CS208769B2 - Method of making the tetracyklononane derivatives - Google Patents
Method of making the tetracyklononane derivatives Download PDFInfo
- Publication number
- CS208769B2 CS208769B2 CS788846A CS884678A CS208769B2 CS 208769 B2 CS208769 B2 CS 208769B2 CS 788846 A CS788846 A CS 788846A CS 884678 A CS884678 A CS 884678A CS 208769 B2 CS208769 B2 CS 208769B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- radical
- formula
- mixture
- hydrogen
- nonane
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 51
- -1 alkyl radical Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
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- 229910052736 halogen Inorganic materials 0.000 claims 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
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- 150000001721 carbon Chemical group 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 231100000516 lung damage Toxicity 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002941 microtiter virus yield reduction assay Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 210000001989 nasopharynx Anatomy 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- QIWNOVRXWQPVIY-UHFFFAOYSA-N propylbenzene Chemical compound [CH2]CCC1=CC=CC=C1 QIWNOVRXWQPVIY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/16—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings
- C07C211/19—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5344677 | 1977-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208769B2 true CS208769B2 (en) | 1981-09-15 |
Family
ID=10467839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788846A CS208769B2 (en) | 1977-12-22 | 1978-12-22 | Method of making the tetracyklononane derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4357352A (en]) |
| EP (1) | EP0002896B1 (en]) |
| JP (1) | JPS5490167A (en]) |
| AT (1) | AT363923B (en]) |
| AU (1) | AU517387B2 (en]) |
| CA (1) | CA1118792A (en]) |
| CS (1) | CS208769B2 (en]) |
| DD (1) | DD140843A5 (en]) |
| DE (1) | DE2861796D1 (en]) |
| DK (1) | DK150299C (en]) |
| ES (1) | ES476241A1 (en]) |
| FI (1) | FI66347C (en]) |
| HU (1) | HU177222B (en]) |
| IL (1) | IL56167A (en]) |
| IT (1) | IT1110868B (en]) |
| NO (1) | NO149471C (en]) |
| NZ (1) | NZ189087A (en]) |
| PT (1) | PT68974A (en]) |
| SU (1) | SU1156591A3 (en]) |
| YU (1) | YU40544B (en]) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA822158B (en]) * | 1980-12-30 | 1984-10-01 | ||
| US4668703A (en) * | 1983-07-07 | 1987-05-26 | Syntex (U.S.A.) Inc. | γ-allenyl-γ-aminobutyric acids |
| JPS63188770U (en]) * | 1987-05-25 | 1988-12-05 | ||
| US5414011A (en) * | 1987-09-11 | 1995-05-09 | Syntex (U.S.A.) Inc. | Preservative system for ophthalmic formulations |
| US6150398A (en) * | 1991-05-08 | 2000-11-21 | The United States Of America As Represented By The Department Of Health And Human Services | Methods for the treatment of cancer |
| US5645988A (en) * | 1991-05-08 | 1997-07-08 | The United States Of America As Represented By The Department Of Health And Human Services | Methods of identifying drugs with selective effects against cancer cells |
| US20030225044A1 (en) * | 2002-06-03 | 2003-12-04 | Bachman Stephen E. | Method to increase serum levels of vitamins in animals including humans |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418368A (en) * | 1965-03-24 | 1968-12-24 | Smith Kline French Lab | Pentacyclo[6.2.0.02,6.03,10.05,9] decaneamines |
| US3456008A (en) * | 1965-10-11 | 1969-07-15 | Smithkline Corp | Aminopolycyclodecanes |
| CH472364A (de) | 1966-12-22 | 1969-05-15 | Geigy Ag J R | Verfahren zur Herstellung eines neuen polycyclischen Amins |
| US3496228A (en) * | 1967-02-16 | 1970-02-17 | Smithkline Corp | Aminotricyclononanes and the salts thereof |
-
1978
- 1978-12-01 CA CA000317203A patent/CA1118792A/en not_active Expired
- 1978-12-04 NZ NZ189087A patent/NZ189087A/xx unknown
- 1978-12-04 US US05/967,794 patent/US4357352A/en not_active Expired - Lifetime
- 1978-12-06 AU AU42241/78A patent/AU517387B2/en not_active Expired
- 1978-12-06 DE DE7878300756T patent/DE2861796D1/de not_active Expired
- 1978-12-06 EP EP78300756A patent/EP0002896B1/en not_active Expired
- 1978-12-10 IL IL56167A patent/IL56167A/xx unknown
- 1978-12-13 DK DK560278A patent/DK150299C/da not_active IP Right Cessation
- 1978-12-18 HU HU78IE855A patent/HU177222B/hu unknown
- 1978-12-19 IT IT52360/78A patent/IT1110868B/it active
- 1978-12-21 ES ES476241A patent/ES476241A1/es not_active Expired
- 1978-12-21 DD DD78210062A patent/DD140843A5/de unknown
- 1978-12-21 YU YU3037/78A patent/YU40544B/xx unknown
- 1978-12-21 AT AT0913078A patent/AT363923B/de not_active IP Right Cessation
- 1978-12-21 FI FI783948A patent/FI66347C/fi not_active IP Right Cessation
- 1978-12-21 NO NO784325A patent/NO149471C/no unknown
- 1978-12-22 JP JP15776378A patent/JPS5490167A/ja active Granted
- 1978-12-22 PT PT68974A patent/PT68974A/pt unknown
- 1978-12-22 SU SU782699554A patent/SU1156591A3/ru active
- 1978-12-22 CS CS788846A patent/CS208769B2/cs unknown
-
1982
- 1982-08-17 US US06/408,919 patent/US4454157A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO149471B (no) | 1984-01-16 |
| AT363923B (de) | 1981-09-10 |
| JPS5490167A (en) | 1979-07-17 |
| NZ189087A (en) | 1980-11-14 |
| EP0002896A1 (en) | 1979-07-11 |
| ES476241A1 (es) | 1979-04-16 |
| JPS6214539B2 (en]) | 1987-04-02 |
| FI783948A7 (fi) | 1979-06-23 |
| IL56167A (en) | 1982-09-30 |
| DK150299B (da) | 1987-02-02 |
| FI66347C (fi) | 1984-10-10 |
| IT7852360A0 (it) | 1978-12-19 |
| ATA913078A (de) | 1981-02-15 |
| DD140843A5 (de) | 1980-04-02 |
| CA1118792A (en) | 1982-02-23 |
| IT1110868B (it) | 1986-01-06 |
| US4357352A (en) | 1982-11-02 |
| IL56167A0 (en) | 1979-03-12 |
| DK150299C (da) | 1987-10-26 |
| NO784325L (no) | 1979-07-27 |
| US4454157A (en) | 1984-06-12 |
| YU303778A (en) | 1983-01-21 |
| YU40544B (en) | 1986-02-28 |
| DE2861796D1 (en) | 1982-06-24 |
| AU517387B2 (en) | 1981-07-30 |
| SU1156591A3 (ru) | 1985-05-15 |
| DK560278A (da) | 1979-06-23 |
| HU177222B (en) | 1981-08-28 |
| AU4224178A (en) | 1979-06-28 |
| PT68974A (en) | 1979-01-01 |
| FI66347B (fi) | 1984-06-29 |
| NO149471C (no) | 1984-04-25 |
| EP0002896B1 (en) | 1982-05-05 |
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