JPS60116685A - １，３―ジヒドロ―６―メチル―フロー（３，４―ｃ）―ピリジン誘導体、その製造方法およびこれを含有する抗ヒスタミン剤組成物 - Google Patents
１，３―ジヒドロ―６―メチル―フロー（３，４―ｃ）―ピリジン誘導体、その製造方法およびこれを含有する抗ヒスタミン剤組成物Info
- Publication number
- JPS60116685A JPS60116685A JP59240900A JP24090084A JPS60116685A JP S60116685 A JPS60116685 A JP S60116685A JP 59240900 A JP59240900 A JP 59240900A JP 24090084 A JP24090084 A JP 24090084A JP S60116685 A JPS60116685 A JP S60116685A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- groups
- methyl
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 title description 5
- IHWMIFMVQLOHLG-UHFFFAOYSA-N 6-methyl-1,3-dihydrofuro[3,4-c]pyridine Chemical class C1=NC(C)=CC2=C1COC2 IHWMIFMVQLOHLG-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical class N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- -1 N-pyrrolidinyl groups Chemical group 0.000 claims description 3
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 238000000921 elemental analysis Methods 0.000 description 18
- 239000002994 raw material Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- ICWXMOFJDWRMFA-UHFFFAOYSA-N 1-methylfuro[3,4-c]pyridin-7-ol Chemical compound CC=1OC=C2C=NC=C(C21)O ICWXMOFJDWRMFA-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- VNNXQKIUVGKNHW-UHFFFAOYSA-N 2-furo[3,4-c]pyridin-7-yloxyacetic acid Chemical class OC(=O)COC1=CN=CC2=COC=C12 VNNXQKIUVGKNHW-UHFFFAOYSA-N 0.000 description 1
- YYSDEJFOFNQOAW-UHFFFAOYSA-N 4-chloro-3-(4-methoxyphenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound COC1=CC=C(C=C1)C1OCC2=C1C(=NC(=C2O)C)Cl YYSDEJFOFNQOAW-UHFFFAOYSA-N 0.000 description 1
- NZOCLVWZHBNOKT-UHFFFAOYSA-N 6-methylfuro[3,4-c]pyridin-7-ol Chemical compound OC1=C(C)N=CC2=COC=C21 NZOCLVWZHBNOKT-UHFFFAOYSA-N 0.000 description 1
- RBMJDWDBTDQYHU-UHFFFAOYSA-N 6-methylfuro[3,4-c]pyridine Chemical class CC1=CC=2C(C=N1)=COC=2 RBMJDWDBTDQYHU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960005042 mequitazine Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8330658 | 1983-11-17 | ||
| GB838330658A GB8330658D0 (en) | 1983-11-17 | 1983-11-17 | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116685A true JPS60116685A (ja) | 1985-06-24 |
| JPH0313235B2 JPH0313235B2 (en, 2012) | 1991-02-22 |
Family
ID=10551897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59240900A Granted JPS60116685A (ja) | 1983-11-17 | 1984-11-16 | １，３―ジヒドロ―６―メチル―フロー（３，４―ｃ）―ピリジン誘導体、その製造方法およびこれを含有する抗ヒスタミン剤組成物 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4569938A (en, 2012) |
| JP (1) | JPS60116685A (en, 2012) |
| AT (1) | AT391868B (en, 2012) |
| BE (1) | BE900941A (en, 2012) |
| CA (1) | CA1257272A (en, 2012) |
| CH (1) | CH660737A5 (en, 2012) |
| DE (1) | DE3441975A1 (en, 2012) |
| DK (1) | DK157932C (en, 2012) |
| DZ (1) | DZ702A1 (en, 2012) |
| ES (1) | ES537666A0 (en, 2012) |
| FI (1) | FI80701C (en, 2012) |
| FR (2) | FR2555181B1 (en, 2012) |
| GB (2) | GB8330658D0 (en, 2012) |
| HK (1) | HK77987A (en, 2012) |
| IE (1) | IE58097B1 (en, 2012) |
| IT (1) | IT1177185B (en, 2012) |
| LU (1) | LU85634A1 (en, 2012) |
| MA (1) | MA20263A1 (en, 2012) |
| MY (1) | MY100665A (en, 2012) |
| NL (1) | NL8403318A (en, 2012) |
| OA (1) | OA07865A (en, 2012) |
| SE (1) | SE458277B (en, 2012) |
| SG (1) | SG52687G (en, 2012) |
| ZA (1) | ZA848128B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| PT1169322E (pt) * | 1999-03-08 | 2007-04-30 | Medicure Inc | Análogos de piridoxal para o tratamento de desordens causadas por uma deficiência em vitamina b-6. |
| WO2001003682A2 (en) | 1999-07-13 | 2001-01-18 | Medicure Inc. | Use of pyridoxin derivatives for the treatment of diabetes and related complications |
| JP2003507418A (ja) * | 1999-08-24 | 2003-02-25 | メディキュア インターナショナル インコーポレイテッド | 心血管疾患とその関連疾患の治療 |
| EP1268498B1 (en) | 2000-02-29 | 2005-04-13 | Medicure International Inc. | Cardioprotective phosphonates |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US6586414B2 (en) | 2000-03-28 | 2003-07-01 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| DE60128912T9 (de) | 2000-07-07 | 2008-06-26 | Medicure International Inc. | Pyridoxin- und pyridoxalanaloga als cardiovasculäre therapeutika |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US20040121988A1 (en) * | 2001-03-28 | 2004-06-24 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US20040186077A1 (en) * | 2003-03-17 | 2004-09-23 | Medicure International Inc. | Novel heteroaryl phosphonates as cardioprotective agents |
| EP1773370A1 (en) * | 2004-07-07 | 2007-04-18 | Medicure International Inc. | Combination therapies employing platelet aggregation drugs |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| AU2005304220A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US20070105817A1 (en) * | 2005-11-09 | 2007-05-10 | Jim Page | Use of cicletanine and other furopyridines for treatment of systolic-predominant hypertension, isolated systolic hypertension, elevated pulse pressure, and general hypertension |
| US20070149485A1 (en) * | 2005-11-28 | 2007-06-28 | Medicure International, Inc. | Selected dosage for the treatment of cardiovascular and related pathologies |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT297442B (de) * | 1970-04-01 | 1972-03-27 | Unilever Nv | Verfahren zum Reinigen, Entfetten, Entzundern und Beizen von Metallen |
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| IN156817B (en, 2012) * | 1981-02-10 | 1985-11-09 | Scras |
-
1983
- 1983-11-17 GB GB838330658A patent/GB8330658D0/en active Pending
-
1984
- 1984-10-17 ZA ZA848128A patent/ZA848128B/xx unknown
- 1984-10-19 GB GB08426489A patent/GB2149781B/en not_active Expired
- 1984-10-26 CH CH5127/84A patent/CH660737A5/fr not_active IP Right Cessation
- 1984-10-30 BE BE0/213925A patent/BE900941A/fr not_active IP Right Cessation
- 1984-11-01 NL NL8403318A patent/NL8403318A/nl not_active Application Discontinuation
- 1984-11-05 US US06/668,394 patent/US4569938A/en not_active Expired - Lifetime
- 1984-11-07 LU LU85634A patent/LU85634A1/fr unknown
- 1984-11-08 FI FI844383A patent/FI80701C/fi not_active IP Right Cessation
- 1984-11-08 MA MA20487A patent/MA20263A1/fr unknown
- 1984-11-14 IT IT23564/84A patent/IT1177185B/it active
- 1984-11-14 CA CA000467829A patent/CA1257272A/en not_active Expired
- 1984-11-14 DZ DZ847329A patent/DZ702A1/fr active
- 1984-11-15 ES ES537666A patent/ES537666A0/es active Granted
- 1984-11-16 DK DK545684A patent/DK157932C/da not_active IP Right Cessation
- 1984-11-16 FR FR8417478A patent/FR2555181B1/fr not_active Expired
- 1984-11-16 FR FR8417479A patent/FR2555049B1/fr not_active Expired
- 1984-11-16 DE DE19843441975 patent/DE3441975A1/de active Granted
- 1984-11-16 OA OA58442A patent/OA07865A/xx unknown
- 1984-11-16 SE SE8405754A patent/SE458277B/sv not_active IP Right Cessation
- 1984-11-16 JP JP59240900A patent/JPS60116685A/ja active Granted
- 1984-11-16 IE IE294784A patent/IE58097B1/en not_active IP Right Cessation
- 1984-11-19 AT AT0365584A patent/AT391868B/de not_active IP Right Cessation
-
1987
- 1987-06-17 SG SG52687A patent/SG52687G/en unknown
- 1987-07-01 MY MYPI87000926A patent/MY100665A/en unknown
- 1987-10-22 HK HK779/87A patent/HK77987A/xx not_active IP Right Cessation
Also Published As
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