LU82448A1 - Esters de 2-(6-methoxy-2-naphtyl)-1-propanol,leur procede de preparation et leur application en therapeutique - Google Patents

Esters de 2-(6-methoxy-2-naphtyl)-1-propanol,leur procede de preparation et leur application en therapeutique Download PDF

Info

Publication number: LU82448A1
Authority: LU; Luxembourg
Prior art keywords: ena; activity; methoxy; naproxen; hours
Prior art date: 1979-05-17

Application number

LU82448A

Other languages

English (en)

French (fr)

Inventor

R 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

1980-05-14

Publication date

1980-07-31

1980-05-14 Application filed by Mediolanum Farmaceutici Srl filed Critical Mediolanum Farmaceutici Srl

1980-07-31 Publication of LU82448A1 publication Critical patent/LU82448A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 title description 4
230000001225 therapeutic effect Effects 0.000 title description 2
-1 2- (6-Methoxy-2-naphthyl) propanol ester Chemical class 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 15
LTRANDSQVZFZDG-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propan-1-ol Chemical compound C1=C(C(C)CO)C=CC2=CC(OC)=CC=C21 LTRANDSQVZFZDG-UHFFFAOYSA-N 0.000 claims description 6
230000003110 anti-inflammatory effect Effects 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
230000008569 process Effects 0.000 claims description 5
230000003356 anti-rheumatic effect Effects 0.000 claims description 3
239000003435 antirheumatic agent Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
230000001760 anti-analgesic effect Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims 1
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 33
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 33
229960002009 naproxen Drugs 0.000 description 33
230000000694 effects Effects 0.000 description 29
241000700159 Rattus Species 0.000 description 15
238000011282 treatment Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
241001465754 Metazoa Species 0.000 description 11
238000005303 weighing Methods 0.000 description 9
229920002134 Carboxymethyl cellulose Polymers 0.000 description 8
206010030113 Oedema Diseases 0.000 description 8
206010037660 Pyrexia Diseases 0.000 description 8
210000003754 fetus Anatomy 0.000 description 8
241000283973 Oryctolagus cuniculus Species 0.000 description 7
239000001768 carboxy methyl cellulose Substances 0.000 description 7
235000010948 carboxy methyl cellulose Nutrition 0.000 description 7
239000008112 carboxymethyl-cellulose Substances 0.000 description 7
230000000202 analgesic effect Effects 0.000 description 6
230000001754 anti-pyretic effect Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000829 suppository Substances 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000012074 organic phase Substances 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000001154 acute effect Effects 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
230000035935 pregnancy Effects 0.000 description 3
230000009467 reduction Effects 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
206010070863 Toxicity to various agents Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000027950 fever generation Effects 0.000 description 2
235000013305 food Nutrition 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
231100001231 less toxic Toxicity 0.000 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 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
229940090181 propyl acetate Drugs 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000009103 reabsorption Effects 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
230000001562 ulcerogenic effect Effects 0.000 description 2
210000004291 uterus Anatomy 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
NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
YILMTSOAXCYCSL-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)propan-1-ol Chemical compound C1=C(OC)C=CC2=CC(C(O)CC)=CC=C21 YILMTSOAXCYCSL-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
208000037157 Azotemia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
206010018473 Glycosuria 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
ZTCLCSCHTACERP-AWEZNQCLSA-N N-[(1S)-1-[3-chloro-5-fluoro-2-[[2-methyl-4-(2-methyl-1,2,4-triazol-3-yl)quinolin-8-yl]oxymethyl]phenyl]ethyl]-2-(difluoromethoxy)acetamide Chemical compound C1=C(C=C(C(=C1Cl)COC1=CC=CC2=C(C=3N(N=CN=3)C)C=C(C)N=C12)[C@@H](NC(=O)COC(F)F)C)F ZTCLCSCHTACERP-AWEZNQCLSA-N 0.000 description 1
206010058667 Oral toxicity Diseases 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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 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
239000002253 acid 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
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical group 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
239000002221 antipyretic Substances 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
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000008859 change Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000003902 lesion 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
239000000463 material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000001624 naphthyl group Chemical group 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
231100000418 oral toxicity Toxicity 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
201000001474 proteinuria Diseases 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
239000008117 stearic acid Substances 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
231100000048 toxicity data Toxicity 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
239000013585 weight reducing agent Substances 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)

LU82448A 1979-05-17 1980-05-14 Esters de 2-(6-methoxy-2-naphtyl)-1-propanol,leur procede de preparation et leur application en therapeutique LU82448A1 (fr)

Applications Claiming Priority (2)

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
IT2273879		1979-05-17

Publications (1)

Publication Number	Publication Date
LU82448A1 true LU82448A1 (fr)	1980-07-31

Family

ID=11199868

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82448A LU82448A1 (fr)	1979-05-17	1980-05-14	Esters de 2-(6-methoxy-2-naphtyl)-1-propanol,leur procede de preparation et leur application en therapeutique

Country Status (19)

Country	Link
JP (1)	JPS5625131A (es)
AT (1)	AT366359B (es)
AU (1)	AU516763B2 (es)
BE (1)	BE883330A (es)
CH (1)	CH642257A5 (es)
DE (1)	DE3016616C2 (es)
DK (1)	DK208880A (es)
ES (1)	ES491555A0 (es)
FR (1)	FR2456724A1 (es)
GB (1)	GB2050363B (es)
IE (1)	IE49479B1 (es)
IT (1)	IT1114245B (es)
LU (1)	LU82448A1 (es)
MX (1)	MX6220E (es)
NL (1)	NL8002737A (es)
NO (1)	NO801195L (es)
PT (1)	PT71198A (es)
SE (1)	SE8003496L (es)
ZA (1)	ZA802666B (es)

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 ZA ZA00802666A patent/ZA802666B/xx unknown
- 1980-05-02 GB GB8014797A patent/GB2050363B/en not_active Expired
- 1980-05-02 CH CH343580A patent/CH642257A5/it not_active IP Right Cessation
- 1980-05-05 AU AU58081/80A patent/AU516763B2/en not_active Ceased
- 1980-05-05 AT AT0237680A patent/AT366359B/de not_active IP Right Cessation
- 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/ES491555A0/es active Granted
- 1980-05-16 BE BE2/58567A patent/BE883330A/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2050363B (en)	1983-04-27
MX6220E (es)	1984-12-21
ES8104179A1 (es)	1981-04-01
PT71198A (en)	1980-06-01
AT366359B (de)	1982-04-13
IE49479B1 (en)	1985-10-16
CH642257A5 (it)	1984-04-13
FR2456724B1 (es)	1984-04-20
NO801195L (no)	1980-11-18
ES491555A0 (es)	1981-04-01
BE883330A (nl)	1980-09-15
ATA237680A (de)	1981-08-15
NL8002737A (nl)	1980-11-19
DK208880A (da)	1980-11-18
IT1114245B (it)	1986-01-27
DE3016616C2 (de)	1982-09-16
IE800978L (en)	1980-11-17
GB2050363A (en)	1981-01-07
AU516763B2 (en)	1981-06-18
SE8003496L (sv)	1980-11-18
AU5808180A (en)	1980-11-20
DE3016616A1 (de)	1980-11-20
ZA802666B (en)	1981-05-27
IT7922738A0 (it)	1979-05-17
JPS5625131A (en)	1981-03-10
FR2456724A1 (fr)	1980-12-12

Publication	Publication Date	Title
EP0024960A2 (fr)	1981-03-11	Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux
FR2634766A1 (fr)	1990-02-02	Acides (rs)-2-(2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurannyl)-acetiques, et acides 2-(2,3-dihydro-5-acyloxy-4,6,7-trimethylbenzofurannyl)-acetiques et leurs esters, utiles comme medicaments mucoregulateurs et anti-ischemiques, procede pour leur preparation et compositions pharmaceutiques les contenant
LU82448A1 (fr)	1980-07-31	Esters de 2-(6-methoxy-2-naphtyl)-1-propanol,leur procede de preparation et leur application en therapeutique
US7005539B2 (en)	2006-02-28	Ferulic acid dimers and their pharmaceutically acceptable salts, their preparation and use thereof for treating dementia
CH631157A5 (fr)	1982-07-30	Derives d'acide benzoique, leur procede de preparation et leur application therapeutique.
FR2509725A1 (fr)	1983-01-21	(hydroxyalkyl)phenylsulfures, leurs procedes de preparation et compositions pharmaceutiques les contenant
CA2487165C (en)	2010-09-21	Cinnamic acid dimers, their preparation and the use thereof for treating neurodegenerative disease
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