CA2087510A1 - Method of using m1-selective antimuscarinic pyridobenzodiazepiones in axial myopia therapy - Google Patents
Method of using m1-selective antimuscarinic pyridobenzodiazepiones in axial myopia therapyInfo
- Publication number
- CA2087510A1 CA2087510A1 CA002087510A CA2087510A CA2087510A1 CA 2087510 A1 CA2087510 A1 CA 2087510A1 CA 002087510 A CA002087510 A CA 002087510A CA 2087510 A CA2087510 A CA 2087510A CA 2087510 A1 CA2087510 A1 CA 2087510A1
- Authority
- CA
- Canada
- Prior art keywords
- animal
- myopia
- eye
- compound
- 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.)
- Abandoned
Links
- 230000004329 axial myopia Effects 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 17
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 16
- 230000001022 anti-muscarinic effect Effects 0.000 title description 3
- 241001465754 Metazoa Species 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 230000002159 abnormal effect Effects 0.000 claims abstract description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 210000001110 axial length eye Anatomy 0.000 claims abstract 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000027455 binding Effects 0.000 abstract description 6
- 238000009739 binding Methods 0.000 abstract description 6
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 abstract description 4
- 229960004373 acetylcholine Drugs 0.000 abstract description 4
- MGDDXKBVXQCWER-UHFFFAOYSA-N pyrido[2,3-i][1,2]benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=C(N=CC=C3)C3=C21 MGDDXKBVXQCWER-UHFFFAOYSA-N 0.000 abstract description 2
- 210000001508 eye Anatomy 0.000 description 35
- 230000004379 myopia Effects 0.000 description 32
- 208000001491 myopia Diseases 0.000 description 32
- 229960004633 pirenzepine Drugs 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- HPKYRXAEGNUARA-UHFFFAOYSA-N 11-(1-methylpiperidine-4-carbonyl)-6h-pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C1CN(C)CCC1C(=O)N1C2=NC=CC=C2C(=O)NC2=CC=CC=C21 HPKYRXAEGNUARA-UHFFFAOYSA-N 0.000 description 14
- 229930003347 Atropine Natural products 0.000 description 14
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 14
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 14
- 229960000396 atropine Drugs 0.000 description 14
- 229950007677 nuvenzepine Drugs 0.000 description 14
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 14
- 238000011161 development Methods 0.000 description 10
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- 229940079593 drug Drugs 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 210000001525 retina Anatomy 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LPLNSPKKMWHFAU-UHFFFAOYSA-N 11-(1-methylpiperidine-3-carbonyl)-6h-pyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound C1N(C)CCCC1C(=O)N1C2=NC=CC=C2C(=O)NC2=CC=CC=C21 LPLNSPKKMWHFAU-UHFFFAOYSA-N 0.000 description 5
- 201000009487 Amblyopia Diseases 0.000 description 5
- 229950005803 rispenzepine Drugs 0.000 description 5
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- 235000019271 petrolatum Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 241000288906 Primates Species 0.000 description 3
- 102000034337 acetylcholine receptors Human genes 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- 102000017926 CHRM2 Human genes 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 101150012960 Chrm2 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020675 Hypermetropia Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
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- 239000006184 cosolvent Substances 0.000 description 2
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- 210000000744 eyelid Anatomy 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000003149 muscarinic antagonist Substances 0.000 description 2
- 230000003551 muscarinic effect Effects 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000004515 progressive myopia Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YZPAKBGVJIVPEU-UHFFFAOYSA-N 1,2-benzodiazepin-6-one Chemical compound N1=NC=CC=C2C(=O)C=CC=C21 YZPAKBGVJIVPEU-UHFFFAOYSA-N 0.000 description 1
- WWJHRSCUAQPFQO-UHFFFAOYSA-M 4-DAMP methiodide Chemical compound [I-].C1C[N+](C)(C)CCC1OC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 WWJHRSCUAQPFQO-UHFFFAOYSA-M 0.000 description 1
- -1 4-methyl-1-piperazinyl Chemical group 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000937413 Axia Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical compound O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 description 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 1
- 102100023170 Nuclear receptor subfamily 1 group D member 1 Human genes 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010038848 Retinal detachment Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
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- 239000003929 acidic solution Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 229940092732 belladonna alkaloid Drugs 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 229960001815 cyclopentolate Drugs 0.000 description 1
- SKYSRIRYMSLOIN-UHFFFAOYSA-N cyclopentolate Chemical compound C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 SKYSRIRYMSLOIN-UHFFFAOYSA-N 0.000 description 1
- 201000000255 cycloplegia Diseases 0.000 description 1
- 230000003500 cycloplegic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 230000000857 drug effect Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000004305 hyperopia Effects 0.000 description 1
- 201000006318 hyperopia Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
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- 208000014674 injury Diseases 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
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- 230000004423 myopia development Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 230000004264 retinal detachment Effects 0.000 description 1
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- 210000002460 smooth muscle Anatomy 0.000 description 1
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- 238000000935 solvent evaporation Methods 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
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Classifications
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82349592A | 1992-01-21 | 1992-01-21 | |
| US823,495 | 1992-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2087510A1 true CA2087510A1 (en) | 1993-07-22 |
Family
ID=25238929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002087510A Abandoned CA2087510A1 (en) | 1992-01-21 | 1993-01-18 | Method of using m1-selective antimuscarinic pyridobenzodiazepiones in axial myopia therapy |
Country Status (10)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5122522A (en) * | 1989-06-21 | 1992-06-16 | The Trustees Of The University Of Pennsylvania | Treatment and control of ocular development |
| US6710051B1 (en) * | 1997-01-06 | 2004-03-23 | Klaus Trier Aps | Screening method |
| US9827250B2 (en) * | 2012-07-31 | 2017-11-28 | Johnson & Johnson Vision Care, Inc. | Lens incorporating myopia control optics and muscarinic agents |
| JP6784407B2 (ja) * | 2015-04-24 | 2020-11-11 | 学校法人慶應義塾 | 近視予防剤及び近視進行抑制剤 |
| GB201510010D0 (en) | 2015-06-09 | 2015-07-22 | King S College London | PDD and BPD compounds |
| GB201514928D0 (en) | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| US10845622B2 (en) | 2015-09-15 | 2020-11-24 | Largan Medical Co., Ltd. | Multifocal contact lens and contact lens product |
| CN110308571B (zh) | 2015-09-15 | 2024-01-30 | 星欧光学股份有限公司 | 隐形眼镜产品 |
| US12298602B2 (en) | 2015-09-15 | 2025-05-13 | Largan Medical Co., Ltd. | Multifocal contact lens and contact lens product |
| CN115414357B (zh) * | 2022-08-30 | 2023-09-22 | 天津医科大学眼科医院 | 一种酰胺类化合物在制备防治近视的药物中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1212742B (it) * | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Derivati dibenzo [1,4]diazepinonici pirido [1,4] benzodiazepinonici,pirido [1,5] benzodiazepinonici e loro attivita' farmacologica |
| CA2058768C (en) * | 1989-06-21 | 2004-08-03 | Alan M. Laties | Treatment and control of ocular development |
-
1993
- 1993-01-12 WO PCT/US1993/000241 patent/WO1993013777A1/en not_active Application Discontinuation
- 1993-01-14 EP EP93300208A patent/EP0556947A1/en not_active Withdrawn
- 1993-01-15 IL IL104409A patent/IL104409A0/xx unknown
- 1993-01-18 CA CA002087510A patent/CA2087510A1/en not_active Abandoned
- 1993-01-18 TW TW082100297A patent/TW222583B/zh active
- 1993-01-18 JP JP5005813A patent/JPH0742231B2/ja not_active Expired - Lifetime
- 1993-01-20 CN CN93100697A patent/CN1074606A/zh active Pending
- 1993-01-20 ZA ZA93374A patent/ZA93374B/xx unknown
- 1993-01-20 ZA ZA1993374A patent/ZA93384B/xx unknown
- 1993-01-20 AU AU31923/93A patent/AU3192393A/en not_active Abandoned
- 1993-01-20 MX MX9300250A patent/MX9300250A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9300250A (es) | 1993-07-01 |
| EP0556947A1 (en) | 1993-08-25 |
| CN1074606A (zh) | 1993-07-28 |
| WO1993013777A1 (en) | 1993-07-22 |
| ZA93374B (en) | 1993-08-23 |
| JPH06206820A (ja) | 1994-07-26 |
| ZA93384B (en) | 1993-08-23 |
| AU3192393A (en) | 1993-07-22 |
| TW222583B (enrdf_load_html_response) | 1994-04-21 |
| JPH0742231B2 (ja) | 1995-05-10 |
| IL104409A0 (en) | 1993-05-13 |
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