CH372300A - Verfahren zur Herstellung von 17-Estern des 19-Nortestosterons - Google Patents

Verfahren zur Herstellung von 17-Estern des 19-Nortestosterons

Info

Publication number: CH372300A
Authority: CH; Switzerland
Prior art keywords: sep; nortestosterone; effect; acid; ester
Prior art date: 1958-02-25

Application number

CH6965959A

Other languages

German (de)

English (en)

Inventor

Duyvene De Wit Erik

Anthony Dr Overbeek Gerhard

Original Assignee

Organon Nv

Priority date (The priority date 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 date listed.)

1958-02-25

Filing date

1959-02-17

Publication date

1963-10-15

1959-02-17 Application filed by Organon Nv filed Critical Organon Nv

1963-10-15 Publication of CH372300A publication Critical patent/CH372300A/de

Links

229960004719 nandrolone Drugs 0.000 title claims description 35
NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title description 2
-1 nonanecarboxylic acid halide Chemical class 0.000 claims description 16
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 claims description 2
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
230000001195 anabolic effect Effects 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
230000001548 androgenic effect Effects 0.000 description 15
230000000694 effects Effects 0.000 description 14
239000002253 acid Substances 0.000 description 13
150000002148 esters Chemical class 0.000 description 12
230000002349 favourable effect Effects 0.000 description 8
239000004312 hexamethylene tetramine Substances 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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 description 4
150000007513 acids Chemical class 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
239000005642 Oleic acid Substances 0.000 description 3
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000001792 virilizing effect Effects 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000005639 Lauric acid Substances 0.000 description 2
235000021360 Myristic acid Nutrition 0.000 description 2
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
235000021314 Palmitic acid Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
210000004907 gland Anatomy 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 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
229960003604 testosterone Drugs 0.000 description 2
229960002703 undecylenic acid Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
206010011985 Decubitus ulcer Diseases 0.000 description 1
206010053759 Growth retardation Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010031243 Osteogenesis imperfecta Diseases 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000282887 Suidae Species 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003549 asthenia Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000003450 decanoic acid ester group Chemical group 0.000 description 1
NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
231100000001 growth retardation Toxicity 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000000977 initiatory effect Effects 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
POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
230000014616 translation Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- 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)

CH6965959A 1958-02-25 1959-02-17 Verfahren zur Herstellung von 17-Estern des 19-Nortestosterons CH372300A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL225275		1958-02-25
NL234588		1958-12-23

Publications (1)

Publication Number	Publication Date
CH372300A true CH372300A (de)	1963-10-15

Family

ID=26641636

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6965959A CH372300A (de)	1958-02-25	1959-02-17	Verfahren zur Herstellung von 17-Estern des 19-Nortestosterons

Country Status (6)

Country	Link
BE (1)	BE576053A (fr)
CH (1)	CH372300A (fr)
ES (1)	ES246970A1 (fr)
FR (1)	FR361M (fr)
NL (1)	NL93032C (fr)
OA (1)	OA00922A (fr)

0
- NL NL93032D patent/NL93032C/xx active
1959
- 1959-01-31 ES ES0246970A patent/ES246970A1/es not_active Expired
- 1959-02-17 CH CH6965959A patent/CH372300A/de unknown
- 1959-02-24 BE BE576053A patent/BE576053A/nl unknown
1960
- 1960-08-29 FR FR837016A patent/FR361M/fr active Active
1964
- 1964-12-24 OA OA51017A patent/OA00922A/fr unknown

Also Published As

Publication number	Publication date
NL93032C (fr)
FR361M (fr)	1961-04-04
BE576053A (nl)	1959-08-24
ES246970A1 (es)	1959-10-01
OA00922A (fr)	1968-03-22

Publication	Publication Date	Title
DE69409969T2 (de)	1998-12-10	Salze der mehrfach ungesättigten fettsäuren und diese enthaltende pharmazeutischen zusammensetzungen
DE69431965T2 (de)	2003-04-30	Wirkstoff gegen fettsucht
DE3887151T2 (de)	1994-06-30	Inhibitoren für zellenzuwachs und methoden für krebsbehandlung.
DE2633210C2 (de)	1987-04-09	Verwendung von D-17&beta;-Acetoxy-13&beta;-äthyl-17&alpha;-äthinyl-gon-4-en-3-on-oxim zur Hemmung der Fertilität und Ovulation
CH625253A5 (fr)	1981-09-15
DE2818586C2 (fr)	1987-07-16
DE69307895T2 (de)	1997-08-14	Therapeutische verwendung von phosphoryl-l-serin-n-acyl-sphingosin
DE3000246C2 (de)	1989-02-02	Verfahren zur Herstellung von L-&alpha;-Glycerylphosphorylcholin
CH372300A (de)	1963-10-15	Verfahren zur Herstellung von 17-Estern des 19-Nortestosterons
DE2501091A1 (de)	1975-07-24	17-alpha-aethinyl-(5-alpha)-2-androsten-17-beta-ol und sein 17-beta-acetat, verfahren zu ihrer herstellung und ihre therapeutische verwendung
DE3028255C2 (de)	1985-12-19	9&alpha;,11&beta;-Dichlor-16&alpha;-methyl-21-oxycarbonyldicyclohexyl-methyloxypregan-1,4-dien-3,20-dion, Verfahren zu seiner Herstellung und dieses enthaltende pharmazeutische Zusammensetzungen
DE2553997A1 (de)	1976-08-12	Ester von 19-nor-testosteron
DE2100475C3 (de)	1973-11-22	21 Ester des Prednisolons und Dexamethasons mit S haltigen Amino sauren, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH645019A5 (de)	1984-09-14	Loesungsmittelgemisch und verfahren zur herstellung von parenteral verabreichbaren injektionsloesungen.
CH628067A5 (de)	1982-02-15	Verfahren zur herstellung neuer 21-acetale von steroid-21-aldehyden.
DE2323615A1 (de)	1973-11-22	Zootechnische zusammensetzungen
DE1087596B (de)	1960-08-25	Verfahren zur Herstellung eines 19-Nortestosteron-17-fettsaeureesters mit lang anhaltender anaboler Wirkung
DE1618224C3 (de)	1976-09-30	D-Homosteroide, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE1131666B (de)	1962-06-20	Verfahren zur Herstellung von Estern des 19-Nortestosterons
DE722109C (de)	1942-07-03	Verfahren zur Herstellung von haltbaren Lipoidemulsionen aus tierischen Organen, Sekreten oder Exkreten
AT208526B (de)	1960-04-11	Verfahren zur Herstellung von neuen Estern des Testosterons und 19-Nortestosterons
DE1468919C (de)	1971-04-29	3,11 Dioxo steroid 4,9 diene und ein Verfahren zu ihrer Herstellung
CH380119A (de)	1964-07-31	Verfahren zur Herstellung neuer Ester des 19-Nortestosterons
DE1815464C (de)	1972-09-14	3 Oxo-gonatnene sowie diese enthalten de pharmazeutische Zusammensetzungen
DE765906C (de)	1953-05-04	Verfahren zur Darstellung von Acylverbindungen der Androstanreihe