JP2006502144A - 新規なプリン誘導体、その製造方法および医薬組成物としての使用 - Google Patents

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Publication number

JP2006502144A

JP2006502144A JP2004530172A JP2004530172A JP2006502144A JP 2006502144 A JP2006502144 A JP 2006502144A JP 2004530172 A JP2004530172 A JP 2004530172A JP 2004530172 A JP2004530172 A JP 2004530172A JP 2006502144 A JP2006502144 A JP 2006502144A

Authority

JP

Japan

Prior art keywords

group

alkyl

amino

substituted

piperidin

Prior art date

2002-08-22

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.)

Pending

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• 238000000034 method Methods 0.000 title claims abstract description 9
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims abstract 5
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 104
• 239000000203 mixture Substances 0.000 claims abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 5
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 4
• -1 pyrrolidin-1-ylcarbonyl Chemical group 0.000 claims description 416
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 125000003277 amino group Chemical group 0.000 claims description 34
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 32
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 31
• 125000001624 naphthyl group Chemical group 0.000 claims description 30
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 239000011737 fluorine Substances 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 19
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 18
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 150000001721 carbon Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
• 150000003212 purines Chemical class 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• VLBIYRJVPOZOET-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(2-phenylethylamino)purin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCCC1=CC=CC=C1 VLBIYRJVPOZOET-UHFFFAOYSA-N 0.000 claims description 6
• KXEVVOQPEOZACT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(benzylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=CC=C1 KXEVVOQPEOZACT-UHFFFAOYSA-N 0.000 claims description 6
• WRFSHVCQKQZCJT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-[(4-fluorophenyl)methylamino]-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=C(F)C=C1 WRFSHVCQKQZCJT-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 230000029936 alkylation Effects 0.000 claims description 6
• 238000005804 alkylation reaction Methods 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 239000000651 prodrug Substances 0.000 claims description 6
• 229940002612 prodrug Drugs 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• MUJRWAFVKMBLQJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(dimethylamino)-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N(C)C)=NC=2N=C1N1CCCC(N)C1 MUJRWAFVKMBLQJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical class Cl* 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims description 4
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 4
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 4
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
• RNRPZHYVLILOGM-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-2-methyl-7-(3-methylbut-2-enyl)-1-(naphthalen-1-ylmethyl)purin-6-one Chemical compound N=1C=2N=C(C)N(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 RNRPZHYVLILOGM-UHFFFAOYSA-N 0.000 claims description 4
• UUBYQARNFLJUIF-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(propan-2-ylamino)purin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(NC(C)C)=NC=2N=C1N1CCCC(N)C1 UUBYQARNFLJUIF-UHFFFAOYSA-N 0.000 claims description 4
• LIQQAKDINRZTHI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-piperidin-1-ylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N3CCCCC3)=NC=2N=C1N1CCCC(N)C1 LIQQAKDINRZTHI-UHFFFAOYSA-N 0.000 claims description 4
• KYDFKPMXUILEAA-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-phenacylpurin-6-one Chemical compound C1C(N)CCCN1C(N1CC=2C=CC=CC=2)=NC2=C1C(=O)N(CC(=O)C=1C=CC=CC=1)C=N2 KYDFKPMXUILEAA-UHFFFAOYSA-N 0.000 claims description 4
• DSUCMFGGJJWNGH-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(cyclohexylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NC1CCCCC1 DSUCMFGGJJWNGH-UHFFFAOYSA-N 0.000 claims description 4
• JRQQCSZVFBUCTP-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(cyclohexylmethylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1CCCCC1 JRQQCSZVFBUCTP-UHFFFAOYSA-N 0.000 claims description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 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 4
• 235000013305 food Nutrition 0.000 claims description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
• FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical group O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
• 150000007524 organic acids Chemical class 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• AHRPGBIQGOKCEJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-[(4-methoxynaphthalen-1-yl)methyl]-7-(3-methylbut-2-enyl)purin-6-one Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC=C(C)C)=O)C=NC=1N=C2N1CCCC(N)C1 AHRPGBIQGOKCEJ-UHFFFAOYSA-N 0.000 claims description 3
• KXZCVZCPENDTBZ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-methyl-7-(3-methylbut-2-enyl)-2-(2-phenylethyl)purin-6-one Chemical compound CN1C(=O)C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N=C1CCC1=CC=CC=C1 KXZCVZCPENDTBZ-UHFFFAOYSA-N 0.000 claims description 3
• PNOSIUFCRSQTOB-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-(3-methylbut-2-enyl)-1-(naphthalen-1-ylmethyl)purin-6-one Chemical compound N=1C=2N=CN(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 PNOSIUFCRSQTOB-UHFFFAOYSA-N 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• MLEOPWDMSPGAJV-UHFFFAOYSA-N 2-amino-8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N)=NC=2N=C1N1CCCC(N)C1 MLEOPWDMSPGAJV-UHFFFAOYSA-N 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• LNUIDEMUMXLMOV-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-(piperidin-4-ylmethyl)-3h-purin-6-one Chemical compound C=1C=C(F)C=CC=1CN1C=2C(O)=NC=NC=2N=C1CC1CCNCC1 LNUIDEMUMXLMOV-UHFFFAOYSA-N 0.000 claims description 2
• VEJJMWUFHYIMLI-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-[(1-methylpiperidin-4-yl)methyl]-3h-purin-6-one Chemical class C1CN(C)CCC1CC(N1CC=2C=CC(F)=CC=2)=NC2=C1C(=O)NC=N2 VEJJMWUFHYIMLI-UHFFFAOYSA-N 0.000 claims description 2
• IHELHBZSOOCKJI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1,2-dimethylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(C)=NC=2N=C1N1CCCC(N)C1 IHELHBZSOOCKJI-UHFFFAOYSA-N 0.000 claims description 2
• FWURZHRNHYFNNY-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(methylamino)purin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(NC)=NC=2N=C1N1CCCC(N)C1 FWURZHRNHYFNNY-UHFFFAOYSA-N 0.000 claims description 2
• KHCNZQNITHNYGN-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C=NC=2N=C1N1CCCC(N)C1 KHCNZQNITHNYGN-UHFFFAOYSA-N 0.000 claims description 2
• 102000055006 Calcitonin Human genes 0.000 claims description 2
• 108060001064 Calcitonin Proteins 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 208000001132 Osteoporosis Diseases 0.000 claims description 2
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
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• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
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• BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
• 229960004015 calcitonin Drugs 0.000 claims description 2
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
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• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
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• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
• 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
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