BE672578A - - Google Patents
Info
- Publication number
- BE672578A BE672578A BE672578DA BE672578A BE 672578 A BE672578 A BE 672578A BE 672578D A BE672578D A BE 672578DA BE 672578 A BE672578 A BE 672578A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- radical
- bornyl
- substituted
- fenchyl
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- DTIMOGKVZZGBPT-UHFFFAOYSA-N (2-oxohydrazinyl)urea Chemical compound NC(=O)NNN=O DTIMOGKVZZGBPT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 4
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- 230000009935 nitrosation Effects 0.000 claims description 3
- 238000007034 nitrosation reaction Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002723 alicyclic group Chemical group 0.000 claims 2
- 238000007710 freezing Methods 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 241000282472 Canis lupus familiaris Species 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 230000036772 blood pressure Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 241000289427 Didelphidae Species 0.000 description 6
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- 230000001077 hypotensive effect Effects 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930006735 fenchone Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- -1 p-methylbenzyl Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6514707A NL6514707A (enrdf_load_stackoverflow) | 1965-11-12 | 1965-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE672578A true BE672578A (enrdf_load_stackoverflow) |
Family
ID=19794632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE672578D BE672578A (enrdf_load_stackoverflow) | 1965-11-12 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE672578A (enrdf_load_stackoverflow) |
| NL (1) | NL6514707A (enrdf_load_stackoverflow) |
-
0
- BE BE672578D patent/BE672578A/fr unknown
-
1965
- 1965-11-12 NL NL6514707A patent/NL6514707A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6514707A (enrdf_load_stackoverflow) | 1967-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0442820B1 (fr) | Nouveaux dérivés de benzimidazole et d'azabenzimidazole, antagonistes des récepteurs au thromboxane; leurs procédés de préparation, intermédiaires de synthèse, compositions les contenant | |
| US4514568A (en) | 5-(4-Nitrophenyl)-2(1H)-pyrazinones | |
| CH628344A5 (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. | |
| EP0232659B1 (fr) | Nouvelles phényl naphtyridines comportant un substituant méthyle en position 3, et les médicaments qui en contiennent | |
| CH649994A5 (fr) | Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant. | |
| FR2527206A1 (fr) | Nouveaux derives de la 2(1h)-pyridinone, leur preparation et leur utilisation comme medicaments | |
| BE672578A (enrdf_load_stackoverflow) | ||
| US2149279A (en) | Derivatives of pyrazine carboxylic acid and processes for their production | |
| CA1256113A (fr) | Procede de preparation de derives du 4h-1,2,4- triazole | |
| US2876262A (en) | Basically substituted butyric acid amides and a process of preparing them | |
| BE798841A (fr) | Nouveaux derives d'acide sulfamoylbenzoique et leur procede de preparation | |
| CH414668A (fr) | Procédé de préparation de l'acide N-(2,3-diméthylphényl)-anthranilique | |
| FR2458550A1 (fr) | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant | |
| BE627999A (enrdf_load_stackoverflow) | ||
| BE896678A (fr) | Nouveaux derives de la 2 (1h)-pyridinone, leur preparation et leur utilisation comme medicaments. | |
| BE634833A (enrdf_load_stackoverflow) | ||
| BE565942A (enrdf_load_stackoverflow) | ||
| BE595766A (enrdf_load_stackoverflow) | ||
| BE658424A (enrdf_load_stackoverflow) | ||
| BE659237A (enrdf_load_stackoverflow) | ||
| BE713473A (enrdf_load_stackoverflow) | ||
| CH498084A (de) | Verfahren zur Herstellung von (para-(Acylamino)-phenyl)-O-acylsalicylaten | |
| BE492921A (enrdf_load_stackoverflow) | ||
| BE557134A (enrdf_load_stackoverflow) | ||
| BE857917A (fr) | Nouveaux derives de la piperidine, leur preparation et leur application comme medicaments |