ZA200400489B - Substituted 1-oxa-2,8-diaza-spiro(4,5)dec-2-ene derivatives as medicaments for the treatment of pain. - Google Patents
Substituted 1-oxa-2,8-diaza-spiro(4,5)dec-2-ene derivatives as medicaments for the treatment of pain. Download PDFInfo
- Publication number
- ZA200400489B ZA200400489B ZA200400489A ZA200400489A ZA200400489B ZA 200400489 B ZA200400489 B ZA 200400489B ZA 200400489 A ZA200400489 A ZA 200400489A ZA 200400489 A ZA200400489 A ZA 200400489A ZA 200400489 B ZA200400489 B ZA 200400489B
- Authority
- ZA
- South Africa
- Prior art keywords
- diaza
- dec
- spiro
- oxa
- ene
- Prior art date
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- ZTUPVEXGISXGGN-UHFFFAOYSA-N 1-oxa-2,8-diazaspiro[4.5]dec-2-ene Chemical class C1C=NOC11CCNCC1 ZTUPVEXGISXGGN-UHFFFAOYSA-N 0.000 title claims description 28
- 208000002193 Pain Diseases 0.000 title claims description 16
- 230000036407 pain Effects 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 7
- -1 (C¢-alkyl)-aryl Chemical group 0.000 claims description 196
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 33
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 17
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 150000004677 hydrates Chemical class 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 150000003840 hydrochlorides Chemical class 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010047700 Vomiting Diseases 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 208000004296 neuralgia Diseases 0.000 claims description 3
- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical class 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- BXLLMBABWWOTTJ-UHFFFAOYSA-N (8-benzylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)-[4-(4-chlorophenyl)piperazin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1N1CCN(C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)CC=2C=CC=CC=2)CC1 BXLLMBABWWOTTJ-UHFFFAOYSA-N 0.000 claims description 2
- LMGHPYAMWFVQFF-UHFFFAOYSA-N (8-benzylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)-[4-(naphthalen-2-ylmethyl)piperazin-1-yl]methanone Chemical compound C1CN(CC=2C=C3C=CC=CC3=CC=2)CCN1C(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 LMGHPYAMWFVQFF-UHFFFAOYSA-N 0.000 claims description 2
- MYTPKHMBCLTSCI-UHFFFAOYSA-N 1-[4-[8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]piperazin-1-yl]-2-phenylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)N2CCN(CC2)C(=O)CC=2C=CC=CC=2)CC1 MYTPKHMBCLTSCI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- PMZWQDAWZRDKGI-UHFFFAOYSA-N 2-[(8-benzylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl)amino]ethyl acetate Chemical compound C1C(C(=O)NCCOC(=O)C)=NOC21CCN(S(=O)(=O)CC=1C=CC=CC=1)CC2 PMZWQDAWZRDKGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- WZVASLAXHKBYNE-UHFFFAOYSA-N 8-(2,5-dichlorophenyl)sulfonyl-n-[1-(naphthalen-2-ylamino)-1-oxopropan-2-yl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC(Cl)=CC=C1Cl WZVASLAXHKBYNE-UHFFFAOYSA-N 0.000 claims description 2
- HNLGKAPXWAPRCL-UHFFFAOYSA-N 8-(2,5-dichlorophenyl)sulfonyl-n-[3-(2-methylpiperidin-1-yl)propyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound CC1CCCCN1CCCNC(=O)C(C1)=NOC21CCN(S(=O)(=O)C=1C(=CC=C(Cl)C=1)Cl)CC2 HNLGKAPXWAPRCL-UHFFFAOYSA-N 0.000 claims description 2
- QROJVJHKBLNTFG-UHFFFAOYSA-N 8-(2-chloropyridine-3-carbonyl)-n-cyclopentyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NC2CCCC2)CC1 QROJVJHKBLNTFG-UHFFFAOYSA-N 0.000 claims description 2
- RUWYXVWIZQHQBF-UHFFFAOYSA-N 8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(O)=O)CC1 RUWYXVWIZQHQBF-UHFFFAOYSA-N 0.000 claims description 2
- ZOHRBEYFZMULRO-UHFFFAOYSA-N 8-(4-nitrophenyl)sulfonyl-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC=2SC=CC=2)CC1 ZOHRBEYFZMULRO-UHFFFAOYSA-N 0.000 claims description 2
- XEOINQQPCTUJFJ-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-[(2,5-difluorophenyl)methyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC1=CC=C(F)C(CNC(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2SC(Cl)=CC=2)=C1 XEOINQQPCTUJFJ-UHFFFAOYSA-N 0.000 claims description 2
- ZMBZRBYEOQAMRJ-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-[1-(naphthalen-2-ylmethyl)pyrrolidin-3-yl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC2CN(CC=3C=C4C=CC=CC4=CC=3)CC2)CC1 ZMBZRBYEOQAMRJ-UHFFFAOYSA-N 0.000 claims description 2
- ADAFMRSNUNVYKD-UHFFFAOYSA-N 8-(benzenesulfonyl)-n-[2-(dimethylamino)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCCN(C)C)=NOC21CCN(S(=O)(=O)C=1C=CC=CC=1)CC2 ADAFMRSNUNVYKD-UHFFFAOYSA-N 0.000 claims description 2
- UPEPEEAISFWFAE-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-n-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(=O)NCCC=2C=CC=CC=2)C1 UPEPEEAISFWFAE-UHFFFAOYSA-N 0.000 claims description 2
- BGHUZBPSUHSOKD-UHFFFAOYSA-N 8-acetyl-n-benzyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(C(=O)C)CCC11ON=C(C(=O)NCC=2C=CC=CC=2)C1 BGHUZBPSUHSOKD-UHFFFAOYSA-N 0.000 claims description 2
- VNMYTZXTQQOUCR-UHFFFAOYSA-N 8-benzylsulfonyl-n-(2-phenylmethoxycyclopentyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)CC=1C(=O)NC1CCCC1OCC1=CC=CC=C1 VNMYTZXTQQOUCR-UHFFFAOYSA-N 0.000 claims description 2
- CKZQCLNKVBNLSN-UHFFFAOYSA-N 8-benzylsulfonyl-n-[4-(diethoxyphosphorylmethyl)phenyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)C(C1)=NOC21CCN(S(=O)(=O)CC=1C=CC=CC=1)CC2 CKZQCLNKVBNLSN-UHFFFAOYSA-N 0.000 claims description 2
- IWAOKDSYAFTQTN-UHFFFAOYSA-N 8-thiophen-2-ylsulfonyl-n-[1-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidin-3-yl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(NC(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2SC=CC=2)CC1 IWAOKDSYAFTQTN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 2
- LHXHKZQFOVPAPL-UHFFFAOYSA-N [3-methyl-4-(3-methylphenyl)piperazin-1-yl]-(8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)methanone Chemical compound CC1CN(C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2SC=CC=2)CCN1C1=CC=CC(C)=C1 LHXHKZQFOVPAPL-UHFFFAOYSA-N 0.000 claims description 2
- JRMWVXYUINGGCV-UHFFFAOYSA-N [4-(3-phenylpropyl)piperazin-1-yl]-(8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)methanone Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)C=2SC=CC=2)CC=1C(=O)N(CC1)CCN1CCCC1=CC=CC=C1 JRMWVXYUINGGCV-UHFFFAOYSA-N 0.000 claims description 2
- JDCGWTQYWRDIKC-UHFFFAOYSA-N [4-(naphthalen-2-ylmethyl)piperazin-1-yl]-[8-[3-(trifluoromethyl)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)N3CCN(CC=4C=C5C=CC=CC5=CC=4)CC3)CC2)=C1 JDCGWTQYWRDIKC-UHFFFAOYSA-N 0.000 claims description 2
- IZGKYAURGORETM-UHFFFAOYSA-N [8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]-[4-(1-phenylethyl)piperazin-1-yl]methanone Chemical compound C=1C=CC=CC=1C(C)N(CC1)CCN1C(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=C(C)C=C1 IZGKYAURGORETM-UHFFFAOYSA-N 0.000 claims description 2
- VNASIGYPRBRGCV-UHFFFAOYSA-N [8-(5-chlorothiophen-2-yl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]-(4-phenylpiperazin-1-yl)methanone Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)N2CCN(CC2)C=2C=CC=CC=2)CC1 VNASIGYPRBRGCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- XYEVWZKPSZNBBI-UHFFFAOYSA-N n-(1-phenylethyl)-8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=CS1 XYEVWZKPSZNBBI-UHFFFAOYSA-N 0.000 claims description 2
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- ARYGUIOMRAQAEZ-UHFFFAOYSA-N 8-(4-ethylbenzoyl)-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2SC=CC=2)CC1 ARYGUIOMRAQAEZ-UHFFFAOYSA-N 0.000 claims 1
- HPLAVFPHHPSFQU-UHFFFAOYSA-N 8-(4-fluorobenzoyl)-n-(2-methylpropyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCC(C)C)=NOC21CCN(C(=O)C=1C=CC(F)=CC=1)CC2 HPLAVFPHHPSFQU-UHFFFAOYSA-N 0.000 claims 1
- FLOYETIJZZFRGN-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC21CCN(S(=O)(=O)C=1C=CC(F)=CC=1)CC2 FLOYETIJZZFRGN-UHFFFAOYSA-N 0.000 claims 1
- CVUPGBHIZMCVTJ-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-(3-phenylpropyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCCCC=2C=CC=CC=2)CC1 CVUPGBHIZMCVTJ-UHFFFAOYSA-N 0.000 claims 1
- BIMYGJICMWRSFD-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-[1-(4-nitrophenyl)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=C(F)C=C1 BIMYGJICMWRSFD-UHFFFAOYSA-N 0.000 claims 1
- JOOLSNZOUDHHJP-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-[1-(naphthalen-2-ylamino)-1-oxopropan-2-yl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=C(F)C=C1 JOOLSNZOUDHHJP-UHFFFAOYSA-N 0.000 claims 1
- FVZXUCAIVVRZRI-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-[2-(3-methoxyphenyl)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound COC1=CC=CC(CCNC(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2C=CC(F)=CC=2)=C1 FVZXUCAIVVRZRI-UHFFFAOYSA-N 0.000 claims 1
- ZBDPXCDTOPAVTJ-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-[2-[3-(trifluoromethyl)phenyl]ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCCC=2C=C(C=CC=2)C(F)(F)F)CC1 ZBDPXCDTOPAVTJ-UHFFFAOYSA-N 0.000 claims 1
- OZYQSWHAVPYFAK-UHFFFAOYSA-N 8-(4-methoxybenzoyl)-n-[(5-methylfuran-2-yl)methyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2OC(C)=CC=2)CC1 OZYQSWHAVPYFAK-UHFFFAOYSA-N 0.000 claims 1
- AKOGMDVNLILWSW-UHFFFAOYSA-N 8-(4-methoxyphenyl)sulfonyl-n-(2-phenylcyclopropyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC2C(C2)C=2C=CC=CC=2)CC1 AKOGMDVNLILWSW-UHFFFAOYSA-N 0.000 claims 1
- AAWSNBDOPGWKOW-UHFFFAOYSA-N 8-(4-methylphenyl)sulfonyl-n-(4-phenoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 AAWSNBDOPGWKOW-UHFFFAOYSA-N 0.000 claims 1
- NUWYYLMOFCPHRW-UHFFFAOYSA-N 8-(4-phenoxybutanoyl)-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CC2(ON=C(C2)C(=O)NCC=2SC=CC=2)CCN1C(=O)CCCOC1=CC=CC=C1 NUWYYLMOFCPHRW-UHFFFAOYSA-N 0.000 claims 1
- DEZZEZUBXGWZHP-UHFFFAOYSA-N 8-(5-bromo-2-methoxyphenyl)sulfonyl-n-cyclopentyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound COC1=CC=C(Br)C=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC2CCCC2)CC1 DEZZEZUBXGWZHP-UHFFFAOYSA-N 0.000 claims 1
- JTFLBLLPKHGNKF-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-(2,2-diphenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 JTFLBLLPKHGNKF-UHFFFAOYSA-N 0.000 claims 1
- IIIMDDMCGVTNFV-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC2OC3=CC=CC=C3OC2)CC1 IIIMDDMCGVTNFV-UHFFFAOYSA-N 0.000 claims 1
- OZCFKDIKAXQBLR-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-(2-phenylmethoxycyclopentyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC2C(CCC2)OCC=2C=CC=CC=2)CC1 OZCFKDIKAXQBLR-UHFFFAOYSA-N 0.000 claims 1
- CFOMGGQBOSBOAS-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-(naphthalen-1-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C3=CC=CC=C3C=CC=2)CC1 CFOMGGQBOSBOAS-UHFFFAOYSA-N 0.000 claims 1
- MHWVUMCMAQEPKK-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-[1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC=2OCCOC=2C=1C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=C(Cl)S1 MHWVUMCMAQEPKK-UHFFFAOYSA-N 0.000 claims 1
- OHEWARDUTDUYMZ-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-[2-(1-methylpyrrolidin-2-yl)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound CN1CCCC1CCNC(=O)C(C1)=NOC21CCN(S(=O)(=O)C=1SC(Cl)=CC=1)CC2 OHEWARDUTDUYMZ-UHFFFAOYSA-N 0.000 claims 1
- RQPTVOACPLFGAN-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)sulfonyl-n-[3-(n-methylanilino)propyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC=CC=1N(C)CCCNC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=C(Cl)S1 RQPTVOACPLFGAN-UHFFFAOYSA-N 0.000 claims 1
- IQGFXCDYQYRDCH-UHFFFAOYSA-N 8-(5-tert-butyl-2-methylfuran-3-carbonyl)-n-(2-methylpropyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCC(C)C)=NOC21CCN(C(=O)C1=C(OC(=C1)C(C)(C)C)C)CC2 IQGFXCDYQYRDCH-UHFFFAOYSA-N 0.000 claims 1
- BICQWZLGVGBCKJ-UHFFFAOYSA-N 8-(5-tert-butyl-2-methylfuran-3-carbonyl)-n-cyclopentyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound O1C(C(C)(C)C)=CC(C(=O)N2CCC3(ON=C(C3)C(=O)NC3CCCC3)CC2)=C1C BICQWZLGVGBCKJ-UHFFFAOYSA-N 0.000 claims 1
- GDZKVWDYJGYJLZ-UHFFFAOYSA-N 8-(5-tert-butyl-2-methylpyrazole-3-carbonyl)-n-(2-ethylsulfanylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCCSCC)=NOC21CCN(C(=O)C=1N(N=C(C=1)C(C)(C)C)C)CC2 GDZKVWDYJGYJLZ-UHFFFAOYSA-N 0.000 claims 1
- QJNMRJMGKCUCGE-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(O)=O)C1 QJNMRJMGKCUCGE-UHFFFAOYSA-N 0.000 claims 1
- VJHFIAVYMAJQDB-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-n-(2-ethylsulfanylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCCSCC)=NOC21CCN(S(=O)(=O)N(C)C)CC2 VJHFIAVYMAJQDB-UHFFFAOYSA-N 0.000 claims 1
- BWNNRHDTCSQLJF-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-n-(2-phenylmethoxycyclopentyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(=O)NC2C(CCC2)OCC=2C=CC=CC=2)C1 BWNNRHDTCSQLJF-UHFFFAOYSA-N 0.000 claims 1
- UIPANGYLELCYKQ-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-n-[2-(n-ethyl-3-methylanilino)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC(C)=CC=1N(CC)CCNC(=O)C(C1)=NOC21CCN(S(=O)(=O)N(C)C)CC2 UIPANGYLELCYKQ-UHFFFAOYSA-N 0.000 claims 1
- PGZOLIAKNYMZDZ-UHFFFAOYSA-N 8-(dimethylsulfamoyl)-n-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(=O)NCC=2C=C(F)C(=CC=2)C(F)(F)F)C1 PGZOLIAKNYMZDZ-UHFFFAOYSA-N 0.000 claims 1
- BYUYADUKBRWTFT-UHFFFAOYSA-N 8-(naphthalene-1-carbonyl)-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound N=1OC2(CCN(CC2)C(=O)C=2C3=CC=CC=C3C=CC=2)CC=1C(=O)NCC1=CC=CS1 BYUYADUKBRWTFT-UHFFFAOYSA-N 0.000 claims 1
- ILCMYOHYEFUCQM-UHFFFAOYSA-N 8-(naphthalene-2-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC21CCN(C(=O)C=1C=C3C=CC=CC3=CC=1)CC2 ILCMYOHYEFUCQM-UHFFFAOYSA-N 0.000 claims 1
- RAOVVGSTCFXOTK-UHFFFAOYSA-N 8-[2-(3-chlorophenoxy)acetyl]-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=CC(OCC(=O)N2CCC3(ON=C(C3)C(=O)NCC=3SC=CC=3)CC2)=C1 RAOVVGSTCFXOTK-UHFFFAOYSA-N 0.000 claims 1
- HLUWHWJJMBRFCU-UHFFFAOYSA-N 8-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCC1(ON=1)CC=1C(=O)NCC1=CC=CS1 HLUWHWJJMBRFCU-UHFFFAOYSA-N 0.000 claims 1
- HLHTYXMHQWXWQP-UHFFFAOYSA-N 8-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]-n-(2-ethylsulfanylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCCSCC)=NOC21CCN(C(=O)C=1C(=NOC=1C)C=1C(=CC=CC=1F)Cl)CC2 HLHTYXMHQWXWQP-UHFFFAOYSA-N 0.000 claims 1
- YVEGSGJTWJCSAG-UHFFFAOYSA-N 8-[4-(trifluoromethoxy)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC21CCN(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC2 YVEGSGJTWJCSAG-UHFFFAOYSA-N 0.000 claims 1
- WMPNDVXLAXBLLK-UHFFFAOYSA-N 8-benzylsulfonyl-n-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)CC=1C(=O)NCCC1=CC=CC=C1 WMPNDVXLAXBLLK-UHFFFAOYSA-N 0.000 claims 1
- JXLKHGXAKSXEAE-UHFFFAOYSA-N 8-benzylsulfonyl-n-[(2-ethoxyphenyl)methyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound CCOC1=CC=CC=C1CNC(=O)C(C1)=NOC21CCN(S(=O)(=O)CC=1C=CC=CC=1)CC2 JXLKHGXAKSXEAE-UHFFFAOYSA-N 0.000 claims 1
- JWWORDQKRZZQGQ-UHFFFAOYSA-N 8-benzylsulfonyl-n-[2-(3-fluorophenyl)ethyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC1=CC=CC(CCNC(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)CC=2C=CC=CC=2)=C1 JWWORDQKRZZQGQ-UHFFFAOYSA-N 0.000 claims 1
- YDZBXMYTTXLEOD-UHFFFAOYSA-N COc1ccc(OC)c(CN(Cc2ccco2)C(=O)C2=NOC3(C2)CCN(CC3)S(=O)(=O)c2ccc(F)cc2)c1 Chemical compound COc1ccc(OC)c(CN(Cc2ccco2)C(=O)C2=NOC3(C2)CCN(CC3)S(=O)(=O)c2ccc(F)cc2)c1 YDZBXMYTTXLEOD-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- HDVPYGORGXLEQP-UHFFFAOYSA-N N=1OC2(CCN(CC2)C(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CC=1C(=O)NC1CCCC1 Chemical compound N=1OC2(CCN(CC2)C(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CC=1C(=O)NC1CCCC1 HDVPYGORGXLEQP-UHFFFAOYSA-N 0.000 claims 1
- VYLJLJLAQDHSLL-UHFFFAOYSA-N [1-[3-(benzylcarbamoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-2-methyl-1-oxopropan-2-yl] acetate Chemical compound C1CN(C(=O)C(C)(C)OC(=O)C)CCC11ON=C(C(=O)NCC=2C=CC=CC=2)C1 VYLJLJLAQDHSLL-UHFFFAOYSA-N 0.000 claims 1
- UCXQSWVFCOKWOU-UHFFFAOYSA-N [4-(2,4-dimethylphenyl)piperazin-1-yl]-[8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]methanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)N2CCN(CC2)C=2C(=CC(C)=CC=2)C)CC1 UCXQSWVFCOKWOU-UHFFFAOYSA-N 0.000 claims 1
- HOMSLEQXINMJMP-UHFFFAOYSA-N [4-(3-phenylpropyl)piperazin-1-yl]-[8-[4-(trifluoromethoxy)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]methanone Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)N2CCN(CCCC=3C=CC=CC=3)CC2)CC1 HOMSLEQXINMJMP-UHFFFAOYSA-N 0.000 claims 1
- SCWHASIJAUHHHT-UHFFFAOYSA-N [8-(4-fluorophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]-[4-(5-methylpyrazine-2-carbonyl)piperazin-1-yl]methanone Chemical compound C1=NC(C)=CN=C1C(=O)N1CCN(C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2C=CC(F)=CC=2)CC1 SCWHASIJAUHHHT-UHFFFAOYSA-N 0.000 claims 1
- HRNAUSMVSCBGIX-UHFFFAOYSA-N [8-[3-(trifluoromethyl)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl]-[4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=NC(N2CCN(CC2)C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 HRNAUSMVSCBGIX-UHFFFAOYSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- UXOLDCOJRAMLTQ-ZZXKWVIFSA-N ethyl (2e)-2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(\Cl)=N/O UXOLDCOJRAMLTQ-ZZXKWVIFSA-N 0.000 claims 1
- WFDULUFPKPBXOO-UHFFFAOYSA-N ethyl 1-[8-(4-tert-butylbenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(C1)=NOC21CCN(C(=O)C=1C=CC(=CC=1)C(C)(C)C)CC2 WFDULUFPKPBXOO-UHFFFAOYSA-N 0.000 claims 1
- NRXXZKQYLXVVFU-UHFFFAOYSA-N ethyl 1-[8-(5-tert-butyl-2-methylfuran-3-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(C1)=NOC21CCN(C(=O)C1=C(OC(=C1)C(C)(C)C)C)CC2 NRXXZKQYLXVVFU-UHFFFAOYSA-N 0.000 claims 1
- HYSZZLXDYIPRBX-UHFFFAOYSA-N ethyl 2-[[8-(3-chlorothiophene-2-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]acetate Chemical compound C1C(C(=O)NCC(=O)OCC)=NOC21CCN(C(=O)C1=C(C=CS1)Cl)CC2 HYSZZLXDYIPRBX-UHFFFAOYSA-N 0.000 claims 1
- LPGCOCIWGDIQGH-UHFFFAOYSA-N ethyl 3-[[8-(2-chlorophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]propanoate Chemical compound C1C(C(=O)NCCC(=O)OCC)=NOC21CCN(S(=O)(=O)C=1C(=CC=CC=1)Cl)CC2 LPGCOCIWGDIQGH-UHFFFAOYSA-N 0.000 claims 1
- BMWDNPYTKYCKIH-UHFFFAOYSA-N ethyl 3-[[8-(2-methyl-5-nitrophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]propanoate Chemical compound C1C(C(=O)NCCC(=O)OCC)=NOC21CCN(S(=O)(=O)C=1C(=CC=C(C=1)[N+]([O-])=O)C)CC2 BMWDNPYTKYCKIH-UHFFFAOYSA-N 0.000 claims 1
- CJZHKNKPIRQIDF-UHFFFAOYSA-N ethyl 3-[[8-(3,5-difluorobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]propanoate Chemical compound C1C(C(=O)NCCC(=O)OCC)=NOC21CCN(C(=O)C=1C=C(F)C=C(F)C=1)CC2 CJZHKNKPIRQIDF-UHFFFAOYSA-N 0.000 claims 1
- BAWOPIFGTFSDSZ-UHFFFAOYSA-N ethyl 3-[[8-(6-chloro-2-fluoro-3-methylbenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]propanoate Chemical compound C1C(C(=O)NCCC(=O)OCC)=NOC21CCN(C(=O)C=1C(=C(C)C=CC=1Cl)F)CC2 BAWOPIFGTFSDSZ-UHFFFAOYSA-N 0.000 claims 1
- NRUIVUXEUGPCOM-UHFFFAOYSA-N ethyl 4-[(8-butanoyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)CCC)CCC11ON=C(C(=O)NC2CCN(CC2)C(=O)OCC)C1 NRUIVUXEUGPCOM-UHFFFAOYSA-N 0.000 claims 1
- YXNIZCBOOCMVOM-UHFFFAOYSA-N ethyl 4-[[8-(2,4-difluorobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)C(C1)=NOC21CCN(C(=O)C=1C(=CC(F)=CC=1)F)CC2 YXNIZCBOOCMVOM-UHFFFAOYSA-N 0.000 claims 1
- VELQTNVKKXEIBD-UHFFFAOYSA-N ethyl 4-[[8-(2-methyl-5-nitrophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)C(C1)=NOC21CCN(S(=O)(=O)C=1C(=CC=C(C=1)[N+]([O-])=O)C)CC2 VELQTNVKKXEIBD-UHFFFAOYSA-N 0.000 claims 1
- UOICPRGJVHWIBE-UHFFFAOYSA-N ethyl 4-[[8-(4-bromobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)C(C1)=NOC21CCN(C(=O)C=1C=CC(Br)=CC=1)CC2 UOICPRGJVHWIBE-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- XWWLMPDAHBDPRQ-UHFFFAOYSA-N methyl 2-[[3-(2-methylpropylcarbamoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]sulfonyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC(C)C)CC1 XWWLMPDAHBDPRQ-UHFFFAOYSA-N 0.000 claims 1
- NCWCFBWWORYPBQ-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-2-[[8-(4-methoxyphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]amino]propanoate Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)C=2C=CC(OC)=CC=2)CC=1C(=O)NC(C(=O)OC)CC1=CC=C(Cl)C=C1 NCWCFBWWORYPBQ-UHFFFAOYSA-N 0.000 claims 1
- 238000005822 methylenation reaction Methods 0.000 claims 1
- QCRPURZINMXPEJ-UHFFFAOYSA-N n'-[4-(diethylamino)benzoyl]-8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbohydrazide Chemical class C1=CC(N(CC)CC)=CC=C1C(=O)NNC(=O)C(C1)=NOC21CCN(S(=O)(=O)C=1SC=CC=1)CC2 QCRPURZINMXPEJ-UHFFFAOYSA-N 0.000 claims 1
- LBKBAGGMDDLKBN-UHFFFAOYSA-N n,n-dimethyl-3-[4-(3-phenylpropyl)piperazine-1-carbonyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(=O)N2CCN(CCCC=3C=CC=CC=3)CC2)C1 LBKBAGGMDDLKBN-UHFFFAOYSA-N 0.000 claims 1
- XQPYQBSJZNOPMW-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-8-(5-chlorothiophen-2-yl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=C3OCOC3=CC=2)CC1 XQPYQBSJZNOPMW-UHFFFAOYSA-N 0.000 claims 1
- WMVFAKIQYALSDX-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1OC2=CC=CC=C2OC1CNC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=CS1 WMVFAKIQYALSDX-UHFFFAOYSA-N 0.000 claims 1
- OHJGMLZZYVFHCS-UHFFFAOYSA-N n-(2-cyanoethyl)-8-(2,5-dichlorophenyl)sulfonyl-n-(oxolan-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)N(CCC#N)CC3OCCC3)CC2)=C1 OHJGMLZZYVFHCS-UHFFFAOYSA-N 0.000 claims 1
- VFVNVSZERYXMMN-UHFFFAOYSA-N n-(2-cyanoethyl)-8-(2,5-dichlorophenyl)sulfonyl-n-(pyridin-3-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)N(CCC#N)CC=3C=NC=CC=3)CC2)=C1 VFVNVSZERYXMMN-UHFFFAOYSA-N 0.000 claims 1
- KNCFGATWYLTHHX-UHFFFAOYSA-N n-(2-cyanoethyl)-8-(2-phenylbutanoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)N(CC1)CCC21CC(C(=O)NCCC#N)=NO2 KNCFGATWYLTHHX-UHFFFAOYSA-N 0.000 claims 1
- MPNRHYBXFGYQKH-UHFFFAOYSA-N n-(2-cyanoethyl)-8-(4-fluorophenyl)sulfonyl-n-(2-pyridin-2-ylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)N(CCC#N)CCC=2N=CC=CC=2)CC1 MPNRHYBXFGYQKH-UHFFFAOYSA-N 0.000 claims 1
- AYQKGHUGIVCQMN-UHFFFAOYSA-N n-(2-cyanoethyl)-8-[2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(=O)N1CCC2(ON=C(C2)C(=O)NCCC#N)CC1)CC1=CC=CC=C1 AYQKGHUGIVCQMN-UHFFFAOYSA-N 0.000 claims 1
- LOIHHDDJXKCVAQ-UHFFFAOYSA-N n-(2-methylpropyl)-8-(naphthalene-1-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCC(C)C)=NOC21CCN(C(=O)C=1C3=CC=CC=C3C=CC=1)CC2 LOIHHDDJXKCVAQ-UHFFFAOYSA-N 0.000 claims 1
- RSGDZJCLIXQBLC-UHFFFAOYSA-N n-(2-methylpropyl)-8-propylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(S(=O)(=O)CCC)CCC11ON=C(C(=O)NCC(C)C)C1 RSGDZJCLIXQBLC-UHFFFAOYSA-N 0.000 claims 1
- GYMWQSLSXGSPTM-UHFFFAOYSA-N n-(2-phenylmethoxycyclopentyl)-8-[3-(trifluoromethyl)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)NC3C(CCC3)OCC=3C=CC=CC=3)CC2)=C1 GYMWQSLSXGSPTM-UHFFFAOYSA-N 0.000 claims 1
- LSXMGEFWZAFQAA-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-(2,3-dichlorobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=CC(C(=O)N2CCC3(ON=C(C3)C(=O)NCC3CC3)CC2)=C1Cl LSXMGEFWZAFQAA-UHFFFAOYSA-N 0.000 claims 1
- VEXPYSDSPCOHDO-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-(2,3-difluoro-4-methylbenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC1=C(F)C(C)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC2CC2)CC1 VEXPYSDSPCOHDO-UHFFFAOYSA-N 0.000 claims 1
- QHTLXCKWSUDQII-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-(2-phenoxypropanoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CC2(ON=C(C2)C(=O)NCC2CC2)CCN1C(=O)C(C)OC1=CC=CC=C1 QHTLXCKWSUDQII-UHFFFAOYSA-N 0.000 claims 1
- YRBXTHFHCAUXLJ-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-(4-phenoxybutanoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CC2(ON=C(C2)C(=O)NCC2CC2)CCN1C(=O)CCCOC1=CC=CC=C1 YRBXTHFHCAUXLJ-UHFFFAOYSA-N 0.000 claims 1
- VIFIJXXBXRBFFM-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-[3-fluoro-4-(trifluoromethyl)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC(C(=O)N2CCC3(ON=C(C3)C(=O)NCC3CC3)CC2)=C1 VIFIJXXBXRBFFM-UHFFFAOYSA-N 0.000 claims 1
- KJRVWAJSEBMQAX-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-[4-(trifluoromethoxy)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC2CC2)CC1 KJRVWAJSEBMQAX-UHFFFAOYSA-N 0.000 claims 1
- WNVHAWDFKBZINF-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-[4-(trifluoromethyl)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC2CC2)CC1 WNVHAWDFKBZINF-UHFFFAOYSA-N 0.000 claims 1
- KAEJKFKBJFZCSC-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-[4-(trifluoromethylsulfanyl)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(SC(F)(F)F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC2CC2)CC1 KAEJKFKBJFZCSC-UHFFFAOYSA-N 0.000 claims 1
- AMDKZKKTVGKAAB-UHFFFAOYSA-N n-(cyclopropylmethyl)-8-hexanoyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(C(=O)CCCCC)CCC11ON=C(C(=O)NCC2CC2)C1 AMDKZKKTVGKAAB-UHFFFAOYSA-N 0.000 claims 1
- PZABPPGAWGDQLQ-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-8-[4-(trifluoromethoxy)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=CN=CC=2)CC1 PZABPPGAWGDQLQ-UHFFFAOYSA-N 0.000 claims 1
- GMAMOWAQIDATAV-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-8-[4-(trifluoromethylsulfanyl)benzoyl]-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(SC(F)(F)F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2SC=CC=2)CC1 GMAMOWAQIDATAV-UHFFFAOYSA-N 0.000 claims 1
- PDKUJMZDOVAMBJ-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-8-(dimethylsulfamoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC11ON=C(C(=O)NCC=2C(=CC(F)=CC=2)F)C1 PDKUJMZDOVAMBJ-UHFFFAOYSA-N 0.000 claims 1
- BXIUSSHMWQDUQS-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-8-(4-fluorophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C(=CC=CC=2)F)CC1 BXIUSSHMWQDUQS-UHFFFAOYSA-N 0.000 claims 1
- AJGRXEQLVFVNMR-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=C(Cl)C=C(Cl)C=2)CC1 AJGRXEQLVFVNMR-UHFFFAOYSA-N 0.000 claims 1
- NYKXXZRLTJFDNX-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-8-[3-(trifluoromethyl)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)NCC=3C=C(Cl)C=CC=3)CC2)=C1 NYKXXZRLTJFDNX-UHFFFAOYSA-N 0.000 claims 1
- ICTDLMKLURBMSA-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-8-[4-(trifluoromethoxy)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1 ICTDLMKLURBMSA-UHFFFAOYSA-N 0.000 claims 1
- DQWCAKDDHZGVDM-UHFFFAOYSA-N n-[1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]-8-thiophen-2-ylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C=1C=CC=2OCCOC=2C=1C(C)NC(=O)C(C1)=NOC1(CC1)CCN1S(=O)(=O)C1=CC=CS1 DQWCAKDDHZGVDM-UHFFFAOYSA-N 0.000 claims 1
- RUZNHFBPFSZGEC-UHFFFAOYSA-N n-[1-(4-chlorophenyl)propan-2-yl]-8-(4-methoxyphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC(C)CC=2C=CC(Cl)=CC=2)CC1 RUZNHFBPFSZGEC-UHFFFAOYSA-N 0.000 claims 1
- DJACKYNRVNNXJA-UHFFFAOYSA-N n-[1-(4-chlorophenyl)propan-2-yl]-8-(5-chlorothiophen-2-yl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)C=2SC(Cl)=CC=2)CC=1C(=O)NC(C)CC1=CC=C(Cl)C=C1 DJACKYNRVNNXJA-UHFFFAOYSA-N 0.000 claims 1
- QFECLRSLIZUTCR-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-8-(4-methoxyphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCCC=2C(=CC=CC=2)F)CC1 QFECLRSLIZUTCR-UHFFFAOYSA-N 0.000 claims 1
- LYOSECCMSLRFCU-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)CC1 LYOSECCMSLRFCU-UHFFFAOYSA-N 0.000 claims 1
- UVPHIWXUWOXDCC-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-8-[4-(trifluoromethoxy)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)CC1 UVPHIWXUWOXDCC-UHFFFAOYSA-N 0.000 claims 1
- IOJVIQUJBQRMMN-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-8-[4-(trifluoromethoxy)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C(C1)=NOC21CCN(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC2 IOJVIQUJBQRMMN-UHFFFAOYSA-N 0.000 claims 1
- WKBWFENHXDCIGM-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-(4-methylphenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1C(C(=O)NCCN(C)C)=NOC21CCN(S(=O)(=O)C=1C=CC(C)=CC=1)CC2 WKBWFENHXDCIGM-UHFFFAOYSA-N 0.000 claims 1
- OWJSZJJDAOPPDE-UHFFFAOYSA-N n-benzhydryl-8-(5-chlorothiophen-2-yl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1CCC2(ON=C(C2)C(=O)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 OWJSZJJDAOPPDE-UHFFFAOYSA-N 0.000 claims 1
- BUZBWEFYJOITKZ-UHFFFAOYSA-N n-benzyl-8-(2,5-dichlorophenyl)sulfonyl-n-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)N(CCC=3C=CC=CC=3)CC=3C=CC=CC=3)CC2)=C1 BUZBWEFYJOITKZ-UHFFFAOYSA-N 0.000 claims 1
- JCQBIRPNKWLAMG-UHFFFAOYSA-N n-benzyl-8-(2,5-dimethylfuran-3-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound O1C(C)=CC(C(=O)N2CCC3(ON=C(C3)C(=O)NCC=3C=CC=CC=3)CC2)=C1C JCQBIRPNKWLAMG-UHFFFAOYSA-N 0.000 claims 1
- BMLDLUBRNTWDTM-UHFFFAOYSA-N n-benzyl-8-(2-ethylsulfanylpyridine-3-carbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound CCSC1=NC=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=CC=CC=2)CC1 BMLDLUBRNTWDTM-UHFFFAOYSA-N 0.000 claims 1
- GCCUYXOOZYAYAS-UHFFFAOYSA-N n-benzyl-8-(2-phenoxypropanoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1CC2(ON=C(C2)C(=O)NCC=2C=CC=CC=2)CCN1C(=O)C(C)OC1=CC=CC=C1 GCCUYXOOZYAYAS-UHFFFAOYSA-N 0.000 claims 1
- LJFDGLLXOODMSN-UHFFFAOYSA-N n-benzyl-8-(3-chloro-4-fluorobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=CC=CC=2)CC1 LJFDGLLXOODMSN-UHFFFAOYSA-N 0.000 claims 1
- HWLDJRZQSYTHEK-UHFFFAOYSA-N n-benzyl-8-(3-chlorophenyl)sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound ClC1=CC=CC(S(=O)(=O)N2CCC3(ON=C(C3)C(=O)NCC=3C=CC=CC=3)CC2)=C1 HWLDJRZQSYTHEK-UHFFFAOYSA-N 0.000 claims 1
- SRBLSCNYDHWNCT-UHFFFAOYSA-N n-benzyl-8-(4-bromobenzoyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound C1=CC(Br)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2C=CC=CC=2)CC1 SRBLSCNYDHWNCT-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10130020A DE10130020A1 (de) | 2001-06-25 | 2001-06-25 | Substituierte 1-Oxa-2,8-diaza-spiro[4.5]dec-2-en-derivate |
Publications (1)
Publication Number | Publication Date |
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ZA200400489B true ZA200400489B (en) | 2004-10-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200400489A ZA200400489B (en) | 2001-06-25 | 2004-01-22 | Substituted 1-oxa-2,8-diaza-spiro(4,5)dec-2-ene derivatives as medicaments for the treatment of pain. |
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US (2) | US8048890B2 (es) |
EP (1) | EP1401841B1 (es) |
JP (1) | JP4410554B2 (es) |
KR (1) | KR100917112B1 (es) |
CN (1) | CN1315840C (es) |
AR (1) | AR036098A1 (es) |
AT (1) | ATE302782T1 (es) |
AU (1) | AU2002310768B2 (es) |
BR (1) | BR0211053A (es) |
CA (1) | CA2451859C (es) |
CO (1) | CO5540301A2 (es) |
CZ (1) | CZ20033432A3 (es) |
DE (2) | DE10130020A1 (es) |
DK (1) | DK1401841T3 (es) |
EC (1) | ECSP034924A (es) |
ES (1) | ES2245402T3 (es) |
HK (1) | HK1064669A1 (es) |
HU (1) | HU228774B1 (es) |
IL (2) | IL159544A0 (es) |
MX (1) | MXPA03012013A (es) |
NO (1) | NO332217B1 (es) |
NZ (1) | NZ530689A (es) |
PE (1) | PE20030146A1 (es) |
PL (1) | PL214290B1 (es) |
PT (1) | PT1401841E (es) |
RU (1) | RU2296128C2 (es) |
SI (1) | SI1401841T1 (es) |
SK (1) | SK287390B6 (es) |
WO (1) | WO2003000699A1 (es) |
ZA (1) | ZA200400489B (es) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10130020A1 (de) | 2001-06-25 | 2003-12-04 | Gruenenthal Gmbh | Substituierte 1-Oxa-2,8-diaza-spiro[4.5]dec-2-en-derivate |
US20040092519A1 (en) * | 2002-08-14 | 2004-05-13 | Fred Hassan | New treatment for hot flashes |
DE102004023635A1 (de) * | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
DE102005016170A1 (de) * | 2005-04-07 | 2006-10-12 | Grünenthal GmbH | 4,5,6,7- Tetrahydro-isoxazolo(4,5c)pyridin-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
DE102005044814A1 (de) * | 2005-05-19 | 2006-11-23 | Grünenthal GmbH | Substituierte Sprio-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
DE102005044813A1 (de) | 2005-05-19 | 2007-10-04 | Grünenthal GmbH | Substituierte Spiro-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
DE102005023784A1 (de) * | 2005-05-19 | 2006-11-30 | Grünenthal GmbH | Substituierte Spiro-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
US8614324B2 (en) * | 2008-10-31 | 2013-12-24 | Pain Therapeutics, Inc. | Filamin A binding anti-inflammatory and analgesic |
US9340558B2 (en) | 2007-11-02 | 2016-05-17 | Pain Therapeutics Inc. | Filamin a binding anti-inflammatory and analgesic |
US8653068B2 (en) | 2009-10-30 | 2014-02-18 | Pain Therapeutics, Inc. | Filamin A binding anti-inflammatory and analgesic |
CA2779252C (en) * | 2008-10-31 | 2015-05-05 | Pain Therapeutics, Inc. | Filamin a-binding anti-inflammatory analgesic |
US8580808B2 (en) * | 2009-10-30 | 2013-11-12 | Pain Therapeutic, Inc. | Filamin A-binding anti-inflammatory analgesic |
US20100279996A1 (en) * | 2009-05-04 | 2010-11-04 | Lindsay Burns Barbier | Novel analgesic that binds filamin a |
KR20150116466A (ko) * | 2009-01-26 | 2015-10-15 | 이스라엘 인스티튜트 포 바이올로지컬 리서치 | 이환형 헤테로사이클릭 스피로 화합물 |
US8580809B2 (en) * | 2009-10-30 | 2013-11-12 | Pain Therapeutics, Inc. | Filamin A-binding anti-inflammatory analgesic |
US8822464B2 (en) | 2011-11-28 | 2014-09-02 | Boehringer Ingelheim International Gmbh | N-aryl-piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
US8741892B2 (en) | 2011-12-05 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Compounds |
US8642774B2 (en) * | 2011-12-08 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Compounds |
US8846948B2 (en) | 2011-12-13 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Compounds |
US8796467B2 (en) | 2011-12-13 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Compounds |
US8716277B2 (en) | 2011-12-14 | 2014-05-06 | Boehringer Ingelheim International Gmbh | Substituted imidazole compounds useful as positive allosteric modulators of mGlu5 receptor activity |
US8883789B2 (en) | 2011-12-14 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
US8937176B2 (en) | 2011-12-14 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Compounds |
US8889677B2 (en) | 2012-01-17 | 2014-11-18 | Boehringer Ingellheim International GmbH | Substituted triazoles useful as mGlu5 receptor modulators |
EP2872899B1 (en) | 2012-07-13 | 2018-07-11 | Pain Therapeutics, Inc. | Alzheimer's disease assay in a living patient |
WO2014011917A2 (en) | 2012-07-13 | 2014-01-16 | Pain Therapeutics, Inc. | A method of inhibiting tau phosphorylation |
US9433604B2 (en) | 2013-10-08 | 2016-09-06 | Pain Therapeutics Inc. | Method for inhibiting growth of cancer cells |
MX2018008640A (es) | 2016-01-13 | 2018-11-19 | Gruenenthal Gmbh | Derivados de 3-(carboxietil)-8-amino-2-oxo-1,3-diaza-espiro-[4.5]- decano. |
AR107434A1 (es) | 2016-01-13 | 2018-05-02 | Gruenenthal Gmbh | Derivados de 3-((hetero)aril)-8-amino-2-oxo-1,3-diaza-espiro-[4.5]-decano |
BR112018014303B1 (pt) | 2016-01-13 | 2023-10-03 | Grünenthal GmbH | Derivados de 3-((hetero-)aril)-alquil-8-amino-2-oxo-1,3-diaza-espiro-[4.5]-decano |
HUE051642T2 (hu) | 2016-01-13 | 2021-03-01 | Gruenenthal Gmbh | 8-amino-2-oxo-1,3-diaza-spiro-[4,5]-dekán származékok |
WO2017121649A1 (en) | 2016-01-13 | 2017-07-20 | Grünenthal GmbH | 3-(carboxymethyl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives |
HRP20220026T1 (hr) * | 2017-04-12 | 2022-04-01 | Il Dong Pharmaceutical Co., Ltd. | Derivati izoksazola kao agonisti nuklearnog receptora i njihove uporabe |
CN109793713B (zh) * | 2019-03-26 | 2021-05-28 | 李世系 | 一种用于麻醉的短效催眠镇静的药物组合物及其注射剂制备方法及应用 |
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NL127065C (es) * | 1964-04-22 | |||
GB1227365A (es) * | 1968-07-29 | 1971-04-07 | ||
JPH02164882A (ja) * | 1988-12-20 | 1990-06-25 | Yamanouchi Pharmaceut Co Ltd | スピロ化合物及びその中間体 |
US5534520A (en) | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
US5073560A (en) * | 1990-07-20 | 1991-12-17 | Fisons Corporation | Spiro-isoxazolidine derivatives as cholinergic agents |
US5849736A (en) * | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
US5739336A (en) | 1995-06-23 | 1998-04-14 | Syntex (U.S.A.) Inc. | 1,3,8-triaza- and 3,8-diaza-1-oxaspiro 4,5! decane derivatives |
DE19528472A1 (de) | 1995-08-03 | 1997-02-06 | Boehringer Ingelheim Kg | Neues Verfahren zur Herstellung von Norbenzomorphan einer Zwischenstufe bei Herstellung von pharmazeutisch wertvollen Benzomorphanderivaten, insbesondere von (-)-(1R,5S,S"R)-3'-Hydroxy-2-(2-methoxypropyl-)-5,9,9-trimethyl-6,7 benzomorphan |
EP0854869B1 (en) * | 1995-09-29 | 2004-08-25 | Eli Lilly And Company | Spiro compounds as inhibitors of fibrinogen-dependent platelet aggregation |
JP2001527513A (ja) * | 1996-03-15 | 2001-12-25 | デュポン ファーマシューティカルズ カンパニー | スピロ環インテグリン阻害剤 |
ZA972195B (en) * | 1996-03-15 | 1998-09-14 | Du Pont Merck Pharma | Spirocycle integrin inhibitors |
WO1998043962A1 (en) * | 1997-03-28 | 1998-10-08 | Du Pont Pharmaceuticals Company | Heterocyclic integrin inhibitor prodrugs |
US6548677B1 (en) | 1998-11-18 | 2003-04-15 | Basf Aktiengesellschaft | Method of producing 2-alkyl-3-(4,5-dihydroisoxazole-3-yl)-halobenzenes |
KR20030000243A (ko) | 2001-06-22 | 2003-01-06 | 이 석 민 | 동물사료 제조방법 및 그에 적합한 기밀 플라스틱백발효용기 |
DE10130020A1 (de) | 2001-06-25 | 2003-12-04 | Gruenenthal Gmbh | Substituierte 1-Oxa-2,8-diaza-spiro[4.5]dec-2-en-derivate |
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- 2002-06-21 CN CNB028166825A patent/CN1315840C/zh not_active Expired - Fee Related
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