DE3024305A1 - Parenteral verabfolgbares psychotropes arzneipraeparat mit langzeitwirkung - Google Patents
Parenteral verabfolgbares psychotropes arzneipraeparat mit langzeitwirkungInfo
- Publication number
- DE3024305A1 DE3024305A1 DE19803024305 DE3024305A DE3024305A1 DE 3024305 A1 DE3024305 A1 DE 3024305A1 DE 19803024305 DE19803024305 DE 19803024305 DE 3024305 A DE3024305 A DE 3024305A DE 3024305 A1 DE3024305 A1 DE 3024305A1
- Authority
- DE
- Germany
- Prior art keywords
- long
- preparation according
- fluorophenyl
- preparation
- piperidinyl
- 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
- 230000007774 longterm Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 claims description 23
- 230000000506 psychotropic effect Effects 0.000 claims description 8
- 239000008159 sesame oil Substances 0.000 claims description 8
- 235000011803 sesame oil Nutrition 0.000 claims description 8
- 150000001954 decanoic acid esters Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- GUTXTARXLVFHDK-UHFFFAOYSA-N Haloperidol decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 GUTXTARXLVFHDK-UHFFFAOYSA-N 0.000 claims description 4
- ZINCPWWBSRSXBH-UHFFFAOYSA-N [4-(4-bromophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 ZINCPWWBSRSXBH-UHFFFAOYSA-N 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 238000011866 long-term treatment Methods 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- RKLNONIVDFXQRX-UHFFFAOYSA-N Bromperidol Chemical compound C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 RKLNONIVDFXQRX-UHFFFAOYSA-N 0.000 description 10
- 229960004037 bromperidol Drugs 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 5
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000008673 vomiting Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 229960003878 haloperidol Drugs 0.000 description 4
- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960003990 apomorphine hydrochloride Drugs 0.000 description 3
- 229960004284 bromperidol decanoate Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000004089 psychotropic agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 229960002341 trifluperidol Drugs 0.000 description 3
- GPMXUUPHFNMNDH-UHFFFAOYSA-N trifluperidol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC(=O)C1=CC=C(F)C=C1 GPMXUUPHFNMNDH-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960005007 haloperidol decanoate Drugs 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 decanoate ester Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Anesthesiology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8082679A JPS568318A (en) | 1979-06-28 | 1979-06-28 | Non oral long acting composition of haloperidol and bromperidol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3024305A1 true DE3024305A1 (de) | 1981-01-22 |
| DE3024305C2 DE3024305C2 (enExample) | 1989-12-07 |
Family
ID=13729223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803024305 Granted DE3024305A1 (de) | 1979-06-28 | 1980-06-27 | Parenteral verabfolgbares psychotropes arzneipraeparat mit langzeitwirkung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS568318A (enExample) |
| BE (1) | BE883994A (enExample) |
| CY (1) | CY1255A (enExample) |
| DE (1) | DE3024305A1 (enExample) |
| FR (1) | FR2460932A1 (enExample) |
| GB (1) | GB2054371B (enExample) |
| HK (1) | HK83384A (enExample) |
| KE (1) | KE3427A (enExample) |
| NL (1) | NL190775C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998018769A1 (en) * | 1996-10-31 | 1998-05-07 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Sustained-release derivatives of hydroxylated analogs of substituted 1-[2[bis(aryl)methoxy]ethyl]-piperazines and -homopiperazines and their use as noncompetitive antagonists of dopamine reuptake |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8621892D0 (en) * | 1986-09-11 | 1986-10-15 | Lundbeck & Co As H | Organic compound |
| DK238190D0 (da) * | 1990-10-03 | 1990-10-03 | Lundbeck & Co As H | Depotderivater |
| EP0669128B1 (en) * | 1992-11-17 | 2000-01-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Sustained-release microsphere containing antipsychotic and process for producing the same |
| RU2178297C1 (ru) * | 2001-02-02 | 2002-01-20 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Фармацевтическая композиция, обладающая антипсихотическим и противорвотным действием, и способ ее получения |
| BRPI0517701A8 (pt) | 2004-11-10 | 2018-01-23 | Genzyme Corp | métodos de tratamento de diabetes mellitus |
| ES2546181T3 (es) | 2006-05-09 | 2015-09-21 | Genzyme Corporation | Métodos de tratar la enfermedad del hígado graso mediante inhibición de la síntesis de glucoesfingolípidos |
| EP2594565B1 (en) | 2007-05-31 | 2018-10-24 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitors |
| KR101640263B1 (ko) | 2007-10-05 | 2016-07-15 | 젠자임 코포레이션 | 세라마이드 유도체로 다낭성 신장질환을 치료하는 방법 |
| JP2011529500A (ja) | 2008-07-28 | 2011-12-08 | ジェンザイム コーポレーション | 虚脱性糸球体症および他の糸球体疾患の処置のためのグルコシルセラミドシンターゼ阻害 |
| CN102271678B (zh) | 2008-10-03 | 2017-06-30 | 简詹姆公司 | 2‑酰胺基丙醇型葡糖神经酰胺合成酶抑制剂 |
| ES2972387T3 (es) | 2011-03-18 | 2024-06-12 | Alkermes Pharma Ireland Ltd | Composiciones farmacéuticas que comprenden ésteres de sorbitán |
| CN103301461B (zh) * | 2012-03-08 | 2018-09-07 | 江苏豪森药业集团有限公司 | 一种长效注射制剂及其制备方法和用途 |
| US9999670B2 (en) | 2012-03-19 | 2018-06-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| WO2013142202A1 (en) | 2012-03-19 | 2013-09-26 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising glycerol esters |
| CA2867121C (en) | 2012-03-19 | 2021-05-25 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| JP6654042B2 (ja) | 2012-09-19 | 2020-02-26 | アルカームス ファーマ アイルランド リミテッド | 貯蔵安定性が改善された医薬組成物 |
| AU2015231278B2 (en) | 2014-03-20 | 2020-01-23 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| AU2019230014B2 (en) | 2018-03-05 | 2024-11-28 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| CN113117092A (zh) * | 2020-01-14 | 2021-07-16 | 中国科学院上海药物研究所 | 一种非水缓释递药系统 |
| HUP2100259A1 (hu) | 2021-07-07 | 2023-01-28 | Richter Gedeon Nyrt | Cariprazine tartalmú szabályozott hatóanyag-leadású injekciós készítmények |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408356A (en) * | 1965-08-31 | 1968-10-29 | Squibb & Sons Inc | Long chain esters of 4'-fluoro-4-[4-hydroxy-4-(alpha, alpha, alpha-trifluorotolyl)piperi-dino]butyrophenone and the like |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695194A1 (de) * | 1966-07-11 | 1971-03-18 | Hoffmann La Roche | Verfahren zur Herstellung von Piperidinderivaten |
| US3850935A (en) * | 1971-10-16 | 1974-11-26 | Sumitomo Chemical Co | Process for producing piperidine derivatives by degrading quaternary piperidinium salts |
-
1979
- 1979-06-28 JP JP8082679A patent/JPS568318A/ja active Pending
-
1980
- 1980-06-03 GB GB8018117A patent/GB2054371B/en not_active Expired
- 1980-06-03 CY CY1255A patent/CY1255A/en unknown
- 1980-06-20 NL NL8003583A patent/NL190775C/xx not_active IP Right Cessation
- 1980-06-25 BE BE0/201165A patent/BE883994A/fr not_active IP Right Cessation
- 1980-06-27 DE DE19803024305 patent/DE3024305A1/de active Granted
- 1980-06-27 FR FR8014443A patent/FR2460932A1/fr active Granted
-
1984
- 1984-07-20 KE KE3427A patent/KE3427A/xx unknown
- 1984-11-01 HK HK833/84A patent/HK83384A/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408356A (en) * | 1965-08-31 | 1968-10-29 | Squibb & Sons Inc | Long chain esters of 4'-fluoro-4-[4-hydroxy-4-(alpha, alpha, alpha-trifluorotolyl)piperi-dino]butyrophenone and the like |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998018769A1 (en) * | 1996-10-31 | 1998-05-07 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Sustained-release derivatives of hydroxylated analogs of substituted 1-[2[bis(aryl)methoxy]ethyl]-piperazines and -homopiperazines and their use as noncompetitive antagonists of dopamine reuptake |
| US6387389B1 (en) | 1996-10-31 | 2002-05-14 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Sustained-release derivatives of hydroxylated analogs of substituted 1-[2[bis(aryl)methoxy]ethyl]-piperazines and -homopiperazines and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2460932B1 (enExample) | 1984-11-16 |
| GB2054371A (en) | 1981-02-18 |
| CY1255A (en) | 1984-08-31 |
| BE883994A (fr) | 1980-12-29 |
| FR2460932A1 (fr) | 1981-01-30 |
| KE3427A (en) | 1984-08-10 |
| NL190775B (nl) | 1994-03-16 |
| NL8003583A (nl) | 1980-12-30 |
| GB2054371B (en) | 1983-08-03 |
| NL190775C (nl) | 1994-08-16 |
| DE3024305C2 (enExample) | 1989-12-07 |
| JPS568318A (en) | 1981-01-28 |
| HK83384A (en) | 1984-11-09 |
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