CA1137109A - N,n'-diphenylhydrazine derivative - Google Patents
N,n'-diphenylhydrazine derivativeInfo
- Publication number
- CA1137109A CA1137109A CA000350169A CA350169A CA1137109A CA 1137109 A CA1137109 A CA 1137109A CA 000350169 A CA000350169 A CA 000350169A CA 350169 A CA350169 A CA 350169A CA 1137109 A CA1137109 A CA 1137109A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- salt
- hydrolysis
- butenyl
- methyl
- 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.)
- Expired
Links
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical class C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 159000000007 calcium salts Chemical class 0.000 claims description 15
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 6
- 239000001110 calcium chloride Substances 0.000 claims description 6
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical group [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 8
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 8
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 241000700159 Rattus Species 0.000 description 32
- 206010030113 Oedema Diseases 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 239000011575 calcium Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- RKINNRASCJRSHD-UHFFFAOYSA-L bumadizone calcium Chemical compound [Ca+2].C=1C=CC=CC=1N(C(=O)C(C([O-])=O)CCCC)NC1=CC=CC=C1.C=1C=CC=CC=1N(C(=O)C(C([O-])=O)CCCC)NC1=CC=CC=C1 RKINNRASCJRSHD-UHFFFAOYSA-L 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000001754 anti-pyretic effect Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 206010003246 arthritis Diseases 0.000 description 5
- 210000000548 hind-foot Anatomy 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000001562 ulcerogenic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- FLWFHHFTIRLFPV-UHFFFAOYSA-N bumadizone Chemical compound C=1C=CC=CC=1N(C(=O)C(C(O)=O)CCCC)NC1=CC=CC=C1 FLWFHHFTIRLFPV-UHFFFAOYSA-N 0.000 description 3
- 229960003354 bumadizone Drugs 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- -1 alkaline earth metal salts Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- VOPQFIACWMKPDI-UHFFFAOYSA-N 2-ethoxycarbonyl-5-methylhex-4-enoic acid Chemical compound CCOC(=O)C(C(O)=O)CC=C(C)C VOPQFIACWMKPDI-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 238000001061 Dunnett's test Methods 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- UYCAGRPOUWSBIQ-WOYAITHZSA-N [(1s)-1-carboxy-4-(diaminomethylideneamino)butyl]azanium;(2s)-5-oxopyrrolidine-2-carboxylate Chemical compound OC(=O)[C@@H]1CCC(=O)N1.OC(=O)[C@@H](N)CCCN=C(N)N UYCAGRPOUWSBIQ-WOYAITHZSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2915949.7 | 1979-04-20 | ||
| DE19792915949 DE2915949A1 (de) | 1979-04-20 | 1979-04-20 | Neues n,n'-diphenylhydrazinderivat und verfahren zu seiner herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1137109A true CA1137109A (en) | 1982-12-07 |
Family
ID=6068774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000350169A Expired CA1137109A (en) | 1979-04-20 | 1980-04-18 | N,n'-diphenylhydrazine derivative |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4301177A (index.php) |
| JP (1) | JPS55141455A (index.php) |
| AT (1) | AT371803B (index.php) |
| AU (1) | AU532354B2 (index.php) |
| BE (1) | BE882898A (index.php) |
| CA (1) | CA1137109A (index.php) |
| CH (1) | CH644097A5 (index.php) |
| DE (1) | DE2915949A1 (index.php) |
| DK (1) | DK149214C (index.php) |
| ES (1) | ES489925A1 (index.php) |
| FI (1) | FI801255A7 (index.php) |
| FR (1) | FR2454437A1 (index.php) |
| GB (1) | GB2048265A (index.php) |
| GR (1) | GR67303B (index.php) |
| IT (1) | IT1207105B (index.php) |
| NL (1) | NL8002269A (index.php) |
| NO (1) | NO148553C (index.php) |
| PT (1) | PT71113B (index.php) |
| SE (1) | SE449095B (index.php) |
| ZA (1) | ZA802347B (index.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5519057A (en) * | 1986-11-14 | 1996-05-21 | Johnson & Johnson--Merck Pharmaceuticals Co. | Ibuprofen-containing medicament |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH421989A (de) * | 1963-06-07 | 1966-10-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Malonsäuremonohydraziden |
| US3288848A (en) * | 1964-12-21 | 1966-11-29 | Upjohn Co | Alpha-amino dibasic acid hydrazides |
| US3470911A (en) * | 1967-11-17 | 1969-10-07 | Honeywell Inc | Double valve head |
-
1979
- 1979-04-20 DE DE19792915949 patent/DE2915949A1/de not_active Withdrawn
-
1980
- 1980-03-26 ES ES489925A patent/ES489925A1/es not_active Expired
- 1980-03-31 US US06/135,865 patent/US4301177A/en not_active Expired - Lifetime
- 1980-04-15 GR GR61691A patent/GR67303B/el unknown
- 1980-04-15 JP JP4951480A patent/JPS55141455A/ja active Pending
- 1980-04-17 CH CH298780A patent/CH644097A5/de not_active IP Right Cessation
- 1980-04-17 FR FR8008610A patent/FR2454437A1/fr active Granted
- 1980-04-18 GB GB8012885A patent/GB2048265A/en not_active Withdrawn
- 1980-04-18 PT PT71113A patent/PT71113B/pt unknown
- 1980-04-18 CA CA000350169A patent/CA1137109A/en not_active Expired
- 1980-04-18 AU AU57586/80A patent/AU532354B2/en not_active Ceased
- 1980-04-18 NL NL8002269A patent/NL8002269A/nl not_active Application Discontinuation
- 1980-04-18 NO NO801129A patent/NO148553C/no unknown
- 1980-04-18 IT IT8048452A patent/IT1207105B/it active
- 1980-04-18 SE SE8002937A patent/SE449095B/sv not_active IP Right Cessation
- 1980-04-18 DK DK167380A patent/DK149214C/da not_active IP Right Cessation
- 1980-04-18 ZA ZA00802347A patent/ZA802347B/xx unknown
- 1980-04-18 FI FI801255A patent/FI801255A7/fi not_active Application Discontinuation
- 1980-04-18 AT AT0211480A patent/AT371803B/de not_active IP Right Cessation
- 1980-04-21 BE BE0/200315A patent/BE882898A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO148553B (no) | 1983-07-25 |
| FI801255A7 (fi) | 1981-01-01 |
| ES489925A1 (es) | 1980-10-01 |
| FR2454437A1 (fr) | 1980-11-14 |
| DK149214C (da) | 1986-08-04 |
| SE449095B (sv) | 1987-04-06 |
| AU5758680A (en) | 1980-10-23 |
| ZA802347B (en) | 1981-12-30 |
| GB2048265A (en) | 1980-12-10 |
| AT371803B (de) | 1983-08-10 |
| PT71113A (pt) | 1980-05-01 |
| DE2915949A1 (de) | 1980-11-06 |
| ATA211480A (de) | 1982-12-15 |
| IT1207105B (it) | 1989-05-17 |
| IT8048452A0 (it) | 1980-04-18 |
| SE8002937L (sv) | 1980-10-21 |
| PT71113B (pt) | 1981-08-07 |
| FR2454437B1 (index.php) | 1984-10-19 |
| NO148553C (no) | 1983-11-02 |
| NL8002269A (nl) | 1980-10-22 |
| JPS55141455A (en) | 1980-11-05 |
| AU532354B2 (en) | 1983-09-29 |
| GR67303B (index.php) | 1981-06-29 |
| NO801129L (no) | 1980-10-21 |
| US4301177A (en) | 1981-11-17 |
| CH644097A5 (de) | 1984-07-13 |
| BE882898A (fr) | 1980-10-21 |
| DK167380A (da) | 1980-10-21 |
| DK149214B (da) | 1986-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |