JP2013523636A5 - - Google Patents
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- Publication number
- JP2013523636A5 JP2013523636A5 JP2013501293A JP2013501293A JP2013523636A5 JP 2013523636 A5 JP2013523636 A5 JP 2013523636A5 JP 2013501293 A JP2013501293 A JP 2013501293A JP 2013501293 A JP2013501293 A JP 2013501293A JP 2013523636 A5 JP2013523636 A5 JP 2013523636A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- sulfonyl
- phenyl
- benzamide
- pyran
- 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.)
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 154
- -1 4′-chlorobiphenyl-2-yl Chemical group 0.000 claims description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 38
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- KXCQDIWJQBSUJF-UHFFFAOYSA-N 4-phenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1 KXCQDIWJQBSUJF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000651 prodrug Chemical class 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- QAFBPROQQSGNKK-UHFFFAOYSA-N 1-(1-adamantyl)-4-[2-[[4-[4-[[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylcarbamoyl]phenyl]piperazin-1-yl]methyl]phenyl]-n,n-diphenylpyrazole-3-carboxamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C(=NN(C=3)C34CC5CC(CC(C5)C3)C4)C(=O)N(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=CC=C1NCC1CCOCC1 QAFBPROQQSGNKK-UHFFFAOYSA-N 0.000 claims description 2
- LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 2
- KGQKHDAFBKFNHO-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-hydroxyphenyl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylnaphthalene-2-carboxamide Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(O)=CC=C1C(C=C1C=C2)=CC=C1C=C2C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCCCC1 KGQKHDAFBKFNHO-UHFFFAOYSA-N 0.000 claims description 2
- WTIWXNQNRBTBKY-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-methoxyphenyl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylnaphthalene-2-carboxamide Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1C(C=C1C=C2)=CC=C1C=C2C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCCCC1 WTIWXNQNRBTBKY-UHFFFAOYSA-N 0.000 claims description 2
- CHWWMJVEPPORKA-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)CNC2=C(C=C(C=C2)S(=O)(=O)NC(=O)C2=CC=C(C=C2)C=2C=CC3=C(N=C(S3)CCCC)C2)[N+](=O)[O-] Chemical compound C12(CC3CC(CC(C1)C3)C2)CNC2=C(C=C(C=C2)S(=O)(=O)NC(=O)C2=CC=C(C=C2)C=2C=CC3=C(N=C(S3)CCCC)C2)[N+](=O)[O-] CHWWMJVEPPORKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- YCGAILBJRWNKLY-UHFFFAOYSA-N n-[1-[4-[[3-nitro-4-(oxan-4-ylamino)phenyl]sulfonylcarbamoyl]phenyl]piperidin-4-yl]adamantane-1-carboxamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCC(CC2)NC(=O)C23CC4CC(CC(C4)C2)C3)=CC=C1NC1CCOCC1 YCGAILBJRWNKLY-UHFFFAOYSA-N 0.000 claims description 2
- AJZLLBZLGGUXKR-UHFFFAOYSA-N n-cyclooctyl-5-[2-[[4-[4-[[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylcarbamoyl]phenyl]piperazin-1-yl]methyl]phenyl]furan-2-carboxamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3OC(=CC=3)C(=O)NC3CCCCCCC3)CC2)=CC=C1NCC1CCOCC1 AJZLLBZLGGUXKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 6
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 6
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 6
- 201000000050 myeloid neoplasm Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 3
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 3
- 206010033128 Ovarian cancer Diseases 0.000 claims 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 3
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 206010041067 Small cell lung cancer Diseases 0.000 claims 3
- 208000000277 Splenic Neoplasms Diseases 0.000 claims 3
- 210000001744 T-lymphocyte Anatomy 0.000 claims 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 3
- 210000003719 b-lymphocyte Anatomy 0.000 claims 3
- 201000006491 bone marrow cancer Diseases 0.000 claims 3
- 201000010881 cervical cancer Diseases 0.000 claims 3
- 201000004101 esophageal cancer Diseases 0.000 claims 3
- 201000003444 follicular lymphoma Diseases 0.000 claims 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 3
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 3
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 3
- 208000003747 lymphoid leukemia Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 208000025113 myeloid leukemia Diseases 0.000 claims 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 3
- 201000002471 spleen cancer Diseases 0.000 claims 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 230000000527 lymphocytic effect Effects 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000004698 lymphocyte Anatomy 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- SAGLDTPKDYZPNX-UHFFFAOYSA-N oct-3-enamide Chemical compound CCCCC=CCC(N)=O SAGLDTPKDYZPNX-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 description 1
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 description 1
- 230000002424 anti-apoptotic effect Effects 0.000 description 1
- VMJGNWWGAXVEOP-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-4-carboxamide Chemical compound C1CC2C=CC1(C(=O)N)C2 VMJGNWWGAXVEOP-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31757510P | 2010-03-25 | 2010-03-25 | |
| US61/317,575 | 2010-03-25 | ||
| PCT/US2011/027895 WO2011119345A2 (en) | 2010-03-25 | 2011-03-10 | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013523636A JP2013523636A (ja) | 2013-06-17 |
| JP2013523636A5 true JP2013523636A5 (cg-RX-API-DMAC7.html) | 2016-06-16 |
| JP5959501B2 JP5959501B2 (ja) | 2016-08-02 |
Family
ID=43858249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501293A Expired - Fee Related JP5959501B2 (ja) | 2010-03-25 | 2011-03-10 | 癌ならびに免疫および自己免疫疾患の治療のためのアポトーシス誘導物質 |
Country Status (26)
Families Citing this family (33)
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| US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
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| TWI770925B (zh) * | 2017-05-26 | 2022-07-11 | 日商大鵬藥品工業股份有限公司 | 使用有新穎聯苯化合物之抗腫瘤效果增強劑 |
| GB201716871D0 (en) * | 2017-10-13 | 2017-11-29 | Inst Of Cancer Research: Royal Cancer Hospital | Compounds |
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| MX2011007681A (es) * | 2009-01-19 | 2011-08-08 | Abbott Lab | Agentes inducidores de apoptosis para el tratamiento del cancer y enfermedades inmunes y autoinmunes. |
| RU2538965C2 (ru) * | 2009-01-19 | 2015-01-10 | Эббви Инк. | Вызывающие апоптоз средства для лечения рака и иммунных и аутоиммунных заболеваний |
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2011
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