DE2537590A1 - Neue phenylbutazon-derivate - Google Patents
Neue phenylbutazon-derivateInfo
- Publication number
- DE2537590A1 DE2537590A1 DE19752537590 DE2537590A DE2537590A1 DE 2537590 A1 DE2537590 A1 DE 2537590A1 DE 19752537590 DE19752537590 DE 19752537590 DE 2537590 A DE2537590 A DE 2537590A DE 2537590 A1 DE2537590 A1 DE 2537590A1
- Authority
- DE
- Germany
- Prior art keywords
- phenylbutazone
- proline
- new
- derivatives
- radical
- 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.)
- Ceased
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
- 229960002895 phenylbutazone Drugs 0.000 claims description 22
- 229960002429 proline Drugs 0.000 claims description 13
- -1 Enol esters Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 208000025747 Rheumatic disease Diseases 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
- 230000000552 rheumatic effect Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 208000025865 Ulcer Diseases 0.000 description 8
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 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
- 229930182821 L-proline Natural products 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000004054 inflammatory process Effects 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
- 208000011580 syndromic disease Diseases 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 208000006820 Arthralgia Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010009137 Chronic sinusitis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GNMSLDIYJOSUSW-LURJTMIESA-N N-acetyl-L-proline Chemical compound CC(=O)N1CCC[C@H]1C(O)=O GNMSLDIYJOSUSW-LURJTMIESA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 description 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 210000002249 digestive system Anatomy 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
- 210000005069 ears Anatomy 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000001562 ulcerogenic effect Effects 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 |
|---|---|
| DE2537590A1 true DE2537590A1 (de) | 1976-03-11 |
Family
ID=9142574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752537590 Ceased DE2537590A1 (de) | 1974-08-26 | 1975-08-23 | Neue phenylbutazon-derivate |
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 |
| DK381075A (en:Method) | 1976-02-27 |
| FI752387A7 (en:Method) | 1976-02-27 |
| NO142220C (no) | 1980-07-16 |
| CH615434A5 (en) | 1980-01-31 |
| GB1482380A (en) | 1977-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D403/12 |
|
| 8126 | Change of the secondary classification |
Ipc: A61K 31/40 |
|
| 8131 | Rejection |