EA002114B1 - Новые ингибиторы фарнезилтрансферазы, способы их получения, содержащие их фармацевтические композиции и их применение для получения медикаментов - Google Patents

Info

Publication number

EA002114B1

EA002114B1 EA199900608A EA199900608A EA002114B1 EA 002114 B1 EA002114 B1 EA 002114B1 EA 199900608 A EA199900608 A EA 199900608A EA 199900608 A EA199900608 A EA 199900608A EA 002114 B1 EA002114 B1 EA 002114B1

Authority

EA

Eurasian Patent Office

Prior art keywords

isoindole

methoxyphenyl

ethano

benzo

propenoyl

Prior art date

1996-12-30

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 137
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 17
• 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title claims description 7
• 239000003814 drug Substances 0.000 title description 7
• -1 alkyl radical Chemical class 0.000 claims abstract description 402
• 150000001875 compounds Chemical class 0.000 claims abstract description 270
• 150000003254 radicals Chemical class 0.000 claims abstract description 117
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 113
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 111
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 64
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
• 239000001301 oxygen Substances 0.000 claims abstract description 38
• 125000005843 halogen group Chemical group 0.000 claims abstract description 34
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 33
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 26
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
• 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 abstract description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 16
• 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 15
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 14
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 13
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 12
• 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims abstract description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
• 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 abstract description 9
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 9
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 9
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 7
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 4
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
• 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract 2
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract 2
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
• 125000001544 thienyl group Chemical group 0.000 claims abstract 2
• WIXCPASTLDMTDB-UHFFFAOYSA-N isoindole-3a-carboxylic acid Chemical compound C1=CC=CC2(C(=O)O)C1=CN=C2 WIXCPASTLDMTDB-UHFFFAOYSA-N 0.000 claims description 342
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 324
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 119
• 150000004702 methyl esters Chemical class 0.000 claims description 97
• 125000003118 aryl group Chemical group 0.000 claims description 90
• 239000002253 acid Substances 0.000 claims description 86
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 58
• 239000011541 reaction mixture Substances 0.000 claims description 50
• 238000010992 reflux Methods 0.000 claims description 50
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 39
• 239000003960 organic solvent Substances 0.000 claims description 39
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
• 229910052717 sulfur Inorganic materials 0.000 claims description 36
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 33
• 238000002360 preparation method Methods 0.000 claims description 32
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 28
• 125000003277 amino group Chemical group 0.000 claims description 27
• 230000009471 action Effects 0.000 claims description 25
• 230000003287 optical effect Effects 0.000 claims description 25
• 125000006239 protecting group Chemical group 0.000 claims description 25
• 125000004434 sulfur atom Chemical group 0.000 claims description 23
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 19
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 18
• 230000015572 biosynthetic process Effects 0.000 claims description 18
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
• 239000011593 sulfur Chemical group 0.000 claims description 16
• 238000003786 synthesis reaction Methods 0.000 claims description 16
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 15
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 15
• 108010007508 Farnesyltranstransferase Proteins 0.000 claims description 14
• 102000007317 Farnesyltranstransferase Human genes 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• 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 13
• 206010028980 Neoplasm Diseases 0.000 claims description 13
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
• 229910052700 potassium Inorganic materials 0.000 claims description 12
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 10
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 10
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 10
• 150000008064 anhydrides Chemical class 0.000 claims description 10
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 10
• 230000004663 cell proliferation Effects 0.000 claims description 10
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 9
• CZTREFQQQAJNFV-UHFFFAOYSA-N 2h-isoindole-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)NC=C21 CZTREFQQQAJNFV-UHFFFAOYSA-N 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• XGQVCMLWPZDMEQ-UHFFFAOYSA-N N-hydroxyisoindole-3a-carboxamide Chemical compound C=1N=CC2(C=CC=CC=12)C(=O)NO XGQVCMLWPZDMEQ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 8
• 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 8
• 238000007127 saponification reaction Methods 0.000 claims description 8
• 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 239000002841 Lewis acid Substances 0.000 claims description 6
• 210000004027 cell Anatomy 0.000 claims description 6
• 210000001072 colon Anatomy 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 6
• 150000004820 halides Chemical class 0.000 claims description 6
• 150000007517 lewis acids Chemical class 0.000 claims description 6
• 229910052763 palladium Inorganic materials 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 239000012948 isocyanate Substances 0.000 claims description 5
• 150000002513 isocyanates Chemical class 0.000 claims description 5
• 210000004185 liver Anatomy 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 229940124226 Farnesyltransferase inhibitor Drugs 0.000 claims description 4
• 229910052786 argon Inorganic materials 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 230000005764 inhibitory process Effects 0.000 claims description 4
• GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical group IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 claims description 4
• IKAAQPYCYVBRPW-UHFFFAOYSA-N methyl isoindole-3a-carboxylate Chemical class C1=CC=CC2(C(=O)OC)C1=CN=C2 IKAAQPYCYVBRPW-UHFFFAOYSA-N 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 claims description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 238000006619 Stille reaction Methods 0.000 claims description 3
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
• 150000001543 aryl boronic acids Chemical class 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 150000002540 isothiocyanates Chemical class 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
• 210000001672 ovary Anatomy 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 210000001550 testis Anatomy 0.000 claims description 3
• 210000001519 tissue Anatomy 0.000 claims description 3
• 210000003932 urinary bladder Anatomy 0.000 claims description 3
• UCPDHOTYYDHPEN-OWOJBTEDSA-N (4e)-cyclooct-4-en-1-ol Chemical compound OC1CCC\C=C\CC1 UCPDHOTYYDHPEN-OWOJBTEDSA-N 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 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
• 238000006584 Barton reaction Methods 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• 201000009030 Carcinoma Diseases 0.000 claims description 2
• 208000006332 Choriocarcinoma Diseases 0.000 claims description 2
• 206010018338 Glioma Diseases 0.000 claims description 2
• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• 206010029260 Neuroblastoma Diseases 0.000 claims description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 208000008383 Wilms tumor Diseases 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 210000000988 bone and bone Anatomy 0.000 claims description 2
• 229910052796 boron Inorganic materials 0.000 claims description 2
• 208000006990 cholangiocarcinoma Diseases 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
• 230000001079 digestive effect Effects 0.000 claims description 2
• 230000006870 function Effects 0.000 claims description 2
• 210000004392 genitalia Anatomy 0.000 claims description 2
• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 230000001926 lymphatic effect Effects 0.000 claims description 2
• 210000004324 lymphatic system Anatomy 0.000 claims description 2
• 230000003211 malignant effect Effects 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 210000003205 muscle Anatomy 0.000 claims description 2
• 201000008026 nephroblastoma Diseases 0.000 claims description 2
• 210000000056 organ Anatomy 0.000 claims description 2
• 150000002900 organolithium compounds Chemical class 0.000 claims description 2
• 125000002734 organomagnesium group Chemical group 0.000 claims description 2
• 230000007170 pathology Effects 0.000 claims description 2
• 238000001959 radiotherapy Methods 0.000 claims description 2
• 210000005227 renal system Anatomy 0.000 claims description 2
• 210000003491 skin Anatomy 0.000 claims description 2
• 208000001608 teratocarcinoma Diseases 0.000 claims description 2
• DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
• 210000004698 lymphocyte Anatomy 0.000 claims 2
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
• 208000032612 Glial tumor Diseases 0.000 claims 1
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 210000000601 blood cell Anatomy 0.000 claims 1
• 229910052792 caesium Inorganic materials 0.000 claims 1
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 1
• 239000000945 filler Substances 0.000 claims 1
• 210000004907 gland Anatomy 0.000 claims 1
• 230000000527 lymphocytic effect Effects 0.000 claims 1
• 210000004216 mammary stem cell Anatomy 0.000 claims 1
• 239000011885 synergistic combination Substances 0.000 claims 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 14
• 150000003857 carboxamides Chemical class 0.000 abstract 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
• ACKHCMSNGJBQJU-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C5OCCOC5=CC=4)CC2)C3C1 ACKHCMSNGJBQJU-UHFFFAOYSA-N 0.000 abstract 1
• FMHQTPUKOSOOSZ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-11-[2-(2-methoxyphenyl)acetyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C(C)C(C)=CC=4)CC2)C3C1 FMHQTPUKOSOOSZ-UHFFFAOYSA-N 0.000 abstract 1
• OZABRLSRWAKWOC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-11-[2-(2-methoxyphenyl)acetyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC(C23C4=CC=CC=C4C(CC2)C2(C3CN(C2)C(=O)CC=2C(=CC=CC=2)OC)C(O)=O)=C1 OZABRLSRWAKWOC-UHFFFAOYSA-N 0.000 abstract 1
• LDHREUIOXSUSEW-UHFFFAOYSA-N 1-(4-fluorophenyl)-11-[2-(2-methoxyphenyl)acetyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(F)=CC=4)CC2)C3C1 LDHREUIOXSUSEW-UHFFFAOYSA-N 0.000 abstract 1
• JJYXSWJAGCGDOD-UHFFFAOYSA-N 1-(4-methoxyphenyl)-11-[2-(2-methoxyphenyl)acetyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C2CN(CC22C(O)=O)C(=O)CC=3C(=CC=CC=3)OC)C3=CC=CC=C3C2CC1 JJYXSWJAGCGDOD-UHFFFAOYSA-N 0.000 abstract 1
• VGJOCGVUHNTIMZ-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)acetyl]-1-(3,4,5-trimethylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C(C)C(C)=C(C)C=4)CC2)C3C1 VGJOCGVUHNTIMZ-UHFFFAOYSA-N 0.000 abstract 1
• LXRKXFHCZGPPHO-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)acetyl]-1-(3-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C(C)C=CC=4)CC2)C3C1 LXRKXFHCZGPPHO-UHFFFAOYSA-N 0.000 abstract 1
• RABKSVLBNLPPSM-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)acetyl]-1-(4-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 RABKSVLBNLPPSM-UHFFFAOYSA-N 0.000 abstract 1
• YLSYAFCBBIAWCF-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)acetyl]-1-(4-methylsulfanylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(SC)=CC=4)CC2)C3C1 YLSYAFCBBIAWCF-UHFFFAOYSA-N 0.000 abstract 1
• YHKLNWJNQGVQGC-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)prop-2-enoyl]-1-[4-(trifluoromethyl)phenyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(=CC=4)C(F)(F)F)CC2)C3C1 YHKLNWJNQGVQGC-UHFFFAOYSA-N 0.000 abstract 1
• AZLGWNUVZWBVDX-UHFFFAOYSA-N 11-[3-(2-methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C=CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 AZLGWNUVZWBVDX-UHFFFAOYSA-N 0.000 abstract 1
• JHSRBWGUFSDFKX-UHFFFAOYSA-N 6-(3,4-dihydro-2H-chromen-2-yl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=C1C=CC(=C2)C2OC1=C(CC2)C=CC=C1 JHSRBWGUFSDFKX-UHFFFAOYSA-N 0.000 abstract 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 1
• VNKZFVXPTIEJGQ-UHFFFAOYSA-N C(N)(=O)C12C3C4=C(C(C2CN(C1)C(C(=C)C1=C(C=CC=C1)OC)=O)(CC3)C1=CC=C(C=C1)C)C=CC=C4 Chemical compound C(N)(=O)C12C3C4=C(C(C2CN(C1)C(C(=C)C1=C(C=CC=C1)OC)=O)(CC3)C1=CC=C(C=C1)C)C=CC=C4 VNKZFVXPTIEJGQ-UHFFFAOYSA-N 0.000 abstract 1
• ASCZRXXOQQSSRX-UHFFFAOYSA-N C1CC(C=2C3=CC=CC=2)C2(C(=O)OC)CN(C(=O)C(=C)C=4C(=CC=CC=4)OC)CC2C31C1=CC=C(C)C=C1 Chemical compound C1CC(C=2C3=CC=CC=2)C2(C(=O)OC)CN(C(=O)C(=C)C=4C(=CC=CC=4)OC)CC2C31C1=CC=C(C)C=C1 ASCZRXXOQQSSRX-UHFFFAOYSA-N 0.000 abstract 1
• DJQYBWQXCIYTMK-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC2=CC=CC=C2C=C1)C=CC=C4)C(=O)OC)=C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC2=CC=CC=C2C=C1)C=CC=C4)C(=O)OC)=C DJQYBWQXCIYTMK-UHFFFAOYSA-N 0.000 abstract 1
• DSXFQDMNIKCFIJ-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C(F)(F)F)C=CC=C4)C(=O)OC)=C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C(F)(F)F)C=CC=C4)C(=O)OC)=C DSXFQDMNIKCFIJ-UHFFFAOYSA-N 0.000 abstract 1
• BGHJRLKETOBPQU-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C)C=CC=C4)C(=O)NOC)=C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C)C=CC=C4)C(=O)NOC)=C BGHJRLKETOBPQU-UHFFFAOYSA-N 0.000 abstract 1
• IRBVIQNGBDNNLD-UHFFFAOYSA-N COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C)C=CC=C4)C(=O)NOCC1=CC=CC=C1)=C Chemical compound COC1=C(C=CC=C1)C(C(=O)N1CC2(C3C4=C(C(C2C1)(CC3)C1=CC=C(C=C1)C)C=CC=C4)C(=O)NOCC1=CC=CC=C1)=C IRBVIQNGBDNNLD-UHFFFAOYSA-N 0.000 abstract 1
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