JP2013540119A5 - - Google Patents
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- JP2013540119A5 JP2013540119A5 JP2013530829A JP2013530829A JP2013540119A5 JP 2013540119 A5 JP2013540119 A5 JP 2013540119A5 JP 2013530829 A JP2013530829 A JP 2013530829A JP 2013530829 A JP2013530829 A JP 2013530829A JP 2013540119 A5 JP2013540119 A5 JP 2013540119A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- carbonyl
- spiro
- tetrahydro
- benzoic acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- -1 hydroxy, fluoro, phenyl Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- CROBEOGUJFDYPA-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-benzimidazol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=C2)=NC1=C2C1=CC=CC(C(O)=O)=C1 CROBEOGUJFDYPA-UHFFFAOYSA-N 0.000 claims 2
- HATGWLFXYOJZDJ-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=C2)=CC1=C2C1=CC=CC(C(O)=O)=C1 HATGWLFXYOJZDJ-UHFFFAOYSA-N 0.000 claims 2
- CGPLWVIRHVCYDM-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=NC=C2)=CC1=C2C1=CC=CC(C(O)=O)=C1 CGPLWVIRHVCYDM-UHFFFAOYSA-N 0.000 claims 2
- HXEJBKSDELCRJK-UHFFFAOYSA-N 3-[6-methoxy-4-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-2-yl]benzoic acid Chemical compound N=1C(OC)=CC(C(=O)N2CCC3(CC2)CC(=O)C=2N(C(C)C)N=CC=2C3)=CC=1C1=CC=CC(C(O)=O)=C1 HXEJBKSDELCRJK-UHFFFAOYSA-N 0.000 claims 2
- REPTXPNSUUKFMQ-UHFFFAOYSA-N 3-[6-oxo-4-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyridin-2-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(=CC(=O)N1)C=C1C1=CC=CC(C(O)=O)=C1 REPTXPNSUUKFMQ-UHFFFAOYSA-N 0.000 claims 2
- NMUDXSTWPJFVCN-UHFFFAOYSA-N 4-[6-(dimethylamino)-4-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-2-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=1)=CC(N(C)C)=NC=1C1=CC=C(C(O)=O)C=C1 NMUDXSTWPJFVCN-UHFFFAOYSA-N 0.000 claims 2
- PSBXMLBCZHXXRZ-UHFFFAOYSA-N 4-[[4-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)phenoxy]methyl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1)=CC=C1OCC1=CC=C(C(O)=O)C=C1 PSBXMLBCZHXXRZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 229940125708 antidiabetic agent Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229960004580 glibenclamide Drugs 0.000 claims 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims 1
- GQPZAWWEJRPKBC-UHFFFAOYSA-N 1-propan-2-yl-1'-[4-[3-(2h-tetrazol-5-yl)phenyl]benzoyl]spiro[4,6-dihydroindazole-5,4'-piperidine]-7-one Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C(C=1)=CC=CC=1C1=NN=NN1 GQPZAWWEJRPKBC-UHFFFAOYSA-N 0.000 claims 1
- VCQDLEYFWQYIRF-UHFFFAOYSA-N 1-tert-butyl-1'-[4-[3-(2h-tetrazol-5-yl)phenyl]benzoyl]spiro[4,6-dihydroindazole-5,4'-piperidine]-7-one Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C(C=1)=CC=CC=1C1=NN=NN1 VCQDLEYFWQYIRF-UHFFFAOYSA-N 0.000 claims 1
- SQGNBGAYPGECDT-UHFFFAOYSA-N 2-[2-methoxy-5-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]phenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(OC)=CC=C1C1=CC=CC2=C1C=C(C(=O)N1CCC3(CC1)CC(=O)C=1N(C(C)C)N=CC=1C3)N2 SQGNBGAYPGECDT-UHFFFAOYSA-N 0.000 claims 1
- DIEOLUPIWBVGPD-UHFFFAOYSA-N 3-(1,3-oxazol-2-yl)-5-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=1)=CC(C(O)=O)=CC=1C1=NC=CO1 DIEOLUPIWBVGPD-UHFFFAOYSA-N 0.000 claims 1
- CUPARKJNRPBOAC-UHFFFAOYSA-N 3-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-5-(1,3-oxazol-2-yl)benzoic acid Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=1)=CC(C(O)=O)=CC=1C1=NC=CO1 CUPARKJNRPBOAC-UHFFFAOYSA-N 0.000 claims 1
- LHHYGFACCLSIRS-UHFFFAOYSA-N 3-[2-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=C2)=CC1=C2C1=CC=CC(C(O)=O)=C1 LHHYGFACCLSIRS-UHFFFAOYSA-N 0.000 claims 1
- FRIOVTCXANEONN-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-6-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=C2)=CC1=CC=C2C1=CC=CC(C(O)=O)=C1 FRIOVTCXANEONN-UHFFFAOYSA-N 0.000 claims 1
- WECUJSSWTZPGDL-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[2,3-c]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CN=C2)=CC1=C2C1=CC=CC(C(O)=O)=C1 WECUJSSWTZPGDL-UHFFFAOYSA-N 0.000 claims 1
- OYTBONCRVYVFRS-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[3,2-c]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=N2)=CC1=C2C1=CC=CC(C(O)=O)=C1 OYTBONCRVYVFRS-UHFFFAOYSA-N 0.000 claims 1
- GFGJQKQIDINRPX-UHFFFAOYSA-N 3-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-3h-benzimidazol-5-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=2)=NC1=CC=2C1=CC=CC(C(O)=O)=C1 GFGJQKQIDINRPX-UHFFFAOYSA-N 0.000 claims 1
- KMDKGZWGKLAZSW-UHFFFAOYSA-N 3-[4-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-6-methoxypyridin-2-yl]benzoic acid Chemical compound N=1C(OC)=CC(C(=O)N2CCC3(CC2)CC(=O)C=2N(N=CC=2C3)C(C)(C)C)=CC=1C1=CC=CC(C(O)=O)=C1 KMDKGZWGKLAZSW-UHFFFAOYSA-N 0.000 claims 1
- RUSHODREPMAKFT-UHFFFAOYSA-N 3-[4-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)phenyl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C1=CC=CC(C(O)=O)=C1 RUSHODREPMAKFT-UHFFFAOYSA-N 0.000 claims 1
- GZOSFBCGVXPKAL-UHFFFAOYSA-N 3-[4-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)phenyl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C1=CC=CC(C(O)=O)=C1 GZOSFBCGVXPKAL-UHFFFAOYSA-N 0.000 claims 1
- NQFXZBLVPWGBEQ-UHFFFAOYSA-N 3-[5-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-6-(ethylamino)pyridin-2-yl]benzoic acid Chemical compound C=1C=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(N=CC=2C3)C(C)(C)C)C(NCC)=NC=1C1=CC=CC(C(O)=O)=C1 NQFXZBLVPWGBEQ-UHFFFAOYSA-N 0.000 claims 1
- ASMSFMZFSITJMS-UHFFFAOYSA-N 3-[5-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-6-(methylamino)pyridin-2-yl]benzoic acid Chemical compound C=1C=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(N=CC=2C3)C(C)(C)C)C(NC)=NC=1C1=CC=CC(C(O)=O)=C1 ASMSFMZFSITJMS-UHFFFAOYSA-N 0.000 claims 1
- MRDCPTCBCJUGJZ-UHFFFAOYSA-N 3-[5-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-6-(propan-2-ylamino)pyridin-2-yl]benzoic acid Chemical compound C=1C=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(C(C)C)N=CC=2C3)C(NC(C)C)=NC=1C1=CC=CC(C(O)=O)=C1 MRDCPTCBCJUGJZ-UHFFFAOYSA-N 0.000 claims 1
- HTSATYCBQUXNDH-UHFFFAOYSA-N 3-[6-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=C1NC=CC1=1)=CC=1C1=CC=CC(C(O)=O)=C1 HTSATYCBQUXNDH-UHFFFAOYSA-N 0.000 claims 1
- DXAYBSGJUCJQIV-UHFFFAOYSA-N 3-[6-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=NC=N2)=CC1=C2C1=CC=CC(C(O)=O)=C1 DXAYBSGJUCJQIV-UHFFFAOYSA-N 0.000 claims 1
- OWCFADICMXYNHA-UHFFFAOYSA-N 3-[6-(dimethylamino)-4-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-2-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(C=1)=CC(N(C)C)=NC=1C1=CC=CC(C(O)=O)=C1 OWCFADICMXYNHA-UHFFFAOYSA-N 0.000 claims 1
- VOXNMQIQGVOHTP-UHFFFAOYSA-N 3-[6-(ethylamino)-5-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-2-yl]benzoic acid Chemical compound C=1C=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(C(C)C)N=CC=2C3)C(NCC)=NC=1C1=CC=CC(C(O)=O)=C1 VOXNMQIQGVOHTP-UHFFFAOYSA-N 0.000 claims 1
- KHNSXXJIOZMVSR-UHFFFAOYSA-N 3-[6-(methylamino)-5-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-2-yl]benzoic acid Chemical compound C=1C=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(C(C)C)N=CC=2C3)C(NC)=NC=1C1=CC=CC(C(O)=O)=C1 KHNSXXJIOZMVSR-UHFFFAOYSA-N 0.000 claims 1
- VVRKTWHMLVQLSX-UHFFFAOYSA-N 3-[6-(methylamino)-5-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)pyridin-3-yl]benzoic acid Chemical compound C1=C(C(=O)N2CCC3(CC2)CC(=O)C=2N(C(C)C)N=CC=2C3)C(NC)=NC=C1C1=CC=CC(C(O)=O)=C1 VVRKTWHMLVQLSX-UHFFFAOYSA-N 0.000 claims 1
- LMLWDHXQEFSYIS-UHFFFAOYSA-N 4-[2-(1-tert-butyl-7-oxospiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=C2)=CC1=C2C1=CC=C(C(O)=O)C=C1 LMLWDHXQEFSYIS-UHFFFAOYSA-N 0.000 claims 1
- CJXBPTFRHOUSQA-UHFFFAOYSA-N 4-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-indol-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=C2)=CC1=C2C1=CC=C(C(O)=O)C=C1 CJXBPTFRHOUSQA-UHFFFAOYSA-N 0.000 claims 1
- VKIQXEPHWQUFNJ-UHFFFAOYSA-N 4-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=NC=C2)=CC1=C2C1=CC=C(C(O)=O)C=C1 VKIQXEPHWQUFNJ-UHFFFAOYSA-N 0.000 claims 1
- OIKUWZYIYYRWSF-UHFFFAOYSA-N 4-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[2,3-c]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CN=C2)=CC1=C2C1=CC=C(C(O)=O)C=C1 OIKUWZYIYYRWSF-UHFFFAOYSA-N 0.000 claims 1
- OSZRMXOUTAIXDP-UHFFFAOYSA-N 4-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-1h-pyrrolo[3,2-c]pyridin-4-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=N2)=CC1=C2C1=CC=C(C(O)=O)C=C1 OSZRMXOUTAIXDP-UHFFFAOYSA-N 0.000 claims 1
- TXFRLVBIQLXQJL-UHFFFAOYSA-N 4-[2-(7-oxo-1-propan-2-ylspiro[4,6-dihydroindazole-5,4'-piperidine]-1'-carbonyl)-3h-benzimidazol-5-yl]benzoic acid Chemical compound C1C(=O)C=2N(C(C)C)N=CC=2CC1(CC1)CCN1C(=O)C(NC1=CC=2)=NC1=CC=2C1=CC=C(C(O)=O)C=C1 TXFRLVBIQLXQJL-UHFFFAOYSA-N 0.000 claims 1
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| RS (1) | RS55224B1 (enExample) |
| SI (1) | SI2621493T1 (enExample) |
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| KR20220112811A (ko) | 2019-12-10 | 2022-08-11 | 화이자 인코포레이티드 | 2-((4-((S)-2-(5-클로로피리딘-2-일)-2-메틸벤조[d][1,3]디옥솔-4-일)피페리딘-1-일)메틸)-1-(((S)-옥세탄-2-일)메틸)-1H-벤조[d]이미다졸-6-카르복실산, 1,3-디히드록시-2-(히드록시메틸)프로판-2-아민 염의 고체 형태 |
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| US20160034775A1 (en) | 2014-08-02 | 2016-02-04 | General Vault, LLC | Methods and apparatus for bounded image data analysis and notification mechanism |
-
2011
- 2011-09-20 PT PT117681635T patent/PT2621493T/pt unknown
- 2011-09-20 LT LTEP11768163.5T patent/LT2621493T/lt unknown
- 2011-09-20 ES ES11768163.5T patent/ES2602111T3/es active Active
- 2011-09-20 PL PL11768163T patent/PL2621493T3/pl unknown
- 2011-09-20 CA CA2811033A patent/CA2811033C/en active Active
- 2011-09-20 HU HUE11768163A patent/HUE031616T2/hu unknown
- 2011-09-20 DK DK11768163.5T patent/DK2621493T3/en active
- 2011-09-20 HR HRP20161178TT patent/HRP20161178T1/hr unknown
- 2011-09-20 JP JP2013530829A patent/JP5824055B2/ja active Active
- 2011-09-20 EP EP11768163.5A patent/EP2621493B1/en active Active
- 2011-09-20 RS RS20160845A patent/RS55224B1/sr unknown
- 2011-09-20 US US13/876,211 patent/US8859577B2/en active Active
- 2011-09-20 SI SI201130951A patent/SI2621493T1/sl unknown
- 2011-09-20 WO PCT/IB2011/054119 patent/WO2012042433A1/en not_active Ceased
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2014
- 2014-09-19 US US14/491,016 patent/US9145416B2/en active Active
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2015
- 2015-09-11 US US14/851,572 patent/US20150376185A1/en not_active Abandoned
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2016
- 2016-08-15 US US15/236,635 patent/US9908883B2/en active Active
- 2016-09-13 CY CY20161100905T patent/CY1118016T1/el unknown
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2018
- 2018-01-30 US US15/883,109 patent/US10294225B2/en active Active
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2019
- 2019-04-01 US US16/371,896 patent/US10822335B2/en active Active
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2020
- 2020-09-28 US US17/034,295 patent/US11673890B2/en active Active
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2023
- 2023-05-03 US US18/311,715 patent/US20230322777A1/en not_active Abandoned
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