CH616689A5 - - Google Patents
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- Publication number
- CH616689A5 CH616689A5 CH1534275A CH1534275A CH616689A5 CH 616689 A5 CH616689 A5 CH 616689A5 CH 1534275 A CH1534275 A CH 1534275A CH 1534275 A CH1534275 A CH 1534275A CH 616689 A5 CH616689 A5 CH 616689A5
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- quaternary phosphonium
- phosphonium halides
- reaction
- halides
- Prior art date
Links
- -1 phosphonium halides Chemical class 0.000 claims description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003003 phosphines Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 14
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000243 solution Substances 0.000 description 19
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 16
- NJFUXFRJVIXVSG-UHFFFAOYSA-M tetramethylphosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)C NJFUXFRJVIXVSG-UHFFFAOYSA-M 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000011144 upstream manufacturing 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
- 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 |
|---|---|
| CH616689A5 true CH616689A5 (is") | 1980-04-15 |
Family
ID=19822576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1534275A CH616689A5 (is") | 1974-12-02 | 1975-11-26 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4002747A (is") |
| JP (1) | JPS5182252A (is") |
| AU (1) | AU500934B2 (is") |
| BE (1) | BE836151A (is") |
| CA (1) | CA1044224A (is") |
| CH (1) | CH616689A5 (is") |
| DE (1) | DE2553997A1 (is") |
| DK (1) | DK135456B (is") |
| ES (1) | ES443115A1 (is") |
| FI (1) | FI54129C (is") |
| FR (1) | FR2293210A1 (is") |
| GB (1) | GB1534147A (is") |
| HU (1) | HU170931B (is") |
| IE (1) | IE42139B1 (is") |
| LU (1) | LU73894A1 (is") |
| NL (1) | NL7415669A (is") |
| SE (1) | SE404529B (is") |
| ZA (1) | ZA757352B (is") |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0573848T3 (da) * | 1992-06-12 | 1998-08-10 | Hoechst Ag | Galdesyrederivater, fremgangsmåde til deres fremstilling og anvendelse af disse forbindelser som lægemidler |
| CA2553815A1 (en) * | 2004-01-15 | 2005-08-04 | Warner Chilcott Company, Inc. | Di-steroidal prodrugs of estradiol |
| WO2005070950A1 (en) * | 2004-01-15 | 2005-08-04 | Warner Chilcott Company, Inc. | Di-steroidal prodrugs of ethinyl estradiol |
| CA2610481A1 (en) * | 2005-07-12 | 2007-01-18 | Warner Chilcott Company, Inc. | 3-ester prodrugs of estradiol |
| WO2007024338A2 (en) * | 2005-07-12 | 2007-03-01 | Warner Chilcott Company, Inc. | 3 -ester prodrugs of ethynylestradiol |
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 GB GB48639/75A patent/GB1534147A/en not_active Expired
- 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
- 1975-11-28 FI FI753372A patent/FI54129C/fi not_active IP Right Cessation
- 1975-11-28 LU LU73894A patent/LU73894A1/xx unknown
- 1975-11-28 JP JP50143281A patent/JPS5182252A/ja active Pending
- 1975-12-01 FR FR7536719A patent/FR2293210A1/fr active Granted
- 1975-12-01 ES ES443115A patent/ES443115A1/es not_active Expired
- 1975-12-01 CA CA240,847A patent/CA1044224A/en not_active Expired
- 1975-12-01 BE BE162338A patent/BE836151A/xx unknown
- 1975-12-01 DK DK540675AA patent/DK135456B/da unknown
- 1975-12-01 SE SE7513497A patent/SE404529B/xx unknown
- 1975-12-01 DE DE19752553997 patent/DE2553997A1/de not_active Withdrawn
- 1975-12-02 HU HU75AO00000430A patent/HU170931B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE836151A (fr) | 1976-06-01 |
| HU170931B (hu) | 1977-10-28 |
| AU500934B2 (en) | 1979-06-07 |
| FI753372A7 (is") | 1976-06-03 |
| JPS5182252A (en) | 1976-07-19 |
| NL7415669A (nl) | 1976-06-04 |
| FR2293210A1 (fr) | 1976-07-02 |
| ZA757352B (en) | 1976-11-24 |
| DE2553997A1 (de) | 1976-08-12 |
| GB1534147A (en) | 1978-11-29 |
| FR2293210B1 (is") | 1979-09-21 |
| SE404529B (sv) | 1978-10-09 |
| AU8696575A (en) | 1977-06-02 |
| DK540675A (is") | 1976-06-03 |
| FI54129B (fi) | 1978-06-30 |
| CA1044224A (en) | 1978-12-12 |
| DK135456B (da) | 1977-05-02 |
| FI54129C (fi) | 1978-10-10 |
| IE42139B1 (en) | 1980-06-04 |
| LU73894A1 (is") | 1976-07-01 |
| SE7513497L (sv) | 1976-06-03 |
| DK135456C (is") | 1977-09-26 |
| US4002747A (en) | 1977-01-11 |
| IE42139L (en) | 1976-06-02 |
| ES443115A1 (es) | 1977-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |