WO2008156656A3 - Method for making biaryl compounds, compounds made by the method, and method for their use - Google Patents

Method for making biaryl compounds, compounds made by the method, and method for their use Download PDF

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Publication number
WO2008156656A3
WO2008156656A3 PCT/US2008/007378 US2008007378W WO2008156656A3 WO 2008156656 A3 WO2008156656 A3 WO 2008156656A3 US 2008007378 W US2008007378 W US 2008007378W WO 2008156656 A3 WO2008156656 A3 WO 2008156656A3
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WO
WIPO (PCT)
Prior art keywords
compounds
making
diels
biaryl
certain
Prior art date
Application number
PCT/US2008/007378
Other languages
French (fr)
Other versions
WO2008156656A2 (en
Inventor
Rich Garrett Carter
Bradley O Ashburn
Michael R Naffziger
Johanna P Schwartz
Original Assignee
Oregon State
Rich Garrett Carter
Bradley O Ashburn
Michael R Naffziger
Johanna P Schwartz
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Oregon State, Rich Garrett Carter, Bradley O Ashburn, Michael R Naffziger, Johanna P Schwartz filed Critical Oregon State
Publication of WO2008156656A2 publication Critical patent/WO2008156656A2/en
Publication of WO2008156656A3 publication Critical patent/WO2008156656A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4015—Esters of acyclic unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/532—Cycloaliphatic phosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.
PCT/US2008/007378 2007-06-13 2008-06-13 Method for making biaryl compounds, compounds made by the method, and method for their use WO2008156656A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US93458807P 2007-06-13 2007-06-13
US60/934,588 2007-06-13
US2882008P 2008-02-14 2008-02-14
US61/028,820 2008-02-14

Publications (2)

Publication Number Publication Date
WO2008156656A2 WO2008156656A2 (en) 2008-12-24
WO2008156656A3 true WO2008156656A3 (en) 2009-02-19

Family

ID=40156843

Family Applications (1)

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PCT/US2008/007378 WO2008156656A2 (en) 2007-06-13 2008-06-13 Method for making biaryl compounds, compounds made by the method, and method for their use

Country Status (1)

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WO (1) WO2008156656A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8314250B2 (en) 2009-11-24 2012-11-20 Hoffmann-La Roche Inc. Sultam derivatives
CN102382038B (en) * 2011-09-22 2013-05-08 浙江大学 Preparation method for synthesizing carbazoles alkaloid Siamenol
TWI425076B (en) * 2011-11-01 2014-02-01 Ind Tech Res Inst Carbazole derivatives and organic light-emitting diodes comprising the same
CN104447358B (en) * 2014-10-28 2016-04-13 常州大学 A kind of synthesis N, N ', N ", N " '-four (3-bromophenyl)-p-diaminodiphenyl methods
CR20200347A (en) 2018-02-13 2020-09-23 Gilead Sciences Inc Pd-1/pd-l1 inhibitors
CN112041311B (en) 2018-04-19 2023-10-03 吉利德科学公司 PD-1/PD-L1 inhibitors
KR20230159715A (en) 2018-07-13 2023-11-21 길리애드 사이언시즈, 인코포레이티드 Pd-1/pd-l1 inhibitors
AU2019366355B2 (en) 2018-10-24 2022-10-13 Gilead Sciences, Inc. PD-1/PD-L1 inhibitors
JP7493384B2 (en) 2020-05-27 2024-05-31 東ソー・ファインケム株式会社 Method for producing 2,3,4,5,6-pentafluorostyrene
CN111747823B (en) * 2020-07-22 2021-04-20 华东理工大学 Polysubstituted chlorine ethynylbenzene compound and preparation method and application thereof
WO2023044364A1 (en) 2021-09-15 2023-03-23 Enko Chem, Inc. Protoporphyrinogen oxidase inhibitors

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312820A (en) * 1992-07-17 1994-05-17 Merck & Co., Inc. Substituted carbamoyl and oxycarbonyl derivatives of biphenylmethylamines
US5627256A (en) * 1994-12-21 1997-05-06 Bayer Ag Polycarbonates containing aryl phosphines
US5686474A (en) * 1992-08-11 1997-11-11 Basf Aktiengesellschaft Acetylene derivatives and crop protection agents containing them
US20020156077A1 (en) * 2001-02-22 2002-10-24 Schmidt Jonathan Martin Non-steroidal estrogen receptor ligands
US20050256181A1 (en) * 2004-01-29 2005-11-17 Elixir Pharmaceuticals, Inc. Treating a viral disorder

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312820A (en) * 1992-07-17 1994-05-17 Merck & Co., Inc. Substituted carbamoyl and oxycarbonyl derivatives of biphenylmethylamines
US5686474A (en) * 1992-08-11 1997-11-11 Basf Aktiengesellschaft Acetylene derivatives and crop protection agents containing them
US5627256A (en) * 1994-12-21 1997-05-06 Bayer Ag Polycarbonates containing aryl phosphines
US20020156077A1 (en) * 2001-02-22 2002-10-24 Schmidt Jonathan Martin Non-steroidal estrogen receptor ligands
US20050256181A1 (en) * 2004-01-29 2005-11-17 Elixir Pharmaceuticals, Inc. Treating a viral disorder

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