FI59787C - Foerfarande foer framstaellning av biologiskt aktiva 4-cyklopropylmetylenoxi-3-klorfenylaettiksyra och dess farmaceutiskt anvaendbara salter - Google Patents
Foerfarande foer framstaellning av biologiskt aktiva 4-cyklopropylmetylenoxi-3-klorfenylaettiksyra och dess farmaceutiskt anvaendbara salter Download PDFInfo
- Publication number
- FI59787C FI59787C FI750056A FI750056A FI59787C FI 59787 C FI59787 C FI 59787C FI 750056 A FI750056 A FI 750056A FI 750056 A FI750056 A FI 750056A FI 59787 C FI59787 C FI 59787C
- Authority
- FI
- Finland
- Prior art keywords
- pharmaceutical
- cyclopropylmethylenoxy
- anvaendbara
- salter
- acetic acid
- Prior art date
Links
- 241000277284 Salvelinus fontinalis Species 0.000 title 1
- 235000013399 edible fruits Nutrition 0.000 title 1
- 241001465754 Metazoa Species 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000001754 anti-pyretic effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002221 antipyretic Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical class NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- 208000000114 Pain Threshold Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 230000003187 abdominal effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000037040 pain threshold Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108010023063 Bacto-peptone Proteins 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100055024 Mus musculus Aftph gene Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 1
- 229960005142 alclofenac Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 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
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- -1 cyclopropylmethylene halide Chemical class 0.000 description 1
- XAXQZMVQJJBADI-UHFFFAOYSA-N dibromomethylcyclopropane Chemical compound BrC(Br)C1CC1 XAXQZMVQJJBADI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 208000021760 high fever Diseases 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ACBFEXJHCINJDS-UHFFFAOYSA-N methyl 2-(3-chloro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(Cl)=C1 ACBFEXJHCINJDS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- 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
-
- 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)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1936674 | 1974-01-14 | ||
| IT1936674 | 1974-01-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750056A7 FI750056A7 (en, 2012) | 1975-07-15 |
| FI59787B FI59787B (fi) | 1981-06-30 |
| FI59787C true FI59787C (fi) | 1981-10-12 |
Family
ID=11157078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750056A FI59787C (fi) | 1974-01-14 | 1975-01-09 | Foerfarande foer framstaellning av biologiskt aktiva 4-cyklopropylmetylenoxi-3-klorfenylaettiksyra och dess farmaceutiskt anvaendbara salter |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3976673A (en, 2012) |
| JP (1) | JPS5218697B2 (en, 2012) |
| AR (1) | AR203883A1 (en, 2012) |
| AT (1) | AT338252B (en, 2012) |
| BE (1) | BE824300A (en, 2012) |
| CA (1) | CA1041541A (en, 2012) |
| CH (1) | CH593896A5 (en, 2012) |
| CS (1) | CS181686B2 (en, 2012) |
| DE (1) | DE2500808B2 (en, 2012) |
| DK (1) | DK140590B (en, 2012) |
| ES (1) | ES433748A1 (en, 2012) |
| FI (1) | FI59787C (en, 2012) |
| FR (1) | FR2257284B1 (en, 2012) |
| GB (1) | GB1448547A (en, 2012) |
| HU (1) | HU168049B (en, 2012) |
| IN (1) | IN140121B (en, 2012) |
| LU (1) | LU71616A1 (en, 2012) |
| NL (1) | NL7500387A (en, 2012) |
| NO (1) | NO143402C (en, 2012) |
| SE (1) | SE411447B (en, 2012) |
| SU (1) | SU667128A3 (en, 2012) |
| YU (1) | YU4075A (en, 2012) |
| ZA (1) | ZA75194B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521171A (en) * | 1975-03-31 | 1996-05-28 | Sorenson; John R. J. | Anti-inflammatory and anti-ulcer compounds and process |
| US5216021A (en) * | 1986-08-28 | 1993-06-01 | Sorenson John R J | Analgesic method |
| US4999347A (en) * | 1986-08-28 | 1991-03-12 | Sorenson John R J | Analgesic method |
| US5635532A (en) * | 1991-10-21 | 1997-06-03 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Compositions and methods for therapy and prevention of pathologies including cancer, AIDS and anemia |
| US6037376A (en) * | 1991-10-21 | 2000-03-14 | The United States Of America As Represented By The Department Of Health And Human Services | Methods for therapy of cancer |
| US5605930A (en) * | 1991-10-21 | 1997-02-25 | The United States Of America As Represented By The Department Of Health And Human Services | Compositions and methods for treating and preventing pathologies including cancer |
| ES2530235T3 (es) * | 2003-02-13 | 2015-02-27 | Wellstat Therapeutics Corporation | Compuestos para el tratamiento de trastornos metabólicos |
| CN116621689A (zh) * | 2023-04-24 | 2023-08-22 | 山东省药学科学院 | 一种l-赖氨酸-联苯乙酸盐及其制备方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE32439B1 (en) * | 1967-09-27 | 1973-08-08 | Madan Ag | Substituted phenylacetic acids and process of preparation thereof |
| US3553226A (en) * | 1968-04-04 | 1971-01-05 | Smith Kline French Lab | 1-(2-benzoylcyclopropylmethyl)-4-phenyl-1,2,5,6- tetrahydropyridines |
| US3786085A (en) * | 1969-09-17 | 1974-01-15 | Ciba Geigy Corp | Aryl substituted cycloaliphatic acids |
| GB1308327A (en) * | 1970-04-14 | 1973-02-21 | Reckitt & Colmann Prod Ltd | Phenylalkane derivatives and processes for the preparation thereof |
-
1975
- 1975-01-09 CS CS7500000182A patent/CS181686B2/cs unknown
- 1975-01-09 US US05/539,912 patent/US3976673A/en not_active Expired - Lifetime
- 1975-01-09 YU YU00040/75A patent/YU4075A/xx unknown
- 1975-01-09 CA CA217,669A patent/CA1041541A/en not_active Expired
- 1975-01-09 AT AT12375A patent/AT338252B/de not_active IP Right Cessation
- 1975-01-09 IN IN50/CAL/75A patent/IN140121B/en unknown
- 1975-01-09 FI FI750056A patent/FI59787C/fi not_active IP Right Cessation
- 1975-01-09 AR AR257243A patent/AR203883A1/es active
- 1975-01-10 BE BE152306A patent/BE824300A/xx unknown
- 1975-01-10 LU LU71616A patent/LU71616A1/xx unknown
- 1975-01-10 ZA ZA00750194A patent/ZA75194B/xx unknown
- 1975-01-10 JP JP50005057A patent/JPS5218697B2/ja not_active Expired
- 1975-01-10 DE DE19752500808 patent/DE2500808B2/de active Granted
- 1975-01-10 FR FR7500643A patent/FR2257284B1/fr not_active Expired
- 1975-01-10 SE SE7500277A patent/SE411447B/xx unknown
- 1975-01-10 GB GB109675A patent/GB1448547A/en not_active Expired
- 1975-01-13 HU HUIE668A patent/HU168049B/hu not_active IP Right Cessation
- 1975-01-13 ES ES433748A patent/ES433748A1/es not_active Expired
- 1975-01-13 NO NO750086A patent/NO143402C/no unknown
- 1975-01-13 DK DK7575AA patent/DK140590B/da unknown
- 1975-01-13 NL NL7500387A patent/NL7500387A/xx not_active Application Discontinuation
- 1975-01-13 SU SU752096344A patent/SU667128A3/ru active
- 1975-01-13 CH CH30375A patent/CH593896A5/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: I.S.F. S.P.A. |