DE60311233T2 - Chinolinderivate - Google Patents
Chinolinderivate Download PDFInfo
- Publication number
- DE60311233T2 DE60311233T2 DE60311233T DE60311233T DE60311233T2 DE 60311233 T2 DE60311233 T2 DE 60311233T2 DE 60311233 T DE60311233 T DE 60311233T DE 60311233 T DE60311233 T DE 60311233T DE 60311233 T2 DE60311233 T2 DE 60311233T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- acid addition
- glaucoma
- free base
- formula
- Prior art date
- 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.)
- Expired - Lifetime
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 208000001491 myopia Diseases 0.000 claims description 7
- 230000004379 myopia Effects 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 11
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000004410 intraocular pressure Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 2-methoxyethoxy Chemical group 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GRPDTQVFLZSLBL-FRFSOERESA-N C[n]1c(SC[C@H](C2)CN(C)[C@H](C3)[C@H]2Cc2c3cccc2O)ncc1 Chemical compound C[n]1c(SC[C@H](C2)CN(C)[C@H](C3)[C@H]2Cc2c3cccc2O)ncc1 GRPDTQVFLZSLBL-FRFSOERESA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- RFQDDXWZZVRLKO-UHFFFAOYSA-N benzo[g]quinoline Chemical class N1=CC=CC2=CC3=CC=CC=C3C=C21 RFQDDXWZZVRLKO-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002997 ophthalmic solution 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
- 230000035515 penetration Effects 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012730 sustained-release form Substances 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02005115 | 2002-03-07 | ||
| EP02005117 | 2002-03-07 | ||
| EP02005117 | 2002-03-07 | ||
| EP02005115 | 2002-03-07 | ||
| PCT/EP2003/002321 WO2003074511A1 (en) | 2002-03-07 | 2003-03-06 | Quinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60311233D1 DE60311233D1 (de) | 2007-03-08 |
| DE60311233T2 true DE60311233T2 (de) | 2007-11-15 |
Family
ID=27790094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60311233T Expired - Lifetime DE60311233T2 (de) | 2002-03-07 | 2003-03-06 | Chinolinderivate |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US7399768B2 (https=) |
| EP (1) | EP1480970B1 (https=) |
| JP (2) | JP2005519117A (https=) |
| KR (1) | KR101027977B1 (https=) |
| CN (2) | CN1939915A (https=) |
| AR (1) | AR038730A1 (https=) |
| AU (1) | AU2003219023B2 (https=) |
| BR (1) | BR0308201A (https=) |
| CA (2) | CA2477720C (https=) |
| CO (1) | CO5611196A2 (https=) |
| CY (1) | CY1106409T1 (https=) |
| DE (1) | DE60311233T2 (https=) |
| DK (1) | DK1480970T3 (https=) |
| EC (1) | ECSP045271A (https=) |
| EG (1) | EG24415A (https=) |
| ES (1) | ES2279100T3 (https=) |
| IL (1) | IL163769A0 (https=) |
| MX (1) | MXPA04008666A (https=) |
| MY (1) | MY134325A (https=) |
| NO (1) | NO20044117L (https=) |
| NZ (1) | NZ534732A (https=) |
| PE (1) | PE20030927A1 (https=) |
| PL (2) | PL210336B1 (https=) |
| PT (1) | PT1480970E (https=) |
| RU (1) | RU2345991C2 (https=) |
| SI (1) | SI1480970T1 (https=) |
| TW (1) | TW200406401A (https=) |
| WO (1) | WO2003074511A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60328732D1 (de) * | 2002-03-07 | 2009-09-17 | Novartis Ag | Chinolinderivate und ihre Anwendung bei Glaukom und Kurzsichtigkeit |
| JP7320507B2 (ja) | 2017-11-24 | 2023-08-03 | ハー・ルンドベック・アクチエゼルスカベット | パーキンソン病の治療に使用するための新規なカテコールアミンプロドラッグ |
| US11130775B2 (en) | 2019-05-20 | 2021-09-28 | H. Lundbeck A/S | Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11104697B2 (en) | 2019-05-20 | 2021-08-31 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4AR,10AR)-7-hydroxy-1- propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11168056B2 (en) | 2019-05-20 | 2021-11-09 | H. Lundbeck A/S | Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol |
| US11111263B2 (en) | 2019-05-20 | 2021-09-07 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| CN113727712B (zh) | 2019-05-21 | 2024-11-15 | H.隆德贝克有限公司 | 用于治疗帕金森病的儿茶酚胺氨基甲酸酯前药 |
| EP3972971A1 (en) | 2019-05-21 | 2022-03-30 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's diseases |
| WO2020234274A1 (en) | 2019-05-21 | 2020-11-26 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's disease |
| JP7562562B2 (ja) | 2019-05-21 | 2024-10-07 | ハー・ルンドベック・アクチエゼルスカベット | パーキンソン病の治療に使用するための新規なカテコールアミンプロドラッグ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL100555A (en) * | 1991-02-07 | 2000-08-31 | Hoechst Marion Roussel Inc | N-substituted quinoline derivatives their preparation their use for the preparation of medicaments and the pharmaceutical compositions containing them |
| GB9326010D0 (en) * | 1993-12-21 | 1994-02-23 | Sandoz Ltd | Improvements in or relating to organic compounds |
| TW378209B (en) * | 1996-07-08 | 2000-01-01 | Novartis Ag | Benzo[g]quinoline derivatives, their preparation and the pharmaceutical composition containing them |
| PE20030240A1 (es) * | 2001-07-09 | 2003-04-16 | Novartis Ag | DERIVADOS DE BENZO [g] QUINOLINA |
-
2003
- 2003-03-03 EG EG2003030215A patent/EG24415A/xx active
- 2003-03-05 PE PE2003000212A patent/PE20030927A1/es not_active Application Discontinuation
- 2003-03-05 TW TW092104671A patent/TW200406401A/zh unknown
- 2003-03-05 AR ARP030100740A patent/AR038730A1/es unknown
- 2003-03-06 MX MXPA04008666A patent/MXPA04008666A/es active IP Right Grant
- 2003-03-06 BR BR0308201-6A patent/BR0308201A/pt not_active Application Discontinuation
- 2003-03-06 CN CNA2006101357990A patent/CN1939915A/zh active Pending
- 2003-03-06 SI SI200330755T patent/SI1480970T1/sl unknown
- 2003-03-06 RU RU2004129767/04A patent/RU2345991C2/ru not_active IP Right Cessation
- 2003-03-06 JP JP2003572979A patent/JP2005519117A/ja active Pending
- 2003-03-06 PL PL370915A patent/PL210336B1/pl unknown
- 2003-03-06 PL PL394208A patent/PL215012B1/pl unknown
- 2003-03-06 AU AU2003219023A patent/AU2003219023B2/en not_active Ceased
- 2003-03-06 KR KR1020047012409A patent/KR101027977B1/ko not_active Expired - Fee Related
- 2003-03-06 IL IL16376903A patent/IL163769A0/xx unknown
- 2003-03-06 PT PT03714784T patent/PT1480970E/pt unknown
- 2003-03-06 DE DE60311233T patent/DE60311233T2/de not_active Expired - Lifetime
- 2003-03-06 EP EP03714784A patent/EP1480970B1/en not_active Expired - Lifetime
- 2003-03-06 CA CA2477720A patent/CA2477720C/en not_active Expired - Fee Related
- 2003-03-06 US US10/506,232 patent/US7399768B2/en not_active Expired - Fee Related
- 2003-03-06 CN CNB038053608A patent/CN1293070C/zh not_active Expired - Fee Related
- 2003-03-06 NZ NZ534732A patent/NZ534732A/en unknown
- 2003-03-06 ES ES03714784T patent/ES2279100T3/es not_active Expired - Lifetime
- 2003-03-06 WO PCT/EP2003/002321 patent/WO2003074511A1/en not_active Ceased
- 2003-03-06 DK DK03714784T patent/DK1480970T3/da active
- 2003-03-06 CA CA2706618A patent/CA2706618A1/en not_active Abandoned
- 2003-03-07 MY MYPI20030808A patent/MY134325A/en unknown
-
2004
- 2004-09-02 EC EC2004005271A patent/ECSP045271A/es unknown
- 2004-09-15 CO CO04091781A patent/CO5611196A2/es not_active Application Discontinuation
- 2004-09-28 NO NO20044117A patent/NO20044117L/no not_active Application Discontinuation
-
2007
- 2007-03-22 CY CY20071100405T patent/CY1106409T1/el unknown
-
2008
- 2008-06-12 US US12/137,819 patent/US20080255176A1/en not_active Abandoned
-
2010
- 2010-02-04 JP JP2010022863A patent/JP2010095550A/ja active Pending
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