DE2439284C2 - 2-Phenyl-3-amino-4-acetyl-5-methylpyrrol, dessen Salze und diese Verbindungen enthaltende pharmazeutische Zubereitung - Google Patents
2-Phenyl-3-amino-4-acetyl-5-methylpyrrol, dessen Salze und diese Verbindungen enthaltende pharmazeutische ZubereitungInfo
- Publication number
- DE2439284C2 DE2439284C2 DE2439284A DE2439284A DE2439284C2 DE 2439284 C2 DE2439284 C2 DE 2439284C2 DE 2439284 A DE2439284 A DE 2439284A DE 2439284 A DE2439284 A DE 2439284A DE 2439284 C2 DE2439284 C2 DE 2439284C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- salts
- acetyl
- methylpyrrole
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LNHXCTFGBVFGMW-UHFFFAOYSA-N 1-(4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N LNHXCTFGBVFGMW-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 title description 17
- 150000003839 salts Chemical class 0.000 title description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 14
- 208000025865 Ulcer Diseases 0.000 description 13
- 230000036269 ulceration Effects 0.000 description 11
- 241000700159 Rattus Species 0.000 description 7
- 229960000905 indomethacin Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- JTIHSSVKTWPPHI-UHFFFAOYSA-N 2-amino-2-phenylacetonitrile Chemical compound N#CC(N)C1=CC=CC=C1 JTIHSSVKTWPPHI-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 acetate Cyclohexylsulfonate Chemical compound 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010062065 Perforated ulcer Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KGEVRRIKSHIGCE-UHFFFAOYSA-N 1-(4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)ethanone;hydrochloride Chemical compound [Cl-].CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1[NH3+] KGEVRRIKSHIGCE-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- NKPPORKKCMYYTO-DHZHZOJOSA-N cinmetacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)\C=C\C1=CC=CC=C1 NKPPORKKCMYYTO-DHZHZOJOSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- C07D207/36—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3979073A GB1427945A (en) | 1973-08-22 | 1973-08-22 | Aminopyrrole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2439284A1 DE2439284A1 (de) | 1975-03-06 |
| DE2439284C2 true DE2439284C2 (de) | 1982-07-29 |
Family
ID=10411528
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462966A Expired DE2462966C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 3-Amino-4-acetyl-5-methylpyrrols und diese enthaltende pharmazeutische Zubereitungen |
| DE2462967A Expired DE2462967C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 3-Amino-5-methyl-2-phenyl-pyrrols, deren Salze und diese enthaltende pharmazeutische Zubereitung |
| DE2462963A Expired DE2462963C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 2-Phenyl-3-amino-pyrrols deren Salze und diese enthaltende pharmazeutische Zubereitung |
| DE2439284A Expired DE2439284C2 (de) | 1973-08-22 | 1974-08-16 | 2-Phenyl-3-amino-4-acetyl-5-methylpyrrol, dessen Salze und diese Verbindungen enthaltende pharmazeutische Zubereitung |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462966A Expired DE2462966C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 3-Amino-4-acetyl-5-methylpyrrols und diese enthaltende pharmazeutische Zubereitungen |
| DE2462967A Expired DE2462967C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 3-Amino-5-methyl-2-phenyl-pyrrols, deren Salze und diese enthaltende pharmazeutische Zubereitung |
| DE2462963A Expired DE2462963C2 (de) | 1973-08-22 | 1974-08-16 | Derivate des 2-Phenyl-3-amino-pyrrols deren Salze und diese enthaltende pharmazeutische Zubereitung |
Country Status (27)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492663A (en) * | 1975-02-20 | 1977-11-23 | Lepetit Spa | 4-amino-3-pyrrole carboxamides |
| GB1548398A (en) * | 1975-06-05 | 1979-07-11 | Lilly Industries Ltd | Acylamino pyrroles furans and thiophenes |
| DE3212591A1 (de) * | 1982-04-03 | 1983-10-13 | Gödecke AG, 1000 Berlin | 2-pyrrolin-3-carbonitril-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPH0216740U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-07-21 | 1990-02-02 | ||
| US5155152A (en) * | 1989-03-28 | 1992-10-13 | Ciba-Geigy Corporation | Substitute aminopyrroles as stabilizers for chlorine-containing polymers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1148908A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Indole derivatives and processes for making them |
| GB1187903A (en) * | 1967-09-29 | 1970-04-15 | Sumitomo Chemical Co | Glucuronides of 3-Indolylaliphatic Acid Derivatives and Processes for Producing them |
-
1973
- 1973-08-22 GB GB3979073A patent/GB1427945A/en not_active Expired
-
1974
- 1974-07-27 ZA ZA00744754A patent/ZA744754B/xx unknown
- 1974-07-29 IL IL45368A patent/IL45368A/en unknown
- 1974-08-01 YU YU2141/74A patent/YU36926B/xx unknown
- 1974-08-08 NO NO742862A patent/NO143845C/no unknown
- 1974-08-08 IE IE1672/74A patent/IE40290B1/en unknown
- 1974-08-16 DE DE2462966A patent/DE2462966C2/de not_active Expired
- 1974-08-16 DE DE2462967A patent/DE2462967C2/de not_active Expired
- 1974-08-16 DE DE2462963A patent/DE2462963C2/de not_active Expired
- 1974-08-16 DE DE2439284A patent/DE2439284C2/de not_active Expired
- 1974-08-16 DD DD180545A patent/DD113756A5/xx unknown
- 1974-08-19 RO RO7491734A patent/RO70534A/ro unknown
- 1974-08-19 RO RO7491735A patent/RO70535A/ro unknown
- 1974-08-19 RO RO79830A patent/RO72882B/ro unknown
- 1974-08-20 IN IN1864/CAL/1974A patent/IN140329B/en unknown
- 1974-08-20 NL NL7411092A patent/NL7411092A/xx unknown
- 1974-08-20 LU LU70764A patent/LU70764A1/xx unknown
- 1974-08-21 DK DK445974A patent/DK156391C/da active
- 1974-08-21 SU SU742055571A patent/SU843738A3/ru active
- 1974-08-21 HU HULE754A patent/HU169728B/hu not_active IP Right Cessation
- 1974-08-21 CA CA207,472A patent/CA1050556A/en not_active Expired
- 1974-08-21 SE SE7410636A patent/SE394429B/xx not_active IP Right Cessation
- 1974-08-21 CH CH1142674A patent/CH605741A5/xx not_active IP Right Cessation
- 1974-08-21 JP JP9600974A patent/JPS5328914B2/ja not_active Expired
- 1974-08-21 FI FI2462/74A patent/FI61879C/fi active
- 1974-08-22 ES ES429446A patent/ES429446A1/es not_active Expired
- 1974-08-22 BE BE147818A patent/BE819088A/xx not_active IP Right Cessation
- 1974-08-22 PL PL1974173617A patent/PL95235B1/pl unknown
- 1974-08-22 FR FR7428894A patent/FR2241308B1/fr not_active Expired
- 1974-08-22 CS CS745833A patent/CS188201B2/cs unknown
- 1974-08-22 AT AT684774A patent/AT336600B/de not_active IP Right Cessation
- 1974-08-22 PL PL1974189700A patent/PL96806B1/pl unknown
- 1974-08-27 AR AR255253A patent/AR210246A1/es active
-
1976
- 1976-06-03 AR AR263503A patent/AR210133A1/es active
- 1976-06-03 AR AR263502A patent/AR210132A1/es active
- 1976-07-01 ES ES449426A patent/ES449426A1/es not_active Expired
- 1976-07-01 ES ES449425A patent/ES449425A1/es not_active Expired
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