KR20050062575A - 신규한 1,4-디아자바이사이클로알칸 유도체, 이의 제법 및용도 - Google Patents

Info

Publication number

KR20050062575A

KR20050062575A KR1020057005508A KR20057005508A KR20050062575A KR 20050062575 A KR20050062575 A KR 20050062575A KR 1020057005508 A KR1020057005508 A KR 1020057005508A KR 20057005508 A KR20057005508 A KR 20057005508A KR 20050062575 A KR20050062575 A KR 20050062575A

Authority

KR

South Korea

Prior art keywords

diazabicyclo

nonane

oxadiazol

thiadiazol

methyl

Prior art date

2002-09-30

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.)

Ceased

Links

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• 238000002360 preparation method Methods 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 196
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• 201000010099 disease Diseases 0.000 claims abstract description 51
• 208000035475 disorder Diseases 0.000 claims abstract description 43
• 239000000203 mixture Substances 0.000 claims abstract description 41
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 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 abstract description 35
• 238000011282 treatment Methods 0.000 claims abstract description 19
• 230000001713 cholinergic effect Effects 0.000 claims abstract description 15
• 239000000126 substance Substances 0.000 claims abstract description 15
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 14
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• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 10
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 8
• 230000016160 smooth muscle contraction Effects 0.000 claims abstract description 7
• -1 carboxy, carbamoyl Chemical group 0.000 claims description 268
• 238000000034 method Methods 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 230000007170 pathology Effects 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 229960002715 nicotine Drugs 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 13
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• XJKNACDCUAFDHD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonane Chemical class C1CC2CCN1CCN2 XJKNACDCUAFDHD-UHFFFAOYSA-N 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 9
• ONRJLIHAZBFWNG-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1H-imidazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CNC=N1 ONRJLIHAZBFWNG-UHFFFAOYSA-N 0.000 claims description 8
• ZLJFNFOWAPIIAA-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1H-imidazol-5-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C1=CNC=N1 ZLJFNFOWAPIIAA-UHFFFAOYSA-N 0.000 claims description 8
• KYUHZIBROZKXBY-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1h-1,2,4-triazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=NC=NN1 KYUHZIBROZKXBY-UHFFFAOYSA-N 0.000 claims description 8
• HLNQLXWDZSAICM-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1h-1,2,4-triazol-5-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C=1N=CNN=1 HLNQLXWDZSAICM-UHFFFAOYSA-N 0.000 claims description 8
• JYDJMHQVSWEBIN-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1h-pyrazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=CNN=1 JYDJMHQVSWEBIN-UHFFFAOYSA-N 0.000 claims description 8
• DTWPEQOKANXDNQ-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(2h-triazol-4-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CNN=N1 DTWPEQOKANXDNQ-UHFFFAOYSA-N 0.000 claims description 8
• CNQUJHTUYKJZPE-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(2h-triazol-4-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C1=CNN=N1 CNQUJHTUYKJZPE-UHFFFAOYSA-N 0.000 claims description 8
• 230000007812 deficiency Effects 0.000 claims description 8
• ZAHXONDIHZTFGK-UHFFFAOYSA-N 4-(1,4-diazabicyclo[3.2.2]nonan-4-yl)thiadiazole Chemical class C1CN(CC2)CCC1N2C1=CSN=N1 ZAHXONDIHZTFGK-UHFFFAOYSA-N 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
• 239000011669 selenium Substances 0.000 claims description 7
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 6
• 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 6
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 6
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 6
• UDVCQCSTPQSBBC-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1h-pyrazol-5-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C=1C=CNN=1 UDVCQCSTPQSBBC-UHFFFAOYSA-N 0.000 claims description 6
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
• 208000012661 Dyskinesia Diseases 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
• 206010000496 acne Diseases 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
• 230000003111 delayed effect Effects 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 206010015037 epilepsy Diseases 0.000 claims description 6
• 235000003642 hunger Nutrition 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 6
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 6
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000004306 triazinyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 230000036506 anxiety Effects 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 229910052711 selenium Inorganic materials 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 125000001724 1,2,3-oxadiazol-4-yl group Chemical group [H]C1=C(*)N=NO1 0.000 claims description 4
• 125000004503 1,2,3-oxadiazol-5-yl group Chemical group O1N=NC=C1* 0.000 claims description 4
• 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 4
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims description 4
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 4
• 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 4
• OYFSJOFWWSQBMT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-1,3,4-oxadiazole Chemical compound C1CC2CCN1CCN2C1=NN=C(C=2SC3=CC=CC=C3N=2)O1 OYFSJOFWWSQBMT-UHFFFAOYSA-N 0.000 claims description 4
• NLQJILYWMLFJCV-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2,5-oxadiazol-3-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=NON=1 NLQJILYWMLFJCV-UHFFFAOYSA-N 0.000 claims description 4
• UNESTALUVUQDDM-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-oxazol-3-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=CON=1 UNESTALUVUQDDM-UHFFFAOYSA-N 0.000 claims description 4
• NNQKXXGQQBUTIC-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-oxazol-4-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=NOC=1 NNQKXXGQQBUTIC-UHFFFAOYSA-N 0.000 claims description 4
• NMFROYKXWROPJI-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-oxazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CC=NO1 NMFROYKXWROPJI-UHFFFAOYSA-N 0.000 claims description 4
• ZRRBVFTZBFOFEI-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-thiazol-3-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=CSN=1 ZRRBVFTZBFOFEI-UHFFFAOYSA-N 0.000 claims description 4
• UCNKIDBACUXCOH-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-thiazol-3-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C=1C=CSN=1 UCNKIDBACUXCOH-UHFFFAOYSA-N 0.000 claims description 4
• AQEGXBBFYYLDSZ-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,2-thiazol-4-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C=1C=NSC=1 AQEGXBBFYYLDSZ-UHFFFAOYSA-N 0.000 claims description 4
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• BSGRTFYVKPTHPW-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-oxazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CN=CO1 BSGRTFYVKPTHPW-UHFFFAOYSA-N 0.000 claims description 4
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• MDOPFIPYJAYIPO-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-thiazol-2-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C1=NC=CS1 MDOPFIPYJAYIPO-UHFFFAOYSA-N 0.000 claims description 4
• MLBLJATWLQZEFG-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-thiazol-4-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CSC=N1 MLBLJATWLQZEFG-UHFFFAOYSA-N 0.000 claims description 4
• TULHEPAQOLDIKU-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-thiazol-4-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C1=CSC=N1 TULHEPAQOLDIKU-UHFFFAOYSA-N 0.000 claims description 4
• OLAMYGRCMDEBMD-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-thiazol-5-yl)-1,3,4-oxadiazole Chemical compound C1CN(CC2)CCC1N2C(O1)=NN=C1C1=CN=CS1 OLAMYGRCMDEBMD-UHFFFAOYSA-N 0.000 claims description 4
• WTZNQEYXMITPNF-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,3-thiazol-5-yl)-1,3,4-thiadiazole Chemical compound C1CN(CC2)CCC1N2C(S1)=NN=C1C1=CN=CS1 WTZNQEYXMITPNF-UHFFFAOYSA-N 0.000 claims description 4
• FYIZBMXWPHYOFD-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,8-naphthyridin-2-yl)-1,3,4-oxadiazole Chemical compound C1CC2CCN1CCN2C1=NN=C(C=2N=C3N=CC=CC3=CC=2)O1 FYIZBMXWPHYOFD-UHFFFAOYSA-N 0.000 claims description 4
• QSVZCSPVZSUZEV-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1,8-naphthyridin-2-yl)-1,3,4-thiadiazole Chemical compound C1CC2CCN1CCN2C1=NN=C(C=2N=C3N=CC=CC3=CC=2)S1 QSVZCSPVZSUZEV-UHFFFAOYSA-N 0.000 claims description 4
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• UXAATFJSGRCXGZ-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1-methyl-1,2,4-triazol-3-yl)-1,3,4-thiadiazole Chemical compound CN1C=NC(C=2SC(=NN=2)N2C3CCN(CC3)CC2)=N1 UXAATFJSGRCXGZ-UHFFFAOYSA-N 0.000 claims description 4
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• QHYXYWRQUGGOBG-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1-methylbenzimidazol-2-yl)-1,3,4-thiadiazole Chemical compound N=1C2=CC=CC=C2N(C)C=1C(S1)=NN=C1N1CCN2CCC1CC2 QHYXYWRQUGGOBG-UHFFFAOYSA-N 0.000 claims description 4
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• ZZBJLHNFUPGSTG-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1-methylimidazol-2-yl)-1,3,4-thiadiazole Chemical compound CN1C=CN=C1C1=NN=C(N2C3CCN(CC3)CC2)S1 ZZBJLHNFUPGSTG-UHFFFAOYSA-N 0.000 claims description 4
• SSOKKRXFDDAMTE-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1-methylimidazol-4-yl)-1,3,4-oxadiazole Chemical compound CN1C=NC(C=2OC(=NN=2)N2C3CCN(CC3)CC2)=C1 SSOKKRXFDDAMTE-UHFFFAOYSA-N 0.000 claims description 4
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