NZ538223A - Calcium receptor modulating compound and use thereof - Google Patents

Info

Publication number

NZ538223A

NZ538223A NZ538223A NZ53822303A NZ538223A NZ 538223 A NZ538223 A NZ 538223A NZ 538223 A NZ538223 A NZ 538223A NZ 53822303 A NZ53822303 A NZ 53822303A NZ 538223 A NZ538223 A NZ 538223A

Authority

NZ

New Zealand

Prior art keywords

group

substituted

alkyl

optionally substituted

pyrimidine

Prior art date

2002-08-26

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 241
• 102000013830 Calcium-Sensing Receptors Human genes 0.000 title claims abstract description 12
• 108010050543 Calcium-Sensing Receptors Proteins 0.000 title claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 88
• 239000011575 calcium Substances 0.000 claims abstract description 55
• 239000003814 drug Substances 0.000 claims abstract description 39
• 238000004519 manufacturing process Methods 0.000 claims abstract description 14
• 229910052791 calcium Inorganic materials 0.000 claims abstract description 7
• 201000010099 disease Diseases 0.000 claims abstract description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 6
• 230000005856 abnormality Effects 0.000 claims abstract description 4
• -1 alicyclic hydrocarbon Chemical class 0.000 claims description 521
• 125000001424 substituent group Chemical group 0.000 claims description 207
• 125000000217 alkyl group Chemical group 0.000 claims description 180
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 132
• 125000000623 heterocyclic group Chemical group 0.000 claims description 105
• 125000003118 aryl group Chemical group 0.000 claims description 104
• 150000002430 hydrocarbons Chemical class 0.000 claims description 104
• 229920006395 saturated elastomer Polymers 0.000 claims description 85
• 125000003277 amino group Chemical group 0.000 claims description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims description 73
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
• 229910052717 sulfur Inorganic materials 0.000 claims description 67
• 125000004434 sulfur atom Chemical group 0.000 claims description 67
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 66
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 66
• 125000005842 heteroatom Chemical group 0.000 claims description 64
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 53
• 125000001931 aliphatic group Chemical group 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000002619 bicyclic group Chemical group 0.000 claims description 42
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 40
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• ZMVHEFYHPIJBSW-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2C(C(=O)N)CNN21 ZMVHEFYHPIJBSW-UHFFFAOYSA-N 0.000 claims description 38
• 125000002723 alicyclic group Chemical group 0.000 claims description 38
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 37
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 239000000203 mixture Substances 0.000 claims description 36
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 35
• 125000002252 acyl group Chemical group 0.000 claims description 29
• 229940079593 drug Drugs 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• GCAJUNZLLXNQQO-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2NCCC21 GCAJUNZLLXNQQO-UHFFFAOYSA-N 0.000 claims description 25
• 229930195733 hydrocarbon Natural products 0.000 claims description 25
• 239000004215 Carbon black (E152) Substances 0.000 claims description 24
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 16
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 15
• 229940002612 prodrug Drugs 0.000 claims description 15
• 239000000651 prodrug Substances 0.000 claims description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 208000001132 Osteoporosis Diseases 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 108090000445 Parathyroid hormone Proteins 0.000 claims description 10
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
• 208000020084 Bone disease Diseases 0.000 claims description 8
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
• 125000005110 aryl thio group Chemical group 0.000 claims description 8
• 238000009833 condensation Methods 0.000 claims description 8
• 230000005494 condensation Effects 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 230000028327 secretion Effects 0.000 claims description 8
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 6
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
• 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• SNDMCZNLIBQOCN-UHFFFAOYSA-N 5-(2-fluorophenyl)-2,7,7-trimethyl-N-(3-phenylpentan-3-yl)-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC)(CC)NC(=O)C=1C(C)=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1F SNDMCZNLIBQOCN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 229940123613 Calcium receptor antagonist Drugs 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 230000027455 binding Effects 0.000 claims description 4
• 210000003169 central nervous system Anatomy 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
• 230000001079 digestive effect Effects 0.000 claims description 3
• CJKTUXMCNPTCQS-UHFFFAOYSA-N (2,2-diethyl-4-fluoropyrrolidin-1-yl)-(7,7-dimethyl-5-phenyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidin-3-yl)methanone Chemical compound CCC1(CC)CC(F)CN1C(=O)C1=C(NC(CC2(C)C)C=3C=CC=CC=3)N2N=C1 CJKTUXMCNPTCQS-UHFFFAOYSA-N 0.000 claims description 2
• BXHRVRKLOIWLRF-UHFFFAOYSA-N (2,2-diethyl-4-methoxypyrrolidin-1-yl)-(7,7-dimethyl-5-phenyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidin-3-yl)methanone Chemical compound CCC1(CC)CC(OC)CN1C(=O)C1=C(NC(CC2(C)C)C=3C=CC=CC=3)N2N=C1 BXHRVRKLOIWLRF-UHFFFAOYSA-N 0.000 claims description 2
• HTKBPAYPFBJFAE-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N=1N2CCCNC2=C(C(=O)N)C=1C1=CC=CC=C1 HTKBPAYPFBJFAE-UHFFFAOYSA-N 0.000 claims description 2
• RMLQZXDBDWLNLI-UHFFFAOYSA-N 5-(2-chlorophenyl)-2,7,7-trimethyl-N-[3-(4-methylphenyl)pentan-3-yl]-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C(C)=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1Cl RMLQZXDBDWLNLI-UHFFFAOYSA-N 0.000 claims description 2
• OIPLDJVAZJNLAZ-UHFFFAOYSA-N N-(3-ethylhexan-3-yl)-5-(2-fluorophenyl)-2,7,7-trimethyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCCC(CC)(CC)NC(=O)C=1C(C)=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1F OIPLDJVAZJNLAZ-UHFFFAOYSA-N 0.000 claims description 2
• ZWYZZYLXVBBARS-UHFFFAOYSA-N N-[3-(4-ethylphenyl)pentan-3-yl]-5-(2-fluorophenyl)-2,7,7-trimethyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1C(CC)(CC)NC(=O)C1=C(NC(CC2(C)C)C=3C(=CC=CC=3)F)N2N=C1C ZWYZZYLXVBBARS-UHFFFAOYSA-N 0.000 claims description 2
• QDXRZFVLYYUMGO-UHFFFAOYSA-N chembl1739914 Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C(C)=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1 QDXRZFVLYYUMGO-UHFFFAOYSA-N 0.000 claims description 2
• 229940075993 receptor modulator Drugs 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
• HVJNEZARBXRZAK-UHFFFAOYSA-N (2,2-diethyl-4-phenylmethoxypyrrolidin-1-yl)-(7,7-dimethyl-5-phenyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidin-3-yl)methanone Chemical compound CCC1(CC)CC(OCC=2C=CC=CC=2)CN1C(=O)C=1C=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1 HVJNEZARBXRZAK-UHFFFAOYSA-N 0.000 claims 1
• GBSPWESAARMORA-UHFFFAOYSA-N 5-(2-fluorophenyl)-2,7,7-trimethyl-N-[3-(4-methylphenyl)pentan-3-yl]-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C(C)=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1F GBSPWESAARMORA-UHFFFAOYSA-N 0.000 claims 1
• CSNWDSWUGSIAQN-UHFFFAOYSA-N 7,7-dimethyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1(CCNC=2N1N=CC=2C(=O)N)C CSNWDSWUGSIAQN-UHFFFAOYSA-N 0.000 claims 1
• 150000001555 benzenes Chemical group 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• HUZMHENQDRSAGB-UHFFFAOYSA-N chembl1687946 Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1 HUZMHENQDRSAGB-UHFFFAOYSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 129
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 98
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
• 239000000243 solution Substances 0.000 description 73
• 239000002904 solvent Substances 0.000 description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 62
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 description 51
• 229910001868 water Inorganic materials 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 239000002253 acid Substances 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
• 238000000034 method Methods 0.000 description 37
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 34
• 102000005962 receptors Human genes 0.000 description 33
• 108020003175 receptors Proteins 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
• 125000003944 tolyl group Chemical group 0.000 description 30
• 239000007787 solid Substances 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000002585 base Substances 0.000 description 25
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 23
• 229910052799 carbon Inorganic materials 0.000 description 21
• 231100000989 no adverse effect Toxicity 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• 238000005481 NMR spectroscopy Methods 0.000 description 19
• 229910052783 alkali metal Inorganic materials 0.000 description 19
• 238000004587 chromatography analysis Methods 0.000 description 19
• 238000001914 filtration Methods 0.000 description 19
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 19
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• 239000012267 brine Substances 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 18
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• 238000003818 flash chromatography Methods 0.000 description 17
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• 125000000719 pyrrolidinyl group Chemical group 0.000 description 17
• 230000002829 reductive effect Effects 0.000 description 17
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• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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• 125000003282 alkyl amino group Chemical group 0.000 description 15
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 15
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
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• GDPOLPLUZJZHFL-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=NC2C(C(=O)O)CNN21 GDPOLPLUZJZHFL-UHFFFAOYSA-N 0.000 description 12
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