JP2004508304A5 - - Google Patents
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- JP2004508304A5 JP2004508304A5 JP2002523445A JP2002523445A JP2004508304A5 JP 2004508304 A5 JP2004508304 A5 JP 2004508304A5 JP 2002523445 A JP2002523445 A JP 2002523445A JP 2002523445 A JP2002523445 A JP 2002523445A JP 2004508304 A5 JP2004508304 A5 JP 2004508304A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- alkenyl
- groups
- Prior art date
- 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
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- -1 heterocyclylamino Chemical group 0.000 claims description 138
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 102100002884 MC4R Human genes 0.000 claims description 4
- 101700072329 MC4R Proteins 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 13
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 12
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 206010012601 Diabetes mellitus Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims 3
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 3
- 125000005842 heteroatoms Chemical group 0.000 claims 3
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 claims 3
- 230000001404 mediated Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrugs Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 47
- 125000003277 amino group Chemical compound 0.000 description 46
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 34
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 28
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- HHLJUSLZGFYWKW-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;hydron;chloride Chemical compound Cl.OCCN(CCO)CCO HHLJUSLZGFYWKW-UHFFFAOYSA-N 0.000 description 3
- 125000004352 2-phenylcyclohexyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZXAZWXJOKVUXST-UHFFFAOYSA-N 3'-methyl-N-(3'-methylspiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carbonyl)-N-(2-morpholin-4-ylethyl)spiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carboxamide Chemical compound C1=2C(C)=C(C(=O)N(CCN3CCOCC3)C(=O)C3=C(C=4C5(SCCS5)CCCC=4O3)C)OC=2CCCC21SCCS2 ZXAZWXJOKVUXST-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical compound [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
- 229940117957 TRIETHANOLAMINE HYDROCHLORIDE Drugs 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000002821 scintillation proximity assay Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- GMRODCVDNXSFAA-UHFFFAOYSA-N 1,3-dimethylbenzene Chemical compound [CH2]C1=CC=CC(C)=C1 GMRODCVDNXSFAA-UHFFFAOYSA-N 0.000 description 1
- AQLZTHZLYFFVIJ-UHFFFAOYSA-N 2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C(C(C)(C)N)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O AQLZTHZLYFFVIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical compound [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical compound [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GXFNBCKBVWMOEW-VTYYSHTASA-N 4-[[N-(2-adamantyl)-C-[(3S)-3-methylpiperazin-1-yl]carbonimidoyl]amino]-N-[2-(2,4-dichlorophenyl)ethyl]benzamide Chemical compound C1CN[C@@H](C)CN1C(\NC=1C=CC(=CC=1)C(=O)NCCC=1C(=CC(Cl)=CC=1)Cl)=N\C1C(C2)CC3CC2CC1C3 GXFNBCKBVWMOEW-VTYYSHTASA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical compound [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UOHUTMGUEZCFRD-ULJHMMPZSA-N C1(NCCC1)\C=C(/N1CCNCC1)\NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCC1)\C=C(/N1CCNCC1)\NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl UOHUTMGUEZCFRD-ULJHMMPZSA-N 0.000 description 1
- KNLMHWSCNOCXCX-SJIPCVTESA-N C1(NCCCC1)C=C(/N(CC1=CC=CC=C1)CC=1NC=CN1)NC1=CC=C(C=C1)C(=O)NCCC1=CC=CC=C1 Chemical compound C1(NCCCC1)C=C(/N(CC1=CC=CC=C1)CC=1NC=CN1)NC1=CC=C(C=C1)C(=O)NCCC1=CC=CC=C1 KNLMHWSCNOCXCX-SJIPCVTESA-N 0.000 description 1
- RLUSOBKCYXAKSI-JLPGSUDCSA-N C1(NCCCC1)C=C(/N1CC(NCC1)=O)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CC(NCC1)=O)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl RLUSOBKCYXAKSI-JLPGSUDCSA-N 0.000 description 1
- HSRXIQJMZZNUGP-YQYKVWLJSA-N C1(NCCCC1)C=C(/N1CC(NCC1)C1=CC=CC=C1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CC(NCC1)C1=CC=CC=C1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl HSRXIQJMZZNUGP-YQYKVWLJSA-N 0.000 description 1
- DFMVFAKJGQHCEJ-ANYBSYGZSA-N C1(NCCCC1)C=C(/N1CCN(CC1)C(=O)C=1OC=CC1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CCN(CC1)C(=O)C=1OC=CC1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl DFMVFAKJGQHCEJ-ANYBSYGZSA-N 0.000 description 1
- PPKQTKUYUHCJEZ-XYGWBWBKSA-N C1(NCCCC1)C=C(/N1CCN2C(NC(C2C1)=O)=N)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CCN2C(NC(C2C1)=O)=N)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl PPKQTKUYUHCJEZ-XYGWBWBKSA-N 0.000 description 1
- BXBNCVUOVXOYHO-BWAHOGKJSA-N C1(NCCCC1)C=C(/N1CCNCC1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CCNCC1)NC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl BXBNCVUOVXOYHO-BWAHOGKJSA-N 0.000 description 1
- DVDBOEOOKYNGTM-ITYLOYPMSA-N C1(NCCCC1)C=C(/N1CCNCC1)NCC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl Chemical compound C1(NCCCC1)C=C(/N1CCNCC1)NCC1=CC=C(C=C1)C(=O)NCCC1=C(C=C(C=C1)Cl)Cl DVDBOEOOKYNGTM-ITYLOYPMSA-N 0.000 description 1
- IULIQGICROPJCC-BCJTWVECSA-N C1(NCCCC1)\C=C(/N(CC1=NC=CC=C1)CC1=CC=C(C=C1)F)\NC1=CC=C(C=C1)C(=O)NCCC1=CC=CC=C1 Chemical compound C1(NCCCC1)\C=C(/N(CC1=NC=CC=C1)CC1=CC=C(C=C1)F)\NC1=CC=C(C=C1)C(=O)NCCC1=CC=CC=C1 IULIQGICROPJCC-BCJTWVECSA-N 0.000 description 1
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-
2001
- 2001-08-21 DZ DZ013415A patent/DZ3415A1/fr active
- 2001-08-31 AT AT01968352T patent/ATE414067T1/de not_active IP Right Cessation
- 2001-08-31 WO PCT/US2001/027206 patent/WO2002018327A2/en not_active Application Discontinuation
- 2001-08-31 BR BR0113643-7A patent/BR0113643A/pt not_active IP Right Cessation
- 2001-08-31 ES ES01968352T patent/ES2316467T3/es not_active Expired - Lifetime
- 2001-08-31 PT PT01968352T patent/PT1409468E/pt unknown
- 2001-08-31 MX MXPA03001813A patent/MXPA03001813A/es active IP Right Grant
- 2001-08-31 EP EP01968352A patent/EP1409468B9/en not_active Expired - Lifetime
- 2001-08-31 AU AU2001288604A patent/AU2001288604B2/en not_active Ceased
- 2001-08-31 SK SK383-2003A patent/SK3832003A3/sk unknown
- 2001-08-31 KR KR10-2003-7003017A patent/KR20030034163A/ko not_active Application Discontinuation
- 2001-08-31 JP JP2002523445A patent/JP4166567B2/ja not_active Expired - Fee Related
- 2001-08-31 EA EA200300323A patent/EA200300323A1/ru unknown
- 2001-08-31 HU HU0302067A patent/HUP0302067A2/hu unknown
- 2001-08-31 SI SI200120058A patent/SI21267A/sl not_active IP Right Cessation
- 2001-08-31 CZ CZ2003882A patent/CZ2003882A3/cs unknown
- 2001-08-31 DE DE60136571T patent/DE60136571D1/de not_active Expired - Lifetime
- 2001-08-31 US US09/945,384 patent/US6638927B2/en not_active Expired - Fee Related
- 2001-08-31 PL PL36069801A patent/PL360698A1/xx not_active Application Discontinuation
- 2001-08-31 CA CA002420694A patent/CA2420694C/en not_active Expired - Fee Related
- 2001-08-31 IL IL15460401A patent/IL154604A0/xx unknown
- 2001-08-31 AU AU8860401A patent/AU8860401A/xx active Pending
- 2001-08-31 AP APAP/P/2003/002755A patent/AP2003002755A0/en unknown
- 2001-08-31 NZ NZ524897A patent/NZ524897A/en unknown
- 2001-08-31 CN CN018177182A patent/CN1659156A/zh active Pending
-
2003
- 2003-02-27 NO NO20030929A patent/NO20030929L/no not_active Application Discontinuation
- 2003-02-28 MA MA27062A patent/MA26948A1/fr unknown
- 2003-03-04 US US10/379,397 patent/US6995269B2/en not_active Expired - Fee Related
- 2003-03-18 BG BG107639A patent/BG107639A/bg unknown
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