CZ9904452A3 - Cyklické acetaly imidazolylu, způsob jejich přípravy, jejich pouľití a farmaceutický prostředek, který je obsahuje - Google Patents

Info

Publication number

CZ9904452A3

CZ9904452A3 CZ19994452A CZ445299A CZ9904452A3 CZ 9904452 A3 CZ9904452 A3 CZ 9904452A3 CZ 19994452 A CZ19994452 A CZ 19994452A CZ 445299 A CZ445299 A CZ 445299A CZ 9904452 A3 CZ9904452 A3 CZ 9904452A3

Authority

CZ

Czechia

Prior art keywords

compound

fluorophenyl

imidazol

methyl

isomer

Prior art date

1997-06-12

Links

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• -1 Imidazolyl cyclic acetals Chemical class 0.000 title claims abstract description 732
• 238000000034 method Methods 0.000 title claims description 53
• 230000008569 process Effects 0.000 title claims description 20
• 238000002360 preparation method Methods 0.000 title claims description 8
• 150000001241 acetals Chemical class 0.000 title claims 3
• 239000000825 pharmaceutical preparation Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 1536
• 125000003118 aryl group Chemical group 0.000 claims abstract description 113
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 106
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 98
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 89
• 239000001257 hydrogen Substances 0.000 claims abstract description 89
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 69
• 150000003839 salts Chemical class 0.000 claims abstract description 56
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 54
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 50
• 229940002612 prodrug Drugs 0.000 claims abstract description 43
• 239000000651 prodrug Substances 0.000 claims abstract description 43
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 42
• 239000002253 acid Substances 0.000 claims abstract description 36
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 34
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 31
• 239000012453 solvate Substances 0.000 claims abstract description 29
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
• 150000004677 hydrates Chemical class 0.000 claims abstract description 23
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 13
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
• 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 12
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 10
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims abstract description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 6
• 239000003814 drug Substances 0.000 claims abstract description 6
• 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims abstract description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 774
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 758
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 254
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 54
• 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 claims description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 50
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 48
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 36
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 35
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 30
• 229910005965 SO 2 Inorganic materials 0.000 claims description 28
• 239000001301 oxygen Substances 0.000 claims description 28
• 150000001412 amines Chemical class 0.000 claims description 27
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 26
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 24
• 229920005989 resin Polymers 0.000 claims description 23
• 239000011347 resin Substances 0.000 claims description 23
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 239000004202 carbamide Substances 0.000 claims description 19
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 18
• 125000003277 amino group Chemical group 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 16
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 229940080818 propionamide Drugs 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• GSENCEDSCQYPIL-UHFFFAOYSA-N morpholin-4-ylmethanone Chemical compound O=[C]N1CCOCC1 GSENCEDSCQYPIL-UHFFFAOYSA-N 0.000 claims description 13
• 235000019260 propionic acid Nutrition 0.000 claims description 13
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
• 230000002378 acidificating effect Effects 0.000 claims description 11
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 8
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 6
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 6
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 150000007513 acids Chemical class 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• 150000004292 cyclic ethers Chemical class 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 5
• HILNBNGLDIFMAH-UHFFFAOYSA-N 1,3-dioxan-5-ylmethanol Chemical compound OCC1COCOC1 HILNBNGLDIFMAH-UHFFFAOYSA-N 0.000 claims description 4
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 4
• 229940126062 Compound A Drugs 0.000 claims description 4
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 125000005518 carboxamido group Chemical group 0.000 claims description 4
• JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims description 4
• 239000013256 coordination polymer Substances 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000006239 protecting group Chemical group 0.000 claims description 4
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 claims description 4
• BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 claims description 4
• IXTNDEVVXTYVHI-UHFFFAOYSA-N 1,4-dioxan-2-amine Chemical compound NC1COCCO1 IXTNDEVVXTYVHI-UHFFFAOYSA-N 0.000 claims description 3
• VGBAYGFELCUXBS-UHFFFAOYSA-N 1,4-dioxane-2-carboxylic acid Chemical compound OC(=O)C1COCCO1 VGBAYGFELCUXBS-UHFFFAOYSA-N 0.000 claims description 3
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 3
• IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 claims description 3
• CVNCZPNWIBTCHP-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-sulfonic acid Chemical compound CC1=NOC(C)=C1S(O)(=O)=O CVNCZPNWIBTCHP-UHFFFAOYSA-N 0.000 claims description 3
• COGSUIKHDYXIQL-UHFFFAOYSA-N 4-[2-(5,5-dimethyl-1,3-dioxan-2-yl)-4-(4-fluorophenyl)-1h-imidazol-5-yl]-2-(4-methylpiperazin-1-yl)pyrimidine Chemical compound C1CN(C)CCN1C1=NC=CC(C2=C(N=C(N2)C2OCC(C)(C)CO2)C=2C=CC(F)=CC=2)=N1 COGSUIKHDYXIQL-UHFFFAOYSA-N 0.000 claims description 3
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 229940125773 compound 10 Drugs 0.000 claims description 3
• ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims description 3
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 3
• IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 3
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 3
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 3
• FLKUFQSYLMDLMZ-UHFFFAOYSA-N n-(1,4-dioxan-2-ylmethyl)acetamide Chemical compound CC(=O)NCC1COCCO1 FLKUFQSYLMDLMZ-UHFFFAOYSA-N 0.000 claims description 3
• LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 3
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
• BLDLTMVNCFWBLW-UHFFFAOYSA-N pyrrolidin-1-ylmethanone Chemical compound O=[C]N1CCCC1 BLDLTMVNCFWBLW-UHFFFAOYSA-N 0.000 claims description 3
• OGFKTAMJLKHRAZ-UHFFFAOYSA-N 2,2-dimethoxyacetaldehyde Chemical compound COC(OC)C=O OGFKTAMJLKHRAZ-UHFFFAOYSA-N 0.000 claims description 2
• SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 claims description 2
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
• 239000005695 Ammonium acetate Substances 0.000 claims description 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
• 102000006835 Lamins Human genes 0.000 claims description 2
• 108010047294 Lamins Proteins 0.000 claims description 2
• WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
• 108010021119 Trichosanthin Proteins 0.000 claims description 2
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
• 235000019257 ammonium acetate Nutrition 0.000 claims description 2
• 229940043376 ammonium acetate Drugs 0.000 claims description 2
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 2
• MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims description 2
• 229940125890 compound Ia Drugs 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 claims description 2
• 208000018937 joint inflammation Diseases 0.000 claims description 2
• 210000005053 lamin Anatomy 0.000 claims description 2
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 2
• GHXAYCJYJUZRCP-UHFFFAOYSA-N n-butyl-2-[4-(4-fluorophenyl)-5-pyridin-4-yl-1h-imidazol-2-yl]-5-methyl-1,3-dioxane-5-carboxamide Chemical compound O1CC(C(=O)NCCCC)(C)COC1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N1 GHXAYCJYJUZRCP-UHFFFAOYSA-N 0.000 claims description 2
• YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• JYMQQKIMCZOSMX-UHFFFAOYSA-N thiomorpholine-4-carbaldehyde Chemical compound O=CN1CCSCC1 JYMQQKIMCZOSMX-UHFFFAOYSA-N 0.000 claims description 2
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 3
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