JP2009057388A5 - - Google Patents
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- JP2009057388A5 JP2009057388A5 JP2008262208A JP2008262208A JP2009057388A5 JP 2009057388 A5 JP2009057388 A5 JP 2009057388A5 JP 2008262208 A JP2008262208 A JP 2008262208A JP 2008262208 A JP2008262208 A JP 2008262208A JP 2009057388 A5 JP2009057388 A5 JP 2009057388A5
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- pyrimidine
- purine
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- palladium catalyst
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052763 palladium Inorganic materials 0.000 claims 14
- 150000001413 amino acids Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 10
- 239000007858 starting material Substances 0.000 claims 9
- 239000012038 nucleophile Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- 150000001298 alcohols Chemical class 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 230000004048 modification Effects 0.000 claims 4
- 238000006011 modification reaction Methods 0.000 claims 4
- 239000002718 pyrimidine nucleoside Substances 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 150000003573 thiols Chemical class 0.000 claims 4
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Natural products NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 3
- 229960000643 Adenine Drugs 0.000 claims 3
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims 3
- UHDGCWIWMRVCDJ-XVFCMESISA-N Cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-XVFCMESISA-N 0.000 claims 3
- ASJSAQIRZKANQN-CRCLSJGQSA-N Deoxyribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims 3
- UYTPUPDQBNUYGX-UHFFFAOYSA-N Guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 3
- CMUOJBJRZUHRMU-UHFFFAOYSA-N Nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims 3
- 229920000272 Oligonucleotide Polymers 0.000 claims 3
- DRTQHJPVMGBUCF-UCVXFZOQSA-N Uridine Natural products O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 claims 3
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims 3
- 229940045145 Uridine Drugs 0.000 claims 3
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001913 cyanates Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 150000002170 ethers Chemical class 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 239000002212 purine nucleoside Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- 241000701022 Cytomegalovirus Species 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N Hexamethylphosphoramide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- MRWXACSTFXYYMV-FDDDBJFASA-N NEBULARINE Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims 2
- 206010047461 Viral infection Diseases 0.000 claims 2
- 208000001756 Virus Disease Diseases 0.000 claims 2
- 230000027455 binding Effects 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000017613 viral reproduction Effects 0.000 claims 2
- UAGYHIZGHDGMCY-FNCVBFRFSA-N (2R,3S,4R,5R)-2-(hydroxymethyl)-5-pyrimidin-1-ium-1-yloxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CN=C1 UAGYHIZGHDGMCY-FNCVBFRFSA-N 0.000 claims 1
- RKSLVDIXBGWPIS-UAKXSSHOSA-N 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 RKSLVDIXBGWPIS-UAKXSSHOSA-N 0.000 claims 1
- LQQGJDJXUSAEMZ-UAKXSSHOSA-N 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one Chemical compound C1=C(I)C(N)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 LQQGJDJXUSAEMZ-UAKXSSHOSA-N 0.000 claims 1
- -1 5'-protected 5-iodo-uridine Chemical class 0.000 claims 1
- YUMLVGUENDTDLP-UHFFFAOYSA-N 8-Iodo-Guanine Chemical compound O=C1NC(N)=NC2=NC(I)=N[C]21 YUMLVGUENDTDLP-UHFFFAOYSA-N 0.000 claims 1
- XUMSFQKCBNKNCE-UHFFFAOYSA-N 8-iodo-7H-purin-6-amine Chemical compound NC1=NC=NC2=C1NC(I)=N2 XUMSFQKCBNKNCE-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229920003013 deoxyribonucleic acid Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- WVGZZTIINNFUQS-UHFFFAOYSA-N pentamethylphosphoranuidylmethane Chemical compound C[P-](C)(C)(C)(C)C WVGZZTIINNFUQS-UHFFFAOYSA-N 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 150000003834 purine nucleoside derivatives Chemical class 0.000 claims 1
- 229920002477 rna polymer Polymers 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 230000003612 virological Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 C*1OC(C(*(C=C(C(C)=O)C(*2)=O)C2=*)O)C(*CO)O1 Chemical compound C*1OC(C(*(C=C(C(C)=O)C(*2)=O)C2=*)O)C(*CO)O1 0.000 description 9
- DDIYNLIVSJFJLB-XQRVVYSFSA-N CCC/C(/N)=C/C Chemical compound CCC/C(/N)=C/C DDIYNLIVSJFJLB-XQRVVYSFSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Claims (53)
ｉ）パラジウム触媒の溶液を準備し、ここにおいて、前記パラジウム触媒は、Ｐｄ（０）Ｌ ３ またはＰｄ（０）Ｌ ４ ［式中、Ｌはパラジウムのリガンドである］からなるグループから選択される；
ｉｉ）プリン出発原料の２−，６−または８−位置に結合したハロゲン離脱基を含有するプリン出発原料を、パラジウム触媒及び塩基の存在下に求核試薬および一酸化炭素と反応させ；そして
ｉｉｉ）上記修飾プリンヌクレオシドを単離し、そして精製する
工程を含む、前記方法。 In a process for producing a purine nucleoside modified at the 2-, 6- or 8-position of the purine ring ,
i) preparing a solution of a palladium catalyst, wherein the palladium catalyst is selected from the group consisting of Pd (0) L 3 or Pd (0) L 4 , wherein L is a ligand of palladium. ;
ii) reacting a purine starting material containing a halogen leaving group bonded to the 2-, 6- or 8-position of the purine starting material with a nucleophile and carbon monoxide in the presence of a palladium catalyst and a base ; and iii. ) Isolate and purify the modified purine nucleoside
Said method comprising the steps .
（式中，Ｙは０，ＮＨおよびＮＲ’からなる群より選択され、
ＲおよびＲ’は独立にＣ１〜Ｃ２０アルキル、Ｃ２〜Ｃ２０アルケニル、Ｃ ６ 〜Ｃ ２０ アリール、およびアミノ酸からなる群より選択され、この場合、ＲおよびＲ’は所望により環構造の一部であってもよい）
を有する、「請求項９」記載の方法。 The nucleophile has the formula: RYH
Wherein Y is selected from the group consisting of 0, NH and NR ′;
R and R ′ are independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkenyl , C 6 -C 20 aryl, and amino acids, where R and R ′ are optionally of ring structure (May be part)
The method of claim 9 , comprising:
Ｒは、（ＣＨｚ）ｍ（ＣＨ３）ｎ（式中、ｚは０，１または２であり、ｍは０〜１９であり、ｎは０，１，２または３である）であり、この場合１個または２個以上のＨは所望により、＝Ｏ，−ＯＨ，＝ＮＨ，ＮＨ２，Ｎ＋Ｍｅ３Ｃｌ−，
「請求項１０」記載の方法。 Y is selected from the group consisting of O and NH ;
R is (CH z ) m (CH 3 ) n , wherein z is 0, 1 or 2, m is 0 to 19, and n is 0, 1, 2 or 3. this case one or more H are desired, = O, -OH, = NH , NH 2, N + Me 3 Cl -,
The method according to claim 10 .
［式中、Ｌは，Ｐ（Ｃ６Ｈ５）３，（ｏ−ｔｏ１）３Ｐ，ＣＨ３ＣＮ，ＤＭＳＯ，Ｎ，Ｎ−ジメチルホルムアミド（ＤＭＦ），
である、「請求項１」記載の方法。 The palladium catalyst has the formula: Pd (0) L 3 or Pd (0) L 4
[In the formula, L represents P (C 6 H 5 ) 3 , (o-to1) 3 P, CH 3 CN, DMSO, N, N-dimethylformamide (DMF),
The method according to claim 1, wherein
ｉ）パラジウム触媒の溶液を準備し、ここにおいて、前記パラジウム触媒は、Ｐｄ（０）Ｌ ４ ［式中、Ｌはパラジウムのリガンドである］からなるグループから選択される；
ｉｉ）ピリミジン出発原料の５−または６−位置に結合したハロゲン離脱基を含有するピリミジン出発原料を、パラジウム触媒及び塩基の存在下に求核試薬および一酸化炭素と反応させ；そして
ｉｉｉ）上記修飾ピリミジンヌクレオシドを単離し、そして精製する
工程を含む、前記方法。 In a process for the preparation of pyrimidine nucleosides modified at the 5- or 6-position of the pyrimidine ring ,
i) providing a solution of a palladium catalyst, wherein the palladium catalyst is selected from the group consisting of Pd (0) L 4 , wherein L is a ligand of palladium;
ii) reacting a pyrimidine starting material containing a halogen leaving group attached to the 5- or 6-position of the pyrimidine starting material with a nucleophile and carbon monoxide in the presence of a palladium catalyst and a base ; and iii) the above modification Isolate and purify pyrimidine nucleosides
Said method comprising the steps .
（式中，Ｙは０，Ｓ，ＮＨまたはＮＲ’からなる群より選択され、
ＲおよびＲ’は独立にＣ１〜Ｃ２０アルキル（直鎖状または分岐状）、Ｃ２〜Ｃ２０アルケニル（直鎖状または分岐状）、Ｃ６〜Ｃ２０アリールおよびアミノ酸からなる群より選択され、この場合、ＲおよびＲ’は所望により芳香族、脂肪族または異項環の環構造の一部であってもよい）を有する、
「請求項２７」記載の方法。 The nucleophile has the formula: RYH
Wherein Y is selected from the group consisting of 0, S, NH or NR ′;
R and R ′ are independently selected from the group consisting of C 1 -C 20 alkyl (linear or branched), C 2 -C 20 alkenyl (linear or branched), C 6 -C 20 aryl and amino acids. Wherein R and R ′ may optionally be part of an aromatic, aliphatic or heterocyclic ring structure),
The method according to claim 27 .
Ｒは、（ＣＨｚ）ｍ（ＣＨ３）ｎ（式中、ｚは０，１または２であり、ｍは０〜１９であり、ｎは０，１，２または３である）であり、この場合１個または２個以上のＨは所望により＝Ｏ，−ＯＨ，＝ＮＨ，ＮＨ２，Ｎ＋Ｍｅ３Ｃｌ−，
「請求項２８」記載の方法。 Y is selected from the group consisting of O, S and NH;
R is (CH z ) m (CH 3 ) n , wherein z is 0, 1 or 2, m is 0 to 19, and n is 0, 1, 2 or 3. in this case one or more H are optionally = O, -OH, = NH, NH 2, N + Me 3 Cl -,
The method according to claim 28 .
［式中、Ｌは，Ｐ（Ｃ６Ｈ５）３，（ｏ−ｔｏ１）３Ｐ，ＣＨ３ＣＮ，ＤＭＳＯ，Ｎ，Ｎ−ジメチルホルムアミド（ＤＭＦ），
である「請求項１８」記載の方法。 The palladium catalyst has the formula: Pd (0) L 4
[In the formula, L represents P (C 6 H 5 ) 3 , (o-to1) 3 P, CH 3 CN, DMSO, N, N-dimethylformamide (DMF),
The method of claim 18 , wherein:
ＲおよびＲ’は独立にＣ１〜Ｃ２０アルキル（直鎖状または分岐状）、Ｃ２〜Ｃ２０アルケニル（直鎖状または分岐状）、アリール、天然アミノ酸および非天然アミノ酸からなる群より選択され、この場合、ＲおよびＲ’は所望により芳香族、脂肪族または異項環の環構造の一部であってもよく；そして
Ｚは，リボース、デオキシリボースおよびジデオキシリボース、並びにそれらの２’，３’，および５’修飾の組合せのいずれか、からなる群より選択される］
からなる群より選択される化合物。 below:
R and R ′ are independently selected from the group consisting of C 1 -C 20 alkyl (linear or branched), C 2 -C 20 alkenyl (linear or branched), aryl, natural amino acids and unnatural amino acids. Where R and R ′ may optionally be part of an aromatic, aliphatic or heterocyclic ring structure; and Z is ribose, deoxyribose and dideoxyribose , and their 2 ′ , 3 ', and any combination of 5' modifications, selected from the group consisting of]
A compound selected from the group consisting of:
ＲおよびＲ’は独立にＣ１〜Ｃ２０アルキル（直鎖状または分岐状）、Ｃ２〜Ｃ２０アルケニル（直鎖状または分岐状）、アリール、天然アミノ酸および非天然アミノ酸からなる群より選択され、この場合、ＲおよびＲ’は所望により芳香族、脂肪族または異項環の環構造の一部であってもよく；そして
Ｚは，リボース、デオキシリボースおよびジデオキシリボース、並びにそれらの２’，３’，および５’修飾の組合せのいずれか、からなる群より選択される］
からなる群より選択される化合物。 below:
R and R ′ are independently selected from the group consisting of C 1 -C 20 alkyl (linear or branched), C 2 -C 20 alkenyl (linear or branched), aryl, natural amino acids and unnatural amino acids. Where R and R ′ may optionally be part of an aromatic, aliphatic or heterocyclic ring structure; and Z is ribose, deoxyribose and dideoxyribose , and their 2 ′ , 3 ', and any combination of 5' modifications, selected from the group consisting of]
A compound selected from the group consisting of:
Ｒは、（ＣＨｚ）ｍ（ＣＨ３）ｎ（式中、ｚは０，１または２であり、ｍは０〜１９であり、ｎは１，２または３である）であり、この場合１個または２個以上のＨは所望により、＝Ｏ，−ＯＨ，＝ＮＨ，ＮＨ２，Ｎ＋Ｍｅ３Ｃｌ−，
「請求項３６または３７」記載の化合物。 Y is selected from the group consisting of O, S and NH;
R is (CH z ) m (CH 3 ) n , where z is 0, 1 or 2, m is 0 to 19, and n is 1, 2 or 3. One or more H are optionally ═O, —OH, ═NH, NH 2 , N + Me 3 Cl − ,
Ｒ’およびＲ’’は独立にＣ １ 〜Ｃ ２０ アルキル、Ｃ ２ 〜Ｃ ２０ アルケニル、アリール、天然アミノ酸および非天然アミノ酸からなる群より選択され、この場合、Ｒ’およびＲ’’は所望により芳香族、脂肪族または異項環の環構造の一部であってもよく；そして
Ｚは，リボース、デオキシリボースおよびジデオキシリボース、並びにそれらの２’，３’，および５’修飾の組合せのいずれか、からなる群より選択される］
からなる群より選択される化合物。 below:
R ′ and R ″ are independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkenyl, aryl, natural amino acids and unnatural amino acids, wherein R ′ and R ″ are optionally May be part of an aromatic, aliphatic or heterocyclic ring structure; and
Z is selected from the group consisting of ribose, deoxyribose and dideoxyribose, and combinations of their 2 ′, 3 ′, and 5 ′ modifications]
A compound selected from the group consisting of:
Ｒ’は、（ＣＨ ｚ ） ｍ （ＣＨ ３ ） ｎ （式中、ｚは０，１または２であり、ｍは０〜１９であり、ｎは１，２または３である）であり、この場合１個または２個以上のＨは所望により、＝Ｏ，−ＯＨ，＝ＮＨ，ＮＨ ２ ，Ｎ ＋ Ｍｅ ３ Ｃｌ − またはアミノ酸で置換されていてもよい
「請求項４６」記載の化合物。 Y is selected from the group consisting of SR ′ and NHR ′;
R ′ is (CH z ) m (CH 3 ) n , wherein z is 0, 1 or 2, m is 0 to 19, and n is 1, 2 or 3. In some cases, one or more H may optionally be substituted with ═O, —OH, ═NH, NH 2 , N + Me 3 Cl − or an amino acid.
48. A compound according to claim 46 .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45907395A | 1995-06-02 | 1995-06-02 | |
| US08/458,421 US5719273A (en) | 1993-06-14 | 1995-06-02 | Palladium catalyzed nucleoside modifications methods using nucleophiles and carbon monoxide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Division JP4899014B2 (en) | 1995-06-02 | 1996-05-30 | Palladium-catalyzed nucleoside modification method using nucleophiles and carbon monoxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009057388A JP2009057388A (en) | 2009-03-19 |
| JP2009057388A5 true JP2009057388A5 (en) | 2009-09-03 |
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ID=40553446
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Expired - Lifetime JP4899014B2 (en) | 1995-06-02 | 1996-05-30 | Palladium-catalyzed nucleoside modification method using nucleophiles and carbon monoxide |
| JP2008262208A Pending JP2009057388A (en) | 1995-06-02 | 2008-10-08 | Palladium-catalyzed nucleoside modification method using nucleophile and carbon monoxide |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Expired - Lifetime JP4899014B2 (en) | 1995-06-02 | 1996-05-30 | Palladium-catalyzed nucleoside modification method using nucleophiles and carbon monoxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP4899014B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5993279A (en) * | 1982-11-17 | 1984-05-29 | 富士通株式会社 | Method of separately extracting card and receipt by robot |
| JP4899014B2 (en) * | 1995-06-02 | 2012-03-21 | イーシー・テクノロジー・エルエルシー | Palladium-catalyzed nucleoside modification method using nucleophiles and carbon monoxide |
| US7947447B2 (en) | 2007-01-16 | 2011-05-24 | Somalogic, Inc. | Method for generating aptamers with improved off-rates |
| JP5684568B2 (en) * | 2007-07-17 | 2015-03-11 | ソマロジック・インコーポレーテッド | Method for generating aptamers with improved off-rate |
| SG184497A1 (en) * | 2010-04-12 | 2012-11-29 | Somalogic Inc | 5-position modified pyrimidines and their use |
| JP7008405B2 (en) * | 2013-11-21 | 2022-01-25 | ソマロジック・インコーポレーテッド | Cytidine-5-carboxamide modified nucleotide compositions and related methods |
| KR102269009B1 (en) * | 2016-03-14 | 2021-06-28 | 소마로직, 인크. | Compounds and methods for the synthesis of 5-(N-protected-tryptaminocarboxyamide)-2''-deoxyuridine phosphoramidite for incorporation into nucleic acids |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5536418A (en) * | 1978-09-08 | 1980-03-14 | Yamasa Shoyu Co Ltd | 8-substituted adenosine derivative and its preparation |
| JPS5862190A (en) * | 1981-10-07 | 1983-04-13 | Yamasa Shoyu Co Ltd | Production of orotidine derivative |
| US5428149A (en) * | 1993-06-14 | 1995-06-27 | Washington State University Research Foundation | Method for palladium catalyzed carbon-carbon coulping and products |
| JP4899014B2 (en) * | 1995-06-02 | 2012-03-21 | イーシー・テクノロジー・エルエルシー | Palladium-catalyzed nucleoside modification method using nucleophiles and carbon monoxide |
-
1996
- 1996-05-30 JP JP53665296A patent/JP4899014B2/en not_active Expired - Lifetime
-
2008
- 2008-10-08 JP JP2008262208A patent/JP2009057388A/en active Pending
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