WO1999059524A2 - Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica - Google Patents
Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica Download PDFInfo
- Publication number
- WO1999059524A2 WO1999059524A2 PCT/ES1999/000142 ES9900142W WO9959524A2 WO 1999059524 A2 WO1999059524 A2 WO 1999059524A2 ES 9900142 W ES9900142 W ES 9900142W WO 9959524 A2 WO9959524 A2 WO 9959524A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- inflammation
- neurogenic inflammation
- treatment
- heteroaryl
- aryl
- Prior art date
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to the use of derivatives of a ⁇ l (or heteroaryl) azol ⁇ lcarb ⁇ nols of general formula (I), as well as their physiologically acceptable salts, in the preparation of medicaments, useful in human and / or veterinary therapeutics, for the treatment of neurogenic inflammation present in different processes such as diabetes, asthma, cystitis, gingivitis, migraine, rhinitis dermatitis, psoriasis, inflammation of sciatic and lumbar nerves, gastrointestinal processes, eye inflammation, etc.
- neurogenic inflammation present in different processes such as diabetes, asthma, cystitis, gingivitis, migraine, rhinitis dermatitis, psoriasis, inflammation of sciatic and lumbar nerves, gastrointestinal processes, eye inflammation, etc.
- Neurogenic inflammation is present in very different pathological conditions, and is characterized by vasodilation and plasma extravasation in areas provided with non-myelinated fibers. Activation of these fibers releases substance P and peptide mediators related to the calcitonin gene ( CGRP) of afferent nerve terminals causing the characteristic symptoms of neurogenic inflammation [GYORFI, A et al, J Clin Pe ⁇ odontol 19 (10) 731-736 (1992)]
- Substance P plays an important role as the main mediator in the induction of neurogenic inflammation through an increase in vascular permeability following the release of histamine from mast cells and by interaction with endothelial cells [INOUE, H et al,
- CGRP can enhance the plasma extravasation induced by substance P in the rat trachea and therefore has an important role in the modulation of neurogenic inflammation in the respiratory tract [BROKAW, JJ et al., Lung 170 (2): 85-93 (1992)].
- Neuropeptides (CGRP and substance P, among others) are found in non-myelinated primary afferent neurons as neurotransmitters [HOLZER, P., Neuroscience 24: 739-768 (1988)].
- Neurogenic inflammations, with reflex vasodilation of the axon, plasma extravasation and edema can be caused by neuropeptides through the activation of primary afferent neurons.
- Ar represents a substituted or unsubstituted benzene ring or a thiophene ring
- R 1 represents a hydrogen atom or a lower alkyl group from Ci to C 4
- R2 represents a dialkylaminoalkyl or azaheterocyclylalkyl radical and Het represents an azol, as well as its physiologically acceptable salts.
- the compounds of general formula (I), as well as their physiologically acceptable salts are especially useful for the preparation of medicaments, useful in human and / or veterinary therapeutics, for the cure or relief of neurogenic inflammation present in Different processes such as: diabetes, asthma, cystitis, gingivitis, migraine, dermatitis, rhinitis, psoriasis, inflammation of the sciatic and lumbar nerves, gastrointestinal processes, eye inflammation, etc.
- the present invention relates to the use of aryl (or heteroaryl) azolylcarbinole derivatives of general formula (I)
- Ar is a phenyl radical or a thienyl radical, unsubstituted or optionally substituted by 1, 2 or 3 identical or different substituents, selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl and methoxy;
- R1 is a hydrogen atom or an alkyl group Ci - C 4;
- R2 is a dialkyl (C ⁇ -C 4 ) amino (C 2 -C 3 ) alkyl, or azaheterocyclyl (C 2 -C 3 ) alkyl radical;
- Y is a dialkyl (C ⁇ -C 4 ) amino (C 2 -C 3 ) alkyl, or azaheterocyclyl (C 2 -C 3 ) alkyl radical;
- Het is a five-membered nitrogen aromatic heterocycle containing one to three nitrogen atoms, unsubstituted or optionally substituted by 1 or 2 equal or different substituents selected from the group consisting of fluorine, chlorine, bromine and methyl; or one of its physiologically acceptable salts, in the development of a drug for the treatment of neurogenic inflammation in mammals, including man
- Ci-C alkyl group represents a straight or branched chain radical derived from a saturated hydrocarbon of 1 to 4 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and ferc-butyl
- d ⁇ alqu ⁇ l (C ⁇ - C 4 ) am ⁇ noalqu ⁇ lo (C 2 - C 3 ) or azaheterocyclylalkyl (C 2 - C 3 ) represents an alkyl radical of two or three carbon atoms attached to a d ⁇ alqu ⁇ l (C ⁇ - C) am ⁇ na or an amine cyclic, such as, for example, dimethylaminoethyl, dimethylaminopropyl, diethylaminoethyl, pipe ⁇ dylethyl, morpholinylpropyl, pyrrolidinylalkyl, etc.
- the compounds of the general formula (I) can be synthesized according to the procedures described in the patents EP 289380 or ES 9800793
- the compounds of the general formula (I) have a stereogenic center and the invention concerns both the use of a pure enantiomer and of a mixture of enantiomers
- the enantiomers can be prepared by any of the procedures described in our patents PCT / EP96 / 05596, ES 9701538, ES 9701728 or ES 9800793
- Pharmaceutical compositions containing compounds of general formula (I) are described in our patents EP 289380 and ES 9800793
- the activity of the compounds of general formula (I) against neurogenic inflammation has been demonstrated by directly studying the effect of these compounds on neurogenic inflammation in determining the inhibition of ear edema induced by mouse capsaicin. has determined the effect on spinal release of substance P and CGRP in rat Finally, the effect on spinal release of CGRP in pohartritic rats has been studied
- mice ear edema was based on the method of Inoue and cois [INOUE, H et al, Br J Pharmacol 110 1614-1620 (1993)]
- capsaicin 250 ⁇ g / 5 ⁇ l ethanol was applied ) on both dorsal and ventral surfaces of the right ear of each mouse (ICR males, 35-45 g)
- capsaicin application the animals were sacrificed by cervical dislocation A 7 mm diameter disc was removed from the tissue of the right ear, using a metallic punch and the weights of said tissue discs were determined.
- Polyartritris was induced by intradermal injection of 0.05 ml of Freund's complete adjuvant (Mycobacterium butiricum suspended in mineral oil), about 3 cm from the base of the Sprague-Dawley rat tail (150-175 g weight). The animals were used four weeks later, when the legs and tail had maximum inflammation. The rest of the test was performed following the same intrathecal perfusion procedure described in Example 2.
- Freund's complete adjuvant Mycobacterium butiricum suspended in mineral oil
- the ( ⁇ ) -5- ⁇ - [2- (dimethylamino) ethoxy] benzyl ⁇ -1-methyl-1 H-pyrazole citrate was administered via i.p. at the dose of 46 mg / kg and the intrathecal release of CGRP was determined for 3 hours.
- the comparison with the control group showed that the release of CGRP was much lower in the group treated with ( ⁇ ) -5- ⁇ - [2- (dimethylamino) ethoxy] benzyl ⁇ -1-methyl-1 H-pyrazole .
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ508316A NZ508316A (en) | 1998-05-18 | 1999-01-13 | A treatment for neurogenic inflammation in a variety of pathological conditions involving the activation of non-myelinated nerve fibres |
KR1020007012955A KR100572416B1 (ko) | 1998-05-18 | 1999-05-18 | 신경원성 질환의 치료를 위한 약물의 제조에 사용되는아릴(또는 헤테로아릴) 아졸일카르비놀 유도체 |
CA002332711A CA2332711A1 (en) | 1998-05-18 | 1999-05-18 | Use of derivatives of aryl(or heteroaryl)azolylcarbinols in the manufacture of a medicament for the treatment of neurogenic inflammation |
EP99919290A EP1086682B1 (en) | 1998-05-18 | 1999-05-18 | Utilization of aryl(or heteroaryl)azolylcarbinol derivatives in the preparation of a medicament for the treatment of neurogenic inflammation |
IL13974498A IL139744A0 (en) | 1998-05-18 | 1999-05-18 | Use of derivates of aryl (or heteroaryl) azolycarbinols in the manufacture of a medicament for the treatment of neurogenic inflamation |
DK99919290T DK1086682T3 (da) | 1998-05-18 | 1999-05-18 | Anvendelse af aryl(eller heteroaryl)azolylcarbinolderivater ved fremstilling af et lægemiddel til behandling af neurogen betændelse |
BR9910587-0A BR9910587A (pt) | 1998-05-18 | 1999-05-18 | Uso de derivados de aril(ou heteroaril) azolilcarbinóis na fabricacão de um medicamento para tratamento de inflamação neurogênica |
JP2000549190A JP2002515409A (ja) | 1998-05-18 | 1999-05-18 | 神経性炎症の治療のための薬の製造におけるアリール(又はヘテロアリール)アゾリルカルビノール誘導体の使用 |
HU0102112A HUP0102112A3 (en) | 1998-05-18 | 1999-05-18 | Utilization of aryl(or heteroaryl)azolylcarbinol derivatives in the preparation of a medicament for the treatment of neurogenic inflammation |
AU37118/99A AU759229B2 (en) | 1998-05-18 | 1999-05-18 | Utilization of aryl(or heteroaryl)azolylcarbinol derivatives in the preparation of a medicament for the treatment of neurogenic inflammation |
DE69906969T DE69906969T2 (de) | 1998-05-18 | 1999-05-18 | Verwendung von aryl(oder heteroaryl)-azolylcarbinolderivaten in der herstellung von medikamenten zur behandlung von neurogenen entzündungen |
PL99344742A PL344742A1 (en) | 1998-05-18 | 1999-05-18 | Utilization of aryl(or heteroaryl)azolylcarbinol derivatives in the preparation of a medicament for the treatment of neurogenic inflammation |
ES99919290T ES2196800T3 (es) | 1998-05-18 | 1999-05-18 | Usos de derivados de aril (oheteroaril) azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion nueurogenica. |
AT99919290T ATE237328T1 (de) | 1998-05-18 | 1999-05-18 | Verwendung von aryl(oder heteroaryl)- azolylcarbinolderivaten in der herstellung von medikamenten zur behandlung von neurogenen entzündungen |
IL139744A IL139744A (en) | 1998-05-18 | 2000-11-17 | Use of derivatives of aryl or troaryl azolylcarbinols in the manufacture of a drug for the treatment of neurogenic inflammation |
NO20005837A NO20005837L (no) | 1998-05-18 | 2000-11-17 | Anvendelse av aryl (eller heteroaryl) azolylkarbinolderivater ved fremstilling av et medikament for behandling av neurogen inflammasjon |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES009801021A ES2137136B1 (es) | 1998-05-18 | 1998-05-18 | Empleo de derivados de aril (o heteroaril) azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica. |
ESP9801021 | 1998-05-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1999059524A2 true WO1999059524A2 (es) | 1999-11-25 |
WO1999059524A3 WO1999059524A3 (es) | 2000-03-09 |
Family
ID=8303801
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1999/000142 WO1999059524A2 (es) | 1998-05-18 | 1999-05-18 | Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica |
Country Status (24)
Country | Link |
---|---|
EP (1) | EP1086682B1 (es) |
JP (1) | JP2002515409A (es) |
KR (1) | KR100572416B1 (es) |
CN (1) | CN1221257C (es) |
AR (1) | AR019555A1 (es) |
AT (1) | ATE237328T1 (es) |
AU (1) | AU759229B2 (es) |
BR (1) | BR9910587A (es) |
CA (1) | CA2332711A1 (es) |
CZ (1) | CZ291593B6 (es) |
DE (1) | DE69906969T2 (es) |
DK (1) | DK1086682T3 (es) |
ES (2) | ES2137136B1 (es) |
HU (1) | HUP0102112A3 (es) |
IL (2) | IL139744A0 (es) |
NO (1) | NO20005837L (es) |
NZ (1) | NZ508316A (es) |
PL (1) | PL344742A1 (es) |
PT (1) | PT1086682E (es) |
RU (1) | RU2212237C2 (es) |
TR (1) | TR200003434T2 (es) |
TW (1) | TW570796B (es) |
WO (1) | WO1999059524A2 (es) |
ZA (1) | ZA200006732B (es) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2150353B1 (es) * | 1998-04-15 | 2001-07-01 | Esteve Labor Dr | Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos. |
ES2174756B2 (es) * | 2001-04-06 | 2003-11-16 | Esteve Labor Dr | Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de enfermedades respiratorias. |
ES2180449B1 (es) * | 2001-07-06 | 2004-01-16 | Esteve Labor Dr | Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de la incontinencia urinaria. |
CA2495498C (en) * | 2002-08-12 | 2014-04-15 | Birkir Sveinsson | Use of cgrp antagonist compounds for treatment of psoriasis |
EP1784178A1 (en) * | 2004-07-30 | 2007-05-16 | Laboratorios Del Dr. Esteve, S.A. | Aryl (or heteroaryl) azolylcarbinols |
EP1632227A1 (en) * | 2004-09-07 | 2006-03-08 | Laboratorios del Dr. Esteve S.A. | Derivatives of aryl (or heteroaryl) azolylcarbinols (in particular cizolirtin citrate) for the treatment of opioid addiction |
EP1820502A1 (en) * | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0289380A1 (fr) * | 1987-04-10 | 1988-11-02 | Laboratorios Del Dr. Esteve, S.A. | Dérivés d'aryl-hétéroaryl carbinols avec activité analgésique |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2681322B1 (fr) * | 1991-09-12 | 1993-12-17 | Laboratorios Dr Esteve Sa | Derives d'aryl-heteroaryl-{n-[2-(3,4-dimethoxyphenyl)-ethyl]-n-methyl-3-aminopropoxy}-methane leur preparation et leur application en tant que medicaments . |
ES2150353B1 (es) * | 1998-04-15 | 2001-07-01 | Esteve Labor Dr | Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos. |
-
1998
- 1998-05-18 ES ES009801021A patent/ES2137136B1/es not_active Expired - Fee Related
-
1999
- 1999-01-13 NZ NZ508316A patent/NZ508316A/en unknown
- 1999-05-14 AR ARP990102325A patent/AR019555A1/es unknown
- 1999-05-18 CA CA002332711A patent/CA2332711A1/en not_active Abandoned
- 1999-05-18 IL IL13974498A patent/IL139744A0/xx not_active IP Right Cessation
- 1999-05-18 HU HU0102112A patent/HUP0102112A3/hu unknown
- 1999-05-18 CZ CZ20004282A patent/CZ291593B6/cs not_active IP Right Cessation
- 1999-05-18 PT PT99919290T patent/PT1086682E/pt unknown
- 1999-05-18 JP JP2000549190A patent/JP2002515409A/ja active Pending
- 1999-05-18 AU AU37118/99A patent/AU759229B2/en not_active Ceased
- 1999-05-18 ES ES99919290T patent/ES2196800T3/es not_active Expired - Lifetime
- 1999-05-18 WO PCT/ES1999/000142 patent/WO1999059524A2/es active IP Right Grant
- 1999-05-18 BR BR9910587-0A patent/BR9910587A/pt not_active Application Discontinuation
- 1999-05-18 RU RU2000131615/14A patent/RU2212237C2/ru not_active IP Right Cessation
- 1999-05-18 DE DE69906969T patent/DE69906969T2/de not_active Expired - Fee Related
- 1999-05-18 CN CNB998077216A patent/CN1221257C/zh not_active Expired - Fee Related
- 1999-05-18 TR TR2000/03434T patent/TR200003434T2/xx unknown
- 1999-05-18 PL PL99344742A patent/PL344742A1/xx not_active Application Discontinuation
- 1999-05-18 DK DK99919290T patent/DK1086682T3/da active
- 1999-05-18 KR KR1020007012955A patent/KR100572416B1/ko not_active IP Right Cessation
- 1999-05-18 AT AT99919290T patent/ATE237328T1/de not_active IP Right Cessation
- 1999-05-18 EP EP99919290A patent/EP1086682B1/en not_active Expired - Lifetime
- 1999-05-24 TW TW088108432A patent/TW570796B/zh not_active IP Right Cessation
-
2000
- 2000-11-17 IL IL139744A patent/IL139744A/en unknown
- 2000-11-17 NO NO20005837A patent/NO20005837L/no not_active Application Discontinuation
- 2000-11-17 ZA ZA200006732A patent/ZA200006732B/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0289380A1 (fr) * | 1987-04-10 | 1988-11-02 | Laboratorios Del Dr. Esteve, S.A. | Dérivés d'aryl-hétéroaryl carbinols avec activité analgésique |
Non-Patent Citations (2)
Title |
---|
HUESO-RODRIGUEZ J.A. ET AL.: 'Preparation of the enantiomers of the analgesic E-3710' BIOORGANIC & MEDICINAL CHEMISTRY LETTERS vol. 3, no. 2, 1993, pages 269 - 272 * |
MATTIOLI F. AND GUIA M.: 'W-Dialkylamino alkyl Ethers of Phenyl-(5-substituted 1-phenyl-1H-pyrazol-4-yl) methanols with Analgesic and Anti-inflammatory Activity' J. HETEROCYCLIC CHEM. vol. 34, 1997, pages 963 - 968 * |
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