CH642257A5 - Esteri di 2-(6-metossi-2-naftil)propile, processo per la loro preparazione e composizioni farmaceutiche che li contengono. - Google Patents

Esteri di 2-(6-metossi-2-naftil)propile, processo per la loro preparazione e composizioni farmaceutiche che li contengono. Download PDF

Info

Publication number: CH642257A5
Authority: CH; Switzerland
Prior art keywords: methoxy; ena; naphthyl; naproxen; hours
Prior art date: 1979-05-17

Application number

CH343580A

Other languages

English (en)

Italian (it)

Inventor

Rinaldo Del Bono

Original Assignee

Mediolanum Farmaceutici Srl

Priority date (The priority date 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 date listed.)

1979-05-17

Filing date

1980-05-02

Publication date

1984-04-13

1980-05-02 Application filed by Mediolanum Farmaceutici Srl filed Critical Mediolanum Farmaceutici Srl

1984-04-13 Publication of CH642257A5 publication Critical patent/CH642257A5/it

Links

-1 PROPYL ESTERS Chemical class 0.000 title claims description 22
238000000034 method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 10
230000000202 analgesic effect Effects 0.000 claims description 7
230000001754 anti-pyretic effect Effects 0.000 claims description 7
230000003110 anti-inflammatory effect Effects 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
230000003356 anti-rheumatic effect Effects 0.000 claims description 3
239000003435 antirheumatic agent Substances 0.000 claims description 3
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 32
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 32
229960002009 naproxen Drugs 0.000 description 31
230000000694 effects Effects 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
241000700159 Rattus Species 0.000 description 13
241001465754 Metazoa Species 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
206010030113 Oedema Diseases 0.000 description 8
241000283973 Oryctolagus cuniculus Species 0.000 description 7
239000000243 solution Substances 0.000 description 7
210000003754 fetus Anatomy 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000000829 suppository Substances 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 4
206010037660 Pyrexia Diseases 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000035935 pregnancy Effects 0.000 description 4
238000005303 weighing Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
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 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010055690 Foetal death Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
238000011887 Necropsy Methods 0.000 description 2
206010067482 No adverse event Diseases 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000003708 ampul Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
244000144987 brood Species 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
239000002826 coolant Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
231100001231 less toxic Toxicity 0.000 description 2
238000011068 loading method Methods 0.000 description 2
230000036244 malformation Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
229960000988 nystatin Drugs 0.000 description 2
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000725 suspension Substances 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
RCGQAPUWWHXBOK-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanal Chemical compound C1=C(C(C)C=O)C=CC2=CC(OC)=CC=C21 RCGQAPUWWHXBOK-UHFFFAOYSA-N 0.000 description 1
AEEKXZJYJVMYAP-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propyl acetate Chemical compound C1=C(C(C)COC(C)=O)C=CC2=CC(OC)=CC=C21 AEEKXZJYJVMYAP-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
206010018473 Glycosuria Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
206010033546 Pallor Diseases 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
241001275800 Zanclidae Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
206010016165 failure to thrive Diseases 0.000 description 1
231100001048 fetal toxicity Toxicity 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
208000006750 hematuria Diseases 0.000 description 1
UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
230000003908 liver function Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
230000000175 pyretogenic effect Effects 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

CH343580A 1979-05-17 1980-05-02 Esteri di 2-(6-metossi-2-naftil)propile, processo per la loro preparazione e composizioni farmaceutiche che li contengono. CH642257A5 (it)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT22738/79A IT1114245B (it)	1979-05-17	1979-05-17	Esteri di 2-(6-metossi-2-naftil)propile,processo per la loro preparazione e composizioni farmaceutiche che li contengono

Publications (1)

Publication Number	Publication Date
CH642257A5 true CH642257A5 (it)	1984-04-13

Family

ID=11199868

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH343580A CH642257A5 (it)	1979-05-17	1980-05-02	Esteri di 2-(6-metossi-2-naftil)propile, processo per la loro preparazione e composizioni farmaceutiche che li contengono.

Country Status (19)

Country	Link
JP (1)	JPS5625131A (de)
AT (1)	AT366359B (de)
AU (1)	AU516763B2 (de)
BE (1)	BE883330A (de)
CH (1)	CH642257A5 (de)
DE (1)	DE3016616C2 (de)
DK (1)	DK208880A (de)
ES (1)	ES8104179A1 (de)
FR (1)	FR2456724A1 (de)
GB (1)	GB2050363B (de)
IE (1)	IE49479B1 (de)
IT (1)	IT1114245B (de)
LU (1)	LU82448A1 (de)
MX (1)	MX6220E (de)
NL (1)	NL8002737A (de)
NO (1)	NO801195L (de)
PT (1)	PT71198A (de)
SE (1)	SE8003496L (de)
ZA (1)	ZA802666B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2204869A (en) *	1987-05-18	1988-11-23	Procter & Gamble	Novel anti-inflammatory esters, pharmaceutical compositions and methods for reducing inflammation
US4912248A (en) *	1987-05-18	1990-03-27	The Procter & Gamble Company	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation

1979
- 1979-05-17 IT IT22738/79A patent/IT1114245B/it active
1980
- 1980-04-24 NO NO801195A patent/NO801195L/no unknown
- 1980-04-30 DE DE3016616A patent/DE3016616C2/de not_active Expired
- 1980-05-02 GB GB8014797A patent/GB2050363B/en not_active Expired
- 1980-05-02 CH CH343580A patent/CH642257A5/it not_active IP Right Cessation
- 1980-05-02 ZA ZA00802666A patent/ZA802666B/xx unknown
- 1980-05-05 AT AT0237680A patent/AT366359B/de not_active IP Right Cessation
- 1980-05-05 AU AU58081/80A patent/AU516763B2/en not_active Ceased
- 1980-05-07 PT PT71198A patent/PT71198A/pt unknown
- 1980-05-09 SE SE8003496A patent/SE8003496L/xx not_active Application Discontinuation
- 1980-05-12 NL NL8002737A patent/NL8002737A/nl not_active Application Discontinuation
- 1980-05-13 IE IE978/80A patent/IE49479B1/en unknown
- 1980-05-13 DK DK208880A patent/DK208880A/da unknown
- 1980-05-14 LU LU82448A patent/LU82448A1/fr unknown
- 1980-05-14 FR FR8010948A patent/FR2456724A1/fr active Granted
- 1980-05-16 MX MX808822U patent/MX6220E/es unknown
- 1980-05-16 JP JP6586680A patent/JPS5625131A/ja active Pending
- 1980-05-16 ES ES491555A patent/ES8104179A1/es not_active Expired
- 1980-05-16 BE BE2/58567A patent/BE883330A/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5625131A (en)	1981-03-10
AU5808180A (en)	1980-11-20
IE49479B1 (en)	1985-10-16
DK208880A (da)	1980-11-18
SE8003496L (sv)	1980-11-18
NL8002737A (nl)	1980-11-19
IE800978L (en)	1980-11-17
MX6220E (es)	1984-12-21
ZA802666B (en)	1981-05-27
GB2050363B (en)	1983-04-27
ES491555A0 (es)	1981-04-01
AU516763B2 (en)	1981-06-18
NO801195L (no)	1980-11-18
DE3016616C2 (de)	1982-09-16
ATA237680A (de)	1981-08-15
AT366359B (de)	1982-04-13
FR2456724B1 (de)	1984-04-20
DE3016616A1 (de)	1980-11-20
PT71198A (en)	1980-06-01
LU82448A1 (fr)	1980-07-31
BE883330A (nl)	1980-09-15
FR2456724A1 (fr)	1980-12-12
ES8104179A1 (es)	1981-04-01
IT1114245B (it)	1986-01-27
IT7922738A0 (it)	1979-05-17
GB2050363A (en)	1981-01-07

Legal Events

Date	Code	Title	Description
1993-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US3385886A (en)	1968-05-28	Phenyl propionic acids
IL23152A (en)	1969-06-25	Alkanoic acids are converted by aryl groups
US4309407A (en)	1982-01-05	Alkenyl-substituted thienylalkanecarboxylic acids and derivatives thereof
CS267551B1 (en)	1990-02-12	Pharmaceutical agents for asthma treatment and method of effective substance production
JPH059424B2 (de)	1993-02-04
US4699925A (en)	1987-10-13	Biphenylylpropionic acid derivative and pharmaceutical composition containing the same
US3402198A (en)	1968-09-17	2-(phenoxy), 2-(phenylthio) and 2-(anilino) substituted 2-alkylideneacetic acid derivatives
US4183954A (en)	1980-01-15	Benzoic acid derivatives and therapeutic composition containing the same
CH642257A5 (it)	1984-04-13	Esteri di 2-(6-metossi-2-naftil)propile, processo per la loro preparazione e composizioni farmaceutiche che li contengono.
JPH0234951B2 (de)	1990-08-07
US5196567A (en)	1993-03-23	Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same
US4440787A (en)	1984-04-03	Compounds with antiinflammatory and analgesic activity, process for the preparation thereof and pharmaceutical compositions therefrom
US3997589A (en)	1976-12-14	4-(2'-Fluoro-4-biphenylylr-4-oxo-butyric acid and esters and salts thereof
JPS6033373B2 (ja)	1985-08-02	１−ナフチル酢酸誘導体、その製造法ならびに１−ナフチル酢酸誘導体を含有する薬剤
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