SK10692001A3 - Diazabicyklické deriváty, ich použitie a farmaceutický prípravok s ich obsahom - Google Patents

Diazabicyklické deriváty, ich použitie a farmaceutický prípravok s ich obsahom Download PDF

Info

Publication number: SK10692001A3
Authority: SK; Slovakia
Prior art keywords: diazabicyclo; pyridinyl; octane; chloro; heptane
Prior art date: 1999-01-29

Application number

SK1069-2001A

Other languages

English (en)

Slovak (sk)

Inventor

William H. Bunnelle

Daniela Barlocco Cristina

Jerome F. Daanen

Michael J. ?????????????????????????????????????? Dart

Michael D. Meyer

Keith B. Ryther

Michael R. Schrimpf

Kevin B. Sippy

Richard B. Toupence

Original Assignee

Abbott Laboratories

Priority date (The priority date 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 date listed.)

1999-01-29

Filing date

2000-01-25

Publication date

2002-01-07

2000-01-25 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2002-01-07 Publication of SK10692001A3 publication Critical patent/SK10692001A3/sk

Links

108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title description 16
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title description 15
239000003446 ligand Substances 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 230
150000003839 salts Chemical class 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 12
241000124008 Mammalia Species 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 6
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims abstract description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 4
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 3
-1 (1R, 5R) -3- (5-ethynyl-6-fluoro-3-piperidinyl) -3,6-diazabicyclo [3.2.1] octane Chemical compound 0.000 claims description 135
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 24
230000004044 response Effects 0.000 claims description 23
239000003814 drug Substances 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
201000010099 disease Diseases 0.000 claims description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
208000018737 Parkinson disease Diseases 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
208000024827 Alzheimer disease Diseases 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
FQXZEMJVGYXBEY-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-ol Chemical compound OC1=CN=CC(N2C3CC(NC3)C2)=C1 FQXZEMJVGYXBEY-UHFFFAOYSA-N 0.000 claims description 5
CJRLDFQDWXLGLH-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C3CC(NC3)C2)=C1 CJRLDFQDWXLGLH-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
WTIVOXCWVQKFER-UHFFFAOYSA-N 2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound COC1=CN=CC(N2C3CC(NC3)C2)=C1 WTIVOXCWVQKFER-UHFFFAOYSA-N 0.000 claims description 4
ONPXTLLWQNBLPG-UHFFFAOYSA-N 2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(F)=CC=C1N1C(CN2)CC2C1 ONPXTLLWQNBLPG-UHFFFAOYSA-N 0.000 claims description 4
NRFYACWYEJZMRE-PSASIEDQSA-N 2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#N)=C1 NRFYACWYEJZMRE-PSASIEDQSA-N 0.000 claims description 4
ZGHKBXCWIZHPBZ-UHFFFAOYSA-N 2-pyridin-3-yl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC(C2)CC1N2C1=CC=CN=C1 ZGHKBXCWIZHPBZ-UHFFFAOYSA-N 0.000 claims description 4
IYNBYHMSSSABOB-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(N2C3CC(NC3)C2)=C1 IYNBYHMSSSABOB-UHFFFAOYSA-N 0.000 claims description 4
XVNHHYYONOJITJ-UHFFFAOYSA-N [5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl]methanamine Chemical compound NCC1=CN=CC(N2C3CC(NC3)C2)=C1 XVNHHYYONOJITJ-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
208000022531 anorexia Diseases 0.000 claims description 4
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125000004967 formylalkyl group Chemical group 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
230000001105 regulatory effect Effects 0.000 claims description 4
230000005586 smoking cessation Effects 0.000 claims description 4
HSOLSMYRWLJLEZ-PSASIEDQSA-N (1r,4r)-2-(5-bromopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(Br)=C1 HSOLSMYRWLJLEZ-PSASIEDQSA-N 0.000 claims description 3
CBTCGPHDIOYTJM-WPRPVWTQSA-N (1s,4s)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(F)C(C)=C1 CBTCGPHDIOYTJM-WPRPVWTQSA-N 0.000 claims description 3
USXYDBGSWSSTGE-OCAPTIKFSA-N (1s,5r)-3-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1C[C@H](N2)CC[C@H]2C1 USXYDBGSWSSTGE-OCAPTIKFSA-N 0.000 claims description 3
PJZJKCSPIJZHHP-UHFFFAOYSA-N 2-(6-nitropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC([N+](=O)[O-])=CC=C1N1C(CN2)CC2C1 PJZJKCSPIJZHHP-UHFFFAOYSA-N 0.000 claims description 3
NRFYACWYEJZMRE-WPRPVWTQSA-N 2-chloro-5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carbonitrile Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#N)=C1 NRFYACWYEJZMRE-WPRPVWTQSA-N 0.000 claims description 3
LGOWUGJXDAIEML-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C1=NC(Cl)=CC=C1N1CC(N2)CCC2CC1 LGOWUGJXDAIEML-UHFFFAOYSA-N 0.000 claims description 3
RRRYINNWGCSIAD-UHFFFAOYSA-N 9-(6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C1=NC(Cl)=CC=C1N1C2CCC1CCNC2 RRRYINNWGCSIAD-UHFFFAOYSA-N 0.000 claims description 3
208000011231 Crohn disease Diseases 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
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206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
208000000323 Tourette Syndrome Diseases 0.000 claims description 3
208000016620 Tourette disease Diseases 0.000 claims description 3
206010046543 Urinary incontinence Diseases 0.000 claims description 3
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206010015037 epilepsy Diseases 0.000 claims description 3
201000001881 impotence Diseases 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
230000004770 neurodegeneration Effects 0.000 claims description 3
230000004112 neuroprotection Effects 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
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231100000736 substance abuse Toxicity 0.000 claims description 3
208000011117 substance-related disease Diseases 0.000 claims description 3
208000011580 syndromic disease Diseases 0.000 claims description 3
VWVWGINOEMBUOB-HTQZYQBOSA-N (1r,4r)-2-(5,6-dichloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(Cl)=C1 VWVWGINOEMBUOB-HTQZYQBOSA-N 0.000 claims description 2
IBCNMAGSFIKYFO-HTQZYQBOSA-N (1r,4r)-2-(5-bromo-6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(Br)=C1 IBCNMAGSFIKYFO-HTQZYQBOSA-N 0.000 claims description 2
UTMVUYYCSVXPMM-MWLCHTKSSA-N (1r,4r)-2-(5-ethynyl-6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(C#C)=C1 UTMVUYYCSVXPMM-MWLCHTKSSA-N 0.000 claims description 2
XXQBILVDTXLLLR-NXEZZACHSA-N (1r,4r)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-NXEZZACHSA-N 0.000 claims description 2
PJCWGAPXCCOGKP-HUUCEWRRSA-N (1r,4r)-2-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 PJCWGAPXCCOGKP-HUUCEWRRSA-N 0.000 claims description 2
AMOSLJJGHSYKRZ-MWLCHTKSSA-N (1r,4r)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#C)=C1 AMOSLJJGHSYKRZ-MWLCHTKSSA-N 0.000 claims description 2
MYGNZAWJQQWAFE-GHMZBOCLSA-N (1r,4r)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C#C)=C1 MYGNZAWJQQWAFE-GHMZBOCLSA-N 0.000 claims description 2
KDAZWLLKSUFNTG-NXEZZACHSA-N (1r,4r)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C)=C1 KDAZWLLKSUFNTG-NXEZZACHSA-N 0.000 claims description 2
RDBYUTPLHXVJKE-RNFRBKRXSA-N (1r,4r)-2-(6-chloropyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(Cl)N=N1 RDBYUTPLHXVJKE-RNFRBKRXSA-N 0.000 claims description 2
WKMLUGOFDWMYKZ-HTQZYQBOSA-N (1r,4r)-2-(6-chloropyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C1=CC=C(Cl)N=N1 WKMLUGOFDWMYKZ-HTQZYQBOSA-N 0.000 claims description 2
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YDTZQKVJVYSCBP-NXEZZACHSA-N (1r,4r)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(F)C(C)=C1 YDTZQKVJVYSCBP-NXEZZACHSA-N 0.000 claims description 2
RKBKKRAXHYTUND-RKDXNWHRSA-N (1r,4r)-2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=C(F)N=C1 RKBKKRAXHYTUND-RKDXNWHRSA-N 0.000 claims description 2
MDWOWXOFKFFTAB-MWLCHTKSSA-N (1r,4r)-2-(6-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(C)N=C1 MDWOWXOFKFFTAB-MWLCHTKSSA-N 0.000 claims description 2
PJZJKCSPIJZHHP-VXNVDRBHSA-N (1r,4r)-2-(6-nitropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C([N+]([O-])=O)N=C1 PJZJKCSPIJZHHP-VXNVDRBHSA-N 0.000 claims description 2
LINMRUIKENUABZ-HTQZYQBOSA-N (1r,4r)-2-pyridazin-3-yl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=CN=N1 LINMRUIKENUABZ-HTQZYQBOSA-N 0.000 claims description 2
IKJZJZXKGKENDY-MWLCHTKSSA-N (1r,4r)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-MWLCHTKSSA-N 0.000 claims description 2
XWJMSESMIIBXEB-HTQZYQBOSA-N (1r,4r)-2-pyrimidin-5-yl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CN=C1 XWJMSESMIIBXEB-HTQZYQBOSA-N 0.000 claims description 2
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UVORMACRUDDZOI-NXEZZACHSA-N (1r,5r)-3-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=CC(OC)=C1 UVORMACRUDDZOI-NXEZZACHSA-N 0.000 claims description 2
NLBYJBDHHSULMA-MWLCHTKSSA-N (1r,5r)-3-(6-chloro-5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(C#C)=C1 NLBYJBDHHSULMA-MWLCHTKSSA-N 0.000 claims description 2
NSZNGOJYQHWDIQ-NXEZZACHSA-N (1r,5r)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(C)=C1 NSZNGOJYQHWDIQ-NXEZZACHSA-N 0.000 claims description 2
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NVUZRYJGKQGBHY-RKDXNWHRSA-N (1r,5r)-3-(6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CC=C(F)N=C1 NVUZRYJGKQGBHY-RKDXNWHRSA-N 0.000 claims description 2
XVIQZJBHPINOMT-NXEZZACHSA-N (1r,5r)-3-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CC=CN=C1 XVIQZJBHPINOMT-NXEZZACHSA-N 0.000 claims description 2
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PVRLCIPGIOMSTL-MWLCHTKSSA-N (1r,5r)-6-(5-ethynyl-6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(F)C(C#C)=C1 PVRLCIPGIOMSTL-MWLCHTKSSA-N 0.000 claims description 2
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MOALZDBEPGDEKO-MWLCHTKSSA-N (1r,5r)-6-(6-fluoro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(F)C(C)=C1 MOALZDBEPGDEKO-MWLCHTKSSA-N 0.000 claims description 2
ZLHFGGWPDZHAJF-MWLCHTKSSA-N (1r,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CC=CN=C1 ZLHFGGWPDZHAJF-MWLCHTKSSA-N 0.000 claims description 2
BVBCYPSVQQGWJQ-SFYZADRCSA-N (1r,5s)-4-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(Br)=C1 BVBCYPSVQQGWJQ-SFYZADRCSA-N 0.000 claims description 2
FEIGOTKIKSJHSL-PWSUYJOCSA-N (1r,5s)-4-(5-ethynyl-6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(F)C(C#C)=C1 FEIGOTKIKSJHSL-PWSUYJOCSA-N 0.000 claims description 2
VSNFTKFKMDNYIB-ZJUUUORDSA-N (1r,5s)-4-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=CC(OC)=C1 VSNFTKFKMDNYIB-ZJUUUORDSA-N 0.000 claims description 2
GJVAKOWYUPGMPN-PWSUYJOCSA-N (1r,5s)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#C)=C1 GJVAKOWYUPGMPN-PWSUYJOCSA-N 0.000 claims description 2
UAMCTEHVCPWLQF-KOLCDFICSA-N (1r,5s)-4-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(F)C(C)=C1 UAMCTEHVCPWLQF-KOLCDFICSA-N 0.000 claims description 2
OLGUYJHINSBYSV-JGVFFNPUSA-N (1r,5s)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Cl)=C1 OLGUYJHINSBYSV-JGVFFNPUSA-N 0.000 claims description 2
WMYOQZRIEFMPDD-JGVFFNPUSA-N (1r,5s)-7-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Br)=C1 WMYOQZRIEFMPDD-JGVFFNPUSA-N 0.000 claims description 2
VEHCREKPXLGWCI-WDEREUQCSA-N (1r,5s)-7-(5-ethynyl-6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(F)C(C#C)=C1 VEHCREKPXLGWCI-WDEREUQCSA-N 0.000 claims description 2
MXMWDEJGOFAQIF-VHSXEESVSA-N (1r,5s)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=CC(OC)=C1 MXMWDEJGOFAQIF-VHSXEESVSA-N 0.000 claims description 2
LEJILTNCTMWMAF-WDEREUQCSA-N (1r,5s)-7-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C#C)=C1 LEJILTNCTMWMAF-WDEREUQCSA-N 0.000 claims description 2
TVSYLDOEQMXDNJ-VHSXEESVSA-N (1r,5s)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C)=C1 TVSYLDOEQMXDNJ-VHSXEESVSA-N 0.000 claims description 2
DOLPRZLBJYAFEQ-VHSXEESVSA-N (1r,5s)-7-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(F)C(C)=C1 DOLPRZLBJYAFEQ-VHSXEESVSA-N 0.000 claims description 2
LODFTIXAWYPTQJ-DTWKUNHWSA-N (1r,5s)-7-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CC=C(F)N=C1 LODFTIXAWYPTQJ-DTWKUNHWSA-N 0.000 claims description 2
UMPFGRGEHJMUQE-VHSXEESVSA-N (1r,5s)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CC=CN=C1 UMPFGRGEHJMUQE-VHSXEESVSA-N 0.000 claims description 2
CNOZTJDDMVPLRE-BDAKNGLRSA-N (1r,6s)-4-(5,6-dichloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(Cl)=C1 CNOZTJDDMVPLRE-BDAKNGLRSA-N 0.000 claims description 2
GEWXCNBZLXRDAX-BDAKNGLRSA-N (1r,6s)-4-(5-bromo-6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(Br)=C1 GEWXCNBZLXRDAX-BDAKNGLRSA-N 0.000 claims description 2
ZNBQVWOSKWWGGL-NEPJUHHUSA-N (1r,6s)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C#C)=C1 ZNBQVWOSKWWGGL-NEPJUHHUSA-N 0.000 claims description 2
UBKMVKPQYKJIRD-MNOVXSKESA-N (1r,6s)-4-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C)=C1 UBKMVKPQYKJIRD-MNOVXSKESA-N 0.000 claims description 2
LGOWUGJXDAIEML-ZJUUUORDSA-N (1r,6s)-4-(6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CC=C(Cl)N=C1 LGOWUGJXDAIEML-ZJUUUORDSA-N 0.000 claims description 2
TWDYLXRVXNFFCM-MNOVXSKESA-N (1r,6s)-4-(6-fluoro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(F)C(C)=C1 TWDYLXRVXNFFCM-MNOVXSKESA-N 0.000 claims description 2
HSZBYOLSLJPMKJ-ZJUUUORDSA-N (1r,6s)-4-(6-fluoropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CC=C(F)N=C1 HSZBYOLSLJPMKJ-ZJUUUORDSA-N 0.000 claims description 2
IMAFPMMJFGWHQM-MNOVXSKESA-N (1r,6s)-4-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CC=CN=C1 IMAFPMMJFGWHQM-MNOVXSKESA-N 0.000 claims description 2
VESMWSRDNYFMCJ-BDAKNGLRSA-N (1r,6s)-9-(5-bromo-6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(Cl)C(Br)=C1 VESMWSRDNYFMCJ-BDAKNGLRSA-N 0.000 claims description 2
BVWJERRKXCLDKE-NEPJUHHUSA-N (1r,6s)-9-(5-ethynyl-6-fluoropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(F)C(C#C)=C1 BVWJERRKXCLDKE-NEPJUHHUSA-N 0.000 claims description 2
GCYULHICELESPR-MNOVXSKESA-N (1r,6s)-9-(5-methoxypyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=CC(OC)=C1 GCYULHICELESPR-MNOVXSKESA-N 0.000 claims description 2
OTLMADHBSCNZBY-NEPJUHHUSA-N (1r,6s)-9-(6-chloro-5-ethynylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(Cl)C(C#C)=C1 OTLMADHBSCNZBY-NEPJUHHUSA-N 0.000 claims description 2
RRRYINNWGCSIAD-ZJUUUORDSA-N (1r,6s)-9-(6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CC=C(Cl)N=C1 RRRYINNWGCSIAD-ZJUUUORDSA-N 0.000 claims description 2
OTJBPZPCTASYLE-MNOVXSKESA-N (1r,6s)-9-(6-fluoro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(F)C(C)=C1 OTJBPZPCTASYLE-MNOVXSKESA-N 0.000 claims description 2
OUTRZPWGRMOTAU-ZJUUUORDSA-N (1r,6s)-9-(6-fluoropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CC=C(F)N=C1 OUTRZPWGRMOTAU-ZJUUUORDSA-N 0.000 claims description 2
RRTGSZDGKKGSKG-YUMQZZPRSA-N (1s,4s)-2-(2-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CC=CN=C1F RRTGSZDGKKGSKG-YUMQZZPRSA-N 0.000 claims description 2
BOSZMFMAQZTFGS-BQBZGAKWSA-N (1s,4s)-2-(5,6-dichloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(Cl)=C1 BOSZMFMAQZTFGS-BQBZGAKWSA-N 0.000 claims description 2
GMLGNBDJGLARCR-BQBZGAKWSA-N (1s,4s)-2-(5-bromo-6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(Br)=C1 GMLGNBDJGLARCR-BQBZGAKWSA-N 0.000 claims description 2
IBCNMAGSFIKYFO-YUMQZZPRSA-N (1s,4s)-2-(5-bromo-6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(Br)=C1 IBCNMAGSFIKYFO-YUMQZZPRSA-N 0.000 claims description 2
HSOLSMYRWLJLEZ-WPRPVWTQSA-N (1s,4s)-2-(5-bromopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=CC(Br)=C1 HSOLSMYRWLJLEZ-WPRPVWTQSA-N 0.000 claims description 2
UTMVUYYCSVXPMM-ONGXEEELSA-N (1s,4s)-2-(5-ethynyl-6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(F)C(C#C)=C1 UTMVUYYCSVXPMM-ONGXEEELSA-N 0.000 claims description 2
GCTFFQZMKQJPBX-QWRGUYRKSA-N (1s,4s)-2-(5-ethynyl-6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(F)C(C#C)=C1 GCTFFQZMKQJPBX-QWRGUYRKSA-N 0.000 claims description 2
XXQBILVDTXLLLR-UWVGGRQHSA-N (1s,4s)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-UWVGGRQHSA-N 0.000 claims description 2
PJCWGAPXCCOGKP-GJZGRUSLSA-N (1s,4s)-2-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 PJCWGAPXCCOGKP-GJZGRUSLSA-N 0.000 claims description 2
AMOSLJJGHSYKRZ-ONGXEEELSA-N (1s,4s)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#C)=C1 AMOSLJJGHSYKRZ-ONGXEEELSA-N 0.000 claims description 2
MYGNZAWJQQWAFE-QWRGUYRKSA-N (1s,4s)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(C#C)=C1 MYGNZAWJQQWAFE-QWRGUYRKSA-N 0.000 claims description 2
CGIVAYCVSYBNBO-IUCAKERBSA-N (1s,4s)-2-(6-chloro-5-methylpyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C1=CC(C)=C(Cl)N=N1 CGIVAYCVSYBNBO-IUCAKERBSA-N 0.000 claims description 2
FRVGBUBUZLXEJI-WPRPVWTQSA-N (1s,4s)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(C)=C1 FRVGBUBUZLXEJI-WPRPVWTQSA-N 0.000 claims description 2
RDBYUTPLHXVJKE-BQBZGAKWSA-N (1s,4s)-2-(6-chloropyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CC=C(Cl)N=N1 RDBYUTPLHXVJKE-BQBZGAKWSA-N 0.000 claims description 2
WKMLUGOFDWMYKZ-YUMQZZPRSA-N (1s,4s)-2-(6-chloropyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C1=CC=C(Cl)N=N1 WKMLUGOFDWMYKZ-YUMQZZPRSA-N 0.000 claims description 2
UXIMNPXAWUTMIF-IUCAKERBSA-N (1s,4s)-2-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CC=C(Cl)N=C1 UXIMNPXAWUTMIF-IUCAKERBSA-N 0.000 claims description 2
YDTZQKVJVYSCBP-UWVGGRQHSA-N (1s,4s)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(F)C(C)=C1 YDTZQKVJVYSCBP-UWVGGRQHSA-N 0.000 claims description 2
RKBKKRAXHYTUND-IUCAKERBSA-N (1s,4s)-2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CC=C(F)N=C1 RKBKKRAXHYTUND-IUCAKERBSA-N 0.000 claims description 2
HNRIHCBMMRMJDG-WPRPVWTQSA-N (1s,4s)-2-(6-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CC=C(OC)N=C1 HNRIHCBMMRMJDG-WPRPVWTQSA-N 0.000 claims description 2
IKJZJZXKGKENDY-ONGXEEELSA-N (1s,4s)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-ONGXEEELSA-N 0.000 claims description 2
SZIUULMZONBWOH-JGVFFNPUSA-N (1s,5r)-4-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(Cl)C(Cl)=C1 SZIUULMZONBWOH-JGVFFNPUSA-N 0.000 claims description 2
BVBCYPSVQQGWJQ-JGVFFNPUSA-N (1s,5r)-4-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(Cl)C(Br)=C1 BVBCYPSVQQGWJQ-JGVFFNPUSA-N 0.000 claims description 2
VSNFTKFKMDNYIB-VHSXEESVSA-N (1s,5r)-4-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=CC(OC)=C1 VSNFTKFKMDNYIB-VHSXEESVSA-N 0.000 claims description 2
HOFIEMCFOWCLAI-GXSJLCMTSA-N (1s,5r)-4-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(Cl)C(C)=C1 HOFIEMCFOWCLAI-GXSJLCMTSA-N 0.000 claims description 2
UAMCTEHVCPWLQF-GXSJLCMTSA-N (1s,5r)-4-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(F)C(C)=C1 UAMCTEHVCPWLQF-GXSJLCMTSA-N 0.000 claims description 2
OLGUYJHINSBYSV-SFYZADRCSA-N (1s,5r)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Cl)=C1 OLGUYJHINSBYSV-SFYZADRCSA-N 0.000 claims description 2
MXMWDEJGOFAQIF-ZJUUUORDSA-N (1s,5r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=CC(OC)=C1 MXMWDEJGOFAQIF-ZJUUUORDSA-N 0.000 claims description 2
TVSYLDOEQMXDNJ-ZJUUUORDSA-N (1s,5r)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C)=C1 TVSYLDOEQMXDNJ-ZJUUUORDSA-N 0.000 claims description 2
KFMJQCWVEWEXSI-BDAKNGLRSA-N (1s,5r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CC=C(Cl)N=C1 KFMJQCWVEWEXSI-BDAKNGLRSA-N 0.000 claims description 2
DOLPRZLBJYAFEQ-ZJUUUORDSA-N (1s,5r)-7-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(F)C(C)=C1 DOLPRZLBJYAFEQ-ZJUUUORDSA-N 0.000 claims description 2
LODFTIXAWYPTQJ-BDAKNGLRSA-N (1s,5r)-7-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CC=C(F)N=C1 LODFTIXAWYPTQJ-BDAKNGLRSA-N 0.000 claims description 2
UMPFGRGEHJMUQE-ZJUUUORDSA-N (1s,5r)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CC=CN=C1 UMPFGRGEHJMUQE-ZJUUUORDSA-N 0.000 claims description 2
HBMAFIWQQZYQDP-YUMQZZPRSA-N (1s,5s)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(Cl)=C1 HBMAFIWQQZYQDP-YUMQZZPRSA-N 0.000 claims description 2
XLOFKCUENYQXRD-ONGXEEELSA-N (1s,5s)-3-(5-ethynyl-6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(F)C(C#C)=C1 XLOFKCUENYQXRD-ONGXEEELSA-N 0.000 claims description 2
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239000002243 precursor Substances 0.000 description 1
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UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
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HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
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150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
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239000004334 sorbic acid Substances 0.000 description 1
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235000010356 sorbitol Nutrition 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
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WIAHCZSJMVYDJP-GHMZBOCLSA-N tert-butyl (1r,4r)-5-(5,6-dichloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=C(Cl)C(Cl)=C1 WIAHCZSJMVYDJP-GHMZBOCLSA-N 0.000 description 1
ORLLKFPKPYPAHR-CHWSQXEVSA-N tert-butyl (1r,4r)-5-(5-bromopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CC(Br)=C1 ORLLKFPKPYPAHR-CHWSQXEVSA-N 0.000 description 1
BIRODQAQVPAMHW-CHWSQXEVSA-N tert-butyl (1r,4r)-5-(5-carbamoylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CC(C(N)=O)=C1 BIRODQAQVPAMHW-CHWSQXEVSA-N 0.000 description 1
XTTDMGZROUVPBP-ZIAGYGMSSA-N tert-butyl (1r,4r)-5-(5-cyanopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CC(C#N)=C1 XTTDMGZROUVPBP-ZIAGYGMSSA-N 0.000 description 1
TYMGPBMNXUEQKW-RTBURBONSA-N tert-butyl (1r,4r)-5-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 TYMGPBMNXUEQKW-RTBURBONSA-N 0.000 description 1
NGLYDHRWXBZXPS-VXGBXAGGSA-N tert-butyl (1r,4r)-5-(6-chloro-5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=C(Cl)C(OC)=C1 NGLYDHRWXBZXPS-VXGBXAGGSA-N 0.000 description 1
BJANRKNYSGNCMJ-CHWSQXEVSA-N tert-butyl (1r,4r)-5-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=C(Cl)C(C)=C1 BJANRKNYSGNCMJ-CHWSQXEVSA-N 0.000 description 1
JELKCTPPQLXMAY-VXGBXAGGSA-N tert-butyl (1r,4r)-5-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C(Cl)N=C1 JELKCTPPQLXMAY-VXGBXAGGSA-N 0.000 description 1
DHLCVVXLOURKHC-VXGBXAGGSA-N tert-butyl (1r,4r)-5-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C(F)N=C1 DHLCVVXLOURKHC-VXGBXAGGSA-N 0.000 description 1
WUBCZFOGEDBOFL-CHWSQXEVSA-N tert-butyl (1r,4r)-5-(6-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C(OC)N=C1 WUBCZFOGEDBOFL-CHWSQXEVSA-N 0.000 description 1
WYLZZDCMUCGMGH-CHWSQXEVSA-N tert-butyl (1r,4r)-5-[6-chloro-5-(methoxymethoxy)pyridin-3-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=C(Cl)C(OCOC)=C1 WYLZZDCMUCGMGH-CHWSQXEVSA-N 0.000 description 1
MSIWYWFJAALCQM-HUUCEWRRSA-N tert-butyl (1r,4r)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@@]1(N(C(=O)OC(C)(C)C)C[C@]2(C1)[H])[H])N2CC1=CC=CC=C1 MSIWYWFJAALCQM-HUUCEWRRSA-N 0.000 description 1
SKOGGQPKZPEWEG-RYUDHWBXSA-N tert-butyl (1s,4s)-5-(4-chlorophthalazin-1-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1=CC=C2C(N3C[C@]4(N(C[C@]3([H])C4)C(=O)OC(C)(C)C)[H])=NN=C(Cl)C2=C1 SKOGGQPKZPEWEG-RYUDHWBXSA-N 0.000 description 1
XTTDMGZROUVPBP-KBPBESRZSA-N tert-butyl (1s,4s)-5-(5-cyanopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CC(C#N)=C1 XTTDMGZROUVPBP-KBPBESRZSA-N 0.000 description 1
LHGPWKXWILVVOK-RYUDHWBXSA-N tert-butyl (1s,4s)-5-(5-hydroxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CC(O)=C1 LHGPWKXWILVVOK-RYUDHWBXSA-N 0.000 description 1
TYMGPBMNXUEQKW-OALUTQOASA-N tert-butyl (1s,4s)-5-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 TYMGPBMNXUEQKW-OALUTQOASA-N 0.000 description 1
WFOOQJSIVJRJNM-UWVGGRQHSA-N tert-butyl (1s,4s)-5-(6-chloro-5-methoxycarbonylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC(C(=O)OC)=C(Cl)N=N1 WFOOQJSIVJRJNM-UWVGGRQHSA-N 0.000 description 1
JELKCTPPQLXMAY-RYUDHWBXSA-N tert-butyl (1s,4s)-5-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C(Cl)N=C1 JELKCTPPQLXMAY-RYUDHWBXSA-N 0.000 description 1
DHLCVVXLOURKHC-RYUDHWBXSA-N tert-butyl (1s,4s)-5-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C(F)N=C1 DHLCVVXLOURKHC-RYUDHWBXSA-N 0.000 description 1
RKWHXYAMXGVBMO-RYUDHWBXSA-N tert-butyl (1s,4s)-5-(6-nitropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CC=C([N+]([O-])=O)N=C1 RKWHXYAMXGVBMO-RYUDHWBXSA-N 0.000 description 1
APEYOTLPGHQCFL-QWRGUYRKSA-N tert-butyl (1s,4s)-5-pyrimidin-5-yl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)OC(C)(C)C)[H])N2C1=CN=CN=C1 APEYOTLPGHQCFL-QWRGUYRKSA-N 0.000 description 1
CFPQGWIZHGXFIP-HOTGVXAUSA-N tert-butyl (1s,4s)-5-quinolin-3-yl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1=CC=CC2=CC(N3C[C@]4(N(C[C@]3([H])C4)C(=O)OC(C)(C)C)[H])=CN=C21 CFPQGWIZHGXFIP-HOTGVXAUSA-N 0.000 description 1
OPBALOICVPTYMF-UHFFFAOYSA-N tert-butyl 3-(5-chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C2)CCC1CN2C1=CC=C(Cl)C=N1 OPBALOICVPTYMF-UHFFFAOYSA-N 0.000 description 1
MBKGDJKXYKTWSP-UHFFFAOYSA-N tert-butyl 3-(6-aminopyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C2)CCC1CN2C1=CC=C(N)N=C1 MBKGDJKXYKTWSP-UHFFFAOYSA-N 0.000 description 1
JSNNSBUDVLWJNA-UHFFFAOYSA-N tert-butyl 3-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C2)CCC1CN2C1=CC=C([N+]([O-])=O)N=C1 JSNNSBUDVLWJNA-UHFFFAOYSA-N 0.000 description 1
XQLPVDVDSOFFGO-UHFFFAOYSA-N tert-butyl 7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC2CC1CN2C1=CC=C(Cl)N=C1 XQLPVDVDSOFFGO-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
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229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920000685 trimethylsilyl polyphosphate Polymers 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
- C07D401/08—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 carbon chain containing alicyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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Organic Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
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Veterinary Medicine (AREA)
Neurosurgery (AREA)
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Psychiatry (AREA)
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Urology & Nephrology (AREA)
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Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
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Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK1069-2001A 1999-01-29 2000-01-25 Diazabicyklické deriváty, ich použitie a farmaceutický prípravok s ich obsahom SK10692001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US23983899A	1999-01-29	1999-01-29
PCT/US2000/001620 WO2000044755A1 (fr)	1999-01-29	2000-01-25	Derives diazabicycliques utiles en tant que ligands du recepteur nicotinique de l'acetylcholine

Publications (1)

Publication Number	Publication Date
SK10692001A3 true SK10692001A3 (sk)	2002-01-07

Family

ID=22903947

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1069-2001A SK10692001A3 (sk)	1999-01-29	2000-01-25	Diazabicyklické deriváty, ich použitie a farmaceutický prípravok s ich obsahom

Country Status (26)

Country	Link
EP (2)	EP1147112B1 (fr)
JP (1)	JP4676062B2 (fr)
KR (1)	KR20010101725A (fr)
CN (2)	CN1345320A (fr)
AR (1)	AR034538A1 (fr)
AT (2)	ATE253067T1 (fr)
AU (1)	AU773795B2 (fr)
BG (1)	BG105836A (fr)
BR (1)	BR0007664A (fr)
CA (1)	CA2361525C (fr)
CO (1)	CO5150231A1 (fr)
CZ (1)	CZ20012716A3 (fr)
DE (2)	DE60038823D1 (fr)
DK (1)	DK1147112T3 (fr)
ES (2)	ES2305373T3 (fr)
HK (1)	HK1043116B (fr)
HU (1)	HUP0200332A3 (fr)
IL (1)	IL144340A0 (fr)
NO (1)	NO20013731L (fr)
NZ (1)	NZ512884A (fr)
PT (1)	PT1147112E (fr)
SK (1)	SK10692001A3 (fr)
TR (1)	TR200102162T2 (fr)
TW (1)	TW200300021A (fr)
WO (1)	WO2000044755A1 (fr)
ZA (1)	ZA200105835B (fr)

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2000
- 2000-01-25 EP EP00906998A patent/EP1147112B1/fr not_active Expired - Lifetime
- 2000-01-25 HU HU0200332A patent/HUP0200332A3/hu unknown
- 2000-01-25 DE DE60038823T patent/DE60038823D1/de not_active Expired - Lifetime
- 2000-01-25 SK SK1069-2001A patent/SK10692001A3/sk unknown
- 2000-01-25 WO PCT/US2000/001620 patent/WO2000044755A1/fr not_active Ceased
- 2000-01-25 HK HK02102948.7A patent/HK1043116B/en not_active IP Right Cessation
- 2000-01-25 ES ES03017562T patent/ES2305373T3/es not_active Expired - Lifetime
- 2000-01-25 CN CN00805544A patent/CN1345320A/zh active Pending
- 2000-01-25 ES ES00906998T patent/ES2209825T3/es not_active Expired - Lifetime
- 2000-01-25 BR BR0007664-3A patent/BR0007664A/pt not_active IP Right Cessation
- 2000-01-25 IL IL14434000A patent/IL144340A0/xx unknown
- 2000-01-25 PT PT00906998T patent/PT1147112E/pt unknown
- 2000-01-25 CZ CZ20012716A patent/CZ20012716A3/cs unknown
- 2000-01-25 AT AT00906998T patent/ATE253067T1/de active
- 2000-01-25 EP EP03017562A patent/EP1359152B1/fr not_active Expired - Lifetime
- 2000-01-25 AT AT03017562T patent/ATE394401T1/de not_active IP Right Cessation
- 2000-01-25 JP JP2000596011A patent/JP4676062B2/ja not_active Expired - Fee Related
- 2000-01-25 CN CNA2004100974823A patent/CN1636996A/zh active Pending
- 2000-01-25 AU AU28569/00A patent/AU773795B2/en not_active Ceased
- 2000-01-25 DE DE60006213T patent/DE60006213T2/de not_active Expired - Lifetime
- 2000-01-25 KR KR1020017009420A patent/KR20010101725A/ko not_active Ceased
- 2000-01-25 CA CA002361525A patent/CA2361525C/fr not_active Expired - Fee Related
- 2000-01-25 DK DK00906998T patent/DK1147112T3/da active
- 2000-01-25 NZ NZ512884A patent/NZ512884A/xx unknown
- 2000-01-25 TR TR2001/02162T patent/TR200102162T2/xx unknown
- 2000-01-26 CO CO00004294A patent/CO5150231A1/es unknown
- 2000-01-28 AR ARP000100393A patent/AR034538A1/es not_active Application Discontinuation
- 2000-03-01 TW TW091133012A patent/TW200300021A/zh unknown
2001
- 2001-07-16 ZA ZA200105835A patent/ZA200105835B/en unknown
- 2001-07-30 NO NO20013731A patent/NO20013731L/no not_active Application Discontinuation
- 2001-08-22 BG BG105836A patent/BG105836A/xx unknown

Also Published As

Publication number	Publication date
NZ512884A (en)	2004-03-26
ES2209825T3 (es)	2004-07-01
WO2000044755A1 (fr)	2000-08-03
TR200102162T2 (tr)	2001-12-21
HK1043116B (en)	2004-10-15
EP1359152B1 (fr)	2008-05-07
PT1147112E (pt)	2004-03-31
ATE394401T1 (de)	2008-05-15
TW200300021A (en)	2003-05-01
DE60006213T2 (de)	2004-07-29
CN1636996A (zh)	2005-07-13
CZ20012716A3 (cs)	2001-11-14
DK1147112T3 (da)	2004-02-23
CO5150231A1 (es)	2002-04-29
CN1345320A (zh)	2002-04-17
DE60006213D1 (de)	2003-12-04
JP4676062B2 (ja)	2011-04-27
EP1359152A3 (fr)	2003-12-17
EP1147112B1 (fr)	2003-10-29
CA2361525A1 (fr)	2000-08-03
EP1359152A2 (fr)	2003-11-05
DE60038823D1 (de)	2008-06-19
AR034538A1 (es)	2004-03-03
AU2856900A (en)	2000-08-18
EP1147112A1 (fr)	2001-10-24
AU773795B2 (en)	2004-06-03
ATE253067T1 (de)	2003-11-15
NO20013731L (no)	2001-09-18
JP2002535409A (ja)	2002-10-22
KR20010101725A (ko)	2001-11-14
ZA200105835B (en)	2002-10-16
CA2361525C (fr)	2009-12-08
IL144340A0 (en)	2002-05-23
ES2305373T3 (es)	2008-11-01
BR0007664A (pt)	2002-05-07
NO20013731D0 (no)	2001-07-30
HK1043116A1 (en)	2002-09-06
HUP0200332A3 (en)	2002-09-30
BG105836A (en)	2002-03-29
HUP0200332A2 (en)	2002-06-29

Publication	Publication Date	Title
EP1147112B1 (fr)	2003-10-29	Derives diazabicycliques utiles en tant que ligands du recepteur nicotinique de l'acetylcholine
US7265115B2 (en)	2007-09-04	Diazabicyclic CNS active agents
EP3728221B1 (fr)	2022-06-01	Composés d'indole à substitution amide utiles en tant qu'inhibiteurs de tlr
US8119635B2 (en)	2012-02-21	Diazabicyclic central nervous system active agents
AU2001266559C1 (en)	2005-11-17	Diazabicyclic central nervous system active agents
AU2001266559A1 (en)	2002-01-24	Diazabicyclic central nervous system active agents
EP3679039B1 (fr)	2021-06-16	Dérivés d'analogues de tyrosine en tant qu'inhibiteurs de rho-kinase
MXPA01007660A (en)	2002-05-09	Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands
EP1257535B1 (fr)	2007-05-23	Composes pyridine substitues utiles dans la regulation de la transmission synaptique chimique