CH615434A5 - Process for the preparation of novel phenylbutazone derivatives - Google Patents
Process for the preparation of novel phenylbutazone derivatives Download PDFInfo
- Publication number
- CH615434A5 CH615434A5 CH1107275A CH1107275A CH615434A5 CH 615434 A5 CH615434 A5 CH 615434A5 CH 1107275 A CH1107275 A CH 1107275A CH 1107275 A CH1107275 A CH 1107275A CH 615434 A5 CH615434 A5 CH 615434A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylbutazone
- proline
- preparation
- derivatives
- compound
- Prior art date
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 26
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229960002895 phenylbutazone Drugs 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 210000002249 digestive system Anatomy 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 229960002429 proline Drugs 0.000 description 10
- 208000025865 Ulcer Diseases 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 enol esters Chemical class 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229930182821 L-proline Natural products 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GNMSLDIYJOSUSW-UHFFFAOYSA-N N-Acetyl-proline Chemical compound CC(=O)N1CCCC1C(O)=O GNMSLDIYJOSUSW-UHFFFAOYSA-N 0.000 description 2
- GNMSLDIYJOSUSW-LURJTMIESA-N N-acetyl-L-proline Chemical compound CC(=O)N1CCC[C@H]1C(O)=O GNMSLDIYJOSUSW-LURJTMIESA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- ORBIGZZHMAJXAZ-UHFFFAOYSA-N pyridine-4-carbonyl pyridine-4-carboxylate Chemical compound C=1C=NC=CC=1C(=O)OC(=O)C1=CC=NC=C1 ORBIGZZHMAJXAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000001562 ulcerogenic effect Effects 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7429109A FR2282884A1 (fr) | 1974-08-26 | 1974-08-26 | Nouveaux derives de la phenylbutazone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615434A5 true CH615434A5 (en) | 1980-01-31 |
Family
ID=9142574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1107275A CH615434A5 (en) | 1974-08-26 | 1975-08-26 | Process for the preparation of novel phenylbutazone derivatives |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT343111B (en:Method) |
| BE (1) | BE832722A (en:Method) |
| CH (1) | CH615434A5 (en:Method) |
| DE (1) | DE2537590A1 (en:Method) |
| DK (1) | DK138495B (en:Method) |
| FI (1) | FI61893C (en:Method) |
| FR (1) | FR2282884A1 (en:Method) |
| GB (1) | GB1482380A (en:Method) |
| IE (1) | IE41788B1 (en:Method) |
| LU (1) | LU73250A1 (en:Method) |
| NL (1) | NL7509999A (en:Method) |
| NO (1) | NO142220C (en:Method) |
| SE (1) | SE421618B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1604045A (en) * | 1977-06-01 | 1981-12-02 | Sterwin Ag | -(2-methyl-indol-3-yl)-acetic acid esters processes for its prepartion and pharmaceutical compositions incorporating the same |
-
1974
- 1974-08-26 FR FR7429109A patent/FR2282884A1/fr active Granted
-
1975
- 1975-08-22 AT AT650175A patent/AT343111B/de not_active IP Right Cessation
- 1975-08-23 DE DE19752537590 patent/DE2537590A1/de not_active Ceased
- 1975-08-25 SE SE7509449A patent/SE421618B/xx unknown
- 1975-08-25 NL NL7509999A patent/NL7509999A/xx unknown
- 1975-08-25 BE BE159444A patent/BE832722A/xx not_active IP Right Cessation
- 1975-08-25 NO NO752923A patent/NO142220C/no unknown
- 1975-08-25 IE IE1861/75A patent/IE41788B1/en unknown
- 1975-08-25 DK DK381075AA patent/DK138495B/da unknown
- 1975-08-25 LU LU73250A patent/LU73250A1/xx unknown
- 1975-08-25 FI FI752387A patent/FI61893C/fi not_active IP Right Cessation
- 1975-08-26 CH CH1107275A patent/CH615434A5/de not_active IP Right Cessation
- 1975-08-26 GB GB35252/75A patent/GB1482380A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7509999A (nl) | 1976-03-01 |
| ATA650175A (de) | 1977-09-15 |
| FR2282884B1 (en:Method) | 1978-07-21 |
| DK138495C (en:Method) | 1979-03-05 |
| NO142220B (no) | 1980-04-08 |
| IE41788L (en) | 1976-02-26 |
| LU73250A1 (en:Method) | 1977-01-07 |
| FI61893C (fi) | 1982-10-11 |
| FI61893B (fi) | 1982-06-30 |
| IE41788B1 (en) | 1980-03-26 |
| SE7509449L (sv) | 1976-02-27 |
| NO752923L (en:Method) | 1976-02-27 |
| AT343111B (de) | 1978-05-10 |
| FR2282884A1 (fr) | 1976-03-26 |
| DK138495B (da) | 1978-09-18 |
| BE832722A (fr) | 1976-02-25 |
| SE421618B (sv) | 1982-01-18 |
| DE2537590A1 (de) | 1976-03-11 |
| DK381075A (en:Method) | 1976-02-27 |
| FI752387A7 (en:Method) | 1976-02-27 |
| NO142220C (no) | 1980-07-16 |
| GB1482380A (en) | 1977-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |