OA11501A - Process for the preparation of resin-bound cyclic peptides. - Google Patents

Process for the preparation of resin-bound cyclic peptides. Download PDF

Info

Publication number: OA11501A
Authority: OA; OAPI
Prior art keywords: peptide; leu; lys; asp; arg
Prior art date: 1998-04-15

Application number

OA1200000283A

Other languages

English (en)

Inventor

James J Mencel

Adam W Sledeski

Original Assignee

Aventis Pharm Prod Inc

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.)

1998-04-15

Filing date

2000-10-13

Publication date

2004-05-14

2000-10-13 Application filed by Aventis Pharm Prod Inc filed Critical Aventis Pharm Prod Inc

2004-05-14 Publication of OA11501A publication Critical patent/OA11501A/en

Links

239000011347 resin Substances 0.000 title claims abstract description 125
229920005989 resin Polymers 0.000 title claims abstract description 125
108010069514 Cyclic Peptides Proteins 0.000 title claims abstract description 65
102000001189 Cyclic Peptides Human genes 0.000 title claims abstract description 65
238000000034 method Methods 0.000 title claims abstract description 51
230000008569 process Effects 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims 2
125000000539 amino acid group Chemical group 0.000 claims abstract description 65
239000012634 fragment Substances 0.000 claims abstract description 56
230000015572 biosynthetic process Effects 0.000 claims abstract description 39
108010033276 Peptide Fragments Proteins 0.000 claims abstract description 38
102000007079 Peptide Fragments Human genes 0.000 claims abstract description 38
108090000765 processed proteins & peptides Proteins 0.000 claims description 311
235000001014 amino acid Nutrition 0.000 claims description 147
150000001413 amino acids Chemical class 0.000 claims description 143
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 84
-1 C-terminal amino acid ester Chemical class 0.000 claims description 68
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 46
150000001408 amides Chemical group 0.000 claims description 40
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 38
238000005859 coupling reaction Methods 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 33
230000008878 coupling Effects 0.000 claims description 33
238000010168 coupling process Methods 0.000 claims description 33
ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims description 32
102000004196 processed proteins & peptides Human genes 0.000 claims description 29
FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 21
GVMUJUPXFQFBBZ-GUBZILKMSA-N Ser-Lys-Glu Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(O)=O GVMUJUPXFQFBBZ-GUBZILKMSA-N 0.000 claims description 20
229920001184 polypeptide Polymers 0.000 claims description 17
OIOAKXPMBIZAHL-LURJTMIESA-N (2s)-2-azaniumyl-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoate Chemical compound CC(C)(C)OC(=O)CC[C@H](N)C(O)=O OIOAKXPMBIZAHL-LURJTMIESA-N 0.000 claims description 16
108010009298 lysylglutamic acid Proteins 0.000 claims description 16
CIOWSLJGLSUOME-BQBZGAKWSA-N Lys-Asp Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CC(O)=O CIOWSLJGLSUOME-BQBZGAKWSA-N 0.000 claims description 15
UGTZHPSKYRIGRJ-YUMQZZPRSA-N Lys-Glu Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCC(O)=O UGTZHPSKYRIGRJ-YUMQZZPRSA-N 0.000 claims description 15
108010003700 lysyl aspartic acid Proteins 0.000 claims description 15
238000010647 peptide synthesis reaction Methods 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
DWPCPZJAHOETAG-UHFFFAOYSA-N meso-lanthionine Chemical group OC(=O)C(N)CSCC(N)C(O)=O DWPCPZJAHOETAG-UHFFFAOYSA-N 0.000 claims description 13
125000004122 cyclic group Chemical group 0.000 claims description 12
VVQIIIAZJXTLRE-QMMMGPOBSA-N (2s)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NCCCC[C@H](N)C(O)=O VVQIIIAZJXTLRE-QMMMGPOBSA-N 0.000 claims description 11
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical group SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 11
150000002148 esters Chemical group 0.000 claims description 11
WPWUFUBLGADILS-WDSKDSINSA-N Ala-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O WPWUFUBLGADILS-WDSKDSINSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
210000004899 c-terminal region Anatomy 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000006242 amine protecting group Chemical group 0.000 claims description 6
DYWUPCCKOVTCFZ-LBPRGKRZSA-N (2s)-2-amino-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=C(C[C@H](N)C(O)=O)C2=C1 DYWUPCCKOVTCFZ-LBPRGKRZSA-N 0.000 claims description 5
108010015792 glycyllysine Proteins 0.000 claims description 5
DVBUCBXGDWWXNY-SFHVURJKSA-N (2s)-5-(diaminomethylideneamino)-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C3=CC=CC=C3C2=C1 DVBUCBXGDWWXNY-SFHVURJKSA-N 0.000 claims description 4
QTWZCODKTSUZJN-LJAQVGFWSA-N (2s)-5-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N[C@H](C(O)=O)CCCN=C(N)NS(=O)(=O)C(C(C)=C1C)=C(C)C2=C1OC(C)(C)CC2 QTWZCODKTSUZJN-LJAQVGFWSA-N 0.000 claims description 4
DWPCPZJAHOETAG-IMJSIDKUSA-N L-lanthionine Chemical compound OC(=O)[C@@H](N)CSC[C@H](N)C(O)=O DWPCPZJAHOETAG-IMJSIDKUSA-N 0.000 claims description 4
OBTCMSPFOITUIJ-FSPLSTOPSA-N Val-Asp Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CC(O)=O OBTCMSPFOITUIJ-FSPLSTOPSA-N 0.000 claims description 4
QWXZOFZKSQXPDC-NSHDSACASA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)propanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](C)C(O)=O)C3=CC=CC=C3C2=C1 QWXZOFZKSQXPDC-NSHDSACASA-N 0.000 claims description 3
JDDWRLPTKIOUOF-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-[[4-[2-[bis(4-methylphenyl)methylamino]-2-oxoethoxy]phenyl]-(2,4-dimethoxyphenyl)methyl]carbamate Chemical compound COC1=CC(OC)=CC=C1C(C=1C=CC(OCC(=O)NC(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=CC=1)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 JDDWRLPTKIOUOF-UHFFFAOYSA-N 0.000 claims description 3
101150047265 COR2 gene Proteins 0.000 claims description 3
LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical group CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims description 3
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
OJBNDXHENJDCBA-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-6-(prop-2-enoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCCNC(=O)OCC=C)C(=O)O)C3=CC=CC=C3C2=C1 OJBNDXHENJDCBA-QFIPXVFZSA-N 0.000 claims description 2
UMRUUWFGLGNQLI-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 UMRUUWFGLGNQLI-QFIPXVFZSA-N 0.000 claims description 2
101800005164 Peptide V Proteins 0.000 claims description 2
125000001433 C-terminal amino-acid group Chemical class 0.000 claims 32
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 27
108010080629 tryptophan-leucine Proteins 0.000 claims 22
XKVXSCHXGJOQND-ZOBUZTSGSA-N Val-Asp-Trp Chemical compound CC(C)[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O)N XKVXSCHXGJOQND-ZOBUZTSGSA-N 0.000 claims 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 21
REWSWYIDQIELBE-FXQIFTODSA-N Ala-Val-Ser Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(O)=O REWSWYIDQIELBE-FXQIFTODSA-N 0.000 claims 20
JWTKVPMQCCRPQY-SRVKXCTJSA-N His-Asn-Leu Chemical compound [H]N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(O)=O JWTKVPMQCCRPQY-SRVKXCTJSA-N 0.000 claims 20
YOZCKMXHBYKOMQ-IHRRRGAJSA-N Leu-Arg-Lys Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)O)N YOZCKMXHBYKOMQ-IHRRRGAJSA-N 0.000 claims 20
108010050848 glycylleucine Proteins 0.000 claims 20
IUKIDFVOUHZRAK-QWRGUYRKSA-N Gly-Lys-His Chemical compound NCCCC[C@H](NC(=O)CN)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 IUKIDFVOUHZRAK-QWRGUYRKSA-N 0.000 claims 19
108010025306 histidylleucine Proteins 0.000 claims 18
DRCILAJNUJKAHC-SRVKXCTJSA-N Lys-Glu-Arg Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O DRCILAJNUJKAHC-SRVKXCTJSA-N 0.000 claims 11
102100021277 Beta-secretase 2 Human genes 0.000 claims 9
101710150190 Beta-secretase 2 Proteins 0.000 claims 9
235000019445 benzyl alcohol Nutrition 0.000 claims 9
AIRZWUMAHCDDHR-KKUMJFAQSA-N Lys-Leu-Leu Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O AIRZWUMAHCDDHR-KKUMJFAQSA-N 0.000 claims 7
AIISTODACBDQLW-WDSOQIARSA-N Trp-Leu-Arg Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)=CNC2=C1 AIISTODACBDQLW-WDSOQIARSA-N 0.000 claims 5
108010062796 arginyllysine Proteins 0.000 claims 5
CSHFHJNMIMPJST-HOTGVXAUSA-N methyl (2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate Chemical compound NCC(=O)NCC(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)OC)CC1=CC=CC=C1 CSHFHJNMIMPJST-HOTGVXAUSA-N 0.000 claims 5
LBOVBQONZJRWPV-YUMQZZPRSA-N Asp-Lys-Gly Chemical compound [H]N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(O)=O LBOVBQONZJRWPV-YUMQZZPRSA-N 0.000 claims 4
XQFLFQWOBXPMHW-NHCYSSNCSA-N Asp-Val-His Chemical compound N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CNC=N1)C(=O)O XQFLFQWOBXPMHW-NHCYSSNCSA-N 0.000 claims 4
KYIIALJHAOIAHF-KKUMJFAQSA-N Leu-Leu-His Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 KYIIALJHAOIAHF-KKUMJFAQSA-N 0.000 claims 4
JOSAKOKSPXROGQ-BJDJZHNGSA-N Lys-Ser-Ile Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(O)=O JOSAKOKSPXROGQ-BJDJZHNGSA-N 0.000 claims 4
GGNHBHYDMUDXQB-KBIXCLLPSA-N Ala-Glu-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)N GGNHBHYDMUDXQB-KBIXCLLPSA-N 0.000 claims 3
OMSMPWHEGLNQOD-UWVGGRQHSA-N Asn-Phe Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 OMSMPWHEGLNQOD-UWVGGRQHSA-N 0.000 claims 3
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DYFJZDDQPNIPAB-NHCYSSNCSA-N Glu-Arg-Val Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(O)=O DYFJZDDQPNIPAB-NHCYSSNCSA-N 0.000 claims 3
BXOLYFJYQQRQDJ-MXAVVETBSA-N His-Leu-Ile Chemical compound CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CN=CN1)N BXOLYFJYQQRQDJ-MXAVVETBSA-N 0.000 claims 3
OWRUUFUVXFREBD-KKUMJFAQSA-N Lys-His-Leu Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC(C)C)C(O)=O OWRUUFUVXFREBD-KKUMJFAQSA-N 0.000 claims 3
METZZBCMDXHFMK-BZSNNMDCSA-N Phe-Leu-His Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)O)NC(=O)[C@H](CC2=CC=CC=C2)N METZZBCMDXHFMK-BZSNNMDCSA-N 0.000 claims 3
VPZKQTYZIVOJDV-LMVFSUKVSA-N Thr-Ala Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](C)C(O)=O VPZKQTYZIVOJDV-LMVFSUKVSA-N 0.000 claims 3
108010028295 histidylhistidine Proteins 0.000 claims 3
BIOCIVSVEDFKDJ-GUBZILKMSA-N Arg-Arg-Asp Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(O)=O BIOCIVSVEDFKDJ-GUBZILKMSA-N 0.000 claims 2
WIDVAWAQBRAKTI-YUMQZZPRSA-N Asn-Leu-Gly Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O WIDVAWAQBRAKTI-YUMQZZPRSA-N 0.000 claims 2
VSMYBNPOHYAXSD-GUBZILKMSA-N Asp-Lys-Glu Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(O)=O VSMYBNPOHYAXSD-GUBZILKMSA-N 0.000 claims 2
OGCQGUIWMSBHRZ-CIUDSAMLSA-N Leu-Asn-Ser Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(O)=O OGCQGUIWMSBHRZ-CIUDSAMLSA-N 0.000 claims 2
VIKZGAUAKQZDOF-NRPADANISA-N Val-Ser-Glu Chemical compound CC(C)[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@H](C(O)=O)CCC(O)=O VIKZGAUAKQZDOF-NRPADANISA-N 0.000 claims 2
108010068380 arginylarginine Proteins 0.000 claims 2
PCFGFYKGPMQDBX-FEKONODYSA-N 78355-50-7 Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 PCFGFYKGPMQDBX-FEKONODYSA-N 0.000 claims 1
PVSNBTCXCQIXSE-JYJNAYRXSA-N Arg-Arg-Phe Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PVSNBTCXCQIXSE-JYJNAYRXSA-N 0.000 claims 1
CLICCYPMVFGUOF-IHRRRGAJSA-N Arg-Lys-Leu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(O)=O CLICCYPMVFGUOF-IHRRRGAJSA-N 0.000 claims 1
QTAIIXQCOPUNBQ-QXEWZRGKSA-N Arg-Val-Asp Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(O)=O QTAIIXQCOPUNBQ-QXEWZRGKSA-N 0.000 claims 1
ULBHWNVWSCJLCO-NHCYSSNCSA-N Arg-Val-Glu Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](N)CCCN=C(N)N ULBHWNVWSCJLCO-NHCYSSNCSA-N 0.000 claims 1
FFMIYIMKQIMDPK-BQBZGAKWSA-N Asn-His Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 FFMIYIMKQIMDPK-BQBZGAKWSA-N 0.000 claims 1
RTFWCVDISAMGEQ-SRVKXCTJSA-N Asn-Phe-Asn Chemical compound C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CC(=O)N)N RTFWCVDISAMGEQ-SRVKXCTJSA-N 0.000 claims 1
UGXYFDQFLVCDFC-CIUDSAMLSA-N Asn-Ser-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O UGXYFDQFLVCDFC-CIUDSAMLSA-N 0.000 claims 1
YUELDQUPTAYEGM-XIRDDKMYSA-N Asp-Trp-Leu Chemical compound CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)[C@H](CC(=O)O)N YUELDQUPTAYEGM-XIRDDKMYSA-N 0.000 claims 1
101100285688 Caenorhabditis elegans hrg-7 gene Proteins 0.000 claims 1
102100021699 Eukaryotic translation initiation factor 3 subunit B Human genes 0.000 claims 1
ZWABFSSWTSAMQN-KBIXCLLPSA-N Glu-Ile-Ala Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O ZWABFSSWTSAMQN-KBIXCLLPSA-N 0.000 claims 1
ILWHFUZZCFYSKT-AVGNSLFASA-N Glu-Lys-Leu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(O)=O ILWHFUZZCFYSKT-AVGNSLFASA-N 0.000 claims 1
FKJQNJCQTKUBCD-XPUUQOCRSA-N Gly-Ala-His Chemical compound NCC(=O)N[C@@H](C)C(=O)N[C@@H](CC1=CNC=N1)C(=O)O FKJQNJCQTKUBCD-XPUUQOCRSA-N 0.000 claims 1
VBOBNHSVQKKTOT-YUMQZZPRSA-N Gly-Lys-Ala Chemical compound [H]NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(O)=O VBOBNHSVQKKTOT-YUMQZZPRSA-N 0.000 claims 1
VSLXGYMEHVAJBH-DLOVCJGASA-N His-Ala-Leu Chemical compound [H]N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(O)=O VSLXGYMEHVAJBH-DLOVCJGASA-N 0.000 claims 1
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OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
- C07K17/02—Peptides being immobilised on, or in, an organic carrier
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/635—Parathyroid hormone, i.e. parathormone; Parathyroid hormone-related peptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biochemistry (AREA)
Endocrinology (AREA)
Toxicology (AREA)
Zoology (AREA)
Gastroenterology & Hepatology (AREA)
Analytical Chemistry (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

OA1200000283A 1998-04-15 2000-10-13 Process for the preparation of resin-bound cyclic peptides. OA11501A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US8189798P	1998-04-15	1998-04-15

Publications (1)

Publication Number	Publication Date
OA11501A true OA11501A (en)	2004-05-14

Family

ID=22167111

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000283A OA11501A (en)	1998-04-15	2000-10-13	Process for the preparation of resin-bound cyclic peptides.

Country Status (20)

Country	Link
US (1)	US6569993B1 (cs)
EP (1)	EP1093458A4 (cs)
JP (1)	JP2002511483A (cs)
KR (1)	KR20010085236A (cs)
CN (2)	CN1163504C (cs)
AP (1)	AP1117A (cs)
AU (1)	AU744812B2 (cs)
BG (1)	BG104903A (cs)
BR (1)	BR9909634A (cs)
CA (1)	CA2325572A1 (cs)
CZ (1)	CZ20003798A3 (cs)
EA (1)	EA200001071A1 (cs)
HU (1)	HUP0101629A2 (cs)
IL (1)	IL138338A0 (cs)
NO (1)	NO20005165L (cs)
OA (1)	OA11501A (cs)
PL (1)	PL347103A1 (cs)
SK (1)	SK15352000A3 (cs)
UA (1)	UA72460C2 (cs)
WO (1)	WO1999052933A1 (cs)

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US20040082783A1 (en) *	2002-08-06	2004-04-29	Schafmeister Christian E.	Bis (amino acid) molecular scaffolds
PL1680443T3 (pl)	2003-11-05	2014-02-28	Dana Farber Cancer Inst Inc	Stabilizowane alfa-helikalne peptydy i ich zastosowanie
GB0408958D0 (en) *	2004-04-22	2004-05-26	Pharma Mar Sa	Convergent synthesis for kahalalide compounds
TW200626611A (en) *	2004-09-20	2006-08-01	Lonza Ag	Peptide cyclisation
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ATE469173T1 (de)	2006-10-13	2010-06-15	Lilly Co Eli	Pegyliertes pth als pth-rezeptormodulatoren und ihre verwendung
CN101235080B (zh) *	2007-01-31	2010-09-08	中国科学院上海有机化学研究所	一种达托霉素的合成方法
CA2939778C (en)	2007-01-31	2019-01-29	Dana-Farber Cancer Institute, Inc.	Stabilized p53 peptides and uses thereof
CA2682174C (en)	2007-03-28	2021-04-06	President And Fellows Of Harvard College	Stitched polypeptides
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US20110144303A1 (en) *	2008-04-08	2011-06-16	Aileron Therapeutics, Inc.	Biologically Active Peptidomimetic Macrocycles
JP2012503025A (ja)	2008-09-22	2012-02-02	エルロン・セラピューティクス・インコーポレイテッド	精製されたポリペプチド組成物を調製するための方法
JP2012515172A (ja)	2009-01-14	2012-07-05	エルロン・セラピューティクス・インコーポレイテッド	ペプチド模倣大環状分子
WO2011038049A1 (en)	2009-09-22	2011-03-31	Aileron Therapeutics, Inc.	Peptidomimetic macrocycles
KR20130099938A (ko)	2010-08-13	2013-09-06	에일러론 테라퓨틱스 인코포레이티드	펩티도미메틱 거대고리
CN104039342A (zh)	2011-10-18	2014-09-10	爱勒让治疗公司	拟肽大环化合物
HK1205454A1 (en)	2012-02-15	2015-12-18	Aileron Therapeutics, Inc.	Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles
NZ627528A (en)	2012-02-15	2016-05-27	Aileron Therapeutics Inc	Peptidomimetic macrocycles
SG11201503052RA (en)	2012-11-01	2015-05-28	Aileron Therapeutics Inc	Disubstituted amino acids and methods of preparation and use thereof
MX389354B (es)	2014-09-24	2025-03-20	Aileron Therapeutics Inc	Macrociclos peptidomimeticos y formulaciones de los mismos.
MX2017003797A (es)	2014-09-24	2017-06-15	Aileron Therapeutics Inc	Macrociclos peptidomimeticos y usos de los mismos.
WO2016154058A1 (en)	2015-03-20	2016-09-29	Aileron Therapeutics, Inc.	Peptidomimetic macrocycles and uses thereof
CN106146648B (zh) *	2015-03-26	2020-06-12	深圳翰宇药业股份有限公司	一种甲状旁腺激素类似物的合成方法
WO2017004548A1 (en)	2015-07-01	2017-01-05	Aileron Therapeutics, Inc.	Peptidomimetic macrocycles
JP2018528217A (ja)	2015-09-10	2018-09-27	エルロン・セラピューティクス・インコーポレイテッドＡｉｌｅｒｏｎＴｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ．	Ｍｃｌ−１のモジュレーターとしてのペプチド模倣大環状分子
CN110551178B (zh) *	2018-06-01	2020-07-21	深圳翰宇药业股份有限公司	一种含脯氨酸的首尾环肽合成方法
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1999
- 1999-04-15 SK SK1535-2000A patent/SK15352000A3/sk unknown
- 1999-04-15 HU HU0101629A patent/HUP0101629A2/hu unknown
- 1999-04-15 BR BR9909634-0A patent/BR9909634A/pt not_active IP Right Cessation
- 1999-04-15 AU AU35679/99A patent/AU744812B2/en not_active Ceased
- 1999-04-15 IL IL13833899A patent/IL138338A0/xx unknown
- 1999-04-15 AP APAP/P/2000/001972A patent/AP1117A/en active
- 1999-04-15 PL PL99347103A patent/PL347103A1/xx not_active Application Discontinuation
- 1999-04-15 CN CNB998119709A patent/CN1163504C/zh not_active Expired - Fee Related
- 1999-04-15 CN CNA2004100386677A patent/CN1552737A/zh active Pending
- 1999-04-15 WO PCT/US1999/008435 patent/WO1999052933A1/en not_active Ceased
- 1999-04-15 EA EA200001071A patent/EA200001071A1/ru unknown
- 1999-04-15 KR KR1020007011446A patent/KR20010085236A/ko not_active Ceased
- 1999-04-15 UA UA2000116453A patent/UA72460C2/uk unknown
- 1999-04-15 JP JP2000543489A patent/JP2002511483A/ja active Pending
- 1999-04-15 CA CA002325572A patent/CA2325572A1/en not_active Abandoned
- 1999-04-15 CZ CZ20003798A patent/CZ20003798A3/cs unknown
- 1999-04-15 EP EP99917595A patent/EP1093458A4/en not_active Withdrawn
- 1999-11-18 US US09/442,989 patent/US6569993B1/en not_active Expired - Fee Related
2000
- 2000-10-13 NO NO20005165A patent/NO20005165L/no not_active Application Discontinuation
- 2000-10-13 OA OA1200000283A patent/OA11501A/en unknown
- 2000-11-02 BG BG104903A patent/BG104903A/bg unknown

Also Published As

Publication number	Publication date
CN1552737A (zh)	2004-12-08
CA2325572A1 (en)	1999-10-21
BG104903A (bg)	2001-07-31
CZ20003798A3 (cs)	2001-08-15
HUP0101629A2 (en)	2003-03-28
KR20010085236A (ko)	2001-09-07
AU3567999A (en)	1999-11-01
AP1117A (en)	2002-11-02
AU744812B2 (en)	2002-03-07
NO20005165D0 (no)	2000-10-13
EP1093458A1 (en)	2001-04-25
UA72460C2 (en)	2005-03-15
EA200001071A1 (ru)	2001-08-27
CN1163504C (zh)	2004-08-25
US6569993B1 (en)	2003-05-27
NO20005165L (no)	2000-12-15
IL138338A0 (en)	2001-10-31
AP2000001972A0 (en)	2000-12-31
JP2002511483A (ja)	2002-04-16
CN1323313A (zh)	2001-11-21
WO1999052933A1 (en)	1999-10-21
BR9909634A (pt)	2001-10-16
SK15352000A3 (sk)	2001-04-09
PL347103A1 (en)	2002-03-25
EP1093458A4 (en)	2001-07-18

Publication	Publication Date	Title
AU744812B2 (en)	2002-03-07	Process for the preparation of resin-bound cyclic peptides
US4743677A (en)	1988-05-10	Calcitonin gene related peptide derivatives
EP2448956B1 (en)	2018-05-16	Solid phase peptide synthesis of peptide alcohols
JP2002533299A (ja)	2002-10-08	環状ペプチドの合成
WO2004092202A1 (en)	2004-10-28	Process for production of cyclic peptides
EP0597997B1 (en)	1998-05-20	Lanthionine bridged peptides
US4965343A (en)	1990-10-23	Method of peptide synthesis
KR100493795B1 (ko)	2005-09-09	혈관활성장펩타이드유사체의합성방법
EP0082568A2 (en)	1983-06-29	Retro-inverso analogues of C-terminal penta and hexapeptides of substance P.
GB2058077A (en)	1981-04-08	Enkephalin analogues
US6673769B2 (en)	2004-01-06	Lanthionine bridged peptides
Nishiuchi et al.	2000	Combined solid‐phase and solution approach for the synthesis of large peptides or proteins
US6448031B1 (en)	2002-09-10	Process for producing LH-RH derivatives
JPH051798B2 (cs)	1993-01-11
JP2010537984A (ja)	2010-12-09	ポリペプチドおよび蛋白質の化学合成のための方法および中間体
MXPA00010056A (en)	2001-07-31	Process for the preparation of resin-bound cyclic peptides
AU3708697A (en)	1999-03-01	Process for producing lh-rh derivatives
JPWO1995000546A1 (ja)	1995-08-03	エンドセリン拮抗ペプチド類