JP2014516968A5 - - Google Patents

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Publication number

JP2014516968A5

JP2014516968A5 JP2014511589A JP2014511589A JP2014516968A5 JP 2014516968 A5 JP2014516968 A5 JP 2014516968A5 JP 2014511589 A JP2014511589 A JP 2014511589A JP 2014511589 A JP2014511589 A JP 2014511589A JP 2014516968 A5 JP2014516968 A5 JP 2014516968A5

Authority

JP

Japan

Prior art keywords

formula

compound

alkyl

salt

aryl

Prior art date

2012-05-18

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.)

Granted

Links

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• 150000001875 compounds Chemical class 0.000 claims description 225
• 150000003839 salts Chemical class 0.000 claims description 114
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 110
• 125000003118 aryl group Chemical group 0.000 claims description 101
• 238000000034 method Methods 0.000 claims description 91
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical group 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 10
• 125000003275 alpha amino acid group Chemical group 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 5
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
• 230000002140 halogenating effect Effects 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 230000009466 transformation Effects 0.000 claims description 3
• KUZSBKJSGSKPJH-VXGBXAGGSA-N 5-[(9R)-6-[(3R)-3-methylmorpholin-4-yl]-11-oxa-1,3,5-triazatricyclo[7.4.0.02,7]trideca-2,4,6-trien-4-yl]pyrazin-2-amine Chemical compound C[C@@H]1COCCN1c1nc(nc2N3CCOC[C@H]3Cc12)-c1cnc(N)cn1 KUZSBKJSGSKPJH-VXGBXAGGSA-N 0.000 claims description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• 239000002253 acid Substances 0.000 claims description 2
• 150000004703 alkoxides Chemical class 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims description 2
• AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 239000011630 iodine Substances 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
• 150000004692 metal hydroxides Chemical class 0.000 claims description 2
• 239000007800 oxidant agent Substances 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• FRACPXUHUTXLCX-BELIEFIBSA-N tert-butyl N-{1-[(1S)-1-{[(1R,2S)-1-(benzylcarbamoyl)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}-2-cyclopropylethyl]-2-oxopyridin-3-yl}carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN(C1=O)[C@@H](CC2CC2)C(=O)N[C@@H](C[C@@H]3CCNC3=O)[C@H](C(=O)NCC4=CC=CC=C4)O FRACPXUHUTXLCX-BELIEFIBSA-N 0.000 claims description 2
• 230000015572 biosynthetic process Effects 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• 0 CC(*)NP(COCc1ccccc1)(Oc1ccccc1)=O Chemical compound CC(*)NP(COCc1ccccc1)(Oc1ccccc1)=O 0.000 description 4
• FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 3
• VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
• HKCXKNGHGLCFHK-UHFFFAOYSA-N 2-methoxy-7h-purine Chemical compound COC1=NC=C2NC=NC2=N1 HKCXKNGHGLCFHK-UHFFFAOYSA-N 0.000 description 1
• RRUSGPITJKSLPR-UHFFFAOYSA-N CC(NC(COC)(C[O]=C)O)[Mn] Chemical compound CC(NC(COC)(C[O]=C)O)[Mn] RRUSGPITJKSLPR-UHFFFAOYSA-N 0.000 description 1
• BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical class NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 150000005018 aminopurines Chemical class 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1