CA2762174C - N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors - Google Patents

Info

Publication number

CA2762174C

CA2762174C CA2762174A CA2762174A CA2762174C CA 2762174 C CA2762174 C CA 2762174C CA 2762174 A CA2762174 A CA 2762174A CA 2762174 A CA2762174 A CA 2762174A CA 2762174 C CA2762174 C CA 2762174C

Authority

CA

Canada

Prior art keywords

pyrimidin

pyrrolo

pyridin

pyrrolidin

pyrazol

Prior art date

2009-05-22

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.)

Active

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 26
• PSJGZWCZKPCRFZ-UHFFFAOYSA-N 2-(1h-pyrrol-3-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical class N1C2=NC=CC2=CN=C1C=1C=CNC=1 PSJGZWCZKPCRFZ-UHFFFAOYSA-N 0.000 title description 2
• -1 nitro, hydroxyl Chemical group 0.000 claims description 513
• 150000001875 compounds Chemical class 0.000 claims description 256
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 135
• 125000001153 fluoro group Chemical group F* 0.000 claims description 126
• 150000003839 salts Chemical class 0.000 claims description 125
• 125000000217 alkyl group Chemical group 0.000 claims description 124
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 115
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 95
• 150000001204 N-oxides Chemical class 0.000 claims description 91
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 91
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 84
• 125000001072 heteroaryl group Chemical group 0.000 claims description 82
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 59
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 59
• 229910052736 halogen Chemical group 0.000 claims description 57
• 150000002367 halogens Chemical group 0.000 claims description 57
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
• 125000002619 bicyclic group Chemical group 0.000 claims description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
• 125000003282 alkyl amino group Chemical group 0.000 claims description 46
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 45
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 40
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 39
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 37
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 36
• 125000001188 haloalkyl group Chemical group 0.000 claims description 34
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 31
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 27
• 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 27
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 27
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 27
• 125000001246 bromo group Chemical group Br* 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims description 23
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 22
• 125000004414 alkyl thio group Chemical group 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims description 18
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 17
• 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 17
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 16
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 16
• BRIOKNPDCPJCOD-UHFFFAOYSA-N [1,3]oxazolo[5,4-d]pyrimidine Chemical group N1=CN=C2OC=NC2=C1 BRIOKNPDCPJCOD-UHFFFAOYSA-N 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical group C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims description 15
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 13
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 12
• SXHIAOQRZREZPE-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b]pyridine Chemical group C1=CN=C2SCCC2=C1 SXHIAOQRZREZPE-UHFFFAOYSA-N 0.000 claims description 12
• QZWLBQZGTDOYGZ-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b]pyridine 1-oxide Chemical group C1=CN=C2S(=O)CCC2=C1 QZWLBQZGTDOYGZ-UHFFFAOYSA-N 0.000 claims description 12
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 12
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical group N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 12
• ZATXVRSLQDRAHZ-UHFFFAOYSA-N [1,3]oxazolo[4,5-c]pyridine Chemical group N1=CC=C2OC=NC2=C1 ZATXVRSLQDRAHZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical group C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 9
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 9
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 9
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical group OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• QNNHQVPFZIFNFK-UHFFFAOYSA-N oxazolo[4,5-b]pyridine Chemical group C1=CC=C2OC=NC2=N1 QNNHQVPFZIFNFK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• IFMHNXABCSMTFF-UHFFFAOYSA-N 2,3-dihydrofuro[2,3-b]pyridine Chemical group C1=CN=C2OCCC2=C1 IFMHNXABCSMTFF-UHFFFAOYSA-N 0.000 claims description 4
• ZKOUDBLKNQABQO-UHFFFAOYSA-N 2,3-dihydrothieno[3,2-c]pyridine Chemical group N1=CC=C2SCCC2=C1 ZKOUDBLKNQABQO-UHFFFAOYSA-N 0.000 claims description 4
• CXZHPADESZBJNS-UHFFFAOYSA-N 2,3-dihydrothieno[3,2-c]pyridine 1-oxide Chemical group N1=CC=C2S(=O)CCC2=C1 CXZHPADESZBJNS-UHFFFAOYSA-N 0.000 claims description 4
• KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical group C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 claims description 4
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• CDGFEINVQHEUQV-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine Chemical group N1=CN=C2SC=NC2=C1 CDGFEINVQHEUQV-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical group N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical group C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 claims description 4
• GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical group C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 claims description 4
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical group C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims description 4
• MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical group N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims description 4
• JSLBLMYJYPZTEB-UHFFFAOYSA-N thiophene-3,4-dicarbonitrile Chemical compound N#CC1=CSC=C1C#N JSLBLMYJYPZTEB-UHFFFAOYSA-N 0.000 claims description 4
• SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical group N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 claims description 3
• XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 3
• 229920006391 phthalonitrile polymer Polymers 0.000 claims description 3
• VTHCULBLEKIUTL-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC1=[C]SC=C1 VTHCULBLEKIUTL-UHFFFAOYSA-N 0.000 claims description 3
• DMMAUIBOZBZOQD-UHFFFAOYSA-N 4-[1-[1-[1-(3,5-difluoro-6-methylsulfonylpyridin-2-yl)pyrrolidin-3-yl]-2-fluoroethyl]pyrazol-4-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=C(F)C(S(=O)(=O)C)=NC(N2CC(CC2)C(CF)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1F DMMAUIBOZBZOQD-UHFFFAOYSA-N 0.000 claims description 2
• 150000003016 phosphoric acids Chemical class 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• QYCIXUKZMDUDBK-UHFFFAOYSA-N thieno[3,2-b]pyridine-6-carbonitrile Chemical compound N#CC1=CN=C2C=CSC2=C1 QYCIXUKZMDUDBK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 19
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
• KFMWVLNEOUSBLY-UHFFFAOYSA-N 2-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-[1,3]oxazolo[5,4-b]pyridine Chemical compound C1CN(C=2OC3=NC=CC=C3N=2)CC1C(CF)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 KFMWVLNEOUSBLY-UHFFFAOYSA-N 0.000 claims 2
• UHPOZFYNJIMRCT-UHFFFAOYSA-N 3-[1-(6-chloropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 UHPOZFYNJIMRCT-UHFFFAOYSA-N 0.000 claims 2
• 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims 2
• UHPOZFYNJIMRCT-FBMWCMRBSA-N (3r)-3-[1-(6-chloropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CC=CC(N2CC(CC2)[C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 UHPOZFYNJIMRCT-FBMWCMRBSA-N 0.000 claims 1
• UHPOZFYNJIMRCT-JRZJBTRGSA-N (3s)-3-[1-(6-chloropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CC=CC(N2CC(CC2)[C@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 UHPOZFYNJIMRCT-JRZJBTRGSA-N 0.000 claims 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• KIHLJOWZBITKOC-UWBLVGDVSA-N 2-[3-[(1r)-2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]thiophene-3,4-dicarbonitrile Chemical compound C1C([C@H](CF)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCN1C=1SC=C(C#N)C=1C#N KIHLJOWZBITKOC-UWBLVGDVSA-N 0.000 claims 1
• RKBMMTKBMKXEMF-UHFFFAOYSA-N 2-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-3-carbonitrile Chemical compound C1=CC(C=2C=3C=CNC=3N=CN=2)=CN1C(CC#N)C(C1)CCN1C1=NC=CC=C1C#N RKBMMTKBMKXEMF-UHFFFAOYSA-N 0.000 claims 1
• UIOGVMWDFMKNSC-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-1,3-benzoxazole-7-carbonitrile Chemical compound C1CN(C=2OC3=C(C#N)C=CC=C3N=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 UIOGVMWDFMKNSC-UHFFFAOYSA-N 0.000 claims 1
• GNCBHSQTXDAMHN-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-3,5,6-trifluorobenzonitrile Chemical compound N#CC1=C(F)C(F)=CC(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 GNCBHSQTXDAMHN-UHFFFAOYSA-N 0.000 claims 1
• OALXWMRSUWYVKP-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 OALXWMRSUWYVKP-UHFFFAOYSA-N 0.000 claims 1
• KYACQCQAJNIFNK-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-(1-fluoroethyl)pyridine-3-carbonitrile Chemical compound CC(F)C1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N KYACQCQAJNIFNK-UHFFFAOYSA-N 0.000 claims 1
• LMKCSQZLWZQQAJ-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-(difluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)C1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N LMKCSQZLWZQQAJ-UHFFFAOYSA-N 0.000 claims 1
• FNGSNCZNWJGJMR-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-(methoxymethyl)pyridine-3-carbonitrile Chemical compound COCC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N FNGSNCZNWJGJMR-UHFFFAOYSA-N 0.000 claims 1
• QUZILCRIIZSKQV-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N QUZILCRIIZSKQV-UHFFFAOYSA-N 0.000 claims 1
• FCQVGDGOPQOVII-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-iodopyridine-3-carbonitrile Chemical compound IC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N FCQVGDGOPQOVII-UHFFFAOYSA-N 0.000 claims 1
• QAJQMIQYOPKRDM-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N QAJQMIQYOPKRDM-UHFFFAOYSA-N 0.000 claims 1
• MSTYDYFFTNLCGO-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-methylsulfanylpyridine-3-carbonitrile Chemical compound CSC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N MSTYDYFFTNLCGO-UHFFFAOYSA-N 0.000 claims 1
• RUBICEJGXZPAAU-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-4-methylsulfonylpyridine-3-carbonitrile Chemical compound CS(=O)(=O)C1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N RUBICEJGXZPAAU-UHFFFAOYSA-N 0.000 claims 1
• UKUSHZACMONQCF-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-fluoro-4-(methoxymethyl)pyridine-3-carbonitrile Chemical compound COCC1=C(F)C=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N UKUSHZACMONQCF-UHFFFAOYSA-N 0.000 claims 1
• ZWNYDPIBEUUJAC-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-fluoropyridine-3-carbonitrile Chemical compound N#CC1=CC(F)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 ZWNYDPIBEUUJAC-UHFFFAOYSA-N 0.000 claims 1
• PWOOGVSPOMVTPF-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-methylpyridine-3-carbonitrile Chemical compound N#CC1=CC(C)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 PWOOGVSPOMVTPF-UHFFFAOYSA-N 0.000 claims 1
• IXWUEGIYHZPFFQ-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(difluoromethyl)benzonitrile Chemical compound FC(F)C1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N IXWUEGIYHZPFFQ-UHFFFAOYSA-N 0.000 claims 1
• JDSKVGOCQLVSPU-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(methoxymethyl)benzonitrile Chemical compound COCC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N JDSKVGOCQLVSPU-UHFFFAOYSA-N 0.000 claims 1
• MCWCUEXWQUWBCY-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-fluorobenzonitrile Chemical compound FC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N MCWCUEXWQUWBCY-UHFFFAOYSA-N 0.000 claims 1
• MBMJSQMRGWKPFW-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methoxybenzonitrile Chemical compound COC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N MBMJSQMRGWKPFW-UHFFFAOYSA-N 0.000 claims 1
• ANSWPRCUJQLHSX-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methylbenzonitrile Chemical compound CC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N ANSWPRCUJQLHSX-UHFFFAOYSA-N 0.000 claims 1
• SJZHZLMYFVEVNE-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methylsulfanylbenzonitrile Chemical compound CSC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N SJZHZLMYFVEVNE-UHFFFAOYSA-N 0.000 claims 1
• LTHRWSRYCKLPPM-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methylsulfonylbenzonitrile Chemical compound CS(=O)(=O)C1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N LTHRWSRYCKLPPM-UHFFFAOYSA-N 0.000 claims 1
• OSDLWCSNZQGJSS-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]benzene-1,3-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=C(C#N)C=CC=C1C#N OSDLWCSNZQGJSS-UHFFFAOYSA-N 0.000 claims 1
• LUCHRRRQSFVVCZ-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]benzonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=CC=CC=C1C#N LUCHRRRQSFVVCZ-UHFFFAOYSA-N 0.000 claims 1
• NSYUGYDLXNVCAM-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-3,4-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=NC=CC(C#N)=C1C#N NSYUGYDLXNVCAM-UHFFFAOYSA-N 0.000 claims 1
• DYLLYBHKZHTFET-UHFFFAOYSA-N 2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]thiophene-3,4-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C=1SC=C(C#N)C=1C#N DYLLYBHKZHTFET-UHFFFAOYSA-N 0.000 claims 1
• QRRUCSZEQJAENX-UHFFFAOYSA-N 2-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-3,4-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CF)C(C1)CCN1C1=NC=CC(C#N)=C1C#N QRRUCSZEQJAENX-UHFFFAOYSA-N 0.000 claims 1
• HBWAJXUKIDRYJM-UHFFFAOYSA-N 2-bromo-6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]benzonitrile Chemical compound BrC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N HBWAJXUKIDRYJM-UHFFFAOYSA-N 0.000 claims 1
• MUTNHJHEEGNVRP-UHFFFAOYSA-N 2-chloro-4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-3-carbonitrile Chemical compound ClC1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N MUTNHJHEEGNVRP-UHFFFAOYSA-N 0.000 claims 1
• QKGNQDLTGHUEGQ-UHFFFAOYSA-N 2-chloro-6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-fluoropyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=C(Cl)N=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 QKGNQDLTGHUEGQ-UHFFFAOYSA-N 0.000 claims 1
• BKUZTJNOISYCFG-UHFFFAOYSA-N 2-chloro-6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]benzonitrile Chemical compound ClC1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N BKUZTJNOISYCFG-UHFFFAOYSA-N 0.000 claims 1
• WHLQTZNFTNEYGS-UHFFFAOYSA-N 2-chloro-6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 WHLQTZNFTNEYGS-UHFFFAOYSA-N 0.000 claims 1
• CMWWMTPSKMZFNB-UHFFFAOYSA-N 3-[1-(1,1-dioxo-2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]propanenitrile Chemical compound N1=C2S(=O)(=O)CCC2=CC=C1N(C1)CCC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 CMWWMTPSKMZFNB-UHFFFAOYSA-N 0.000 claims 1
• UIPFNBCICNUXPY-UHFFFAOYSA-N 3-[1-(1,1-dioxo-2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2S(=O)(=O)CCC2=CC=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 UIPFNBCICNUXPY-UHFFFAOYSA-N 0.000 claims 1
• SFIMAOUYSHYVFJ-UHFFFAOYSA-N 3-[1-(1-oxo-2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]propanenitrile Chemical compound N1=C2S(=O)CCC2=CC=C1N(C1)CCC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 SFIMAOUYSHYVFJ-UHFFFAOYSA-N 0.000 claims 1
• UCCHJUZKODRKFF-UHFFFAOYSA-N 3-[1-(1-oxo-2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2S(=O)CCC2=CC=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 UCCHJUZKODRKFF-UHFFFAOYSA-N 0.000 claims 1
• NHGOKCYNPHBVBP-UHFFFAOYSA-N 3-[1-(2,3-dihydrofuro[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C=2N=C3OCCC3=CC=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 NHGOKCYNPHBVBP-UHFFFAOYSA-N 0.000 claims 1
• FOVAFCLLQLJVAY-UHFFFAOYSA-N 3-[1-(2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C=2N=C3SCCC3=CC=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 FOVAFCLLQLJVAY-UHFFFAOYSA-N 0.000 claims 1
• NCCQRELASOGLOO-UHFFFAOYSA-N 3-[1-(2,5-difluoro-6-methylsulfonylpyridin-3-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(F)C(S(=O)(=O)C)=NC(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 NCCQRELASOGLOO-UHFFFAOYSA-N 0.000 claims 1
• GWDSJXAVSSYRNL-UHFFFAOYSA-N 3-[1-(2,6-dichloropyridin-3-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=NC(Cl)=CC=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 GWDSJXAVSSYRNL-UHFFFAOYSA-N 0.000 claims 1
• GZRQEPIQNZHSSB-UHFFFAOYSA-N 3-[1-(2-chloropyrimidin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 GZRQEPIQNZHSSB-UHFFFAOYSA-N 0.000 claims 1
• GUKHLLHCNUOLHV-UHFFFAOYSA-N 3-[1-(2-ethylsulfonylpyridin-4-yl)pyrrolidin-3-yl]-3-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]propanenitrile Chemical compound C1=NC(S(=O)(=O)CC)=CC(N2CC(CC2)C(CC#N)N2C=C(C=C2)C=2C=3C=CNC=3N=CN=2)=C1 GUKHLLHCNUOLHV-UHFFFAOYSA-N 0.000 claims 1
• WQOQGIKZBVECIY-UHFFFAOYSA-N 3-[1-(2-methylsulfanylpyrimidin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CSC1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 WQOQGIKZBVECIY-UHFFFAOYSA-N 0.000 claims 1
• VAEQPOSTKHPUFW-UHFFFAOYSA-N 3-[1-(2-methylsulfinylpyrimidin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CS(=O)C1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 VAEQPOSTKHPUFW-UHFFFAOYSA-N 0.000 claims 1
• DAIPAUVXCAIJNO-UHFFFAOYSA-N 3-[1-(2-methylsulfonylpyridin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NC(S(=O)(=O)C)=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 DAIPAUVXCAIJNO-UHFFFAOYSA-N 0.000 claims 1
• OXIMQCNTOQPNGE-UHFFFAOYSA-N 3-[1-(2-methylsulfonylpyrimidin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CS(=O)(=O)C1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 OXIMQCNTOQPNGE-UHFFFAOYSA-N 0.000 claims 1
• LLDIOYKDWSDNRD-UHFFFAOYSA-N 3-[1-(3,5-difluoro-6-methylsulfanylpyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(F)C(SC)=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1F LLDIOYKDWSDNRD-UHFFFAOYSA-N 0.000 claims 1
• BUHJWJFWPBQZGE-UHFFFAOYSA-N 3-[1-(3,5-difluoro-6-methylsulfonylpyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(F)C(S(=O)(=O)C)=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1F BUHJWJFWPBQZGE-UHFFFAOYSA-N 0.000 claims 1
• WTEOPCFHTUICKO-UHFFFAOYSA-N 3-[1-(3-amino-6-chloropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound NC1=CC=C(Cl)N=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 WTEOPCFHTUICKO-UHFFFAOYSA-N 0.000 claims 1
• OHJFRGOQFNEILV-UHFFFAOYSA-N 3-[1-(3-fluoro-6-methylsulfonylpyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CS(=O)(=O)C1=CC=C(F)C(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 OHJFRGOQFNEILV-UHFFFAOYSA-N 0.000 claims 1
• JILOKNACMWKRMA-UHFFFAOYSA-N 3-[1-(3-oxo-4h-quinoxalin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound OC1=NC2=CC=CC=C2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 JILOKNACMWKRMA-UHFFFAOYSA-N 0.000 claims 1
• LOPLNQIRVMZBAF-UHFFFAOYSA-N 3-[1-(4-bromo-1,3-thiazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound BrC1=CSC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 LOPLNQIRVMZBAF-UHFFFAOYSA-N 0.000 claims 1
• TVCIBTZXCQYBFK-UHFFFAOYSA-N 3-[1-(4-chloropyrimidin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 TVCIBTZXCQYBFK-UHFFFAOYSA-N 0.000 claims 1
• OWDDRSWHPOXORO-UHFFFAOYSA-N 3-[1-(4-fluoro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C=2C(F)=CC=CC=2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 OWDDRSWHPOXORO-UHFFFAOYSA-N 0.000 claims 1
• DPWMUGJLHUDFPX-UHFFFAOYSA-N 3-[1-(4-hydroxy-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C=2C(O)=CC=CC=2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DPWMUGJLHUDFPX-UHFFFAOYSA-N 0.000 claims 1
• NUXDAQZWXURREX-UHFFFAOYSA-N 3-[1-(4-methyl-3-oxopyrazin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O=C1N(C)C=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 NUXDAQZWXURREX-UHFFFAOYSA-N 0.000 claims 1
• GHRJOAPWRFDMOM-UHFFFAOYSA-N 3-[1-(5,6-difluoropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C(F)C(F)=CC=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 GHRJOAPWRFDMOM-UHFFFAOYSA-N 0.000 claims 1
• RKZLYQZPCIQZQZ-UHFFFAOYSA-N 3-[1-(5,7-difluoro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C2=CC(F)=CC(F)=C2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 RKZLYQZPCIQZQZ-UHFFFAOYSA-N 0.000 claims 1
• XUTQBJPUOCOABD-UHFFFAOYSA-N 3-[1-(5-amino-6-chloro-3-fluoropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C(Cl)C(N)=CC(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 XUTQBJPUOCOABD-UHFFFAOYSA-N 0.000 claims 1
• LQLKVCSDKGBMDS-UHFFFAOYSA-N 3-[1-(5-bromo-1,3-thiazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound S1C(Br)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 LQLKVCSDKGBMDS-UHFFFAOYSA-N 0.000 claims 1
• NZXXUNUJINMXHC-UHFFFAOYSA-N 3-[1-(5-chloro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C2=CC(Cl)=CC=C2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 NZXXUNUJINMXHC-UHFFFAOYSA-N 0.000 claims 1
• DWADAENIHGYEOU-UHFFFAOYSA-N 3-[1-(5-fluoro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C2=CC(F)=CC=C2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DWADAENIHGYEOU-UHFFFAOYSA-N 0.000 claims 1
• KKTXGNLZUWKUSV-UHFFFAOYSA-N 3-[1-(5-fluoro-2,3-dihydrothieno[2,3-b]pyridin-6-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound FC1=CC=2CCSC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 KKTXGNLZUWKUSV-UHFFFAOYSA-N 0.000 claims 1
• DLOPYAXWZBPRKS-UHFFFAOYSA-N 3-[1-(5-fluoro-2-methoxypyrimidin-4-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound COC1=NC=C(F)C(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 DLOPYAXWZBPRKS-UHFFFAOYSA-N 0.000 claims 1
• XBOJDPCVPHZGFD-UHFFFAOYSA-N 3-[1-(6-bromo-3-fluoropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound FC1=CC=C(Br)N=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 XBOJDPCVPHZGFD-UHFFFAOYSA-N 0.000 claims 1
• LYIMAKJISPQIAA-UHFFFAOYSA-N 3-[1-(6-chloro-1-oxidopyridin-1-ium-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound [O-][N+]1=C(Cl)C=CC=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 LYIMAKJISPQIAA-UHFFFAOYSA-N 0.000 claims 1
• HTLWHISHLQLUFZ-UHFFFAOYSA-N 3-[1-(6-chloro-4-methyl-3-oxopyrazin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O=C1N(C)C=C(Cl)N=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 HTLWHISHLQLUFZ-UHFFFAOYSA-N 0.000 claims 1
• CYUZXDNPRPPMFR-UHFFFAOYSA-N 3-[1-(6-chloropyrazin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CN=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 CYUZXDNPRPPMFR-UHFFFAOYSA-N 0.000 claims 1
• ALRWBGCFSGJTNI-UHFFFAOYSA-N 3-[1-(6-ethylsulfonyl-3-fluoropyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCS(=O)(=O)C1=CC=C(F)C(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 ALRWBGCFSGJTNI-UHFFFAOYSA-N 0.000 claims 1
• GCLUICHMJWGYFL-UHFFFAOYSA-N 3-[1-(6-fluoro-[1,3]oxazolo[5,4-b]pyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C2=CC(F)=CN=C2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 GCLUICHMJWGYFL-UHFFFAOYSA-N 0.000 claims 1
• OSOIFKABHCXDLS-UHFFFAOYSA-N 3-[1-(6-methyl-[1,3]oxazolo[5,4-b]pyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N=1C2=CC(C)=CN=C2OC=1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 OSOIFKABHCXDLS-UHFFFAOYSA-N 0.000 claims 1
• BIAIJTUWVPAEPQ-UHFFFAOYSA-N 3-[1-(6-methylsulfonylpyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CS(=O)(=O)C1=CC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 BIAIJTUWVPAEPQ-UHFFFAOYSA-N 0.000 claims 1
• UOSMAANIOSVGQU-UHFFFAOYSA-N 3-[1-(7,7-difluoro-5,6-dihydrocyclopenta[b]pyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2C(F)(F)CCC2=CC=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 UOSMAANIOSVGQU-UHFFFAOYSA-N 0.000 claims 1
• FLYCSGUVCAIPPD-UHFFFAOYSA-N 3-[1-(7-bromo-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(Br)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 FLYCSGUVCAIPPD-UHFFFAOYSA-N 0.000 claims 1
• QQAOETZCYRZDOL-UHFFFAOYSA-N 3-[1-(7-ethoxy-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(OCC)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 QQAOETZCYRZDOL-UHFFFAOYSA-N 0.000 claims 1
• HTPPXCKSDVRROR-UHFFFAOYSA-N 3-[1-(7-fluoro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]propanenitrile Chemical compound O1C=2C(F)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 HTPPXCKSDVRROR-UHFFFAOYSA-N 0.000 claims 1
• YYTWVXNFGLIKDZ-UHFFFAOYSA-N 3-[1-(7-fluoro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(F)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 YYTWVXNFGLIKDZ-UHFFFAOYSA-N 0.000 claims 1
• PWBBHPLCHRUVAE-UHFFFAOYSA-N 3-[1-(7-hydroxy-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(O)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 PWBBHPLCHRUVAE-UHFFFAOYSA-N 0.000 claims 1
• DZPQUGDSGNWFAF-UHFFFAOYSA-N 3-[1-(7-methoxy-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(OC)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DZPQUGDSGNWFAF-UHFFFAOYSA-N 0.000 claims 1
• DNXJHZDYLLQBEA-UHFFFAOYSA-N 3-[1-(7-methylpyrrolo[2,3-d]pyrimidin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2N(C)C=CC2=CN=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DNXJHZDYLLQBEA-UHFFFAOYSA-N 0.000 claims 1
• FVVUVQKGNHBKLG-UHFFFAOYSA-N 3-[1-(8-chloroquinazolin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2C(Cl)=CC=CC2=CN=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 FVVUVQKGNHBKLG-UHFFFAOYSA-N 0.000 claims 1
• PIKBLHIWEZBCNI-UHFFFAOYSA-N 3-[1-(8-chloroquinolin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2C(Cl)=CC=CC2=CC=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 PIKBLHIWEZBCNI-UHFFFAOYSA-N 0.000 claims 1
• UCXNSCINTMLKDB-UHFFFAOYSA-N 3-[1-(8-fluoroquinazolin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=C2C(F)=CC=CC2=CN=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 UCXNSCINTMLKDB-UHFFFAOYSA-N 0.000 claims 1
• KEHVBRDYVCORFH-UHFFFAOYSA-N 3-[1-([1,3]oxazolo[4,5-b]pyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C=2OC3=CC=CN=C3N=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 KEHVBRDYVCORFH-UHFFFAOYSA-N 0.000 claims 1
• XJKFOVYKFOFDKS-UHFFFAOYSA-N 3-[1-([1,3]oxazolo[5,4-b]pyridin-2-yl)pyrrolidin-3-yl]-3-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]propanenitrile Chemical compound C1CN(C=2OC3=NC=CC=C3N=2)CC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 XJKFOVYKFOFDKS-UHFFFAOYSA-N 0.000 claims 1
• LYLRBXMIWKSYNO-UHFFFAOYSA-N 3-[1-([1,3]oxazolo[5,4-d]pyrimidin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C=2OC3=NC=NC=C3N=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 LYLRBXMIWKSYNO-UHFFFAOYSA-N 0.000 claims 1
• FPLXONGIEISLNE-UHFFFAOYSA-N 3-[1-[3,5-difluoro-6-(2,2,2-trifluoroethylsulfonyl)pyridin-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound FC1=CC(F)=C(S(=O)(=O)CC(F)(F)F)N=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 FPLXONGIEISLNE-UHFFFAOYSA-N 0.000 claims 1
• ALACHHDQWAKNRE-UHFFFAOYSA-N 3-[1-[3-fluoro-4-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N1=CC=C(C(F)(F)F)C(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 ALACHHDQWAKNRE-UHFFFAOYSA-N 0.000 claims 1
• NZHZDRMKTJOQEN-UHFFFAOYSA-N 3-[1-[4-(dimethylamino)pyrimidin-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CN(C)C1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 NZHZDRMKTJOQEN-UHFFFAOYSA-N 0.000 claims 1
• UIOFSTALQYUAFN-UHFFFAOYSA-N 3-[1-[4-(propan-2-ylamino)pyrimidin-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC(C)NC1=CC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 UIOFSTALQYUAFN-UHFFFAOYSA-N 0.000 claims 1
• WJTYXWPSHWNASX-UHFFFAOYSA-N 3-[1-[7-(difluoromethoxy)-1,3-benzoxazol-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(OC(F)F)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 WJTYXWPSHWNASX-UHFFFAOYSA-N 0.000 claims 1
• VGJOQFGHSBXEQN-UHFFFAOYSA-N 3-[1-[7-(hydroxymethyl)-1,3-benzoxazol-2-yl]pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound O1C=2C(CO)=CC=CC=2N=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 VGJOQFGHSBXEQN-UHFFFAOYSA-N 0.000 claims 1
• HFFIKIKAINSUNA-UHFFFAOYSA-N 3-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]pyrazine-2-carbonitrile Chemical compound C1=CC(C=2C=3C=CNC=3N=CN=2)=CN1C(CC#N)C(C1)CCN1C1=NC=CN=C1C#N HFFIKIKAINSUNA-UHFFFAOYSA-N 0.000 claims 1
• DQSQCCHMCXFAQU-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-2,5,6-trifluoropyridine-4-carbonitrile Chemical compound N#CC1=C(F)C(F)=NC(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 DQSQCCHMCXFAQU-UHFFFAOYSA-N 0.000 claims 1
• VCTNUTHQWLBGIT-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(difluoromethyl)pyrazine-2-carbonitrile Chemical compound N#CC1=NC(C(F)F)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 VCTNUTHQWLBGIT-UHFFFAOYSA-N 0.000 claims 1
• SYEBNPSSZYNIQX-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(hydroxymethyl)pyrazine-2-carbonitrile Chemical compound N#CC1=NC(CO)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 SYEBNPSSZYNIQX-UHFFFAOYSA-N 0.000 claims 1
• YYCKMTLYWUHULV-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(methoxymethyl)pyrazine-2-carbonitrile Chemical compound N#CC1=NC(COC)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 YYCKMTLYWUHULV-UHFFFAOYSA-N 0.000 claims 1
• GOASDLKBVGRPDE-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-ethylpyrazine-2-carbonitrile Chemical compound N#CC1=NC(CC)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 GOASDLKBVGRPDE-UHFFFAOYSA-N 0.000 claims 1
• QHCDJNDCXVLFAD-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-ethynylpyrazine-2-carbonitrile Chemical compound N#CC1=NC(C#C)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 QHCDJNDCXVLFAD-UHFFFAOYSA-N 0.000 claims 1
• WUSKTICHQHMRQJ-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methylpyrazine-2-carbonitrile Chemical compound N#CC1=NC(C)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 WUSKTICHQHMRQJ-UHFFFAOYSA-N 0.000 claims 1
• JYFQOBGBEXORRI-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyrazine-2-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=NC=CN=C1C#N JYFQOBGBEXORRI-UHFFFAOYSA-N 0.000 claims 1
• QFIFNABGHFOUIM-UHFFFAOYSA-N 3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-2-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=CC=CN=C1C#N QFIFNABGHFOUIM-UHFFFAOYSA-N 0.000 claims 1
• JVHIZZCDRIGJBV-UHFFFAOYSA-N 3-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]benzene-1,2-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CF)C(C1)CCN1C1=CC=CC(C#N)=C1C#N JVHIZZCDRIGJBV-UHFFFAOYSA-N 0.000 claims 1
• HLGDFUIGAQUWFG-UHFFFAOYSA-N 3-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-2-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CF)C(C1)CCN1C1=CC=CN=C1C#N HLGDFUIGAQUWFG-UHFFFAOYSA-N 0.000 claims 1
• GYDKVYRYQPIQGC-UHFFFAOYSA-N 3-[3-fluoro-1-([1,3]oxazolo[5,4-b]pyridin-2-yl)pyrrolidin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C=2OC3=NC=CC=C3N=2)CC1(F)C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 GYDKVYRYQPIQGC-UHFFFAOYSA-N 0.000 claims 1
• DGLUGWWEJIAFRR-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-(1-thieno[2,3-b]pyridin-6-ylpyrrolidin-3-yl)propanenitrile Chemical compound C1CN(C=2N=C3SC=CC3=CC=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DGLUGWWEJIAFRR-UHFFFAOYSA-N 0.000 claims 1
• GURIZSHGALPTLI-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-[1-(2-sulfanylidene-1h-pyrimidin-6-yl)pyrrolidin-3-yl]propanenitrile Chemical compound SC1=NC=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 GURIZSHGALPTLI-UHFFFAOYSA-N 0.000 claims 1
• WQWACVUMXYCCDM-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-[1-(3,5,6-trifluoropyridin-2-yl)pyrrolidin-3-yl]propanenitrile Chemical compound N1=C(F)C(F)=CC(F)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 WQWACVUMXYCCDM-UHFFFAOYSA-N 0.000 claims 1
• XKNYZTRLBAWHLR-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-[1-(7h-pyrrolo[2,3-d]pyrimidin-2-yl)pyrrolidin-3-yl]propanenitrile Chemical compound C1CN(C=2N=C3NC=CC3=CN=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 XKNYZTRLBAWHLR-UHFFFAOYSA-N 0.000 claims 1
• CWLBDZOYIRYNCX-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-[1-([1,3]thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl]propanenitrile Chemical compound C1CN(C=2N=C3SC=NC3=CN=2)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 CWLBDZOYIRYNCX-UHFFFAOYSA-N 0.000 claims 1
• GMLMGTCVNFNEGC-UHFFFAOYSA-N 3-chloro-2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-4-carbonitrile Chemical compound ClC1=C(C#N)C=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 GMLMGTCVNFNEGC-UHFFFAOYSA-N 0.000 claims 1
• VRUBJWYNZWCNDF-UHFFFAOYSA-N 3-chloro-5-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-4-carbonitrile Chemical compound ClC1=CN=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N VRUBJWYNZWCNDF-UHFFFAOYSA-N 0.000 claims 1
• OWPHFTGLZFOMFX-UHFFFAOYSA-N 4-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]pyridazine-3-carbonitrile Chemical compound C1=CC(C=2C=3C=CNC=3N=CN=2)=CN1C(CC#N)C(C1)CCN1C1=CC=NN=C1C#N OWPHFTGLZFOMFX-UHFFFAOYSA-N 0.000 claims 1
• LMWYPDZKMCCLDY-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-1,3-thiazole-5-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C=1N=CSC=1C#N LMWYPDZKMCCLDY-UHFFFAOYSA-N 0.000 claims 1
• FDFARYSNWIJSDD-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-(difluoromethyl)pyrimidine-5-carbonitrile Chemical compound FC(F)C1=NC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N FDFARYSNWIJSDD-UHFFFAOYSA-N 0.000 claims 1
• IMNPOOLJHSPQRW-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-6-methoxypyrimidine-5-carbonitrile Chemical compound COC1=NC=NC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N IMNPOOLJHSPQRW-UHFFFAOYSA-N 0.000 claims 1
• YISRTCGNWFPLGZ-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-n,n-dimethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 YISRTCGNWFPLGZ-UHFFFAOYSA-N 0.000 claims 1
• NUSXQXLYJKUWNL-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-n-phenylpyridine-2-carboxamide Chemical compound C=1C(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=NC=1C(=O)NC1=CC=CC=C1 NUSXQXLYJKUWNL-UHFFFAOYSA-N 0.000 claims 1
• HFEVVJIYYPUOKE-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridazine-3-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=CC=NN=C1C#N HFEVVJIYYPUOKE-UHFFFAOYSA-N 0.000 claims 1
• OFYPQNBIWGGUIF-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridine-2,3-dicarbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=CC=NC(C#N)=C1C#N OFYPQNBIWGGUIF-UHFFFAOYSA-N 0.000 claims 1
• OCZDPFOTBFXHPI-UHFFFAOYSA-N 4-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C1)CCN1C1=NC=NC=C1C#N OCZDPFOTBFXHPI-UHFFFAOYSA-N 0.000 claims 1
• QPXDQMYFKFBVNJ-UHFFFAOYSA-N 4-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyridazine-3-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CF)C(C1)CCN1C1=CC=NN=C1C#N QPXDQMYFKFBVNJ-UHFFFAOYSA-N 0.000 claims 1
• BXTFVTURAMTMFF-UHFFFAOYSA-N 4-chloro-2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]thiophene-3-carbonitrile Chemical compound ClC1=CSC(N2CC(CC2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1C#N BXTFVTURAMTMFF-UHFFFAOYSA-N 0.000 claims 1
• ZBCHRLAVZRHFEN-UHFFFAOYSA-N 5-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]-1,3-thiazole-4-carbonitrile Chemical compound C1=CC(C=2C=3C=CNC=3N=CN=2)=CN1C(CC#N)C(C1)CCN1C=1SC=NC=1C#N ZBCHRLAVZRHFEN-UHFFFAOYSA-N 0.000 claims 1
• IXJBJDAMCUCSFX-UHFFFAOYSA-N 5-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]thieno[2,3-c]pyridine-4-carbonitrile Chemical compound C1CN(C=2C(=C3C=CSC3=CN=2)C#N)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 IXJBJDAMCUCSFX-UHFFFAOYSA-N 0.000 claims 1
• MTFXYARJYJJTEL-UHFFFAOYSA-N 5-[3-[2-fluoro-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]-1,3-thiazole-4-carbonitrile Chemical compound C1=CC(C=2C=3C=CNC=3N=CN=2)=CN1C(CF)C(C1)CCN1C=1SC=NC=1C#N MTFXYARJYJJTEL-UHFFFAOYSA-N 0.000 claims 1
• RFJXUTMEOFMZMS-UHFFFAOYSA-N 5-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-1,3-thiazole-4-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CF)C(C1)CCN1C=1SC=NC=1C#N RFJXUTMEOFMZMS-UHFFFAOYSA-N 0.000 claims 1
• RIEKSXWHMJBREX-UHFFFAOYSA-N 5-fluoro-6-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-2,3-dihydrothieno[2,3-b]pyridine 1,1-dioxide Chemical compound C1CN(C=2C(=CC3=C(S(CC3)(=O)=O)N=2)F)CC1C(CF)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 RIEKSXWHMJBREX-UHFFFAOYSA-N 0.000 claims 1
• XCJCQKWFBXABHM-FUKCDUGKSA-N 6-[(3s)-3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-1,1-dioxo-2,3-dihydrothieno[3,2-c]pyridine-7-carbonitrile Chemical compound FCC([C@@H]1CN(CC1)C=1C(=C2S(=O)(=O)CCC2=CN=1)C#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 XCJCQKWFBXABHM-FUKCDUGKSA-N 0.000 claims 1
• XNSRYSRHXYXTHO-UHFFFAOYSA-N 6-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]-2,3-dihydrothieno[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3SCCC3=CN=2)C#N)CC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 XNSRYSRHXYXTHO-UHFFFAOYSA-N 0.000 claims 1
• VLGAERDMEPFRGO-UHFFFAOYSA-N 6-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]furo[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3OC=CC3=CN=2)C#N)CC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 VLGAERDMEPFRGO-UHFFFAOYSA-N 0.000 claims 1
• SJJWWGIBXIWPIO-UHFFFAOYSA-N 6-[3-[2-cyano-1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrol-1-yl]ethyl]pyrrolidin-1-yl]thieno[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3SC=CC3=CN=2)C#N)CC1C(CC#N)N(C=1)C=CC=1C1=NC=NC2=C1C=CN2 SJJWWGIBXIWPIO-UHFFFAOYSA-N 0.000 claims 1
• AEABGHSQWMLSNK-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-1,1-dioxo-2,3-dihydrothieno[3,2-c]pyridine-7-carbonitrile Chemical compound N#CC1=C2S(=O)(=O)CCC2=CN=C1N(C1)CCC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 AEABGHSQWMLSNK-UHFFFAOYSA-N 0.000 claims 1
• VADMDPAPYZJAIW-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-2,3-difluorobenzonitrile Chemical compound N#CC1=C(F)C(F)=CC=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 VADMDPAPYZJAIW-UHFFFAOYSA-N 0.000 claims 1
• GNTJTTVXQNUVRV-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-2,3-dihydrothieno[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3SCCC3=CN=2)C#N)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 GNTJTTVXQNUVRV-UHFFFAOYSA-N 0.000 claims 1
• UMPNZXZFQAOEGF-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-fluoropyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 UMPNZXZFQAOEGF-UHFFFAOYSA-N 0.000 claims 1
• RSEDUABBQIKFGB-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]furo[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3OC=CC3=CN=2)C#N)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 RSEDUABBQIKFGB-UHFFFAOYSA-N 0.000 claims 1
• FTAIFQYHNYHENZ-UHFFFAOYSA-N 6-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]thieno[3,2-c]pyridine-7-carbonitrile Chemical compound C1CN(C=2C(=C3SC=CC3=CN=2)C#N)CC1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 FTAIFQYHNYHENZ-UHFFFAOYSA-N 0.000 claims 1
• HIVUIQFTFLJUMD-UHFFFAOYSA-N 6-[3-[2-fluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-2,3-dihydrothieno[2,3-b]pyridine 1,1-dioxide Chemical compound C1CN(C=2N=C3S(=O)(=O)CCC3=CC=2)CC1C(CF)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 HIVUIQFTFLJUMD-UHFFFAOYSA-N 0.000 claims 1
• POLKHCBZAIGLLH-UHFFFAOYSA-N 6-bromo-3-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]pyrazine-2-carbonitrile Chemical compound N#CC1=NC(Br)=CN=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 POLKHCBZAIGLLH-UHFFFAOYSA-N 0.000 claims 1
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 1
• QHFJTAODKYXVOW-UHFFFAOYSA-N n-[6-chloro-2-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyrrolidin-1-yl]-5-fluoropyridin-3-yl]formamide Chemical compound N1=C(Cl)C(F)=CC(NC=O)=C1N1CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CC1 QHFJTAODKYXVOW-UHFFFAOYSA-N 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 73
• 201000010099 disease Diseases 0.000 abstract description 56
• 206010028980 Neoplasm Diseases 0.000 abstract description 23
• 238000011282 treatment Methods 0.000 abstract description 16
• 201000011510 cancer Diseases 0.000 abstract description 15
• 208000027866 inflammatory disease Diseases 0.000 abstract description 11
• 208000023275 Autoimmune disease Diseases 0.000 abstract description 7
• 102000042838 JAK family Human genes 0.000 abstract description 4
• 108091082332 JAK family Proteins 0.000 abstract description 4
• 230000002757 inflammatory effect Effects 0.000 abstract description 4
• 229940116839 Janus kinase 1 inhibitor Drugs 0.000 abstract description 3
• 239000000203 mixture Substances 0.000 description 207
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 74
• 125000004432 carbon atom Chemical group C* 0.000 description 71
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
• 239000000047 product Substances 0.000 description 61
• 235000002639 sodium chloride Nutrition 0.000 description 61
• 239000002904 solvent Substances 0.000 description 61
• 239000000126 substance Substances 0.000 description 57
• 238000009472 formulation Methods 0.000 description 52
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 50
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 49
• 229910001868 water Inorganic materials 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
• 238000000034 method Methods 0.000 description 46
• 239000003814 drug Substances 0.000 description 44
• 239000000243 solution Substances 0.000 description 42
• 229910052702 rhenium Inorganic materials 0.000 description 41
• 108010024121 Janus Kinases Proteins 0.000 description 34
• 102000015617 Janus Kinases Human genes 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 28
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 28
• 235000011114 ammonium hydroxide Nutrition 0.000 description 28
• 229910021481 rutherfordium Inorganic materials 0.000 description 26
• 239000003795 chemical substances by application Substances 0.000 description 25
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 24
• 238000004949 mass spectrometry Methods 0.000 description 24
• 229940124597 therapeutic agent Drugs 0.000 description 24
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• 229920000642 polymer Polymers 0.000 description 22
• 238000002953 preparative HPLC Methods 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 21
• 125000003118 aryl group Chemical group 0.000 description 21
• 239000003921 oil Substances 0.000 description 21
• 235000019198 oils Nutrition 0.000 description 21
• 125000006239 protecting group Chemical group 0.000 description 20
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 19
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
• 235000014113 dietary fatty acids Nutrition 0.000 description 18
• 235000019441 ethanol Nutrition 0.000 description 18
• 239000000194 fatty acid Substances 0.000 description 18
• 229930195729 fatty acid Natural products 0.000 description 18
• 239000003381 stabilizer Substances 0.000 description 18
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 17
• 125000002947 alkylene group Chemical group 0.000 description 17
• 208000035475 disorder Diseases 0.000 description 17
• 239000003995 emulsifying agent Substances 0.000 description 17
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 17
• 150000004665 fatty acids Chemical class 0.000 description 17
• 125000002950 monocyclic group Chemical group 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• 229920001223 polyethylene glycol Polymers 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• 239000000546 pharmaceutical excipient Substances 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 14
• 101150041968 CDC13 gene Proteins 0.000 description 13
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
• 239000002552 dosage form Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 239000007788 liquid Substances 0.000 description 12
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
• 239000011159 matrix material Substances 0.000 description 12
• 239000003755 preservative agent Substances 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 239000002202 Polyethylene glycol Substances 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000003974 emollient agent Substances 0.000 description 11
• 239000000284 extract Substances 0.000 description 11
• 150000002191 fatty alcohols Chemical class 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• 239000012458 free base Substances 0.000 description 11
• 235000019271 petrolatum Nutrition 0.000 description 11
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 11
• 239000003351 stiffener Substances 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 208000003556 Dry Eye Syndromes Diseases 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 230000000845 anti-microbial effect Effects 0.000 description 9
• 230000008901 benefit Effects 0.000 description 9
• 229910052799 carbon Inorganic materials 0.000 description 9
• 239000010408 film Substances 0.000 description 9
• 230000014759 maintenance of location Effects 0.000 description 9
• 239000008177 pharmaceutical agent Substances 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 230000002335 preservative effect Effects 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 8
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
• 206010013774 Dry eye Diseases 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• 238000002156 mixing Methods 0.000 description 8
• 239000002674 ointment Substances 0.000 description 8
• 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 7
• 229960000541 cetyl alcohol Drugs 0.000 description 7
• 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
• 229940043355 kinase inhibitor Drugs 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• 239000001301 oxygen Substances 0.000 description 7
• 239000002245 particle Substances 0.000 description 7
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 7
• 238000002390 rotary evaporation Methods 0.000 description 7
• JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 7
• 230000000699 topical effect Effects 0.000 description 7
• 241000282414 Homo sapiens Species 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 6
• 208000014767 Myeloproliferative disease Diseases 0.000 description 6
• 108091000080 Phosphotransferase Proteins 0.000 description 6
• 229940124639 Selective inhibitor Drugs 0.000 description 6
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 229960003957 dexamethasone Drugs 0.000 description 6
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 6
• 229940008099 dimethicone Drugs 0.000 description 6
• 239000004205 dimethyl polysiloxane Substances 0.000 description 6
• 239000006196 drop Substances 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 239000012530 fluid Substances 0.000 description 6
• 230000004054 inflammatory process Effects 0.000 description 6
• 229940057917 medium chain triglycerides Drugs 0.000 description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 125000006353 oxyethylene group Chemical group 0.000 description 6
• 102000020233 phosphotransferase Human genes 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 208000003476 primary myelofibrosis Diseases 0.000 description 6
• 235000013772 propylene glycol Nutrition 0.000 description 6
• 229960004063 propylene glycol Drugs 0.000 description 6
• 208000017520 skin disease Diseases 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• 150000003626 triacylglycerols Chemical class 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 5
• 201000004624 Dermatitis Diseases 0.000 description 5
• 239000004166 Lanolin Substances 0.000 description 5
• 208000034578 Multiple myelomas Diseases 0.000 description 5
• 239000004264 Petrolatum Substances 0.000 description 5
• 206010035226 Plasma cell myeloma Diseases 0.000 description 5
• 229920001213 Polysorbate 20 Polymers 0.000 description 5
• 102000001253 Protein Kinase Human genes 0.000 description 5
• 201000004681 Psoriasis Diseases 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
• 239000002738 chelating agent Substances 0.000 description 5
• 238000004296 chiral HPLC Methods 0.000 description 5
• 229920001577 copolymer Polymers 0.000 description 5
• 239000003246 corticosteroid Substances 0.000 description 5
• 239000007822 coupling agent Substances 0.000 description 5
• 238000010511 deprotection reaction Methods 0.000 description 5
• 238000005516 engineering process Methods 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 235000019388 lanolin Nutrition 0.000 description 5
• 229940039717 lanolin Drugs 0.000 description 5
• 229940059904 light mineral oil Drugs 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 239000004005 microsphere Substances 0.000 description 5
• 206010028537 myelofibrosis Diseases 0.000 description 5
• GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 5
• 210000000056 organ Anatomy 0.000 description 5
• 229940066842 petrolatum Drugs 0.000 description 5
• 229940124531 pharmaceutical excipient Drugs 0.000 description 5
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 5
• 108060006633 protein kinase Proteins 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 239000008247 solid mixture Substances 0.000 description 5
• 229940012831 stearyl alcohol Drugs 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 229910052717 sulfur Inorganic materials 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 230000001225 therapeutic effect Effects 0.000 description 5
• ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 4
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 4
• 102000004127 Cytokines Human genes 0.000 description 4
• 108090000695 Cytokines Proteins 0.000 description 4
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
• 206010012442 Dermatitis contact Diseases 0.000 description 4
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
• 208000032027 Essential Thrombocythemia Diseases 0.000 description 4
• 102100037813 Focal adhesion kinase 1 Human genes 0.000 description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
• 238000006845 Michael addition reaction Methods 0.000 description 4
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 4
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
• 229920002125 Sokalan® Polymers 0.000 description 4
• 206010052779 Transplant rejections Diseases 0.000 description 4
• 125000004450 alkenylene group Chemical group 0.000 description 4
• 239000000908 ammonium hydroxide Substances 0.000 description 4
• 239000007900 aqueous suspension Substances 0.000 description 4
• 229920002988 biodegradable polymer Polymers 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 230000003197 catalytic effect Effects 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 238000012377 drug delivery Methods 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 229940075529 glyceryl stearate Drugs 0.000 description 4
• 239000003102 growth factor Substances 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 239000002198 insoluble material Substances 0.000 description 4
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
• 239000000178 monomer Substances 0.000 description 4
• 201000005962 mycosis fungoides Diseases 0.000 description 4
• 239000002105 nanoparticle Substances 0.000 description 4
• 230000007170 pathology Effects 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 239000004584 polyacrylic acid Substances 0.000 description 4
• 229920001515 polyalkylene glycol Polymers 0.000 description 4
• 125000003367 polycyclic group Chemical group 0.000 description 4
• 229940068977 polysorbate 20 Drugs 0.000 description 4
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 229910001961 silver nitrate Inorganic materials 0.000 description 4
• 210000003491 skin Anatomy 0.000 description 4
• 235000011121 sodium hydroxide Nutrition 0.000 description 4
• 235000011069 sorbitan monooleate Nutrition 0.000 description 4
• 239000001593 sorbitan monooleate Substances 0.000 description 4
• 229940035049 sorbitan monooleate Drugs 0.000 description 4
• 239000000600 sorbitol Substances 0.000 description 4
• 235000010356 sorbitol Nutrition 0.000 description 4
• 230000001954 sterilising effect Effects 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• 239000003871 white petrolatum Substances 0.000 description 4
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
• KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
• ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 3
• WKMUUISSZDCMKG-UHFFFAOYSA-N 1h-[1,3]oxazolo[5,4-b]pyridine-2-thione Chemical compound C1=CN=C2OC(S)=NC2=C1 WKMUUISSZDCMKG-UHFFFAOYSA-N 0.000 description 3
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• 108010036949 Cyclosporine Proteins 0.000 description 3
• 108090001005 Interleukin-6 Proteins 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• 201000011152 Pemphigus Diseases 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 206010039705 Scleritis Diseases 0.000 description 3
• 206010070834 Sensitisation Diseases 0.000 description 3
• 206010070835 Skin sensitisation Diseases 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
• 206010046851 Uveitis Diseases 0.000 description 3
• 102100025093 Zinc fingers and homeoboxes protein 2 Human genes 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 150000001336 alkenes Chemical class 0.000 description 3
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 230000000973 chemotherapeutic effect Effects 0.000 description 3
• 230000001684 chronic effect Effects 0.000 description 3
• 208000010247 contact dermatitis Diseases 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 210000000744 eyelid Anatomy 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 230000014509 gene expression Effects 0.000 description 3
• 150000004676 glycans Chemical class 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
• 229920003063 hydroxymethyl cellulose Polymers 0.000 description 3
• 229940031574 hydroxymethyl cellulose Drugs 0.000 description 3
• 239000003456 ion exchange resin Substances 0.000 description 3
• 229920003303 ion-exchange polymer Polymers 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 3
• 229960001924 melphalan Drugs 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 201000001976 pemphigus vulgaris Diseases 0.000 description 3
• 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 3
• 229920001610 polycaprolactone Polymers 0.000 description 3
• 239000004632 polycaprolactone Substances 0.000 description 3
• 229920001282 polysaccharide Polymers 0.000 description 3
• 239000005017 polysaccharide Substances 0.000 description 3
• 229920002451 polyvinyl alcohol Polymers 0.000 description 3
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 235000011181 potassium carbonates Nutrition 0.000 description 3
• 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 3
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 description 3
• 210000002345 respiratory system Anatomy 0.000 description 3
• QTTRZHGPGKRAFB-OOKHYKNYSA-N rimexolone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CC)(C)[C@@]1(C)C[C@@H]2O QTTRZHGPGKRAFB-OOKHYKNYSA-N 0.000 description 3
• 230000008313 sensitization Effects 0.000 description 3
• 231100000370 skin sensitisation Toxicity 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 238000004659 sterilization and disinfection Methods 0.000 description 3
• 150000003431 steroids Chemical class 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 230000009885 systemic effect Effects 0.000 description 3
• 150000003512 tertiary amines Chemical class 0.000 description 3
• 150000003568 thioethers Chemical group 0.000 description 3
• 239000000230 xanthan gum Substances 0.000 description 3
• 229920001285 xanthan gum Polymers 0.000 description 3
• 235000010493 xanthan gum Nutrition 0.000 description 3
• 229940082509 xanthan gum Drugs 0.000 description 3
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
• KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 2
• FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 2
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
• CRBBOOXGHMTWOC-NPDDRXJXSA-N 1,4-Anhydro-6-O-dodecanoyl-2,3-bis-O-(2-hydroxyethyl)-D-glucitol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](OCCO)[C@H]1OCCO CRBBOOXGHMTWOC-NPDDRXJXSA-N 0.000 description 2
• JSFATNQSLKRBCI-VAEKSGALSA-N 15(S)-HETE Chemical compound CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O JSFATNQSLKRBCI-VAEKSGALSA-N 0.000 description 2
• XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
• CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 2
• QOZLOYKAFDTQNU-UHFFFAOYSA-N 2-amino-3-fluorophenol Chemical compound NC1=C(O)C=CC=C1F QOZLOYKAFDTQNU-UHFFFAOYSA-N 0.000 description 2
• MDIAVSZFIQWYST-UHFFFAOYSA-N 2-amino-6-fluorophenol Chemical compound NC1=CC=CC(F)=C1O MDIAVSZFIQWYST-UHFFFAOYSA-N 0.000 description 2
• BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 2
• WOIRQILACBXPIQ-UHFFFAOYSA-N 2-chloro-7-methylpyrrolo[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2N(C)C=CC2=C1 WOIRQILACBXPIQ-UHFFFAOYSA-N 0.000 description 2
• HJOQGBBHVRYTDX-UHFFFAOYSA-N 2-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=C2C=CNC2=N1 HJOQGBBHVRYTDX-UHFFFAOYSA-N 0.000 description 2
• QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
• VTSFNCCQCOEPKF-UHFFFAOYSA-N 3-amino-1h-pyridin-2-one Chemical compound NC1=CC=CN=C1O VTSFNCCQCOEPKF-UHFFFAOYSA-N 0.000 description 2
• ZNMZQYAQKSDACX-UHFFFAOYSA-N 3-amino-5-fluoro-1h-pyridin-2-one Chemical compound NC1=CC(F)=CN=C1O ZNMZQYAQKSDACX-UHFFFAOYSA-N 0.000 description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
• XWLBYEBHQNSCKA-UHFFFAOYSA-N 5-amino-1h-pyrimidin-6-one Chemical compound NC1=CN=CN=C1O XWLBYEBHQNSCKA-UHFFFAOYSA-N 0.000 description 2
• XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
• DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 2
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
• 206010009900 Colitis ulcerative Diseases 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 2
• 206010010741 Conjunctivitis Diseases 0.000 description 2
• 208000011231 Crohn disease Diseases 0.000 description 2
• 229920001651 Cyanoacrylate Polymers 0.000 description 2
• 206010012438 Dermatitis atopic Diseases 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 208000010201 Exanthema Diseases 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 201000005569 Gout Diseases 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 2
• 241000701085 Human alphaherpesvirus 3 Species 0.000 description 2
• 241000701044 Human gammaherpesvirus 4 Species 0.000 description 2
• 241000701806 Human papillomavirus Species 0.000 description 2
• 206010048643 Hypereosinophilic syndrome Diseases 0.000 description 2
• 208000004575 Infectious Arthritis Diseases 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 2
• NMLMACJWHPHKGR-NCOIDOBVSA-N P(1),P(4)-bis(uridin-5'-yl) tetraphosphate Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@H]2O)O)COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N2C(NC(=O)C=C2)=O)O)O)C=CC(=O)NC1=O NMLMACJWHPHKGR-NCOIDOBVSA-N 0.000 description 2
• 206010034277 Pemphigoid Diseases 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
• 239000004372 Polyvinyl alcohol Substances 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
• 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 2
• HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
• 239000004147 Sorbitan trioleate Substances 0.000 description 2
• PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 description 2
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
• 201000008736 Systemic mastocytosis Diseases 0.000 description 2
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 2
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
• 239000004098 Tetracycline Substances 0.000 description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 description 2
• IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 208000017733 acquired polycythemia vera Diseases 0.000 description 2
• 239000000654 additive Substances 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 208000007502 anemia Diseases 0.000 description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 description 2
• 239000002260 anti-inflammatory agent Substances 0.000 description 2
• 239000004599 antimicrobial Substances 0.000 description 2
• 239000002246 antineoplastic agent Substances 0.000 description 2
• 239000003963 antioxidant agent Substances 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
• 239000000607 artificial tear Substances 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 201000008937 atopic dermatitis Diseases 0.000 description 2
• 230000001363 autoimmune Effects 0.000 description 2
• 235000013871 bee wax Nutrition 0.000 description 2
• 229940092738 beeswax Drugs 0.000 description 2
• 239000012166 beeswax Substances 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 230000003115 biocidal effect Effects 0.000 description 2
• 239000004621 biodegradable polymer Substances 0.000 description 2
• 229920013641 bioerodible polymer Polymers 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 229960001467 bortezomib Drugs 0.000 description 2
• 208000000594 bullous pemphigoid Diseases 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
• 239000004203 carnauba wax Substances 0.000 description 2
• 235000013869 carnauba wax Nutrition 0.000 description 2
• 229940082483 carnauba wax Drugs 0.000 description 2
• 210000000845 cartilage Anatomy 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 125000003636 chemical group Chemical group 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 235000012000 cholesterol Nutrition 0.000 description 2
• 229960001265 ciclosporin Drugs 0.000 description 2
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 239000000470 constituent Substances 0.000 description 2
• 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
• 229930182912 cyclosporin Natural products 0.000 description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 230000003111 delayed effect Effects 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• 229950003529 diquafosol Drugs 0.000 description 2
• 238000004090 dissolution Methods 0.000 description 2
• NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
• UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
• 229960004679 doxorubicin Drugs 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 239000002158 endotoxin Substances 0.000 description 2
• 239000012055 enteric layer Substances 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 201000005884 exanthem Diseases 0.000 description 2
• FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical group C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
• SCAPHSPFYDTKEV-UHFFFAOYSA-N furo[3,2-c]pyridine-7-carbonitrile Chemical compound N#CC1=CN=CC2=C1OC=C2 SCAPHSPFYDTKEV-UHFFFAOYSA-N 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 229940014259 gelatin Drugs 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 230000002209 hydrophobic effect Effects 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 2
• 229960002411 imatinib Drugs 0.000 description 2
• 229960003444 immunosuppressant agent Drugs 0.000 description 2
• 239000003018 immunosuppressive agent Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 201000004614 iritis Diseases 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 210000003593 megakaryocyte Anatomy 0.000 description 2
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
• 229960002216 methylparaben Drugs 0.000 description 2
• 238000003801 milling Methods 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 229960004023 minocycline Drugs 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 2
• 239000007764 o/w emulsion Substances 0.000 description 2
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
• 102000027450 oncoproteins Human genes 0.000 description 2
• 108091008819 oncoproteins Proteins 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000005702 oxyalkylene group Chemical group 0.000 description 2
• SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
• 229960005323 phenoxyethanol Drugs 0.000 description 2
• IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical group CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
• 208000037244 polycythemia vera Diseases 0.000 description 2
• 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
• 229960004618 prednisone Drugs 0.000 description 2
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 230000035755 proliferation Effects 0.000 description 2
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
• 229960003415 propylparaben Drugs 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 239000008213 purified water Substances 0.000 description 2
• ALJUMASAQKRVRM-UHFFFAOYSA-N pyridine-3,4-dicarbonitrile Chemical compound N#CC1=CC=NC=C1C#N ALJUMASAQKRVRM-UHFFFAOYSA-N 0.000 description 2
• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 2
• XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 description 2
• DJQOGYTZMZEXJN-UHFFFAOYSA-N pyrrolidine-1-carbothioamide Chemical compound NC(=S)N1CCCC1 DJQOGYTZMZEXJN-UHFFFAOYSA-N 0.000 description 2
• 206010037844 rash Diseases 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 230000000241 respiratory effect Effects 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• 229910052701 rubidium Inorganic materials 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 201000001223 septic arthritis Diseases 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 229960001922 sodium perborate Drugs 0.000 description 2
• YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 2
• 229940035044 sorbitan monolaurate Drugs 0.000 description 2
• 235000011071 sorbitan monopalmitate Nutrition 0.000 description 2
• 239000001570 sorbitan monopalmitate Substances 0.000 description 2
• 229940031953 sorbitan monopalmitate Drugs 0.000 description 2
• 235000011076 sorbitan monostearate Nutrition 0.000 description 2
• 239000001587 sorbitan monostearate Substances 0.000 description 2
• 229940035048 sorbitan monostearate Drugs 0.000 description 2
• 235000019337 sorbitan trioleate Nutrition 0.000 description 2
• 229960000391 sorbitan trioleate Drugs 0.000 description 2
• 235000011078 sorbitan tristearate Nutrition 0.000 description 2
• 239000001589 sorbitan tristearate Substances 0.000 description 2
• 229960004129 sorbitan tristearate Drugs 0.000 description 2
• 125000003003 spiro group Chemical group 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• 239000000758 substrate Substances 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 230000004083 survival effect Effects 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 230000002459 sustained effect Effects 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000019364 tetracycline Nutrition 0.000 description 2
• 150000003522 tetracyclines Chemical class 0.000 description 2
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
• 229960003433 thalidomide Drugs 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• QPRFUBYHVGOQJX-UHFFFAOYSA-N thieno[3,2-c]pyridine-7-carbonitrile Chemical compound N#CC1=CN=CC2=C1SC=C2 QPRFUBYHVGOQJX-UHFFFAOYSA-N 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• 125000004149 thio group Chemical group *S* 0.000 description 2
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
• 206010043554 thrombocytopenia Diseases 0.000 description 2
• 230000017423 tissue regeneration Effects 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• 239000012049 topical pharmaceutical composition Substances 0.000 description 2
• 230000036572 transepidermal water loss Effects 0.000 description 2
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
• FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 description 1
• SFWLDKQAUHFCBS-AOEYGKNYSA-N (1S,4S,13S,16S,19S,22S,25S,28R,31S,37S,40S,41S,44R,47S,50S,53S,56R,65S,70S)-44-amino-47-(4-aminobutyl)-4,16,22-tribenzyl-31-[(R)-carboxy(hydroxy)methyl]-2,5,14,17,20,23,26,29,32,35,38,45,48,51,54,57,67-heptadecahydroxy-37-(2-hydroxy-2-iminoethyl)-50-(3-hydroxy-3-iminopropyl)-41,70-dimethyl-8-oxo-25-propan-2-yl-42,69,72-trithia-3,6,9,15,18,21,24,27,30,33,36,39,46,49,52,55,58,60,66-nonadecazapentacyclo[38.18.9.319,56.328,53.09,13]triheptaconta-2,5,14,17,20,23,26,29,32,35,38,45,48,51,54,57,66-heptadecaene-65-carboxylic acid Chemical compound CC(C)[C@@H]1\N=C(O)/[C@H](Cc2ccccc2)\N=C(O)/[C@@H]2\N=C(O)/[C@H](Cc3ccccc3)\N=C(O)/[C@@H]3CCCN3C(=O)C\N=C(O)/[C@H](Cc3ccccc3)\N=C(O)/[C@@H]3CNCCCC[C@H](\N=C(O)\[C@@H]4\N=C(O)\[C@H](CC(O)=N)\N=C(O)\C\N=C(O)/[C@@H](\N=C(O)\[C@H](CSC[C@@H](N=C(O)[C@H](CCC(O)=N)N=C(O)[C@H](CCCCN)N=C(O)[C@@H](N)CS[C@H]4C)C(O)=N[C@@H](CS[C@H]2C)C(O)=N3)\N=C1\O)[C@@H](O)C(O)=O)C(O)=O SFWLDKQAUHFCBS-AOEYGKNYSA-N 0.000 description 1
• KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
• DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
• MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
• PHOZOHFUXHPOCK-QMMMGPOBSA-N (2s)-2-ethyl-8-methyl-1-thia-4,8-diazaspiro[4.5]decan-3-one Chemical compound N1C(=O)[C@H](CC)SC11CCN(C)CC1 PHOZOHFUXHPOCK-QMMMGPOBSA-N 0.000 description 1
• SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
• HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 description 1
• ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
• OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
• JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
• IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
• LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical group OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• OOWQBDFWEXAXPB-IBGZPJMESA-N 1-O-hexadecyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)CO OOWQBDFWEXAXPB-IBGZPJMESA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
• FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
• 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
• 238000004293 19F NMR spectroscopy Methods 0.000 description 1
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• KEZNMOUMHOZFRA-UHFFFAOYSA-N 1h-pyrazol-4-ylboronic acid Chemical compound OB(O)C=1C=NNC=1 KEZNMOUMHOZFRA-UHFFFAOYSA-N 0.000 description 1
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• LSIXBBPOJBJQHN-UHFFFAOYSA-N 2,3-Dimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1C2 LSIXBBPOJBJQHN-UHFFFAOYSA-N 0.000 description 1
• MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical compound BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 1
• BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
• LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical compound ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
• FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 1
• GRXQKQOTJVCSLM-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=C2NC=CC2=CN=C1C=1C=NNC=1 GRXQKQOTJVCSLM-UHFFFAOYSA-N 0.000 description 1
• UZYQSNQJLWTICD-UHFFFAOYSA-N 2-(n-benzoylanilino)-2,2-dinitroacetic acid Chemical compound C=1C=CC=CC=1N(C(C(=O)O)([N+]([O-])=O)[N+]([O-])=O)C(=O)C1=CC=CC=C1 UZYQSNQJLWTICD-UHFFFAOYSA-N 0.000 description 1
• KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 1
• IJXJGQCXFSSHNL-UHFFFAOYSA-N 2-amino-2-phenylethanol Chemical compound OCC(N)C1=CC=CC=C1 IJXJGQCXFSSHNL-UHFFFAOYSA-N 0.000 description 1
• STHCPCIXAKDNOP-UHFFFAOYSA-N 2-amino-4,6-difluorophenol Chemical compound NC1=CC(F)=CC(F)=C1O STHCPCIXAKDNOP-UHFFFAOYSA-N 0.000 description 1
• ULDFRPKVIZMKJG-UHFFFAOYSA-N 2-amino-4-fluorophenol Chemical compound NC1=CC(F)=CC=C1O ULDFRPKVIZMKJG-UHFFFAOYSA-N 0.000 description 1
• BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
• KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
• HHQIHMBKTYWMIJ-UHFFFAOYSA-N 2-chloro-6-methyl-[1,3]oxazolo[5,4-b]pyridine Chemical compound CC1=CN=C2OC(Cl)=NC2=C1 HHQIHMBKTYWMIJ-UHFFFAOYSA-N 0.000 description 1
• KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
• HIGRXCJEFUYRNW-UHFFFAOYSA-N 2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C=CC=C1[N+]([O-])=O HIGRXCJEFUYRNW-UHFFFAOYSA-N 0.000 description 1
• AUVALWUPUHHNQV-UHFFFAOYSA-N 2-hydroxy-3-propylbenzoic acid Chemical class CCCC1=CC=CC(C(O)=O)=C1O AUVALWUPUHHNQV-UHFFFAOYSA-N 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• JUWSCPBRVFRPFT-UHFFFAOYSA-N 2-methylpropan-2-amine;hydrate Chemical compound O.CC(C)(C)N JUWSCPBRVFRPFT-UHFFFAOYSA-N 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
• BNBQQYFXBLBYJK-UHFFFAOYSA-N 2-pyridin-2-yl-1,3-oxazole Chemical compound C1=COC(C=2N=CC=CC=2)=N1 BNBQQYFXBLBYJK-UHFFFAOYSA-N 0.000 description 1
• HMFKFHLTUCJZJO-UHFFFAOYSA-N 2-{2-[3,4-bis(2-hydroxyethoxy)oxolan-2-yl]-2-(2-hydroxyethoxy)ethoxy}ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCC(OCCO)C1OCC(OCCO)C1OCCO HMFKFHLTUCJZJO-UHFFFAOYSA-N 0.000 description 1
• HJVKLVGLKNGYGQ-UHFFFAOYSA-N 20-methylhenicosanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCCCCCC(O)=O HJVKLVGLKNGYGQ-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• NRWMBHYHFFGEEC-MDZDMXLPSA-N 3-[(e)-octadec-9-enoxy]propane-1,2-diol Chemical compound CCCCCCCC\C=C\CCCCCCCCOCC(O)CO NRWMBHYHFFGEEC-MDZDMXLPSA-N 0.000 description 1
• OIIBRAGQGFLUFI-UHFFFAOYSA-N 3-amino-1h-pyridin-4-one Chemical compound NC1=CNC=CC1=O OIIBRAGQGFLUFI-UHFFFAOYSA-N 0.000 description 1
• LLMWKBGTHYWHGU-UHFFFAOYSA-N 3-amino-5-methyl-1h-pyridin-2-one Chemical compound CC1=CN=C(O)C(N)=C1 LLMWKBGTHYWHGU-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• GAWNBKUTBVLIPL-UHFFFAOYSA-N 3-fluoro-2-nitrophenol Chemical compound OC1=CC=CC(F)=C1[N+]([O-])=O GAWNBKUTBVLIPL-UHFFFAOYSA-N 0.000 description 1
• 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
• CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
• DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
• DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 1
• BPTCCCTWWAUJRK-UHFFFAOYSA-N 4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CN2 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 1
• 102100030310 5,6-dihydroxyindole-2-carboxylic acid oxidase Human genes 0.000 description 1
• 101710163881 5,6-dihydroxyindole-2-carboxylic acid oxidase Proteins 0.000 description 1
• LVMZMDMVDWIZAL-UHFFFAOYSA-N 5-amino-6-chloro-1h-pyrimidin-4-one Chemical compound NC1=C(Cl)NC=NC1=O LVMZMDMVDWIZAL-UHFFFAOYSA-N 0.000 description 1
• BOBIZYYFYLLRAH-UHFFFAOYSA-N 5-chloro-3h-1,3-benzoxazole-2-thione Chemical compound ClC1=CC=C2OC(S)=NC2=C1 BOBIZYYFYLLRAH-UHFFFAOYSA-N 0.000 description 1
• BLFUHTOZIOQGBU-UHFFFAOYSA-N 5-fluoro-3-nitro-1h-pyridin-2-one Chemical compound [O-][N+](=O)C1=CC(F)=CNC1=O BLFUHTOZIOQGBU-UHFFFAOYSA-N 0.000 description 1
• WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
• CMLCMPZIAVMYRQ-UHFFFAOYSA-N 6-methyl-1h-[1,3]oxazolo[5,4-b]pyridine-2-thione Chemical compound CC1=CN=C2OC(=S)NC2=C1 CMLCMPZIAVMYRQ-UHFFFAOYSA-N 0.000 description 1
• KQULXBZFTSJHJQ-UHFFFAOYSA-N 7-fluoro-3h-1,3-benzoxazole-2-thione Chemical compound FC1=CC=CC2=C1OC(S)=N2 KQULXBZFTSJHJQ-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 235000006491 Acacia senegal Nutrition 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• 206010027654 Allergic conditions Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• 229930183010 Amphotericin Natural products 0.000 description 1
• 235000019737 Animal fat Nutrition 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 241001553178 Arachis glabrata Species 0.000 description 1
• 206010053555 Arthritis bacterial Diseases 0.000 description 1
• 206010003267 Arthritis reactive Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000003950 B-cell lymphoma Diseases 0.000 description 1
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
• 108010001478 Bacitracin Proteins 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 235000021357 Behenic acid Nutrition 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 229940122739 Calcineurin inhibitor Drugs 0.000 description 1
• 101710192106 Calcineurin-binding protein cabin-1 Proteins 0.000 description 1
• 102100024123 Calcineurin-binding protein cabin-1 Human genes 0.000 description 1
• 229940127291 Calcium channel antagonist Drugs 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• 206010007279 Carcinoid tumour of the gastrointestinal tract Diseases 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• 208000005024 Castleman disease Diseases 0.000 description 1
• 229930186147 Cephalosporin Natural products 0.000 description 1
• 229920001661 Chitosan Polymers 0.000 description 1
• GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 208000018458 Colitis-Associated Neoplasms Diseases 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• 206010010099 Combined immunodeficiency Diseases 0.000 description 1
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
• MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
• 206010011219 Costochondritis Diseases 0.000 description 1
• 206010011715 Cyclitis Diseases 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 229930105110 Cyclosporin A Natural products 0.000 description 1
• DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
• DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 239000012623 DNA damaging agent Substances 0.000 description 1
• FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010012689 Diabetic retinopathy Diseases 0.000 description 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
• 101100256637 Drosophila melanogaster senju gene Proteins 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 206010015084 Episcleritis Diseases 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
• 102000003951 Erythropoietin Human genes 0.000 description 1
• 108090000394 Erythropoietin Proteins 0.000 description 1
• 108010008165 Etanercept Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• 229920003134 Eudragit® polymer Polymers 0.000 description 1
• 102100034719 Extracellular glycoprotein lacritin Human genes 0.000 description 1
• 229940124783 FAK inhibitor Drugs 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 208000001640 Fibromyalgia Diseases 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 108010091824 Focal Adhesion Kinase 1 Proteins 0.000 description 1
• 208000004262 Food Hypersensitivity Diseases 0.000 description 1
• 229930182566 Gentamicin Natural products 0.000 description 1
• CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
• 206010018341 Gliosis Diseases 0.000 description 1
• 206010018634 Gouty Arthritis Diseases 0.000 description 1
• 208000009329 Graft vs Host Disease Diseases 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 208000010496 Heart Arrest Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 208000032843 Hemorrhage Diseases 0.000 description 1
• 206010073069 Hepatic cancer Diseases 0.000 description 1
• 208000005176 Hepatitis C Diseases 0.000 description 1
• 101001090521 Homo sapiens Extracellular glycoprotein lacritin Proteins 0.000 description 1
• 101001133056 Homo sapiens Mucin-1 Proteins 0.000 description 1
• 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 description 1
• 238000006130 Horner-Wadsworth-Emmons olefination reaction Methods 0.000 description 1
• 241000598436 Human T-cell lymphotropic virus Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• 238000004566 IR spectroscopy Methods 0.000 description 1
• 108060003951 Immunoglobulin Proteins 0.000 description 1
• 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
• 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
• 108010000837 Janus Kinase 1 Proteins 0.000 description 1
• 108010019437 Janus Kinase 2 Proteins 0.000 description 1
• 108010019421 Janus Kinase 3 Proteins 0.000 description 1
• 208000003456 Juvenile Arthritis Diseases 0.000 description 1
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
• 208000007766 Kaposi sarcoma Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 239000005639 Lauric acid Substances 0.000 description 1
• ZCGOMHNNNFPNMX-YHYDXASRSA-N Levocabastinum Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)C2CCC(CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-YHYDXASRSA-N 0.000 description 1
• GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
• BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 241001237732 Microtia Species 0.000 description 1
• 102100034256 Mucin-1 Human genes 0.000 description 1
• 108010063954 Mucins Proteins 0.000 description 1
• 108010093825 Mucoproteins Proteins 0.000 description 1
• 102000001621 Mucoproteins Human genes 0.000 description 1
• 101100346764 Mus musculus Mtln gene Proteins 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 229940121743 Muscarinic receptor agonist Drugs 0.000 description 1
• 208000009525 Myocarditis Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• IJHNSHDBIRRJRN-UHFFFAOYSA-N N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=CC=C1 IJHNSHDBIRRJRN-UHFFFAOYSA-N 0.000 description 1
• FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• 229930193140 Neomycin Natural products 0.000 description 1
• 206010029113 Neovascularisation Diseases 0.000 description 1
• 239000004677 Nylon Substances 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 239000004100 Oxytetracycline Substances 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• 235000021314 Palmitic acid Nutrition 0.000 description 1
• 235000021319 Palmitoleic acid Nutrition 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
• 244000113945 Pinus torreyana Species 0.000 description 1
• 235000006235 Pinus torreyana Nutrition 0.000 description 1
• 102000004179 Plasminogen Activator Inhibitor 2 Human genes 0.000 description 1
• 108090000614 Plasminogen Activator Inhibitor 2 Proteins 0.000 description 1
• 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
• 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
• 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
• 229920002596 Polyethylene Glycol 900 Polymers 0.000 description 1
• 108010040201 Polymyxins Proteins 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
• 102000001744 Purinergic P2Y2 Receptors Human genes 0.000 description 1
• 108010029812 Purinergic P2Y2 Receptors Proteins 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 229940123690 Raf kinase inhibitor Drugs 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• ALLWOAVDORUJLA-UHFFFAOYSA-N Rebamipida Chemical compound C=1C(=O)NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)C1=CC=C(Cl)C=C1 ALLWOAVDORUJLA-UHFFFAOYSA-N 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• 206010038910 Retinitis Diseases 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
• 229910006124 SOCl2 Inorganic materials 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• 208000009359 Sezary Syndrome Diseases 0.000 description 1
• 208000021388 Sezary disease Diseases 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 101710173693 Short transient receptor potential channel 1 Proteins 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• 206010040880 Skin irritation Diseases 0.000 description 1
• 239000004115 Sodium Silicate Substances 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 229920002385 Sodium hyaluronate Polymers 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 229930182558 Sterol Natural products 0.000 description 1
• 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 description 1
• 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 241000282898 Sus scrofa Species 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• 238000006859 Swern oxidation reaction Methods 0.000 description 1
• 201000009594 Systemic Scleroderma Diseases 0.000 description 1
• 206010042953 Systemic sclerosis Diseases 0.000 description 1
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 102000036693 Thrombopoietin Human genes 0.000 description 1
• 108010041111 Thrombopoietin Proteins 0.000 description 1
• 208000024799 Thyroid disease Diseases 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 208000026317 Tietze syndrome Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• LVTKHGUGBGNBPL-UHFFFAOYSA-N Trp-P-1 Chemical compound N1C2=CC=CC=C2C2=C1C(C)=C(N)N=C2C LVTKHGUGBGNBPL-UHFFFAOYSA-N 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 206010046799 Uterine leiomyosarcoma Diseases 0.000 description 1
• 108010059993 Vancomycin Proteins 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• 206010047571 Visual impairment Diseases 0.000 description 1
• 239000004164 Wax ester Substances 0.000 description 1
• 229910021536 Zeolite Inorganic materials 0.000 description 1
• LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
• RRDRHWJDBOGQHN-JWCTVYNTSA-N [2-[(2s,5r,8s,11s,14r,17s,22s)-17-[(1r)-1-hydroxyethyl]-22-[[(2s)-2-[[(2s,3r)-3-hydroxy-2-[[(2s)-2-[6-methyloctanoyl(sulfomethyl)amino]-4-(sulfomethylamino)butanoyl]amino]butyl]amino]-4-(sulfomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15 Chemical compound CCC(C)CCCCC(=O)N(CS(O)(=O)=O)[C@@H](CCNCS(O)(=O)=O)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCNCS(O)(=O)=O)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CCNCS(O)(=O)=O)NC(=O)[C@H](CCNCS(O)(=O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCNCS(O)(=O)=O)NC1=O RRDRHWJDBOGQHN-JWCTVYNTSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 229940081735 acetylcellulose Drugs 0.000 description 1
• 229960004308 acetylcysteine Drugs 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000011149 active material Substances 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 238000005054 agglomeration Methods 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
• 150000008041 alkali metal carbonates Chemical class 0.000 description 1
• 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
• 150000004703 alkoxides Chemical class 0.000 description 1
• 125000004419 alkynylene group Chemical group 0.000 description 1
• 208000002029 allergic contact dermatitis Diseases 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 230000000172 allergic effect Effects 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
• 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
• DCAYPVUWAIABOU-UHFFFAOYSA-N alpha-n-hexadecene Natural products CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
• 230000001668 ameliorated effect Effects 0.000 description 1
• 150000001409 amidines Chemical class 0.000 description 1
• 229960004821 amikacin Drugs 0.000 description 1
• LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
• 229940126575 aminoglycoside Drugs 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 230000003444 anaesthetic effect Effects 0.000 description 1
• 229960004238 anakinra Drugs 0.000 description 1
• 230000019552 anatomical structure morphogenesis Effects 0.000 description 1
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 230000003042 antagnostic effect Effects 0.000 description 1
• REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 description 1
• 229960002469 antazoline Drugs 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000843 anti-fungal effect Effects 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 239000000043 antiallergic agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 229940114079 arachidonic acid Drugs 0.000 description 1
• 235000021342 arachidonic acid Nutrition 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 208000037875 astrocytosis Diseases 0.000 description 1
• 230000007341 astrogliosis Effects 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• 125000003943 azolyl group Chemical group 0.000 description 1
• 229960003071 bacitracin Drugs 0.000 description 1
• 229930184125 bacitracin Natural products 0.000 description 1
• CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
• 229940116226 behenic acid Drugs 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• 230000031018 biological processes and functions Effects 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000000740 bleeding effect Effects 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• 229910021538 borax Inorganic materials 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 239000007853 buffer solution Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 239000000480 calcium channel blocker Substances 0.000 description 1
• BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
• 239000000292 calcium oxide Substances 0.000 description 1
• ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 239000000378 calcium silicate Substances 0.000 description 1
• 229910052918 calcium silicate Inorganic materials 0.000 description 1
• 229960003340 calcium silicate Drugs 0.000 description 1
• 235000012241 calcium silicate Nutrition 0.000 description 1
• OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 229960001777 castor oil Drugs 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 229940124587 cephalosporin Drugs 0.000 description 1
• 150000001780 cephalosporins Chemical class 0.000 description 1
• 229960005395 cetuximab Drugs 0.000 description 1
• JQXXHWHPUNPDRT-BQVAUQFYSA-N chembl1523493 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2C=NN1CCN(C)CC1 JQXXHWHPUNPDRT-BQVAUQFYSA-N 0.000 description 1
• HJWLJNBZVZDLAQ-HAQNSBGRSA-N chembl2103874 Chemical compound C1C[C@@H](CS(=O)(=O)NC)CC[C@@H]1N(C)C1=NC=NC2=C1C=CN2 HJWLJNBZVZDLAQ-HAQNSBGRSA-N 0.000 description 1
• OOWQBDFWEXAXPB-UHFFFAOYSA-N chimyl alcohol Natural products CCCCCCCCCCCCCCCCOCC(O)CO OOWQBDFWEXAXPB-UHFFFAOYSA-N 0.000 description 1
• 229960005091 chloramphenicol Drugs 0.000 description 1
• WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
• 229960003260 chlorhexidine Drugs 0.000 description 1
• 229940107161 cholesterol Drugs 0.000 description 1
• 239000000064 cholinergic agonist Substances 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 201000010902 chronic myelomonocytic leukemia Diseases 0.000 description 1
• 229960003405 ciprofloxacin Drugs 0.000 description 1
• SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
• 230000010405 clearance mechanism Effects 0.000 description 1
• 238000011260 co-administration Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 229940108538 colistimethate Drugs 0.000 description 1
• 108700028201 colistinmethanesulfonic acid Proteins 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• 239000012059 conventional drug carrier Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• 229960004544 cortisone Drugs 0.000 description 1
• QTCANKDTWWSCMR-UHFFFAOYSA-N costic aldehyde Natural products C1CCC(=C)C2CC(C(=C)C=O)CCC21C QTCANKDTWWSCMR-UHFFFAOYSA-N 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 229960000265 cromoglicic acid Drugs 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960003077 cycloserine Drugs 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 230000007850 degeneration Effects 0.000 description 1
• FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
• 239000008367 deionised water Substances 0.000 description 1
• 229910021641 deionized water Inorganic materials 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 229960001259 diclofenac Drugs 0.000 description 1
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
• ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
• 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
• 235000019797 dipotassium phosphate Nutrition 0.000 description 1
• VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 1
• BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
• 229910000397 disodium phosphate Inorganic materials 0.000 description 1
• 235000019800 disodium phosphate Nutrition 0.000 description 1
• DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
• 229960000735 docosanol Drugs 0.000 description 1
• LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 210000003717 douglas' pouch Anatomy 0.000 description 1
• 229960003722 doxycycline Drugs 0.000 description 1
• 238000009509 drug development Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 108010067071 duramycin Proteins 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• IWCWQNVIUXZOMJ-MISYRCLQSA-N ecabet Chemical compound OC(=O)[C@@](C)([C@@H]1CC2)CCC[C@]1(C)C1=C2C=C(C(C)C)C(S(O)(=O)=O)=C1 IWCWQNVIUXZOMJ-MISYRCLQSA-N 0.000 description 1
• 229950003246 ecabet Drugs 0.000 description 1
• 229940124274 edetate disodium Drugs 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 229960000284 efalizumab Drugs 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000012156 elution solvent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 150000002085 enols Chemical class 0.000 description 1
• 229960002549 enoxacin Drugs 0.000 description 1
• IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 229960002179 ephedrine Drugs 0.000 description 1
• 229960001433 erlotinib Drugs 0.000 description 1
• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 1
• DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
• 210000003743 erythrocyte Anatomy 0.000 description 1
• 229940105423 erythropoietin Drugs 0.000 description 1
• 229960000403 etanercept Drugs 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 238000007046 ethoxylation reaction Methods 0.000 description 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
• 229940093476 ethylene glycol Drugs 0.000 description 1
• STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 229960005420 etoposide Drugs 0.000 description 1
• 230000005713 exacerbation Effects 0.000 description 1
• 239000003172 expectorant agent Substances 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 206010016256 fatigue Diseases 0.000 description 1
• 150000002194 fatty esters Chemical class 0.000 description 1
• 230000004761 fibrosis Effects 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000012054 flavored emulsion Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000020375 flavoured syrup Nutrition 0.000 description 1
• 238000007667 floating Methods 0.000 description 1
• 229960004884 fluconazole Drugs 0.000 description 1
• RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
• 229960004413 flucytosine Drugs 0.000 description 1
• 229940043075 fluocinolone Drugs 0.000 description 1
• 229960001347 fluocinolone acetonide Drugs 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229960001048 fluorometholone Drugs 0.000 description 1
• FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 229940124307 fluoroquinolone Drugs 0.000 description 1
• 229960002390 flurbiprofen Drugs 0.000 description 1
• SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000020932 food allergy Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 238000010575 fractional recrystallization Methods 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 1
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000001879 gelation Methods 0.000 description 1
• 208000005017 glioblastoma Diseases 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 208000024908 graft versus host disease Diseases 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 229910052735 hafnium Inorganic materials 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 210000003128 head Anatomy 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 230000003862 health status Effects 0.000 description 1
• 229910052734 helium Inorganic materials 0.000 description 1
• 230000002489 hematologic effect Effects 0.000 description 1
• 208000002672 hepatitis B Diseases 0.000 description 1
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 229920002674 hyaluronan Polymers 0.000 description 1
• 229960003160 hyaluronic acid Drugs 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• 239000008309 hydrophilic cream Substances 0.000 description 1
• XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
• 229960004171 hydroxychloroquine Drugs 0.000 description 1
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
• 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 208000014796 hyper-IgE recurrent infection syndrome 1 Diseases 0.000 description 1
• 206010051040 hyper-IgE syndrome Diseases 0.000 description 1
• 230000007954 hypoxia Effects 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 230000008629 immune suppression Effects 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 102000018358 immunoglobulin Human genes 0.000 description 1
• 230000001861 immunosuppressant effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000010874 in vitro model Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000007914 intraventricular administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• ISTFUJWTQAMRGA-UHFFFAOYSA-N iso-beta-costal Natural products C1C(C(=C)C=O)CCC2(C)CCCC(C)=C21 ISTFUJWTQAMRGA-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 229960000318 kanamycin Drugs 0.000 description 1
• 229930027917 kanamycin Natural products 0.000 description 1
• SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
• 229930182823 kanamycin A Natural products 0.000 description 1
• 229960004125 ketoconazole Drugs 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 229960004752 ketorolac Drugs 0.000 description 1
• OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 150000003951 lactams Chemical class 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• SFWLDKQAUHFCBS-WWXQEMPQSA-N lancovutide Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H]2C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@@H](CCCCNC[C@H]4C(=O)N[C@@H](CC=5C=CC=CC=5)C(=O)NCC(=O)N5CCC[C@H]5C(=O)N[C@@H](CC=5C=CC=CC=5)C(=O)N[C@H]([C@@H](SC[C@H](NC(=O)[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CSC3C)CSC2)C(=O)N4)C)C(=O)N1)C(O)=O)[C@@H](O)C(O)=O)=O)C(C)C)C1=CC=CC=C1 SFWLDKQAUHFCBS-WWXQEMPQSA-N 0.000 description 1
• GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 229960003376 levofloxacin Drugs 0.000 description 1
• 125000005647 linker group Chemical group 0.000 description 1
• 229960004488 linolenic acid Drugs 0.000 description 1
• KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
• JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 239000011344 liquid material Substances 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• RVGLGHVJXCETIO-UHFFFAOYSA-N lodoxamide Chemical compound OC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(O)=O)=C1Cl RVGLGHVJXCETIO-UHFFFAOYSA-N 0.000 description 1
• 229960004305 lodoxamide Drugs 0.000 description 1
• 229960002422 lomefloxacin Drugs 0.000 description 1
• ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 description 1
• 229960003744 loteprednol etabonate Drugs 0.000 description 1
• DMKSVUSAATWOCU-HROMYWEYSA-N loteprednol etabonate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)OCCl)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O DMKSVUSAATWOCU-HROMYWEYSA-N 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 230000001050 lubricating effect Effects 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 230000036244 malformation Effects 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 230000035800 maturation Effects 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 229910021645 metal ion Inorganic materials 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229960002509 miconazole Drugs 0.000 description 1
• 230000000813 microbial effect Effects 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 239000011859 microparticle Substances 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000003032 molecular docking Methods 0.000 description 1
• 229940066491 mucolytics Drugs 0.000 description 1
• 210000004400 mucous membrane Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 239000000472 muscarinic agonist Substances 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 206010028417 myasthenia gravis Diseases 0.000 description 1
• DOZYTHNHLLSNIK-JOKMOOFLSA-M mycophenolate sodium Chemical compound [Na+].OC1=C(C\C=C(/C)CCC([O-])=O)C(OC)=C(C)C2=C1C(=O)OC2 DOZYTHNHLLSNIK-JOKMOOFLSA-M 0.000 description 1
• 229960000951 mycophenolic acid Drugs 0.000 description 1
• OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 229940073569 n-methylephedrine Drugs 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960005016 naphazoline Drugs 0.000 description 1
• 229960003255 natamycin Drugs 0.000 description 1
• 239000004311 natamycin Substances 0.000 description 1
• 235000010298 natamycin Nutrition 0.000 description 1
• NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 210000003739 neck Anatomy 0.000 description 1
• 229960004927 neomycin Drugs 0.000 description 1
• ZBGPYVZLYBDXKO-HILBYHGXSA-N netilmycin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@]([C@H](NC)[C@@H](O)CO1)(C)O)NCC)[C@H]1OC(CN)=CC[C@H]1N ZBGPYVZLYBDXKO-HILBYHGXSA-N 0.000 description 1
• 230000004770 neurodegeneration Effects 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 239000002736 nonionic surfactant Substances 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 229960001180 norfloxacin Drugs 0.000 description 1
• OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
• 125000005482 norpinyl group Chemical group 0.000 description 1
• 229920001778 nylon Polymers 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
• 229960002446 octanoic acid Drugs 0.000 description 1
• 229960001699 ofloxacin Drugs 0.000 description 1
• 239000012053 oil suspension Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229960002969 oleic acid Drugs 0.000 description 1
• 235000021313 oleic acid Nutrition 0.000 description 1
• 229940055577 oleyl alcohol Drugs 0.000 description 1
• XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000012074 organic phase Substances 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229960000625 oxytetracycline Drugs 0.000 description 1
• IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
• 235000019366 oxytetracycline Nutrition 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 238000005192 partition Methods 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000010412 perfusion Effects 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 229960001190 pheniramine Drugs 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
• 229960000395 phenylpropanolamine Drugs 0.000 description 1
• 108700021017 phosphatidylethanolamine binding protein Proteins 0.000 description 1
• 102000051624 phosphatidylethanolamine binding protein Human genes 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 229960001416 pilocarpine Drugs 0.000 description 1
• KASDHRXLYQOAKZ-ZPSXYTITSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-ZPSXYTITSA-N 0.000 description 1
• 229960005330 pimecrolimus Drugs 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229920000962 poly(amidoamine) Polymers 0.000 description 1
• 229920000747 poly(lactic acid) Polymers 0.000 description 1
• 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
• 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
• 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
• 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
• 229940094543 polyethylene glycol 900 Drugs 0.000 description 1
• 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
• 238000006116 polymerization reaction Methods 0.000 description 1
• 229920001299 polypropylene fumarate Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 229920000136 polysorbate Polymers 0.000 description 1
• 229950008882 polysorbate Drugs 0.000 description 1
• 229920002635 polyurethane Polymers 0.000 description 1
• 239000004814 polyurethane Substances 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
• 229960002847 prasterone Drugs 0.000 description 1
• 229960005205 prednisolone Drugs 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• ZVOCIIHCJJEFRQ-BHXBHYJPSA-N propan-2-yl (5s,8e,10e,12r)-5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate Chemical compound CC(C)OC(=O)CCC[C@H](O)C#C\C=C\C=C\[C@H](O)CC#C ZVOCIIHCJJEFRQ-BHXBHYJPSA-N 0.000 description 1
• OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical compound CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 230000005588 protonation Effects 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• GHFGOVUYCKZOJH-UHFFFAOYSA-N pyridine-2,3-dicarbonitrile Chemical compound N#CC1=CC=CN=C1C#N GHFGOVUYCKZOJH-UHFFFAOYSA-N 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 208000002574 reactive arthritis Diseases 0.000 description 1
• 229950004535 rebamipide Drugs 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 229940075993 receptor modulator Drugs 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 231100001019 reduced numbers of red blood cells Toxicity 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000009711 regulatory function Effects 0.000 description 1
• 230000029058 respiratory gaseous exchange Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 229940120975 revlimid Drugs 0.000 description 1
• 238000000518 rheometry Methods 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 229960001225 rifampicin Drugs 0.000 description 1
• 229960001487 rimexolone Drugs 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229960004641 rituximab Drugs 0.000 description 1
• XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
• 229950010764 rivoglitazone Drugs 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 210000003786 sclera Anatomy 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000000580 secretagogue effect Effects 0.000 description 1
• NRWMBHYHFFGEEC-UHFFFAOYSA-N selachyl alcohol Natural products CCCCCCCCC=CCCCCCCCCOCC(O)CO NRWMBHYHFFGEEC-UHFFFAOYSA-N 0.000 description 1
• 239000012363 selectfluor Substances 0.000 description 1
• 239000012056 semi-solid material Substances 0.000 description 1
• 230000036303 septic shock Effects 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 208000002491 severe combined immunodeficiency Diseases 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 229920002545 silicone oil Polymers 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 230000036556 skin irritation Effects 0.000 description 1
• 231100000475 skin irritation Toxicity 0.000 description 1
• 231100000046 skin rash Toxicity 0.000 description 1
• 201000002314 small intestine cancer Diseases 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 229960002668 sodium chloride Drugs 0.000 description 1
• UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
• 229960002218 sodium chlorite Drugs 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000011083 sodium citrates Nutrition 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 229940010747 sodium hyaluronate Drugs 0.000 description 1
• 239000001540 sodium lactate Substances 0.000 description 1
• 235000011088 sodium lactate Nutrition 0.000 description 1
• 229940005581 sodium lactate Drugs 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 229910000162 sodium phosphate Inorganic materials 0.000 description 1
• 235000011008 sodium phosphates Nutrition 0.000 description 1
• NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
• 229910052911 sodium silicate Inorganic materials 0.000 description 1
• 235000010339 sodium tetraborate Nutrition 0.000 description 1
• YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000002798 spectrophotometry method Methods 0.000 description 1
• FOEYMRPOKBCNCR-UHFFFAOYSA-N spiro[2.5]octane Chemical compound C1CC11CCCCC1 FOEYMRPOKBCNCR-UHFFFAOYSA-N 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 239000012058 sterile packaged powder Substances 0.000 description 1
• 230000003637 steroidlike Effects 0.000 description 1
• 150000003432 sterols Chemical class 0.000 description 1
• 235000003702 sterols Nutrition 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 210000000434 stratum corneum Anatomy 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000005846 sugar alcohols Polymers 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 125000000542 sulfonic acid group Chemical group 0.000 description 1
• 229960004492 suprofen Drugs 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 229960001967 tacrolimus Drugs 0.000 description 1
• QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
• DWLADVOODHZCFV-UHFFFAOYSA-N tert-butyl 3-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)C1 DWLADVOODHZCFV-UHFFFAOYSA-N 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 229960003604 testosterone Drugs 0.000 description 1
• 229960002180 tetracycline Drugs 0.000 description 1
• 229930101283 tetracycline Natural products 0.000 description 1
• 229940040944 tetracyclines Drugs 0.000 description 1
• TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• VZOVVMIOZZLKAX-UHFFFAOYSA-N thieno[2,3-c]pyridine-4-carbonitrile Chemical compound S1C=CC2=C1C=NC=C2C#N VZOVVMIOZZLKAX-UHFFFAOYSA-N 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• 229960000707 tobramycin Drugs 0.000 description 1
• NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 229960005294 triamcinolone Drugs 0.000 description 1
• GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
• RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
• 235000019798 tripotassium phosphate Nutrition 0.000 description 1
• BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 229960000497 trovafloxacin Drugs 0.000 description 1
• WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
• 230000004565 tumor cell growth Effects 0.000 description 1
• 230000005740 tumor formation Effects 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 230000007306 turnover Effects 0.000 description 1
• 238000009827 uniform distribution Methods 0.000 description 1
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
• 229960003165 vancomycin Drugs 0.000 description 1
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
• 235000019871 vegetable fat Nutrition 0.000 description 1
• 239000012178 vegetable wax Substances 0.000 description 1
• 229940099039 velcade Drugs 0.000 description 1
• 229940055059 vexol Drugs 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 239000004034 viscosity adjusting agent Substances 0.000 description 1
• 230000004304 visual acuity Effects 0.000 description 1
• 229960005289 voclosporin Drugs 0.000 description 1
• BICRTLVBTLFLRD-PTWUADNWSA-N voclosporin Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C=C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O BICRTLVBTLFLRD-PTWUADNWSA-N 0.000 description 1
• 108010057559 voclosporin Proteins 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 235000019386 wax ester Nutrition 0.000 description 1
• 238000001238 wet grinding Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000010457 zeolite Substances 0.000 description 1
• YKPUWZUDDOIDPM-VURMDHGXSA-N zucapsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C/C(C)C)=CC=C1O YKPUWZUDDOIDPM-VURMDHGXSA-N 0.000 description 1
• 229960002860 zucapsaicin Drugs 0.000 description 1
• 150000003952 β-lactams Chemical class 0.000 description 1
• PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1