GB999398A - New esters of the yohimbane series and process for their manufacture - Google Patents
New esters of the yohimbane series and process for their manufactureInfo
- Publication number
- GB999398A GB999398A GB49912/64A GB4991264A GB999398A GB 999398 A GB999398 A GB 999398A GB 49912/64 A GB49912/64 A GB 49912/64A GB 4991264 A GB4991264 A GB 4991264A GB 999398 A GB999398 A GB 999398A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reserpate
- methoxyethyl
- halo
- nitro
- radical
- 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
- 150000002148 esters Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- JUPDIHMJFPDGMY-DEYYWGMASA-N yohimban Chemical class C1=CC=C2C(CCN3C[C@@H]4CCCC[C@H]4C[C@H]33)=C3NC2=C1 JUPDIHMJFPDGMY-DEYYWGMASA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- -1 nitro-benzenesulphonic acid halide Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- XAROELXRWZQTTG-UHFFFAOYSA-N 1-diazo-2-methoxyethane Chemical compound COCC=[N+]=[N-] XAROELXRWZQTTG-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 229940093475 2-ethoxyethanol Drugs 0.000 abstract 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- MDJQWFFIUHUJSB-UQVJXISSSA-N Methyl reserpate Chemical compound COC1=CC=C2C(CCN3C[C@H]4C[C@@H](O)[C@@H]([C@H]([C@H]4C[C@@H]33)C(=O)OC)OC)=C3NC2=C1 MDJQWFFIUHUJSB-UQVJXISSSA-N 0.000 abstract 1
- MDJQWFFIUHUJSB-MIESRMKVSA-N Methyl reserpate Natural products O=C(OC)[C@@H]1[C@@H](OC)[C@H](O)C[C@H]2[C@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 MDJQWFFIUHUJSB-MIESRMKVSA-N 0.000 abstract 1
- MDJQWFFIUHUJSB-UHFFFAOYSA-N Reserpinsaeure-methylester Natural products COC1=CC=C2C(CCN3CC4CC(O)C(C(C4CC33)C(=O)OC)OC)=C3NC2=C1 MDJQWFFIUHUJSB-UHFFFAOYSA-N 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- YPPVLWVYJSVLHI-UHFFFAOYSA-N ethyl n-(2-methoxyethyl)carbamate Chemical compound CCOC(=O)NCCOC YPPVLWVYJSVLHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- JVHNBFFHWQQPLL-WOXROFTLSA-N reserpic acid Chemical compound COC1=CC=C2C(CCN3C[C@H]4C[C@@H](O)[C@@H]([C@H]([C@H]4C[C@@H]33)C(O)=O)OC)=C3NC2=C1 JVHNBFFHWQQPLL-WOXROFTLSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4691160A | 1960-08-02 | 1960-08-02 | |
| US7349060A | 1960-12-05 | 1960-12-05 | |
| US11032061A | 1961-05-16 | 1961-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB999398A true GB999398A (en) | 1965-07-28 |
Family
ID=27367016
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46383/64A Expired GB999397A (en) | 1960-08-02 | 1961-08-02 | New esters of the vohimbane series and process for their manufacture |
| GB28119/61A Expired GB999393A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
| GB28118/61A Expired GB999392A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
| GB52687/64A Expired GB999399A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB49912/64A Expired GB999398A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
| GB28117/61A Expired GB999391A (en) | 1960-08-02 | 1961-08-02 | Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46383/64A Expired GB999397A (en) | 1960-08-02 | 1961-08-02 | New esters of the vohimbane series and process for their manufacture |
| GB28119/61A Expired GB999393A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
| GB28118/61A Expired GB999392A (en) | 1960-08-02 | 1961-08-02 | New ethers of the yohimbane series and process for their manufacture |
| GB52687/64A Expired GB999399A (en) | 1960-08-02 | 1961-08-02 | New esters of the yohimbane series and process for their manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28117/61A Expired GB999391A (en) | 1960-08-02 | 1961-08-02 | Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| AT (7) | AT252461B (enrdf_load_stackoverflow) |
| CH (8) | CH416658A (enrdf_load_stackoverflow) |
| ES (3) | ES269515A1 (enrdf_load_stackoverflow) |
| GB (6) | GB999397A (enrdf_load_stackoverflow) |
| NL (1) | NL139529B (enrdf_load_stackoverflow) |
| SE (7) | SE301650B (enrdf_load_stackoverflow) |
-
1961
- 1961-07-12 CH CH819261A patent/CH416658A/de unknown
- 1961-07-12 CH CH308665A patent/CH407145A/de unknown
- 1961-07-12 CH CH819161A patent/CH398628A/de unknown
- 1961-07-12 CH CH308465A patent/CH407143A/de unknown
- 1961-07-12 CH CH819061A patent/CH398627A/de unknown
- 1961-07-12 CH CH308765A patent/CH407146A/de unknown
- 1961-07-12 CH CH308565A patent/CH407144A/de unknown
- 1961-07-12 CH CH819361A patent/CH410969A/de unknown
- 1961-08-01 AT AT100262A patent/AT252461B/de active
- 1961-08-01 AT AT100062A patent/AT252459B/de active
- 1961-08-01 AT AT887662A patent/AT252463B/de active
- 1961-08-01 AT AT100362A patent/AT252462B/de active
- 1961-08-01 AT AT100162A patent/AT252460B/de active
- 1961-08-01 AT AT594961A patent/AT249274B/de active
- 1961-08-01 AT AT594861A patent/AT249273B/de active
- 1961-08-01 NL NL61267779A patent/NL139529B/xx unknown
- 1961-08-02 ES ES0269515A patent/ES269515A1/es not_active Expired
- 1961-08-02 ES ES0269514A patent/ES269514A1/es not_active Expired
- 1961-08-02 ES ES0269516A patent/ES269516A1/es not_active Expired
- 1961-08-02 SE SE7893/61A patent/SE301650B/xx unknown
- 1961-08-02 GB GB46383/64A patent/GB999397A/en not_active Expired
- 1961-08-02 GB GB28119/61A patent/GB999393A/en not_active Expired
- 1961-08-02 SE SE7892/61A patent/SE301478B/xx unknown
- 1961-08-02 GB GB28118/61A patent/GB999392A/en not_active Expired
- 1961-08-02 GB GB52687/64A patent/GB999399A/en not_active Expired
- 1961-08-02 GB GB49912/64A patent/GB999398A/en not_active Expired
- 1961-08-02 GB GB28117/61A patent/GB999391A/en not_active Expired
-
1965
- 1965-06-08 SE SE7478/65A patent/SE301321B/xx unknown
- 1965-06-08 SE SE7482/65A patent/SE301487B/xx unknown
- 1965-06-08 SE SE7481/65A patent/SE301486B/xx unknown
- 1965-06-08 SE SE7479/65A patent/SE301484B/xx unknown
- 1965-06-08 SE SE7480/65A patent/SE301485B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES269515A1 (es) | 1962-04-16 |
| GB999393A (en) | 1965-07-28 |
| SE301487B (enrdf_load_stackoverflow) | 1968-06-10 |
| NL139529B (nl) | 1973-08-15 |
| CH410969A (de) | 1966-04-15 |
| ES269514A1 (es) | 1962-04-16 |
| SE301478B (enrdf_load_stackoverflow) | 1968-06-10 |
| CH407144A (de) | 1966-02-15 |
| CH407145A (de) | 1966-02-15 |
| AT252463B (de) | 1967-02-27 |
| AT252462B (de) | 1967-02-27 |
| CH407143A (de) | 1966-02-15 |
| CH398628A (de) | 1966-03-15 |
| GB999397A (en) | 1965-07-28 |
| SE301321B (enrdf_load_stackoverflow) | 1968-06-04 |
| CH407146A (de) | 1966-02-15 |
| AT252460B (de) | 1967-02-27 |
| SE301486B (enrdf_load_stackoverflow) | 1968-06-10 |
| AT249274B (de) | 1966-09-12 |
| GB999392A (en) | 1965-07-28 |
| AT249273B (de) | 1966-09-12 |
| SE301484B (enrdf_load_stackoverflow) | 1968-06-10 |
| CH398627A (de) | 1966-03-15 |
| AT252461B (de) | 1967-02-27 |
| AT252459B (de) | 1967-02-27 |
| SE301485B (enrdf_load_stackoverflow) | 1968-06-10 |
| GB999391A (en) | 1965-07-28 |
| CH416658A (de) | 1966-07-15 |
| SE301650B (enrdf_load_stackoverflow) | 1968-06-17 |
| ES269516A1 (es) | 1962-04-16 |
| GB999399A (en) | 1965-07-28 |
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