KR20150140831A - 페녹시에틸 디히드로-1h-이소퀴놀린 화합물 - Google Patents
페녹시에틸 디히드로-1h-이소퀴놀린 화합물 Download PDFInfo
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- KR20150140831A KR20150140831A KR1020157032468A KR20157032468A KR20150140831A KR 20150140831 A KR20150140831 A KR 20150140831A KR 1020157032468 A KR1020157032468 A KR 1020157032468A KR 20157032468 A KR20157032468 A KR 20157032468A KR 20150140831 A KR20150140831 A KR 20150140831A
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- Prior art keywords
- pharmaceutically acceptable
- compound
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- added
- mixture
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- 239000011521 glass Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XSYGLHLLQZGWPT-UHFFFAOYSA-N methyl 4-(1-aminoethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(C)N)C=C1 XSYGLHLLQZGWPT-UHFFFAOYSA-N 0.000 description 1
- ZIIQWTRFDRIPFB-SCLBCKFNSA-N methyl 4-[(1S)-1-[[(3R)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]amino]ethyl]benzoate Chemical compound C1N[C@H](CC2=CC=CC=C12)C(=O)N[C@@H](C)C1=CC=C(C(=O)OC)C=C1 ZIIQWTRFDRIPFB-SCLBCKFNSA-N 0.000 description 1
- DUSXEGVIXFYWBJ-RXFWQSSRSA-N methyl 4-[(1S)-1-[[(3R)-2-(2-phenoxyethyl)-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]ethyl]benzoate Chemical compound O(C1=CC=CC=C1)CCN1CC2=CC=CC=C2C[C@@H]1C(=O)N[C@@H](C)C1=CC=C(C(=O)OC)C=C1 DUSXEGVIXFYWBJ-RXFWQSSRSA-N 0.000 description 1
- XSYGLHLLQZGWPT-ZETCQYMHSA-N methyl 4-[(1s)-1-aminoethyl]benzoate Chemical compound COC(=O)C1=CC=C([C@H](C)N)C=C1 XSYGLHLLQZGWPT-ZETCQYMHSA-N 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- BLZZOVOIOKSTEZ-XDJLXXALSA-N tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylate Chemical compound COC(=O)C1=CC=C(C=C1)[C@H](C)NC(=O)[C@@H]1NC(C2=CC=CC=C2C1)C(=O)OC(C)(C)C BLZZOVOIOKSTEZ-XDJLXXALSA-N 0.000 description 1
- DNLDTAMVFGDUPV-HRAATJIYSA-N tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound COC(=O)C1=CC=C(C=C1)[C@H](C)NC(=O)[C@@H]1N(CC2=CC=CC=C2C1)C(=O)OC(C)(C)C DNLDTAMVFGDUPV-HRAATJIYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epidemiology (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Description
Claims (14)
- 골관절염의 치료를 필요로 하는 환자에게 유효량의 제1항에 따른 화합물 또는 그의 제약상 허용되는 염을 투여하는 것을 포함하는, 환자에서 골관절염을 치료하는 방법.
- 류마티스 관절염의 치료를 필요로 하는 환자에게 유효량의 제1항에 따른 화합물 또는 그의 제약상 허용되는 염을 투여하는 것을 포함하는, 환자에서 류마티스 관절염을 치료하는 방법.
- 골관절염 또는 류마티스 관절염과 연관된 통증의 치료를 필요로 하는 환자에게 유효량의 제1항에 따른 화합물 또는 그의 제약상 허용되는 염을 투여하는 것을 포함하는, 환자에서 골관절염 또는 류마티스 관절염과 연관된 통증을 치료하는 방법.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 요법에 사용하기 위한 화합물 또는 그의 제약상 허용되는 염.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 골관절염의 치료에 사용하기 위한 화합물 또는 그의 제약상 허용되는 염.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 류마티스 관절염의 치료에 사용하기 위한 화합물 또는 그의 제약상 허용되는 염.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 골관절염 또는 류마티스 관절염과 연관된 통증의 치료에 사용하기 위한 화합물 또는 그의 제약상 허용되는 염.
- 제1항 내지 제6항 중 어느 한 항에 따른 화합물 또는 그의 제약상 허용되는 염을 1종 이상의 제약상 허용되는 담체, 희석제 또는 부형제와 함께 포함하는 제약 조성물.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361824436P | 2013-05-17 | 2013-05-17 | |
US61/824,436 | 2013-05-17 | ||
PCT/US2014/037416 WO2014186218A1 (en) | 2013-05-17 | 2014-05-09 | Phenoxyethyl dihydro-1h-isoquinoline compounds |
Publications (2)
Publication Number | Publication Date |
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KR20150140831A true KR20150140831A (ko) | 2015-12-16 |
KR101798315B1 KR101798315B1 (ko) | 2017-11-15 |
Family
ID=50877688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1020157032468A Active KR101798315B1 (ko) | 2013-05-17 | 2014-05-09 | 페녹시에틸 디히드로-1h-이소퀴놀린 화합물 |
Country Status (17)
Country | Link |
---|---|
US (1) | US9371289B2 (ko) |
EP (1) | EP2997015B1 (ko) |
JP (1) | JP6148400B2 (ko) |
KR (1) | KR101798315B1 (ko) |
CN (1) | CN105209438B (ko) |
BR (1) | BR112015026967B1 (ko) |
CA (1) | CA2908400C (ko) |
EA (1) | EA027306B1 (ko) |
ES (1) | ES2626976T3 (ko) |
HU (1) | HUE033574T2 (ko) |
MX (1) | MX2015015841A (ko) |
PL (1) | PL2997015T3 (ko) |
PT (1) | PT2997015T (ko) |
SA (1) | SA515370035B1 (ko) |
TW (1) | TWI636046B (ko) |
WO (1) | WO2014186218A1 (ko) |
ZA (1) | ZA201507566B (ko) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EA028921B1 (ru) * | 2013-12-17 | 2018-01-31 | Эли Лилли Энд Компани | Феноксиэтилы |
CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
AU2018269666B2 (en) | 2017-05-18 | 2022-02-03 | Idorsia Pharmaceuticals Ltd | Phenyl derivatives as PGE2 receptor modulators |
EP3625223B1 (en) | 2017-05-18 | 2021-08-11 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives |
WO2018210988A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives as pge2 receptor modulators |
PT3625224T (pt) | 2017-05-18 | 2021-10-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-substituídos |
WO2018210987A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Benzofurane and benzothiophene derivatives as pge2 receptor modulators |
WO2022102731A1 (ja) | 2020-11-13 | 2022-05-19 | 小野薬品工業株式会社 | Ep4拮抗薬と免疫チェックポイント阻害物質との併用によるがん治療 |
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DE2500157C2 (de) | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
IT1270615B (it) | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
US6649606B1 (en) * | 2001-11-09 | 2003-11-18 | Bristol-Myers Squibb Co. | Tetrahydroisoquinoline analogs as modulators of chemokine receptor activity |
CA2465090C (en) | 2001-11-09 | 2010-02-02 | Enzon, Inc. | Polymeric thiol-linked prodrugs employing benzyl elimination systems |
EP1558253A4 (en) * | 2002-10-30 | 2007-07-25 | Merck & Co Inc | PIPERIDINYL ALPHA AMINOAMIDE MODULATORS DERCHEMOKIN RECEPTOR ACTIVITY |
EP1660439A2 (en) * | 2003-08-08 | 2006-05-31 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
AP2006003534A0 (en) | 2003-09-03 | 2006-04-30 | Pfizer | Phenyl or pyridyl amide compounds as prostaglandin E2 antagonists. |
KR20070006891A (ko) | 2004-05-04 | 2007-01-11 | 화이자 인코포레이티드 | 치환된 메틸 아릴 또는 헤테로아릴 아미드 화합물 |
KR20070006890A (ko) | 2004-05-04 | 2007-01-11 | 화이자 인코포레이티드 | 오르토 치환된 아릴 또는 헤테로아릴 아마이드 화합물 |
US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
WO2007121578A1 (en) | 2006-04-24 | 2007-11-01 | Merck Frosst Canada Ltd. | Indole amide derivatives as ep4 receptor antagonists |
JP5183628B2 (ja) | 2006-06-12 | 2013-04-17 | メルク カナダ インコーポレイテッド | Ep4受容体リガンドとしてのインドリンアミド誘導体 |
AU2009247262B2 (en) * | 2008-05-14 | 2013-01-31 | Astellas Pharma Inc. | Amide compound |
WO2010019796A1 (en) | 2008-08-14 | 2010-02-18 | Chemietek, Llc | Heterocyclic amide derivatives as ep4 receptor antagonists |
EP2538978B1 (en) | 2010-02-22 | 2016-09-07 | RaQualia Pharma Inc. | Use of an ep4 receptor antagonist in the treatment of allergic contact dermatitis and psoriasis |
CA2839116C (en) * | 2011-07-04 | 2019-07-16 | Rottapharm S.P.A. | Cyclic amine derivatives as ep4 receptor antagonists |
ES2564353T3 (es) | 2011-07-04 | 2016-03-22 | Rottapharm Biotech S.R.L. | Derivados de aminas cíclicas como agonistas de los receptores EP4 |
EP2572746A1 (en) * | 2011-09-23 | 2013-03-27 | Sanofi-Aventis Deutschland GmbH | Needle safety device |
AR091429A1 (es) | 2012-06-29 | 2015-02-04 | Lilly Co Eli | Compuestos de fenoxietil piperidina |
TWI572597B (zh) | 2012-06-29 | 2017-03-01 | 美國禮來大藥廠 | 二甲基-苯甲酸化合物 |
-
2014
- 2014-05-02 TW TW103115871A patent/TWI636046B/zh active
- 2014-05-09 CA CA2908400A patent/CA2908400C/en active Active
- 2014-05-09 MX MX2015015841A patent/MX2015015841A/es active IP Right Grant
- 2014-05-09 EA EA201591915A patent/EA027306B1/ru not_active IP Right Cessation
- 2014-05-09 PT PT147276927T patent/PT2997015T/pt unknown
- 2014-05-09 ES ES14727692.7T patent/ES2626976T3/es active Active
- 2014-05-09 CN CN201480028163.9A patent/CN105209438B/zh active Active
- 2014-05-09 US US14/888,497 patent/US9371289B2/en active Active
- 2014-05-09 EP EP14727692.7A patent/EP2997015B1/en active Active
- 2014-05-09 BR BR112015026967-2A patent/BR112015026967B1/pt active IP Right Grant
- 2014-05-09 HU HUE14727692A patent/HUE033574T2/hu unknown
- 2014-05-09 KR KR1020157032468A patent/KR101798315B1/ko active Active
- 2014-05-09 PL PL14727692T patent/PL2997015T3/pl unknown
- 2014-05-09 WO PCT/US2014/037416 patent/WO2014186218A1/en active Application Filing
- 2014-05-09 JP JP2016513099A patent/JP6148400B2/ja active Active
-
2015
- 2015-10-12 ZA ZA2015/07566A patent/ZA201507566B/en unknown
- 2015-10-22 SA SA515370035A patent/SA515370035B1/ar unknown
Also Published As
Publication number | Publication date |
---|---|
WO2014186218A1 (en) | 2014-11-20 |
SA515370035B1 (ar) | 2018-01-04 |
AU2014265762A1 (en) | 2015-10-15 |
BR112015026967B1 (pt) | 2023-01-10 |
EP2997015A1 (en) | 2016-03-23 |
ES2626976T3 (es) | 2017-07-26 |
ZA201507566B (en) | 2017-06-28 |
CA2908400C (en) | 2017-04-11 |
CN105209438A (zh) | 2015-12-30 |
JP6148400B2 (ja) | 2017-06-14 |
EP2997015B1 (en) | 2017-04-05 |
CA2908400A1 (en) | 2014-11-20 |
JP2016519140A (ja) | 2016-06-30 |
US9371289B2 (en) | 2016-06-21 |
BR112015026967A8 (pt) | 2018-01-30 |
CN105209438B (zh) | 2017-04-12 |
PL2997015T3 (pl) | 2017-09-29 |
EA027306B1 (ru) | 2017-07-31 |
HUE033574T2 (hu) | 2017-12-28 |
US20160052889A1 (en) | 2016-02-25 |
EA201591915A1 (ru) | 2016-04-29 |
KR101798315B1 (ko) | 2017-11-15 |
MX2015015841A (es) | 2016-03-04 |
PT2997015T (pt) | 2017-04-24 |
TWI636046B (zh) | 2018-09-21 |
BR112015026967A2 (pt) | 2017-07-25 |
TW201534588A (zh) | 2015-09-16 |
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