SK399A3 - Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use - Google Patents

Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use Download PDF

Info

Publication number: SK399A3
Authority: SK; Slovakia
Prior art keywords: free base; compound; formula; methyl; acid salt
Prior art date: 1996-07-08

Application number

SK3-99A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Gull

Rudolf Markstein

Max P Seiler

Original Assignee

Novartis Ag

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.)

1996-07-08

Filing date

1997-07-07

Publication date

1999-06-11

1996-07-08 Priority claimed from GBGB9614282.3A external-priority patent/GB9614282D0/en

1996-12-16 Priority claimed from GBGB9626093.0A external-priority patent/GB9626093D0/en

1997-07-07 Application filed by Novartis Ag filed Critical Novartis Ag

1999-06-11 Publication of SK399A3 publication Critical patent/SK399A3/sk

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
RFQDDXWZZVRLKO-UHFFFAOYSA-N benzo[g]quinoline Chemical class N1=CC=CC2=CC3=CC=CC=C3C=C21 RFQDDXWZZVRLKO-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 51
208000010412 Glaucoma Diseases 0.000 claims abstract description 13
230000004379 myopia Effects 0.000 claims abstract description 12
208000001491 myopia Diseases 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 9
150000003839 salts Chemical group 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 15
239000012458 free base Substances 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
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 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000017531 blood circulation Effects 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
230000004410 intraocular pressure Effects 0.000 description 5
210000001328 optic nerve Anatomy 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
-1 atom hydrogen Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
239000002876 beta blocker Substances 0.000 description 2
229940097320 beta blocking agent Drugs 0.000 description 2
230000003291 dopaminomimetic effect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
230000004438 eyesight Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000003128 head Anatomy 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002997 ophthalmic solution Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229960004605 timolol Drugs 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
AGWWTUWTOBEQFE-UHFFFAOYSA-N 4-methyl-1h-1,2,4-triazole-5-thione Chemical compound CN1C=NN=C1S AGWWTUWTOBEQFE-UHFFFAOYSA-N 0.000 description 1
238000010953 Ames test Methods 0.000 description 1
231100000039 Ames test Toxicity 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000008081 blood perfusion Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003727 cerebral blood flow Effects 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000002872 contrast media Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229960002725 isoflurane Drugs 0.000 description 1
230000005291 magnetic effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
230000007886 mutagenicity Effects 0.000 description 1
231100000299 mutagenicity Toxicity 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940054534 ophthalmic solution Drugs 0.000 description 1
208000001749 optic atrophy Diseases 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
PRGUDWLMFLCODA-UHFFFAOYSA-N oxybuprocaine hydrochloride Chemical compound [Cl-].CCCCOC1=CC(C(=O)OCC[NH+](CC)CC)=CC=C1N PRGUDWLMFLCODA-UHFFFAOYSA-N 0.000 description 1
230000005298 paramagnetic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000902 placebo Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- 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
- A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Ophthalmology & Optometry (AREA)
Bioinformatics & Cheminformatics (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)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK3-99A 1996-07-08 1997-07-07 Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use SK399A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9614282.3A GB9614282D0 (en)	1996-07-08	1996-07-08	Organic compounds
GBGB9626093.0A GB9626093D0 (en)	1996-12-16	1996-12-16	Organic compounds
PCT/EP1997/003582 WO1998001444A1 (en)	1996-07-08	1997-07-07	BENZO[g]QUINOLINE DERIVATIVES

Publications (1)

Publication Number	Publication Date
SK399A3 true SK399A3 (en)	1999-06-11

Family

ID=26309658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK3-99A SK399A3 (en)	1996-07-08	1997-07-07	Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use

Country Status (27)

Country	Link
US (1)	US6057334A (de)
EP (1)	EP0912553B1 (de)
JP (1)	JP4216337B2 (de)
KR (1)	KR100491478B1 (de)
CN (1)	CN1125065C (de)
AR (1)	AR007814A1 (de)
AT (1)	ATE211470T1 (de)
AU (1)	AU719119B2 (de)
BR (1)	BR9710218A (de)
CA (1)	CA2257646C (de)
CO (1)	CO4870760A1 (de)
CY (1)	CY2322B1 (de)
CZ (1)	CZ2799A3 (de)
DE (1)	DE69709869T2 (de)
DK (1)	DK0912553T3 (de)
ES (1)	ES2170402T3 (de)
ID (1)	ID18896A (de)
IL (1)	IL127376A (de)
NO (1)	NO319401B1 (de)
NZ (1)	NZ333311A (de)
PE (1)	PE87998A1 (de)
PL (1)	PL330723A1 (de)
PT (1)	PT912553E (de)
SK (1)	SK399A3 (de)
TR (1)	TR199900016T2 (de)
TW (1)	TW378209B (de)
WO (1)	WO1998001444A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PE20030240A1 (es) *	2001-07-09	2003-04-16	Novartis Ag	DERIVADOS DE BENZO [g] QUINOLINA
EG24415A (en) *	2002-03-07	2009-05-25	Novartis Ag	Quinoline derivatives
ATE438640T1 (de) *	2002-03-07	2009-08-15	Novartis Pharma Gmbh	Chinolinderivate und ihre anwendung bei glaukom und kurzsichtigkeit
MXPA06002484A (es) *	2003-09-05	2006-06-20	Novartis Ag	Composiciones que comprenden derivados de benzo[g]quinolina y derivados de prostaglandina.
CN105434439B (zh) *	2015-11-11	2018-07-24	温州医科大学	一种多巴胺d2受体的部分激动剂在制备抑制近视药物上的应用及其使用方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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LU88619I2 (fr) *	1981-10-16	1995-07-10	Sandoz Ag	QUINAGOLIDE, éventuellement sous forme de sel, par exemple du chlorhydrate
AU3879789A (en) *	1988-07-22	1990-02-19	Sandoz Ag	Use of benzo(g)quinolines in treatment of nicotine addiction
GB8829330D0 (en) *	1988-12-16	1989-02-01	Sandoz Ltd	Improvements in or relating to organic compounds
US5262422A (en) *	1991-05-02	1993-11-16	Sandoz Ltd.	Octahydrobenzo[g]quinoline
DE4114325A1 (de) *	1991-05-02	1992-11-05	Sandoz Ag	Octahydrobenzo(g)chinolin, seine herstellung und verwendung
GB9326010D0 (en) *	1993-12-21	1994-02-23	Sandoz Ltd	Improvements in or relating to organic compounds
FR2729145A1 (fr) *	1995-01-06	1996-07-12	Smithkline Beecham Lab	Nouveaux derives d'amine, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu'agents anti-arythmiques

1997
- 1997-06-16 TW TW086108396A patent/TW378209B/zh not_active IP Right Cessation
- 1997-07-07 TR TR1999/00016T patent/TR199900016T2/xx unknown
- 1997-07-07 PE PE1997000585A patent/PE87998A1/es not_active Application Discontinuation
- 1997-07-07 DK DK97931793T patent/DK0912553T3/da active
- 1997-07-07 CN CN97196208A patent/CN1125065C/zh not_active Expired - Fee Related
- 1997-07-07 NZ NZ333311A patent/NZ333311A/en not_active IP Right Cessation
- 1997-07-07 CZ CZ9927A patent/CZ2799A3/cs unknown
- 1997-07-07 DE DE69709869T patent/DE69709869T2/de not_active Expired - Lifetime
- 1997-07-07 CO CO97037766A patent/CO4870760A1/es unknown
- 1997-07-07 AU AU35422/97A patent/AU719119B2/en not_active Ceased
- 1997-07-07 SK SK3-99A patent/SK399A3/sk unknown
- 1997-07-07 JP JP50478898A patent/JP4216337B2/ja not_active Expired - Fee Related
- 1997-07-07 AR ARP970103017A patent/AR007814A1/es active IP Right Grant
- 1997-07-07 IL IL12737697A patent/IL127376A/xx not_active IP Right Cessation
- 1997-07-07 BR BR9710218A patent/BR9710218A/pt not_active IP Right Cessation
- 1997-07-07 US US09/214,537 patent/US6057334A/en not_active Expired - Lifetime
- 1997-07-07 ID IDP972340A patent/ID18896A/id unknown
- 1997-07-07 KR KR10-1999-7000016A patent/KR100491478B1/ko not_active Expired - Fee Related
- 1997-07-07 EP EP97931793A patent/EP0912553B1/de not_active Expired - Lifetime
- 1997-07-07 PL PL97330723A patent/PL330723A1/xx unknown
- 1997-07-07 ES ES97931793T patent/ES2170402T3/es not_active Expired - Lifetime
- 1997-07-07 PT PT97931793T patent/PT912553E/pt unknown
- 1997-07-07 WO PCT/EP1997/003582 patent/WO1998001444A1/en not_active Ceased
- 1997-07-07 CA CA002257646A patent/CA2257646C/en not_active Expired - Fee Related
- 1997-07-07 AT AT97931793T patent/ATE211470T1/de active
1999
- 1999-01-05 NO NO19990035A patent/NO319401B1/no not_active IP Right Cessation
2003
- 2003-04-30 CY CY0300034A patent/CY2322B1/xx unknown

Also Published As

Publication number	Publication date
ID18896A (id)	1998-05-20
PL330723A1 (en)	1999-05-24
TR199900016T2 (xx)	1999-04-21
EP0912553A1 (de)	1999-05-06
AR007814A1 (es)	1999-11-24
NZ333311A (en)	2000-06-23
CN1125065C (zh)	2003-10-22
JP2000514075A (ja)	2000-10-24
PT912553E (pt)	2002-06-28
AU3542297A (en)	1998-02-02
CN1225093A (zh)	1999-08-04
PE87998A1 (es)	1998-12-30
KR20000023572A (ko)	2000-04-25
IL127376A (en)	2003-12-10
EP0912553B1 (de)	2002-01-02
CA2257646A1 (en)	1998-01-15
IL127376A0 (en)	1999-10-28
CA2257646C (en)	2006-05-09
HK1020569A1 (en)	2000-05-12
NO990035D0 (no)	1999-01-05
TW378209B (en)	2000-01-01
DE69709869D1 (de)	2002-02-28
JP4216337B2 (ja)	2009-01-28
ATE211470T1 (de)	2002-01-15
CZ2799A3 (cs)	1999-03-17
DK0912553T3 (da)	2002-04-22
AU719119B2 (en)	2000-05-04
NO319401B1 (no)	2005-08-08
DE69709869T2 (de)	2002-08-14
ES2170402T3 (es)	2002-08-01
CY2322B1 (en)	2003-11-14
BR9710218A (pt)	1999-08-10
NO990035L (no)	1999-01-05
WO1998001444A1 (en)	1998-01-15
US6057334A (en)	2000-05-02
KR100491478B1 (ko)	2005-05-27
CO4870760A1 (es)	1999-12-27

Publication	Publication Date	Title
IE913202A1 (en)	1992-02-25	6- or 7- (2-imino-2-imidazolidine)-1,4-benzoxazines as alpha¹adrenergic agents
JPH0717633B2 (ja)	1995-03-01	ヘテロアリールピペラジン抗精神病薬
JP2010024243A (ja)	2010-02-04	緑内障および近視を処置するためのベンゾ［ｇ］キノリン誘導体
JP2010095550A (ja)	2010-04-30	キノリン誘導体
JP2002053566A (ja)	2002-02-19	チアゾール化合物及びその医薬用途
US5066664A (en)	1991-11-19	2-(hydroxy-2-alkylphenylamino)-oxazolines and thiazolines as anti-glaucoma and vasoconstrictive agents
SK399A3 (en)	1999-06-11	Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use
US6602865B1 (en)	2003-08-05	Pyridazino(4,5-b)(1,5)oxazepinone, -thiazepinone and -diazepinone compounds
KR100636515B1 (ko)	2006-10-18	신규 형태의 축합 피리다지논 화합물
HK1020569B (en)	2002-08-30	Benzo[g]quinoline derivatives
WO2026019295A1 (ko)	2026-01-22	3-피리딜이속사졸 유도체 및 이를 유효성분으로 함유하는 안질환 예방 또는 치료용 약학 조성물
GB2270313A (en)	1994-03-09	1,3,4-Benzotriazepin-5(4H) - one derivatives
HK1066211B (en)	2010-04-16	Benzo [g] quinoline derivatives for treating glaucoma and myopia
SE180546C1 (de)	1962-01-01