AU2001239331A1 - Derivatives of quinoline as alpha-2 antagonists - Google Patents
Derivatives of quinoline as alpha-2 antagonistsInfo
- Publication number
- AU2001239331A1 AU2001239331A1 AU2001239331A AU3933101A AU2001239331A1 AU 2001239331 A1 AU2001239331 A1 AU 2001239331A1 AU 2001239331 A AU2001239331 A AU 2001239331A AU 3933101 A AU3933101 A AU 3933101A AU 2001239331 A1 AU2001239331 A1 AU 2001239331A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- phenyl
- compound
- alkoxy
- mono
- 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.)
- Abandoned
Links
- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 title description 12
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 200
- 150000001875 compounds Chemical class 0.000 claims description 136
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000003282 alkyl amino group Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- -1 1- imidazolyl Chemical group 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000005557 antagonist Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 210000003169 central nervous system Anatomy 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 9
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 5
- YEGLCEJPSSYEQE-UHFFFAOYSA-N 3-ethyl-2-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound CCC1=C(C)N=C2C=CC=CC2=C1NC(C=C1)=CC=C1N1CCN(C)CC1 YEGLCEJPSSYEQE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QYNDZEYXHRVXBK-UHFFFAOYSA-N 2,7-dimethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C=12CC(C)CCC2=NC2=CC=C(C)C=C2C=1NC(C=C1)=CC=C1N1CCN(C)CC1 QYNDZEYXHRVXBK-UHFFFAOYSA-N 0.000 claims description 3
- GZPDMTWJWCKXNJ-UHFFFAOYSA-N 2-[4-[4-(1,2,3,4-tetrahydroacridin-9-ylamino)phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=C(CCCC2)C2=NC2=CC=CC=C12 GZPDMTWJWCKXNJ-UHFFFAOYSA-N 0.000 claims description 3
- VBDVCLHMPVSOQZ-UHFFFAOYSA-N 2-[4-[4-(acridin-9-ylamino)phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 VBDVCLHMPVSOQZ-UHFFFAOYSA-N 0.000 claims description 3
- VHXSDKWBFNFFHS-UHFFFAOYSA-N 2-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C=12CC(C)CCC2=NC2=CC=CC=C2C=1NC(C=C1)=CC=C1N1CCN(C)CC1 VHXSDKWBFNFFHS-UHFFFAOYSA-N 0.000 claims description 3
- MKIZKMFJTXEUHC-UHFFFAOYSA-N 2-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=CC(C)=NC2=CC=CC=C12 MKIZKMFJTXEUHC-UHFFFAOYSA-N 0.000 claims description 3
- NAUGYWORANWRRP-UHFFFAOYSA-N 3-ethyl-6-methoxy-2-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound CCC1=C(C)N=C2C=CC(OC)=CC2=C1NC(C=C1)=CC=C1N1CCN(C)CC1 NAUGYWORANWRRP-UHFFFAOYSA-N 0.000 claims description 3
- WWLIQWZZBMOLAS-UHFFFAOYSA-N 8-fluoro-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(CCCC2)C2=NC2=CC=CC(F)=C12 WWLIQWZZBMOLAS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- YTMDIHJFKUKUBO-UHFFFAOYSA-N n-(2,5-diethoxy-4-morpholin-4-ylphenyl)acridin-9-amine Chemical compound CCOC=1C=C(NC=2C3=CC=CC=C3N=C3C=CC=CC3=2)C(OCC)=CC=1N1CCOCC1 YTMDIHJFKUKUBO-UHFFFAOYSA-N 0.000 claims description 3
- ZHMTVZXBRVBKJJ-UHFFFAOYSA-N n-[4-(4-cyclopropylpiperazin-1-yl)phenyl]acridin-9-amine Chemical compound C1CC1N1CCN(C=2C=CC(NC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=CC=2)CC1 ZHMTVZXBRVBKJJ-UHFFFAOYSA-N 0.000 claims description 3
- CPXJYPKLTDRTNF-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4,5,6,7,8-octahydroacridin-9-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(CCCC2)C2=NC2=C1CCCC2 CPXJYPKLTDRTNF-UHFFFAOYSA-N 0.000 claims description 3
- ASJSNRRPCZXGRL-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(CCCC2)C2=NC2=CC=CC=C12 ASJSNRRPCZXGRL-UHFFFAOYSA-N 0.000 claims description 3
- LVWWUTHVDJHKIR-UHFFFAOYSA-N n-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]acridin-9-amine Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 LVWWUTHVDJHKIR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- YAPCYKZPQAMZQI-UHFFFAOYSA-N 2,3-dimethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(C)C(C)=NC2=CC=CC=C12 YAPCYKZPQAMZQI-UHFFFAOYSA-N 0.000 claims description 2
- CEAASZYIQFCQJH-UHFFFAOYSA-N 3-ethyl-2,6-dimethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound CCC1=C(C)N=C2C=CC(C)=CC2=C1NC(C=C1)=CC=C1N1CCN(C)CC1 CEAASZYIQFCQJH-UHFFFAOYSA-N 0.000 claims description 2
- GZBPAEYFMVRUNB-UHFFFAOYSA-N 3-ethyl-2,8-dimethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound CCC1=C(C)N=C2C(C)=CC=CC2=C1NC(C=C1)=CC=C1N1CCN(C)CC1 GZBPAEYFMVRUNB-UHFFFAOYSA-N 0.000 claims description 2
- MAUXHXJBQAWVSI-UHFFFAOYSA-N 3-ethyl-n,2-dimethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]quinolin-4-amine Chemical compound CCC1=C(C)N=C2C=CC=CC2=C1N(C)C(C=C1)=CC=C1N1CCN(C)CC1 MAUXHXJBQAWVSI-UHFFFAOYSA-N 0.000 claims description 2
- YZUCBZHBBMZNFL-UHFFFAOYSA-N 4-(3-chloro-4-imidazol-1-ylanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1N1C=CN=C1 YZUCBZHBBMZNFL-UHFFFAOYSA-N 0.000 claims description 2
- BXVCYRBPPBQKEN-UHFFFAOYSA-N 4-[4-(4-methylpiperazin-1-yl)anilino]quinoline-3-carbonitrile Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(C#N)C=NC2=CC=CC=C12 BXVCYRBPPBQKEN-UHFFFAOYSA-N 0.000 claims description 2
- DUYKGBPLYMVLEY-UHFFFAOYSA-N 4-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-n,n-diethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(CC)CC)CCN1C(C=C1)=CC=C1NC1=C(C=CC(Cl)=C2)C2=NC2=CC=C(OC)C=C12 DUYKGBPLYMVLEY-UHFFFAOYSA-N 0.000 claims description 2
- QSUPSFCOOLCORC-UHFFFAOYSA-N 4-methoxy-n-[4-(4-methylpiperazin-1-yl)phenyl]acridin-9-amine Chemical compound C12=CC=CC=C2N=C2C(OC)=CC=CC2=C1NC(C=C1)=CC=C1N1CCN(C)CC1 QSUPSFCOOLCORC-UHFFFAOYSA-N 0.000 claims description 2
- GOVQEKRSQZBPAX-UHFFFAOYSA-N [1-[4-(acridin-9-ylamino)phenyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 GOVQEKRSQZBPAX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- KJQWJHXJHKKTTD-UHFFFAOYSA-N n-[4-(4-benzylpiperazin-1-yl)phenyl]acridin-9-amine Chemical compound C1CN(C=2C=CC(NC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=CC=2)CCN1CC1=CC=CC=C1 KJQWJHXJHKKTTD-UHFFFAOYSA-N 0.000 claims description 2
- LDFIRHZOIKFLQJ-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-7,8,9,10-tetrahydro-6h-cyclohepta[b]quinolin-11-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(CCCCC2)C2=NC2=CC=CC=C12 LDFIRHZOIKFLQJ-UHFFFAOYSA-N 0.000 claims description 2
- SKJFMEQTIWVLCD-UHFFFAOYSA-N n-[4-(4-methylpiperidin-1-yl)phenyl]acridin-9-amine Chemical compound C1CC(C)CCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 SKJFMEQTIWVLCD-UHFFFAOYSA-N 0.000 claims description 2
- SSSIZHIHVRNNHH-UHFFFAOYSA-N n-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]acridin-9-amine Chemical compound C=12C=CC=CC2=NC2=CC=CC=C2C=1N(C)C(C=C1)=CC=C1N1CCN(C)CC1 SSSIZHIHVRNNHH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- FXCDZMFOKWHQFP-UHFFFAOYSA-N 1,1,3,3-tetramethyl-n-[4-(4-methylpiperazin-1-yl)phenyl]-2,4-dihydroacridin-9-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C2C(C)(C)CC(C)(C)CC2=NC2=CC=CC=C12 FXCDZMFOKWHQFP-UHFFFAOYSA-N 0.000 claims 1
- XMXAKWQIZRUKOE-UHFFFAOYSA-N 4-[4-[(7-chloro-2-methylquinolin-4-yl)amino]phenyl]-n,n-diethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(CC)CC)CCN1C(C=C1)=CC=C1NC1=CC(C)=NC2=CC(Cl)=CC=C12 XMXAKWQIZRUKOE-UHFFFAOYSA-N 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- NOJDKJGJUVAORM-UHFFFAOYSA-N n-(4-pyrrolidin-1-ylphenyl)acridin-9-amine Chemical compound C1CCCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 NOJDKJGJUVAORM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 17
- 229960003002 atipamezole Drugs 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- KGIGZIBMXZQUSF-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)acridin-9-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 KGIGZIBMXZQUSF-UHFFFAOYSA-N 0.000 description 12
- MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 10
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 7
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- 230000008485 antagonism Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
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- HRLIOXLXPOHXTA-NSHDSACASA-N dexmedetomidine Chemical compound C1([C@@H](C)C=2C(=C(C)C=CC=2)C)=CN=C[N]1 HRLIOXLXPOHXTA-NSHDSACASA-N 0.000 description 6
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- 239000000556 agonist Substances 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
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Classifications
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- C—CHEMISTRY; METALLURGY
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
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- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
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- Cardiology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
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- Child & Adolescent Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20000480 | 2000-03-01 | ||
| FI20000480A FI20000480A0 (fi) | 2000-03-01 | 2000-03-01 | Kinoliini- ja naftaleenijohdannaisia alfa-2 antagonisteina |
| PCT/FI2001/000203 WO2001064645A2 (fr) | 2000-03-01 | 2001-02-28 | Derives de quinoline utilises comme antagonistes alpha2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001239331A1 true AU2001239331A1 (en) | 2001-09-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2001239331A Abandoned AU2001239331A1 (en) | 2000-03-01 | 2001-02-28 | Derivatives of quinoline as alpha-2 antagonists |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1263733A2 (fr) |
| JP (1) | JP2003525274A (fr) |
| KR (1) | KR20020089372A (fr) |
| CN (1) | CN1468224A (fr) |
| AR (1) | AR034249A1 (fr) |
| AU (1) | AU2001239331A1 (fr) |
| BR (1) | BR0108816A (fr) |
| CA (1) | CA2400657A1 (fr) |
| CZ (1) | CZ20022880A3 (fr) |
| EE (1) | EE200200490A (fr) |
| FI (1) | FI20000480A0 (fr) |
| HU (1) | HUP0204458A3 (fr) |
| IL (1) | IL151093A0 (fr) |
| MX (1) | MXPA02008402A (fr) |
| NO (1) | NO20024159D0 (fr) |
| PE (1) | PE20011084A1 (fr) |
| PL (1) | PL357874A1 (fr) |
| RU (1) | RU2002125944A (fr) |
| SK (1) | SK12332002A3 (fr) |
| WO (1) | WO2001064645A2 (fr) |
| ZA (1) | ZA200206956B (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2003203148A1 (en) * | 2002-02-05 | 2003-09-02 | High Point Pharmaceuticals, Llc | Novel aryl- and heteroarylpiperazines |
| AU2003219199A1 (en) * | 2002-04-03 | 2003-10-13 | Orion Corporation | Use of an alfa2-adrenoreceptor antagonist for cns-related diseases |
| PL372657A1 (en) | 2002-04-03 | 2005-07-25 | Orion Corporation | Polycyclic compounds as potent alpha2-adrenoceptor antagonists |
| JP2005536462A (ja) * | 2002-04-30 | 2005-12-02 | ユン ジン ファーマスーチカル インダストリーズ カンパニー リミテッド | カスパーゼ−３阻害剤としてのキノリン誘導体、この製造方法及びこれを含む薬剤学的組成物 |
| WO2004067513A1 (fr) * | 2003-01-27 | 2004-08-12 | Oy Juvantia Pharma Ltd | Antagonistes pour recepteurs alpha-2 adrenergiques |
| MX2007015675A (es) | 2005-07-04 | 2008-02-20 | Novo Nordisk As | Antagonistas del receptor de histamina h3. |
| EP1948629A1 (fr) | 2005-10-31 | 2008-07-30 | Janssen Pharmaceutica N.V. | Piperazines et piperidines substituees en tant que modulateurs du recepteur du neuropeptide y2 |
| AU2006333522A1 (en) * | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf. | Biaryl nitrogen heterocycle inhibitors of LTA4H for treating inflammation |
| JP2009537602A (ja) * | 2006-05-22 | 2009-10-29 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 薬剤として用いるための置換ピラジノン誘導体 |
| EP2038256A1 (fr) | 2006-05-23 | 2009-03-25 | TransTech Pharma, Inc | 6-(4-cyclopropylpiperazin-1-yl)-2'-methyl-[3,4']-bipyridine et son utilisation comme medicament |
| CN101460487A (zh) | 2006-05-29 | 2009-06-17 | 高点制药有限责任公司 | 3-(1，3-苯并间二氧杂环戊烯- 5-基)-6-(4-环丙基哌嗪-1-基)-哒嗪、其盐和溶剂合物及其作为组胺h3受体拮抗剂的用途 |
| EP2014656A3 (fr) | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | Nouveaux antagonistes d'hétéocycliques h3 |
| TWI457122B (zh) | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| WO2010042473A1 (fr) | 2008-10-07 | 2010-04-15 | Schering Corporation | Analogues de biaryl-spiroaminooxazoline en tant que modulateurs de récepteur adrénergique alpha2c |
| TW201024282A (en) | 2008-11-20 | 2010-07-01 | Orion Corp | New pharmaceutical compounds |
| AU2010329847A1 (en) | 2009-12-11 | 2012-07-26 | Genecode As | Methods of facilitating neural cell survival using GDNF family ligand (GFL) mimetics or RET signaling pathway activators |
| CN103524413B (zh) * | 2012-07-04 | 2016-04-20 | 江苏先声药物研究有限公司 | 氢化吖啶衍生物及其应用 |
| JOP20200052A1 (ar) * | 2013-12-19 | 2017-06-16 | Bayer Pharma AG | بيبريدينيل تتراهيدرو كوينولينات مستبدلة واستخدامها كمعضدات مستقبل أدريني ألفا- 2c |
| WO2015153535A1 (fr) * | 2014-03-31 | 2015-10-08 | MiRx Pharmaceuticals, LLC | Nouveaux inhibiteurs hdmx et leur utilisation dans le traitement du cancer |
| WO2016135138A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés d'oxoquinoléine en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135140A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 4-aminoquinazoline en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135139A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 2,3-dihydrocyclopenta[b]quinoléine en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135137A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 4-(phénylamino)quinoléine substitués en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| CN107337641B (zh) * | 2017-07-01 | 2020-04-28 | 广东医科大学 | 一种4-柔性胺基-2-芳乙烯基喹啉类衍生物及其制备方法和应用 |
| CA3230249A1 (fr) * | 2021-09-07 | 2023-03-16 | Paul Gregor | Composes et compositions pharmaceutiques comprenant des inhibiteurs d'interactions de peptide amyloide avec des glycosaminoglycanes, procedes de traitement et utilisation de ceux-c |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9510757D0 (en) * | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
-
2000
- 2000-03-01 FI FI20000480A patent/FI20000480A0/fi unknown
-
2001
- 2001-02-28 SK SK1233-2002A patent/SK12332002A3/sk unknown
- 2001-02-28 CA CA002400657A patent/CA2400657A1/fr not_active Abandoned
- 2001-02-28 WO PCT/FI2001/000203 patent/WO2001064645A2/fr not_active Application Discontinuation
- 2001-02-28 KR KR1020027011453A patent/KR20020089372A/ko not_active Application Discontinuation
- 2001-02-28 JP JP2001563488A patent/JP2003525274A/ja active Pending
- 2001-02-28 EE EEP200200490A patent/EE200200490A/xx unknown
- 2001-02-28 HU HU0204458A patent/HUP0204458A3/hu unknown
- 2001-02-28 EP EP01913918A patent/EP1263733A2/fr not_active Withdrawn
- 2001-02-28 AU AU2001239331A patent/AU2001239331A1/en not_active Abandoned
- 2001-02-28 CN CNA018059236A patent/CN1468224A/zh active Pending
- 2001-02-28 CZ CZ20022880A patent/CZ20022880A3/cs unknown
- 2001-02-28 MX MXPA02008402A patent/MXPA02008402A/es unknown
- 2001-02-28 PL PL01357874A patent/PL357874A1/xx not_active Application Discontinuation
- 2001-02-28 IL IL15109301A patent/IL151093A0/xx unknown
- 2001-02-28 BR BR0108816-5A patent/BR0108816A/pt not_active Application Discontinuation
- 2001-02-28 RU RU2002125944/04A patent/RU2002125944A/ru not_active Application Discontinuation
- 2001-03-01 PE PE2001000208A patent/PE20011084A1/es not_active Application Discontinuation
- 2001-03-01 AR ARP010100993A patent/AR034249A1/es unknown
-
2002
- 2002-08-29 ZA ZA200206956A patent/ZA200206956B/en unknown
- 2002-08-30 NO NO20024159A patent/NO20024159D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2400657A1 (fr) | 2001-09-07 |
| WO2001064645A2 (fr) | 2001-09-07 |
| BR0108816A (pt) | 2002-12-10 |
| FI20000480A0 (fi) | 2000-03-01 |
| NO20024159L (no) | 2002-08-30 |
| PE20011084A1 (es) | 2001-10-25 |
| JP2003525274A (ja) | 2003-08-26 |
| MXPA02008402A (es) | 2003-10-14 |
| CZ20022880A3 (cs) | 2003-06-18 |
| IL151093A0 (en) | 2003-04-10 |
| EP1263733A2 (fr) | 2002-12-11 |
| KR20020089372A (ko) | 2002-11-29 |
| HUP0204458A2 (hu) | 2003-04-28 |
| PL357874A1 (en) | 2004-07-26 |
| NO20024159D0 (no) | 2002-08-30 |
| HUP0204458A3 (en) | 2004-07-28 |
| RU2002125944A (ru) | 2004-02-27 |
| ZA200206956B (en) | 2003-12-01 |
| WO2001064645A3 (fr) | 2001-12-27 |
| EE200200490A (et) | 2003-12-15 |
| AR034249A1 (es) | 2004-02-18 |
| CN1468224A (zh) | 2004-01-14 |
| SK12332002A3 (sk) | 2003-07-01 |
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