FI3914600T3 - Tiatsolopyridiinijohdannaisia adenosiinireseptoriantagonisteina - Google Patents
Tiatsolopyridiinijohdannaisia adenosiinireseptoriantagonisteina Download PDFInfo
- Publication number
- FI3914600T3 FI3914600T3 FIEP20700918.4T FI20700918T FI3914600T3 FI 3914600 T3 FI3914600 T3 FI 3914600T3 FI 20700918 T FI20700918 T FI 20700918T FI 3914600 T3 FI3914600 T3 FI 3914600T3
- Authority
- FI
- Finland
- Prior art keywords
- methoxy
- carboxylic acid
- decane
- azaspiro
- oxa
- Prior art date
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- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical class C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 title 1
- 229940121359 adenosine receptor antagonist Drugs 0.000 title 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title 1
- ZXUYWIRVAJJNSH-UHFFFAOYSA-N 8-oxa-2-azaspiro[4.5]decane-2-carboxylic acid Chemical compound C1N(C(=O)O)CCC21CCOCC2 ZXUYWIRVAJJNSH-UHFFFAOYSA-N 0.000 claims 40
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 9
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- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
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- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims 3
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- IXJFNUOEKYGUIV-UHFFFAOYSA-N 4-(2,5-dioxoimidazolidin-1-yl)piperidine-1-carboxylic acid Chemical compound OC(N(CC1)CCC1N(C(CN1)=O)C1=O)=O IXJFNUOEKYGUIV-UHFFFAOYSA-N 0.000 claims 2
- RKMRADDURCDMMT-UHFFFAOYSA-N 4-(2,5-dioxopyrrolidin-1-yl)piperidine-1-carboxylic acid Chemical compound OC(N(CC1)CCC1N(C(CC1)=O)C1=O)=O RKMRADDURCDMMT-UHFFFAOYSA-N 0.000 claims 2
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- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 2
- LZBRTCFJJHXCIN-UHFFFAOYSA-N OC(=O)N1CCC2(C1)CCCOC2 Chemical compound OC(=O)N1CCC2(C1)CCCOC2 LZBRTCFJJHXCIN-UHFFFAOYSA-N 0.000 claims 2
- 229930182555 Penicillin Natural products 0.000 claims 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims 2
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 2
- UJZUZMCKRDLSKD-RXMQYKEDSA-N (3r)-3-(aminomethyl)pyrrolidine-1-carboxylic acid Chemical compound NC[C@H]1CCN(C(O)=O)C1 UJZUZMCKRDLSKD-RXMQYKEDSA-N 0.000 claims 1
- SUUOTUHNULFDRE-SECBINFHSA-N (5R)-2,9-diazaspiro[4.5]decane-2-carboxylic acid Chemical compound OC(N(CC1)C[C@@]11CNCCC1)=O SUUOTUHNULFDRE-SECBINFHSA-N 0.000 claims 1
- SUUOTUHNULFDRE-VIFPVBQESA-N (5S)-2,9-diazaspiro[4.5]decane-2-carboxylic acid Chemical compound OC(N(CC1)C[C@]11CNCCC1)=O SUUOTUHNULFDRE-VIFPVBQESA-N 0.000 claims 1
- HPXJEMDSJYIVRG-UHFFFAOYSA-N 1-(imidazol-1-ylmethyl)cyclopropane-1-carboxylic acid Chemical compound C1=CN=CN1CC1(C(=O)O)CC1 HPXJEMDSJYIVRG-UHFFFAOYSA-N 0.000 claims 1
- QBNKIUAZIAPHKW-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decane-2-carboxylic acid Chemical compound C1N(C(=O)O)CCC21CCNCC2 QBNKIUAZIAPHKW-UHFFFAOYSA-N 0.000 claims 1
- SUUOTUHNULFDRE-UHFFFAOYSA-N 2,9-diazaspiro[4.5]decane-2-carboxylic acid Chemical compound C1N(C(=O)O)CCC21CNCCC2 SUUOTUHNULFDRE-UHFFFAOYSA-N 0.000 claims 1
- XTOUKVVXBPEOCG-UHFFFAOYSA-N 2-azaspiro[4.5]decane-2-carboxylic acid Chemical compound C1N(C(=O)O)CCC21CCCCC2 XTOUKVVXBPEOCG-UHFFFAOYSA-N 0.000 claims 1
- ZMEXBGJFJORKKS-UHFFFAOYSA-N 2-pyridin-3-yl-1h-imidazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CN=C1C1=CC=CN=C1 ZMEXBGJFJORKKS-UHFFFAOYSA-N 0.000 claims 1
- ACLXYWYMSZTOAU-UHFFFAOYSA-N 3-[(dimethylamino)methyl]bicyclo[1.1.1]pentane-1-carboxylic acid Chemical compound CN(C)CC(C1)(C2)CC12C(O)=O ACLXYWYMSZTOAU-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- VCEGDBURKQJDAX-UHFFFAOYSA-N 4-hydroxy-4-methylpiperidine-1-carboxylic acid Chemical compound CC1(O)CCN(C(O)=O)CC1 VCEGDBURKQJDAX-UHFFFAOYSA-N 0.000 claims 1
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- LZBRTCFJJHXCIN-SECBINFHSA-N C1N(CC[C@@]11COCCC1)C(=O)O Chemical compound C1N(CC[C@@]11COCCC1)C(=O)O LZBRTCFJJHXCIN-SECBINFHSA-N 0.000 claims 1
- LZBRTCFJJHXCIN-VIFPVBQESA-N C1N(CC[C@]11COCCC1)C(=O)O Chemical compound C1N(CC[C@]11COCCC1)C(=O)O LZBRTCFJJHXCIN-VIFPVBQESA-N 0.000 claims 1
- FKQOMSYWYGGXNP-MRVPVSSYSA-N C1OCC[C@]11CN(CC1)C(=O)O Chemical compound C1OCC[C@]11CN(CC1)C(=O)O FKQOMSYWYGGXNP-MRVPVSSYSA-N 0.000 claims 1
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- DOGXPDFZEQXZDS-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound C1=CC=CN2C(C(=O)O)=CN=C21 DOGXPDFZEQXZDS-UHFFFAOYSA-N 0.000 claims 1
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- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- 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
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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| CN119173276A (zh) | 2022-04-13 | 2024-12-20 | 吉利德科学公司 | 用于治疗表达Trop-2的癌症的组合疗法 |
| KR20250048043A (ko) | 2022-08-02 | 2025-04-07 | 메르크 파텐트 게엠베하 | (S)-7-옥사-2-아자-스피로[4.5]데칸-2-카르복실산 [7-(3,6-디히드로-2H-피란-4-일)-4-메톡시-티아졸로[4,5-c]피리딘-2-일]-아미드의 신규의 결정질 형태 및 이의 공-결정 형태 |
| CN116217511B (zh) * | 2023-03-22 | 2024-04-19 | 沈阳药科大学 | 一种双靶点化合物及其制备方法和在制备sEH抑制剂与PPARs激动剂中的应用 |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
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| US4125828A (en) | 1972-08-04 | 1978-11-14 | Med-El Inc. | Method and apparatus for automated classification and analysis of cells |
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| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
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| US6734179B2 (en) * | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| EP1465634B1 (en) | 2001-12-12 | 2014-10-22 | The Government of the United States of America, as represented by the Secretary Department of Health and Human Services | Methods for using adenosine receptor inhibitors to enhance immune response and inflammation |
| EP1618108A2 (en) | 2003-04-09 | 2006-01-25 | Biogen Idec MA Inc. | Triazolo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines useful as a2a adenosine receptor antagonists |
| JP4444290B2 (ja) | 2003-05-19 | 2010-03-31 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシン受容体リガンドとしてのベンゾチアゾール誘導体 |
| BRPI0414266A (pt) * | 2003-09-19 | 2006-11-07 | Hoffmann La Roche | derivados de tiazolopiridina como ligandos receptores da adenosina |
| US7054288B2 (en) * | 2004-02-13 | 2006-05-30 | Interdigital Technology Corporation | Method and apparatus for providing fast detection of a high speed shared control channel |
| DE102004008908A1 (de) * | 2004-02-24 | 2005-09-08 | Patent-Treuhand-Gesellschaft für elektrische Glühlampen mbH | Ansteuerschaltung für Wandler |
| FR2867354A1 (fr) * | 2004-03-09 | 2005-09-16 | Joseph Vaillant | Ferrure mecanique pour sabot, notamment pour cheval de sport |
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| US11220492B2 (en) * | 2017-05-17 | 2022-01-11 | Arcus Biosciences, Inc. | Quinazoline-pyrazole derivatives for the treatment of cancer-related disorders |
| RS64035B1 (sr) * | 2017-08-01 | 2023-04-28 | Merck Patent Gmbh | Derivati tiazolopiridina kao antagonisti receptora adenozina |
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| US20220119412A1 (en) | 2022-04-21 |
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| CN113939520B (zh) | 2024-11-22 |
| AU2020211697A1 (en) | 2021-09-09 |
| KR102891741B1 (ko) | 2025-11-26 |
| WO2020152132A1 (en) | 2020-07-30 |
| HUE068968T2 (hu) | 2025-02-28 |
| EP3914600B1 (en) | 2024-08-07 |
| PL3914600T3 (pl) | 2024-12-23 |
| EP3914600A1 (en) | 2021-12-01 |
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| US12344623B2 (en) | 2025-07-01 |
| AU2020211697B2 (en) | 2025-08-14 |
| PT3914600T (pt) | 2024-10-04 |
| BR112021014406A2 (pt) | 2021-12-07 |
| AR117844A1 (es) | 2021-09-01 |
| HRP20241385T1 (hr) | 2024-12-20 |
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