DE2316802A1 - Neue derivate des phenylbutazons - Google Patents
Neue derivate des phenylbutazonsInfo
- Publication number
- DE2316802A1 DE2316802A1 DE19732316802 DE2316802A DE2316802A1 DE 2316802 A1 DE2316802 A1 DE 2316802A1 DE 19732316802 DE19732316802 DE 19732316802 DE 2316802 A DE2316802 A DE 2316802A DE 2316802 A1 DE2316802 A1 DE 2316802A1
- Authority
- DE
- Germany
- Prior art keywords
- phenylbutazone
- general formula
- new derivatives
- radical
- formula
- 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.)
- Pending
Links
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical class O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 title claims description 29
- 229960002895 phenylbutazone Drugs 0.000 claims description 19
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 235000001014 amino acid Nutrition 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004472 Lysine Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- YGYLYUIRSJSFJS-QMMMGPOBSA-N benzyl (2s)-2-aminopropanoate Chemical compound C[C@H](N)C(=O)OCC1=CC=CC=C1 YGYLYUIRSJSFJS-QMMMGPOBSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 230000000552 rheumatic effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- -1 alkyl radical Chemical class 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010036030 Polyarthritis Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000003412 degenerative effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 208000030428 polyarticular arthritis Diseases 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000711981 Sais Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 210000004247 hand Anatomy 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7212386A FR2178818A1 (en) | 1972-04-07 | 1972-04-07 | Phenylbutazone - aminoacid salts - anti-inflammatories and analgesics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2316802A1 true DE2316802A1 (de) | 1973-10-18 |
Family
ID=9096539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732316802 Pending DE2316802A1 (de) | 1972-04-07 | 1973-04-04 | Neue derivate des phenylbutazons |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4947516A (enrdf_load_stackoverflow) |
| BE (1) | BE797900A (enrdf_load_stackoverflow) |
| DE (1) | DE2316802A1 (enrdf_load_stackoverflow) |
| DK (1) | DK128853B (enrdf_load_stackoverflow) |
| FR (1) | FR2178818A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7304805A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279926A (en) * | 1974-03-07 | 1981-07-21 | Spa-Societa Prodotti Antibiotici S.P.A. | Method of relieving pain and treating inflammatory conditions in warm-blooded animals |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55102152A (en) * | 1979-01-29 | 1980-08-05 | Matsushita Electronics Corp | Method and device for forming fluorescent film |
| JPS6095848A (ja) * | 1984-08-23 | 1985-05-29 | Matsushita Electronics Corp | 小形けい光灯の製造方法 |
-
1972
- 1972-04-07 FR FR7212386A patent/FR2178818A1/fr active Granted
-
1973
- 1973-04-04 DE DE19732316802 patent/DE2316802A1/de active Pending
- 1973-04-05 DK DK185473A patent/DK128853B/da unknown
- 1973-04-06 JP JP3940873A patent/JPS4947516A/ja active Pending
- 1973-04-06 BE BE129754A patent/BE797900A/xx unknown
- 1973-04-06 NL NL7304805A patent/NL7304805A/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279926A (en) * | 1974-03-07 | 1981-07-21 | Spa-Societa Prodotti Antibiotici S.P.A. | Method of relieving pain and treating inflammatory conditions in warm-blooded animals |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2178818A1 (en) | 1973-11-16 |
| DK128853B (da) | 1974-07-15 |
| JPS4947516A (enrdf_load_stackoverflow) | 1974-05-08 |
| NL7304805A (enrdf_load_stackoverflow) | 1973-10-09 |
| BE797900A (fr) | 1973-10-08 |
| FR2178818B1 (enrdf_load_stackoverflow) | 1975-06-20 |
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