NO130461B - - Google Patents
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- Publication number
- NO130461B NO130461B NO00170746A NO17074667A NO130461B NO 130461 B NO130461 B NO 130461B NO 00170746 A NO00170746 A NO 00170746A NO 17074667 A NO17074667 A NO 17074667A NO 130461 B NO130461 B NO 130461B
- Authority
- NO
- Norway
- Prior art keywords
- testosterone
- esters
- solution
- propionate
- ethyl acetate
- Prior art date
Links
- 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 38
- 229960003604 testosterone Drugs 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 11
- 229960004719 nandrolone Drugs 0.000 claims description 8
- 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 8
- 230000001548 androgenic effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 230000001195 anabolic effect Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 19
- 230000000694 effects Effects 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 210000001625 seminal vesicle Anatomy 0.000 description 9
- 201000010653 vesiculitis Diseases 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 210000002307 prostate Anatomy 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- -1 pyridine Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 description 2
- 229960003484 testosterone enanthate Drugs 0.000 description 2
- 150000003515 testosterones Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41F—PRINTING MACHINES OR PRESSES
- B41F15/00—Screen printers
- B41F15/08—Machines
- B41F15/0886—Machines for printing on conical or frusto-conical surfaces
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41F—PRINTING MACHINES OR PRESSES
- B41F15/00—Screen printers
- B41F15/08—Machines
- B41F15/0872—Machines for printing on articles having essentially cylindrical surfaces
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41F—PRINTING MACHINES OR PRESSES
- B41F17/00—Printing apparatus or machines of special types or for particular purposes, not otherwise provided for
- B41F17/28—Printing apparatus or machines of special types or for particular purposes, not otherwise provided for for printing on curved surfaces of conical or frusto-conical articles
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Screen Printers (AREA)
- Printing Methods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR85541A FR1513389A (fr) | 1966-11-30 | 1966-11-30 | Machine à décorer en plusieurs couleurs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130461B true NO130461B (xx) | 1974-09-09 |
| NO130461C NO130461C (xx) | 1974-12-18 |
Family
ID=8621770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO170746A NO130461C (xx) | 1966-11-30 | 1967-11-29 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3521298A (xx) |
| JP (1) | JPS4929688B1 (xx) |
| BE (1) | BE706741A (xx) |
| CH (1) | CH479398A (xx) |
| CS (1) | CS156413B2 (xx) |
| DE (1) | DE1611319A1 (xx) |
| DK (1) | DK124594B (xx) |
| ES (1) | ES347699A1 (xx) |
| FR (1) | FR1513389A (xx) |
| GB (1) | GB1212845A (xx) |
| LU (1) | LU54833A1 (xx) |
| MC (1) | MC687A1 (xx) |
| NL (1) | NL150050B (xx) |
| NO (1) | NO130461C (xx) |
| SE (1) | SE342578B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3672296A (en) * | 1968-06-11 | 1972-06-27 | Wilfried Kammann | Screen printing machine for printing cylindrical and conical articles |
| US3792657A (en) * | 1969-06-26 | 1974-02-19 | W Kammann | Screen printing machine for cylindrical or conical bodies |
| IT989517B (it) * | 1971-12-10 | 1975-06-10 | Produ Ag | Macchina per la stampa a rete |
| US4109573A (en) * | 1974-01-22 | 1978-08-29 | Werner Kamman Maschinenfabrik | Article, screen and squeegee drive for screenprinter |
| US3933091A (en) * | 1974-06-17 | 1976-01-20 | New Products Corporation | Apparatus for screen printing bottles |
| JPS5640554A (en) * | 1979-09-10 | 1981-04-16 | Yakult Honsha Co Ltd | Continuous type multicolor printing press |
| JPS56120350A (en) * | 1980-02-28 | 1981-09-21 | Yakult Honsha Co Ltd | Continuous multicolor printer for tapered section circular body |
| US4479429A (en) * | 1982-03-22 | 1984-10-30 | Yoshino America Corporation | Multi-color printing apparatus of surfaces of bodies of rotation |
| DE4023135A1 (de) * | 1990-07-20 | 1992-01-23 | Alt Peter | Verfahren und vorrichtung zum beschichten von motorkolben |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3273618A (en) * | 1966-09-20 | Flodin asparagus trimmer | ||
| US2066351A (en) * | 1934-01-23 | 1937-01-05 | Johnson Alfred | Striping or banding machine |
| US2121491A (en) * | 1934-02-14 | 1938-06-21 | Owens Illinois Glass Co | Machine for decorating surfaces by stencil method |
| US2132818A (en) * | 1936-06-18 | 1938-10-11 | Owens Illinois Glass Co | Method of and apparatus for decorating bottles and like articles |
| US2198565A (en) * | 1938-03-31 | 1940-04-23 | Libbey Glass Co | Tumbler decorating apparatus |
| US2183223A (en) * | 1938-04-30 | 1939-12-12 | Owens Illinois Glass Co | Stenciling apparatus |
| US2757606A (en) * | 1951-01-02 | 1956-08-07 | Dubuit Louis Gilbert | Silk-screen printing machines |
| US2739531A (en) * | 1951-08-29 | 1956-03-27 | Hagerman Lawrence | Decorating machine |
| US2920556A (en) * | 1956-11-21 | 1960-01-12 | Owens Illinois Glass Co | Machine for decorating round surfaces |
| US2975705A (en) * | 1958-02-12 | 1961-03-21 | Gilman Louis | Silk screen process press |
| US3113510A (en) * | 1961-12-18 | 1963-12-10 | Dubuit Louis Gilbert | Silk-screen printing device |
| US3195451A (en) * | 1962-09-11 | 1965-07-20 | Kamru Products Corp | Decorating means |
| US3172357A (en) * | 1963-03-04 | 1965-03-09 | Strutz & Co Inc Carl | Pneumatically operated stenciling apparatus |
| US3263603A (en) * | 1964-01-03 | 1966-08-02 | M & M Res Engineering Co | Silk screen printing apparatus |
| US3253538A (en) * | 1964-07-13 | 1966-05-31 | Strutz & Co Inc Carl | Bottle decorating apparatus |
-
1966
- 1966-11-30 FR FR85541A patent/FR1513389A/fr not_active Expired
-
1967
- 1967-11-07 MC MC725A patent/MC687A1/xx unknown
- 1967-11-08 SE SE15285/67A patent/SE342578B/xx unknown
- 1967-11-09 LU LU54833D patent/LU54833A1/xx unknown
- 1967-11-14 DE DE19671611319 patent/DE1611319A1/de active Pending
- 1967-11-16 CH CH1605067A patent/CH479398A/fr not_active IP Right Cessation
- 1967-11-18 ES ES347699A patent/ES347699A1/es not_active Expired
- 1967-11-20 BE BE706741D patent/BE706741A/xx not_active IP Right Cessation
- 1967-11-21 US US684786A patent/US3521298A/en not_active Expired - Lifetime
- 1967-11-21 GB GB53011/67A patent/GB1212845A/en not_active Expired
- 1967-11-29 NO NO170746A patent/NO130461C/no unknown
- 1967-11-29 CS CS844567A patent/CS156413B2/cs unknown
- 1967-11-29 DK DK597867AA patent/DK124594B/da not_active IP Right Cessation
- 1967-11-30 JP JP42076528A patent/JPS4929688B1/ja active Pending
- 1967-11-30 NL NL676716292A patent/NL150050B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR1513389A (fr) | 1968-02-16 |
| NL150050B (nl) | 1976-07-15 |
| DE1611319A1 (de) | 1971-05-19 |
| NL6716292A (xx) | 1968-05-31 |
| ES347699A1 (es) | 1969-02-16 |
| MC687A1 (fr) | 1968-09-03 |
| NO130461C (xx) | 1974-12-18 |
| LU54833A1 (xx) | 1968-02-02 |
| SE342578B (xx) | 1972-02-14 |
| JPS4929688B1 (xx) | 1974-08-06 |
| CS156413B2 (xx) | 1974-07-24 |
| CH479398A (fr) | 1969-10-15 |
| DK124594B (da) | 1972-11-06 |
| BE706741A (xx) | 1968-04-01 |
| GB1212845A (en) | 1970-11-18 |
| US3521298A (en) | 1970-07-21 |
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