IL43947A - Method of treating immunological or inflammatory disorders with dexamethasone 21-adamantane-1' carboxylate and compositions containing adamantane carboxylates of 21-hydroxy pregnanes - Google Patents
Method of treating immunological or inflammatory disorders with dexamethasone 21-adamantane-1' carboxylate and compositions containing adamantane carboxylates of 21-hydroxy pregnanesInfo
- Publication number
- IL43947A IL43947A IL43947A IL4394774A IL43947A IL 43947 A IL43947 A IL 43947A IL 43947 A IL43947 A IL 43947A IL 4394774 A IL4394774 A IL 4394774A IL 43947 A IL43947 A IL 43947A
- Authority
- IL
- Israel
- Prior art keywords
- dosage
- adamantane
- carboxylate
- betamethasone
- days
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 17
- 229960003957 dexamethasone Drugs 0.000 title claims description 14
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 230000001900 immune effect Effects 0.000 title claims description 9
- 150000007942 carboxylates Chemical class 0.000 title claims description 3
- 208000026278 immune system disease Diseases 0.000 title claims description 3
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical class C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 title description 3
- 208000027866 inflammatory disease Diseases 0.000 title description 3
- 229960002537 betamethasone Drugs 0.000 claims description 25
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 22
- 241001465754 Metazoa Species 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000007918 intramuscular administration Methods 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 description 30
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- -1 ADAMANTANE CARBOXYLATES Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000004968 inflammatory condition Effects 0.000 description 6
- 229960004217 benzyl alcohol Drugs 0.000 description 5
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- 230000008105 immune reaction Effects 0.000 description 4
- 229920000136 polysorbate Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000007475 hemolytic anemia Diseases 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 206010043561 Thrombocytopenic purpura Diseases 0.000 description 2
- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 230000037189 immune system physiology Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 229940102213 injectable suspension Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- VBJGJHBYWREJQD-UHFFFAOYSA-M sodium;dihydrogen phosphate;dihydrate Chemical compound O.O.[Na+].OP(O)([O-])=O VBJGJHBYWREJQD-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012455 Dermatitis exfoliative Diseases 0.000 description 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
- 241000214474 Doa Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000007465 Giant cell arteritis Diseases 0.000 description 1
- 208000001204 Hashimoto Disease Diseases 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000005279 Status Asthmaticus Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010044608 Trichiniasis Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005585 adamantoate group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 208000004526 exfoliative dermatitis Diseases 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000008095 long lasting therapeutic effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 206010043207 temporal arteritis Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44773 | 1973-01-03 | ||
| GB44873 | 1973-01-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43947A0 IL43947A0 (en) | 1974-05-16 |
| IL43947A true IL43947A (en) | 1977-08-31 |
Family
ID=26235930
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43947A IL43947A (en) | 1973-01-03 | 1974-01-02 | Method of treating immunological or inflammatory disorders with dexamethasone 21-adamantane-1' carboxylate and compositions containing adamantane carboxylates of 21-hydroxy pregnanes |
| IL43948A IL43948A (en) | 1973-01-03 | 1974-01-02 | Adamantane carboxylates of 21-hydroxy pregnanes and compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43948A IL43948A (en) | 1973-01-03 | 1974-01-02 | Adamantane carboxylates of 21-hydroxy pregnanes and compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5024427A (enrdf_load_stackoverflow) |
| AU (2) | AU6420174A (enrdf_load_stackoverflow) |
| BE (2) | BE809342A (enrdf_load_stackoverflow) |
| DE (2) | DE2400038A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2212153B1 (enrdf_load_stackoverflow) |
| IL (2) | IL43947A (enrdf_load_stackoverflow) |
| LU (2) | LU69097A1 (enrdf_load_stackoverflow) |
| NL (2) | NL7400013A (enrdf_load_stackoverflow) |
| SE (1) | SE7400020L (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60161914A (ja) * | 1984-02-02 | 1985-08-23 | Green Cross Corp:The | ステロイド脂肪酸エステル含有直腸投与製剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1473909A (fr) * | 1965-11-16 | 1967-03-24 | Lilly Co Eli | Procédé de préparation de nouveaux esters de corticostéroïdes |
| BE785812A (fr) * | 1971-07-05 | 1973-01-04 | Glaxo Lab Ltd | Nouveaux composes steroides |
-
1973
- 1973-12-27 JP JP48144564A patent/JPS5024427A/ja active Pending
- 1973-12-27 JP JP48144563A patent/JPS49116217A/ja active Pending
-
1974
- 1974-01-02 NL NL7400013A patent/NL7400013A/xx unknown
- 1974-01-02 LU LU69097A patent/LU69097A1/xx unknown
- 1974-01-02 IL IL43947A patent/IL43947A/en unknown
- 1974-01-02 IL IL43948A patent/IL43948A/en unknown
- 1974-01-02 BE BE139473A patent/BE809342A/xx unknown
- 1974-01-02 DE DE2400038A patent/DE2400038A1/de active Pending
- 1974-01-02 LU LU69096A patent/LU69096A1/xx unknown
- 1974-01-02 FR FR7400067A patent/FR2212153B1/fr not_active Expired
- 1974-01-02 DE DE2400005A patent/DE2400005A1/de active Pending
- 1974-01-02 FR FR7400066A patent/FR2212152A1/fr active Granted
- 1974-01-02 BE BE139472A patent/BE809341A/xx unknown
- 1974-01-02 SE SE7400020A patent/SE7400020L/xx not_active Application Discontinuation
- 1974-01-02 NL NL7400014A patent/NL7400014A/xx unknown
- 1974-01-04 AU AU64201/74A patent/AU6420174A/en not_active Expired
- 1974-01-04 AU AU64202/74A patent/AU6420274A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2212153B1 (enrdf_load_stackoverflow) | 1976-12-17 |
| LU69096A1 (enrdf_load_stackoverflow) | 1974-04-02 |
| IL43948A (en) | 1977-08-31 |
| IL43948A0 (en) | 1974-05-16 |
| JPS49116217A (enrdf_load_stackoverflow) | 1974-11-06 |
| AU6420274A (en) | 1975-07-10 |
| JPS5024427A (enrdf_load_stackoverflow) | 1975-03-15 |
| FR2212152A1 (en) | 1974-07-26 |
| NL7400013A (enrdf_load_stackoverflow) | 1974-07-05 |
| NL7400014A (enrdf_load_stackoverflow) | 1974-07-05 |
| SE7400020L (enrdf_load_stackoverflow) | 1974-07-03 |
| AU6420174A (en) | 1975-07-10 |
| FR2212153A1 (enrdf_load_stackoverflow) | 1974-07-26 |
| DE2400038A1 (de) | 1974-07-04 |
| BE809341A (fr) | 1974-07-02 |
| IL43947A0 (en) | 1974-05-16 |
| LU69097A1 (enrdf_load_stackoverflow) | 1974-04-02 |
| BE809342A (fr) | 1974-07-02 |
| FR2212152B1 (enrdf_load_stackoverflow) | 1977-03-25 |
| DE2400005A1 (de) | 1974-07-04 |
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