WO2021045159A1 - 併用医薬による糖尿病の治療又は予防方法 - Google Patents

併用医薬による糖尿病の治療又は予防方法 Download PDF

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Publication number
WO2021045159A1
WO2021045159A1 PCT/JP2020/033463 JP2020033463W WO2021045159A1 WO 2021045159 A1 WO2021045159 A1 WO 2021045159A1 JP 2020033463 W JP2020033463 W JP 2020033463W WO 2021045159 A1 WO2021045159 A1 WO 2021045159A1
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Prior art keywords
alkyl
compound
formula
inhibitor
halo
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Ceased
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PCT/JP2020/033463
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English (en)
French (fr)
Japanese (ja)
Inventor
泰子 米良
壮平 勝見
千尋 大熊
誠也 持田
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Japan Tobacco Inc
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Japan Tobacco Inc
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Priority to JP2021544029A priority Critical patent/JP7692832B2/ja
Priority to US17/639,552 priority patent/US20230119894A1/en
Priority to CN202080076112.9A priority patent/CN114585387B/zh
Priority to CN202411355046.5A priority patent/CN119113123A/zh
Priority to EP20860175.7A priority patent/EP4026564A4/en
Priority to KR1020227010592A priority patent/KR20220056219A/ko
Priority to MX2022002683A priority patent/MX2022002683A/es
Priority to BR112022003323A priority patent/BR112022003323A2/pt
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Priority to AU2020341926A priority patent/AU2020341926B2/en
Priority to CA3151909A priority patent/CA3151909A1/en
Priority to EP23196223.4A priority patent/EP4342466A1/en
Publication of WO2021045159A1 publication Critical patent/WO2021045159A1/ja
Anticipated expiration legal-status Critical
Priority to JP2025050332A priority patent/JP2025094217A/ja
Ceased legal-status Critical Current

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    • 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
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • 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
    • A61K31/44—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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Definitions

  • Voglibose is a drug that has been approved for manufacture and sale of drugs, etc. based on the provisions of Article 14 of the Japanese Pharmaceutical Affairs Law (approval number: 21600AMZ00368, etc.).
  • Voglibose inhibits the disaccharide hydrolytic enzyme ( ⁇ -glucosidase), which is responsible for the decomposition of disaccharides present in the intestinal mucosa into monosaccharides, and inhibits or delays the digestion and absorption of carbohydrates in the intestinal tract, resulting in postprandial excess. Improves blood sugar. It is known that this pharmacological effect is effective in suppressing the onset of type 2 diabetes in impaired glucose tolerance. From these findings, it is considered that inhibiting the absorption of sugar from the small intestine by an SGLT1 inhibitor and improving postprandial hyperglycemia is effective in suppressing the onset of type 2 diabetes in impaired glucose tolerance.
  • an SGLT1 inhibitor and an SGLT2 inhibitor Compounds of formula [II] and dapagliflozin, Compounds of formula [II] and ipragliflozin, Compounds of formula [II] and tofogliflozin, Compounds of formula [II] and empagliflozin, The combination of a compound of formula [II] and canagliflozin and a compound of formula [II] and luseogliflozin is included.
  • therapeutically effective amounts of a DPP4 inhibitor are about 2.5 mg, about 5 mg, about 10 mg, about 12.5 g, about 25 mg, about 50 mg, about 75 mg, about 100 mg per day. It is about 125 mg, about 150 mg, about 175 mg or about 200 mg. In another embodiment, the therapeutically effective amount of the DPP4 inhibitor (eg, sitagliptin) is about 12.5 mg, about 25 mg, about 50 mg or about 100 mg per day.
  • each drug, medicine and pharmaceutical composition are used for humans and mammals other than humans (mouse, rat, hamster, guinea pig, rabbit, cat, dog, pig, cow, horse, sheep, monkey, etc.).
  • Oral or parenteral local, rectal, intravenous administration, intramuscular, subcutaneous, etc.
  • the dose varies depending on the administration target, disease, symptom, dosage form, administration route, etc., but for example, the dose when orally administered to an adult patient (body weight 60 kg) is determined for the active ingredient of each drug per day. It usually ranges from about 0.01 mg to about 1 g. These amounts can be administered in 1 to several divided doses.
  • a preferred solvent is a mixed solvent of tetrahydrofuran and water.
  • the acid include hydrochloric acid and trifluoroacetic acid.
  • the preferred acid is hydrochloric acid.
  • the reaction temperature is, for example, 20 ° C to 50 ° C, preferably room temperature.
  • the compound of the formula [13] can be obtained by subjecting the compound of the formula [11] and the compound of the formula [12] to a Curtius rearrangement reaction.
  • the compound of formula [13] can be obtained by reacting the compound of formula [11] with an azidating agent in the presence of a base and then reacting with the compound of formula [12].
  • the solvent include ether solvents such as tetrahydrofuran and 1,4-dioxane; and hydrocarbon solvents such as toluene.
  • the compound of the formula [12] may be used as a solvent.
  • a preferred solvent is toluene or a mixed solvent of toluene and the compound of formula [12].
  • -Carmonide solvents such as hexane and xylene; polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, and acetonitrile; and mixed solvents of these with water are exemplified.
  • Preferred solvents are 1,2-dimethoxyethane, toluene, dimethyl sulfoxide, or a mixed solvent of these with water.
  • the reaction temperature is, for example, 20 ° C to 150 ° C, preferably 80 ° C to 130 ° C.
  • Step 1 Production of 3- (2,5-dimethyl-1H-pyrrole-1-yl) -1H-pyrazole Acetic acid (1 L) was added to 1H-pyrazole-3-amine (100 g) at room temperature, and the mixture was stirred for 5 minutes. To this mixture was added 2,5-hexanedione (148 mL) at room temperature and stirred for 5 minutes. The reaction mixture was stirred at 120 ° C. for 2.5 hours and cooled to room temperature. Water (1 L) was added to this reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 50 minutes. The precipitated solid was collected by filtration and washed with water (1 L).
  • Step 2 1- (Bromodifluoromethyl) -3- (2,5-dimethyl-1H-pyrrole-1-yl) -1H-pyrazole and 1- (Bromodifluoromethyl) -5- (2,5-dimethyl)
  • DMF 100 mL
  • sodium hydride 14.9 g
  • a suspension of DMF 150 mL
  • Step 4 Production of ethyl 4- (3-fluoro-5-((1,1,1-trifluoro-2-methylpropan-2-yl) oxy) phenyl) -2,4-dioxobutanoate 1- (3-Fluoro-5-((1,1,1-trifluoro-2-methylpropan-2-yl) oxy) phenyl) ethane-1-one (4.09 g; 6) obtained in step 3 Diethyl oxalate (2.171 mL) was added to a solution of wt% n-hexane in THF (38.4 mL) under an argon atmosphere.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Biophysics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/JP2020/033463 2019-09-04 2020-09-03 併用医薬による糖尿病の治療又は予防方法 Ceased WO2021045159A1 (ja)

Priority Applications (12)

Application Number Priority Date Filing Date Title
MX2022002683A MX2022002683A (es) 2019-09-04 2020-09-03 Metodo terapeutico o profilactico para diabetes usando medicamentos combinados.
CN202080076112.9A CN114585387B (zh) 2019-09-04 2020-09-03 利用联用药物的糖尿病的治疗或预防方法
CN202411355046.5A CN119113123A (zh) 2019-09-04 2020-09-03 利用联用药物的糖尿病的治疗或预防方法
EP20860175.7A EP4026564A4 (en) 2019-09-04 2020-09-03 THERAPEUTIC OR PROPHYLACTIC PROCEDURE FOR DIABETES USING COMBINATION MEDICATION
KR1020227010592A KR20220056219A (ko) 2019-09-04 2020-09-03 병용 의약에 의한 당뇨병의 치료 또는 예방 방법
BR112022003323A BR112022003323A2 (pt) 2019-09-04 2020-09-03 Método terapêutico ou profilático para diabetes usando medicina de combinação
AU2020341926A AU2020341926B2 (en) 2019-09-04 2020-09-03 Therapeutic or prophylactic method for diabetes using combination medicine
JP2021544029A JP7692832B2 (ja) 2019-09-04 2020-09-03 併用医薬による糖尿病の治療又は予防方法
US17/639,552 US20230119894A1 (en) 2019-09-04 2020-09-03 Therapeutic or prophylactic method for diabetes using combination medicine
CA3151909A CA3151909A1 (en) 2019-09-04 2020-09-03 Therapeutic or prophylactic method for diabetes using combination medicine
EP23196223.4A EP4342466A1 (en) 2019-09-04 2020-09-03 Therapeutic or prophylactic method for diabetes using combination medicine
JP2025050332A JP2025094217A (ja) 2019-09-04 2025-03-25 併用医薬による糖尿病の治療又は予防方法

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JP2019-161526 2019-09-04
JP2019161526 2019-09-04

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US (1) US20230119894A1 (https=)
EP (2) EP4026564A4 (https=)
JP (2) JP7692832B2 (https=)
KR (1) KR20220056219A (https=)
CN (2) CN119113123A (https=)
AU (1) AU2020341926B2 (https=)
BR (1) BR112022003323A2 (https=)
CA (1) CA3151909A1 (https=)
MX (1) MX2022002683A (https=)
WO (1) WO2021045159A1 (https=)

Cited By (2)

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WO2023033483A1 (ko) * 2021-09-02 2023-03-09 주식회사 대웅테라퓨틱스 Sglt-2 억제제를 포함하는 당뇨병성 안질환 예방 또는 치료용 약학적 조성물
EP4026562A4 (en) * 2019-09-04 2023-09-13 Japan Tobacco Inc. METHOD FOR TREATING OR PREVENTING CHRONIC KIDNEY DISEASE

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CA3175131A1 (en) * 2020-03-19 2021-09-23 Chihiro Okuma Treatment or prevention method for chronic heart failure
WO2025245592A1 (en) * 2024-05-31 2025-12-04 Aché Laboratórios Farmacêuticos S.A. Multi-target compounds, process for the preparation of the compounds, intermediates, pharmaceutical composition, pharmaceutically acceptable salts, combination, medicament, use of a compound and method of treatment

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4026562A4 (en) * 2019-09-04 2023-09-13 Japan Tobacco Inc. METHOD FOR TREATING OR PREVENTING CHRONIC KIDNEY DISEASE
WO2023033483A1 (ko) * 2021-09-02 2023-03-09 주식회사 대웅테라퓨틱스 Sglt-2 억제제를 포함하는 당뇨병성 안질환 예방 또는 치료용 약학적 조성물

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