AU2001216072A1 - 6-hydroxy-indazole derivatives for treating glaucoma - Google Patents

6-hydroxy-indazole derivatives for treating glaucoma

Info

Publication number: AU2001216072A1
Authority: AU; Australia
Prior art keywords: alkyl; hydrogen; independently chosen; halogen; substituted
Prior art date: 2000-03-17
Legal status (The legal status 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 status listed.): Abandoned

Application number

AU2001216072A

Other languages

English (en)

Inventor

Anura P. Dantanarayana

Zixia Feng

Jesse A. May

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Alcon Inc

Original Assignee

Alcon Universal Ltd

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.)

2000-03-17

Filing date

2000-11-14

Publication date

2001-10-03

2000-11-14 Application filed by Alcon Universal Ltd filed Critical Alcon Universal Ltd

2001-10-03 Publication of AU2001216072A1 publication Critical patent/AU2001216072A1/en

Status Abandoned legal-status Critical Current

Links

208000010412 Glaucoma Diseases 0.000 title claims description 16
NUYZVDBIVNOTSC-UHFFFAOYSA-N 1H-indazol-6-ol Chemical class OC1=CC=C2C=NNC2=C1 NUYZVDBIVNOTSC-UHFFFAOYSA-N 0.000 title description 3
239000001257 hydrogen Substances 0.000 claims description 73
229910052739 hydrogen Inorganic materials 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 59
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
230000000699 topical effect Effects 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims 3
FFYVXJGEDQXQBK-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.NC(CN1N=C(C2=CC=C(C=C12)O)C)C.ClC1=NN(C2=CC(=CC=C12)OC)CC(C)N.C(C=CC(=O)O)(=O)O.NC(CN1N=C(C2=CC=C(C=C12)O)C)C Chemical compound C(C=CC(=O)O)(=O)O.NC(CN1N=C(C2=CC=C(C=C12)O)C)C.ClC1=NN(C2=CC(=CC=C12)OC)CC(C)N.C(C=CC(=O)O)(=O)O.NC(CN1N=C(C2=CC=C(C=C12)O)C)C FFYVXJGEDQXQBK-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000000556 agonist Substances 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
230000004410 intraocular pressure Effects 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
239000007787 solid Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
-1 d-6alkyl Chemical class 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
210000003169 central nervous system Anatomy 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002473 indoazoles Chemical class 0.000 description 5
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
238000004458 analytical method Methods 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229960000367 inositol Drugs 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229940054534 ophthalmic solution Drugs 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
150000003906 phosphoinositides Chemical class 0.000 description 4
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
230000000862 serotonergic effect Effects 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
BGMZUEKZENQUJY-UHFFFAOYSA-N 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1I BGMZUEKZENQUJY-UHFFFAOYSA-N 0.000 description 3
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
206010030043 Ocular hypertension Diseases 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000000872 buffer Substances 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
230000004406 elevated intraocular pressure Effects 0.000 description 3
LIHGLLXHHBMMCF-UHFFFAOYSA-N n-ethylindazol-1-amine Chemical group C1=CC=C2N(NCC)N=CC2=C1 LIHGLLXHHBMMCF-UHFFFAOYSA-N 0.000 description 3
239000002997 ophthalmic solution Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000012360 testing method Methods 0.000 description 3
230000004382 visual function Effects 0.000 description 3
WSEWULCWBQDNEH-UHFFFAOYSA-N 1-(6-methoxyindazol-1-yl)propan-2-amine Chemical compound COC1=CC=C2C=NN(CC(C)N)C2=C1 WSEWULCWBQDNEH-UHFFFAOYSA-N 0.000 description 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 2
RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
206010067013 Normal tension glaucoma Diseases 0.000 description 2
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
108091006463 SLC25A24 Proteins 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000027455 binding Effects 0.000 description 2
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
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KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
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238000004519 manufacturing process Methods 0.000 description 2
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AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
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TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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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
- 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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)

AU2001216072A 2000-03-17 2000-11-14 6-hydroxy-indazole derivatives for treating glaucoma Abandoned AU2001216072A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US19038000P	2000-03-17	2000-03-17
US60/190,380		2000-03-17
PCT/US2000/031247 WO2001070702A1 (en)	2000-03-17	2000-11-14	6-hydroxy-indazole derivatives for treating glaucoma

Publications (1)

Publication Number	Publication Date
AU2001216072A1 true AU2001216072A1 (en)	2001-10-03

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ID=22701093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001216072A Abandoned AU2001216072A1 (en)	2000-03-17	2000-11-14	6-hydroxy-indazole derivatives for treating glaucoma

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Country	Link
EP (1)	EP1268438A1 (es)
JP (1)	JP2003528085A (es)
KR (1)	KR20030065304A (es)
CN (1)	CN1450994A (es)
AR (1)	AR032138A1 (es)
AU (1)	AU2001216072A1 (es)
BR (1)	BR0017157A (es)
CA (1)	CA2402403A1 (es)
GC (1)	GC0000155A (es)
MX (1)	MXPA02008547A (es)
PL (1)	PL358481A1 (es)
TW (1)	TWI221839B (es)
WO (1)	WO2001070702A1 (es)
ZA (1)	ZA200206851B (es)

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* Cited by examiner, † Cited by third party
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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
WO2003057213A2 (en) *	2001-12-28	2003-07-17	Bayer Pharmaceuticals Corporation	Cyclohexano- and cycloheptapyrazole derivative compounds, for use in diseases associated with the 5-ht2c receptor
CA2505127A1 (en)	2002-11-08	2004-05-27	James B. Doherty	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
US7196082B2 (en)	2002-11-08	2007-03-27	Merck & Co. Inc.	Ophthalmic compositions for treating ocular hypertension
US7053085B2 (en)	2003-03-26	2006-05-30	Merck & Co. Inc.	EP4 receptor agonist, compositions and methods thereof
WO2004054572A2 (en)	2002-12-13	2004-07-01	Alcon, Inc.	Novel benzopyran analogs and their use for the treatment of glaucoma
JP2004262812A (ja) *	2003-02-28	2004-09-24	Rohto Pharmaceut Co Ltd	眼圧低下剤
CA2537119A1 (en)	2003-09-02	2005-03-10	Merck & Co., Inc.	Ophthalmic compositions for treating ocular hypertension
AU2004271978B2 (en)	2003-09-04	2009-02-05	Merck & Co., Inc.	Ophthalmic compositions for treating ocular hypertension
WO2005026128A1 (en)	2003-09-04	2005-03-24	Merck & Co., Inc.	Ophthalmic compositions for treating ocular hypertension
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
US6989445B2 (en)	2003-12-15	2006-01-24	Alcon, Inc.	Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma
US7563816B2 (en)	2004-07-20	2009-07-21	Merck & Co. Inc.	Ophthalmic compositions for treating ocular hypertension
MX2007006408A (es)	2004-11-29	2007-06-22	Warner Lambert Co	Pirazolo[3,4-b]piridinas e indazoles terapeuticos.
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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3978899A (en) *	1998-05-19	1999-12-06	Alcon Laboratories, Inc.	Serotonergic 5HT, receptor compounds for treating ocular and CNS disorders
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
TR200100754T2 (tr) *	1998-09-18	2001-10-22	Alcon Laboratories, Inc.	Glausomanın tedavi edilmesi için serotonerjik 5HT2.
GB9820767D0 (en) *	1998-09-23	1998-11-18	Cerebrus Ltd	Chemical compounds VIII

2000
- 2000-11-14 WO PCT/US2000/031247 patent/WO2001070702A1/en not_active Ceased
- 2000-11-14 CA CA002402403A patent/CA2402403A1/en not_active Abandoned
- 2000-11-14 BR BR0017157-3A patent/BR0017157A/pt not_active IP Right Cessation
- 2000-11-14 MX MXPA02008547A patent/MXPA02008547A/es unknown
- 2000-11-14 CN CN00819346A patent/CN1450994A/zh active Pending
- 2000-11-14 EP EP00978628A patent/EP1268438A1/en not_active Withdrawn
- 2000-11-14 PL PL00358481A patent/PL358481A1/xx not_active Application Discontinuation
- 2000-11-14 JP JP2001568912A patent/JP2003528085A/ja not_active Withdrawn
- 2000-11-14 AU AU2001216072A patent/AU2001216072A1/en not_active Abandoned
- 2000-11-14 KR KR1020027011867A patent/KR20030065304A/ko not_active Ceased
- 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
2002
- 2002-08-27 ZA ZA200206851A patent/ZA200206851B/en unknown

Also Published As

Publication number	Publication date
CA2402403A1 (en)	2001-09-27
CN1450994A (zh)	2003-10-22
MXPA02008547A (es)	2003-03-12
AR032138A1 (es)	2003-10-29
BR0017157A (pt)	2002-11-26
WO2001070702A1 (en)	2001-09-27
EP1268438A1 (en)	2003-01-02
JP2003528085A (ja)	2003-09-24
GC0000155A (en)	2005-06-29
KR20030065304A (ko)	2003-08-06
ZA200206851B (en)	2003-10-21
PL358481A1 (en)	2004-08-09
TWI221839B (en)	2004-10-11

Publication	Publication Date	Title
US6956036B1 (en)	2005-10-18	6-hydroxy-indazole derivatives for treating glaucoma
AU2001216072A1 (en)	2001-10-03	6-hydroxy-indazole derivatives for treating glaucoma
US6660870B1 (en)	2003-12-09	2-acylaminobenzimidazole derivatives for treating glaucoma
US6960608B2 (en)	2005-11-01	Fused indazoles and indoles and their use for the treatment of glaucoma
AU2001219180B2 (en)	2005-04-07	5-hydroxy indazole derivatives for treating glaucoma
WO2001040183A1 (en)	2001-06-07	1-aminoalkyl-1h-indoles for treating glaucoma
AU2001219180A1 (en)	2001-12-13	5-hydroxy indazole derivatives for treating glaucoma
AU2002259312A1 (en)	2003-05-08	Novel arylaminopropane analogues and their use for the treatment of glaucoma
WO2002098400A1 (en)	2002-12-12	Novel arylaminopropane analogues and their use for the treatment of glaucoma
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