CN109563055A - 氨基吡嗪类化合物或盐、异构体、其制备方法及用途 - Google Patents
氨基吡嗪类化合物或盐、异构体、其制备方法及用途 Download PDFInfo
- Publication number
- CN109563055A CN109563055A CN201780041770.2A CN201780041770A CN109563055A CN 109563055 A CN109563055 A CN 109563055A CN 201780041770 A CN201780041770 A CN 201780041770A CN 109563055 A CN109563055 A CN 109563055A
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- Prior art keywords
- ethyoxyl
- base
- amido
- compound
- alkyl
- Prior art date
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- Granted
Links
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- 150000003839 salts Chemical class 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title description 230
- 230000000694 effects Effects 0.000 claims abstract description 15
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims abstract description 11
- 239000002269 analeptic agent Substances 0.000 claims abstract description 8
- 239000002585 base Substances 0.000 claims description 337
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 278
- 150000001875 compounds Chemical class 0.000 claims description 253
- PTZIVVDMBCVSMR-UHFFFAOYSA-N 2,3-diphenylpyrazine Chemical compound C1=CC=CC=C1C1=NC=CN=C1C1=CC=CC=C1 PTZIVVDMBCVSMR-UHFFFAOYSA-N 0.000 claims description 229
- 239000000243 solution Substances 0.000 claims description 124
- 238000006243 chemical reaction Methods 0.000 claims description 123
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 97
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- 125000005843 halogen group Chemical group 0.000 claims description 62
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- 125000003368 amide group Chemical group 0.000 claims description 45
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
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- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 7
- 238000005576 amination reaction Methods 0.000 claims description 7
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
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- 125000003375 sulfoxide group Chemical group 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- HORKLFSLSQJYEO-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)pyrazine Chemical compound C1=CC(F)=CC=C1C1=NC=CN=C1C1=CC=C(F)C=C1 HORKLFSLSQJYEO-UHFFFAOYSA-N 0.000 claims description 3
- BCMQEWWLHAXCJY-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)pyrazine Chemical compound C1=CC(OC)=CC=C1C1=NC=CN=C1C1=CC=C(OC)C=C1 BCMQEWWLHAXCJY-UHFFFAOYSA-N 0.000 claims description 3
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- XKSJFAVKODCELZ-UHFFFAOYSA-N 5-methyl-2,3-diphenylpyrazine Chemical compound C=1C=CC=CC=1C1=NC(C)=CN=C1C1=CC=CC=C1 XKSJFAVKODCELZ-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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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
- A61K31/395—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
- A61K31/4965—Non-condensed pyrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D241/20—Nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
一种如通式(I)示出的氨基吡嗪类化合物或其药学上可接受的盐、异构体被公开，其具有前列腺素I2(PGI2)受体激动活性，用作IP受体激动剂以治疗相关疾病。
Description
PCT国内申请，说明书已公开。
Claims (17)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2016106067983 | 2016-07-29 | ||
| CN201610606798 | 2016-07-29 | ||
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| CN108863955B (zh) * | 2018-08-03 | 2021-08-13 | 成都苑东生物制药股份有限公司 | 二苯基吡嗪类化合物或其药学上可接受的盐、异构体及其制备方法和用途 |
| CN108774183A (zh) * | 2018-08-03 | 2018-11-09 | 成都苑东生物制药股份有限公司 | 一种乙二醇类化合物的制备方法 |
| CN108623541A (zh) * | 2018-08-03 | 2018-10-09 | 成都苑东生物制药股份有限公司 | 一种二苯吡嗪化合物的制备方法 |
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