LT3604B - Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids - Google Patents

Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids Download PDF

Info

Publication number: LT3604B
Authority: LT; Lithuania
Prior art keywords: formula; compound; crr; alkyl; pharmaceutically acceptable
Prior art date: 1989-02-07

Application number

LTIP872A

Other languages

English (en)

Lithuanian (lt)

Inventor

Bruno Silvestrini

Leandro Baiocchi

Original Assignee

Acraf

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.)

1989-02-07

Filing date

1993-08-17

Publication date

1995-12-27

1993-08-17 Application filed by Acraf filed Critical Acraf

1995-03-27 Publication of LTIP872A publication Critical patent/LTIP872A/xx

1995-12-27 Publication of LT3604B publication Critical patent/LT3604B/lt

Links

AKQDXNFPEFHRLS-UHFFFAOYSA-N (1-benzylindazol-3-yl)methanol Chemical compound C12=CC=CC=C2C(CO)=NN1CC1=CC=CC=C1 AKQDXNFPEFHRLS-UHFFFAOYSA-N 0.000 title description 11
150000002170 ethers Chemical class 0.000 title description 5
125000001931 aliphatic group Chemical group 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
-1 1-benzylindazol-3-yl ring Chemical group 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
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238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
DOWQIXLLOPHPRO-UHFFFAOYSA-N methyl 2-ethyl-2-hydroxybutanoate Chemical compound CCC(O)(CC)C(=O)OC DOWQIXLLOPHPRO-UHFFFAOYSA-N 0.000 description 1
DDMCDMDOHABRHD-UHFFFAOYSA-N methyl 2-hydroxybutanoate Chemical compound CCC(O)C(=O)OC DDMCDMDOHABRHD-UHFFFAOYSA-N 0.000 description 1
IJQZYNRJICMGLS-UHFFFAOYSA-N methyl 2-hydroxyhexanoate Chemical compound CCCCC(O)C(=O)OC IJQZYNRJICMGLS-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000013021 overheating Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
229960001153 serine Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000009966 trimming Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
229960004295 valine Drugs 0.000 description 1
239000004474 valine Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- 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
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic 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]

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Rheumatology (AREA)
Neurosurgery (AREA)
Ophthalmology & Optometry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

LTIP872A 1989-02-07 1993-08-17 Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids LT3604B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8947620A IT1230441B (it)	1989-02-07	1989-02-07	Eteri della serie dell'indazolo

Publications (2)

Publication Number	Publication Date
LTIP872A LTIP872A (en)	1995-03-27
LT3604B true LT3604B (en)	1995-12-27

Family

ID=11261479

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP872A LT3604B (en)	1989-02-07	1993-08-17	Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids

Country Status (36)

Country	Link
US (2)	US4999367A (ko)
EP (1)	EP0382276B1 (ko)
JP (1)	JP2870925B2 (ko)
KR (1)	KR0145525B1 (ko)
CN (2)	CN1046505C (ko)
AR (1)	AR247386A1 (ko)
AT (1)	ATE127115T1 (ko)
AU (1)	AU624895B2 (ko)
BG (1)	BG50273A3 (ko)
CA (1)	CA2009503C (ko)
CZ (1)	CZ280121B6 (ko)
DD (2)	DD295363A5 (ko)
DE (2)	DE382276T1 (ko)
DK (1)	DK0382276T3 (ko)
EG (1)	EG19170A (ko)
ES (1)	ES2020171T3 (ko)
FI (1)	FI102678B (ko)
GE (1)	GEP19971030B (ko)
GR (2)	GR910300073T1 (ko)
HU (1)	HU204793B (ko)
IL (1)	IL93132A (ko)
IN (1)	IN170957B (ko)
IT (1)	IT1230441B (ko)
LT (1)	LT3604B (ko)
LV (1)	LV10612B (ko)
NZ (1)	NZ232258A (ko)
PE (1)	PE25091A1 (ko)
PH (1)	PH26552A (ko)
PL (2)	PL163720B1 (ko)
PT (1)	PT93067B (ko)
RO (1)	RO106252B1 (ko)
RU (3)	RU2066318C1 (ko)
SK (1)	SK278441B6 (ko)
UA (1)	UA26852C2 (ko)
YU (1)	YU47943B (ko)
ZA (1)	ZA90644B (ko)

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IT1253703B (it) *	1991-04-22	1995-08-23	Angelini Francesco Ist Ricerca	Uso di acidi metossi alcanoici dell'indazolo per preparare un farmaco attivo nel trattamento di malattie autoimmunitarie
IT1293795B1 (it) *	1997-07-28	1999-03-10	Angelini Ricerche Spa	Farmaco attivo nel ridurre la produzione di proteina mcp-1
US5943270A (en) *	1997-11-26	1999-08-24	Intel Corporation	Two-transistor DRAM cell for logic process technology
US7514463B2 (en)	2004-08-20	2009-04-07	University Of Kansas	Lonidamine analogues and their use in male contraception and cancer treatment
ITMI20062254A1 (it)	2006-11-24	2008-05-25	Acraf	Uso di un acido metossi-alcanoico dell'indazolo per preparare una composizione farmaceutca
PT2254869T (pt)	2008-03-07	2017-07-18	Acraf	Novos derivados de 1-benzil-3-hidroximetilindazole e suas utilizações no tratamento de doenças com base na expressão de cx3cr1 e p40
AU2009221063B2 (en)	2008-03-07	2013-03-21	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.	1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, and CX3CR1
MX2010009625A (es)	2008-03-07	2010-09-28	Acraf	Derivados de 1-bencil-3-hidroximetilindazol y uso de los mismos en el tratamiento de enfermedades basadas en la expresion de mcp-1, cx3cr1 y p40.
CA2766235C (en)	2009-08-03	2017-04-04	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F.S.P.A.	Process for the preparation of 1-benzyl-3-hydroxymethyl-1h-indazole and its derivatives and required magnesium intermediates
UA108742C2 (uk)	2009-09-23	2015-06-10		Фармацевтична композиція для лікування запальних захворювань, опосередкованих mcp-1
JP2015523546A (ja)	2012-05-01	2015-08-13	トランスレイタムメディカスインコーポレイテッド	失明性疾患を処置および診断するための方法
US8999292B2 (en)	2012-05-01	2015-04-07	Translatum Medicus Inc.	Methods for treating and diagnosing blinding eye diseases
EP2850062B1 (en)	2012-05-18	2017-07-19	Sanofi	Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation
JP6257596B2 (ja)	2012-05-18	2018-01-10	サノフイ	ピラゾール誘導体およびｌｐａｒ５アンタゴニストとしてのその使用
CN108047136B (zh) *	2017-12-20	2021-07-09	长春普华制药股份有限公司	一种苄达酸的精制方法
US11753382B2 (en)	2019-06-25	2023-09-12	Translatum Medicus Inc.	Processes of making 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid and its derivatives
CN113929627A (zh) *	2021-10-19	2022-01-14	吕梁学院	一种宾达利的合成方法

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US3470194A (en)	1966-08-29	1969-09-30	Acraf	(indazole-3-yl)-oxyalkanoic acids
US4352813A (en)	1980-07-29	1982-10-05	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.	[(1-Benzyl-1H-indazol-3-yl)oxy] acetic acid salt with L. lysine
US4451477A (en)	1981-11-27	1984-05-29	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.	Bendazac treatment of cataract
EP0131317A2 (en)	1983-04-18	1985-01-16	AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.	Use of Benzadac and of its salts for the manufacture of a medicament for the treatment of retinitis pigmentosa
EP0255967A1 (en)	1986-08-01	1988-02-17	AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.	Method of treating contact lenses

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US3470298A (en) *	1969-01-29	1969-09-30	Acraf	Topical anti-inflammatory composition containing (indazole-3-yl)-oxyalkanoic acids

1989
- 1989-02-07 IT IT8947620A patent/IT1230441B/it active
1990
- 1990-01-22 IL IL9313290A patent/IL93132A/en not_active IP Right Cessation
- 1990-01-23 ES ES90200167T patent/ES2020171T3/es not_active Expired - Lifetime
- 1990-01-23 AT AT90200167T patent/ATE127115T1/de not_active IP Right Cessation
- 1990-01-23 EP EP90200167A patent/EP0382276B1/en not_active Expired - Lifetime
- 1990-01-23 DE DE199090200167T patent/DE382276T1/de active Pending
- 1990-01-23 DE DE69021902T patent/DE69021902T2/de not_active Expired - Lifetime
- 1990-01-23 DK DK90200167.6T patent/DK0382276T3/da active
- 1990-01-24 US US07/470,118 patent/US4999367A/en not_active Expired - Lifetime
- 1990-01-26 NZ NZ232258A patent/NZ232258A/en unknown
- 1990-01-29 ZA ZA90644A patent/ZA90644B/xx unknown
- 1990-01-30 PE PE1990164654A patent/PE25091A1/es unknown
- 1990-01-30 IN IN81/CAL/90A patent/IN170957B/en unknown
- 1990-02-02 AU AU49066/90A patent/AU624895B2/en not_active Expired
- 1990-02-05 PL PL90283638A patent/PL163720B1/pl unknown
- 1990-02-05 YU YU20690A patent/YU47943B/sh unknown
- 1990-02-05 RO RO144074A patent/RO106252B1/ro unknown
- 1990-02-05 PL PL90285287A patent/PL163730B1/pl unknown
- 1990-02-06 RU SU904743128A patent/RU2066318C1/ru active
- 1990-02-06 FI FI900577A patent/FI102678B/fi active IP Right Grant
- 1990-02-06 AR AR90316095A patent/AR247386A1/es active
- 1990-02-06 EG EG6290A patent/EG19170A/xx active
- 1990-02-06 HU HU90689A patent/HU204793B/hu unknown
- 1990-02-06 PT PT93067A patent/PT93067B/pt active IP Right Grant
- 1990-02-06 SK SK563-90A patent/SK278441B6/sk not_active IP Right Cessation
- 1990-02-06 JP JP2027007A patent/JP2870925B2/ja not_active Expired - Lifetime
- 1990-02-06 PH PH40002A patent/PH26552A/en unknown
- 1990-02-06 UA UA4743128A patent/UA26852C2/uk unknown
- 1990-02-06 CZ CS90563A patent/CZ280121B6/cs not_active IP Right Cessation
- 1990-02-06 BG BG091122A patent/BG50273A3/xx unknown
- 1990-02-07 DD DD90342349A patent/DD295363A5/de unknown
- 1990-02-07 KR KR1019900001453A patent/KR0145525B1/ko not_active IP Right Cessation
- 1990-02-07 DD DD90337657A patent/DD291995A5/de unknown
- 1990-02-07 CN CN90100599A patent/CN1046505C/zh not_active Expired - Fee Related
- 1990-02-07 CA CA002009503A patent/CA2009503C/en not_active Expired - Lifetime
- 1990-12-20 US US07/632,117 patent/US5112986A/en not_active Expired - Lifetime
1991
- 1991-06-05 RU SU914895526A patent/RU2055071C1/ru active
- 1991-06-05 RU SU914895540A patent/RU2044729C1/ru active
- 1991-11-15 GR GR91300073T patent/GR910300073T1/el unknown
1993
- 1993-06-22 LV LVP-93-647A patent/LV10612B/lv unknown
- 1993-07-26 GE GEAP19931214A patent/GEP19971030B/en unknown
- 1993-08-17 LT LTIP872A patent/LT3604B/lt not_active IP Right Cessation
- 1993-09-15 CN CN93117740A patent/CN1034016C/zh not_active Expired - Fee Related
1995
- 1995-11-22 GR GR950403284T patent/GR3018165T3/el unknown

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US3470194A (en)	1966-08-29	1969-09-30	Acraf	(indazole-3-yl)-oxyalkanoic acids
US4352813A (en)	1980-07-29	1982-10-05	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.	[(1-Benzyl-1H-indazol-3-yl)oxy] acetic acid salt with L. lysine
US4451477A (en)	1981-11-27	1984-05-29	Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.	Bendazac treatment of cataract
EP0131317A2 (en)	1983-04-18	1985-01-16	AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.	Use of Benzadac and of its salts for the manufacture of a medicament for the treatment of retinitis pigmentosa
EP0255967A1 (en)	1986-08-01	1988-02-17	AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.	Method of treating contact lenses

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J. MARCH: "Advanced Organic Chemistry"
WOOLFE G, MACDONALD AD: "The evaluation of the analgesic action of pethidine hydrochloride", J PHARMACOL EXPER THER, 1944, pages 300 - 307

Also Published As

Publication number	Publication date
EP0382276A3 (en)	1990-12-12
LTIP872A (en)	1995-03-27
AU4906690A (en)	1990-08-16
CN1044810A (zh)	1990-08-22
PL163730B1 (pl)	1994-04-29
GR910300073T1 (en)	1991-11-15
GR3018165T3 (en)	1996-02-29
JP2870925B2 (ja)	1999-03-17
SK56390A3 (en)	1997-05-07
IT1230441B (it)	1991-10-23
RU2066318C1 (ru)	1996-09-10
CN1034016C (zh)	1997-02-12
HU204793B (en)	1992-02-28
LV10612B (en)	1995-08-20
KR0145525B1 (ko)	1998-08-17
IT8947620A0 (it)	1989-02-07
FI900577A0 (fi)	1990-02-06
EP0382276A2 (en)	1990-08-16
ES2020171A4 (es)	1991-08-01
CA2009503C (en)	2000-04-11
IL93132A0 (en)	1990-11-05
US5112986A (en)	1992-05-12
DD291995A5 (de)	1991-07-18
ES2020171T3 (es)	1995-12-01
JPH02240065A (ja)	1990-09-25
IL93132A (en)	1994-05-30
PH26552A (en)	1992-08-19
RO106252B1 (ro)	1993-03-31
RU2055071C1 (ru)	1996-02-27
HUT53088A (en)	1990-09-28
CA2009503A1 (en)	1990-08-07
CN1046505C (zh)	1999-11-17
US4999367A (en)	1991-03-12
DE382276T1 (de)	1991-11-28
KR900012913A (ko)	1990-09-03
FI102678B1 (fi)	1999-01-29
GEP19971030B (en)	1997-06-13
EP0382276B1 (en)	1995-08-30
YU20690A (sh)	1992-07-20
NZ232258A (en)	1991-06-25
CZ56390A3 (en)	1995-06-14
SK278441B6 (en)	1997-05-07
DK0382276T3 (da)	1996-01-15
ATE127115T1 (de)	1995-09-15
RU2044729C1 (ru)	1995-09-27
PE25091A1 (es)	1991-08-17
AU624895B2 (en)	1992-06-25
UA26852C2 (uk)	1999-12-29
CN1088201A (zh)	1994-06-22
AR247386A1 (es)	1994-12-29
PT93067A (pt)	1990-08-31
LV10612A (lv)	1995-04-20
DD295363A5 (de)	1991-10-31
HU900689D0 (en)	1990-04-28
DE69021902T2 (de)	1996-05-23
DE69021902D1 (de)	1995-10-05
IN170957B (ko)	1992-06-20
YU47943B (sh)	1996-07-24
CZ280121B6 (cs)	1995-11-15
ZA90644B (en)	1991-01-30
PT93067B (pt)	1995-12-29
BG50273A3 (en)	1992-06-15
PL163720B1 (pl)	1994-04-29
EG19170A (en)	1994-11-30
FI102678B (fi)	1999-01-29

Publication	Publication Date	Title
LT3604B (en)	1995-12-27	Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids
CZ278011B6 (en)	1993-07-14	Diaryl acetylenes and process for preparing thereof
KR0168046B1 (ko)	1999-03-20	페닐히드라존, 이들의 제조방법 및 이들로부터 제조된 치료 및 미용 조성물
JPH0449533B2 (ko)	1992-08-11
EP1322593A1 (de)	2003-07-02	O-substituierte 6-methyl-tramadol-derivate
EP0051514B1 (fr)	1983-11-23	Dérivé d'acide cinnamoyl-cinnamique, son procédé de préparation et son application en thérapeutique
AU1359692A (en)	1992-10-21	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
JP4541879B2 (ja)	2010-09-08	ケイ皮酸二量体、その製造方法及び退行性脳疾患治療のためのその用途
BRPI0716830A2 (pt)	2013-11-05	Composto, composição, uso de um composto, métodos de contracepção, de terapia de reposição hormonal, de tratar um distúrbio ginecológico, e de produzir um composto
US4026925A (en)	1977-05-31	Active derivatives of methylamine, therapeutic compositions containing the same and processes for preparing the said derivatives and compositions
SE447899B (sv)	1986-12-22	Vattenlosliga derivat av 6,6'-metylen-bis(2,2,4-trimetyl-1,2-dihydrokinolin), sett for deras framstellning samt farmaceutisk beredning innehallande dem.
US2293875A (en)	1942-08-25	Amino compound
SI9010206A (sl)	1998-06-30	Etri 1-benzil-3-hidroksimetil-indazola z alifatskimi 2-hidroksi kislinami
JPH0212938B2 (ko)	1990-03-30
JP2008515958A (ja)	2008-05-15	治療用途または化粧品用途のための二芳香族化合物

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Date	Code	Title	Description
1999-03-25	MM9A	Lapsed patents	Effective date: 19980817