CA1088945A - Hydantoin derivatives as therapeutic agents - Google Patents
Hydantoin derivatives as therapeutic agentsInfo
- Publication number
- CA1088945A CA1088945A CA287,868A CA287868A CA1088945A CA 1088945 A CA1088945 A CA 1088945A CA 287868 A CA287868 A CA 287868A CA 1088945 A CA1088945 A CA 1088945A
- Authority
- CA
- Canada
- Prior art keywords
- spiro
- dione
- imidazolidine
- hydrogen
- lower alkoxy
- 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
- 150000001469 hydantoins Chemical class 0.000 title abstract description 5
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title 1
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 44
- -1 carbonyl ring compound Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000460 chlorine Chemical group 0.000 claims abstract description 30
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 30
- 239000011737 fluorine Substances 0.000 claims abstract description 28
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001099 ammonium carbonate Substances 0.000 claims abstract description 13
- 235000012501 ammonium carbonate Nutrition 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052794 bromium Chemical group 0.000 claims abstract description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910052717 sulfur Chemical group 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011593 sulfur Chemical group 0.000 claims abstract description 10
- QAHZIGHCEBUNGT-QMGFNSACSA-N (5r,6s,7s,8r,9r)-6,7,8-trihydroxy-9-(hydroxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)C[C@]11C(=O)NC(=O)N1 QAHZIGHCEBUNGT-QMGFNSACSA-N 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 150000001768 cations Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- RVNCABKMTZPRMQ-UHFFFAOYSA-N 6,7-dichlorospiro[2,3-dihydrothiochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C1=2C=C(Cl)C(Cl)=CC=2SCCC21NC(=O)NC2=O RVNCABKMTZPRMQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- VIZLNCBMYFWSNW-UHFFFAOYSA-N 6-fluorospiro[2,3-dihydrothiochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2SCCC21NC(=O)NC2=O VIZLNCBMYFWSNW-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 76
- 230000008569 process Effects 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 9
- 229940091173 hydantoin Drugs 0.000 claims description 7
- LXANPKRCLVQAOG-UHFFFAOYSA-N 6-fluorospiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2OCCC21NC(=O)NC2=O LXANPKRCLVQAOG-UHFFFAOYSA-N 0.000 claims description 6
- SWBBIJZMIGAZHW-UHFFFAOYSA-N 6-fluoro-2,3-dihydrochromen-4-one Chemical compound O1CCC(=O)C2=CC(F)=CC=C21 SWBBIJZMIGAZHW-UHFFFAOYSA-N 0.000 claims description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MRVOWKLMDIJXGZ-UHFFFAOYSA-N 6,7-dichlorospiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C1=2C=C(Cl)C(Cl)=CC=2OCCC21NC(=O)NC2=O MRVOWKLMDIJXGZ-UHFFFAOYSA-N 0.000 claims 2
- LKJWKGASIXMAMT-UHFFFAOYSA-N 6,8-dichlorospiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(Cl)=CC(Cl)=C2OCCC21NC(=O)NC2=O LKJWKGASIXMAMT-UHFFFAOYSA-N 0.000 claims 2
- QFOWEKGSSXHIFQ-UHFFFAOYSA-N 6,7-dichloro-3,4-dihydrothiochromen-2-one Chemical compound ClC=1C=C2CCC(SC2=CC1Cl)=O QFOWEKGSSXHIFQ-UHFFFAOYSA-N 0.000 claims 1
- DNRWXABMOCRPIA-UHFFFAOYSA-N 6,8-dichloro-3,4-dihydrochromen-2-one Chemical compound O1C(=O)CCC2=CC(Cl)=CC(Cl)=C21 DNRWXABMOCRPIA-UHFFFAOYSA-N 0.000 claims 1
- IFSQCXGQIANMIE-UHFFFAOYSA-N 6-fluoro-3,4-dihydrothiochromen-2-one Chemical compound S1C(=O)CCC2=CC(F)=CC=C21 IFSQCXGQIANMIE-UHFFFAOYSA-N 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 abstract description 10
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract description 7
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 abstract description 6
- 208000002249 Diabetes Complications Diseases 0.000 abstract description 5
- 206010012655 Diabetic complications Diseases 0.000 abstract description 5
- YLDDSILEQGVNSB-UHFFFAOYSA-N 6-chlorospiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(Cl)=CC=C2OCCC21NC(=O)NC2=O YLDDSILEQGVNSB-UHFFFAOYSA-N 0.000 abstract description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 abstract description 2
- WZCXMBLDKALJTK-UHFFFAOYSA-N 2,2-dioxo-1h-isothiochromen-4-one Chemical compound C1=CC=C2C(=O)CS(=O)(=O)CC2=C1 WZCXMBLDKALJTK-UHFFFAOYSA-N 0.000 abstract description 2
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- CDALGRHRPPTQPM-UHFFFAOYSA-N spiro[1,2-dihydroindene-3,5'-imidazolidine]-2',4'-dione Chemical compound N1C(=O)NC(=O)C11C2=CC=CC=C2CC1 CDALGRHRPPTQPM-UHFFFAOYSA-N 0.000 abstract description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 abstract 2
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- 239000012467 final product Substances 0.000 description 22
- 239000007858 starting material Substances 0.000 description 22
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- UJGDLLGKMWVCPT-UHFFFAOYSA-N 6-methoxy-2,3-dihydroinden-1-one Chemical compound COC1=CC=C2CCC(=O)C2=C1 UJGDLLGKMWVCPT-UHFFFAOYSA-N 0.000 description 14
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- C—CHEMISTRY; METALLURGY
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73306276A | 1976-10-18 | 1976-10-18 | |
| US733,062 | 1976-10-18 | ||
| US05/767,803 US4117230A (en) | 1976-10-18 | 1977-02-11 | Hydantoin derivatives as therapeutic agents |
| US767,803 | 1977-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088945A true CA1088945A (en) | 1980-11-04 |
Family
ID=27112515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA287,868A Expired CA1088945A (en) | 1976-10-18 | 1977-09-30 | Hydantoin derivatives as therapeutic agents |
Country Status (29)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130714A (en) * | 1977-05-23 | 1978-12-19 | Pfizer Inc. | Hydantoin therapeutic agents |
| US4127665A (en) * | 1978-01-18 | 1978-11-28 | Pfizer Inc. | Thienohydantoin derivatives |
| US4147797A (en) * | 1978-08-11 | 1979-04-03 | Pfizer Inc. | Spiro-furanohydantoin derivatives |
| US4200642A (en) * | 1978-08-21 | 1980-04-29 | Pfizer Inc. | Spiro-oxazolidindiones |
| US4181728A (en) * | 1978-11-16 | 1980-01-01 | Pfizer Inc. | Spiro-polycyclicimidazolidinedione derivatives |
| US4181729A (en) * | 1979-03-21 | 1980-01-01 | Pfizer Inc. | Phenyl or phenoxy substituted spiro-imidazolidinedione derivatives |
| US4235911A (en) * | 1979-06-13 | 1980-11-25 | Pfizer Inc. | Hydantoin derivatives |
| US4283409A (en) * | 1979-10-29 | 1981-08-11 | Pfizer Inc. | Imidazolone derivatives |
| US4286098A (en) * | 1980-03-28 | 1981-08-25 | Pfizer Inc. | Process for the preparation of chiral hydantoins |
| JPS5745185A (en) * | 1980-07-21 | 1982-03-13 | Eisai Co Ltd | Hydantoin derivative and its preparation |
| ATE11781T1 (de) * | 1981-05-13 | 1985-02-15 | Imperial Chemical Industries Plc | Pharmazeutische zubereitungen, die spirosuccinimidderivate enthalten. |
| JPS58213717A (ja) * | 1982-01-20 | 1983-12-12 | Eisai Co Ltd | ヒダントイン誘導体を含有する治療用薬剤 |
| JPS59500617A (ja) * | 1982-04-15 | 1984-04-12 | アルコン・ラボラトリ−ズ・インコ−ポレ−テッド | ヒダントイン治療剤 |
| ZA839023B (en) * | 1982-12-06 | 1985-07-31 | Pfizer | Spiro-3-hetero-azolones for treatment of diabetic complications |
| US4474967A (en) * | 1983-04-27 | 1984-10-02 | Pfizer Inc. | 8-Deutero and 8-tritio-substituted derivatives of D-4S-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione |
| WO1986002647A1 (en) * | 1984-10-30 | 1986-05-09 | Pfizer Inc. | Spiro-heteroazolones for treatment of diabetes complications |
| JPS61200991A (ja) * | 1985-03-04 | 1986-09-05 | Sanwa Kagaku Kenkyusho:Kk | スピロ―３―ヘテロアゾリジン化合物、その製法及びそれを有効成分とする糖尿病合併症の予防及び治療剤 |
| US4575507A (en) * | 1985-05-29 | 1986-03-11 | Pfizer Inc. | Spiro-imidazolidines as aldose reductase inhibitors and their pharmaceutical use |
| JPS6357588A (ja) * | 1986-08-28 | 1988-03-12 | Sanwa Kagaku Kenkyusho Co Ltd | ヒダントイン誘導体、その塩並びに該化合物を有効成分とする糖尿病合併症の予防及び治療剤 |
| WO1989001775A1 (en) * | 1987-09-04 | 1989-03-09 | Pfizer Inc. | Azolidinedione derivatives |
| GB2355264A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Spirohydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
| US7439383B2 (en) | 2002-04-18 | 2008-10-21 | University Of Virginia Patent Foundation | Sodium channel blockers |
| FR2955107B1 (fr) | 2010-01-08 | 2012-03-02 | Servier Lab | Nouveaux derives thiochromanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB818724A (en) * | 1956-10-18 | 1959-08-19 | Ici Ltd | Hydantoin derivatives |
| DE1135915B (de) * | 1961-06-29 | 1962-09-06 | Asta Werke Ag Chem Fab | Verfahren zur Herstellung neuer, antikonvulsiv wirksamer Spirohydantoine |
| US3532744A (en) * | 1967-07-28 | 1970-10-06 | American Home Prod | 1- and 2-amino substituted indane and tetralene carboxylic acids |
| US3821383A (en) * | 1972-07-10 | 1974-06-28 | Ayerst Mckenna & Harrison | Compositions for and a method of treating diabetic complications |
| DE2449030A1 (de) * | 1974-10-11 | 1976-05-20 | Schering Ag | Neue pyridin-derivate |
| US4130714A (en) * | 1977-05-23 | 1978-12-19 | Pfizer Inc. | Hydantoin therapeutic agents |
-
1977
- 1977-09-30 CA CA287,868A patent/CA1088945A/en not_active Expired
- 1977-10-03 SE SE7711053A patent/SE437024B/sv not_active IP Right Cessation
- 1977-10-04 GR GR54503A patent/GR70201B/el unknown
- 1977-10-05 NZ NZ185358A patent/NZ185358A/xx unknown
- 1977-10-06 AU AU29431/77A patent/AU504978B2/en not_active Expired
- 1977-10-10 YU YU2442/77A patent/YU40821B/xx unknown
- 1977-10-10 IL IL53094A patent/IL53094A0/xx not_active IP Right Cessation
- 1977-10-14 DE DE2759543A patent/DE2759543C2/de not_active Expired
- 1977-10-14 DE DE2759927A patent/DE2759927C2/de not_active Expired
- 1977-10-14 FI FI773060A patent/FI62307C/fi not_active IP Right Cessation
- 1977-10-14 PH PH20335A patent/PH15639A/en unknown
- 1977-10-14 DE DE2746244A patent/DE2746244C2/de not_active Expired
- 1977-10-14 DE DE2759542A patent/DE2759542C2/de not_active Expired
- 1977-10-15 ES ES463267A patent/ES463267A1/es not_active Expired
- 1977-10-17 PT PT67164A patent/PT67164B/pt unknown
- 1977-10-17 NL NL7711358.A patent/NL167434C/xx not_active IP Right Cessation
- 1977-10-17 NO NO773548A patent/NO148453C/no unknown
- 1977-10-17 CH CH1262677A patent/CH625511A5/fr not_active IP Right Cessation
- 1977-10-17 LU LU78330A patent/LU78330A1/xx unknown
- 1977-10-17 JP JP12437177A patent/JPS5353653A/ja active Granted
- 1977-10-17 MX MX776490U patent/MX4899E/es unknown
- 1977-10-17 IE IE2114/77A patent/IE45805B1/en not_active IP Right Cessation
- 1977-10-17 FR FR7731216A patent/FR2367754A1/fr active Granted
- 1977-10-17 DK DK461377A patent/DK150302C/da not_active IP Right Cessation
- 1977-10-17 GB GB43122/77A patent/GB1566171A/en not_active Expired
- 1977-10-18 AR AR269623A patent/AR220901A1/es active
- 1977-10-18 BG BG037604A patent/BG28847A3/xx unknown
- 1977-10-18 AT AT745977A patent/AT356136B/de not_active IP Right Cessation
- 1977-10-18 DD DD7700201582A patent/DD131931A5/xx unknown
-
1978
- 1978-11-25 JP JP53145926A patent/JPS607997B2/ja not_active Expired
- 1978-11-25 JP JP53145925A patent/JPS5940388B2/ja not_active Expired
-
1981
- 1981-10-09 KE KE3167A patent/KE3167A/xx unknown
- 1981-11-05 HK HK538/81A patent/HK53881A/xx unknown
-
1982
- 1982-12-30 MY MY157/82A patent/MY8200157A/xx unknown
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