NO332217B1 - Substituerte 1-oksa-2,8-diaza-spiro[4,5]dec-2-en-derivater, fremgangsmate for fremstilling derav, anvendelse derav samt legemiddel inneholdende minst ett slikt derivat. - Google Patents

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Publication number

NO332217B1

NO332217B1 NO20035730A NO20035730A NO332217B1 NO 332217 B1 NO332217 B1 NO 332217B1 NO 20035730 A NO20035730 A NO 20035730A NO 20035730 A NO20035730 A NO 20035730A NO 332217 B1 NO332217 B1 NO 332217B1

Authority

NO

Norway

Prior art keywords

diaza

dec

oxa

spiro

ene

Prior art date

2001-06-25

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• 238000000034 method Methods 0.000 title claims abstract description 25
• 239000003814 drug Substances 0.000 title claims abstract description 22
• 238000002360 preparation method Methods 0.000 title claims abstract description 20
• ZTUPVEXGISXGGN-UHFFFAOYSA-N 1-oxa-2,8-diazaspiro[4.5]dec-2-ene Chemical class C1C=NOC11CCNCC1 ZTUPVEXGISXGGN-UHFFFAOYSA-N 0.000 title claims abstract description 16
• 229940079593 drug Drugs 0.000 title claims abstract description 13
• 150000001875 compounds Chemical class 0.000 claims abstract description 61
• -1 (C 1-6 -alkyl)-aryl Chemical group 0.000 claims description 249
• 125000000217 alkyl group Chemical group 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 46
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 239000000460 chlorine Substances 0.000 claims description 42
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 41
• 229910052801 chlorine Inorganic materials 0.000 claims description 40
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 35
• 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 34
• 239000002253 acid Substances 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 23
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 150000007513 acids Chemical class 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
• 208000002193 Pain Diseases 0.000 claims description 15
• 238000002156 mixing Methods 0.000 claims description 14
• 150000003840 hydrochlorides Chemical class 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 238000011321 prophylaxis Methods 0.000 claims description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
• 238000006243 chemical reaction Methods 0.000 claims description 9
• 230000036407 pain Effects 0.000 claims description 9
• LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
• 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 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 6
• 125000001637 1-naphthyl group Chemical class [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
• 125000001622 2-naphthyl group Chemical class [H]C1=C([H])C([H])=C2C([H])=C(*)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
• 206010002091 Anaesthesia Diseases 0.000 claims description 6
• 208000000094 Chronic Pain Diseases 0.000 claims description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
• 230000037005 anaesthesia Effects 0.000 claims description 6
• 238000001949 anaesthesia Methods 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
• 150000001732 carboxylic acid derivatives Chemical group 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
• 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 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 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 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 208000011117 substance-related disease Diseases 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• JIMSXLUBRRQALI-UHFFFAOYSA-N 2-phenylmethoxycyclopentan-1-amine Chemical compound NC1CCCC1OCC1=CC=CC=C1 JIMSXLUBRRQALI-UHFFFAOYSA-N 0.000 claims description 5
• YEDFKHQGIIPYQX-UHFFFAOYSA-N 8-(5-chlorothiophen-2-yl)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=1SC(Cl)=CC=1)CC2 YEDFKHQGIIPYQX-UHFFFAOYSA-N 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000004494 ethyl ester group Chemical group 0.000 claims description 5
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 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
• 208000007848 Alcoholism Diseases 0.000 claims description 4
• 125000006847 BOC protecting group Chemical group 0.000 claims description 4
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims description 4
• 208000010412 Glaucoma Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims description 4
• 206010047700 Vomiting Diseases 0.000 claims description 4
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 239000004305 biphenyl Chemical group 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 206010008118 cerebral infarction Diseases 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 206010013663 drug dependence Diseases 0.000 claims description 4
• 206010015037 epilepsy Diseases 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 229940126601 medicinal product Drugs 0.000 claims description 4
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
• LFIDLDUNPSPAQT-UHFFFAOYSA-N 8-(4-methoxyphenyl)sulfonyl-n-(2-phenylmethoxycyclopentyl)-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(CCC2)OCC=2C=CC=CC=2)CC1 LFIDLDUNPSPAQT-UHFFFAOYSA-N 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 208000019695 Migraine disease Diseases 0.000 claims description 3
• 208000003251 Pruritus Diseases 0.000 claims description 3
• 208000009205 Tinnitus Diseases 0.000 claims description 3
• 206010046543 Urinary incontinence Diseases 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
• 150000003254 radicals Chemical class 0.000 claims description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
• 231100000886 tinnitus Toxicity 0.000 claims description 3
• ZHVDHKWFWHEYHT-UHFFFAOYSA-N (4-cycloheptylpiperazin-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)CCN1C1CCCCCC1 ZHVDHKWFWHEYHT-UHFFFAOYSA-N 0.000 claims description 2
• RPBMCVGOBYQCFF-UHFFFAOYSA-N (8-benzylsulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)-[4-(2-methylphenyl)piperazin-1-yl]methanone Chemical compound CC1=CC=CC=C1N1CCN(C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)CC=2C=CC=CC=2)CC1 RPBMCVGOBYQCFF-UHFFFAOYSA-N 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 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
• XSFLBXNZRBRWKQ-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-[4-[8-[3-(trifluoromethyl)phenyl]sulfonyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carbonyl]piperazin-1-yl]ethanone Chemical compound C1=C(F)C(F)=CC=C1CC(=O)N1CCN(C(=O)C=2CC3(ON=2)CCN(CC3)S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 XSFLBXNZRBRWKQ-UHFFFAOYSA-N 0.000 claims description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-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
• ZIABGSHEOXSNMP-UHFFFAOYSA-N 3-(4-cycloheptylpiperazine-1-carbonyl)-n,n-dimethyl-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(CC2)C2CCCCCC2)C1 ZIABGSHEOXSNMP-UHFFFAOYSA-N 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
• 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
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
• WOVKNEMCUCDEHA-UHFFFAOYSA-N 8-(2,4-difluorobenzoyl)-n-(oxolan-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC2OCCC2)CC1 WOVKNEMCUCDEHA-UHFFFAOYSA-N 0.000 claims description 2
• UKYGQNRZCGJRNE-UHFFFAOYSA-N 8-(2,5-dichlorophenyl)sulfonyl-n-methyl-n-(pyridin-3-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound N=1OC2(CCN(CC2)S(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)CC=1C(=O)N(C)CC1=CC=CN=C1 UKYGQNRZCGJRNE-UHFFFAOYSA-N 0.000 claims description 2
• GGCCIMUJTCTMLD-UHFFFAOYSA-N 8-(3-chloro-2-fluorobenzoyl)-n-(thiophen-2-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide Chemical compound FC1=C(Cl)C=CC=C1C(=O)N1CCC2(ON=C(C2)C(=O)NCC=2SC=CC=2)CC1 GGCCIMUJTCTMLD-UHFFFAOYSA-N 0.000 claims description 2
• PYCWLEMUDBHXKI-UHFFFAOYSA-N 8-(3-chlorobenzoyl)-n-(thiophen-2-ylmethyl)-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)NCC=3SC=CC=3)CC2)=C1 PYCWLEMUDBHXKI-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• QCFWUDCIAWPNAH-UHFFFAOYSA-N 8-(4-fluorophenyl)sulfonyl-n-(2-phenylmethoxycyclopentyl)-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)NC2C(CCC2)OCC=2C=CC=CC=2)CC1 QCFWUDCIAWPNAH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
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• 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 description 2
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