NL8304340A - Carboxamidoderivaten van 5h-1,3,4-thiadiazolo 3,2-apyrimidenen en werkwijze ter bereiding daarvan. - Google Patents
Carboxamidoderivaten van 5h-1,3,4-thiadiazolo 3,2-apyrimidenen en werkwijze ter bereiding daarvan. Download PDFInfo
- Publication number
- NL8304340A NL8304340A NL8304340A NL8304340A NL8304340A NL 8304340 A NL8304340 A NL 8304340A NL 8304340 A NL8304340 A NL 8304340A NL 8304340 A NL8304340 A NL 8304340A NL 8304340 A NL8304340 A NL 8304340A
- Authority
- NL
- Netherlands
- Prior art keywords
- pyridyl
- thiadiazolo
- carboxamide
- oxo
- pyrimidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- -1 N-pyrrolidinyl ring Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- LYASTVLDAJIXBL-UHFFFAOYSA-N 1,3-benzothiazole-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=NC2=C1 LYASTVLDAJIXBL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- QRZZCGXTNFQXFF-UHFFFAOYSA-N 4-methyl-1,3-thiazole-2-carboxamide Chemical compound CC1=CSC(C(N)=O)=N1 QRZZCGXTNFQXFF-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
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- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 235000011007 phosphoric acid Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- HRWSRGPWDJADIS-UHFFFAOYSA-N 4,6-dimethylpyridine-2-carboxamide Chemical compound CC1=CC(C)=NC(C(N)=O)=C1 HRWSRGPWDJADIS-UHFFFAOYSA-N 0.000 description 5
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- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- PWVGMQFTWJTCNG-UHFFFAOYSA-N thiadiazolo[5,4-d]pyrimidine Chemical class C1=NC=C2N=NSC2=N1 PWVGMQFTWJTCNG-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8236642 | 1982-12-23 | ||
| GB8236642 | 1982-12-23 | ||
| GB838329746A GB8329746D0 (en) | 1983-11-08 | 1983-11-08 | Carboxamido-derivatives |
| GB8329746 | 1983-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8304340A true NL8304340A (nl) | 1984-07-16 |
Family
ID=26284768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8304340A NL8304340A (nl) | 1982-12-23 | 1983-12-16 | Carboxamidoderivaten van 5h-1,3,4-thiadiazolo 3,2-apyrimidenen en werkwijze ter bereiding daarvan. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4522944A (enExample) |
| AT (1) | AT385036B (enExample) |
| AU (1) | AU558600B2 (enExample) |
| CA (1) | CA1211440A (enExample) |
| CH (1) | CH657136A5 (enExample) |
| DE (1) | DE3346223A1 (enExample) |
| DK (1) | DK593983A (enExample) |
| FI (1) | FI834698A7 (enExample) |
| FR (1) | FR2538392B1 (enExample) |
| GR (1) | GR79479B (enExample) |
| IL (1) | IL70522A (enExample) |
| IT (1) | IT1194521B (enExample) |
| NL (1) | NL8304340A (enExample) |
| SE (1) | SE454698B (enExample) |
| SU (1) | SU1297731A3 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3702758A1 (de) * | 1987-01-30 | 1988-09-29 | Hoechst Ag | Substituierte 3-phenyl-7h-thiazolo (3,2-b) (1,2,4) triazin-7-one, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung, sowie einige bei der herstellung der genannten verbindungen gebildete zwischenprodukte |
| CN101796051B (zh) * | 2007-03-12 | 2013-11-06 | 细胞内治疗公司 | 与取代的杂环稠合的γ-咔啉的合成 |
| EP2836211B1 (en) | 2012-04-14 | 2019-03-20 | Intra-Cellular Therapies, Inc. | Treatment of PTSD and impulse control disorders |
| PT2968320T (pt) | 2013-03-15 | 2021-01-28 | Intra Cellular Therapies Inc | Compostos orgânicos |
| IL321987A (en) | 2013-12-03 | 2025-09-01 | Intra Cellular Therapies Inc | A long-acting injectable preparation containing polymeric microspheres of modified compressed gamma-carboline heterocyclic compounds or a sustained-release pharmaceutical preparation containing these compounds for use in the treatment of bipolar I and/or bipolar II disorders |
| WO2015154025A1 (en) | 2014-04-04 | 2015-10-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| CN106456638A (zh) | 2014-04-04 | 2017-02-22 | 细胞内治疗公司 | 有机化合物 |
| CA3011983A1 (en) | 2016-01-26 | 2017-08-03 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| JP6997718B2 (ja) | 2016-03-28 | 2022-01-18 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規共結晶 |
| JP2019513143A (ja) | 2016-03-28 | 2019-05-23 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規塩類および結晶 |
| US11331316B2 (en) | 2016-10-12 | 2022-05-17 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
| WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2018126143A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2018175969A1 (en) | 2017-03-24 | 2018-09-27 | Intra-Cellular Therapies, Inc. | Novel compositions and methods |
| IL272252B2 (en) | 2017-07-26 | 2024-03-01 | Intra Cellular Therapies Inc | Derivatives of substituted heterocycle fused gamma-carbolines, pharmaceutical compositions comnprising them and their use in treatment |
| KR102899502B1 (ko) | 2017-07-26 | 2025-12-11 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| MX2020009928A (es) | 2018-03-23 | 2021-01-08 | Intra Cellular Therapies Inc | Compuestos organicos. |
| EP3628007B1 (en) | 2018-06-06 | 2023-05-03 | Intra-Cellular Therapies, Inc. | Novel salts and crystals |
| WO2019237037A1 (en) | 2018-06-08 | 2019-12-12 | Intra-Cellular Therapies, Inc. | Novel methods |
| EP3609891B1 (en) | 2018-06-11 | 2026-02-11 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
| WO2020047241A1 (en) | 2018-08-29 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel compositions and methods |
| KR20210052472A (ko) | 2018-08-31 | 2021-05-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 신규한 방법 |
| WO2020047407A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| BR112022000231A2 (pt) | 2019-07-07 | 2022-02-22 | Intra Cellular Therapies Inc | Novos métodos |
| JP7261942B2 (ja) | 2019-12-11 | 2023-04-20 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129981B2 (enExample) * | 1973-07-17 | 1976-08-28 | ||
| GB1568962A (en) * | 1975-10-31 | 1980-06-11 | Beecham Group Ltd | Reparation and compositions containing them (heterocyclic-carbonylamino)pencillins methods for their p |
| JPS55115889A (en) * | 1979-02-28 | 1980-09-06 | Teijin Ltd | 6-carbamoylthiazolo 3,2-a pyrimidine derivative and its preparation |
| JPS57142989A (en) * | 1981-02-27 | 1982-09-03 | Dai Ichi Seiyaku Co Ltd | Thiazolopyrimidine derivative |
-
1983
- 1983-12-08 US US06/559,322 patent/US4522944A/en not_active Expired - Fee Related
- 1983-12-15 GR GR73259A patent/GR79479B/el unknown
- 1983-12-15 AT AT0438383A patent/AT385036B/de not_active IP Right Cessation
- 1983-12-16 NL NL8304340A patent/NL8304340A/nl not_active Application Discontinuation
- 1983-12-16 IT IT24207/83A patent/IT1194521B/it active
- 1983-12-19 AU AU22525/83A patent/AU558600B2/en not_active Ceased
- 1983-12-20 CH CH6783/83A patent/CH657136A5/de not_active IP Right Cessation
- 1983-12-20 FI FI834698A patent/FI834698A7/fi not_active Application Discontinuation
- 1983-12-21 DE DE19833346223 patent/DE3346223A1/de not_active Withdrawn
- 1983-12-22 SE SE8307133A patent/SE454698B/sv not_active IP Right Cessation
- 1983-12-22 DK DK593983A patent/DK593983A/da not_active Application Discontinuation
- 1983-12-22 CA CA000444151A patent/CA1211440A/en not_active Expired
- 1983-12-22 SU SU833682101A patent/SU1297731A3/ru active
- 1983-12-22 IL IL70522A patent/IL70522A/xx not_active IP Right Cessation
- 1983-12-23 FR FR8320704A patent/FR2538392B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT8324207A0 (it) | 1983-12-16 |
| IL70522A (en) | 1986-02-28 |
| ATA438383A (de) | 1987-07-15 |
| CA1211440A (en) | 1986-09-16 |
| AU2252583A (en) | 1984-06-28 |
| FI834698A7 (fi) | 1984-06-24 |
| FR2538392B1 (fr) | 1987-01-16 |
| SE8307133L (sv) | 1984-06-24 |
| AU558600B2 (en) | 1987-02-05 |
| SE454698B (sv) | 1988-05-24 |
| CH657136A5 (de) | 1986-08-15 |
| GR79479B (enExample) | 1984-10-30 |
| FR2538392A1 (fr) | 1984-06-29 |
| US4522944A (en) | 1985-06-11 |
| SE8307133D0 (sv) | 1983-12-22 |
| AT385036B (de) | 1988-02-10 |
| SU1297731A3 (ru) | 1987-03-15 |
| DK593983A (da) | 1984-06-24 |
| IT1194521B (it) | 1988-09-22 |
| DE3346223A1 (de) | 1984-06-28 |
| IL70522A0 (en) | 1984-03-30 |
| FI834698A0 (fi) | 1983-12-20 |
| DK593983D0 (da) | 1983-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BV | The patent application has lapsed |