SI3119782T1 - COMPOUNDS 2,7-DIAZASPIRO (3.5) NONANA - Google Patents
COMPOUNDS 2,7-DIAZASPIRO (3.5) NONANA Download PDFInfo
- Publication number
- SI3119782T1 SI3119782T1 SI201530219T SI201530219T SI3119782T1 SI 3119782 T1 SI3119782 T1 SI 3119782T1 SI 201530219 T SI201530219 T SI 201530219T SI 201530219 T SI201530219 T SI 201530219T SI 3119782 T1 SI3119782 T1 SI 3119782T1
- Authority
- SI
- Slovenia
- Prior art keywords
- diazaspiro
- sulfonyl
- nonan
- 6alkyl
- methoxyphenyl
- Prior art date
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- DROZYMFJWSYDRY-UHFFFAOYSA-N 2,7-diazaspiro[3.5]nonane Chemical class C1NCC11CCNCC1 DROZYMFJWSYDRY-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 239000003814 drug Substances 0.000 claims abstract 4
- 230000002265 prevention Effects 0.000 claims abstract 3
- 208000030159 metabolic disease Diseases 0.000 claims abstract 2
- 230000004770 neurodegeneration Effects 0.000 claims abstract 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 229910052760 oxygen Inorganic materials 0.000 claims 30
- -1 haloC1-6alkyl Chemical group 0.000 claims 29
- 229910052799 carbon Inorganic materials 0.000 claims 23
- 229910052757 nitrogen Inorganic materials 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 10
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- LVWKQKBWFTVHLB-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-(3-fluorophenyl)-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound FC1=CC=CC(NC(=O)N2CC3(C2)CCN(CC3)S(=O)(=O)C=2C=CC=CC=2)=C1 LVWKQKBWFTVHLB-UHFFFAOYSA-N 0.000 claims 5
- SGODQWIOWBOYKT-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-phenyl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)CN1C(=O)NC1=CC=CC=C1 SGODQWIOWBOYKT-UHFFFAOYSA-N 0.000 claims 5
- BLOKECMLIIWMCH-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-propan-2-yl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1N(C(=O)NC(C)C)CC21CCN(S(=O)(=O)C=1C=CC=CC=1)CC2 BLOKECMLIIWMCH-UHFFFAOYSA-N 0.000 claims 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- GVNJESYLNCMALL-UHFFFAOYSA-N n-(3-cyanophenyl)-7-methylsulfonyl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC11CN(C(=O)NC=2C=C(C=CC=2)C#N)C1 GVNJESYLNCMALL-UHFFFAOYSA-N 0.000 claims 4
- RPFCWYZXPVGZMD-UHFFFAOYSA-N n-(3-fluorophenyl)-7-methylsulfonyl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC11CN(C(=O)NC=2C=C(F)C=CC=2)C1 RPFCWYZXPVGZMD-UHFFFAOYSA-N 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- MIPCJURDXWBZGS-UHFFFAOYSA-N 7-methylsulfonyl-n-phenyl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC11CN(C(=O)NC=2C=CC=CC=2)C1 MIPCJURDXWBZGS-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- BCYYATIMCMWEAV-UHFFFAOYSA-N n-(4-methoxyphenyl)-7-methylsulfonyl-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1CC2(CCN(CC2)S(C)(=O)=O)C1 BCYYATIMCMWEAV-UHFFFAOYSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 2
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 2
- IJMSCUUGZYBRML-UHFFFAOYSA-N 2h-benzotriazol-5-yl-[7-[2-(3-chlorophenyl)ethylsulfonyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound ClC1=CC=CC(CCS(=O)(=O)N2CCC3(CN(C3)C(=O)C3=CC4=NNN=C4C=C3)CC2)=C1 IJMSCUUGZYBRML-UHFFFAOYSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- VIFSDEIEVJLEFA-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-(4-methoxyphenyl)-2,7-diazaspiro[3.5]nonane-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1CC2(CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)C1 VIFSDEIEVJLEFA-UHFFFAOYSA-N 0.000 claims 2
- 206010003694 Atrophy Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000000501 Lipidoses Diseases 0.000 claims 2
- 206010024585 Lipidosis Diseases 0.000 claims 2
- 230000037444 atrophy Effects 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 230000001771 impaired effect Effects 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- KCVKVMKMXZXHEN-UHFFFAOYSA-N 2-methylnonanamide Chemical compound CCCCCCCC(C)C(N)=O KCVKVMKMXZXHEN-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- BSZDGZNXEHKOFN-UHFFFAOYSA-N 7-[4-(difluoromethoxy)phenyl]sulfonyl-2-(4-methoxyphenyl)sulfonyl-2,7-diazaspiro[3.5]nonane Chemical compound FC(OC1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)S(=O)(=O)C2=CC=C(C=C2)OC)CC1)F BSZDGZNXEHKOFN-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- YCBIHKFWSRJXRS-UHFFFAOYSA-N C(C)OC1=C(C#N)C=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1 Chemical compound C(C)OC1=C(C#N)C=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1 YCBIHKFWSRJXRS-UHFFFAOYSA-N 0.000 claims 1
- FKCLZIVMKRFCRZ-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1)C Chemical compound C(C)OC1=C(C=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1)C FKCLZIVMKRFCRZ-UHFFFAOYSA-N 0.000 claims 1
- WJXUIGMNGALNNT-UHFFFAOYSA-N C(C)OC1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)S(=O)(=O)C2=CC=C(C=C2)OC)CC1 Chemical compound C(C)OC1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)S(=O)(=O)C2=CC=C(C=C2)OC)CC1 WJXUIGMNGALNNT-UHFFFAOYSA-N 0.000 claims 1
- HBLZORMEGDDHIS-UHFFFAOYSA-N C(CCC)C1=NSC(=N1)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC Chemical compound C(CCC)C1=NSC(=N1)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC HBLZORMEGDDHIS-UHFFFAOYSA-N 0.000 claims 1
- JYEGKASWJXCIKA-UHFFFAOYSA-N C1(CC1)C1=NSC(=N1)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC Chemical compound C1(CC1)C1=NSC(=N1)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC JYEGKASWJXCIKA-UHFFFAOYSA-N 0.000 claims 1
- CMMABCBPOOMCOE-UHFFFAOYSA-N C1(CCCCC1)CS(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1 Chemical compound C1(CCCCC1)CS(=O)(=O)N1CCC2(CN(C2)C2=NC(=NS2)CC2=CC=C(C=C2)F)CC1 CMMABCBPOOMCOE-UHFFFAOYSA-N 0.000 claims 1
- OUVOUIDJFKYNMR-UHFFFAOYSA-N CC(=O)NC1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 Chemical compound CC(=O)NC1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 OUVOUIDJFKYNMR-UHFFFAOYSA-N 0.000 claims 1
- VNIAWHHUQWYCOJ-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 Chemical compound CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 VNIAWHHUQWYCOJ-UHFFFAOYSA-N 0.000 claims 1
- YKLHLZIAFZPUSO-UHFFFAOYSA-N CC1=C(C=CC=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 Chemical compound CC1=C(C=CC=C1)S(=O)(=O)N1CCC2(CN(C2)C2=NC(CC3=CC=C(F)C=C3)=NS2)CC1 YKLHLZIAFZPUSO-UHFFFAOYSA-N 0.000 claims 1
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- IWOCHYNSRVWKSO-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC)(C)C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC)(C)C IWOCHYNSRVWKSO-UHFFFAOYSA-N 0.000 claims 1
- MHRQDCKRJIRAFO-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC)C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC)C MHRQDCKRJIRAFO-UHFFFAOYSA-N 0.000 claims 1
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- SOVQSORWQGKPMK-UHFFFAOYSA-N O1CCC(C2=CC=CC=C12)C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC Chemical compound O1CCC(C2=CC=CC=C12)C(=O)N1CC2(C1)CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)OC SOVQSORWQGKPMK-UHFFFAOYSA-N 0.000 claims 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
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- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
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- 201000001421 hyperglycemia Diseases 0.000 claims 1
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- 210000004558 lewy body Anatomy 0.000 claims 1
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- 229940002612 prodrug Drugs 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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Classifications
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
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- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14160344 | 2014-03-17 | ||
| EP15710486.0A EP3119782B1 (en) | 2014-03-17 | 2015-03-17 | 2,7-diazaspiro[3.5]nonane compounds |
| PCT/EP2015/055494 WO2015140132A1 (en) | 2014-03-17 | 2015-03-17 | 2,7-diazaspiro[3.5]nonane compounds |
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|---|---|
| SI3119782T1 true SI3119782T1 (en) | 2018-06-29 |
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| SI201530219T SI3119782T1 (en) | 2014-03-17 | 2015-03-17 | COMPOUNDS 2,7-DIAZASPIRO (3.5) NONANA |
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| GB201416352D0 (en) | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
| GB201416351D0 (en) | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Heterocyclic derivatives |
| WO2019079410A1 (en) * | 2017-10-17 | 2019-04-25 | Vanderbilt University | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
| US11325896B2 (en) | 2017-12-20 | 2022-05-10 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| KR102694819B1 (ko) * | 2021-01-29 | 2024-08-14 | 한국화학연구원 | 벤조티아졸 및 벤즈이미다졸 유도체, 약제학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물 |
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| US20080247964A1 (en) * | 2006-05-08 | 2008-10-09 | Yuelian Xu | Substituted azaspiro derivatives |
| US20080070888A1 (en) | 2006-09-15 | 2008-03-20 | Mckittrick Brian A | Azetidine and azetidone derivatives useful in treating pain and disorders of lipid metabolism |
| ME02330B (me) * | 2010-03-19 | 2016-06-20 | Pfizer | Derivati 2,3-dihidro-1h-inden-1-il-2,7-diazaspir0[3.6]nonana i njihova upotreba kao antagonista ili inverznih agonista grelinskog receptora |
| EP2836482B1 (en) * | 2012-04-10 | 2019-12-25 | The Regents of The University of California | Compositions and methods for treating cancer |
| CN104364239B (zh) | 2012-06-13 | 2017-08-25 | 霍夫曼-拉罗奇有限公司 | 二氮杂螺环烷烃和氮杂螺环烷烃 |
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2019
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| NO3119782T3 (cg-RX-API-DMAC10.html) | 2018-06-30 |
| CA2941196A1 (en) | 2015-09-24 |
| JP6574438B2 (ja) | 2019-09-11 |
| EP3119782B1 (en) | 2018-01-31 |
| DK3119782T3 (en) | 2018-03-12 |
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| US9617264B2 (en) | 2017-04-11 |
| AU2015233642A1 (en) | 2016-09-08 |
| JP2019147834A (ja) | 2019-09-05 |
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| CN106103439A (zh) | 2016-11-09 |
| CA2941196C (en) | 2019-09-03 |
| EP3119782A1 (en) | 2017-01-25 |
| HRP20180585T1 (hr) | 2018-07-13 |
| AU2015233642B2 (en) | 2017-08-03 |
| JP2017507986A (ja) | 2017-03-23 |
| US20170157137A1 (en) | 2017-06-08 |
| PL3119782T3 (pl) | 2018-07-31 |
| ES2666173T3 (es) | 2018-05-03 |
| US20170015665A1 (en) | 2017-01-19 |
| PT3119782T (pt) | 2018-04-17 |
| EA201691539A1 (ru) | 2017-01-30 |
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