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 PDFInfo
- Publication number
- LT3604B LT3604B LTIP872A LTIP872A LT3604B LT 3604 B LT3604 B LT 3604B LT IP872 A LTIP872 A LT IP872A LT IP872 A LTIP872 A LT IP872A LT 3604 B LT3604 B LT 3604B
- Authority
- LT
- Lithuania
- Prior art keywords
- formula
- compound
- crr
- alkyl
- pharmaceutically acceptable
- Prior art date
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- 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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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
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- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EA018185B1 (ru) | 2008-03-07 | 2013-06-28 | Ацьенде Кимике Рьюните Анджелини Франческо A.К.P.A.Ф. С.П.А. | Новые производные 1-бензил-3-гидроксиметилиндазола и их применение при лечении заболеваний, обусловленных экспрессией mcp-1 или cx3cr1 |
| DK2254869T3 (en) | 2008-03-07 | 2017-09-04 | Acraf | 1-BENZYL-3-HYDROXYMETHYL INDAZOLE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF DISEASES BASED ON THE EXPRESSION OF CX3CR1 AND P40 |
| 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. |
| BR112012002130A2 (pt) * | 2009-08-03 | 2015-09-15 | Aziende Chimique Riunite Angelini Francesco A C R A F S P A | processo para a preparação de composto,e, composto intermediário |
| UA108742C2 (uk) * | 2009-09-23 | 2015-06-10 | Фармацевтична композиція для лікування запальних захворювань, опосередкованих mcp-1 | |
| US8999292B2 (en) | 2012-05-01 | 2015-04-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| CA3095012C (en) | 2012-05-01 | 2023-02-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| JP2015521183A (ja) | 2012-05-18 | 2015-07-27 | サノフイ | ピリジン誘導体および病理学的血栓形成に関連する状態の治療へのその使用 |
| DK2882715T3 (en) | 2012-05-18 | 2017-02-13 | Sanofi Sa | PYRAZOL DERIVATIVES AND USE THEREOF AS LPAR5 ANTAGONISTS |
| 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 |
| AU2019441740B2 (en) | 2019-04-18 | 2025-12-18 | Tracery Ophthalmics Inc. | Detection, prediction, and classification for ocular disease |
| EP3990433B1 (en) * | 2019-06-25 | 2026-05-20 | Translatum Medicus Inc. | PROCESSES FOR THE MANUFACTURE OF 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 DE DE69021902T patent/DE69021902T2/de not_active Expired - Lifetime
- 1990-01-23 DK DK90200167.6T patent/DK0382276T3/da active
- 1990-01-23 AT AT90200167T patent/ATE127115T1/de not_active IP Right Cessation
- 1990-01-23 ES ES90200167T patent/ES2020171T3/es not_active Expired - Lifetime
- 1990-01-23 DE DE199090200167T patent/DE382276T1/de active Pending
- 1990-01-23 EP EP90200167A patent/EP0382276B1/en not_active Expired - Lifetime
- 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 RO RO144074A patent/RO106252B1/ro unknown
- 1990-02-05 PL PL90285287A patent/PL163730B1/pl unknown
- 1990-02-05 YU YU20690A patent/YU47943B/sh unknown
- 1990-02-06 SK SK563-90A patent/SK278441B6/sk not_active IP Right Cessation
- 1990-02-06 RU SU904743128A patent/RU2066318C1/ru active
- 1990-02-06 FI FI900577A patent/FI102678B1/fi active IP Right Grant
- 1990-02-06 PH PH40002A patent/PH26552A/en unknown
- 1990-02-06 AR AR90316095A patent/AR247386A1/es active
- 1990-02-06 BG BG091122A patent/BG50273A3/xx unknown
- 1990-02-06 EG EG6290A patent/EG19170A/xx active
- 1990-02-06 JP JP2027007A patent/JP2870925B2/ja not_active Expired - Lifetime
- 1990-02-06 CZ CS90563A patent/CZ280121B6/cs not_active IP Right Cessation
- 1990-02-06 PT PT93067A patent/PT93067B/pt active IP Right Grant
- 1990-02-06 UA UA4743128A patent/UA26852C2/uk unknown
- 1990-02-06 HU HU90689A patent/HU204793B/hu unknown
- 1990-02-07 CA CA002009503A patent/CA2009503C/en not_active Expired - Lifetime
- 1990-02-07 KR KR1019900001453A patent/KR0145525B1/ko not_active Expired - Fee Related
- 1990-02-07 DD DD90342349A patent/DD295363A5/de unknown
- 1990-02-07 DD DD90337657A patent/DD291995A5/de unknown
- 1990-02-07 CN CN90100599A patent/CN1046505C/zh not_active Expired - Fee Related
- 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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (2)
| Title |
|---|
| 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 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19980817 |