NO802014L - Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-pyridinderivater - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-pyridinderivaterInfo
- Publication number
- NO802014L NO802014L NO802014A NO802014A NO802014L NO 802014 L NO802014 L NO 802014L NO 802014 A NO802014 A NO 802014A NO 802014 A NO802014 A NO 802014A NO 802014 L NO802014 L NO 802014L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- pyridine
- pyrrolo
- bromine
- tetrahydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000005255 pyrrolopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- -1 pyrrolidino-methyl Chemical group 0.000 claims description 4
- WIBUSVGJVAYNBU-UHFFFAOYSA-N 4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=CN(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 WIBUSVGJVAYNBU-UHFFFAOYSA-N 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- YYLVBYQDRJYOTK-UHFFFAOYSA-N 4-phenyl-4,5,6,7-tetrahydro-1h-pyrrolo[2,3-c]pyridine Chemical class C1NCC=2NC=CC=2C1C1=CC=CC=C1 YYLVBYQDRJYOTK-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000006683 Mannich reaction Methods 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- CWLOFLFPSNCBFN-UHFFFAOYSA-N 2-bromo-4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=C(Br)N(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 CWLOFLFPSNCBFN-UHFFFAOYSA-N 0.000 claims 1
- GYNPKCPHHBWISN-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3,6-trimethyl-2-piperidin-1-yl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridine Chemical compound CN1C(=C(C2=C1CN(CC2C2=CC=C(C=C2)Br)C)C)N2CCCCC2 GYNPKCPHHBWISN-UHFFFAOYSA-N 0.000 claims 1
- LNVJOEISRQDAHH-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3,6-trimethyl-2-pyrrolidin-1-yl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridine Chemical compound CN1C(=C(C2=C1CN(CC2C2=CC=C(C=C2)Br)C)C)N2CCCC2 LNVJOEISRQDAHH-UHFFFAOYSA-N 0.000 claims 1
- HQVOLDSMHIXLGI-UHFFFAOYSA-N 4-(4-bromophenyl)-1-methyl-4,5,6,7-tetrahydropyrrolo[2,3-c]pyridine Chemical compound C1NCC=2N(C)C=CC=2C1C1=CC=C(Br)C=C1 HQVOLDSMHIXLGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 210000004720 cerebrum Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002871 norepinephrines Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792927294 DE2927294A1 (de) | 1979-07-06 | 1979-07-06 | Neue 4-phenyl-4,5,6,7-tetrahydropyrrolo eckige klammer auf 2,3-c eckige klammer zu pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO802014L true NO802014L (no) | 1981-01-07 |
Family
ID=6075042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO802014A NO802014L (no) | 1979-07-06 | 1980-07-04 | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-pyridinderivater |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4315938A (xx) |
| JP (1) | JPS5610184A (xx) |
| AT (1) | AT375077B (xx) |
| AU (1) | AU536336B2 (xx) |
| BE (1) | BE884193A (xx) |
| CA (1) | CA1138864A (xx) |
| CH (1) | CH649548A5 (xx) |
| DE (1) | DE2927294A1 (xx) |
| DK (1) | DK290380A (xx) |
| ES (1) | ES8201019A1 (xx) |
| FI (1) | FI802148A (xx) |
| FR (1) | FR2460950A1 (xx) |
| GB (1) | GB2054580B (xx) |
| GR (1) | GR69327B (xx) |
| HU (1) | HU182152B (xx) |
| IL (1) | IL60499A (xx) |
| IT (1) | IT1150024B (xx) |
| LU (1) | LU82582A1 (xx) |
| NL (1) | NL8003879A (xx) |
| NO (1) | NO802014L (xx) |
| NZ (1) | NZ194245A (xx) |
| PH (1) | PH15756A (xx) |
| PT (1) | PT71500B (xx) |
| SE (1) | SE436747B (xx) |
| YU (1) | YU174780A (xx) |
| ZA (1) | ZA804031B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5890951A (ja) * | 1981-11-26 | 1983-05-30 | 住友金属工業株式会社 | 耐食性にすぐれた積層板 |
| JPS59193175A (ja) * | 1983-04-19 | 1984-11-01 | Toa Nenryo Kogyo Kk | 積層物 |
| US4572911A (en) * | 1984-08-02 | 1986-02-25 | Mcneilab, Inc. | Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates |
| US20220267277A1 (en) * | 2019-07-30 | 2022-08-25 | Sanford Burnham Prebys Medical Discovery Institute | Dopamine receptor d1 agonists and methods of use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1484140A (en) * | 1974-04-24 | 1977-08-24 | Wyeth John & Brother Ltd | Pyrrolopyridine derivatives |
| AT368504B (de) * | 1977-10-15 | 1982-10-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 4-phenyl-thieno- (2,3-c)-piperidine |
-
1979
- 1979-07-06 DE DE19792927294 patent/DE2927294A1/de not_active Withdrawn
-
1980
- 1980-06-30 US US06/163,969 patent/US4315938A/en not_active Expired - Lifetime
- 1980-06-30 IT IT23120/80A patent/IT1150024B/it active
- 1980-07-02 AT AT0344680A patent/AT375077B/de not_active IP Right Cessation
- 1980-07-03 YU YU01747/80A patent/YU174780A/xx unknown
- 1980-07-03 CH CH5125/80A patent/CH649548A5/de not_active IP Right Cessation
- 1980-07-03 GR GR62353A patent/GR69327B/el unknown
- 1980-07-04 FR FR8015010A patent/FR2460950A1/fr active Granted
- 1980-07-04 AU AU60138/80A patent/AU536336B2/en not_active Ceased
- 1980-07-04 LU LU82582A patent/LU82582A1/de unknown
- 1980-07-04 FI FI802148A patent/FI802148A/fi not_active Application Discontinuation
- 1980-07-04 NZ NZ194245A patent/NZ194245A/en unknown
- 1980-07-04 NL NL8003879A patent/NL8003879A/nl not_active Application Discontinuation
- 1980-07-04 GB GB8022046A patent/GB2054580B/en not_active Expired
- 1980-07-04 NO NO802014A patent/NO802014L/no unknown
- 1980-07-04 BE BE0/201313A patent/BE884193A/fr not_active IP Right Cessation
- 1980-07-04 PT PT71500A patent/PT71500B/pt unknown
- 1980-07-04 DK DK290380A patent/DK290380A/da not_active Application Discontinuation
- 1980-07-04 CA CA000355540A patent/CA1138864A/en not_active Expired
- 1980-07-04 HU HU801678A patent/HU182152B/hu unknown
- 1980-07-04 JP JP9161580A patent/JPS5610184A/ja active Pending
- 1980-07-04 IL IL60499A patent/IL60499A/xx unknown
- 1980-07-04 ES ES493104A patent/ES8201019A1/es not_active Expired
- 1980-07-04 ZA ZA00804031A patent/ZA804031B/xx unknown
- 1980-07-04 SE SE8004976A patent/SE436747B/sv unknown
- 1980-07-07 PH PH24246A patent/PH15756A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA804031B (en) | 1982-03-31 |
| FR2460950A1 (fr) | 1981-01-30 |
| DK290380A (da) | 1981-01-07 |
| ES493104A0 (es) | 1981-11-01 |
| NZ194245A (en) | 1984-07-06 |
| ATA344680A (de) | 1983-11-15 |
| AU536336B2 (en) | 1984-05-03 |
| IT1150024B (it) | 1986-12-10 |
| GB2054580A (en) | 1981-02-18 |
| IL60499A0 (en) | 1980-09-16 |
| ES8201019A1 (es) | 1981-11-01 |
| GB2054580B (en) | 1983-04-07 |
| PT71500A (de) | 1980-08-01 |
| SE8004976L (sv) | 1981-01-07 |
| FI802148A (fi) | 1981-01-07 |
| CH649548A5 (de) | 1985-05-31 |
| GR69327B (xx) | 1982-05-17 |
| BE884193A (fr) | 1981-01-05 |
| DE2927294A1 (de) | 1981-01-08 |
| FR2460950B1 (xx) | 1983-06-24 |
| LU82582A1 (de) | 1981-09-10 |
| IT8023120A0 (it) | 1980-06-30 |
| YU174780A (en) | 1983-02-28 |
| SE436747B (sv) | 1985-01-21 |
| HU182152B (en) | 1983-12-28 |
| US4315938A (en) | 1982-02-16 |
| AT375077B (de) | 1984-06-25 |
| IL60499A (en) | 1984-02-29 |
| JPS5610184A (en) | 1981-02-02 |
| CA1138864A (en) | 1983-01-04 |
| PH15756A (en) | 1983-03-18 |
| PT71500B (de) | 1981-12-11 |
| AU6013880A (en) | 1981-01-15 |
| NL8003879A (nl) | 1981-01-08 |
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