SE459734B - Fluorenderivat, saett att framstaella dessa och antiinflammatoriska, analgetiska och/eller antipyretiska laekemedel - Google Patents
Fluorenderivat, saett att framstaella dessa och antiinflammatoriska, analgetiska och/eller antipyretiska laekemedelInfo
- Publication number
- SE459734B SE459734B SE8405592A SE8405592A SE459734B SE 459734 B SE459734 B SE 459734B SE 8405592 A SE8405592 A SE 8405592A SE 8405592 A SE8405592 A SE 8405592A SE 459734 B SE459734 B SE 459734B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- carbon atoms
- hydrogen
- alkyl group
- fluorenyl
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 3
- 239000002221 antipyretic Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title description 7
- 230000000202 analgesic effect Effects 0.000 title description 3
- 230000001754 anti-pyretic effect Effects 0.000 title description 3
- 239000003814 drug Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 60
- -1 nitro- Chemical class 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 35
- 239000013078 crystal Substances 0.000 description 25
- 238000000921 elemental analysis Methods 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
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- 241000700159 Rattus Species 0.000 description 9
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- PBPURXLOZIAVSH-UHFFFAOYSA-N 4-(7-methoxy-9h-fluoren-2-yl)butan-2-one Chemical compound CC(=O)CCC1=CC=C2C3=CC=C(OC)C=C3CC2=C1 PBPURXLOZIAVSH-UHFFFAOYSA-N 0.000 description 3
- CALKFAUQDXTFBF-UHFFFAOYSA-N 4-(9h-fluoren-2-yl)but-3-en-2-one Chemical compound C1=CC=C2C3=CC=C(C=CC(=O)C)C=C3CC2=C1 CALKFAUQDXTFBF-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical group CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 3
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/38—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the fluorene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- 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
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/225—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/237—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/252—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58211373A JPS60104027A (ja) | 1983-11-09 | 1983-11-09 | フルオレン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8405592D0 SE8405592D0 (sv) | 1984-11-08 |
| SE8405592L SE8405592L (sv) | 1985-05-10 |
| SE459734B true SE459734B (sv) | 1989-07-31 |
Family
ID=16604883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8405592A SE459734B (sv) | 1983-11-09 | 1984-11-08 | Fluorenderivat, saett att framstaella dessa och antiinflammatoriska, analgetiska och/eller antipyretiska laekemedel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4581377A (fr) |
| JP (1) | JPS60104027A (fr) |
| KR (1) | KR850004086A (fr) |
| AU (1) | AU574110B2 (fr) |
| BE (1) | BE900997A (fr) |
| CA (1) | CA1234836A (fr) |
| CH (1) | CH662345A5 (fr) |
| DE (1) | DE3440503A1 (fr) |
| ES (1) | ES8607894A1 (fr) |
| FR (1) | FR2554441B1 (fr) |
| GB (1) | GB2157680B (fr) |
| IT (1) | IT1178218B (fr) |
| NL (1) | NL8403276A (fr) |
| SE (1) | SE459734B (fr) |
| ZA (1) | ZA848357B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2142735A1 (fr) * | 1993-06-18 | 1995-01-05 | Tatsuyoshi Tanaka | Derives du fluorenone, procede de preparation correspondant et agent de traitement ou de prevention de la degeneration du systeme nerveux central ou du systeme nerveux peripherique |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB760986A (en) * | 1953-06-06 | 1956-11-07 | Ruetgerswerke Ag | Aromatic condensation products |
| US3903145A (en) * | 1971-06-18 | 1975-09-02 | Squibb & Sons Inc | 9-Substituted fluorene-2-acetic acid derivatives |
| US4011266A (en) * | 1973-10-31 | 1977-03-08 | Xerox Corporation | 2-vinyl-fluorenone and derivatives thereof |
| GB1479297A (en) * | 1974-07-04 | 1977-07-13 | Beecham Group Ltd | 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them |
| US3975540A (en) * | 1975-04-28 | 1976-08-17 | Syntex (U.S.A.) Inc. | 2-Substituted-5-oxo-5H-dibenzo(a,d)cycloheptenes, and derivatives thereof, and methods and compositions for the use thereof |
| DE3439484A1 (de) * | 1984-10-27 | 1986-05-07 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von 9,9-bis-(4-hydroxyphenyl)-fluoren |
-
1983
- 1983-11-09 JP JP58211373A patent/JPS60104027A/ja active Granted
-
1984
- 1984-10-18 GB GB08426337A patent/GB2157680B/en not_active Expired
- 1984-10-25 ZA ZA848357A patent/ZA848357B/xx unknown
- 1984-10-29 NL NL8403276A patent/NL8403276A/xx not_active Application Discontinuation
- 1984-11-06 DE DE19843440503 patent/DE3440503A1/de not_active Withdrawn
- 1984-11-06 FR FR8416862A patent/FR2554441B1/fr not_active Expired
- 1984-11-06 CH CH5316/84A patent/CH662345A5/fr not_active IP Right Cessation
- 1984-11-06 ES ES537402A patent/ES8607894A1/es not_active Expired
- 1984-11-07 BE BE0/213963A patent/BE900997A/fr not_active IP Right Cessation
- 1984-11-07 US US06/669,455 patent/US4581377A/en not_active Expired - Fee Related
- 1984-11-07 AU AU35192/84A patent/AU574110B2/en not_active Ceased
- 1984-11-08 IT IT49140/84A patent/IT1178218B/it active
- 1984-11-08 SE SE8405592A patent/SE459734B/sv not_active IP Right Cessation
- 1984-11-08 CA CA000467398A patent/CA1234836A/fr not_active Expired
- 1984-11-08 KR KR1019840006991A patent/KR850004086A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2554441A1 (fr) | 1985-05-10 |
| AU574110B2 (en) | 1988-06-30 |
| GB2157680B (en) | 1988-03-16 |
| SE8405592L (sv) | 1985-05-10 |
| GB2157680A (en) | 1985-10-30 |
| GB8426337D0 (en) | 1984-11-21 |
| ZA848357B (en) | 1985-06-26 |
| IT8449140A1 (it) | 1986-05-08 |
| US4581377A (en) | 1986-04-08 |
| IT1178218B (it) | 1987-09-09 |
| JPS60104027A (ja) | 1985-06-08 |
| ES8607894A1 (es) | 1986-06-01 |
| SE8405592D0 (sv) | 1984-11-08 |
| CA1234836A (fr) | 1988-04-05 |
| ES537402A0 (es) | 1986-06-01 |
| FR2554441B1 (fr) | 1989-01-06 |
| IT8449140A0 (it) | 1984-11-08 |
| DE3440503A1 (de) | 1985-06-05 |
| JPH0460095B2 (fr) | 1992-09-25 |
| CH662345A5 (fr) | 1987-09-30 |
| AU3519284A (en) | 1985-05-16 |
| BE900997A (fr) | 1985-05-07 |
| KR850004086A (ko) | 1985-07-01 |
| NL8403276A (nl) | 1985-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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