IL45191A - Acid 5 - Fivaloalkyloxy - 5 - 1) 1 - Phenylethyl (barbiturate, process for preparation and exhibitions of pain layers based on it - Google Patents
Acid 5 - Fivaloalkyloxy - 5 - 1) 1 - Phenylethyl (barbiturate, process for preparation and exhibitions of pain layers based on itInfo
- Publication number
- IL45191A IL45191A IL45191A IL4519174A IL45191A IL 45191 A IL45191 A IL 45191A IL 45191 A IL45191 A IL 45191A IL 4519174 A IL4519174 A IL 4519174A IL 45191 A IL45191 A IL 45191A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- barbituric acid
- phenylethyl
- preparing
- pivaloyloxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title claims description 6
- HXXFJOVGNHNALL-UHFFFAOYSA-N [2,4,6-trioxo-5-(1-phenylethyl)-1,3-diazinan-5-yl] 2,2-dimethylpropanoate Chemical compound O=C1NC(=O)NC(=O)C1(OC(=O)C(C)(C)C)C(C)C1=CC=CC=C1 HXXFJOVGNHNALL-UHFFFAOYSA-N 0.000 title claims 2
- 230000000202 analgesic effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 pivaloyl halide Chemical class 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- QCEBYHHMBUBEBE-UHFFFAOYSA-N 5-hydroxy-5-(1-phenylethyl)-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1(O)C(C)C1=CC=CC=C1 QCEBYHHMBUBEBE-UHFFFAOYSA-N 0.000 claims 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical group CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000007656 barbituric acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MENIJRPFVLNJIH-UHFFFAOYSA-N 5-benzyl-1,3-diazinane-2,4,6-trione Chemical class O=C1NC(=O)NC(=O)C1CC1=CC=CC=C1 MENIJRPFVLNJIH-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- SDCJMBBHNJPYGW-UHFFFAOYSA-L disodium;hydrogen carbonate;chloride Chemical class [Na+].[Na+].Cl.[O-]C([O-])=O SDCJMBBHNJPYGW-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US378482A US3894023A (en) | 1973-07-12 | 1973-07-12 | 5-Pivaloyloxy-5-(1-phenylethyl) barbituric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45191A0 IL45191A0 (en) | 1974-10-22 |
| IL45191A true IL45191A (en) | 1977-08-31 |
Family
ID=23493290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45191A IL45191A (en) | 1973-07-12 | 1974-07-03 | Acid 5 - Fivaloalkyloxy - 5 - 1) 1 - Phenylethyl (barbiturate, process for preparation and exhibitions of pain layers based on it |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3894023A (de) |
| JP (1) | JPS5946944B2 (de) |
| AT (1) | AT330795B (de) |
| AU (1) | AU477319B2 (de) |
| BE (1) | BE817569A (de) |
| CA (1) | CA1010867A (de) |
| CH (1) | CH605830A5 (de) |
| DE (1) | DE2433268C2 (de) |
| ES (1) | ES428172A1 (de) |
| FR (1) | FR2236500B1 (de) |
| GB (1) | GB1417384A (de) |
| IL (1) | IL45191A (de) |
| LU (1) | LU70511A1 (de) |
| MX (1) | MX3264E (de) |
| PH (1) | PH11471A (de) |
| SE (1) | SE409995B (de) |
| ZA (1) | ZA744241B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55126935A (en) * | 1979-03-23 | 1980-10-01 | Fujitsu Ltd | Correction method of inter-electrode jumpering |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR194578A1 (es) * | 1970-11-09 | 1973-07-31 | Kendall & Co | Un procedimiento para preparar acidos 5-sustituidos-5-fenilalquil barbituricos y un compuesto intermedio obtenido durante dicho procedimiento |
-
1973
- 1973-07-12 US US378482A patent/US3894023A/en not_active Expired - Lifetime
-
1974
- 1974-06-28 GB GB2886074A patent/GB1417384A/en not_active Expired
- 1974-07-02 ZA ZA00744241A patent/ZA744241B/xx unknown
- 1974-07-03 IL IL45191A patent/IL45191A/en unknown
- 1974-07-08 AT AT562974A patent/AT330795B/de not_active IP Right Cessation
- 1974-07-08 AU AU70943/74A patent/AU477319B2/en not_active Expired
- 1974-07-10 SE SE7409081A patent/SE409995B/xx not_active IP Right Cessation
- 1974-07-11 DE DE2433268A patent/DE2433268C2/de not_active Expired
- 1974-07-11 ES ES428172A patent/ES428172A1/es not_active Expired
- 1974-07-11 LU LU70511A patent/LU70511A1/xx unknown
- 1974-07-11 MX MX003929U patent/MX3264E/es unknown
- 1974-07-11 CA CA204,618A patent/CA1010867A/en not_active Expired
- 1974-07-11 BE BE146493A patent/BE817569A/xx not_active IP Right Cessation
- 1974-07-12 CH CH968074A patent/CH605830A5/xx not_active IP Right Cessation
- 1974-07-12 PH PH16033A patent/PH11471A/en unknown
- 1974-07-12 FR FR7424290A patent/FR2236500B1/fr not_active Expired
- 1974-07-12 JP JP49079273A patent/JPS5946944B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2236500B1 (de) | 1977-11-04 |
| PH11471A (en) | 1978-02-01 |
| ZA744241B (en) | 1975-07-30 |
| SE409995B (sv) | 1979-09-17 |
| CH605830A5 (de) | 1978-10-13 |
| MX3264E (es) | 1980-08-12 |
| US3894023A (en) | 1975-07-08 |
| JPS5946944B2 (ja) | 1984-11-15 |
| JPS5040581A (de) | 1975-04-14 |
| DE2433268C2 (de) | 1983-03-24 |
| ATA562974A (de) | 1975-10-15 |
| GB1417384A (en) | 1975-12-10 |
| IL45191A0 (en) | 1974-10-22 |
| AU7094374A (en) | 1976-01-08 |
| LU70511A1 (de) | 1974-11-28 |
| CA1010867A (en) | 1977-05-24 |
| DE2433268A1 (de) | 1975-01-30 |
| AT330795B (de) | 1976-07-26 |
| ES428172A1 (es) | 1976-11-16 |
| FR2236500A1 (de) | 1975-02-07 |
| BE817569A (fr) | 1974-11-04 |
| SE7409081L (sv) | 1975-01-13 |
| AU477319B2 (en) | 1976-10-21 |
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