UA112667C2 - Комбінація антагоніста crth2 і інгібітору протонного насоса для лікування еозинофільного езофагіту - Google Patents
Комбінація антагоніста crth2 і інгібітору протонного насоса для лікування еозинофільного езофагіту Download PDFInfo
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- UA112667C2 UA112667C2 UAA201407393A UAA201407393A UA112667C2 UA 112667 C2 UA112667 C2 UA 112667C2 UA A201407393 A UAA201407393 A UA A201407393A UA A201407393 A UAA201407393 A UA A201407393A UA 112667 C2 UA112667 C2 UA 112667C2
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- UA
- Ukraine
- Prior art keywords
- methyl
- acetic acid
- fluoro
- indol
- methylindol
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- 206010064212 Eosinophilic oesophagitis Diseases 0.000 title claims abstract description 40
- 201000000708 eosinophilic esophagitis Diseases 0.000 title claims abstract description 40
- 229940126409 proton pump inhibitor Drugs 0.000 title claims abstract description 20
- 239000000612 proton pump inhibitor Substances 0.000 title claims abstract description 20
- 238000011282 treatment Methods 0.000 title claims abstract description 20
- 229940124003 CRTH2 antagonist Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract description 137
- 229960004770 esomeprazole Drugs 0.000 claims abstract description 25
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 claims abstract description 25
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims abstract description 22
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- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims abstract description 22
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- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims abstract description 22
- MJIHNNLFOKEZEW-RUZDIDTESA-N dexlansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1C[S@@](=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-RUZDIDTESA-N 0.000 claims abstract description 21
- 229960003568 dexlansoprazole Drugs 0.000 claims abstract description 21
- 208000024891 symptom Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 587
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 239000005557 antagonist Substances 0.000 claims description 87
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 82
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 77
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 37
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- 239000003246 corticosteroid Substances 0.000 claims description 32
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 27
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- FATGTHLOZSXOBC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 FATGTHLOZSXOBC-UHFFFAOYSA-N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
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- 239000011737 fluorine Substances 0.000 claims description 11
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 8
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
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- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 6
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- 101100352202 Arabidopsis thaliana PIGA gene Proteins 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
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- AUHRDYPGCRKIKZ-UHFFFAOYSA-N 2-[2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 AUHRDYPGCRKIKZ-UHFFFAOYSA-N 0.000 claims description 3
- VHZQRDXTXVSINR-UHFFFAOYSA-N 2-[3-[(2-benzylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1 VHZQRDXTXVSINR-UHFFFAOYSA-N 0.000 claims description 3
- BRNIUXLBABJPPA-UHFFFAOYSA-N 2-[3-[(4-benzylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=CC=C1 BRNIUXLBABJPPA-UHFFFAOYSA-N 0.000 claims description 3
- RCDLAJQERQUBRP-UHFFFAOYSA-N 2-[3-[[4-[(4-chlorophenyl)methylsulfonyl]phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=C(Cl)C=C1 RCDLAJQERQUBRP-UHFFFAOYSA-N 0.000 claims description 3
- QILUMBJCLHPTEK-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 QILUMBJCLHPTEK-UHFFFAOYSA-N 0.000 claims description 3
- PAKMLKICQKNIQV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-pyrrolidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)N1CCCC1 PAKMLKICQKNIQV-UHFFFAOYSA-N 0.000 claims description 3
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- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 3
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Classifications
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- 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
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
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- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
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- C—CHEMISTRY; METALLURGY
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- C07K16/18—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
- C07K16/24—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against cytokines, lymphokines or interferons
- C07K16/244—Interleukins [IL]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Molecular Biology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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| US201161576640P | 2011-12-16 | 2011-12-16 | |
| PCT/GB2012/000904 WO2013088109A1 (en) | 2011-12-16 | 2012-12-14 | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
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| US7608693B2 (en) | 2006-10-02 | 2009-10-27 | Regeneron Pharmaceuticals, Inc. | High affinity human antibodies to human IL-4 receptor |
| GB201103837D0 (en) | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| GB201121557D0 (en) | 2011-12-15 | 2012-01-25 | Oxagen Ltd | Process |
| KR102307248B1 (ko) | 2012-08-21 | 2021-10-01 | 사노피 바이오테크놀로지 | Il-4r 길항제의 투여에 의한 천식의 치료 또는 예방 방법 |
| NZ630178A (en) | 2012-09-07 | 2017-06-30 | Regeneron Pharma | Methods for treating atopic dermatitis by administering an il-4r antagonist |
| TWI755763B (zh) | 2013-06-04 | 2022-02-21 | 美商再生元醫藥公司 | 藉由投與il-4r抑制劑以治療過敏及增強過敏原-特異之免疫療法的方法 |
| MX368068B (es) | 2013-06-21 | 2019-09-18 | Sanofi Biotechnology | Antagonista de il-4r para usarse para tratar la poliposis nasal. |
| TWI682781B (zh) | 2013-07-11 | 2020-01-21 | 美商再生元醫藥公司 | 藉由投與ｉｌ－４ｒ抑制劑治療嗜酸性食道炎的方法 |
| WO2015034678A2 (en) | 2013-09-06 | 2015-03-12 | Aptalis Pharmatech, Inc. | Corticosteroid containing orally disintegrating tablet compositions for eosinophilic esophagitis |
| KR20160120735A (ko) | 2014-02-28 | 2016-10-18 | 리제너론 파아마슈티컬스, 인크. | Ｉｌ-4ｒ 길항제의 투여에 의한 피부 감염의 치료 방법 |
| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| CA2967602C (en) | 2014-11-14 | 2024-09-24 | Regeneron Pharmaceuticals, Inc. | METHODS OF TREATMENT OF CHRONIC SINUSITIS WITH NASAL POLYPOSIS BY ADMINISTRATION OF AN IL-4R ANTAGONIST |
| JP6770522B2 (ja) | 2015-02-13 | 2020-10-14 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 全身性エリテマトーデスを予防し、及び／又は、治療するためのｐｔｇｄｒ−１及び／又はｐｔｇｄｒ−２アンタゴニスト |
| EP3402572B1 (en) * | 2016-01-13 | 2022-03-16 | Children's Hospital Medical Center | Compositions and methods for treating allergic inflammatory conditions |
| EP3489233B1 (en) | 2016-07-21 | 2022-01-12 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Indole derivative used as crth2 inhibitor |
| TWI777515B (zh) | 2016-08-18 | 2022-09-11 | 美商愛戴爾製藥股份有限公司 | 治療嗜伊紅性食道炎之方法 |
| US11771743B2 (en) | 2016-09-01 | 2023-10-03 | Regeneron Pharmaceuticals, Inc. | Methods for preventing or treating allergy by administering an IL-4R antagonist |
| US10485844B2 (en) | 2016-09-22 | 2019-11-26 | Regeneron Pharmaceuticals, Inc. | Methods for treating severe atopic dermatitis by administering an IL-4R inhibitor |
| WO2019028367A1 (en) | 2017-08-04 | 2019-02-07 | Regeneron Pharmaceuticals, Inc. | METHODS OF TREATING ESOPHAGITIS WITH ACTIVE EOSINOPHILES |
| EP4344706A3 (en) | 2017-10-30 | 2024-05-22 | Sanofi Biotechnology | Methods for treating or preventing asthma by administering an il-4r antagonist |
| CN107987066B (zh) * | 2017-11-30 | 2020-06-26 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚衍生物 |
| CN107987072B (zh) * | 2017-11-30 | 2020-06-26 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚类化合物 |
| CN107954995B (zh) * | 2017-11-30 | 2020-05-05 | 正大天晴药业集团股份有限公司 | 具有crth2抑制剂活性的吲哚衍生物 |
| CN107936004B (zh) * | 2017-11-30 | 2020-05-05 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚类衍生物 |
| US11859250B1 (en) | 2018-02-23 | 2024-01-02 | Children's Hospital Medical Center | Methods for treating eosinophilic esophagitis |
| EP3781588B1 (en) | 2018-04-20 | 2024-10-30 | Children's Hospital Medical Center | Blood biomarker for eosinophilic gastrointestinal disorders |
| CN120227453A (zh) | 2018-05-13 | 2025-07-01 | 瑞泽恩制药公司 | 用于通过施用il-4r抑制剂治疗特应性皮炎的方法 |
| US12297501B2 (en) | 2019-02-25 | 2025-05-13 | Children's Hospital Medical Center | Methods for diagnosing and treating eosinophilic gastritis |
| KR20210143246A (ko) | 2019-03-21 | 2021-11-26 | 리제너론 파아마슈티컬스, 인크. | 알레르기 치료용 il-4/il-13 경로 억제제 및 형질 세포 절제의 병용 |
| BR112022000740A2 (pt) | 2019-07-16 | 2022-07-05 | Sanofi Biotechnology | Métodos para tratamento ou prevenção de asma por administração de um antagonista de il-4r |
| EP4010373A1 (en) | 2019-08-05 | 2022-06-15 | Regeneron Pharmaceuticals, Inc. | Methods for treating atopic dermatitis by administering an il-4r antagonist |
| KR20220042217A (ko) | 2019-08-05 | 2022-04-04 | 리제너론 파아마슈티컬스, 인크. | Il-4r 길항제를 투여함에 의해 알레르기를 치료하고 알레르겐-특이적 면역치료요법을 증진시키기 위한 방법 |
| WO2022020464A1 (en) * | 2020-07-21 | 2022-01-27 | Ellodi Pharmaceuticals, L.P. | Modified release rapidly disintegrating compositions of proton pump inhibitors |
| EP4595953A1 (en) * | 2024-01-30 | 2025-08-06 | Dr. Falk Pharma Gmbh | Orally applicable suspension for the treatment of eosinophilic esophagitis in children |
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| TWI289557B (en) | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
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| JPWO2003097042A1 (ja) | 2002-05-16 | 2005-09-15 | 塩野義製薬株式会社 | Ｐｇｄ２受容体拮抗剤 |
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-
2012
- 2012-12-14 WO PCT/GB2012/000904 patent/WO2013088109A1/en not_active Ceased
- 2012-12-14 EP EP12808859.8A patent/EP2790696A1/en not_active Withdrawn
- 2012-12-14 BR BR112014014558A patent/BR112014014558A8/pt not_active Application Discontinuation
- 2012-12-14 UA UAA201407393A patent/UA112667C2/uk unknown
- 2012-12-14 JP JP2014546622A patent/JP2015500326A/ja active Pending
- 2012-12-14 CN CN201280066423.2A patent/CN104114169A/zh active Pending
- 2012-12-14 US US14/365,306 patent/US20140328861A1/en not_active Abandoned
- 2012-12-14 EA EA201491008A patent/EA026456B1/ru unknown
- 2012-12-14 CA CA2859284A patent/CA2859284A1/en not_active Abandoned
- 2012-12-14 KR KR1020147018762A patent/KR20140113667A/ko not_active Withdrawn
- 2012-12-14 MX MX2014007239A patent/MX2014007239A/es unknown
- 2012-12-14 AU AU2012351342A patent/AU2012351342A1/en not_active Abandoned
- 2012-12-14 SG SG11201402796SA patent/SG11201402796SA/en unknown
-
2014
- 2014-06-15 IL IL233131A patent/IL233131A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014014558A8 (pt) | 2017-07-04 |
| NZ626990A (en) | 2016-01-29 |
| IL233131A0 (en) | 2014-07-31 |
| AU2012351342A1 (en) | 2014-07-24 |
| EP2790696A1 (en) | 2014-10-22 |
| SG11201402796SA (en) | 2014-06-27 |
| EA201491008A1 (ru) | 2015-02-27 |
| CA2859284A1 (en) | 2013-06-20 |
| US20140328861A1 (en) | 2014-11-06 |
| WO2013088109A1 (en) | 2013-06-20 |
| CN104114169A (zh) | 2014-10-22 |
| KR20140113667A (ko) | 2014-09-24 |
| MX2014007239A (es) | 2014-08-08 |
| EA026456B1 (ru) | 2017-04-28 |
| JP2015500326A (ja) | 2015-01-05 |
| BR112014014558A2 (pt) | 2017-06-13 |
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