KR20190015492A - 화학적 화합물 - Google Patents
화학적 화합물 Download PDFInfo
- Publication number
- KR20190015492A KR20190015492A KR1020197000188A KR20197000188A KR20190015492A KR 20190015492 A KR20190015492 A KR 20190015492A KR 1020197000188 A KR1020197000188 A KR 1020197000188A KR 20197000188 A KR20197000188 A KR 20197000188A KR 20190015492 A KR20190015492 A KR 20190015492A
- Authority
- KR
- South Korea
- Prior art keywords
- chlorophenoxy
- acetamide
- methyl
- pyrrolidin
- cancer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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- YABQYIDNNXZBLP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 YABQYIDNNXZBLP-UHFFFAOYSA-N 0.000 claims description 4
- AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 claims description 4
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- QXBCJEACQNYBPS-UHFFFAOYSA-N N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]-2-(3,4-dichlorophenoxy)acetamide Chemical compound ClC1=CC=C(OCCCN2CC(CC2)CNC(COC2=CC(=C(C=C2)Cl)Cl)=O)C=C1 QXBCJEACQNYBPS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- WECGRPLVFNVBOS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 WECGRPLVFNVBOS-UHFFFAOYSA-N 0.000 claims description 3
- IQFZJDLJRNUJHE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCOC2=CC=C(C=C2)Cl)C=C1 IQFZJDLJRNUJHE-UHFFFAOYSA-N 0.000 claims description 3
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- GGJCZSUQNJRNNU-UHFFFAOYSA-N ethyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OCC GGJCZSUQNJRNNU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- DTOOBYVMEKEJOW-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=CC(=C1)F DTOOBYVMEKEJOW-UHFFFAOYSA-N 0.000 claims description 2
- PVXZAVFISRNWJY-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound Fc1cc(OCC(=O)NCC2CCN(C2)C(=O)COc2ccc(Cl)cc2)ccc1Cl PVXZAVFISRNWJY-UHFFFAOYSA-N 0.000 claims description 2
- YYYSGWZVPDPIQL-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1)F YYYSGWZVPDPIQL-UHFFFAOYSA-N 0.000 claims description 2
- BUYDDANXXSXDKU-UHFFFAOYSA-N 2-(4-chloro-3-methylphenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1)C BUYDDANXXSXDKU-UHFFFAOYSA-N 0.000 claims description 2
- FLXOOBPIISWSLO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[2-[2-(4-chlorophenoxy)acetyl]-2,7-diazaspiro[4.4]nonan-7-yl]ethanone Chemical compound C1N(CCC11CN(CC1)C(COC1=CC=C(C=C1)Cl)=O)C(COC1=CC=C(C=C1)Cl)=O FLXOOBPIISWSLO-UHFFFAOYSA-N 0.000 claims description 2
- MYNDWAZXXRDFHT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[5-[2-(4-chlorophenoxy)acetyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]ethanone Chemical compound Clc1ccc(OCC(=O)N2CC3CN(CC3C2)C(=O)COc2ccc(Cl)cc2)cc1 MYNDWAZXXRDFHT-UHFFFAOYSA-N 0.000 claims description 2
- DDLOSEMFQHOHSQ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(C2)C(=O)COc2ccc(Cl)cc2)cc1 DDLOSEMFQHOHSQ-UHFFFAOYSA-N 0.000 claims description 2
- FDXMRZKBWRLGNS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]ethyl]acetamide Chemical compound Clc1ccc(OCC(=O)NCCC2CCN(C2)C(=O)COc2ccc(Cl)cc2)cc1 FDXMRZKBWRLGNS-UHFFFAOYSA-N 0.000 claims description 2
- NJOTXDBUDMUVMT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[2-(4-chlorophenoxy)acetyl]-2-azaspiro[4.5]decan-8-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCC3(CCN(C3)C(=O)COc3ccc(Cl)cc3)CC2)cc1 NJOTXDBUDMUVMT-UHFFFAOYSA-N 0.000 claims description 2
- UAUXVMNQQOCUFA-QRWMCTBCSA-N 2-(4-chlorophenoxy)-N-[[(3R)-1-[3-(4-chlorophenoxy)propyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@@H]2CN(C(C2)C)CCCOC2=CC=C(C=C2)Cl)C=C1 UAUXVMNQQOCUFA-QRWMCTBCSA-N 0.000 claims description 2
- IKOSSBXOSHFJDL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)F)C=C1 IKOSSBXOSHFJDL-UHFFFAOYSA-N 0.000 claims description 2
- HFAOETXPQBJFEJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-3-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound CC1(CNC(=O)COc2ccc(Cl)cc2)CCN(C1)C(=O)COc1ccc(Cl)cc1 HFAOETXPQBJFEJ-UHFFFAOYSA-N 0.000 claims description 2
- TVDBVWWGFKIMKH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(C(C2)C)C(COC2=CC=C(C=C2)Cl)=O)C=C1 TVDBVWWGFKIMKH-UHFFFAOYSA-N 0.000 claims description 2
- KJWVSICNWIGTDS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCOC2=CC=C(C=C2)Cl)F)C=C1 KJWVSICNWIGTDS-UHFFFAOYSA-N 0.000 claims description 2
- KNBFPVWLBFDPKT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(C(C2)C)CCOC2=CC=C(C=C2)Cl)C=C1 KNBFPVWLBFDPKT-UHFFFAOYSA-N 0.000 claims description 2
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- BISDYPUAIKBWDZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-2-oxopyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2C(N(CC2)CCCOC2=CC=C(C=C2)Cl)=O)C=C1 BISDYPUAIKBWDZ-UHFFFAOYSA-N 0.000 claims description 2
- NUUQDTIUVLINLY-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCCOC2=CC=C(C=C2)Cl)F)C=C1 NUUQDTIUVLINLY-UHFFFAOYSA-N 0.000 claims description 2
- VDBIMXSTBYWFCL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-3-hydroxypyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCCOC2=CC=C(C=C2)Cl)O)C=C1 VDBIMXSTBYWFCL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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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
- A61K31/40—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
- A61K31/4025—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 not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| BR112020011914A2 (pt) | 2017-12-13 | 2020-11-24 | Praxis Biotech LLC | inibidores de via de resposta de tensão integrada |
| KR102803660B1 (ko) | 2018-03-05 | 2025-05-02 | 브리스톨-마이어스 스큅 컴퍼니 | 페닐피롤리디논 포르밀 펩티드 2 수용체 효능제 |
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| US11253522B2 (en) | 2018-04-28 | 2022-02-22 | The Regents Of The University Of California | Cancer treatment targeted to tumor adaptive responses to protein synthesis stress |
| JP2021527044A (ja) | 2018-06-05 | 2021-10-11 | プラクシス バイオテック エルエルシー | 統合的ストレス応答経路の阻害剤 |
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| CN117062817A (zh) * | 2021-01-13 | 2023-11-14 | 斯瑞福治疗股份有限公司 | 用于抑制sgk-1的吡唑并[3,4-d]嘧啶-6-基-磺酰胺衍生物 |
| CN116332818B (zh) * | 2021-12-22 | 2023-12-15 | 王喆明 | 四氢吡咯衍生物及其应用 |
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| US20080283653A1 (en) * | 2007-04-20 | 2008-11-20 | Invista North America Sarl | Compact continuous over end take-off (oeto) creel with tension control |
| WO2008150231A1 (en) * | 2007-06-08 | 2008-12-11 | Astrazeneca Ab | New heterocyclic compounds for treatment of respiratory, airway or inflammatory disorders |
| EP2535354B1 (en) | 2007-06-18 | 2017-01-11 | Merck Sharp & Dohme B.V. | Antibodies to human programmed death receptor pd-1 |
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| WO2014055897A2 (en) | 2012-10-04 | 2014-04-10 | Dana-Farber Cancer Institute, Inc. | Human monoclonal anti-pd-l1 antibodies and methods of use |
| JP5799117B2 (ja) * | 2013-02-05 | 2015-10-21 | 大日本住友製薬株式会社 | ウラシル誘導体からなる医薬 |
| WO2014144952A2 (en) | 2013-03-15 | 2014-09-18 | Peter Walter | Modulators of the eif2alpha pathway |
| WO2015038778A1 (en) * | 2013-09-11 | 2015-03-19 | The Brigham And Women's Hospital, Inc. | SUBSTITUTED UREA EIF2α KINASE ACTIVATORS |
| US9676757B2 (en) | 2014-02-27 | 2017-06-13 | Merck Patent Gmbh | Heterocyclic compounds as NaV channel inhibitors and uses thereof |
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| BR112018075615A2 (pt) | 2019-07-02 |
| CA3026983A1 (en) | 2017-12-14 |
| AU2017279027A1 (en) | 2018-12-20 |
| WO2017212423A1 (en) | 2017-12-14 |
| JP2019521109A (ja) | 2019-07-25 |
| US10851053B2 (en) | 2020-12-01 |
| RU2018146946A (ru) | 2020-07-10 |
| EP3468948A1 (en) | 2019-04-17 |
| US20190144384A1 (en) | 2019-05-16 |
| CN109563034A (zh) | 2019-04-02 |
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