CH660480A5 - Derivati dell'acido d-2-(6-metossi-2-naftil) propionico ad attivita terapeutica, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. - Google Patents
Derivati dell'acido d-2-(6-metossi-2-naftil) propionico ad attivita terapeutica, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. Download PDFInfo
- Publication number
- CH660480A5 CH660480A5 CH1411/83A CH141183A CH660480A5 CH 660480 A5 CH660480 A5 CH 660480A5 CH 1411/83 A CH1411/83 A CH 1411/83A CH 141183 A CH141183 A CH 141183A CH 660480 A5 CH660480 A5 CH 660480A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methoxy
- preparation
- process according
- reaction
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 15
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical class C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- XBRZFXDDHZFXNY-UHFFFAOYSA-N C(=O)(O)C1=CC=C(NC(CC2=C(C3=CC=C(C=C3C=C2)OC)C)=O)C=C1 Chemical compound C(=O)(O)C1=CC=C(NC(CC2=C(C3=CC=C(C=C3C=C2)OC)C)=O)C=C1 XBRZFXDDHZFXNY-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 6-methoxy-2-naphthyl Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 229960002009 naproxen Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 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 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (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 |
|---|---|---|---|
| IT20190/82A IT1150687B (it) | 1982-03-16 | 1982-03-16 | Derivati dell'acido d-2-(6-metossi-2-naftil) propionico ad attivita' terapeutica,procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH660480A5 true CH660480A5 (it) | 1987-04-30 |
Family
ID=11164574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1411/83A CH660480A5 (it) | 1982-03-16 | 1983-03-15 | Derivati dell'acido d-2-(6-metossi-2-naftil) propionico ad attivita terapeutica, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. |
Country Status (6)
| Country | Link |
|---|---|
| KR (1) | KR840003812A (enrdf_load_stackoverflow) |
| CH (1) | CH660480A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3309258A1 (enrdf_load_stackoverflow) |
| ES (1) | ES8403860A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2523577B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1150687B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2505411A1 (fr) * | 1981-05-08 | 1982-11-12 | Binder Adam | Dispositif de recuperation de l'energie du vent |
| DE3668450D1 (de) * | 1985-03-14 | 1990-03-01 | Smithkline Dauelsberg | 5-aminosalicylsaeurederivate von nicht-steroidalen entzuendungshemmenden sauren. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978116A (en) * | 1971-11-04 | 1976-08-31 | Syntex Corporation | 2-naphthyl acetic acid derivatives and compositions and methods thereof |
| IT1064700B (it) * | 1976-07-28 | 1985-02-25 | Pessina Raffaele | Procedimento per la preparazione dell acido d.2.6 metossi 2 naftil profionico |
| FR2388789A1 (fr) * | 1977-04-27 | 1978-11-24 | Seuref Ag | Derives d'acide benzoique, leur procede de preparation et leur application therapeutique |
| FR2416214A1 (fr) * | 1978-02-02 | 1979-08-31 | Inst Rech Scient Irs | Derives d'acide naphtyl-1 acetique, leur procede de preparation et leur application therapeutique |
-
1982
- 1982-03-16 IT IT20190/82A patent/IT1150687B/it active
-
1983
- 1983-03-15 KR KR1019830001037A patent/KR840003812A/ko not_active Ceased
- 1983-03-15 CH CH1411/83A patent/CH660480A5/it not_active IP Right Cessation
- 1983-03-15 ES ES520623A patent/ES8403860A1/es not_active Expired
- 1983-03-15 DE DE19833309258 patent/DE3309258A1/de active Granted
- 1983-03-16 FR FR8304302A patent/FR2523577B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2523577B1 (fr) | 1986-10-31 |
| IT1150687B (it) | 1986-12-17 |
| KR840003812A (ko) | 1984-10-04 |
| ES520623A0 (es) | 1984-04-01 |
| FR2523577A1 (fr) | 1983-09-23 |
| ES8403860A1 (es) | 1984-04-01 |
| DE3309258C2 (enrdf_load_stackoverflow) | 1990-10-04 |
| IT8220190A0 (it) | 1982-03-16 |
| DE3309258A1 (de) | 1983-09-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Shanbhag et al. | Ester and amide prodrugs of ibuprofen and naproxen: synthesis, anti-inflammatory activity, and gastrointestinal toxicity | |
| US6040341A (en) | Compounds and their compositions having anti-inflammatory and anti-thrombotic activities | |
| US5208255A (en) | Thioester enantiomeric compounds and their therapeutic uses | |
| Tammara et al. | Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and naproxen | |
| PT86811B (pt) | Processo para a preparacao de amidas de acidos gordos saturados inibidoras do acil-coenzima a: colesterol aciltransferase e de composicoes farmaceuticas que as contem | |
| JPS6229566A (ja) | 新規グアニジノメチル安息香酸誘導体 | |
| US5221692A (en) | Ether linked and relatively nonpungent analogues of N-nonanoyl vanillylamide | |
| JPS61180784A (ja) | チオフエン誘導体及び該チオフエン誘導体を有効成分とする医薬組成物 | |
| CH660480A5 (it) | Derivati dell'acido d-2-(6-metossi-2-naftil) propionico ad attivita terapeutica, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. | |
| EP2010481A1 (fr) | Composes de type 1, 4-naphtoquinones, compositions les comprenant et utilisation de ces composes en tant qu'agents anti -cancereux | |
| IE60205B1 (en) | Pharmaceutically useful derivatives of thiazolidine-4-carboxylic acid | |
| WO1992016496A1 (en) | N-[[4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl]amino acids useful in the therapy of osteoarticular affections | |
| US5136076A (en) | Process for the preparation of amino acid-derived enatiomeric compounds | |
| CA1340006C (en) | Acylated cyanamide composition | |
| KR860000059B1 (ko) | 2-치환된-페닐-5-메틸티아졸리딘-4-온의 제조방법 | |
| US4460601A (en) | Dipeptides having a methionine residue and possessing a protective action for the liver | |
| US4879404A (en) | Novel salicylates, their salts, pharmaceutical compositions containing them and process for preparing same | |
| FR2491456A1 (enrdf_load_stackoverflow) | ||
| KR930006195B1 (ko) | 부텐산 아미드, 이들의 염, 이들을 함유하는 제약학적 조성물 및 이들의 제조방법 | |
| IE45417B1 (en) | Napthalene derivatives | |
| JPS6324498B2 (enrdf_load_stackoverflow) | ||
| JPS5910563A (ja) | α−（Ｎ−ピロリル）−フエニル酢酸誘導体およびその製造方法 | |
| US4795758A (en) | 5-[2-(pyrrolidin-1-yl)ethoxy]-p-cymene derivatives, the process for the preparation of the said derivatives and drugs in which the said derivatives are present | |
| WO1989000159A1 (en) | Derivatives of cyclic amino acids, their salts, pharmaceutical compositions containing them and process for preparing same | |
| FI75157C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefull 3-(2-metoxi-fenoxi)-3-metyl-benso-2,4- dioxacyklohexanon. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |