NO323631B1 - Triazaspiro[5,5]undekan-derivater, og farmasoytiske preparater, kjemokiner/kjemolinregulatorer, og midler for forebygging og/eller behandling omfattende slike som en aktiv bestanddel. - Google Patents

Info

Publication number

NO323631B1

NO323631B1 NO20022609A NO20022609A NO323631B1 NO 323631 B1 NO323631 B1 NO 323631B1 NO 20022609 A NO20022609 A NO 20022609A NO 20022609 A NO20022609 A NO 20022609A NO 323631 B1 NO323631 B1 NO 323631B1

Authority

NO

Norway

Prior art keywords

dioxo

triazaspiro

undecane

butyl

methylpropyl

Prior art date

1999-12-03

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• 102000019034 Chemokines Human genes 0.000 title claims abstract description 18
• 108010012236 Chemokines Proteins 0.000 title claims abstract description 18
• 239000004480 active ingredient Substances 0.000 title claims abstract description 11
• 230000002265 prevention Effects 0.000 title claims abstract description 9
• RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical class CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 title claims description 13
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
• 239000003795 chemical substances by application Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 320
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 23
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 21
• 231100000252 nontoxic Toxicity 0.000 claims abstract description 16
• 230000003000 nontoxic effect Effects 0.000 claims abstract description 16
• 208000024780 Urticaria Diseases 0.000 claims abstract description 8
• 208000006454 hepatitis Diseases 0.000 claims abstract description 6
• 231100000283 hepatitis Toxicity 0.000 claims abstract description 6
• 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 5
• 206010003246 arthritis Diseases 0.000 claims abstract description 5
• 208000006673 asthma Diseases 0.000 claims abstract description 5
• 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 5
• 208000017169 kidney disease Diseases 0.000 claims abstract description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
• 201000008383 nephritis Diseases 0.000 claims abstract description 4
• RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 261
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 149
• -1 C2-8 alkynyl ether Chemical compound 0.000 claims description 149
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 69
• 125000002947 alkylene group Chemical group 0.000 claims description 66
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 65
• 239000001257 hydrogen Substances 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 150000002431 hydrogen Chemical group 0.000 claims description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• 125000000304 alkynyl group Chemical group 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 229930194542 Keto Natural products 0.000 claims description 19
• 125000000468 ketone group Chemical group 0.000 claims description 19
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
• 125000004434 sulfur atom Chemical group 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000003003 spiro group Chemical group 0.000 claims description 13
• LTEQKOJTJCNSKO-UHFFFAOYSA-N 1,4,9-triazaspiro[5.5]undecane Chemical compound C1NCCNC11CCNCC1 LTEQKOJTJCNSKO-UHFFFAOYSA-N 0.000 claims description 11
• 150000002825 nitriles Chemical class 0.000 claims description 11
• 101100371682 Caenorhabditis elegans cyk-3 gene Proteins 0.000 claims description 10
• 208000030507 AIDS Diseases 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 206010006474 Bronchopulmonary aspergillosis allergic Diseases 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 206010010741 Conjunctivitis Diseases 0.000 claims description 4
• 206010062016 Immunosuppression Diseases 0.000 claims description 4
• 206010027476 Metastases Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 208000006778 allergic bronchopulmonary aspergillosis Diseases 0.000 claims description 4
• 230000000172 allergic effect Effects 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims description 4
• 230000001506 immunosuppresive effect Effects 0.000 claims description 4
• 230000009401 metastasis Effects 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 201000004193 respiratory failure Diseases 0.000 claims description 4
• 206010039083 rhinitis Diseases 0.000 claims description 4
• 230000035939 shock Effects 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 208000034486 Multi-organ failure Diseases 0.000 claims description 3
• 208000010718 Multiple Organ Failure Diseases 0.000 claims description 3
• 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 231100000433 cytotoxic Toxicity 0.000 claims description 3
• 230000001472 cytotoxic effect Effects 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• NECLQTPQJZSWOE-UHFFFAOYSA-N spiro[5.5]undecane Chemical compound C1CCCCC21CCCCC2 NECLQTPQJZSWOE-UHFFFAOYSA-N 0.000 claims description 3
• VBONNDPACFTZMX-HSZRJFAPSA-N (3r)-1-butyl-3-(cyclohexylmethyl)-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@@H]1C(=O)N(C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 VBONNDPACFTZMX-HSZRJFAPSA-N 0.000 claims description 2
• WUTCDIFLPLKLBC-FTJBHMTQSA-N (3r)-1-butyl-3-[(1s)-1-hydroxy-2-methylpropyl]-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@@H]([C@@H](O)C(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 WUTCDIFLPLKLBC-FTJBHMTQSA-N 0.000 claims description 2
• FVSCJQKRVWEZKP-XMMPIXPASA-N (3r)-3-(2-methylpropyl)-9-(6-phenylhexyl)-1-propyl-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCN1C(=O)[C@@H](CC(C)C)NC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 FVSCJQKRVWEZKP-XMMPIXPASA-N 0.000 claims description 2
• WRWCPJANFGOLPT-QHCPKHFHSA-N (3s)-1-(1-benzylpiperidin-4-yl)-3-methyl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1C2CCN(CC=3C=CC=CC=3)CC2)=O)C)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WRWCPJANFGOLPT-QHCPKHFHSA-N 0.000 claims description 2
• NHPOHQBGNYOWRZ-VWLOTQADSA-N (3s)-1-(2,2-diphenylpropyl)-3-methyl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC(C)(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)C)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 NHPOHQBGNYOWRZ-VWLOTQADSA-N 0.000 claims description 2
• JIHNEDYGHOIIEJ-VWLOTQADSA-N (3s)-1-butyl-3-(2-methylpropyl)-9-[(6-phenylpyridin-3-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 JIHNEDYGHOIIEJ-VWLOTQADSA-N 0.000 claims description 2
• KTRPCOLXGDMJKK-QHCPKHFHSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(2-hydroxy-3-methylphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=C(C)C=CC=3)O)CC2)C(=O)N1)CCCC)C1CCCCC1 KTRPCOLXGDMJKK-QHCPKHFHSA-N 0.000 claims description 2
• DEOHZTPTSDUBQI-DEOSSOPVSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(4-methylphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(C)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 DEOHZTPTSDUBQI-DEOSSOPVSA-N 0.000 claims description 2
• YCQGIWBDSOHGDH-NDEPHWFRSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(6-phenylpyridin-3-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=NC(=CC=3)C=3C=CC=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 YCQGIWBDSOHGDH-NDEPHWFRSA-N 0.000 claims description 2
• SSWLOJLVKLZDJX-LJAQVGFWSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[3-(3-hydroxyphenyl)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(C=CC=3)C=3C=C(O)C=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 SSWLOJLVKLZDJX-LJAQVGFWSA-N 0.000 claims description 2
• BDYPCUNTCPDADW-LJAQVGFWSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[3-(4-hydroxyphenyl)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(C=CC=3)C=3C=CC(O)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 BDYPCUNTCPDADW-LJAQVGFWSA-N 0.000 claims description 2
• YGKUWFNPRSRENZ-LJAQVGFWSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[4-(4-hydroxyphenoxy)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(O)=CC=4)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 YGKUWFNPRSRENZ-LJAQVGFWSA-N 0.000 claims description 2
• YZRFXVQCBQMVFL-PMERELPUSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[4-(4-methylphenoxy)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(C)=CC=4)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 YZRFXVQCBQMVFL-PMERELPUSA-N 0.000 claims description 2
• MSMXSKDVXBFVFB-JTQLQIEISA-N (3s)-1-butyl-3-(hydroxymethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CO)NC(=O)C11CCNCC1 MSMXSKDVXBFVFB-JTQLQIEISA-N 0.000 claims description 2
• YPFNYSLAHVDJGM-QHCPKHFHSA-N (3s)-1-butyl-9-[(2-chlorophenyl)methyl]-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC=CC=3)Cl)CC2)C(=O)N1)CCCC)C1CCCCC1 YPFNYSLAHVDJGM-QHCPKHFHSA-N 0.000 claims description 2
• VGGUIIOFXSIAFS-FQEVSTJZSA-N (3s)-1-butyl-9-[(3-chlorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(Cl)C=CC=2)CC1 VGGUIIOFXSIAFS-FQEVSTJZSA-N 0.000 claims description 2
• XAWNQLOPNKISCC-QHCPKHFHSA-N (3s)-1-butyl-9-[(3-chlorophenyl)methyl]-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(Cl)C=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 XAWNQLOPNKISCC-QHCPKHFHSA-N 0.000 claims description 2
• LPFQTMIVVWNXNL-NRFANRHFSA-N (3s)-1-butyl-9-[(3-methylphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(C)C=CC=2)CC1 LPFQTMIVVWNXNL-NRFANRHFSA-N 0.000 claims description 2
• HNAPWKSIQZJRDW-QHCPKHFHSA-N (3s)-1-butyl-9-[(4-chlorophenyl)methyl]-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(Cl)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 HNAPWKSIQZJRDW-QHCPKHFHSA-N 0.000 claims description 2
• FLHXODPVFRNLDL-MHZLTWQESA-N (3s)-1-butyl-9-[[3,5-dimethyl-1-(2-phenylethyl)pyrazol-4-yl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC2=C(N(CCC=3C=CC=CC=3)N=C2C)C)CC1 FLHXODPVFRNLDL-MHZLTWQESA-N 0.000 claims description 2
• PLZFVQWVSWFGKJ-LJAQVGFWSA-N (3s)-1-butyl-9-[[4-(4-chlorophenoxy)phenyl]methyl]-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(Cl)=CC=4)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 PLZFVQWVSWFGKJ-LJAQVGFWSA-N 0.000 claims description 2
• RDJNTFQZSJVPFQ-DEOSSOPVSA-N (3s)-1-butyl-9-[[4-(diethylamino)phenyl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(=CC=2)N(CC)CC)CC1 RDJNTFQZSJVPFQ-DEOSSOPVSA-N 0.000 claims description 2
• FRPPPXARQWAGIP-VWLOTQADSA-N (3s)-1-butyl-9-[[6-(4-methoxyphenoxy)pyridin-3-yl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=NC(OC=3C=CC(OC)=CC=3)=CC=2)CC1 FRPPPXARQWAGIP-VWLOTQADSA-N 0.000 claims description 2
• GSMOINFTZFVFOJ-NVQXNPDNSA-N (3s)-3-[(2s)-butan-2-yl]-1-butyl-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H]([C@@H](C)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 GSMOINFTZFVFOJ-NVQXNPDNSA-N 0.000 claims description 2
• NQCMADUECAMHGF-GEVKEYJPSA-N (3s)-3-benzyl-1-(oxolan-2-ylmethyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@@H]1NC(C2(CCN(CCCCC=3C=CC=CC=3)CC2)N(CC2OCCC2)C1=O)=O)C1=CC=CC=C1 NQCMADUECAMHGF-GEVKEYJPSA-N 0.000 claims description 2
• PWCCTZLOECUIDD-KRWDZBQOSA-N (3s)-3-methyl-1-(2-methylpropyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CC(C)CN1C(=O)[C@H](C)NC(=O)C11CCN(CCC=2C=CC=CC=2)CC1 PWCCTZLOECUIDD-KRWDZBQOSA-N 0.000 claims description 2
• LDNFTCQRIVUIBF-PMERELPUSA-N (3s)-9-(2-phenylethyl)-3-[(4-phenylmethoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)C(C=C1)=CC=C1OCC1=CC=CC=C1 LDNFTCQRIVUIBF-PMERELPUSA-N 0.000 claims description 2
• CVLKGPWNXVTSGG-SANMLTNESA-N (3s)-9-[[4-(benzenesulfonyl)phenyl]methyl]-1-butyl-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)CC1 CVLKGPWNXVTSGG-SANMLTNESA-N 0.000 claims description 2
• AEGHKDWRCKLKHO-UHFFFAOYSA-N 1-(3-hydroxypropyl)-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound OCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 AEGHKDWRCKLKHO-UHFFFAOYSA-N 0.000 claims description 2
• AVMCSGYSWBCLSH-UHFFFAOYSA-N 1-(3-methylbut-2-enyl)-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CC(C)=CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 AVMCSGYSWBCLSH-UHFFFAOYSA-N 0.000 claims description 2
• MGCWSVKKXDNIDZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C1CC1CN1C(=O)C(CC(C)C)NC(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=CC=C1 MGCWSVKKXDNIDZ-UHFFFAOYSA-N 0.000 claims description 2
• DWZQMFUERYCBDJ-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C=1C=COC=1CN1C(=O)C(CC(C)C)NC(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=CC=C1 DWZQMFUERYCBDJ-UHFFFAOYSA-N 0.000 claims description 2
• WCESRFMOCKYSEK-UHFFFAOYSA-N 1-but-2-ynyl-9-[[3,5-dimethyl-1-(4-methylphenyl)pyrazol-4-yl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CC#CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC2=C(N(N=C2C)C=2C=CC(C)=CC=2)C)CC1 WCESRFMOCKYSEK-UHFFFAOYSA-N 0.000 claims description 2
• DDEYRKLZYLDCIL-UHFFFAOYSA-N 1-butan-2-yl-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCC(C)N1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 DDEYRKLZYLDCIL-UHFFFAOYSA-N 0.000 claims description 2
• FDWPPSXZXOZKJQ-UHFFFAOYSA-N 1-butyl-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 FDWPPSXZXOZKJQ-UHFFFAOYSA-N 0.000 claims description 2
• QBYHGOQUKOCQEQ-UHFFFAOYSA-N 1-butyl-3-(2-methylpropyl)-9-(quinolin-3-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=C3C=CC=CC3=NC=2)CC1 QBYHGOQUKOCQEQ-UHFFFAOYSA-N 0.000 claims description 2
• SFLOJTAZVAQQDZ-UHFFFAOYSA-N 1-butyl-3-(2-methylpropyl)-9-[(6-phenoxypyridin-3-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=NC(OC=3C=CC=CC=3)=CC=2)CC1 SFLOJTAZVAQQDZ-UHFFFAOYSA-N 0.000 claims description 2
• NCGCEFVGXJNEQV-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCNCC2)N(CCCC)C(=O)C1CC1CCCCC1 NCGCEFVGXJNEQV-UHFFFAOYSA-N 0.000 claims description 2
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