JP6820847B2 - プロスタグランジンと一酸化窒素供与体との組み合わせ - Google Patents
プロスタグランジンと一酸化窒素供与体との組み合わせ Download PDFInfo
- Publication number
- JP6820847B2 JP6820847B2 JP2017526551A JP2017526551A JP6820847B2 JP 6820847 B2 JP6820847 B2 JP 6820847B2 JP 2017526551 A JP2017526551 A JP 2017526551A JP 2017526551 A JP2017526551 A JP 2017526551A JP 6820847 B2 JP6820847 B2 JP 6820847B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- hydroxyhexahydroflo
- nitrooxy
- furan
- bis
- 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 - Fee Related
Links
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims description 60
- 150000003180 prostaglandins Chemical class 0.000 title description 10
- 239000002840 nitric oxide donor Substances 0.000 title description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 60
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 36
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 33
- 230000004410 intraocular pressure Effects 0.000 claims description 33
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical class O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 claims description 24
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 claims description 24
- 229960002368 travoprost Drugs 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 150000003169 prostaglandin F2α derivatives Chemical class 0.000 claims description 22
- -1 furan-3-yl 4- (nitrooxy) butyl Chemical group 0.000 claims description 20
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 18
- 229960002470 bimatoprost Drugs 0.000 claims description 13
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 claims description 13
- 208000010412 Glaucoma Diseases 0.000 claims description 12
- 229960001160 latanoprost Drugs 0.000 claims description 9
- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 claims description 9
- 229960004458 tafluprost Drugs 0.000 claims description 7
- WSNODXPBBALQOF-VEJSHDCNSA-N tafluprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1 WSNODXPBBALQOF-VEJSHDCNSA-N 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229950008081 unoprostone isopropyl Drugs 0.000 claims description 6
- XXUPXHKCPIKWLR-JHUOEJJVSA-N isopropyl unoprostone Chemical compound CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)OC(C)C XXUPXHKCPIKWLR-JHUOEJJVSA-N 0.000 claims description 5
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims description 3
- SNPDKBFMQHFHFY-UHFFFAOYSA-N 3-(2,3-dinitrooxypropoxy)propanoic acid Chemical compound OC(=O)CCOCC(O[N+]([O-])=O)CO[N+]([O-])=O SNPDKBFMQHFHFY-UHFFFAOYSA-N 0.000 claims description 3
- ZETOHPSSBWBMED-UHFFFAOYSA-N 4-nitrooxybutanoic acid Chemical compound OC(=O)CCCO[N+]([O-])=O ZETOHPSSBWBMED-UHFFFAOYSA-N 0.000 claims description 3
- 206010030043 Ocular hypertension Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 208000022873 Ocular disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 0 **OC[C@](CO[C@@]12)[C@@]1OC[C@]2O Chemical compound **OC[C@](CO[C@@]12)[C@@]1OC[C@]2O 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- KPSZWAJWFMFMFF-UHFFFAOYSA-N delta-Hexylen-alpha-carbonsaeure Natural products CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 description 4
- KPSZWAJWFMFMFF-NSCUHMNNSA-N delta-heptenoic acid Chemical group C\C=C\CCCC(O)=O KPSZWAJWFMFMFF-NSCUHMNNSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- PRGUDWLMFLCODA-UHFFFAOYSA-N oxybuprocaine hydrochloride Chemical compound [Cl-].CCCCOC1=CC(C(=O)OCC[NH+](CC)CC)=CC=C1N PRGUDWLMFLCODA-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 206010018307 Glaucoma and ocular hypertension Diseases 0.000 description 3
- 208000030533 eye disease Diseases 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 210000001742 aqueous humor Anatomy 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 238000009530 blood pressure measurement Methods 0.000 description 2
- 238000011260 co-administration Methods 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 238000011587 new zealand white rabbit Methods 0.000 description 2
- 230000004493 normal intraocular pressure Effects 0.000 description 2
- 239000008217 ophthalmic excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000004393 visual impairment Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 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 1
- XYLJNLCSTIOKRM-UHFFFAOYSA-N Alphagan Chemical compound C1=CC2=NC=CN=C2C(Br)=C1NC1=NCCN1 XYLJNLCSTIOKRM-UHFFFAOYSA-N 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010051625 Conjunctival hyperaemia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010067013 Normal tension glaucoma Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229960003679 brimonidine Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- KDZMEZRLDMNVMZ-UHFFFAOYSA-N hept-5-enamide Chemical group CC=CCCCC(N)=O KDZMEZRLDMNVMZ-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000002978 low tension glaucoma Diseases 0.000 description 1
- 230000000938 luteal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
- 210000001328 optic nerve Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 229940083618 sodium nitroprusside Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 210000004127 vitreous body Anatomy 0.000 description 1
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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14193883.7 | 2014-11-19 | ||
| EP14193883 | 2014-11-19 | ||
| PCT/EP2015/076865 WO2016079142A1 (en) | 2014-11-19 | 2015-11-17 | Combinations of prostaglandins and nitric oxide donors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017534658A JP2017534658A (ja) | 2017-11-24 |
| JP2017534658A5 JP2017534658A5 (enExample) | 2018-12-20 |
| JP6820847B2 true JP6820847B2 (ja) | 2021-01-27 |
Family
ID=51904805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017526551A Expired - Fee Related JP6820847B2 (ja) | 2014-11-19 | 2015-11-17 | プロスタグランジンと一酸化窒素供与体との組み合わせ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10610509B2 (enExample) |
| EP (1) | EP3220905B1 (enExample) |
| JP (1) | JP6820847B2 (enExample) |
| CN (1) | CN106999452B (enExample) |
| CA (1) | CA2968010A1 (enExample) |
| ES (1) | ES2764654T3 (enExample) |
| WO (1) | WO2016079142A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019121488A1 (en) * | 2017-12-21 | 2019-06-27 | Nicox S.A. | Nitric oxide releasing hyaluronic esters |
| KR102836746B1 (ko) | 2018-08-06 | 2025-07-21 | 니콕스 에스아 | 산화질소 방출 포스포디에스테라제 타입 5 억제제 |
| JP7708771B2 (ja) * | 2020-02-05 | 2025-07-15 | ニコックス エス．エー． | 緑内障及び高眼圧症の処置のための組成物 |
| CN118084895B (zh) * | 2024-02-28 | 2025-09-05 | 中国药科大学 | 一种一氧化氮供体型Omidenepag衍生物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002085372A1 (en) * | 2001-04-19 | 2002-10-31 | Teika Pharmaceutical Co., Ltd. | Medicines and medicinal kits |
| WO2009098113A1 (en) * | 2008-02-07 | 2009-08-13 | Nicox S.A. | Nitric oxide donor compounds |
| EP2911656B1 (en) * | 2012-10-23 | 2020-12-02 | Nicox SA | Quinone based nitric oxide donating compounds for ophthalmic use |
-
2015
- 2015-11-17 CN CN201580062042.0A patent/CN106999452B/zh not_active Expired - Fee Related
- 2015-11-17 JP JP2017526551A patent/JP6820847B2/ja not_active Expired - Fee Related
- 2015-11-17 US US15/527,129 patent/US10610509B2/en not_active Expired - Fee Related
- 2015-11-17 WO PCT/EP2015/076865 patent/WO2016079142A1/en not_active Ceased
- 2015-11-17 ES ES15801709T patent/ES2764654T3/es active Active
- 2015-11-17 EP EP15801709.5A patent/EP3220905B1/en not_active Not-in-force
- 2015-11-17 CA CA2968010A patent/CA2968010A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20170354634A1 (en) | 2017-12-14 |
| ES2764654T3 (es) | 2020-06-04 |
| US10610509B2 (en) | 2020-04-07 |
| WO2016079142A1 (en) | 2016-05-26 |
| EP3220905B1 (en) | 2019-10-09 |
| CA2968010A1 (en) | 2016-05-26 |
| EP3220905A1 (en) | 2017-09-27 |
| JP2017534658A (ja) | 2017-11-24 |
| CN106999452A (zh) | 2017-08-01 |
| CN106999452B (zh) | 2020-10-16 |
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