CH322242A - Verfahren zur Herstellung von ungesättigten 3-Tertiäramino-steroiden - Google Patents
Verfahren zur Herstellung von ungesättigten 3-Tertiäramino-steroidenInfo
- Publication number
- CH322242A CH322242A CH322242DA CH322242A CH 322242 A CH322242 A CH 322242A CH 322242D A CH322242D A CH 322242DA CH 322242 A CH322242 A CH 322242A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dione
- decomposition
- steroids
- keto
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 13
- 229960003387 progesterone Drugs 0.000 claims description 11
- 239000000186 progesterone Substances 0.000 claims description 11
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 claims description 6
- 229960005471 androstenedione Drugs 0.000 claims description 6
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003431 steroids Chemical class 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 229960003604 testosterone Drugs 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RZRPTBIGEANTGU-UHFFFAOYSA-N -Androst-4-ene-3,11,17-trione Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)=O)C4C3CCC2=C1 RZRPTBIGEANTGU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- RZRPTBIGEANTGU-IRIMSJTPSA-N adrenosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RZRPTBIGEANTGU-IRIMSJTPSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 19
- -1 steroid amine compounds Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 150000002081 enamines Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229930194542 Keto Natural products 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- WKAVAGKRWFGIEA-DADBAOPHSA-N 11-Ketoprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O WKAVAGKRWFGIEA-DADBAOPHSA-N 0.000 description 2
- WKAVAGKRWFGIEA-UHFFFAOYSA-N 11-Ketoprogesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2=O WKAVAGKRWFGIEA-UHFFFAOYSA-N 0.000 description 2
- PESKGJQREUXSRR-UXIWKSIVSA-N 5alpha-cholestan-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 PESKGJQREUXSRR-UXIWKSIVSA-N 0.000 description 2
- PESKGJQREUXSRR-UHFFFAOYSA-N 5beta-cholestanone Natural products C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 PESKGJQREUXSRR-UHFFFAOYSA-N 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000003613 bile acid Substances 0.000 description 2
- NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 description 2
- NYOXRYYXRWJDKP-UHFFFAOYSA-N cholestenone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 NYOXRYYXRWJDKP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CBMYJHIOYJEBSB-UHFFFAOYSA-N (10S)-3t.17t-Dihydroxy-10r.13c-dimethyl-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)O)C4C3CCC21 CBMYJHIOYJEBSB-UHFFFAOYSA-N 0.000 description 1
- ZJRFCEIUGPXQPH-PBDHEXIJSA-N (4R)-4-[(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pent-2-enoic acid Chemical class O=C1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=CC(=O)O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C ZJRFCEIUGPXQPH-PBDHEXIJSA-N 0.000 description 1
- KIQFUORWRVZTHT-PBDHEXIJSA-N (4r)-4-[(8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical class C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 KIQFUORWRVZTHT-PBDHEXIJSA-N 0.000 description 1
- RAJWOBJTTGJROA-UHFFFAOYSA-N (5alpha)-androstane-3,17-dione Natural products C1C(=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 RAJWOBJTTGJROA-UHFFFAOYSA-N 0.000 description 1
- NVKAWKQGWWIWPM-UXMGNZLBSA-N (5s,8r,9s,10s,13s,14s)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-UXMGNZLBSA-N 0.000 description 1
- HFVMLYAGWXSTQI-OJEXMJBDSA-N (8r,9s,10s,13r,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 HFVMLYAGWXSTQI-OJEXMJBDSA-N 0.000 description 1
- LNGLEOIUQBVRRY-JYQHCDCXSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,6-dione Chemical compound C1C(=O)C2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 LNGLEOIUQBVRRY-JYQHCDCXSA-N 0.000 description 1
- MKGZDUKUQPPHFM-XJZKHKOHSA-N (8s,9s,10r,13r,14s,17r)-17-[(2r,5s)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)C=C[C@@H](CC)C(C)C)[C@@]1(C)CC2 MKGZDUKUQPPHFM-XJZKHKOHSA-N 0.000 description 1
- JMAPHBFIBIHSIT-ZBKBXNIDSA-N (8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical class C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JMAPHBFIBIHSIT-ZBKBXNIDSA-N 0.000 description 1
- AHRWWYGWQKBKBF-ZCFUGHDASA-N (8s,9s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O AHRWWYGWQKBKBF-ZCFUGHDASA-N 0.000 description 1
- HBGDYSUQFCIKDU-HLXSIYPQSA-N 1-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-pyrrolidin-1-yl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound N1(CCCC1)C1=CC2=CC[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C HBGDYSUQFCIKDU-HLXSIYPQSA-N 0.000 description 1
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- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 1
- OKJCFMUGMSVJBG-MISPCMORSA-N 17beta-hydroxy-5beta-androst-1-en-3-one Chemical compound C1C(=O)C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@H]21 OKJCFMUGMSVJBG-MISPCMORSA-N 0.000 description 1
- OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical class C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 description 1
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- RAJWOBJTTGJROA-WZNAKSSCSA-N 5alpha-androstane-3,17-dione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 RAJWOBJTTGJROA-WZNAKSSCSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US288546A US2781342A (en) | 1952-05-17 | 1952-05-17 | Steroid enamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH322242A true CH322242A (de) | 1957-06-15 |
Family
ID=23107588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH322242D CH322242A (de) | 1952-05-17 | 1953-05-12 | Verfahren zur Herstellung von ungesättigten 3-Tertiäramino-steroiden |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT389703B (de) * | 1980-11-21 | 1990-01-25 | Roussel Uclaf | Verfahren zur herstellung von neuen 3-amino-substituierten steroidderivaten und von deren salzen |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053832A (en) * | 1957-04-29 | 1962-09-11 | Schering Corp | Alkylated cortical steroids |
| US2884416A (en) * | 1958-03-20 | 1959-04-28 | Upjohn Co | Mineral acid salts of pregnane-3, 11, 20-trione 3-enamines |
| US2919285A (en) * | 1958-11-03 | 1959-12-29 | Searle & Co | Preparation of 5alpha-pregnane-3, 20-dione from funtumine |
| NL270211A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-10-20 | |||
| US3207752A (en) * | 1961-11-23 | 1965-09-21 | Ormonoterapia Richter Spa | Process for the preparation of 2alpha-methyl-androstane derivatives |
| FR1334968A (fr) * | 1962-04-18 | 1963-08-16 | Roussel Uclaf | Nouveau procédé de préparation de lactones stéroïdes non saturées |
| NL123298C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-08-07 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2422904A (en) * | 1936-05-29 | 1947-06-24 | Schering Corp | Method of preparing delta1,4-androstadienol-17-one-3 and its derivatives |
| US2340388A (en) * | 1936-05-29 | 1944-02-01 | Schering Corp | Steroid compounds and a process of producing the same |
-
1952
- 1952-05-17 US US288546A patent/US2781342A/en not_active Expired - Lifetime
-
1953
- 1953-04-30 GB GB12016/53A patent/GB740568A/en not_active Expired
- 1953-05-06 FR FR1098526D patent/FR1098526A/fr not_active Expired
- 1953-05-12 CH CH322242D patent/CH322242A/de unknown
- 1953-05-16 NL NLAANVRAGE7709931,B patent/NL178369B/xx not_active IP Right Cessation
- 1953-05-16 NL NL178369A patent/NL85986C/xx active
- 1953-05-17 DE DEU2194A patent/DE951569C/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT389703B (de) * | 1980-11-21 | 1990-01-25 | Roussel Uclaf | Verfahren zur herstellung von neuen 3-amino-substituierten steroidderivaten und von deren salzen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE951569C (de) | 1956-10-31 |
| NL178369B (nl) | 1957-03-15 |
| FR1098526A (fr) | 1955-08-01 |
| GB740568A (en) | 1955-11-16 |
| US2781342A (en) | 1957-02-12 |
| NL85986C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1957-07-16 |
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