaendning i roentgenkontrastmedel Download PDFInfo
- Publication number
- FI68042C FI68042C FI802215A FI802215A FI68042C FI 68042 C FI68042 C FI 68042C FI 802215 A FI802215 A FI 802215A FI 802215 A FI802215 A FI 802215A FI 68042 C FI68042 C FI 68042C
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- Finland
- Prior art keywords
- bis
- amino
- acid
- formula
- triiodo
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- -1 hydroxy, methoxy Chemical group 0.000 claims abstract description 49
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000002872 contrast media Substances 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 229940039231 contrast media Drugs 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000001470 diamides Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006698 hydrazinolysis reaction Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 4
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims 2
- 101001061911 Homo sapiens Ras-related protein Rab-40A Proteins 0.000 claims 1
- 102100029553 Ras-related protein Rab-40A Human genes 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 42
- 238000000354 decomposition reaction Methods 0.000 description 35
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 29
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- 238000006243 chemical reaction Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- FUOXCOHIWKJOMU-UHFFFAOYSA-N 5-[(2-aminoacetyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I FUOXCOHIWKJOMU-UHFFFAOYSA-N 0.000 description 12
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 11
- ASBGVYOIJLROJS-UHFFFAOYSA-N 5-[(2-chloroacetyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(I)C(NC(=O)CCl)=C(I)C(C(O)=O)=C1I ASBGVYOIJLROJS-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
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- 238000001816 cooling Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
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- 239000011541 reaction mixture Substances 0.000 description 5
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- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
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- HWPJOWDGPXJRRY-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-4,6-diiodo-2-[(2-iodoacetyl)amino]benzene-1,3-dicarboxylic acid Chemical compound ICC(=O)NC1=C(C(=O)O)C(=C(C(=C1C(=O)O)I)N1C(C=2C(C1=O)=CC=CC=2)=O)I HWPJOWDGPXJRRY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- SHWNNYZBHZIQQV-UHFFFAOYSA-J EDTA monocalcium diisodium salt Chemical compound [Na+].[Na+].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O SHWNNYZBHZIQQV-UHFFFAOYSA-J 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
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- GEBVOUQKIMSWJH-UHFFFAOYSA-N 5-(3-aminopropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NCCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GEBVOUQKIMSWJH-UHFFFAOYSA-N 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- VVDGWALACJEJKG-UHFFFAOYSA-N iodamide Chemical compound CC(=O)NCC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I VVDGWALACJEJKG-UHFFFAOYSA-N 0.000 description 1
- 229960004901 iodamide Drugs 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229960000929 iotalamic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229940083604 sodium iothalamate Drugs 0.000 description 1
- WCIMWHNSWLLELS-ZMWPDAOESA-M sodium;3-acetamido-2,6-bis(iodanyl)-4-iodo-5-(methylcarbamoyl)benzoate Chemical compound [Na+].CNC(=O)C1=C(I)C(NC(C)=O)=C([125I])C(C([O-])=O)=C1[125I] WCIMWHNSWLLELS-ZMWPDAOESA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- ZEGFMFQPWDMMEP-UHFFFAOYSA-N strontium;sulfide Chemical compound [S-2].[Sr+2] ZEGFMFQPWDMMEP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Dental Preparations (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2928417 | 1979-07-12 | ||
| DE19792928417 DE2928417A1 (de) | 1979-07-12 | 1979-07-12 | Trijodierte basen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802215A FI802215A (fi) | 1981-01-13 |
| FI68042B FI68042B (fi) | 1985-03-29 |
| FI68042C true FI68042C (fi) | 1985-07-10 |
Family
ID=6075678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802215A FI68042C (fi) | 1979-07-12 | 1980-07-10 | 5-amino-2,4,6-trijod-isoftalsyra-bis-amid-derivat foer anvaendning i roentgenkontrastmedel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4283381A (no) |
| EP (1) | EP0022744B1 (no) |
| JP (1) | JPS5659717A (no) |
| AT (1) | ATE2834T1 (no) |
| AU (1) | AU536426B2 (no) |
| CA (1) | CA1129438A (no) |
| CS (1) | CS214834B2 (no) |
| DE (2) | DE2928417A1 (no) |
| DK (1) | DK154501C (no) |
| EG (1) | EG14884A (no) |
| ES (2) | ES493302A0 (no) |
| FI (1) | FI68042C (no) |
| GR (1) | GR69303B (no) |
| HU (1) | HU182154B (no) |
| IE (1) | IE50064B1 (no) |
| IL (1) | IL60517A (no) |
| NO (1) | NO150719C (no) |
| PH (1) | PH16651A (no) |
| PT (1) | PT71547A (no) |
| YU (1) | YU177980A (no) |
| ZA (1) | ZA804192B (no) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3038853A1 (de) | 1980-10-10 | 1982-05-27 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
| DE3150917A1 (de) * | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | "2-amino-1-(1,3-dioxolan-4-yl)-ethanol-verbindungen, deren herstellung und verwendung zur weiterverarbeitung" |
| FR2541676A1 (fr) * | 1983-02-25 | 1984-08-31 | Guerbet Sa | Composes non-ioniques a structures benzenique iodee ou bromee et produits opacifiants en contenant |
| GB8906130D0 (en) * | 1989-03-17 | 1989-05-04 | Nycomed As | Compositions |
| US5232685A (en) * | 1989-11-03 | 1993-08-03 | Schering Aktiengesellschaft | Nonionic x-ray contrast medium with high iodine content |
| IL96324A (en) * | 1989-11-29 | 1995-01-24 | Squibb & Sons Inc | 5-Amino-2, 4, 6-triiodo-1, 3-benzenecarboxylic acid derivatives, processes for their preparation, and methods utilizing them as contrast agents |
| US5614638A (en) * | 1989-11-29 | 1997-03-25 | Bracco International B.V. | Nonionic radiographic contrast agents |
| GB9020091D0 (en) * | 1990-09-14 | 1990-10-24 | Nycomed As | Contrast media |
| US5278311A (en) * | 1992-06-05 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Nonionic radiographic contrast agents |
| JPH10505851A (ja) * | 1994-09-22 | 1998-06-09 | ゲルベ・ソシエテ・アノニム | ポリヨウ素化化合物、その製法、およびｘ線放射線医学におけるその使用 |
| IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| IT1312569B1 (it) * | 1999-05-21 | 2002-04-22 | Raffaele Ansovini | Uso dell'enzima gssg reduttasi per il trattamento terapeutico e laprofilassi di pazienti infettati da hiv. |
| US7790141B2 (en) * | 2003-08-11 | 2010-09-07 | Pathak Holdings, Llc | Radio-opaque compounds, compositions containing same and methods of their synthesis and use |
| CN101654417B (zh) * | 2009-09-01 | 2012-06-20 | 江苏省原子医学研究所 | X线造影剂碘佛醇中间体的制备方法 |
| CN105461581A (zh) * | 2015-11-17 | 2016-04-06 | 浙江海洲制药有限公司 | 碘帕醇杂质a和杂质b的合成方法 |
| CN115806498B (zh) * | 2021-09-15 | 2024-09-10 | 大道隆达（北京）医药科技发展有限公司 | 5-氯乙酰胺基-2,4,6-三碘异酞酰氯的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776241A (en) * | 1952-08-06 | 1957-01-01 | Schering Ag | Injectable x-ray contrast agents comprising salts of n-acyl derivatives of 2, 4, 6-triiodo-3-aminobenzoic acid |
| US3178473A (en) * | 1962-03-02 | 1965-04-13 | Nyegaard & Co As | Process for the n-alkylation of acyl anilides halogen substituted in the nucleus |
| US4021481A (en) * | 1969-06-27 | 1977-05-03 | Nyegaard & Co. A/S | Amido derivatives of 2,4,6-triiodobenzoic acids containing at least one N-hydroxyalkyl and at least two hydroxyl groups |
| IE34927B1 (en) * | 1969-06-27 | 1975-10-01 | Nyegaard & Co As | Non-ionic iodinated x-ray contrast agents |
| BE795555A (fr) * | 1972-02-16 | 1973-08-16 | Schering Ag | Amides de triiodo-isophtaloyl-monoamino-acide, leur procede de preparation et leur utilisation |
| GB1548594A (en) * | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
| US4192859A (en) * | 1978-09-29 | 1980-03-11 | E. R. Squibb & Sons, Inc. | Contrast media containing liposomes as carriers |
-
1979
- 1979-07-12 DE DE19792928417 patent/DE2928417A1/de not_active Withdrawn
-
1980
- 1980-06-27 EP EP80730043A patent/EP0022744B1/de not_active Expired
- 1980-06-27 AT AT80730043T patent/ATE2834T1/de not_active IP Right Cessation
- 1980-06-27 DE DE8080730043T patent/DE3062428D1/de not_active Expired
- 1980-07-08 IL IL60517A patent/IL60517A/xx unknown
- 1980-07-10 CA CA355,900A patent/CA1129438A/en not_active Expired
- 1980-07-10 YU YU01779/80A patent/YU177980A/xx unknown
- 1980-07-10 PH PH24273A patent/PH16651A/en unknown
- 1980-07-10 GR GR62426A patent/GR69303B/el unknown
- 1980-07-10 FI FI802215A patent/FI68042C/fi not_active IP Right Cessation
- 1980-07-10 CS CS804924A patent/CS214834B2/cs unknown
- 1980-07-10 AU AU60294/80A patent/AU536426B2/en not_active Ceased
- 1980-07-11 IE IE1441/80A patent/IE50064B1/en unknown
- 1980-07-11 PT PT71547A patent/PT71547A/pt unknown
- 1980-07-11 ZA ZA00804192A patent/ZA804192B/xx unknown
- 1980-07-11 NO NO802102A patent/NO150719C/no unknown
- 1980-07-11 JP JP9406480A patent/JPS5659717A/ja active Pending
- 1980-07-11 US US06/167,597 patent/US4283381A/en not_active Expired - Lifetime
- 1980-07-11 ES ES493302A patent/ES493302A0/es active Granted
- 1980-07-11 ES ES493301A patent/ES8104791A1/es not_active Expired
- 1980-07-11 HU HU801748A patent/HU182154B/hu unknown
- 1980-07-11 DK DK300680A patent/DK154501C/da not_active IP Right Cessation
- 1980-07-12 EG EG412/80A patent/EG14884A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0022744B1 (de) | 1983-03-23 |
| DE2928417A1 (de) | 1981-01-29 |
| AU536426B2 (en) | 1984-05-10 |
| US4283381A (en) | 1981-08-11 |
| JPS5659717A (en) | 1981-05-23 |
| ZA804192B (en) | 1981-07-29 |
| ES8104792A1 (es) | 1981-05-16 |
| IE801441L (en) | 1981-01-12 |
| NO150719B (no) | 1984-08-27 |
| EP0022744A3 (en) | 1981-03-11 |
| NO150719C (no) | 1984-12-05 |
| PT71547A (en) | 1980-08-01 |
| EG14884A (en) | 1985-06-30 |
| IL60517A0 (en) | 1980-09-16 |
| DK300680A (da) | 1981-01-13 |
| AU6029480A (en) | 1981-01-15 |
| DK154501C (da) | 1989-04-10 |
| ES493302A0 (es) | 1981-05-16 |
| ES493301A0 (es) | 1981-05-16 |
| FI802215A (fi) | 1981-01-13 |
| ATE2834T1 (de) | 1983-04-15 |
| HU182154B (en) | 1983-12-28 |
| YU177980A (en) | 1983-12-31 |
| GR69303B (no) | 1982-05-14 |
| NO802102L (no) | 1981-01-13 |
| IE50064B1 (en) | 1986-02-05 |
| CS214834B2 (en) | 1982-06-25 |
| IL60517A (en) | 1984-06-29 |
| CA1129438A (en) | 1982-08-10 |
| DE3062428D1 (en) | 1983-04-28 |
| FI68042B (fi) | 1985-03-29 |
| ES8104791A1 (es) | 1981-05-16 |
| EP0022744A2 (de) | 1981-01-21 |
| DK154501B (da) | 1988-11-21 |
| PH16651A (en) | 1983-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SCHERING AKTIENGESELLSCHAFT |