JP2019501126A5 - - Google Patents
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- Publication number
- JP2019501126A5 JP2019501126A5 JP2018525670A JP2018525670A JP2019501126A5 JP 2019501126 A5 JP2019501126 A5 JP 2019501126A5 JP 2018525670 A JP2018525670 A JP 2018525670A JP 2018525670 A JP2018525670 A JP 2018525670A JP 2019501126 A5 JP2019501126 A5 JP 2019501126A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydronaphthalen
- dioxo
- chloro
- benzamide
- 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.)
- Granted
Links
- -1 NH 2 Inorganic materials 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 18
- 239000003814 drug Substances 0.000 claims 16
- 229940079593 drug Drugs 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 230000003510 anti-fibrotic effect Effects 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 4
- 229960003073 pirfenidone Drugs 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 102100031168 CCN family member 2 Human genes 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 101000777550 Homo sapiens CCN family member 2 Proteins 0.000 claims 2
- 101001043352 Homo sapiens Lysyl oxidase homolog 2 Proteins 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 102100021948 Lysyl oxidase homolog 2 Human genes 0.000 claims 2
- 239000000443 aerosol Substances 0.000 claims 2
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 229950002183 lebrikizumab Drugs 0.000 claims 2
- XZXHXSATPCNXJR-ZIADKAODSA-N nintedanib Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 XZXHXSATPCNXJR-ZIADKAODSA-N 0.000 claims 2
- 229960004378 nintedanib Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- LPJPITLQDACBTI-UHFFFAOYSA-N ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 Chemical compound ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 LPJPITLQDACBTI-UHFFFAOYSA-N 0.000 claims 1
- FEHBRQORVLVXCA-UHFFFAOYSA-N ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2CC2)C=C1 Chemical compound ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2CC2)C=C1 FEHBRQORVLVXCA-UHFFFAOYSA-N 0.000 claims 1
- CITYFCJXIKTFJS-UHFFFAOYSA-N ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2CCCC2)C=C1 Chemical compound ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NC2CCCC2)C=C1 CITYFCJXIKTFJS-UHFFFAOYSA-N 0.000 claims 1
- MYRFDYAPNJFZOM-UHFFFAOYSA-N ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NO)C=C1 Chemical compound ClC1=C(C(C2=CC=CC=C2C1=O)=O)NCC1=CC=C(C(=O)NO)C=C1 MYRFDYAPNJFZOM-UHFFFAOYSA-N 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010019668 Hepatic fibrosis Diseases 0.000 claims 1
- 206010072877 Intestinal fibrosis Diseases 0.000 claims 1
- HHFFMRCWVFIRPN-UHFFFAOYSA-N NC1=NN(C(=C1)C)C(=O)C1=CC=C(CNC=2C(C3=CC=CC=C3C(C=2Cl)=O)=O)C=C1 Chemical compound NC1=NN(C(=C1)C)C(=O)C1=CC=C(CNC=2C(C3=CC=CC=C3C(C=2Cl)=O)=O)C=C1 HHFFMRCWVFIRPN-UHFFFAOYSA-N 0.000 claims 1
- MXFPLPCWUNTGQU-UHFFFAOYSA-N NC1=NN(C=C1)C(=O)C1=CC=C(CNC=2C(C3=CC=CC=C3C(C=2Cl)=O)=O)C=C1 Chemical compound NC1=NN(C=C1)C(=O)C1=CC=C(CNC=2C(C3=CC=CC=C3C(C=2Cl)=O)=O)C=C1 MXFPLPCWUNTGQU-UHFFFAOYSA-N 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005237 alkyleneamino group Chemical group 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000011260 co-administration Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000002500 effect on skin Effects 0.000 claims 1
- 201000009274 endometriosis of uterus Diseases 0.000 claims 1
- 230000003176 fibrotic effect Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002639 hyperbaric oxygen therapy Methods 0.000 claims 1
- 201000010260 leiomyoma Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000005475 oxolanyl group Chemical group 0.000 claims 1
- 238000002640 oxygen therapy Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 229950009513 simtuzumab Drugs 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000005458 thianyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001166 thiolanyl group Chemical group 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 201000007954 uterine fibroid Diseases 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 2
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- XBTOSRUBOXQWBO-UHFFFAOYSA-N 1h-indazol-5-amine Chemical compound NC1=CC=C2NN=CC2=C1 XBTOSRUBOXQWBO-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- COCFIBRMFPWUDW-UHFFFAOYSA-N 2-methylquinolin-4-amine Chemical compound C1=CC=CC2=NC(C)=CC(N)=C21 COCFIBRMFPWUDW-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022092059A JP7667764B2 (ja) | 2015-11-17 | 2022-06-07 | 線維症疾患の治療及び／又は予防用アミノナフトキノン化合物 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562256516P | 2015-11-17 | 2015-11-17 | |
| US62/256,516 | 2015-11-17 | ||
| PCT/US2016/062568 WO2017087695A1 (en) | 2015-11-17 | 2016-11-17 | Aminonaphthoquinone compounds for treatment and/or prevention of fibrosis diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022092059A Division JP7667764B2 (ja) | 2015-11-17 | 2022-06-07 | 線維症疾患の治療及び／又は予防用アミノナフトキノン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019501126A JP2019501126A (ja) | 2019-01-17 |
| JP2019501126A5 true JP2019501126A5 (enExample) | 2019-12-26 |
| JP7085994B2 JP7085994B2 (ja) | 2022-06-17 |
Family
ID=58717862
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018525670A Active JP7085994B2 (ja) | 2015-11-17 | 2016-11-17 | 線維症疾患の治療及び／又は予防用アミノナフトキノン化合物 |
| JP2022092059A Active JP7667764B2 (ja) | 2015-11-17 | 2022-06-07 | 線維症疾患の治療及び／又は予防用アミノナフトキノン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022092059A Active JP7667764B2 (ja) | 2015-11-17 | 2022-06-07 | 線維症疾患の治療及び／又は予防用アミノナフトキノン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US11833122B2 (enExample) |
| EP (1) | EP3377062B1 (enExample) |
| JP (2) | JP7085994B2 (enExample) |
| KR (1) | KR20180096609A (enExample) |
| CN (2) | CN120204220A (enExample) |
| ES (1) | ES2955665T3 (enExample) |
| TW (1) | TWI673049B (enExample) |
| WO (1) | WO2017087695A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112074505B (zh) | 2018-03-08 | 2024-04-05 | 因赛特公司 | 作为PI3K-γ抑制剂的氨基吡嗪二醇化合物 |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| KR20240159339A (ko) * | 2023-04-28 | 2024-11-05 | 한국원자력의학원 | 폐섬유화 예방 또는 치료를 위한 다코미티닙 및 닌테다닙의 병용 요법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040167189A1 (en) * | 2002-03-22 | 2004-08-26 | The Government Of The U.S.A., As Represented By The Secretary, Dept. Of Health And Human Services | Materials and methods for inhibiting Wip1 |
| EP1524988B1 (de) * | 2002-07-25 | 2008-04-16 | Charite-Universitätsmedizin Berlin | Verwendung eines proteasom-inhibitors zur behandlung fibrotischer erkrankungen |
| CA2565407A1 (en) | 2004-05-10 | 2005-11-24 | Proteolix, Inc. | Compounds for enzyme inhibition |
| ES2549763T3 (es) | 2004-12-07 | 2015-11-02 | Onyx Therapeutics, Inc. | Composición para inhibición del proteasoma |
| US8673910B2 (en) * | 2008-06-30 | 2014-03-18 | H. Lee Moffitt Cancer Center And Research Institute | Proteasome inhibitors for selectively inducing apoptosis in cancer cells |
| JP6820313B2 (ja) * | 2015-07-23 | 2021-01-27 | カルジェント バイオテクノロジー カンパニー， リミテッド | アミノナフトキノン化合物、および疾患におけるユビキチン化−プロテアソーム系をブロックするための薬学的組成物 |
| US10745350B2 (en) * | 2015-07-30 | 2020-08-18 | Calgent Biotechnology Co., Ltd. | Compounds and pharmaceutical composition associated with ubiquitination-proteasome system |
-
2016
- 2016-11-17 EP EP16867152.7A patent/EP3377062B1/en active Active
- 2016-11-17 CN CN202510406652.3A patent/CN120204220A/zh active Pending
- 2016-11-17 ES ES16867152T patent/ES2955665T3/es active Active
- 2016-11-17 TW TW105137577A patent/TWI673049B/zh active
- 2016-11-17 WO PCT/US2016/062568 patent/WO2017087695A1/en not_active Ceased
- 2016-11-17 US US15/776,698 patent/US11833122B2/en active Active
- 2016-11-17 CN CN201680067312.1A patent/CN108697697A/zh active Pending
- 2016-11-17 JP JP2018525670A patent/JP7085994B2/ja active Active
- 2016-11-17 KR KR1020187016101A patent/KR20180096609A/ko not_active Ceased
-
2022
- 2022-06-07 JP JP2022092059A patent/JP7667764B2/ja active Active
-
2023
- 2023-10-23 US US18/492,627 patent/US12453708B2/en active Active
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