CA1044224A - Ester of 19-nor-testosterone - Google Patents
Ester of 19-nor-testosteroneInfo
- Publication number
- CA1044224A CA1044224A CA240,847A CA240847A CA1044224A CA 1044224 A CA1044224 A CA 1044224A CA 240847 A CA240847 A CA 240847A CA 1044224 A CA1044224 A CA 1044224A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- process according
- beta
- novel
- estren
- 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.)
- Expired
Links
- 229960004719 nandrolone Drugs 0.000 title abstract description 13
- 150000002148 esters Chemical class 0.000 title abstract description 12
- 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 abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 abstract description 16
- 239000003263 anabolic agent Substances 0.000 abstract description 6
- 229940124325 anabolic agent Drugs 0.000 abstract description 5
- 230000001195 anabolic effect Effects 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000001548 androgenic effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229960001133 nandrolone phenpropionate Drugs 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- UBWXUGDQUBIEIZ-QNTYDACNSA-N nandrolone phenpropionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@H]4CCC(=O)C=C4CC3)CC[C@@]21C)C(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-QNTYDACNSA-N 0.000 description 5
- 241000220438 Arachis Species 0.000 description 4
- 235000003911 Arachis Nutrition 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 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 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940070021 anabolic steroids Drugs 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- -1 ester nandrolone-phenylpropionate Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 210000001625 seminal vesicle Anatomy 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 201000010653 vesiculitis Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 description 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 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 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
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0074—Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7415669A NL7415669A (nl) | 1974-12-02 | 1974-12-02 | Werkwijze ter bereiding van een nieuwe ester van 19-nor-testosteron. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044224A true CA1044224A (en) | 1978-12-12 |
Family
ID=19822576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA240,847A Expired CA1044224A (en) | 1974-12-02 | 1975-12-01 | Ester of 19-nor-testosterone |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4002747A (en, 2012) |
| JP (1) | JPS5182252A (en, 2012) |
| AU (1) | AU500934B2 (en, 2012) |
| BE (1) | BE836151A (en, 2012) |
| CA (1) | CA1044224A (en, 2012) |
| CH (1) | CH616689A5 (en, 2012) |
| DE (1) | DE2553997A1 (en, 2012) |
| DK (1) | DK135456B (en, 2012) |
| ES (1) | ES443115A1 (en, 2012) |
| FI (1) | FI54129C (en, 2012) |
| FR (1) | FR2293210A1 (en, 2012) |
| GB (1) | GB1534147A (en, 2012) |
| HU (1) | HU170931B (en, 2012) |
| IE (1) | IE42139B1 (en, 2012) |
| LU (1) | LU73894A1 (en, 2012) |
| NL (1) | NL7415669A (en, 2012) |
| SE (1) | SE404529B (en, 2012) |
| ZA (1) | ZA757352B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2111092T3 (es) * | 1992-06-12 | 1998-03-01 | Hoechst Ag | Derivados de acidos biliares, procedimiento para su preparacion y utilizacion de estos compuestos como medicamentos. |
| EP1709061A1 (en) * | 2004-01-15 | 2006-10-11 | Warner Chilcott Company Inc. | Di-steroidal prodrugs of ethinyl estradiol |
| MXPA06007852A (es) * | 2004-01-15 | 2007-01-31 | Warner Chilcott Co Inc | Profarmacos di-esteroidales de estradiol. |
| CA2610481A1 (en) * | 2005-07-12 | 2007-01-18 | Warner Chilcott Company, Inc. | 3-ester prodrugs of estradiol |
| MX2008000416A (es) * | 2005-07-12 | 2008-03-10 | Warner Chilcott Co Inc | Profarmacos de 3-ester de etinil estradiol. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL147740B (nl) * | 1965-10-28 | 1975-11-17 | Organon Nv | Werkwijze ter bereiding van dicarbonzuuresters van 19-nor-testosteron met verlengde anabole werking, alsmede gevormd farmaceutisch preparaat. |
-
1974
- 1974-12-02 NL NL7415669A patent/NL7415669A/xx not_active Application Discontinuation
-
1975
- 1975-11-24 US US05/634,391 patent/US4002747A/en not_active Expired - Lifetime
- 1975-11-24 IE IE2547/75A patent/IE42139B1/en unknown
- 1975-11-24 ZA ZA757352A patent/ZA757352B/xx unknown
- 1975-11-26 AU AU86965/75A patent/AU500934B2/en not_active Expired
- 1975-11-26 CH CH1534275A patent/CH616689A5/de not_active IP Right Cessation
- 1975-11-26 GB GB48639/75A patent/GB1534147A/en not_active Expired
- 1975-11-28 FI FI753372A patent/FI54129C/fi not_active IP Right Cessation
- 1975-11-28 JP JP50143281A patent/JPS5182252A/ja active Pending
- 1975-11-28 LU LU73894A patent/LU73894A1/xx unknown
- 1975-12-01 FR FR7536719A patent/FR2293210A1/fr active Granted
- 1975-12-01 CA CA240,847A patent/CA1044224A/en not_active Expired
- 1975-12-01 ES ES443115A patent/ES443115A1/es not_active Expired
- 1975-12-01 DE DE19752553997 patent/DE2553997A1/de not_active Withdrawn
- 1975-12-01 SE SE7513497A patent/SE404529B/xx unknown
- 1975-12-01 DK DK540675AA patent/DK135456B/da unknown
- 1975-12-01 BE BE162338A patent/BE836151A/xx unknown
- 1975-12-02 HU HU75AO00000430A patent/HU170931B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8696575A (en) | 1977-06-02 |
| IE42139L (en) | 1976-06-02 |
| FR2293210A1 (fr) | 1976-07-02 |
| DK135456C (en, 2012) | 1977-09-26 |
| FI54129C (fi) | 1978-10-10 |
| US4002747A (en) | 1977-01-11 |
| ES443115A1 (es) | 1977-08-16 |
| FI54129B (fi) | 1978-06-30 |
| SE7513497L (sv) | 1976-06-03 |
| NL7415669A (nl) | 1976-06-04 |
| DE2553997A1 (de) | 1976-08-12 |
| SE404529B (sv) | 1978-10-09 |
| IE42139B1 (en) | 1980-06-04 |
| FR2293210B1 (en, 2012) | 1979-09-21 |
| BE836151A (fr) | 1976-06-01 |
| AU500934B2 (en) | 1979-06-07 |
| JPS5182252A (en) | 1976-07-19 |
| HU170931B (hu) | 1977-10-28 |
| DK540675A (en, 2012) | 1976-06-03 |
| FI753372A7 (en, 2012) | 1976-06-03 |
| DK135456B (da) | 1977-05-02 |
| GB1534147A (en) | 1978-11-29 |
| ZA757352B (en) | 1976-11-24 |
| CH616689A5 (en, 2012) | 1980-04-15 |
| LU73894A1 (en, 2012) | 1976-07-01 |
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