DE2549745A1 - Durch einen chromonylrest substituierte propionsaeuren sowie deren derivate und verwendungen - Google Patents
Durch einen chromonylrest substituierte propionsaeuren sowie deren derivate und verwendungenInfo
- Publication number
- DE2549745A1 DE2549745A1 DE19752549745 DE2549745A DE2549745A1 DE 2549745 A1 DE2549745 A1 DE 2549745A1 DE 19752549745 DE19752549745 DE 19752549745 DE 2549745 A DE2549745 A DE 2549745A DE 2549745 A1 DE2549745 A1 DE 2549745A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- formula
- acid
- propionic
- active ingredient
- 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.)
- Withdrawn
Links
- 150000004672 propanoic acids Chemical group 0.000 title claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 235000019260 propionic acid Nutrition 0.000 claims 5
- 235000011054 acetic acid Nutrition 0.000 claims 4
- 150000001243 acetic acids Chemical class 0.000 claims 4
- 230000000202 analgesic effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- CRALYSAZODAWCQ-UHFFFAOYSA-N 2-(bromomethyl)chromen-4-one Chemical compound C1=CC=C2OC(CBr)=CC(=O)C2=C1 CRALYSAZODAWCQ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- -1 alkali metal cyanide Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 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 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims 2
- 239000012312 sodium hydride Substances 0.000 claims 2
- RBLLVZMGRMNJEO-UHFFFAOYSA-N 2-[2-(4-oxochromen-2-yl)phenyl]propanoic acid Chemical group OC(=O)C(C)C1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 RBLLVZMGRMNJEO-UHFFFAOYSA-N 0.000 claims 1
- CEJINNSYZFLSCS-UHFFFAOYSA-N 2-hydroxy-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)CO CEJINNSYZFLSCS-UHFFFAOYSA-N 0.000 claims 1
- YNPDFBFVMJNGKZ-UHFFFAOYSA-N BTB10270 Natural products CC(=O)C1=CC(C)=CC=C1O YNPDFBFVMJNGKZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 150000003151 propanoic acid esters Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7438080A FR2291745A1 (fr) | 1974-11-20 | 1974-11-20 | Nouveaux acides inferieurs substitues par un radical chromonyl, leurs derives et leurs applications |
| FR7531024A FR2326919A2 (fr) | 1975-10-10 | 1975-10-10 | Nouveaux acides inferieurs substitues par un radical chromonyle, leurs derives et leurs applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2549745A1 true DE2549745A1 (de) | 1976-05-26 |
Family
ID=26218606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752549745 Withdrawn DE2549745A1 (de) | 1974-11-20 | 1975-11-06 | Durch einen chromonylrest substituierte propionsaeuren sowie deren derivate und verwendungen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4097582A (en:Method) |
| JP (1) | JPS6039676B2 (en:Method) |
| AT (1) | AT345829B (en:Method) |
| CA (1) | CA1067074A (en:Method) |
| CH (1) | CH612193A5 (en:Method) |
| DD (1) | DD128866A5 (en:Method) |
| DE (1) | DE2549745A1 (en:Method) |
| DK (1) | DK519975A (en:Method) |
| ES (1) | ES442616A1 (en:Method) |
| GB (1) | GB1512537A (en:Method) |
| IE (1) | IE43539B1 (en:Method) |
| IL (1) | IL48465A (en:Method) |
| MX (1) | MX3009E (en:Method) |
| NL (1) | NL7513597A (en:Method) |
| NO (1) | NO146636C (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125870C2 (de) * | 1980-07-09 | 1994-09-15 | William John Louis | 3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel |
| FR2516922A1 (fr) * | 1981-11-25 | 1983-05-27 | Lipha | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
| JPS61118380A (ja) * | 1984-11-14 | 1986-06-05 | Shionogi & Co Ltd | 新規な１，４−ベンゾジオキサンおよび１，４−ベンゾジオキシン誘導体ならびにその製造法 |
| US5116954A (en) * | 1988-04-06 | 1992-05-26 | Lipha, Lyonnaise Industrielle Pharmaceutique | Pharmaceutically useful flavonoic compounds containing at least one substituent on the benzopyranone ring moiety |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1499323A (en) * | 1974-03-22 | 1978-02-01 | Fisons Ltd | 6-substituted chromones and chromanones |
-
1975
- 1975-11-06 DE DE19752549745 patent/DE2549745A1/de not_active Withdrawn
- 1975-11-11 CH CH1460375A patent/CH612193A5/xx not_active IP Right Cessation
- 1975-11-11 IL IL48465A patent/IL48465A/xx unknown
- 1975-11-12 US US05/631,401 patent/US4097582A/en not_active Expired - Lifetime
- 1975-11-14 CA CA239,665A patent/CA1067074A/en not_active Expired
- 1975-11-14 ES ES442616A patent/ES442616A1/es not_active Expired
- 1975-11-18 IE IE2518/75A patent/IE43539B1/en unknown
- 1975-11-19 NO NO753886A patent/NO146636C/no unknown
- 1975-11-19 MX MX002840U patent/MX3009E/es unknown
- 1975-11-19 DK DK519975A patent/DK519975A/da not_active Application Discontinuation
- 1975-11-19 GB GB47707/75A patent/GB1512537A/en not_active Expired
- 1975-11-20 NL NL7513597A patent/NL7513597A/xx not_active Application Discontinuation
- 1975-11-20 DD DD7500189584A patent/DD128866A5/xx unknown
- 1975-11-20 JP JP50138775A patent/JPS6039676B2/ja not_active Expired
- 1975-11-20 AT AT884275A patent/AT345829B/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| J. Indian Chem. Soc., 1973, 50-295-8 * |
Also Published As
| Publication number | Publication date |
|---|---|
| NO146636B (no) | 1982-08-02 |
| IE43539L (en) | 1976-05-20 |
| DD128866A5 (de) | 1977-12-14 |
| ES442616A1 (es) | 1977-12-01 |
| DK519975A (da) | 1976-05-21 |
| NO146636C (no) | 1982-11-10 |
| NO753886L (en:Method) | 1976-05-21 |
| AT345829B (de) | 1978-10-10 |
| GB1512537A (en) | 1978-06-01 |
| AU8670775A (en) | 1977-05-26 |
| MX3009E (es) | 1980-01-28 |
| IE43539B1 (en) | 1981-03-25 |
| IL48465A0 (en) | 1976-01-30 |
| IL48465A (en) | 1981-06-29 |
| ATA884275A (de) | 1978-02-15 |
| JPS6039676B2 (ja) | 1985-09-06 |
| US4097582A (en) | 1978-06-27 |
| CH612193A5 (en:Method) | 1979-07-13 |
| NL7513597A (nl) | 1976-05-24 |
| CA1067074A (en) | 1979-11-27 |
| JPS51125288A (en) | 1976-11-01 |
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