HRP20020696A2 - 3-aminoquinazolin-2,4-dione antibakterial agents - Google Patents

3-aminoquinazolin-2,4-dione antibakterial agents Download PDF

Info

Publication number: HRP20020696A2
Authority: HR; Croatia
Prior art keywords: amino; cyclopropyl; dione; fluoro; quinazoline
Prior art date: 2000-01-24

Application number

HR20020696A

Other languages

English (en)

Croatian (hr)

Inventor

Paul Bird

Edmund Lee Ellsworth

Dai Quoc Nguyen

Joseph Peter Sanchez

Howard Daniel Hollis Showalter

Rajeshwar Singh

Michael Andrew Stier

Tuan Phong Tran

Brian Morgan Watson

Judy Yip

Original Assignee

Warner Lambert Co

Priority date (The priority date 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 date listed.)

2000-01-24

Filing date

2002-08-23

Publication date

2003-12-31

2002-08-23 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2003-12-31 Publication of HRP20020696A2 publication Critical patent/HRP20020696A2/hr

Links

NMGODFWGUBLTTA-UHFFFAOYSA-N 3-amino-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(N)C(=O)NC2=C1 NMGODFWGUBLTTA-UHFFFAOYSA-N 0.000 title description 14
-1 where n is 0 or 1 Chemical group 0.000 claims description 366
238000000034 method Methods 0.000 claims description 353
150000001875 compounds Chemical class 0.000 claims description 287
125000000623 heterocyclic group Chemical group 0.000 claims description 48
125000003118 aryl group Chemical group 0.000 claims description 46
125000000547 substituted alkyl group Chemical group 0.000 claims description 42
125000005843 halogen group Chemical group 0.000 claims description 33
125000001072 heteroaryl group Chemical group 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 31
125000005017 substituted alkenyl group Chemical group 0.000 claims description 31
125000004426 substituted alkynyl group Chemical group 0.000 claims description 31
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 23
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 23
241000124008 Mammalia Species 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
239000004202 carbamide Substances 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 13
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 12
208000035143 Bacterial infection Diseases 0.000 claims description 11
208000022362 bacterial infectious disease Diseases 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 10
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000003107 substituted aryl group Chemical group 0.000 claims description 9
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
108010054814 DNA Gyrase Proteins 0.000 claims description 7
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
ZRLLSDAIVJNZMQ-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 ZRLLSDAIVJNZMQ-UHFFFAOYSA-N 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
SPECGCDSMBDLBR-UHFFFAOYSA-N 1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidine-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)=O)C1 SPECGCDSMBDLBR-UHFFFAOYSA-N 0.000 claims description 4
WTYPWMXNMZPJCE-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)azetidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C1 WTYPWMXNMZPJCE-UHFFFAOYSA-N 0.000 claims description 4
JASKKDJDJMQUCW-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)CC1 JASKKDJDJMQUCW-UHFFFAOYSA-N 0.000 claims description 4
REQQVRNKRVUMLG-UHFFFAOYSA-N 1-(3-amino-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl REQQVRNKRVUMLG-UHFFFAOYSA-N 0.000 claims description 3
NUZLMAGOIPFPSG-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)O)C1 NUZLMAGOIPFPSG-UHFFFAOYSA-N 0.000 claims description 3
XJPMPMISIRYKGH-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(C)(C)O)C1 XJPMPMISIRYKGH-UHFFFAOYSA-N 0.000 claims description 3
IXDMETOHGBEQQB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1C2C(N)C2CN1C(C(=CC=1C(=O)N(N)C2=O)F)=NC=1N2C1CC1 IXDMETOHGBEQQB-UHFFFAOYSA-N 0.000 claims description 3
LFARSGUVNIPJGM-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(CN)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 LFARSGUVNIPJGM-UHFFFAOYSA-N 0.000 claims description 3
YWYGZFKUTIQGCL-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-(3-hydroxyiminopyrrolidin-1-yl)quinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(CC3)=NO)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 YWYGZFKUTIQGCL-UHFFFAOYSA-N 0.000 claims description 3
CLKAGUACIOUJAC-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-7-(2,7-diazaspiro[4.4]nonan-2-yl)-6-fluoroquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC4(CNCC4)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 CLKAGUACIOUJAC-UHFFFAOYSA-N 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
PFSZPRDGUQBIJS-LURJTMIESA-N 3,5-diamino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C(N)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F PFSZPRDGUQBIJS-LURJTMIESA-N 0.000 claims description 2
OLCPOZCJEAXMFQ-UHFFFAOYSA-N 3,8-diamino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-methylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C1=CC(C)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1N OLCPOZCJEAXMFQ-UHFFFAOYSA-N 0.000 claims description 2
HKNHNFKDEOQGLZ-UHFFFAOYSA-N 3,8-diamino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C1=C(F)C(C)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1N HKNHNFKDEOQGLZ-UHFFFAOYSA-N 0.000 claims description 2
GTRJJQDFRZCWKQ-NXEZZACHSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[(3r)-3-[(1r)-1-(methylamino)ethyl]pyrrolidin-1-yl]pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H]([C@@H](C)NC)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 GTRJJQDFRZCWKQ-NXEZZACHSA-N 0.000 claims description 2
KGBQXGXVBHFICV-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CNC(C)C)C1 KGBQXGXVBHFICV-UHFFFAOYSA-N 0.000 claims description 2
VLVSORUTOYXYIG-UHFFFAOYSA-N 3-amino-7-(2-amino-5-azaspiro[2.4]heptan-5-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC21CC2N VLVSORUTOYXYIG-UHFFFAOYSA-N 0.000 claims description 2
QBAYAKOQUGQOHL-UHFFFAOYSA-N 3-amino-7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(N)C1 QBAYAKOQUGQOHL-UHFFFAOYSA-N 0.000 claims description 2
ONJJNQNMGCKRBJ-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(N)C1=CC=CC=C1 ONJJNQNMGCKRBJ-UHFFFAOYSA-N 0.000 claims description 2
NICJESYMFMNVRX-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(N)(CC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 NICJESYMFMNVRX-UHFFFAOYSA-N 0.000 claims description 2
MYNASXNPNLIHST-UHFFFAOYSA-N 3-amino-7-(3-amino-4-fluoropyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C(F)C1 MYNASXNPNLIHST-UHFFFAOYSA-N 0.000 claims description 2
LMKZWBWISAEVOS-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC LMKZWBWISAEVOS-UHFFFAOYSA-N 0.000 claims description 2
SQVTZXOBPCVCIL-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SQVTZXOBPCVCIL-UHFFFAOYSA-N 0.000 claims description 2
RHLHZJMDAZKSES-UHFFFAOYSA-N 3-amino-7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C1 RHLHZJMDAZKSES-UHFFFAOYSA-N 0.000 claims description 2
VPDDXYVQSVBBMT-UHFFFAOYSA-N 3-amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(N)C1 VPDDXYVQSVBBMT-UHFFFAOYSA-N 0.000 claims description 2
SMRJEBDYHBYSSD-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-2,4-dioxoquinazoline-8-carbonitrile Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C#N SMRJEBDYHBYSSD-UHFFFAOYSA-N 0.000 claims description 2
YKTNCTISKOJENP-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione Chemical compound O=C1N(N)C(=O)C=2C(C)=C(F)C(N3CC(N)CC3)=CC=2N1C1CC1 YKTNCTISKOJENP-UHFFFAOYSA-N 0.000 claims description 2
JFMXVEXEGIJVCH-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 JFMXVEXEGIJVCH-UHFFFAOYSA-N 0.000 claims description 2
APNFNASNMSAHKF-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(N)C1 APNFNASNMSAHKF-UHFFFAOYSA-N 0.000 claims description 2
MBXPBQAHLCCZOV-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoroquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OCC)=C1N1CCC(N)C1 MBXPBQAHLCCZOV-UHFFFAOYSA-N 0.000 claims description 2
NLGWNSVFUWNXQX-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoro-6-methoxyquinazoline-2,4-dione Chemical compound COC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(F)=C1N1CCC(N)C1 NLGWNSVFUWNXQX-UHFFFAOYSA-N 0.000 claims description 2
AEVLVLQRERPDHR-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F AEVLVLQRERPDHR-UHFFFAOYSA-N 0.000 claims description 2
GXQRPAGCOKWOTA-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-6-chloro-1-cyclopropyl-8-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(Cl)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F GXQRPAGCOKWOTA-UHFFFAOYSA-N 0.000 claims description 2
LXAOHWSBPOQFAW-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-(cyclobutylamino)-6-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CCC3)C2=C1Cl LXAOHWSBPOQFAW-UHFFFAOYSA-N 0.000 claims description 2
IZSIJRQLAKGNBV-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl IZSIJRQLAKGNBV-UHFFFAOYSA-N 0.000 claims description 2
GKVGMICZIRZYHZ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-6-fluoro-1-propan-2-ylquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(C(C)C)C2=C(Cl)C=1N1CCC(N)C1 GKVGMICZIRZYHZ-UHFFFAOYSA-N 0.000 claims description 2
UFFBMSWIXMBGJA-UHFFFAOYSA-N 3-amino-7-(4-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)CC1 UFFBMSWIXMBGJA-UHFFFAOYSA-N 0.000 claims description 2
USGOLBXMHMCSCB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 USGOLBXMHMCSCB-UHFFFAOYSA-N 0.000 claims description 2
SETCPIXEEMNUEB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C2C(N)C2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 SETCPIXEEMNUEB-UHFFFAOYSA-N 0.000 claims description 2
FZFXKOVOWBGKLJ-GFCCVEGCSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione Chemical compound C1[C@H](C(C)(N)C)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F FZFXKOVOWBGKLJ-GFCCVEGCSA-N 0.000 claims description 2
UOCLUTIPDCTUDR-SECBINFHSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H](C(C)(N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 UOCLUTIPDCTUDR-SECBINFHSA-N 0.000 claims description 2
GSIKINSTFPRFLI-SNVBAGLBSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-ethyl-6-fluoroquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(CC)C2=CC=1N1CC[C@@H](C(C)(C)N)C1 GSIKINSTFPRFLI-SNVBAGLBSA-N 0.000 claims description 2
JGYNWRYCSYCVFZ-ABAIWWIYSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JGYNWRYCSYCVFZ-ABAIWWIYSA-N 0.000 claims description 2
DGGJUSQBQMQVCO-WBMJQRKESA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DGGJUSQBQMQVCO-WBMJQRKESA-N 0.000 claims description 2
WAKUORIXGDVWOW-KUHUBIRLSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WAKUORIXGDVWOW-KUHUBIRLSA-N 0.000 claims description 2
QWFJOUZUSNZNMP-QRWLVFNGSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 QWFJOUZUSNZNMP-QRWLVFNGSA-N 0.000 claims description 2
JWSVHFMSXBFEGF-IAQYHMDHSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JWSVHFMSXBFEGF-IAQYHMDHSA-N 0.000 claims description 2
HTJVBSQZMOTMTA-MLGOLLRUSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HTJVBSQZMOTMTA-MLGOLLRUSA-N 0.000 claims description 2
JGYNWRYCSYCVFZ-IAQYHMDHSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JGYNWRYCSYCVFZ-IAQYHMDHSA-N 0.000 claims description 2
DGGJUSQBQMQVCO-MLGOLLRUSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DGGJUSQBQMQVCO-MLGOLLRUSA-N 0.000 claims description 2
WAKUORIXGDVWOW-AUUYWEPGSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WAKUORIXGDVWOW-AUUYWEPGSA-N 0.000 claims description 2
QWFJOUZUSNZNMP-FOIQADDNSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 QWFJOUZUSNZNMP-FOIQADDNSA-N 0.000 claims description 2
JWSVHFMSXBFEGF-ABAIWWIYSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JWSVHFMSXBFEGF-ABAIWWIYSA-N 0.000 claims description 2
HTJVBSQZMOTMTA-WBMJQRKESA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HTJVBSQZMOTMTA-WBMJQRKESA-N 0.000 claims description 2
PWBWMMRYCDDDSD-DTWKUNHWSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 PWBWMMRYCDDDSD-DTWKUNHWSA-N 0.000 claims description 2
DLJALTOFOUWOSY-AAEUAGOBSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@H](F)[C@@H](C(C)(C)N)C1 DLJALTOFOUWOSY-AAEUAGOBSA-N 0.000 claims description 2
PSKJYUUFNGTWRT-JSGCOSHPSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1C[C@H](F)[C@@H](C(C)(C)N)C1 PSKJYUUFNGTWRT-JSGCOSHPSA-N 0.000 claims description 2
SFTNKLNSKHZSIS-STQMWFEESA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SFTNKLNSKHZSIS-STQMWFEESA-N 0.000 claims description 2
SZRPGPJRTBWAQC-KBPBESRZSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SZRPGPJRTBWAQC-KBPBESRZSA-N 0.000 claims description 2
FQEJJUYPFJSYTM-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FQEJJUYPFJSYTM-AEGPPILISA-N 0.000 claims description 2
WCWSUFKBVHIJCI-CWRNSKLLSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WCWSUFKBVHIJCI-CWRNSKLLSA-N 0.000 claims description 2
BIXIMKDTYJERQW-SOUVJXGZSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC BIXIMKDTYJERQW-SOUVJXGZSA-N 0.000 claims description 2
QCDOITHYWYGQQG-HRCADAONSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QCDOITHYWYGQQG-HRCADAONSA-N 0.000 claims description 2
WSNNNRWCTBIJLR-HZUKXOBISA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WSNNNRWCTBIJLR-HZUKXOBISA-N 0.000 claims description 2
JMZBLZXEJZISCQ-XNJJOIOASA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JMZBLZXEJZISCQ-XNJJOIOASA-N 0.000 claims description 2
WTYRDLVCSKPCMR-VBNZEHGJSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WTYRDLVCSKPCMR-VBNZEHGJSA-N 0.000 claims description 2
NIHCENZIYVQPQI-AFAVFJNCSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NIHCENZIYVQPQI-AFAVFJNCSA-N 0.000 claims description 2
RMERSVKMJNOJBM-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RMERSVKMJNOJBM-AEGPPILISA-N 0.000 claims description 2
YVNCLSOUFPUSBG-CWRNSKLLSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YVNCLSOUFPUSBG-CWRNSKLLSA-N 0.000 claims description 2
MOZUHBQCTICBJN-SOUVJXGZSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MOZUHBQCTICBJN-SOUVJXGZSA-N 0.000 claims description 2
WMMXZMSWPCDHCH-HRCADAONSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WMMXZMSWPCDHCH-HRCADAONSA-N 0.000 claims description 2
JNBFVIXMWYHESF-HZUKXOBISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JNBFVIXMWYHESF-HZUKXOBISA-N 0.000 claims description 2
FVHCULAQBOQUHE-XNJJOIOASA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FVHCULAQBOQUHE-XNJJOIOASA-N 0.000 claims description 2
WXEULHODWRFMJL-VBNZEHGJSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WXEULHODWRFMJL-VBNZEHGJSA-N 0.000 claims description 2
YMLACVZZOGDLOE-AFAVFJNCSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YMLACVZZOGDLOE-AFAVFJNCSA-N 0.000 claims description 2
KAYKDFPFMATDAL-FPMFFAJLSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC KAYKDFPFMATDAL-FPMFFAJLSA-N 0.000 claims description 2
BXAJEQNNGNFGRI-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXAJEQNNGNFGRI-AEGPPILISA-N 0.000 claims description 2
FINKNCVICOYUPZ-MELADBBJSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FINKNCVICOYUPZ-MELADBBJSA-N 0.000 claims description 2
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HWEFAWYJNKYDOP-VZJVUDMVSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC HWEFAWYJNKYDOP-VZJVUDMVSA-N 0.000 claims description 2
CQINKMNYHQLMPR-JMPLFQLZSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CQINKMNYHQLMPR-JMPLFQLZSA-N 0.000 claims description 2
JUHGKXCYUJZZLC-TUKIKUTGSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JUHGKXCYUJZZLC-TUKIKUTGSA-N 0.000 claims description 2
QTWRUBAFBNVEBZ-KNXALSJPSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QTWRUBAFBNVEBZ-KNXALSJPSA-N 0.000 claims description 2
DLJALTOFOUWOSY-WCQYABFASA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@@H](C(C)(C)N)C1 DLJALTOFOUWOSY-WCQYABFASA-N 0.000 claims description 2
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SZRPGPJRTBWAQC-UONOGXRCSA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SZRPGPJRTBWAQC-UONOGXRCSA-N 0.000 claims description 2
KCNSFBLKYSGMEW-LDYMZIIASA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](CN)[C@H](C(F)(F)F)C1 KCNSFBLKYSGMEW-LDYMZIIASA-N 0.000 claims description 2
SUCBAXXOPKUWKE-GMSGAONNSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@@H](C(F)(F)F)[C@H](CN)CN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 SUCBAXXOPKUWKE-GMSGAONNSA-N 0.000 claims description 2
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URQPIPYFJOGMNV-NXEZZACHSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](CN)C1 URQPIPYFJOGMNV-NXEZZACHSA-N 0.000 claims description 2
BZQFKQGLRYJYFN-MWLCHTKSSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BZQFKQGLRYJYFN-MWLCHTKSSA-N 0.000 claims description 2
UMPSZZBKTQMQJD-RKDXNWHRSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UMPSZZBKTQMQJD-RKDXNWHRSA-N 0.000 claims description 2
RMERSVKMJNOJBM-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RMERSVKMJNOJBM-CFVMTHIKSA-N 0.000 claims description 2
YVNCLSOUFPUSBG-IMJJTQAJSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YVNCLSOUFPUSBG-IMJJTQAJSA-N 0.000 claims description 2
MOZUHBQCTICBJN-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MOZUHBQCTICBJN-ZNMIVQPWSA-N 0.000 claims description 2
WMMXZMSWPCDHCH-XHSDSOJGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WMMXZMSWPCDHCH-XHSDSOJGSA-N 0.000 claims description 2
JNBFVIXMWYHESF-WPGHFRTFSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JNBFVIXMWYHESF-WPGHFRTFSA-N 0.000 claims description 2
FVHCULAQBOQUHE-PJQXDXOGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FVHCULAQBOQUHE-PJQXDXOGSA-N 0.000 claims description 2
WXEULHODWRFMJL-KCXAZCMYSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WXEULHODWRFMJL-KCXAZCMYSA-N 0.000 claims description 2
YMLACVZZOGDLOE-DQYPLSBCSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YMLACVZZOGDLOE-DQYPLSBCSA-N 0.000 claims description 2
KAYKDFPFMATDAL-YUTCNCBUSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC KAYKDFPFMATDAL-YUTCNCBUSA-N 0.000 claims description 2
BXAJEQNNGNFGRI-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXAJEQNNGNFGRI-CFVMTHIKSA-N 0.000 claims description 2
FINKNCVICOYUPZ-MJBXVCDLSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FINKNCVICOYUPZ-MJBXVCDLSA-N 0.000 claims description 2
UQDOBNTYFUNMNV-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UQDOBNTYFUNMNV-ZNMIVQPWSA-N 0.000 claims description 2
HWEFAWYJNKYDOP-DGFSRKRXSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC HWEFAWYJNKYDOP-DGFSRKRXSA-N 0.000 claims description 2
CQINKMNYHQLMPR-OOVXXXAESA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CQINKMNYHQLMPR-OOVXXXAESA-N 0.000 claims description 2
JUHGKXCYUJZZLC-UGFHNGPFSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JUHGKXCYUJZZLC-UGFHNGPFSA-N 0.000 claims description 2
QTWRUBAFBNVEBZ-RLCCDNCMSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QTWRUBAFBNVEBZ-RLCCDNCMSA-N 0.000 claims description 2
NQPUKCYBHWTSMP-UHOSZYNNSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 NQPUKCYBHWTSMP-UHOSZYNNSA-N 0.000 claims description 2
CGZAJPLOVGTWQD-SXLOBPIMSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 CGZAJPLOVGTWQD-SXLOBPIMSA-N 0.000 claims description 2
AAMUVBRJTLUMSV-OTWHNJEPSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 AAMUVBRJTLUMSV-OTWHNJEPSA-N 0.000 claims description 2
TXNCRGZHDIVKJN-ZCNNSNEGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 TXNCRGZHDIVKJN-ZCNNSNEGSA-N 0.000 claims description 2
WKLBQFDYSLDYMB-WNYOCNMUSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](C)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WKLBQFDYSLDYMB-WNYOCNMUSA-N 0.000 claims description 2
VVEDUPLRSMQSNY-RFVSGWPVSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1F)C)OC1=CC=CC=C1 VVEDUPLRSMQSNY-RFVSGWPVSA-N 0.000 claims description 2
GJTHSOGLFZTWOA-XPGWFJOJSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](C)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GJTHSOGLFZTWOA-XPGWFJOJSA-N 0.000 claims description 2
GYWQGQNXCURQEH-NQERJWCQSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1)C)OC1=CC=CC=C1 GYWQGQNXCURQEH-NQERJWCQSA-N 0.000 claims description 2
NQPUKCYBHWTSMP-QXAKKESOSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 NQPUKCYBHWTSMP-QXAKKESOSA-N 0.000 claims description 2
CGZAJPLOVGTWQD-DFQSSKMNSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 CGZAJPLOVGTWQD-DFQSSKMNSA-N 0.000 claims description 2
AAMUVBRJTLUMSV-IPMKNSEASA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 AAMUVBRJTLUMSV-IPMKNSEASA-N 0.000 claims description 2
TXNCRGZHDIVKJN-XUVXKRRUSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 TXNCRGZHDIVKJN-XUVXKRRUSA-N 0.000 claims description 2
WKLBQFDYSLDYMB-HEFCMCLBSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](C)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WKLBQFDYSLDYMB-HEFCMCLBSA-N 0.000 claims description 2
GJTHSOGLFZTWOA-UIAACRFSSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](C)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GJTHSOGLFZTWOA-UIAACRFSSA-N 0.000 claims description 2
GYWQGQNXCURQEH-GQWLDOHISA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1)C)OC1=CC=CC=C1 GYWQGQNXCURQEH-GQWLDOHISA-N 0.000 claims description 2
FQEJJUYPFJSYTM-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FQEJJUYPFJSYTM-CFVMTHIKSA-N 0.000 claims description 2
WCWSUFKBVHIJCI-IMJJTQAJSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WCWSUFKBVHIJCI-IMJJTQAJSA-N 0.000 claims description 2
BIXIMKDTYJERQW-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC BIXIMKDTYJERQW-ZNMIVQPWSA-N 0.000 claims description 2
QCDOITHYWYGQQG-XHSDSOJGSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QCDOITHYWYGQQG-XHSDSOJGSA-N 0.000 claims description 2
WSNNNRWCTBIJLR-WPGHFRTFSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WSNNNRWCTBIJLR-WPGHFRTFSA-N 0.000 claims description 2
JMZBLZXEJZISCQ-PJQXDXOGSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JMZBLZXEJZISCQ-PJQXDXOGSA-N 0.000 claims description 2
WTYRDLVCSKPCMR-KCXAZCMYSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WTYRDLVCSKPCMR-KCXAZCMYSA-N 0.000 claims description 2
NIHCENZIYVQPQI-DQYPLSBCSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NIHCENZIYVQPQI-DQYPLSBCSA-N 0.000 claims description 2
OWLKBDJHUBSXIQ-RLCGTCKNSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-aminoethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@@H]([C@H](C)N)C1 OWLKBDJHUBSXIQ-RLCGTCKNSA-N 0.000 claims description 2
VHLRVQRBLBRKBC-MRCXROJRSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-aminoethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C VHLRVQRBLBRKBC-MRCXROJRSA-N 0.000 claims description 2
DPVCHDCEWZUPRH-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-5,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC(F)=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F DPVCHDCEWZUPRH-ZETCQYMHSA-N 0.000 claims description 2
OPPWHAMEKGQMSO-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-6,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F OPPWHAMEKGQMSO-ZETCQYMHSA-N 0.000 claims description 2
XSKOMKHOPDOCTI-JTQLQIEISA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F XSKOMKHOPDOCTI-JTQLQIEISA-N 0.000 claims description 2
YWSUCUHCADKMQR-LURJTMIESA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C(F)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F YWSUCUHCADKMQR-LURJTMIESA-N 0.000 claims description 2
FKEICTOGGGAVEH-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 FKEICTOGGGAVEH-ZETCQYMHSA-N 0.000 claims description 2
RFIZFCOQVQJHIT-QMMMGPOBSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 RFIZFCOQVQJHIT-QMMMGPOBSA-N 0.000 claims description 2
JPJSIIJEJSBWLK-QMMMGPOBSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-ethyl-8-fluoroquinazoline-2,4-dione Chemical compound C=1C=C2C(=O)N(N)C(=O)N(CC)C2=C(F)C=1N1CC[C@H](N)C1 JPJSIIJEJSBWLK-QMMMGPOBSA-N 0.000 claims description 2
MUHLIKWDGNBMTN-VIFPVBQESA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-8-chloro-1-(2,4-difluoroanilino)-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC=3C(=CC(F)=CC=3)F)C2=C1Cl MUHLIKWDGNBMTN-VIFPVBQESA-N 0.000 claims description 2
VBNKDDYHSBUCLM-GOEBONIOSA-N 3-amino-7-[(3s,4r)-3-amino-4-(4-hydroxyphenyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=C(O)C=C1 VBNKDDYHSBUCLM-GOEBONIOSA-N 0.000 claims description 2
ROTWRQJAWBQSOY-PSASIEDQSA-N 3-amino-7-[(3s,4r)-3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](C(F)(F)F)[C@H](N)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ROTWRQJAWBQSOY-PSASIEDQSA-N 0.000 claims description 2
RVXZTPKDGTVNSL-PRHODGIISA-N 3-amino-7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](N)C1 RVXZTPKDGTVNSL-PRHODGIISA-N 0.000 claims description 2
PQTPQNWFGHUDHR-GOEBONIOSA-N 3-amino-7-[(3s,4r)-3-amino-4-phenylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=CC=C1 PQTPQNWFGHUDHR-GOEBONIOSA-N 0.000 claims description 2
GMCPKAWGIVMLBF-ZBFHGGJFSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC GMCPKAWGIVMLBF-ZBFHGGJFSA-N 0.000 claims description 2
VBDSQUOHJPEUMO-WBVHZDCISA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C VBDSQUOHJPEUMO-WBVHZDCISA-N 0.000 claims description 2
RTOOKIGWHNEETL-CVEARBPZSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RTOOKIGWHNEETL-CVEARBPZSA-N 0.000 claims description 2
QRNGWKNPJGFQPC-SJORKVTESA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QRNGWKNPJGFQPC-SJORKVTESA-N 0.000 claims description 2
MZNFGFBDNSMXIH-HIFRSBDPSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MZNFGFBDNSMXIH-HIFRSBDPSA-N 0.000 claims description 2
BXFDZZBOVBPDGX-ZBFHGGJFSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXFDZZBOVBPDGX-ZBFHGGJFSA-N 0.000 claims description 2
SCGINPRZWGNIJN-QUCCMNQESA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 SCGINPRZWGNIJN-QUCCMNQESA-N 0.000 claims description 2
XTGWCIGUYCKYEE-CTNGQTDRSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 XTGWCIGUYCKYEE-CTNGQTDRSA-N 0.000 claims description 2
XHJWTSVTXZXVAI-UXHICEINSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(C)(C)[C@@H]([C@@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 XHJWTSVTXZXVAI-UXHICEINSA-N 0.000 claims description 2
UOUBDUJSNOAUGB-RTWAWAEBSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(C)(C)[C@@H]([C@@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 UOUBDUJSNOAUGB-RTWAWAEBSA-N 0.000 claims description 2
MZNFGFBDNSMXIH-UKRRQHHQSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MZNFGFBDNSMXIH-UKRRQHHQSA-N 0.000 claims description 2
BXFDZZBOVBPDGX-GDBMZVCRSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXFDZZBOVBPDGX-GDBMZVCRSA-N 0.000 claims description 2
SCGINPRZWGNIJN-UYAOXDASSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 SCGINPRZWGNIJN-UYAOXDASSA-N 0.000 claims description 2
XTGWCIGUYCKYEE-TZIWHRDSSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 XTGWCIGUYCKYEE-TZIWHRDSSA-N 0.000 claims description 2
XHJWTSVTXZXVAI-WOJBJXKFSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(C)(C)[C@@H]([C@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 XHJWTSVTXZXVAI-WOJBJXKFSA-N 0.000 claims description 2
UOUBDUJSNOAUGB-NHCUHLMSSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(C)(C)[C@@H]([C@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 UOUBDUJSNOAUGB-NHCUHLMSSA-N 0.000 claims description 2
TWIRCKLBUNQVOF-LLVKDONJSA-N 3-amino-7-[(7s)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C([C@H]1N)N(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 TWIRCKLBUNQVOF-LLVKDONJSA-N 0.000 claims description 2
YLJXHSMLHOQOQO-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C(C3CCCCC3C2)CN)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 YLJXHSMLHOQOQO-UHFFFAOYSA-N 0.000 claims description 2
SAXDOWIIPOHGJK-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C(C3CCCCC3C2)CN)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SAXDOWIIPOHGJK-UHFFFAOYSA-N 0.000 claims description 2
WZEFJJXSICOLBU-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 WZEFJJXSICOLBU-UHFFFAOYSA-N 0.000 claims description 2
GQDNXEYBOILUQI-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GQDNXEYBOILUQI-UHFFFAOYSA-N 0.000 claims description 2
GTMSVWIYIYVALU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=N1 GTMSVWIYIYVALU-UHFFFAOYSA-N 0.000 claims description 2
RXYNGNBFBLYGSY-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=N1 RXYNGNBFBLYGSY-UHFFFAOYSA-N 0.000 claims description 2
FEHIBOSQMNCPEA-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2N=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 FEHIBOSQMNCPEA-UHFFFAOYSA-N 0.000 claims description 2
RNKBXOPKFRJXLU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2N=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RNKBXOPKFRJXLU-UHFFFAOYSA-N 0.000 claims description 2
VLPCEPGNRLOKKI-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound S1C(CN)=NC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=C1 VLPCEPGNRLOKKI-UHFFFAOYSA-N 0.000 claims description 2
VGZXYHMCVGVCNU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound S1C(CN)=NC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2)Cl)=C1 VGZXYHMCVGVCNU-UHFFFAOYSA-N 0.000 claims description 2
MCNRVILVRXNFEW-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C MCNRVILVRXNFEW-UHFFFAOYSA-N 0.000 claims description 2
WIASPBIONPUBMS-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WIASPBIONPUBMS-UHFFFAOYSA-N 0.000 claims description 2
RJMVZYHGELRPCW-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RJMVZYHGELRPCW-UHFFFAOYSA-N 0.000 claims description 2
WVGCPHLVGBIWQO-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WVGCPHLVGBIWQO-UHFFFAOYSA-N 0.000 claims description 2
FXWFMHCPNJKXRV-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FXWFMHCPNJKXRV-UHFFFAOYSA-N 0.000 claims description 2
JYTPZOFUDSEQLZ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JYTPZOFUDSEQLZ-UHFFFAOYSA-N 0.000 claims description 2
UKCYMUVIAIBGCN-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UKCYMUVIAIBGCN-UHFFFAOYSA-N 0.000 claims description 2
KOAOBZHRZZCYOO-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C KOAOBZHRZZCYOO-UHFFFAOYSA-N 0.000 claims description 2
PBIQRYGYWPNSOC-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PBIQRYGYWPNSOC-UHFFFAOYSA-N 0.000 claims description 2
YTPFASONAAHNOG-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YTPFASONAAHNOG-UHFFFAOYSA-N 0.000 claims description 2
FKUXSJDSRQEGOR-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FKUXSJDSRQEGOR-UHFFFAOYSA-N 0.000 claims description 2
JTQIFMBURAIWOK-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JTQIFMBURAIWOK-UHFFFAOYSA-N 0.000 claims description 2
CZZQRAFHQVAXKC-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CZZQRAFHQVAXKC-UHFFFAOYSA-N 0.000 claims description 2
USOBMQHLJRHNHP-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C USOBMQHLJRHNHP-UHFFFAOYSA-N 0.000 claims description 2
RGTJHADPUQZPAB-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RGTJHADPUQZPAB-UHFFFAOYSA-N 0.000 claims description 2
NLBOGRPLEXDCAN-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C(C)OC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NLBOGRPLEXDCAN-UHFFFAOYSA-N 0.000 claims description 2
GSNGUCUBKBUSIT-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C(C)OC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C GSNGUCUBKBUSIT-UHFFFAOYSA-N 0.000 claims description 2
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OALBPTZREKXPIM-UHFFFAOYSA-N 3-amino-7-[3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C(CF)C1 OALBPTZREKXPIM-UHFFFAOYSA-N 0.000 claims description 2
KPEAZQRJPMJXJT-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C KPEAZQRJPMJXJT-UHFFFAOYSA-N 0.000 claims description 2
SMDLSNLIQFGZQR-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SMDLSNLIQFGZQR-UHFFFAOYSA-N 0.000 claims description 2
GRXRVQDLXPKRNU-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C GRXRVQDLXPKRNU-UHFFFAOYSA-N 0.000 claims description 2
TZRXNTDEOOJEOX-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C TZRXNTDEOOJEOX-UHFFFAOYSA-N 0.000 claims description 2
PKBTXJAYWZVJJY-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PKBTXJAYWZVJJY-UHFFFAOYSA-N 0.000 claims description 2
SYRCIDHXOSWLRM-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SYRCIDHXOSWLRM-UHFFFAOYSA-N 0.000 claims description 2
KIDXJJUVIKPCOD-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound FC1=NC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(CC1(C)C)CC1C(N)COC1=CC=CC=C1 KIDXJJUVIKPCOD-UHFFFAOYSA-N 0.000 claims description 2
QTXQQPOORDXHBQ-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C)(C)C(C(N)COC=3C=CC=CC=3)C2)C=NC(C(N(N)C2=O)=O)=C1N2C1CC1 QTXQQPOORDXHBQ-UHFFFAOYSA-N 0.000 claims description 2
VGWZEGVEGQPYNW-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C)(C)C(C(N)COC=3C=CC=CC=3)C2)N=CC(C(N(N)C2=O)=O)=C1N2C1CC1 VGWZEGVEGQPYNW-UHFFFAOYSA-N 0.000 claims description 2
OPXSUSIFKCWAAZ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 OPXSUSIFKCWAAZ-UHFFFAOYSA-N 0.000 claims description 2
ODGYFTKNQVXYPX-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C ODGYFTKNQVXYPX-UHFFFAOYSA-N 0.000 claims description 2
GVYDJTMGSWNLLQ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(C(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GVYDJTMGSWNLLQ-UHFFFAOYSA-N 0.000 claims description 2
YSWSMAOIADXSJJ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YSWSMAOIADXSJJ-UHFFFAOYSA-N 0.000 claims description 2
SIPVOUZPSPRUAB-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl SIPVOUZPSPRUAB-UHFFFAOYSA-N 0.000 claims description 2
LURQEEMHISKSRX-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl LURQEEMHISKSRX-UHFFFAOYSA-N 0.000 claims description 2
FXLFPNNYZRRJCG-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(C)(C)C1 FXLFPNNYZRRJCG-UHFFFAOYSA-N 0.000 claims description 2
WHVDJPHTVKCYDW-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WHVDJPHTVKCYDW-UHFFFAOYSA-N 0.000 claims description 2
RSCLUHGIBZKZFO-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(C(C)(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RSCLUHGIBZKZFO-UHFFFAOYSA-N 0.000 claims description 2
HJUIXGXPYMFZOH-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(F)(F)C(C(C)(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 HJUIXGXPYMFZOH-UHFFFAOYSA-N 0.000 claims description 2
QILKGBMFMDBJDG-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(C)(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl QILKGBMFMDBJDG-UHFFFAOYSA-N 0.000 claims description 2
YJTLAGQFKMRSHQ-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(F)(F)C1 YJTLAGQFKMRSHQ-UHFFFAOYSA-N 0.000 claims description 2
HVYIEAHRHFOQNA-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(F)(F)C1 HVYIEAHRHFOQNA-UHFFFAOYSA-N 0.000 claims description 2
VWQSCDFRKGGQGQ-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(CN)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 VWQSCDFRKGGQGQ-UHFFFAOYSA-N 0.000 claims description 2
LLQRSSCZBZXNKD-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(F)(F)C(CN)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 LLQRSSCZBZXNKD-UHFFFAOYSA-N 0.000 claims description 2
UCDQJTZOFJBISG-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(F)(F)C(CN)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UCDQJTZOFJBISG-UHFFFAOYSA-N 0.000 claims description 2
MMXUEEUSEQTGLI-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(CN)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl MMXUEEUSEQTGLI-UHFFFAOYSA-N 0.000 claims description 2
RTILSMIWBOHCLQ-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 RTILSMIWBOHCLQ-UHFFFAOYSA-N 0.000 claims description 2
ZAURZWBNIZPUJO-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 ZAURZWBNIZPUJO-UHFFFAOYSA-N 0.000 claims description 2
PIXOZOYGPDFQRN-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2C=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 PIXOZOYGPDFQRN-UHFFFAOYSA-N 0.000 claims description 2
BCBJQYLJYAALNN-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2C=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BCBJQYLJYAALNN-UHFFFAOYSA-N 0.000 claims description 2
MAXNCKAGFRGUGY-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound S1C(CN)=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=C1 MAXNCKAGFRGUGY-UHFFFAOYSA-N 0.000 claims description 2
GIKALOAWFNMZSD-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound S1C(CN)=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2)Cl)=C1 GIKALOAWFNMZSD-UHFFFAOYSA-N 0.000 claims description 2
QAPRITTXNPCYSU-UHFFFAOYSA-N 3-amino-7-[7-(1-aminoethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC(N)C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)C)CC11CC1 QAPRITTXNPCYSU-UHFFFAOYSA-N 0.000 claims description 2
AINBVJBQTTZKNW-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(CN)C21CC2 AINBVJBQTTZKNW-UHFFFAOYSA-N 0.000 claims description 2
ASPRZCFYJNJRGE-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(CN)C21CC2 ASPRZCFYJNJRGE-UHFFFAOYSA-N 0.000 claims description 2
XHDGVTPMBJEXOC-QXXIUIOUSA-N 3-amino-8-[(3R)-3-[(1S)-1-aminoethyl]pyrrolidin-1-yl]-7-fluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N3C(C)CCC1=C32 XHDGVTPMBJEXOC-QXXIUIOUSA-N 0.000 claims description 2
MFMDCVFUAGRPIL-CBMCFHRWSA-N 3-amino-8-[(3R)-3-[(1S)-1-aminoethyl]pyrrolidin-1-yl]-7-fluoro-12-methyl-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N3C(C)COC1=C32 MFMDCVFUAGRPIL-CBMCFHRWSA-N 0.000 claims description 2
LGBHTXIBLKBUKN-GKAPJAKFSA-N 3-amino-8-[(3S)-3-aminopyrrolidin-1-yl]-7-fluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound FC1=CC(C(N(N)C2=O)=O)=C3N2C(C)CCC3=C1N1CC[C@H](N)C1 LGBHTXIBLKBUKN-GKAPJAKFSA-N 0.000 claims description 2
MQYWJXVDBHTHJE-MQWKRIRWSA-N 3-amino-8-[(3S)-3-aminopyrrolidin-1-yl]-7-fluoro-12-methyl-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound FC1=CC(C(N(N)C2=O)=O)=C3N2C(C)COC3=C1N1CC[C@H](N)C1 MQYWJXVDBHTHJE-MQWKRIRWSA-N 0.000 claims description 2
DTSFGOGGBWDFOX-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)quinazoline-2,4-dione Chemical compound C1C2CN(C)CC2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 DTSFGOGGBWDFOX-UHFFFAOYSA-N 0.000 claims description 2
UYELLIFHKILPAN-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(CO)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 UYELLIFHKILPAN-UHFFFAOYSA-N 0.000 claims description 2
JFFKNWQKPVVSFQ-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C1C(CNC(C)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl JFFKNWQKPVVSFQ-UHFFFAOYSA-N 0.000 claims description 2
LEQNXEXZTCRROR-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CCNCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 LEQNXEXZTCRROR-UHFFFAOYSA-N 0.000 claims description 2
RRTPRFUHVCSHRT-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CCCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 RRTPRFUHVCSHRT-UHFFFAOYSA-N 0.000 claims description 2
PPWBBORVAVZKHU-UHFFFAOYSA-N 7-(1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,4-c]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(N3CC4CNCCC4C3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 PPWBBORVAVZKHU-UHFFFAOYSA-N 0.000 claims description 2
GTGRQHMVAQLFNN-UHFFFAOYSA-N 7-(2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(C3NC4CNCC4CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 GTGRQHMVAQLFNN-UHFFFAOYSA-N 0.000 claims description 2
QFJKMFIBXMYTMK-RNCFNFMXSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H]([C@@H](N)CNC(N)=O)C1 QFJKMFIBXMYTMK-RNCFNFMXSA-N 0.000 claims description 2
SAKXLGUKGULDTQ-YGRLFVJLSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H]([C@@H](N)CNC(N)=O)C1 SAKXLGUKGULDTQ-YGRLFVJLSA-N 0.000 claims description 2
SRWFLGFQKJBLMZ-MFKMUULPSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound COC1=C(N2C[C@@H](CC2)[C@@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SRWFLGFQKJBLMZ-MFKMUULPSA-N 0.000 claims description 2
BOAVHSIPQXSDQP-RISCZKNCSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound CC1=C(N2C[C@@H](CC2)[C@@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BOAVHSIPQXSDQP-RISCZKNCSA-N 0.000 claims description 2
SOOAHHRQDBLUHM-LQJRIPTKSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@@H]([C@@H](N)CNC(N)=O)C1 SOOAHHRQDBLUHM-LQJRIPTKSA-N 0.000 claims description 2
CYMKJADKSGUUCQ-DVJZZOLTSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound C1[C@H]([C@@H](N)CNC(N)=O)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CYMKJADKSGUUCQ-DVJZZOLTSA-N 0.000 claims description 2
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241000894006 Bacteria Species 0.000 description 4
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
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VNGUJPHYEQJGMW-UHFFFAOYSA-N ethyl 2,3-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC=C1N1CC(NC(=O)OC(C)(C)C)CC1 VNGUJPHYEQJGMW-UHFFFAOYSA-N 0.000 description 4
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OULOUDNKONNREH-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-(fluoromethyl)pyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)(CF)CNC(O)=O)C)C1CC1)=O OULOUDNKONNREH-UHFFFAOYSA-N 0.000 description 2
238000010958 [3+2] cycloaddition reaction Methods 0.000 description 2
BZJBKQNZSPKBQK-UHFFFAOYSA-N [6,8-dichloro-1-cyclopropyl-7-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(Cl)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl BZJBKQNZSPKBQK-UHFFFAOYSA-N 0.000 description 2
BGRGVVRSJXYHLB-UHFFFAOYSA-N [7-(3-carbamoylpiperidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(C(=O)N)CCCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl BGRGVVRSJXYHLB-UHFFFAOYSA-N 0.000 description 2
JHHZHVYKGCFNMM-FMLNKVPISA-N [7-[(3S,4S)-3-[1-amino-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C(C)(C)(C)OC(=O)C([C@@H]1CN(C[C@H]1C)C1=C(C=C2C(N(C(N(C2=C1Cl)C1CC1)=O)NC(O)=O)=O)F)N JHHZHVYKGCFNMM-FMLNKVPISA-N 0.000 description 2
XKDKVSOGSDWQBN-UHFFFAOYSA-N [7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1H-isoindol-2-yl]carbamic acid Chemical compound NCC12CN(CC2CCCC1)NC(O)=O XKDKVSOGSDWQBN-UHFFFAOYSA-N 0.000 description 2
LTIHUXMRGZOUKJ-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound CC(C)(C)OC(=O)NC1CN(C=2C(=C3C(C(N(NC(O)=O)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 LTIHUXMRGZOUKJ-UHFFFAOYSA-N 0.000 description 2
AVRXUQALDJVGAX-UHFFFAOYSA-N [[2-(cyclopropylamino)-3-ethoxy-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OCC)=C1NC1CC1 AVRXUQALDJVGAX-UHFFFAOYSA-N 0.000 description 2
IYZBCRMRIRUZTO-UHFFFAOYSA-N [[2-(cyclopropylamino)-3-fluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound FC1=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=CC(C(=O)NNC(O)=O)=C1NC1CC1 IYZBCRMRIRUZTO-UHFFFAOYSA-N 0.000 description 2
NFJYXCOYGPYWMJ-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(OC)=C1NC1CC1 NFJYXCOYGPYWMJ-UHFFFAOYSA-N 0.000 description 2
XOJFHITZCDSABC-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(C)=C1NC1CC1 XOJFHITZCDSABC-UHFFFAOYSA-N 0.000 description 2
FZXRBBRJITXWLY-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(C)=C1NC1CC1 FZXRBBRJITXWLY-UHFFFAOYSA-N 0.000 description 2
PEGIKIAHJGTNFW-CQSZACIVSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[(7S)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]benzoyl]amino]carbamic acid Chemical compound C([C@H]1NC(=O)OC(C)(C)C)N(C=2C(=C(NC3CC3)C(C(=O)NNC(O)=O)=CC=2F)Cl)CC11CC1 PEGIKIAHJGTNFW-CQSZACIVSA-N 0.000 description 2
RPBWMILJKYAMOO-UHFFFAOYSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(=O)NNC(O)=O)C(NC2CC2)=C1Cl RPBWMILJKYAMOO-UHFFFAOYSA-N 0.000 description 2
NEWLMSNHUACYQQ-UHFFFAOYSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[3-methyl-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)(C)CCN1C1=C(F)C=C(C(=O)NNC(O)=O)C(NC2CC2)=C1Cl NEWLMSNHUACYQQ-UHFFFAOYSA-N 0.000 description 2
FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001356 alkyl thiols Chemical class 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000003936 benzamides Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
MXSTYZFUEGSFSI-AWEZNQCLSA-N benzyl 2,3,5,6-tetrafluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1F)F)=C(F)C(F)=C1C(=O)OCC1=CC=CC=C1 MXSTYZFUEGSFSI-AWEZNQCLSA-N 0.000 description 2
YHZJBIHCJSVWKD-KRWDZBQOSA-N benzyl 2-(cyclopropylamino)-3,5,6-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1NC2CC2)F)=C(F)C(F)=C1C(=O)OCC1=CC=CC=C1 YHZJBIHCJSVWKD-KRWDZBQOSA-N 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004296 chiral HPLC Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229960003405 ciprofloxacin Drugs 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
SBHMXBYMQZRRLC-UHFFFAOYSA-N ethyl 2,3,4,5-tetrafluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(F)=C1F SBHMXBYMQZRRLC-UHFFFAOYSA-N 0.000 description 2
GJFOWPZJBADLDJ-UHFFFAOYSA-N ethyl 2,3,4,6-tetrafluorobenzoate Chemical compound CCOC(=O)C1=C(F)C=C(F)C(F)=C1F GJFOWPZJBADLDJ-UHFFFAOYSA-N 0.000 description 2
MLANUBGYWOMWLZ-UHFFFAOYSA-N ethyl 2,3,4-trifluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C(F)=C1F MLANUBGYWOMWLZ-UHFFFAOYSA-N 0.000 description 2
PLHHLRVGWNGWPX-JTQLQIEISA-N ethyl 2,3,5-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC(F)=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 PLHHLRVGWNGWPX-JTQLQIEISA-N 0.000 description 2
ZXFYRSUEOKXKOQ-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-methoxybenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(OC)=C1F ZXFYRSUEOKXKOQ-UHFFFAOYSA-N 0.000 description 2
YCDADJUAUJPWHD-UHFFFAOYSA-N ethyl 2,4,5-trifluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C=C1F YCDADJUAUJPWHD-UHFFFAOYSA-N 0.000 description 2
AQTKJIVKYZAFNJ-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 AQTKJIVKYZAFNJ-UHFFFAOYSA-N 0.000 description 2
KJFHMLDTVFQOQA-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(CNC(=O)OC(C)(C)C)CC1 KJFHMLDTVFQOQA-UHFFFAOYSA-N 0.000 description 2
LRIZYRFXKQSOFG-UHFFFAOYSA-N ethyl 2,5-difluoro-4-pyrrolidin-1-ylbenzoate Chemical compound C1=C(F)C(C(=O)OCC)=CC(F)=C1N1CCCC1 LRIZYRFXKQSOFG-UHFFFAOYSA-N 0.000 description 2
RCKVZZTXQFAAPT-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC=C1N1CCC(NC(=O)OC(C)(C)C)C1 RCKVZZTXQFAAPT-UHFFFAOYSA-N 0.000 description 2
KLDDQZNIRQUHKU-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(N2CCCC2)C=C1NC1CC1 KLDDQZNIRQUHKU-UHFFFAOYSA-N 0.000 description 2
MYSSYHAITZSBEY-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-6-methylsulfanylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(F)=C(SC)N=C1NC1CC1 MYSSYHAITZSBEY-UHFFFAOYSA-N 0.000 description 2
UPMFDOIEEUTSQC-UHFFFAOYSA-N ethyl 3-chloro-2,4,5-trifluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(Cl)=C1F UPMFDOIEEUTSQC-UHFFFAOYSA-N 0.000 description 2
FDLKLRZONDKRDD-UHFFFAOYSA-N ethyl 3-chloro-2,5-difluoro-4-[3-(triazol-1-yl)pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(N2N=NC=C2)CC1 FDLKLRZONDKRDD-UHFFFAOYSA-N 0.000 description 2
KDKBIFLYOSNINK-ZDUSSCGKSA-N ethyl 3-chloro-2-(cyclopropylamino)-5-fluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 KDKBIFLYOSNINK-ZDUSSCGKSA-N 0.000 description 2
FEBASYOFRCJJIS-UHFFFAOYSA-N ethyl 5-chloro-2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(Cl)=C1N1CCC(NC(=O)OC(C)(C)C)C1 FEBASYOFRCJJIS-UHFFFAOYSA-N 0.000 description 2
UNTKOCVJKCACCM-UHFFFAOYSA-N ethyl 5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2-(propan-2-ylamino)benzoate Chemical compound C1=C(NC(C)C)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 UNTKOCVJKCACCM-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
JJXINDNYLSMEBI-UHFFFAOYSA-N isocyanato thiohypochlorite Chemical compound ClSN=C=O JJXINDNYLSMEBI-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
UHTYEKZZCFLKOJ-UHFFFAOYSA-N methyl 5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline-8-carboxylate Chemical compound C1CC(C)NC2=C1C(F)=C(F)C=C2C(=O)OC UHTYEKZZCFLKOJ-UHFFFAOYSA-N 0.000 description 2
FLKMOQAAIRZPTP-UHFFFAOYSA-N methyl 5,6-difluoro-2-methylquinoline-8-carboxylate Chemical compound C1=C(C)N=C2C(C(=O)OC)=CC(F)=C(F)C2=C1 FLKMOQAAIRZPTP-UHFFFAOYSA-N 0.000 description 2
VHFALIIFFRARFE-UHFFFAOYSA-N methyl 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine-5-carboxylate Chemical compound O1CC(C)NC2=C1C(F)=C(F)C=C2C(=O)OC VHFALIIFFRARFE-UHFFFAOYSA-N 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
JVDVBWCTHUYCRJ-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-2,4,5-trifluoro-3-methoxybenzamide Chemical compound COC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F JVDVBWCTHUYCRJ-UHFFFAOYSA-N 0.000 description 2
BYEGWNSSZUNVFM-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-2,4,5-trifluoro-3-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F BYEGWNSSZUNVFM-UHFFFAOYSA-N 0.000 description 2
ZIMCPIQGGYZXRS-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-3,4,6-trifluoro-2-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(F)=C1C(=O)NC(=O)NC1CC1 ZIMCPIQGGYZXRS-UHFFFAOYSA-N 0.000 description 2
QWAPDZOXNZQTRF-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-3-ethyl-2,4,5-trifluorobenzamide Chemical compound CCC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F QWAPDZOXNZQTRF-UHFFFAOYSA-N 0.000 description 2
QDLKRVMKDILCHC-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=O)NC1CC1 QDLKRVMKDILCHC-UHFFFAOYSA-N 0.000 description 2
VJPYEYRKXXVWNA-UHFFFAOYSA-N n-(pyrrolidin-3-ylmethyl)propan-2-amine Chemical compound CC(C)NCC1CCNC1 VJPYEYRKXXVWNA-UHFFFAOYSA-N 0.000 description 2
HGAWACRPWVRCFI-UHFFFAOYSA-N n-pyrrolidin-3-ylidenehydroxylamine Chemical compound ON=C1CCNC1 HGAWACRPWVRCFI-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000006268 reductive amination reaction Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
LRTPRHCNWAEZBN-UWVGGRQHSA-N tert-butyl (3as,7ar)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]2CNC[C@H]21 LRTPRHCNWAEZBN-UWVGGRQHSA-N 0.000 description 2
FNMZLLREXJAYRY-UHFFFAOYSA-N tert-butyl n-(2,4-dioxo-1h-quinazolin-3-yl)carbamate Chemical compound C1=CC=C2C(=O)N(NC(=O)OC(C)(C)C)C(=O)NC2=C1 FNMZLLREXJAYRY-UHFFFAOYSA-N 0.000 description 2
UIYMGRQQGQOESZ-UHFFFAOYSA-N tert-butyl n-(3-azabicyclo[3.1.0]hexan-1-ylmethyl)carbamate Chemical compound C1NCC2(CNC(=O)OC(C)(C)C)C1C2 UIYMGRQQGQOESZ-UHFFFAOYSA-N 0.000 description 2
DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 2
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UOJAWYVCPKBOKI-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OCC)=C1N1CCC(N)C1 UOJAWYVCPKBOKI-UHFFFAOYSA-N 0.000 description 1
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PLBHUCNDERAECD-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoroquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F PLBHUCNDERAECD-UHFFFAOYSA-N 0.000 description 1
RKSAGDHXJJUAAZ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-6-chloro-1-cyclopropyl-8-fluoroquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(N)CCN1C1=C(Cl)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F RKSAGDHXJJUAAZ-UHFFFAOYSA-N 0.000 description 1
XFCMILOJGNQNJQ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-(cyclobutylamino)-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CCC3)C2=C1Cl XFCMILOJGNQNJQ-UHFFFAOYSA-N 0.000 description 1
ZLIIPNMSQNFJNJ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ZLIIPNMSQNFJNJ-UHFFFAOYSA-N 0.000 description 1
ZNLDFRNWTKWEOQ-DDWIOCJRSA-N 3-amino-7-[(3R)-3-aminopyrrolidin-1-yl]-8-chloro-6-fluoro-1-propan-2-ylquinazoline-2,4-dione 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC=1C=C2C(=O)N(N)C(=O)N(C(C)C)C2=C(Cl)C=1N1CC[C@@H](N)C1 ZNLDFRNWTKWEOQ-DDWIOCJRSA-N 0.000 description 1
AHOSTKCQPPBDLY-UTONKHPSSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F AHOSTKCQPPBDLY-UTONKHPSSA-N 0.000 description 1
LNQJOAGOEPQGMS-RFVHGSKJSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H](C(C)(C)N)C1 LNQJOAGOEPQGMS-RFVHGSKJSA-N 0.000 description 1
VOKNCJBYEYCFSK-SBSPUUFOSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 VOKNCJBYEYCFSK-SBSPUUFOSA-N 0.000 description 1
ANKPYIGFKBCEHD-HNCPQSOCSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-ethyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC=1C=C2C(=O)N(N)C(=O)N(CC)C2=CC=1N1CC[C@@H](C(C)(C)N)C1 ANKPYIGFKBCEHD-HNCPQSOCSA-N 0.000 description 1
RSRHECKHQUFWDS-SBSPUUFOSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl RSRHECKHQUFWDS-SBSPUUFOSA-N 0.000 description 1
DYOPBGVIQJYWKT-OULXEKPRSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 DYOPBGVIQJYWKT-OULXEKPRSA-N 0.000 description 1
UBCKVMOGDJVZRS-OULXEKPRSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UBCKVMOGDJVZRS-OULXEKPRSA-N 0.000 description 1
UMMNGHVJQVQNQO-JHQAJZDGSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](CN)[C@H](C(F)(F)F)C1 UMMNGHVJQVQNQO-JHQAJZDGSA-N 0.000 description 1
FRJNGFKFXGJMPL-YZUKSGEXSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](C(F)(F)F)[C@H](CN)CN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 FRJNGFKFXGJMPL-YZUKSGEXSA-N 0.000 description 1
NYLXPTOBPUBAKP-DAIXLEOSSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@H](CN)C1 NYLXPTOBPUBAKP-DAIXLEOSSA-N 0.000 description 1
GVOQJEQGINSQJQ-DHTOPLTISA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](CN)C1 GVOQJEQGINSQJQ-DHTOPLTISA-N 0.000 description 1
UKSGWMYWSATPLA-FOKYBFFNSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UKSGWMYWSATPLA-FOKYBFFNSA-N 0.000 description 1
IMFRQKZCUZONHJ-VTLYIQCISA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl IMFRQKZCUZONHJ-VTLYIQCISA-N 0.000 description 1
ZYADQXOQEXVASL-DHXVBOOMSA-N 3-amino-7-[(3s)-3-[(1r)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H]([C@H](N)C)CCN1C(C(=C1C)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 ZYADQXOQEXVASL-DHXVBOOMSA-N 0.000 description 1
WARILAOSVCTZHW-IYPAPVHQSA-N 3-amino-7-[(3s)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@H]([C@H](C)N)C1 WARILAOSVCTZHW-IYPAPVHQSA-N 0.000 description 1
CEZGKXLXBJRIIA-ACMTZBLWSA-N 3-amino-7-[(3s)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CEZGKXLXBJRIIA-ACMTZBLWSA-N 0.000 description 1
JXFUCHOBQBAYQT-PPHPATTJSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F JXFUCHOBQBAYQT-PPHPATTJSA-N 0.000 description 1
BCAHPRGZPFKUGT-FJXQXJEOSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 BCAHPRGZPFKUGT-FJXQXJEOSA-N 0.000 description 1
BPEVIOTUMZJAOB-QRPNPIFTSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 BPEVIOTUMZJAOB-QRPNPIFTSA-N 0.000 description 1
AMVCSCAODIKALF-QRPNPIFTSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-ethyl-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C=1C=C2C(=O)N(N)C(=O)N(CC)C2=C(F)C=1N1CC[C@H](N)C1 AMVCSCAODIKALF-QRPNPIFTSA-N 0.000 description 1
JUGFRRIJVWAKOP-KUARMEPBSA-N 3-amino-7-[(3s,4r)-3-amino-4-(4-hydroxyphenyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=C(O)C=C1 JUGFRRIJVWAKOP-KUARMEPBSA-N 0.000 description 1
RURUAHSSUDTPRG-GHXDPTCOSA-N 3-amino-7-[(3s,4r)-3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](C(F)(F)F)[C@H](N)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl RURUAHSSUDTPRG-GHXDPTCOSA-N 0.000 description 1
MKZORZFZIUDMEU-DAIXLEOSSA-N 3-amino-7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](N)C1 MKZORZFZIUDMEU-DAIXLEOSSA-N 0.000 description 1
IQUDLNDPTUIKCB-KUARMEPBSA-N 3-amino-7-[(3s,4r)-3-amino-4-phenylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=CC=C1 IQUDLNDPTUIKCB-KUARMEPBSA-N 0.000 description 1
VYVNZMMXSHNJES-RFVHGSKJSA-N 3-amino-7-[(7s)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C([C@H]1N)N(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 VYVNZMMXSHNJES-RFVHGSKJSA-N 0.000 description 1
AUHAELJWTZSXSM-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(F)(C(C)N)C1 AUHAELJWTZSXSM-UHFFFAOYSA-N 0.000 description 1
NHCRTLNFBXYYDH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-methoxypyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(OC)(C(C)N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NHCRTLNFBXYYDH-UHFFFAOYSA-N 0.000 description 1
RMTXVPQSJMHJQZ-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(C(C)N)C1 RMTXVPQSJMHJQZ-UHFFFAOYSA-N 0.000 description 1
SNMVABNRCFRALH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SNMVABNRCFRALH-UHFFFAOYSA-N 0.000 description 1
KSHGSPOSLMZZAJ-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(C(C)N)C1 KSHGSPOSLMZZAJ-UHFFFAOYSA-N 0.000 description 1
NCENSWFJWDJDIH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C(N)CC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NCENSWFJWDJDIH-UHFFFAOYSA-N 0.000 description 1
AXGMDASHCPHNPD-UHFFFAOYSA-N 3-amino-7-[3-(2-aminoethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CCN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl AXGMDASHCPHNPD-UHFFFAOYSA-N 0.000 description 1
XRJWZFHAORTBPI-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)(CF)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 XRJWZFHAORTBPI-UHFFFAOYSA-N 0.000 description 1
QUCCIKPDPPTAMJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(methoxymethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(COC)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QUCCIKPDPPTAMJ-UHFFFAOYSA-N 0.000 description 1
MZNCQIAYNOZRLW-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-benzylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC1(CN)CC1=CC=CC=C1 MZNCQIAYNOZRLW-UHFFFAOYSA-N 0.000 description 1
BOQGXRFIZBKXCA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(CN)C1 BOQGXRFIZBKXCA-UHFFFAOYSA-N 0.000 description 1
MJEXVZKNLWYGMW-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl MJEXVZKNLWYGMW-UHFFFAOYSA-N 0.000 description 1
ILRKEDGPSROFJA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ILRKEDGPSROFJA-UHFFFAOYSA-N 0.000 description 1
DHZKFGGXIOSWDX-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 DHZKFGGXIOSWDX-UHFFFAOYSA-N 0.000 description 1
HUXFMNVSPFSMDJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(CN)C1 HUXFMNVSPFSMDJ-UHFFFAOYSA-N 0.000 description 1
ZGWNSOGHYLBQOJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 ZGWNSOGHYLBQOJ-UHFFFAOYSA-N 0.000 description 1
HSDRQRXLMXJWQS-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl HSDRQRXLMXJWQS-UHFFFAOYSA-N 0.000 description 1
PCPFOUWNFJLCLB-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(C)(C)C1 PCPFOUWNFJLCLB-UHFFFAOYSA-N 0.000 description 1
MFUNKJCFFMYGIK-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C MFUNKJCFFMYGIK-UHFFFAOYSA-N 0.000 description 1
YSXPQFLFRPAOMJ-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(CN)C21CC2 YSXPQFLFRPAOMJ-UHFFFAOYSA-N 0.000 description 1
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229940125851 compound 27 Drugs 0.000 description 1
229940127204 compound 29 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940125878 compound 36 Drugs 0.000 description 1
229940125807 compound 37 Drugs 0.000 description 1
229940127573 compound 38 Drugs 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
229940125844 compound 46 Drugs 0.000 description 1
229940127271 compound 49 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
229940126545 compound 53 Drugs 0.000 description 1
229940125900 compound 59 Drugs 0.000 description 1
229940126179 compound 72 Drugs 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
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NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
125000006371 dihalo methyl group Chemical group 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
XTMYIEIMUNPCAN-UHFFFAOYSA-N ethyl 2,3,4-trifluoro-5-methoxybenzoate Chemical compound CCOC(=O)C1=CC(OC)=C(F)C(F)=C1F XTMYIEIMUNPCAN-UHFFFAOYSA-N 0.000 description 1
BWNOFHKEKFPTBV-JTQLQIEISA-N ethyl 2,3,6-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=C(F)C=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 BWNOFHKEKFPTBV-JTQLQIEISA-N 0.000 description 1
DWRVQRRMMIQTBY-UHFFFAOYSA-N ethyl 2,3-difluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC(OC)=C1N1CC(NC(=O)OC(C)(C)C)CC1 DWRVQRRMMIQTBY-UHFFFAOYSA-N 0.000 description 1
IDCQRHBVSOPQSN-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-(phenylmethoxyiminomethyl)benzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(C=NOCC=2C=CC=CC=2)=C1F IDCQRHBVSOPQSN-UHFFFAOYSA-N 0.000 description 1
CNLWICAPVKYJDJ-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(C)=C1F CNLWICAPVKYJDJ-UHFFFAOYSA-N 0.000 description 1
DXEDQZQUGXXWSF-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(CNC(=O)OC(C)(C)C)CC1 DXEDQZQUGXXWSF-UHFFFAOYSA-N 0.000 description 1
USTAENCAYUNVTB-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methyl-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 USTAENCAYUNVTB-UHFFFAOYSA-N 0.000 description 1
GTHZCGNEWNJQJS-UHFFFAOYSA-N ethyl 2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-3-(phenylmethoxyiminomethyl)benzoate Chemical compound C=1C=CC=CC=1CON=CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 GTHZCGNEWNJQJS-UHFFFAOYSA-N 0.000 description 1
DOKPAMDPONKHKL-KZUDCZAMSA-N ethyl 2-(butan-2-ylamino)-3-chloro-5-fluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(NC(C)CC)C(C(=O)OCC)=CC(F)=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 DOKPAMDPONKHKL-KZUDCZAMSA-N 0.000 description 1
YXDJQYZWVRALDE-UHFFFAOYSA-N ethyl 2-(cyclobutylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C=C1NC1CCC1 YXDJQYZWVRALDE-UHFFFAOYSA-N 0.000 description 1
MGPLAEBQINWPMD-ZDUSSCGKSA-N ethyl 2-(cyclopropylamino)-3,5-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 MGPLAEBQINWPMD-ZDUSSCGKSA-N 0.000 description 1
NSABSAJYHZYYMK-ZDUSSCGKSA-N ethyl 2-(cyclopropylamino)-3,6-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=C(F)C=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 NSABSAJYHZYYMK-ZDUSSCGKSA-N 0.000 description 1
RCSVXGMSCAHJGY-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-ethoxy-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 RCSVXGMSCAHJGY-UHFFFAOYSA-N 0.000 description 1
XWDXQVZBNAZYEW-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-fluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(OC)=C1N1CCC(NC(=O)OC(C)(C)C)C1 XWDXQVZBNAZYEW-UHFFFAOYSA-N 0.000 description 1
OTDZYMWFJNREHP-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 OTDZYMWFJNREHP-UHFFFAOYSA-N 0.000 description 1
RJJPONQZMPHMAC-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(CNC(=O)OC(C)(C)C)C1 RJJPONQZMPHMAC-UHFFFAOYSA-N 0.000 description 1
JUPGNVIZIUFIDH-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-3-(phenylmethoxyiminomethyl)benzoate Chemical compound C=1C=CC=CC=1CON=CC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 JUPGNVIZIUFIDH-UHFFFAOYSA-N 0.000 description 1
KOWLMUHLYWGECF-UHFFFAOYSA-N ethyl 2-chloro-5-fluoro-6-methylsulfanylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(F)=C(SC)N=C1Cl KOWLMUHLYWGECF-UHFFFAOYSA-N 0.000 description 1
CINXGNHRKLMYRK-UHFFFAOYSA-N ethyl 2-cyclopropylideneacetate Chemical compound CCOC(=O)C=C1CC1 CINXGNHRKLMYRK-UHFFFAOYSA-N 0.000 description 1
GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
XITYZNUXHDHZKA-UHFFFAOYSA-N ethyl 3-chloro-2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 XITYZNUXHDHZKA-UHFFFAOYSA-N 0.000 description 1
NXCURRNUONQADF-UHFFFAOYSA-N ethyl 3-ethoxy-2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 NXCURRNUONQADF-UHFFFAOYSA-N 0.000 description 1
FCWLRKKKNGDVQE-UHFFFAOYSA-N ethyl 5-benzyl-5-azaspiro[2.4]heptane-2-carboxylate Chemical compound CCOC(=O)C1CC11CN(CC=2C=CC=CC=2)CC1 FCWLRKKKNGDVQE-UHFFFAOYSA-N 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
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239000011491 glass wool Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
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238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
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229910052742 iron Inorganic materials 0.000 description 1
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JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
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XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 1
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YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 description 1
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WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
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150000002894 organic compounds Chemical class 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
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YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
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NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000008569 process Effects 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical group C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
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125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical group NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 description 1
XSUHSSTUTHPGDQ-UHFFFAOYSA-N pyrrolidin-3-ylmethylcarbamic acid Chemical compound OC(=O)NCC1CCNC1 XSUHSSTUTHPGDQ-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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125000006413 ring segment Chemical group 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 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
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
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150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
206010042772 syncope Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical group CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
HOLFKYFPAJFTQK-UHFFFAOYSA-N tert-butyl n-(1-piperidin-3-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1CCCNC1 HOLFKYFPAJFTQK-UHFFFAOYSA-N 0.000 description 1
OWGYHEOEGOLPEK-UHFFFAOYSA-N tert-butyl n-(2-pyrrolidin-3-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC1CCNC1 OWGYHEOEGOLPEK-UHFFFAOYSA-N 0.000 description 1
QIYOMZXJQAKHEK-UHFFFAOYSA-N tert-butyl n-(3-azabicyclo[3.1.0]hexan-6-yl)carbamate Chemical compound C1NCC2C(NC(=O)OC(C)(C)C)C21 QIYOMZXJQAKHEK-UHFFFAOYSA-N 0.000 description 1
DIQWSFWWYVRXRO-UHFFFAOYSA-N tert-butyl n-(3-methylpyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1(C)CCNC1 DIQWSFWWYVRXRO-UHFFFAOYSA-N 0.000 description 1
HOVWKJWUCRVIBO-UHFFFAOYSA-N tert-butyl n-(5-azaspiro[2.4]heptan-7-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CNCC11CC1 HOVWKJWUCRVIBO-UHFFFAOYSA-N 0.000 description 1
VRLMNTJDNRPIFB-UHFFFAOYSA-N tert-butyl n-[(3-benzylpyrrolidin-3-yl)methyl]carbamate Chemical compound C=1C=CC=CC=1CC1(CNC(=O)OC(C)(C)C)CCNC1 VRLMNTJDNRPIFB-UHFFFAOYSA-N 0.000 description 1
AXCFIJFQUMHJRG-UHFFFAOYSA-N tert-butyl n-[(3-methylpyrrolidin-3-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1(C)CCNC1 AXCFIJFQUMHJRG-UHFFFAOYSA-N 0.000 description 1
OTEUFMMUHJTHRF-NSHDSACASA-N tert-butyl n-[(3s)-1-(3-amino-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 OTEUFMMUHJTHRF-NSHDSACASA-N 0.000 description 1
JNSQOXAPISKZGT-AWEZNQCLSA-N tert-butyl n-[(3s)-1-[2-chloro-3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound ClC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 JNSQOXAPISKZGT-AWEZNQCLSA-N 0.000 description 1
FQYOOTTXAJMDLQ-INIZCTEOSA-N tert-butyl n-[(3s)-1-[5-(2,4-difluoroanilino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2C[C@H](CC2)NC(=O)OC(C)(C)C)C=C1NC1=CC=C(F)C=C1F FQYOOTTXAJMDLQ-INIZCTEOSA-N 0.000 description 1
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JJJDLYOZIBFYDH-UHFFFAOYSA-N tert-butyl n-[1-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)ethyl]carbamate Chemical compound C1C2(CC2)C(C(NC(=O)OC(C)(C)C)C)CN1CC1=CC=CC=C1 JJJDLYOZIBFYDH-UHFFFAOYSA-N 0.000 description 1
QLXICPNSUOQISE-UHFFFAOYSA-N tert-butyl n-[1-[2-chloro-3-(cyclobutylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound ClC1=C(NC2CCC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 QLXICPNSUOQISE-UHFFFAOYSA-N 0.000 description 1
JZUFJGCCTLZSFE-UHFFFAOYSA-N tert-butyl n-[1-[3-(butan-2-ylamino)-2-chloro-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound C1=C(C(=O)NNC(=O)OC(C)(C)C)C(NC(C)CC)=C(Cl)C(N2CC(CC2)NC(=O)OC(C)(C)C)=C1F JZUFJGCCTLZSFE-UHFFFAOYSA-N 0.000 description 1
DBZPVFMDQGPXNE-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-2-ethoxy-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OCC)=C1NC1CC1 DBZPVFMDQGPXNE-UHFFFAOYSA-N 0.000 description 1
LBCZMSJBRAAFAB-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-2-fluoro-6-methoxy-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound FC1=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=CC(C(=O)NNC(=O)OC(C)(C)C)=C1NC1CC1 LBCZMSJBRAAFAB-UHFFFAOYSA-N 0.000 description 1
DPVSJMYBIRCSCJ-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-6-fluoro-2-methyl-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(C)=C1NC1CC1 DPVSJMYBIRCSCJ-UHFFFAOYSA-N 0.000 description 1
WZDRADUYGSTDHX-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]-2-(phenylmethoxyiminomethyl)phenyl]pyrrolidin-3-yl]carbamate Chemical compound C=1C=CC=CC=1CON=CC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 WZDRADUYGSTDHX-UHFFFAOYSA-N 0.000 description 1
AFMAMAZBTWCOOI-UHFFFAOYSA-N tert-butyl n-[1-[5-(cyclobutylamino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C=C1NC1CCC1 AFMAMAZBTWCOOI-UHFFFAOYSA-N 0.000 description 1
MNIHYAVDKLMINM-SECBINFHSA-N tert-butyl n-[2-[(3r)-pyrrolidin-3-yl]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)[C@@H]1CCNC1 MNIHYAVDKLMINM-SECBINFHSA-N 0.000 description 1
MNIHYAVDKLMINM-VIFPVBQESA-N tert-butyl n-[2-[(3s)-pyrrolidin-3-yl]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)[C@H]1CCNC1 MNIHYAVDKLMINM-VIFPVBQESA-N 0.000 description 1
GWYXCNXINAWWBV-JGVFFNPUSA-N tert-butyl n-[[(3s,4s)-4-(trifluoromethyl)pyrrolidin-3-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@@H]1CNC[C@H]1C(F)(F)F GWYXCNXINAWWBV-JGVFFNPUSA-N 0.000 description 1
XAQBCOMOVGTDFS-UHFFFAOYSA-N tert-butyl n-[[1-[2-chloro-3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(=O)NNC(=O)OC(C)(C)C)C(NC2CC2)=C1Cl XAQBCOMOVGTDFS-UHFFFAOYSA-N 0.000 description 1
DZSMPAMHLLIGCE-HXUWFJFHSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-[(7s)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3(CC3)[C@H](NC(=O)OC(C)(C)C)C2)C=C1NC1CC1 DZSMPAMHLLIGCE-HXUWFJFHSA-N 0.000 description 1
JMWMSTLGHHXNSR-UHFFFAOYSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexan-3-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3C(C3NC(=O)OC(C)(C)C)C2)C=C1NC1CC1 JMWMSTLGHHXNSR-UHFFFAOYSA-N 0.000 description 1
YWYPFEUVPABOBS-UHFFFAOYSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CCCC2)C=C1NC1CC1 YWYPFEUVPABOBS-UHFFFAOYSA-N 0.000 description 1
RXNOKKHYLMUBQK-UHFFFAOYSA-N tert-butyl n-[[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexan-3-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3C(C3NC(=O)OC(C)(C)C)C2)C(Cl)=C1NC1CC1 RXNOKKHYLMUBQK-UHFFFAOYSA-N 0.000 description 1
LTEWWHZIIXPUBF-UHFFFAOYSA-N tert-butyl n-amino-n-[2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(F)C=C1F LTEWWHZIIXPUBF-UHFFFAOYSA-N 0.000 description 1
BSJLOBHRTVICMV-UHFFFAOYSA-N tert-butyl n-amino-n-[5-chloro-2-(cyclopropylamino)-4-fluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(Cl)=C(F)C=C1NC1CC1 BSJLOBHRTVICMV-UHFFFAOYSA-N 0.000 description 1
RARMMJLRNFXCRR-UHFFFAOYSA-N tert-butyl n-ethyl-n-(4-fluoropyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)N(CC)C1CNCC1F RARMMJLRNFXCRR-UHFFFAOYSA-N 0.000 description 1
XYKYUXYNQDXZTD-QMMMGPOBSA-N tert-butyl n-methyl-n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@H]1CCNC1 XYKYUXYNQDXZTD-QMMMGPOBSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000005309 thioalkoxy group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- C—CHEMISTRY; METALLURGY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D487/10—Spiro-condensed systems

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HR20020696A 2000-01-24 2002-08-23 3-aminoquinazolin-2,4-dione antibakterial agents HRP20020696A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US17825200P	2000-01-24	2000-01-24
US24126700P	2000-10-18	2000-10-18

Publications (1)

Publication Number	Publication Date
HRP20020696A2 true HRP20020696A2 (en)	2003-12-31

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ID=26874138

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Application Number	Title	Priority Date	Filing Date
HR20020696A HRP20020696A2 (en)	2000-01-24	2002-08-23	3-aminoquinazolin-2,4-dione antibakterial agents

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US (2)	US7094780B1 (de)
EP (1)	EP1255739B1 (de)
JP (1)	JP4811978B2 (de)
KR (1)	KR20020067701A (de)
CN (1)	CN1425008A (de)
AP (1)	AP2002002603A0 (de)
AR (1)	AR030186A1 (de)
AT (1)	ATE398110T1 (de)
AU (1)	AU783078B2 (de)
BG (1)	BG107023A (de)
BR (1)	BR0017010A (de)
CA (1)	CA2393802C (de)
CO (1)	CO5320600A1 (de)
CR (1)	CR6709A (de)
DE (1)	DE60039194D1 (de)
EA (1)	EA005585B1 (de)
EE (1)	EE200200412A (de)
ES (1)	ES2304992T3 (de)
GE (1)	GEP20053429B (de)
HK (1)	HK1054237A1 (de)
HN (1)	HN2001000009A (de)
HR (1)	HRP20020696A2 (de)
HU (1)	HUP0204101A3 (de)
IL (1)	IL150393A0 (de)
IS (1)	IS6448A (de)
MA (1)	MA26866A1 (de)
MX (1)	MXPA02005989A (de)
NO (1)	NO20023516L (de)
OA (1)	OA12316A (de)
PA (1)	PA8510101A1 (de)
PE (1)	PE20011060A1 (de)
PL (1)	PL356837A1 (de)
SK (1)	SK10572002A3 (de)
SV (1)	SV2001000288A (de)
TN (1)	TNSN01011A1 (de)
UY (1)	UY26551A1 (de)
WO (1)	WO2001053273A1 (de)
YU (1)	YU55902A (de)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1015445T3 (da)	1997-09-15	2009-05-11	Procter & Gamble	Antimikrobielle quinoloner, deres sammensætninger og anvendelser
BR0210099A (pt)	2001-05-30	2004-04-13	Warner Lambert Co	Agentes antibacterianos
JP2005501021A (ja) *	2001-06-19	2005-01-13	ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー	抗細菌剤
US6900224B2 (en) *	2002-07-31	2005-05-31	The Procter & Gamble Company	Antimicrobial quinolones, their compositions and uses
WO2005026153A1 (en) *	2003-09-12	2005-03-24	Warner-Lambert Company Llc	Quinazoline-2, 4-diones as antibacterial agents
BRPI0414319A (pt) *	2003-09-12	2006-11-07	Warner Lambert Co	agentes antibacterianos de quinolona
EP1687296A1 (de) *	2003-11-18	2006-08-09	Warner-Lambert Company LLC	Antibakterielle aminochinazolidindionderivate
WO2006019965A2 (en) *	2004-07-16	2006-02-23	Takeda San Diego, Inc.	Dipeptidyl peptidase inhibitors
GB0416730D0 (en)	2004-07-27	2004-09-01	Novartis Ag	Organic compounds
AU2006208547B2 (en) *	2005-01-26	2011-02-10	F. Hoffmann-La Roche Ag	Phenyl methanone derivatives and their use as glycine transporter 1 inhibitors
GB0507298D0 (en) *	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
US7977346B2 (en)	2006-01-17	2011-07-12	Guoqing Paul Chen	Spiro compounds and methods of use
AU2007230630B2 (en)	2006-03-28	2012-12-20	Taigen Biotechnology Co., Ltd	Malate salts, and polymorphs of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
BRPI0709220A2 (pt)	2006-03-28	2011-07-12	Procter & Gamble	processo de acoplamento para preparo de intermediários de quinolona
US20080139574A1 (en)	2006-11-30	2008-06-12	Cadila Healthcare Limited	Novel quinoline derivatives
CA2712819C (en) *	2008-01-30	2013-07-23	Shin Poong Pharmaceutical Co., Ltd.	Novel quinazoline-2,4-dione derivative, and medical compositions for the prophylaxis and treatment of cranial nerve disease containing the same
WO2011031745A1 (en)	2009-09-09	2011-03-17	Achaogen, Inc.	Antibacterial fluoroquinolone analogs
WO2012088266A2 (en)	2010-12-22	2012-06-28	Incyte Corporation	Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3
RU2626979C2 (ru)	2011-03-15	2017-08-02	Мерк Шарп Энд Дохме Корп.	Трициклические ингибиторы гиразы
RU2618673C2 (ru) *	2011-12-21	2017-05-10	Цзянсу Хэнжуй Медсин Ко., Лтд.	Производные пирролопиримидина, полезные в качестве ингибиторов jak-киназы
DK2861595T5 (en)	2012-06-13	2018-01-15	Incyte Holdings Corp	Substituted tricyclic compounds as FGFR inhibitors
US9388185B2 (en)	2012-08-10	2016-07-12	Incyte Holdings Corporation	Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors
CN105189505B (zh)	2012-09-12	2019-03-22	默克夏普&多梅有限公司	用作抗菌剂的三环促旋酶抑制剂
US9266892B2 (en)	2012-12-19	2016-02-23	Incyte Holdings Corporation	Fused pyrazoles as FGFR inhibitors
ME03015B (de)	2013-04-19	2018-10-20	Incyte Holdings Corp	Bicyclische heterocyclen als fgfr-inhibitoren
US10851105B2 (en)	2014-10-22	2020-12-01	Incyte Corporation	Bicyclic heterocycles as FGFR4 inhibitors
MA41551A (fr)	2015-02-20	2017-12-26	Incyte Corp	Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
CA2976790C (en)	2015-02-20	2024-02-27	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
WO2016134294A1 (en)	2015-02-20	2016-08-25	Incyte Corporation	Bicyclic heterocycles as fgfr4 inhibitors
CN108530448A (zh) *	2017-03-02	2018-09-14	浙江司太立制药股份有限公司	含有碱性氮杂螺环片段的苯并噻嗪-4-酮类化合物及其制备方法
AR111960A1 (es)	2017-05-26	2019-09-04	Incyte Corp	Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
SG11202010882XA (en)	2018-05-04	2020-11-27	Incyte Corp	Salts of an fgfr inhibitor
CR20200590A (es)	2018-05-04	2021-04-26	Incyte Corp	Formas sólidas de un inhibidor de fgfr y procesos para prepararlas
CN111620866A (zh) *	2019-02-27	2020-09-04	南京药石科技股份有限公司	一种顺式-7,7-二氟-六氢-1H 吡咯并[3,4-c]吡啶衍生物及其制备方法
US11628162B2 (en)	2019-03-08	2023-04-18	Incyte Corporation	Methods of treating cancer with an FGFR inhibitor
WO2021007269A1 (en)	2019-07-09	2021-01-14	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
US12122767B2 (en)	2019-10-01	2024-10-22	Incyte Corporation	Bicyclic heterocycles as FGFR inhibitors
CN115835908A (zh)	2019-10-14	2023-03-21	因赛特公司	作为fgfr抑制剂的双环杂环
WO2021076728A1 (en)	2019-10-16	2021-04-22	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
US11897891B2 (en)	2019-12-04	2024-02-13	Incyte Corporation	Tricyclic heterocycles as FGFR inhibitors
WO2021113462A1 (en)	2019-12-04	2021-06-10	Incyte Corporation	Derivatives of an fgfr inhibitor
US12012409B2 (en)	2020-01-15	2024-06-18	Incyte Corporation	Bicyclic heterocycles as FGFR inhibitors
CN111499513B (zh) *	2020-04-24	2023-03-14	上海毕得医药科技股份有限公司	一种2,3,4,5-四溴苯甲酸酯的合成方法
TW202304459A (zh)	2021-04-12	2023-02-01	美商英塞特公司	包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法
EP4352059A1 (de)	2021-06-09	2024-04-17	Incyte Corporation	Tricyclische heterocyclen als fgfr-inhibitoren

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1068263B (de) *		1959-11-05
FR1203542A (fr) *	1958-02-25	1960-01-19	Rhone Poulenc Sa	Nouveaux dérivés de la phénothiazine comportant en position 10 une chaîne pipérazinique et leurs procédés de préparation
ATE8626T1 (de)	1980-03-10	1984-08-15	Berri-Balzac Societe Dite:	3-amino-(1h,3h)-2,4-chinazolindionderivate.
GB2097784A (en) *	1981-04-28	1982-11-10	Davidson Dr John Stirton	Dihydrobenzotriazepine diones; aminoquinazoline diones
AU5813394A (en)	1992-12-23	1994-07-19	Byk Gulden Lomberg Chemische Fabrik Gmbh	Anellated uracil derivates
AU6908398A (en)	1996-10-28	1998-05-22	Versicor Inc	Fused 2,4-pyrimidinedione combinatorial libraries and biologically active fused 2,4-pyramidinediones
DK1028950T3 (da) *	1997-10-28	2003-09-01	Warner Lambert Co	7-substituerede quinazolin-2,4-dioner nyttige som antibakterielle midler
AU763839B2 (en)	1998-05-26	2003-07-31	Warner-Lambert Company	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
CA2353924A1 (en) *	1998-12-11	2000-06-22	F. Hoffmann-La Roche Ag	Cyclic hydrazine derivatives as tnf-alpha inhibitors

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CA2393802C (en)	2011-04-19
CN1425008A (zh)	2003-06-18
IL150393A0 (en)	2002-12-01
MXPA02005989A (es)	2002-10-23
NO20023516D0 (no)	2002-07-23
PE20011060A1 (es)	2001-10-12
BR0017010A (pt)	2002-11-05
SV2001000288A (es)	2001-11-30
PL356837A1 (en)	2004-07-12
EP1255739A1 (de)	2002-11-13
EA200200661A1 (ru)	2003-02-27
PA8510101A1 (es)	2003-06-30
KR20020067701A (ko)	2002-08-23
EE200200412A (et)	2003-10-15
DE60039194D1 (de)	2008-07-24
HUP0204101A2 (hu)	2003-04-28
JP4811978B2 (ja)	2011-11-09
UY26551A1 (es)	2001-04-30
CR6709A (es)	2003-11-25
HN2001000009A (es)	2001-06-13
MA26866A1 (fr)	2004-12-20
HUP0204101A3 (en)	2004-05-28
AP2002002603A0 (en)	2002-09-30
YU55902A (sh)	2006-01-16
OA12316A (en)	2006-05-15
TNSN01011A1 (en)	2005-11-10
AR030186A1 (es)	2003-08-13
CA2393802A1 (en)	2001-07-26
WO2001053273A1 (en)	2001-07-26
US20060287308A1 (en)	2006-12-21
US20060183762A1 (en)	2006-08-17
AU2089901A (en)	2001-07-31
NO20023516L (no)	2002-07-23
HK1054237A1 (zh)	2003-11-21
GEP20053429B (en)	2005-01-25
CO5320600A1 (es)	2003-09-30
SK10572002A3 (sk)	2003-10-07
BG107023A (en)	2003-04-30
EA005585B1 (ru)	2005-04-28
AU783078B2 (en)	2005-09-22
EP1255739B1 (de)	2008-06-11
IS6448A (is)	2002-06-27
US7582627B2 (en)	2009-09-01
US7094780B1 (en)	2006-08-22
ATE398110T1 (de)	2008-07-15
ES2304992T3 (es)	2008-11-01
JP2003520277A (ja)	2003-07-02

Publication	Publication Date	Title
EP1255739B1 (de)	2008-06-11	3-aminochinazolin-2,4-dione als antibakterielle mittel
DE69814135T2 (de)	2004-04-01	7-substituierte chinazolin-2,4-dionen verwendbar als antibakterielle mittel
EP0172651B1 (de)	1990-02-07	Substituierte 9-Fluor-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazin-6-carbonsäure; substituierte 5-Amino-6-fluor-1,4-dihydro-4-oxo-chinolin-3-carbonsäure; substituierte 5-Amino-6-fluor-1,4-dihydro-4-oxo-1,8-naphthyridin-3-carbonsäure; ihre Derivate; diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
HU196986B (en)	1989-02-28	Process for producing new naphtiridine- and quinoline-carboxylic acids of antibacterial activity and pharmaceutical compositions containing them
EP3080131A1 (de)	2016-10-19	Imidazopyridinverbindungen als modulatoren von il-12, il-23 und/oder ifn-alpha reaktionen
EP3541817B1 (de)	2020-12-23	Imidazopyridinverbindungen als modulatoren von il-12-, il-23- und/oder ifn-alpha-reaktionen
JPH0819099B2 (ja)	1996-02-28	アザビシクロキノロンカルボン酸化合物製造用中間体
JPH06508366A (ja)	1994-09-22	イミダゾ〔１，５−ａ〕キノキサリン
US20180222904A1 (en)	2018-08-09	Bruton's tyrosine kinase inhibitors
JP2002533465A (ja)	2002-10-08	Ｘａ因子阻害剤としての窒素を含む複素二環類
JPH0755945B2 (ja)	1995-06-14	抗菌剤
US4771055A (en)	1988-09-13	7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-quinoline-carboxylic acids
EP0362759A1 (de)	1990-04-11	Pyridinoncarbonsäuren
US20030114666A1 (en)	2003-06-19	Antibacterial agents
EP0347851B1 (de)	1993-11-10	Chinolinoncarbonsäuren
JPH037260A (ja)	1991-01-14	新規キノロン誘導体またはその塩及びこれを含有する抗菌剤
CN112079836A (zh)	2020-12-15	三唑并嘧啶类化合物及其盐、组合物和应用

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