CN114391010A - 一种三环吡唑衍生物及其制备 - Google Patents
一种三环吡唑衍生物及其制备 Download PDFInfo
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- CN114391010A CN114391010A CN202080061776.8A CN202080061776A CN114391010A CN 114391010 A CN114391010 A CN 114391010A CN 202080061776 A CN202080061776 A CN 202080061776A CN 114391010 A CN114391010 A CN 114391010A
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- alkyl
- ring
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- pain
- radical
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 46
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 210000000963 osteoblast Anatomy 0.000 description 1
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- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000008533 pain sensitivity Effects 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- OWTCGJRBQMOICX-UHFFFAOYSA-M phenacyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(=O)C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OWTCGJRBQMOICX-UHFFFAOYSA-M 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
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- 238000005070 sampling Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000011664 signaling Effects 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- VRQDPNKOUPEWOC-UHFFFAOYSA-N spiro[bicyclo[2.2.2]octane-3,3'-piperidine] Chemical compound C1CCNCC21C(CC1)CCC1C2 VRQDPNKOUPEWOC-UHFFFAOYSA-N 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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Classifications
-
- 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
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明公开一种式(I)所示的三环吡唑化合物及其立体异构体、药学上可接受的盐、溶剂化物、水合物、N‑氧化物、前药及其药物组合物、制备方法，以及在由大麻素CB2受体介导的疾病的预防和治疗中的用途。
Description
PCT国内申请，说明书已公开。
Claims (23)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2019108658290 | 2019-09-12 | ||
| CN201910865829 | 2019-09-12 | ||
| CN201910970499 | 2019-10-14 | ||
| CN2019109704991 | 2019-10-14 | ||
| CN201911075561 | 2019-11-06 | ||
| CN2019110755617 | 2019-11-06 | ||
| CN201911265153 | 2019-12-11 | ||
| CN2019112651538 | 2019-12-11 | ||
| CN202010013101 | 2020-01-07 | ||
| CN2020100131018 | 2020-01-07 | ||
| CN202010227395 | 2020-03-27 | ||
| CN2020102273954 | 2020-03-27 | ||
| PCT/CN2020/114451 WO2021047583A1 (zh) | 2019-09-12 | 2020-09-10 | 一种三环吡唑衍生物及其制备 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114391010A true CN114391010A (zh) | 2022-04-22 |
Family
ID=74866064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080061776.8A Pending CN114391010A (zh) | 2019-09-12 | 2020-09-10 | 一种三环吡唑衍生物及其制备 |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN114391010A (zh) |
| TW (1) | TWI768464B (zh) |
| WO (1) | WO2021047583A1 (zh) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005095353A1 (en) * | 2004-03-24 | 2005-10-13 | Janssen Pharmaceutica, N.V. | Tetrahydro-indazole cannabinoid modulators |
| WO2006030124A1 (fr) * | 2004-09-13 | 2006-03-23 | Sanofi-Aventis | Derives de pyrazole condense, leur preparation et leur application en therapeutique. |
| WO2006129178A1 (en) * | 2005-06-02 | 2006-12-07 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| WO2008093194A1 (en) * | 2007-01-29 | 2008-08-07 | Glenmark Pharmaceuticals, S.A. | Cannabinoid receptor modulators for treating non-immediate type allergic diseases |
| US20110028451A1 (en) * | 2009-07-31 | 2011-02-03 | N.V. Organon | Dihydrobenzoindazoles |
| WO2011025541A1 (en) * | 2009-08-28 | 2011-03-03 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116278A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116277A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116279A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2017039643A1 (en) * | 2015-09-01 | 2017-03-09 | Arena Pharmaceuticals, Inc. | Cb2 receptor internalization |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1393930B1 (it) * | 2009-02-25 | 2012-05-17 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
-
2020
- 2020-09-10 CN CN202080061776.8A patent/CN114391010A/zh active Pending
- 2020-09-10 TW TW109131056A patent/TWI768464B/zh not_active IP Right Cessation
- 2020-09-10 WO PCT/CN2020/114451 patent/WO2021047583A1/zh active Application Filing
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005095353A1 (en) * | 2004-03-24 | 2005-10-13 | Janssen Pharmaceutica, N.V. | Tetrahydro-indazole cannabinoid modulators |
| WO2006030124A1 (fr) * | 2004-09-13 | 2006-03-23 | Sanofi-Aventis | Derives de pyrazole condense, leur preparation et leur application en therapeutique. |
| WO2006129178A1 (en) * | 2005-06-02 | 2006-12-07 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| WO2008093194A1 (en) * | 2007-01-29 | 2008-08-07 | Glenmark Pharmaceuticals, S.A. | Cannabinoid receptor modulators for treating non-immediate type allergic diseases |
| US20110028451A1 (en) * | 2009-07-31 | 2011-02-03 | N.V. Organon | Dihydrobenzoindazoles |
| WO2011025541A1 (en) * | 2009-08-28 | 2011-03-03 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116278A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116277A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116279A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2017039643A1 (en) * | 2015-09-01 | 2017-03-09 | Arena Pharmaceuticals, Inc. | Cb2 receptor internalization |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI768464B (zh) | 2022-06-21 |
| TW202115030A (zh) | 2021-04-16 |
| WO2021047583A1 (zh) | 2021-03-18 |
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