CH616688A5 - - Google Patents
Download PDFInfo
- Publication number
- CH616688A5 CH616688A5 CH1459975A CH1459975A CH616688A5 CH 616688 A5 CH616688 A5 CH 616688A5 CH 1459975 A CH1459975 A CH 1459975A CH 1459975 A CH1459975 A CH 1459975A CH 616688 A5 CH616688 A5 CH 616688A5
- Authority
- CH
- Switzerland
- Prior art keywords
- nandrolone
- anabolic
- new
- ester
- testosterone
- Prior art date
Links
- 229960004719 nandrolone Drugs 0.000 claims 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 claims description 11
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- -1 19-nor-testosterone ester Chemical class 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 description 13
- 230000001195 anabolic effect Effects 0.000 description 11
- 229960001133 nandrolone phenpropionate Drugs 0.000 description 11
- 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 10
- 150000002148 esters Chemical class 0.000 description 9
- 230000001548 androgenic effect Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003263 anabolic agent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940124325 anabolic agent Drugs 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
- 230000000694 effects Effects 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
- 210000002307 prostate Anatomy 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 210000001625 seminal vesicle Anatomy 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 201000010653 vesiculitis Diseases 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 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
- 239000000312 peanut oil Substances 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-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
- 241001465754 Metazoa Species 0.000 description 1
- 229940070021 anabolic steroids Drugs 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 229960002903 benzyl benzoate 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 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
- 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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 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
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742457442 DE2457442C2 (de) | 1974-12-05 | 1974-12-05 | Verfahren zur Herstellung von Tetramethylphosphoniumchlorid oder -bromid |
| DE19752511933 DE2511933A1 (de) | 1975-03-19 | 1975-03-19 | Verfahren zur herstellung von trialkylphosphinoxiden |
| DE19752522021 DE2522021A1 (de) | 1975-05-17 | 1975-05-17 | Verfahren zur herstellung von trialkylphosphinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616688A5 true CH616688A5 (US20100223739A1-20100909-C00005.png) | 1980-04-15 |
Family
ID=27186182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1459975A CH616688A5 (US20100223739A1-20100909-C00005.png) | 1974-12-05 | 1975-11-11 |
Country Status (8)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387250A (en) * | 1980-01-16 | 1983-06-07 | Firmenich Sa | Phosphonium salts, process for their preparation and use of same as starting materials for preparing unsaturated bicyclic compounds |
| US4429161A (en) * | 1981-08-17 | 1984-01-31 | Union Carbide Corporation | Process for preparing organic tertiary polyphosphine monooxides |
| JPS63119491A (ja) * | 1986-11-07 | 1988-05-24 | Nippon Chem Ind Co Ltd:The | 第四級ホスホニウムクロライドの製造方法 |
| JPH0285426U (US20100223739A1-20100909-C00005.png) * | 1988-12-20 | 1990-07-04 | ||
| JP3467307B2 (ja) * | 1994-03-31 | 2003-11-17 | 信越化学工業株式会社 | ホスホニウム塩の製造方法 |
| US5600017A (en) * | 1995-01-18 | 1997-02-04 | Exxon Research And Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide hydrogen ethylene and acetylene-(LAW072) |
| US5675041A (en) * | 1995-01-18 | 1997-10-07 | Exxon Research & Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene |
| US5973174A (en) * | 1998-11-24 | 1999-10-26 | Shell Oil Company | Preparation of transition metal catalysts from phosphonium salts |
| DE10129403A1 (de) * | 2001-06-19 | 2003-01-02 | Basf Ag | Verfahren zur Reinigung von Phosphoniumsalzen |
| WO2003066548A2 (en) * | 2002-02-06 | 2003-08-14 | Iowa State University Research Foundation, Inc. | Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins |
| US9365596B2 (en) * | 2013-12-13 | 2016-06-14 | Microvast Power Systems Co., Ltd. | Method for preparing quaternary phosphonium salts |
| CN105330695A (zh) * | 2015-12-08 | 2016-02-17 | 山东维天精细化工科技有限公司 | 一种四甲基氯化磷的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564200A (US20100223739A1-20100909-C00005.png) * | 1957-01-23 | |||
| US3389183A (en) * | 1965-06-07 | 1968-06-18 | Procter & Gamble | Process for the preparation of tertiary phosphines |
| US3316293A (en) * | 1965-07-26 | 1967-04-25 | Hooker Chemical Corp | Organic phosphorus compounds |
| DE2116355C3 (de) * | 1971-04-03 | 1979-05-31 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Trialkylphosphoniumhalogeniden |
| DE2116439B2 (de) * | 1971-04-03 | 1979-05-31 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Trialkylphosphinen |
| DE2407461C2 (de) * | 1974-02-16 | 1983-03-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Alkylphosphinen |
-
1975
- 1975-11-11 CH CH1459975A patent/CH616688A5/de not_active IP Right Cessation
- 1975-11-14 GB GB47053/75A patent/GB1497449A/en not_active Expired
- 1975-11-28 US US05/635,587 patent/US4122123A/en not_active Expired - Lifetime
- 1975-12-02 JP JP50143803A patent/JPS5912120B2/ja not_active Expired
- 1975-12-02 NL NL7514041A patent/NL7514041A/xx not_active Application Discontinuation
- 1975-12-02 DD DD189819A patent/DD123345A5/xx unknown
- 1975-12-03 IT IT52507/75A patent/IT1052487B/it active
- 1975-12-05 FR FR7537338A patent/FR2293436A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4122123A (en) | 1978-10-24 |
| JPS5912120B2 (ja) | 1984-03-21 |
| GB1497449A (en) | 1978-01-12 |
| DD123345A5 (US20100223739A1-20100909-C00005.png) | 1976-12-12 |
| IT1052487B (it) | 1981-06-20 |
| JPS5182227A (en) | 1976-07-19 |
| FR2293436B1 (US20100223739A1-20100909-C00005.png) | 1979-08-10 |
| NL7514041A (nl) | 1976-06-09 |
| FR2293436A1 (fr) | 1976-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH616688A5 (US20100223739A1-20100909-C00005.png) | ||
| DE2643936A1 (de) | Arzneimittel mit erythropoietischer wirksamkeit | |
| DE3613649A1 (de) | Substituierte oximether, ihre verwendung als bioregulatoren zur senkung des endzogenen ethylenspiegels in pflanzen | |
| EP0004898A1 (de) | Feste stabile pharmazeutische Zusammensetzung auf Basis von einem 1,3-Diester des 17-alpha-Ethinyl-7-alpha-methyl-1,3,5(10)-östratrien-1,3,17-beta-triols | |
| DE2553997A1 (de) | Ester von 19-nor-testosteron | |
| CH621560A5 (en) | Process for the preparation of 3-ketosteroids disubstituted in position 16 | |
| DE2601367C3 (de) | Steroid [(1-Benzyl-1H-indazol-3-yl)-oxy]-essigsäure und Verfahren zu ihrer Herstellung | |
| DE1593184C (de) | 19-Nortesteron-Diester von Dicarbonsäuren und Verfahren zu deren Herstellung | |
| DE2807407A1 (de) | Testosteronester | |
| DE1593184C3 (US20100223739A1-20100909-C00005.png) | ||
| CH637401A5 (de) | Acylderivate der 2-(3-(2-chloraethyl)-3-nitrosoureido)-2-desoxy-d-glucopyranose. | |
| AT201784B (de) | Verfahren zur Herstellung einer Verbindung der Cyclopentanopolyhydrophenanthrenreihe | |
| AT208526B (de) | Verfahren zur Herstellung von neuen Estern des Testosterons und 19-Nortestosterons | |
| DE2238304A1 (de) | Choleretisch wirksame ester bzw. salze von gallensaeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| AT216687B (de) | Verfahren zur Herstellung von Testosteronderivaten | |
| CH493507A (de) | Verfahren zur Herstellung von 1B-Methyl-2,3a-methylen-steroiden | |
| DE1593184B2 (de) | 19-nortesteron-diester von dicarbonsaeuren und verfahren zu deren herstellung | |
| DE1804392A1 (de) | 9-0-Kalamycinderivate und Verfahren zu ihrer Herstellung | |
| DE1188583B (de) | Verfahren zur Herstellung der Steroisomeren und des Racemats von Butan-1, 2, 3, 4-tetrol-1, 4-di-(methansulfonat) | |
| DE1445969C (de) | Verfahren zur Herstellung von basischen 3,4,5 Trimethoxybenzoesaureestern | |
| EP0196270A2 (de) | Wässrige Kristallsuspension von Steroidglykoestern | |
| DE1618980C3 (de) | In 17-Stellung substituierte 11, 13beta-Dialkylgon-4-en-3,17beta-diole und deren Ester | |
| DE977519C (de) | Verfahren zur Herstellung von 1-Phenyl-2-dihalogenacetamino-1, 3-propandiolen | |
| DE1081889B (de) | Verfahren zur Herstellung von neuen Estern des Testosterons und 19-Nortestosterons | |
| DE1250674B (US20100223739A1-20100909-C00005.png) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |