NO127004B - - Google Patents
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- Publication number
- NO127004B NO127004B NO405670A NO405670A NO127004B NO 127004 B NO127004 B NO 127004B NO 405670 A NO405670 A NO 405670A NO 405670 A NO405670 A NO 405670A NO 127004 B NO127004 B NO 127004B
- Authority
- NO
- Norway
- Prior art keywords
- trans
- cis
- isomer
- naphthalene
- disulfonic acid
- Prior art date
Links
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- -1 trans isomer compound Chemical class 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72768968A | 1968-05-08 | 1968-05-08 | |
| DE1768704 | 1968-06-21 | ||
| DE1768895A DE1768895C2 (de) | 1968-07-11 | 1968-07-11 | Verfahren zur Herstellung von 3-trans-Dimethylamino-4-phenyl-4-trans-carbaethoxycyclohexen-(1) neben 3-cis-Dimethylamino-4-phenyl-4-cis-carbaethoxy-cyclohexen-(1) |
| US77719768A | 1968-11-19 | 1968-11-19 | |
| US77720268A | 1968-11-19 | 1968-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127004B true NO127004B (enrdf_load_html_response) | 1973-04-24 |
Family
ID=27509964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO405670A NO127004B (enrdf_load_html_response) | 1968-05-08 | 1970-10-26 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5011907B1 (enrdf_load_html_response) |
| BE (1) | BE732713A (enrdf_load_html_response) |
| CA (1) | CA935160A (enrdf_load_html_response) |
| FR (1) | FR2008082B1 (enrdf_load_html_response) |
| GB (1) | GB1216152A (enrdf_load_html_response) |
| NL (1) | NL6907094A (enrdf_load_html_response) |
| NO (1) | NO127004B (enrdf_load_html_response) |
| SE (1) | SE360070B (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2129882A1 (en) * | 1971-03-18 | 1972-11-03 | Warner Lambert Co | 3r-n-monomethylamino-4c-phenyl-4t-ethoxy-car - analgesic antipy |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1518959B1 (de) * | 1965-11-19 | 1970-03-26 | Goedecke Ag | Verfahren zur Herstellung von basisch substituierten Cyclohexenen |
-
1969
- 1969-05-06 GB GB2316669A patent/GB1216152A/en not_active Expired
- 1969-05-08 FR FR6914768A patent/FR2008082B1/fr not_active Expired
- 1969-05-08 SE SE655269A patent/SE360070B/xx unknown
- 1969-05-08 NL NL6907094A patent/NL6907094A/xx not_active Application Discontinuation
- 1969-05-08 JP JP3546369A patent/JPS5011907B1/ja active Pending
- 1969-05-08 BE BE732713A patent/BE732713A/xx unknown
-
1970
- 1970-06-30 CA CA087006A patent/CA935160A/en not_active Expired
- 1970-10-26 NO NO405670A patent/NO127004B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE360070B (enrdf_load_html_response) | 1973-09-17 |
| NL6907094A (enrdf_load_html_response) | 1969-11-11 |
| BE732713A (enrdf_load_html_response) | 1969-11-10 |
| JPS5011907B1 (enrdf_load_html_response) | 1975-05-07 |
| FR2008082B1 (enrdf_load_html_response) | 1973-06-08 |
| FR2008082A1 (enrdf_load_html_response) | 1970-01-16 |
| CA935160A (en) | 1973-10-09 |
| GB1216152A (en) | 1970-12-16 |
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