TWI221839B - 6-hydroxy-indazole derivatives for treating glaucoma - Google Patents
6-hydroxy-indazole derivatives for treating glaucoma Download PDFInfo
- Publication number
- TWI221839B TWI221839B TW089125127A TW89125127A TWI221839B TW I221839 B TWI221839 B TW I221839B TW 089125127 A TW089125127 A TW 089125127A TW 89125127 A TW89125127 A TW 89125127A TW I221839 B TWI221839 B TW I221839B
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- Prior art keywords
- hydrogen
- alkyl
- halogen
- individually selected
- scope
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- 208000010412 Glaucoma Diseases 0.000 title claims abstract description 15
- NUYZVDBIVNOTSC-UHFFFAOYSA-N 1H-indazol-6-ol Chemical class OC1=CC=C2C=NNC2=C1 NUYZVDBIVNOTSC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- -1 C1-6alkylsulfoxyl Chemical group 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 238000011049 filling Methods 0.000 claims description 19
- 230000002079 cooperative effect Effects 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000004493 normal intraocular pressure Effects 0.000 claims description 5
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- PNHDUSKIMUKQDR-UHFFFAOYSA-N 1-(3-chloro-6-methoxyindazol-1-yl)propan-2-amine Chemical compound COC1=CC=C2C(Cl)=NN(CC(C)N)C2=C1 PNHDUSKIMUKQDR-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- 238000010411 cooking Methods 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 41
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
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| US19038000P | 2000-03-17 | 2000-03-17 |
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| TWI221839B true TWI221839B (en) | 2004-10-11 |
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| TW089125127A TWI221839B (en) | 2000-03-17 | 2000-11-27 | 6-hydroxy-indazole derivatives for treating glaucoma |
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| JP (1) | JP2003528085A (https=) |
| KR (1) | KR20030065304A (https=) |
| CN (1) | CN1450994A (https=) |
| AR (1) | AR032138A1 (https=) |
| AU (1) | AU2001216072A1 (https=) |
| BR (1) | BR0017157A (https=) |
| CA (1) | CA2402403A1 (https=) |
| GC (1) | GC0000155A (https=) |
| MX (1) | MXPA02008547A (https=) |
| PL (1) | PL358481A1 (https=) |
| TW (1) | TWI221839B (https=) |
| WO (1) | WO2001070702A1 (https=) |
| ZA (1) | ZA200206851B (https=) |
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|---|---|---|---|---|
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| TW593302B (en) | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| AU2002360819A1 (en) * | 2001-12-28 | 2003-07-24 | Bayer Corporation | Cyclohexano- and cycloheptapyrazole derivative compounds, for use in diseases associated with the 5-ht2c receptor |
| AU2003287481B2 (en) | 2002-11-08 | 2009-04-23 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| US7196082B2 (en) | 2002-11-08 | 2007-03-27 | Merck & Co. Inc. | Ophthalmic compositions for treating ocular hypertension |
| CN100384827C (zh) * | 2002-11-08 | 2008-04-30 | 默克公司 | 用于治疗高眼压症的眼用组合物 |
| US7053085B2 (en) | 2003-03-26 | 2006-05-30 | Merck & Co. Inc. | EP4 receptor agonist, compositions and methods thereof |
| BR0316775A (pt) | 2002-12-13 | 2005-11-01 | Alcon Inc | Novos análogos de benzopirano e seu uso para o tratamento de glaucoma |
| JP2004262812A (ja) * | 2003-02-28 | 2004-09-24 | Rohto Pharmaceut Co Ltd | 眼圧低下剤 |
| AU2004268012B2 (en) | 2003-09-02 | 2008-11-20 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| DE602004020079D1 (de) | 2003-09-04 | 2009-04-30 | Merck & Co Inc | Ophthalmische zusammensetzungen zur behandlung der okularen hypertonie |
| AU2004271978B2 (en) | 2003-09-04 | 2009-02-05 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| TW200520760A (en) | 2003-12-15 | 2005-07-01 | Alcon Inc | Substituted [1,4] oxazino [2,3-g] indazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| US7129257B1 (en) | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| CN1988903A (zh) | 2004-07-20 | 2007-06-27 | 默克公司 | 用于治疗高眼压症的眼用组合物 |
| ATE460415T1 (de) | 2004-11-29 | 2010-03-15 | Warner Lambert Co | Therapeutische pyrazoloä3,4-büpyridine und - indazole |
| US7425572B2 (en) | 2004-12-08 | 2008-09-16 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| CN101704785B (zh) * | 2009-11-16 | 2012-02-29 | 东南大学 | 有机二羧酸和其盐及其制备方法 |
| CN105884687B (zh) * | 2016-04-14 | 2018-06-22 | 梯尔希（南京）药物研发有限公司 | 一种5-苄基苄达明的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1301161A (zh) * | 1998-05-19 | 2001-06-27 | 艾尔科实验室公司 | 用于治疗眼睛和中枢神经系统障碍的血清素激活的5ht7受体化合物 |
| ATE247963T1 (de) * | 1998-05-26 | 2003-09-15 | Pfizer Prod Inc | Medikament zur behandlung von glaukoma und ischämischer retinopathie |
| GB9819032D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds IV |
| CN1269484C (zh) * | 1998-09-18 | 2006-08-16 | 艾尔科实验室公司 | 用于治疗青光眼的5－羟色胺激活性激动剂 |
| GB9820767D0 (en) * | 1998-09-23 | 1998-11-18 | Cerebrus Ltd | Chemical compounds VIII |
-
2000
- 2000-11-14 BR BR0017157-3A patent/BR0017157A/pt not_active IP Right Cessation
- 2000-11-14 WO PCT/US2000/031247 patent/WO2001070702A1/en not_active Ceased
- 2000-11-14 KR KR1020027011867A patent/KR20030065304A/ko not_active Ceased
- 2000-11-14 PL PL00358481A patent/PL358481A1/xx not_active Application Discontinuation
- 2000-11-14 MX MXPA02008547A patent/MXPA02008547A/es unknown
- 2000-11-14 AU AU2001216072A patent/AU2001216072A1/en not_active Abandoned
- 2000-11-14 EP EP00978628A patent/EP1268438A1/en not_active Withdrawn
- 2000-11-14 JP JP2001568912A patent/JP2003528085A/ja not_active Withdrawn
- 2000-11-14 CA CA002402403A patent/CA2402403A1/en not_active Abandoned
- 2000-11-14 CN CN00819346A patent/CN1450994A/zh active Pending
- 2000-11-27 TW TW089125127A patent/TWI221839B/zh not_active IP Right Cessation
- 2000-12-01 AR ARP000106394A patent/AR032138A1/es not_active Application Discontinuation
- 2000-12-03 GC GCP20001082 patent/GC0000155A/xx active
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2002
- 2002-08-27 ZA ZA200206851A patent/ZA200206851B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2402403A1 (en) | 2001-09-27 |
| AR032138A1 (es) | 2003-10-29 |
| JP2003528085A (ja) | 2003-09-24 |
| PL358481A1 (en) | 2004-08-09 |
| ZA200206851B (en) | 2003-10-21 |
| WO2001070702A1 (en) | 2001-09-27 |
| CN1450994A (zh) | 2003-10-22 |
| MXPA02008547A (es) | 2003-03-12 |
| AU2001216072A1 (en) | 2001-10-03 |
| BR0017157A (pt) | 2002-11-26 |
| EP1268438A1 (en) | 2003-01-02 |
| KR20030065304A (ko) | 2003-08-06 |
| GC0000155A (en) | 2005-06-29 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |