GB1584298A - Indane carboxylic acid derivatives - Google Patents
Indane carboxylic acid derivatives Download PDFInfo
- Publication number
- GB1584298A GB1584298A GB51699/77A GB5169977A GB1584298A GB 1584298 A GB1584298 A GB 1584298A GB 51699/77 A GB51699/77 A GB 51699/77A GB 5169977 A GB5169977 A GB 5169977A GB 1584298 A GB1584298 A GB 1584298A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indane
- carboxylic acid
- group
- phenyl
- acetamido
- 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
- JBQMFBWTKWOSQX-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)CCC2=C1 JBQMFBWTKWOSQX-UHFFFAOYSA-N 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- -1 amino ester Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- STZNWHRZVBVEHD-UHFFFAOYSA-N 5-(4-methylsulfonylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 STZNWHRZVBVEHD-UHFFFAOYSA-N 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 claims description 2
- SGBJNYFXPDFXNU-UHFFFAOYSA-N 5-(4-acetamidobenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 SGBJNYFXPDFXNU-UHFFFAOYSA-N 0.000 claims description 2
- GCGOVHRPHZEYDO-UHFFFAOYSA-N 5-[4-(dimethylsulfamoyl)benzoyl]-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 GCGOVHRPHZEYDO-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229940100445 wheat starch Drugs 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000002744 anti-aggregatory effect Effects 0.000 abstract 1
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000004291 sulphur dioxide Substances 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 101100533387 Homo sapiens SCGB1D1 gene Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 102100028659 Secretoglobin family 1D member 1 Human genes 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- KUSFRNJBKHKRMW-UHFFFAOYSA-N methyl 5-(4-chlorosulfonylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 KUSFRNJBKHKRMW-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7637574A FR2374032A2 (fr) | 1976-12-14 | 1976-12-14 | Nouveaux acides carboxyliques derives de l'indane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1584298A true GB1584298A (en) | 1981-02-11 |
Family
ID=9181028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB51699/77A Expired GB1584298A (en) | 1976-12-14 | 1977-12-12 | Indane carboxylic acid derivatives |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5373548A (sv) |
| AT (1) | AT355559B (sv) |
| AU (1) | AU515268B2 (sv) |
| BE (1) | BE861826R (sv) |
| CA (1) | CA1088554A (sv) |
| CH (1) | CH627728A5 (sv) |
| DD (1) | DD133323A6 (sv) |
| DE (1) | DE2753315A1 (sv) |
| DK (1) | DK144640C (sv) |
| ES (1) | ES465056A2 (sv) |
| FR (1) | FR2374032A2 (sv) |
| GB (1) | GB1584298A (sv) |
| HU (1) | HU177226B (sv) |
| IE (1) | IE46013B1 (sv) |
| IL (2) | IL60598A0 (sv) |
| MX (1) | MX4954E (sv) |
| NL (1) | NL7713876A (sv) |
| NO (1) | NO774285L (sv) |
| SE (1) | SE436740B (sv) |
| SU (1) | SU799646A3 (sv) |
| ZA (1) | ZA777438B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2526124T3 (es) * | 2010-06-16 | 2015-01-07 | Cymabay Therapeutics, Inc. | Agonistas del receptor GPR120 y sus usos |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4980053A (sv) * | 1972-12-05 | 1974-08-02 | ||
| JPS5838416B2 (ja) * | 1974-05-31 | 1983-08-23 | 武田薬品工業株式会社 | カンジヨウカゴウブツノセイゾウホウ |
| JPS5335944B2 (sv) * | 1974-05-21 | 1978-09-29 |
-
1976
- 1976-12-14 FR FR7637574A patent/FR2374032A2/fr active Granted
-
1977
- 1977-11-30 DE DE19772753315 patent/DE2753315A1/de not_active Ceased
- 1977-12-12 GB GB51699/77A patent/GB1584298A/en not_active Expired
- 1977-12-13 DK DK554677A patent/DK144640C/da not_active IP Right Cessation
- 1977-12-13 NO NO774285A patent/NO774285L/no unknown
- 1977-12-13 IE IE2520/77A patent/IE46013B1/en unknown
- 1977-12-13 MX MX776686U patent/MX4954E/es unknown
- 1977-12-13 HU HU77LI316A patent/HU177226B/hu unknown
- 1977-12-13 SE SE7714110A patent/SE436740B/sv unknown
- 1977-12-13 DD DD7700202588A patent/DD133323A6/xx unknown
- 1977-12-14 CH CH1541077A patent/CH627728A5/fr not_active IP Right Cessation
- 1977-12-14 AT AT892577A patent/AT355559B/de not_active IP Right Cessation
- 1977-12-14 CA CA293,076A patent/CA1088554A/fr not_active Expired
- 1977-12-14 JP JP14943377A patent/JPS5373548A/ja active Pending
- 1977-12-14 NL NL7713876A patent/NL7713876A/xx not_active Application Discontinuation
- 1977-12-14 BE BE183429A patent/BE861826R/xx not_active IP Right Cessation
- 1977-12-14 ES ES465056A patent/ES465056A2/es not_active Expired
- 1977-12-14 ZA ZA00777438A patent/ZA777438B/xx unknown
- 1977-12-14 AU AU31530/77A patent/AU515268B2/en not_active Expired
-
1979
- 1979-04-06 SU SU792746906A patent/SU799646A3/ru active
-
1980
- 1980-07-15 IL IL60598A patent/IL60598A0/xx unknown
- 1980-07-15 IL IL60599A patent/IL60599A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2753315A1 (de) | 1978-06-15 |
| IL60598A0 (en) | 1980-09-16 |
| CH627728A5 (en) | 1982-01-29 |
| AT355559B (de) | 1980-03-10 |
| SE7714110L (sv) | 1978-06-15 |
| ES465056A2 (es) | 1979-01-16 |
| FR2374032A2 (fr) | 1978-07-13 |
| SE436740B (sv) | 1985-01-21 |
| IL60599A0 (en) | 1980-09-16 |
| ZA777438B (en) | 1979-05-30 |
| JPS5373548A (en) | 1978-06-30 |
| ATA892577A (de) | 1979-08-15 |
| NO774285L (no) | 1978-06-15 |
| SU799646A3 (ru) | 1981-01-23 |
| AU515268B2 (en) | 1981-03-26 |
| MX4954E (es) | 1983-01-13 |
| BE861826R (fr) | 1978-06-14 |
| AU3153077A (en) | 1979-06-21 |
| DD133323A6 (de) | 1978-12-27 |
| IE46013L (en) | 1978-06-14 |
| DK144640C (da) | 1982-10-04 |
| HU177226B (en) | 1981-08-28 |
| IE46013B1 (en) | 1983-01-26 |
| NL7713876A (nl) | 1978-06-16 |
| DK144640B (da) | 1982-04-26 |
| CA1088554A (fr) | 1980-10-28 |
| DK554677A (da) | 1978-06-15 |
| FR2374032B2 (sv) | 1979-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |