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

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

Info

Publication number: NO323631B1
Authority: NO; Norway
Prior art keywords: dioxo; triazaspiro; undecane; butyl; methylpropyl
Prior art date: 1999-12-03

Application number

NO20022609A

Other languages

English (en)

Norwegian (no)

Other versions

NO20022609D0 (no

NO20022609L (no

Inventor

Hiromu Habashita

Shin-Ichi Hamano

Shiro Shibayama

Yoshikazu Takaoka

Original Assignee

Ono Pharmaceutical Co

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.)

1999-12-03

Filing date

2002-05-31

Publication date

2007-06-18

2002-05-31 Application filed by Ono Pharmaceutical Co filed Critical Ono Pharmaceutical Co

2002-05-31 Publication of NO20022609D0 publication Critical patent/NO20022609D0/no

2002-07-26 Publication of NO20022609L publication Critical patent/NO20022609L/no

2007-06-18 Publication of NO323631B1 publication Critical patent/NO323631B1/no

Links

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
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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
ODQZDIKXBXEYOO-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2-phenyl-1h-imidazol-5-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3NC(=NC=3)C=3C=CC=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ODQZDIKXBXEYOO-UHFFFAOYSA-N 0.000 claims description 2
IRWPEABHINEXFW-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(3,4-dimethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=C(OC)C(OC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 IRWPEABHINEXFW-UHFFFAOYSA-N 0.000 claims description 2
UBOSWZVKFNAYOS-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 UBOSWZVKFNAYOS-UHFFFAOYSA-N 0.000 claims description 2
YAEPUPIVZQILCP-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(5-ethylthiophen-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3SC(CC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 YAEPUPIVZQILCP-UHFFFAOYSA-N 0.000 claims description 2
PTJMXFLRZJVVHX-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC2)C(C)C=2C=C3OCCOC3=CC=2)N(CCCC)C(=O)C1CC1CCCCC1 PTJMXFLRZJVVHX-UHFFFAOYSA-N 0.000 claims description 2
HFXCPZXIGUXAEM-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[2-(3,5-dimethylpyrazol-1-yl)-5-methoxyphenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C(=CC=C(OC)C=3)N3C(=CC(C)=N3)C)CC2)N(CCCC)C(=O)C1CC1CCCCC1 HFXCPZXIGUXAEM-UHFFFAOYSA-N 0.000 claims description 2
OILBLOLJOLCDQR-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[4-(cyclopropylmethoxy)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=CC(OCC4CC4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 OILBLOLJOLCDQR-UHFFFAOYSA-N 0.000 claims description 2
PUUZAYCRMRYUIN-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=CC(OCCN(CC)CC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 PUUZAYCRMRYUIN-UHFFFAOYSA-N 0.000 claims description 2
NHADAFJYRWVCKO-UHFFFAOYSA-N 1-butyl-3-(methoxymethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(COC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 NHADAFJYRWVCKO-UHFFFAOYSA-N 0.000 claims description 2
YPYUTRLABHTLAX-UHFFFAOYSA-N 1-butyl-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-3-(1-hydroxy-2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(C(O)C(C)C)NC(=O)C11CCN(CC=2C=C3OCCOC3=CC=2)CC1 YPYUTRLABHTLAX-UHFFFAOYSA-N 0.000 claims description 2
TUTOIHPXRNNRCU-UHFFFAOYSA-N 1-butyl-9-[(3,5-diethyl-1-phenylpyrazol-4-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC2=C(N(N=C2CC)C=2C=CC=CC=2)CC)CC1 TUTOIHPXRNNRCU-UHFFFAOYSA-N 0.000 claims description 2
DEJWMEAHNHYCLF-UHFFFAOYSA-N 1-butyl-9-[[4-(5-chloropyridin-3-yl)oxyphenyl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=C(Cl)C=NC=3)=CC=2)CC1 DEJWMEAHNHYCLF-UHFFFAOYSA-N 0.000 claims description 2
NXPBKOJNUJKHKZ-UHFFFAOYSA-N 1-butyl-9-[[4-(n-methylanilino)phenyl]methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(=CC=2)N(C)C=2C=CC=CC=2)CC1 NXPBKOJNUJKHKZ-UHFFFAOYSA-N 0.000 claims description 2
NQOJHQIHYAHLLT-UHFFFAOYSA-N 3-(2-methylpropyl)-1-pentan-2-yl-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCC(C)N1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 NQOJHQIHYAHLLT-UHFFFAOYSA-N 0.000 claims description 2
YCWLDZPOFYKSQQ-UHFFFAOYSA-N 3-(2-methylpropyl)-1-propyl-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCN1C(=O)C(CC(C)C)NC(=O)C11CCNCC1 YCWLDZPOFYKSQQ-UHFFFAOYSA-N 0.000 claims description 2
KDGATIRWGALNCZ-VWLOTQADSA-N 3-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenyl]prop-2-ynoic acid Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(=CC=3)C#CC(O)=O)CC2)C(=O)N1)CCCC)C1CCCCC1 KDGATIRWGALNCZ-VWLOTQADSA-N 0.000 claims description 2
PBIKPCFIWGABNN-VWLOTQADSA-N 3-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenyl]propanoic acid Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(CCC(O)=O)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 PBIKPCFIWGABNN-VWLOTQADSA-N 0.000 claims description 2
FCLRKRZPOKPVIN-LJAQVGFWSA-N 4-[3-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenyl]benzoic acid Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(C=CC=3)C=3C=CC(=CC=3)C(O)=O)CC2)C(=O)N1)CCCC)C1CCCCC1 FCLRKRZPOKPVIN-LJAQVGFWSA-N 0.000 claims description 2
JKCXVFWYJVJLLD-VWLOTQADSA-N 4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-n,n-dimethylbenzamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(=CC=3)C(=O)N(C)C)CC2)C(=O)N1)CCCC)C1CCCCC1 JKCXVFWYJVJLLD-VWLOTQADSA-N 0.000 claims description 2
LJCLUESDEKOVSR-UHFFFAOYSA-N 9-[(5-benzylthiophen-2-yl)methyl]-1-butyl-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2SC(CC=3C=CC=CC=3)=CC=2)CC1 LJCLUESDEKOVSR-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
VRQRDIOIQMPNBX-DEOSSOPVSA-N benzyl (3s)-1-butyl-2,5-dioxo-3-(phenylmethoxymethyl)-1,4,9-triazaspiro[5.5]undecane-9-carboxylate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)OCC=2C=CC=CC=2)C(=O)N1)CCCC)OCC1=CC=CC=C1 VRQRDIOIQMPNBX-DEOSSOPVSA-N 0.000 claims description 2
VTDDAUFGQOHYHY-QHCPKHFHSA-N benzyl (3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecane-9-carboxylate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)OCC=2C=CC=CC=2)C(=O)N1)CCCC)C1CCCCC1 VTDDAUFGQOHYHY-QHCPKHFHSA-N 0.000 claims description 2
ZHAFDOOWYANPSF-KRWDZBQOSA-N benzyl (3s)-1-butyl-3-(hydroxymethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecane-9-carboxylate Chemical compound CCCCN1C(=O)[C@H](CO)NC(=O)C11CCN(C(=O)OCC=2C=CC=CC=2)CC1 ZHAFDOOWYANPSF-KRWDZBQOSA-N 0.000 claims description 2
VOTLOSHWWAQODX-UHFFFAOYSA-N benzyl 2-[1-butyl-2,5-dioxo-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]acetate Chemical compound N1C(=O)C2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC(=O)OCC1=CC=CC=C1 VOTLOSHWWAQODX-UHFFFAOYSA-N 0.000 claims description 2
HLWDTCPLWPCZLE-SANMLTNESA-N n-[4-[4-[[(3s)-1-butyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]phenyl]methanesulfonamide Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC2=C(N(N=C2C)C=2C=CC(NS(C)(=O)=O)=CC=2)C)CC1 HLWDTCPLWPCZLE-SANMLTNESA-N 0.000 claims description 2
GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims 3
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 3
229960003260 chlorhexidine Drugs 0.000 claims 3
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
229940055764 triaz Drugs 0.000 claims 2
FSVGBMSJFXJJMV-OLZOCXBDSA-N (3r)-1-butyl-3-[(1s)-1-hydroxy-2-methylpropyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@@H]([C@@H](O)C(C)C)NC(=O)C11CCNCC1 FSVGBMSJFXJJMV-OLZOCXBDSA-N 0.000 claims 1
KAFYBJYMKPGXAI-JWQCQUIFSA-N (3r)-1-butyl-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-3-[(1r)-1-hydroxy-2-methylpropyl]-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(CC2=C(N(N=C2C)C=2C=CC=CC=2)C)CC1 KAFYBJYMKPGXAI-JWQCQUIFSA-N 0.000 claims 1
CLFBKPFKGONWCE-XMMPIXPASA-N (3r)-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-3-(2-methylpropyl)-1-propyl-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCN1C(=O)[C@@H](CC(C)C)NC(=O)C11CCN(CC2=C(N(N=C2C)C=2C=CC=CC=2)C)CC1 CLFBKPFKGONWCE-XMMPIXPASA-N 0.000 claims 1
NCGCEFVGXJNEQV-INIZCTEOSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCNCC2)C(=O)N1)CCCC)C1CCCCC1 NCGCEFVGXJNEQV-INIZCTEOSA-N 0.000 claims 1
FHQCYVSVOVPPNO-LJAQVGFWSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(3,5-dimethyl-1-quinoxalin-2-ylpyrazol-4-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3N=C4C=CC=CC4=NC=3)C)CC2)C(=O)N1)CCCC)C1CCCCC1 FHQCYVSVOVPPNO-LJAQVGFWSA-N 0.000 claims 1
KTPIZPPUCHNCKW-QHCPKHFHSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(3-fluorophenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(F)C=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 KTPIZPPUCHNCKW-QHCPKHFHSA-N 0.000 claims 1
YCLWGRBSXGLEJN-DEOSSOPVSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[(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)CC2)C(=O)N1)CCCC)C1CCCCC1 YCLWGRBSXGLEJN-DEOSSOPVSA-N 0.000 claims 1
YXHWELTWEHEVTE-PMERELPUSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[3,5-dimethyl-1-(2-phenylethyl)pyrazol-4-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(CCC=4C=CC=CC=4)N=C3C)C)CC2)C(=O)N1)CCCC)C1CCCCC1 YXHWELTWEHEVTE-PMERELPUSA-N 0.000 claims 1
NGQTZTXNYTXUIW-NDEPHWFRSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-[[4-(morpholin-4-ylmethyl)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(CN4CCOCC4)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 NGQTZTXNYTXUIW-NDEPHWFRSA-N 0.000 claims 1
FSVGBMSJFXJJMV-QWHCGFSZSA-N (3s)-1-butyl-3-[(1r)-1-hydroxy-2-methylpropyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)[C@H]([C@H](O)C(C)C)NC(=O)C11CCNCC1 FSVGBMSJFXJJMV-QWHCGFSZSA-N 0.000 claims 1
NVBNCJDGRXTOAL-DEOSSOPVSA-N (3s)-1-butyl-9-(cyclohexylmethyl)-3-[(4-methoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3CCCCC3)CC2)C(=O)N1)CCCC)C1=CC=C(OC)C=C1 NVBNCJDGRXTOAL-DEOSSOPVSA-N 0.000 claims 1
TXIURQMPBQNXSV-VWLOTQADSA-N (3s)-1-butyl-9-[(1-cyclohexyl-3,5-dimethylpyrazol-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(C3CCCCC3)N=C2C)C)CC1 TXIURQMPBQNXSV-VWLOTQADSA-N 0.000 claims 1
KAFYBJYMKPGXAI-DQEYMECFSA-N (3s)-1-butyl-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-3-[(1s)-1-hydroxy-2-methylpropyl]-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(CC2=C(N(N=C2C)C=2C=CC=CC=2)C)CC1 KAFYBJYMKPGXAI-DQEYMECFSA-N 0.000 claims 1
BVDYSGUAVVIAEW-FQEVSTJZSA-N (3s)-1-butyl-9-[(3-fluorophenyl)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(F)C=CC=2)CC1 BVDYSGUAVVIAEW-FQEVSTJZSA-N 0.000 claims 1
YHAYQWQTENJXIY-DEOSSOPVSA-N (3s)-1-butyl-9-[(4-butylphenyl)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(CCCC)=CC=2)CC1 YHAYQWQTENJXIY-DEOSSOPVSA-N 0.000 claims 1
UVMLVHRPGOCRKL-FQEVSTJZSA-N (3s)-1-butyl-9-[(4-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=CC(Cl)=CC=2)CC1 UVMLVHRPGOCRKL-FQEVSTJZSA-N 0.000 claims 1
HDZKUXIRHPNYRJ-FQEVSTJZSA-N (3s)-1-butyl-9-[(4-fluorophenyl)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(F)=CC=2)CC1 HDZKUXIRHPNYRJ-FQEVSTJZSA-N 0.000 claims 1
VGTQHVIIMHKNLI-QHCPKHFHSA-N (3s)-1-butyl-9-[(5-chloro-3-methyl-1-phenylpyrazol-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(N=C2C)C=2C=CC=CC=2)Cl)CC1 VGTQHVIIMHKNLI-QHCPKHFHSA-N 0.000 claims 1
URGMLDVSPNMODE-IBGZPJMESA-N (3s)-1-butyl-9-[(7-methoxy-1,3-benzodioxol-5-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=C(OC)C=3OCOC=3C=2)CC1 URGMLDVSPNMODE-IBGZPJMESA-N 0.000 claims 1
BUXVWPXZQXORFB-QFIPXVFZSA-N (3s)-1-butyl-9-[[4-(2-hydroxyethoxy)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(OCCO)=CC=2)CC1 BUXVWPXZQXORFB-QFIPXVFZSA-N 0.000 claims 1
AKOKQBGEHDQCCF-MHZLTWQESA-N (3s)-1-butyl-9-[[4-(4-methoxyphenoxy)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(OC=3C=CC(OC)=CC=3)=CC=2)CC1 AKOKQBGEHDQCCF-MHZLTWQESA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Dermatology (AREA)
Oncology (AREA)
Urology & Nephrology (AREA)
Rheumatology (AREA)
Emergency Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Communicable Diseases (AREA)
Transplantation (AREA)
Physical Education & Sports Medicine (AREA)
Gastroenterology & Hepatology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20022609A 1999-12-03 2002-05-31 Triazaspiro[5,5]undekan-derivater, og farmasoytiske preparater, kjemokiner/kjemolinregulatorer, og midler for forebygging og/eller behandling omfattende slike som en aktiv bestanddel. NO323631B1 (no)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP34496799		1999-12-03
JP2000018673		2000-01-27
JP2000027968		2000-02-04
JP2000147882		2000-05-19
PCT/JP2000/008517 WO2001040227A1 (en)	1999-12-03	2000-12-01	Triazaspiro[5.5]undecane derivatives and drugs containing the same as the active ingredient

Publications (3)

Publication Number	Publication Date
NO20022609D0 NO20022609D0 (no)	2002-05-31
NO20022609L NO20022609L (no)	2002-07-26
NO323631B1 true NO323631B1 (no)	2007-06-18

Family

ID=27480653

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20022609A NO323631B1 (no)	1999-12-03	2002-05-31	Triazaspiro[5,5]undekan-derivater, og farmasoytiske preparater, kjemokiner/kjemolinregulatorer, og midler for forebygging og/eller behandling omfattende slike som en aktiv bestanddel.

Country Status (18)

Country	Link
US (1)	US7119091B2 (pt)
EP (1)	EP1236726B1 (pt)
JP (1)	JP4721087B2 (pt)
KR (1)	KR100613176B1 (pt)
CN (1)	CN1246321C (pt)
AT (1)	ATE283854T1 (pt)
AU (1)	AU780419C (pt)
BR (1)	BR0016111A (pt)
CA (1)	CA2394679A1 (pt)
DE (1)	DE60016454T2 (pt)
ES (1)	ES2233479T3 (pt)
HU (1)	HUP0300641A2 (pt)
MX (1)	MXPA02005465A (pt)
NO (1)	NO323631B1 (pt)
NZ (1)	NZ519183A (pt)
PT (1)	PT1236726E (pt)
TW (1)	TWI224597B (pt)
WO (1)	WO2001040227A1 (pt)

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KR20070050076A (ko) *	2004-08-10	2007-05-14	인사이트 산 디에고 인코포레이티드	아미도 화합물 및 약제로서의 이의 용도
NZ553696A (en)	2004-09-13	2010-02-26	Ono Pharmaceutical Co	Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient
US8110581B2 (en)	2004-11-10	2012-02-07	Incyte Corporation	Lactam compounds and their use as pharmaceuticals
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2000
- 2000-12-01 PT PT00979050T patent/PT1236726E/pt unknown
- 2000-12-01 CA CA002394679A patent/CA2394679A1/en not_active Abandoned
- 2000-12-01 KR KR1020027007117A patent/KR100613176B1/ko not_active Expired - Fee Related
- 2000-12-01 MX MXPA02005465A patent/MXPA02005465A/es active IP Right Grant
- 2000-12-01 ES ES00979050T patent/ES2233479T3/es not_active Expired - Lifetime
- 2000-12-01 NZ NZ519183A patent/NZ519183A/xx unknown
- 2000-12-01 HU HU0300641A patent/HUP0300641A2/hu unknown
- 2000-12-01 US US10/148,382 patent/US7119091B2/en not_active Expired - Fee Related
- 2000-12-01 CN CNB008187703A patent/CN1246321C/zh not_active Expired - Fee Related
- 2000-12-01 JP JP2001540982A patent/JP4721087B2/ja not_active Expired - Fee Related
- 2000-12-01 WO PCT/JP2000/008517 patent/WO2001040227A1/ja not_active Ceased
- 2000-12-01 EP EP00979050A patent/EP1236726B1/en not_active Expired - Lifetime
- 2000-12-01 DE DE60016454T patent/DE60016454T2/de not_active Expired - Lifetime
- 2000-12-01 AT AT00979050T patent/ATE283854T1/de not_active IP Right Cessation
- 2000-12-01 AU AU16506/01A patent/AU780419C/en not_active Ceased
- 2000-12-01 TW TW089125555A patent/TWI224597B/zh not_active IP Right Cessation
- 2000-12-01 BR BR0016111-0A patent/BR0016111A/pt not_active Application Discontinuation
2002
- 2002-05-31 NO NO20022609A patent/NO323631B1/no unknown

Also Published As

Publication number	Publication date
EP1236726B1 (en)	2004-12-01
CN1433419A (zh)	2003-07-30
AU780419B2 (en)	2005-03-17
US20040097511A1 (en)	2004-05-20
DE60016454D1 (de)	2005-01-05
KR100613176B1 (ko)	2006-08-17
MXPA02005465A (es)	2003-10-15
CA2394679A1 (en)	2001-06-07
ATE283854T1 (de)	2004-12-15
HUP0300641A2 (hu)	2003-06-28
AU1650601A (en)	2001-06-12
NO20022609D0 (no)	2002-05-31
ES2233479T3 (es)	2005-06-16
NZ519183A (en)	2005-02-25
EP1236726A4 (en)	2003-01-15
CN1246321C (zh)	2006-03-22
BR0016111A (pt)	2003-03-25
KR20030003218A (ko)	2003-01-09
US7119091B2 (en)	2006-10-10
EP1236726A1 (en)	2002-09-04
PT1236726E (pt)	2005-04-29
WO2001040227A1 (en)	2001-06-07
NO20022609L (no)	2002-07-26
JP4721087B2 (ja)	2011-07-13
AU780419C (en)	2005-09-29
DE60016454T2 (de)	2005-08-04
TWI224597B (en)	2004-12-01

Publication	Publication Date	Title
EP1236726B1 (en)	2004-12-01	Triazaspiro 5.5]undecane derivatives and drugs containing the same as the active ingredient
US7285552B2 (en)	2007-10-23	Drugs containing triazaspiro[5.5]undecane derivatives as the active ingredient
ES2407115T3 (es)	2013-06-11	Compuesto que contiene un grupo básico y uso del mismo
JP3558079B2 (ja)	2004-08-25	トリアザスピロ［５．５］ウンデカン誘導体およびそれらを有効成分とする薬剤
JPWO2001040227A1 (ja)	2003-06-03	トリアザスピロ［５．５］ウンデカン誘導体およびそれらを有効成分とする薬剤
AU2004220225B2 (en)	2010-06-17	Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient
JP5135795B2 (ja)	2013-02-06	塩基性基を含有する化合物およびその用途
EP1541574A1 (en)	2005-06-15	Triazaspiro 5.5 undecane derivatives and drugs comprisi ng the same as the active ingredient
US20060019977A1 (en)	2006-01-26	Spiroheterocyclic derivative compounds and drugs comprising the compound as the active ingredient
WO2007049771A1 (ja)	2007-05-03	塩基性基を含有する化合物およびその用途
JP2002348288A (ja)	2002-12-04	スピロ複素環誘導体およびそれらを有効成分とする薬剤
JPWO2004094424A1 (ja)	2006-07-13	含窒素複素環化合物およびその用途
WO2006090853A1 (ja)	2006-08-31	含窒素複素環化合物およびその医薬用途
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