FI59803C - Foerfarande foer framstaellning av terapeutiskt anvaendbara penicillansyraderivater - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara penicillansyraderivater Download PDFInfo
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- FI59803C FI59803C FI752924A FI752924A FI59803C FI 59803 C FI59803 C FI 59803C FI 752924 A FI752924 A FI 752924A FI 752924 A FI752924 A FI 752924A FI 59803 C FI59803 C FI 59803C
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- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 52
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 3
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- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- KSCRVOKQPYZBHZ-IXPOFIJOSA-N benzyl n-[(2s)-1-[[(2s)-1-[[(2s)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C[C@H]1C(NCC1)=O)C(=O)C=1SC2=CC=CC=C2N=1)C(C)C)C(=O)OCC1=CC=CC=C1 KSCRVOKQPYZBHZ-IXPOFIJOSA-N 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 description 1
- 229960001585 dicloxacillin Drugs 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- HSNUXDIQZKIQRR-UHFFFAOYSA-N hydroxy-imino-bis(phenylmethoxy)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1COP(=O)(N)OCC1=CC=CC=C1 HSNUXDIQZKIQRR-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ADNODBYTFORIQQ-UHFFFAOYSA-N isocyanatophosphonic acid Chemical compound OP(O)(=O)N=C=O ADNODBYTFORIQQ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 1
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 description 1
- 229960000515 nafcillin Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000005541 phosphonamide group Chemical group 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960004932 sulbenicillin Drugs 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2487—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-C(=X) (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4484—Compounds containing the structure C-P(=X)(N-acyl)-X, C-P(=X)(N-heteroatom)-X or C-P(=X)(N-CN)-X (X = O, S, Se)
- C07F9/4492—Compounds containing the structure P(=X)(N-C(=X)-) (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI803000A FI803000A (fi) | 1974-10-21 | 1980-09-24 | Mellanprodukter anvaendbara foer framstaellning av penicillansyraderivater |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45480/74A GB1523278A (en) | 1974-10-21 | 1974-10-21 | Penicillanic acid derivatives |
| GB4548074 | 1974-10-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752924A FI752924A (nl) | 1976-04-22 |
| FI59803B FI59803B (fi) | 1981-06-30 |
| FI59803C true FI59803C (fi) | 1981-10-12 |
Family
ID=10437377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752924A FI59803C (fi) | 1974-10-21 | 1975-10-20 | Foerfarande foer framstaellning av terapeutiskt anvaendbara penicillansyraderivater |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4067986A (nl) |
| JP (2) | JPS5165793A (nl) |
| AT (1) | AT349631B (nl) |
| BE (1) | BE834679A (nl) |
| CS (1) | CS203096B2 (nl) |
| DE (1) | DE2546910C3 (nl) |
| DK (1) | DK471375A (nl) |
| ES (2) | ES441922A1 (nl) |
| FI (1) | FI59803C (nl) |
| FR (1) | FR2288526A1 (nl) |
| GB (1) | GB1523278A (nl) |
| HU (1) | HU170700B (nl) |
| IE (1) | IE42612B1 (nl) |
| IT (1) | IT1047205B (nl) |
| LU (1) | LU73606A1 (nl) |
| NL (1) | NL164039C (nl) |
| NO (1) | NO753519L (nl) |
| PL (2) | PL108190B1 (nl) |
| SE (2) | SE7511732L (nl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5283587A (en) * | 1976-01-01 | 1977-07-12 | Gist Brocades Nv | Heterocyclic compound of novel substance |
| US4177189A (en) * | 1977-06-01 | 1979-12-04 | Gist-Brocades N.V. | Process for the preparation of hydroxyphosphinylureidobenzylpenicillins |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1184665A (en) * | 1966-12-28 | 1970-03-18 | Astra Ab | Penicillins |
| GB1241844A (en) * | 1968-08-23 | 1971-08-04 | Beecham Group Ltd | Penicillins |
| US3939149A (en) * | 1970-05-25 | 1976-02-17 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| GB1430074A (en) * | 1972-07-13 | 1976-03-31 | Beecham Group Ltd | Penicillins |
| GB1464551A (en) * | 1973-02-08 | 1977-02-16 | Gist Brocades Nv | Alpha-substituted amino-phenylacetamido penicillanic acid and cephalosporanic acid derivatives methods for their preparation and their use |
| US3935189A (en) * | 1973-05-04 | 1976-01-27 | Beecham Group Limited | Penicillins |
-
1974
- 1974-10-21 GB GB45480/74A patent/GB1523278A/en not_active Expired
-
1975
- 1975-10-18 PL PL1975195778A patent/PL108190B1/pl unknown
- 1975-10-18 PL PL1975184094A patent/PL103373B1/pl unknown
- 1975-10-20 US US05/624,276 patent/US4067986A/en not_active Expired - Lifetime
- 1975-10-20 SE SE7511732A patent/SE7511732L/xx unknown
- 1975-10-20 BE BE161083A patent/BE834679A/xx unknown
- 1975-10-20 AT AT794975A patent/AT349631B/de not_active IP Right Cessation
- 1975-10-20 FI FI752924A patent/FI59803C/fi not_active IP Right Cessation
- 1975-10-20 NL NL7512264.A patent/NL164039C/nl not_active IP Right Cessation
- 1975-10-20 NO NO753519A patent/NO753519L/no unknown
- 1975-10-20 CS CS757049A patent/CS203096B2/cs unknown
- 1975-10-20 DK DK471375A patent/DK471375A/da unknown
- 1975-10-20 JP JP50126238A patent/JPS5165793A/ja active Pending
- 1975-10-20 HU HUGI232A patent/HU170700B/hu unknown
- 1975-10-20 FR FR7532049A patent/FR2288526A1/fr not_active Withdrawn
- 1975-10-20 DE DE2546910A patent/DE2546910C3/de not_active Expired
- 1975-10-20 IT IT69605/75A patent/IT1047205B/it active
- 1975-10-20 IE IE2284/75A patent/IE42612B1/en unknown
- 1975-10-20 ES ES441922A patent/ES441922A1/es not_active Expired
- 1975-10-20 LU LU73606A patent/LU73606A1/xx unknown
-
1976
- 1976-01-12 ES ES444212A patent/ES444212A1/es not_active Expired
-
1977
- 1977-12-28 JP JP15851077A patent/JPS5387393A/ja active Pending
-
1978
- 1978-08-28 SE SE7809050A patent/SE7809050L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5165793A (nl) | 1976-06-07 |
| FI752924A (nl) | 1976-04-22 |
| DE2546910C3 (de) | 1978-09-28 |
| ES441922A1 (es) | 1977-03-16 |
| US4067986A (en) | 1978-01-10 |
| FI59803B (fi) | 1981-06-30 |
| LU73606A1 (nl) | 1977-05-24 |
| PL108190B1 (pl) | 1980-03-31 |
| ES444212A1 (es) | 1977-05-01 |
| NL7512264A (nl) | 1976-04-23 |
| CS203096B2 (en) | 1981-02-27 |
| DE2546910A1 (de) | 1976-04-22 |
| JPS5387393A (en) | 1978-08-01 |
| AT349631B (de) | 1979-04-10 |
| IT1047205B (it) | 1980-09-10 |
| PL103373B1 (pl) | 1979-06-30 |
| GB1523278A (en) | 1978-08-31 |
| SE7809050L (sv) | 1978-08-28 |
| SE7511732L (sv) | 1976-04-22 |
| HU170700B (nl) | 1977-08-28 |
| NO753519L (nl) | 1976-04-22 |
| FR2288526A1 (fr) | 1976-05-21 |
| ATA794975A (de) | 1978-09-15 |
| IE42612L (en) | 1976-04-21 |
| NL164039C (nl) | 1980-11-17 |
| IE42612B1 (en) | 1980-09-10 |
| DK471375A (da) | 1976-04-22 |
| NL164039B (nl) | 1980-06-16 |
| DE2546910B2 (de) | 1978-02-23 |
| BE834679A (fr) | 1976-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: GIST-BROCADES B.V. |