BG104633A - ЗАМЕСТЕНИ ОКСОАЗАХЕТЕРОЦИКЛЕНИ ИНХИБИТОРИ НА ФАКТОР Ха - Google Patents

ЗАМЕСТЕНИ ОКСОАЗАХЕТЕРОЦИКЛЕНИ ИНХИБИТОРИ НА ФАКТОР Ха Download PDF

Info

Publication number: BG104633A
Authority: BG; Bulgaria
Prior art keywords: ylmethyl; piperazin; chloro; amino; quinazolin
Prior art date: 1998-01-27

Application number

BG104633A

Other languages

Bulgarian (bg)

English (en)

Inventor

William Ewing

Michael Becker

Yong CHOI-SLEDESKI

Heinz Pauls

Wei He

Stephen Condon

Roderick DAVIS

Barbara Hanney

Alfred Spada

Christopher Burns

John JIANG

Aiwen Li

Michael Myers

Wan LAU

Gregory Poli

Original Assignee

Aventis Pharmaceuticals Products Inc.

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.)

1998-01-27

Filing date

2000-07-25

Publication date

2001-03-30

2000-07-25 Application filed by Aventis Pharmaceuticals Products Inc. filed Critical Aventis Pharmaceuticals Products Inc.

2001-03-30 Publication of BG104633A publication Critical patent/BG104633A/bg

Links

229940123583 Factor Xa inhibitor Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 279
238000000034 method Methods 0.000 claims abstract description 30
230000002401 inhibitory effect Effects 0.000 claims abstract description 9
108010074860 Factor Xa Proteins 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
-1 4-chloro-thieno [3,2-c] pyridine-2-sulfonyl Chemical group 0.000 claims description 1879
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 218
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 92
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 83
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 80
239000000203 mixture Substances 0.000 claims description 77
229910052739 hydrogen Inorganic materials 0.000 claims description 73
125000001072 heteroaryl group Chemical group 0.000 claims description 69
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 68
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
125000000217 alkyl group Chemical group 0.000 claims description 54
239000002253 acid Substances 0.000 claims description 52
229910052757 nitrogen Inorganic materials 0.000 claims description 52
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 52
150000003839 salts Chemical class 0.000 claims description 50
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 44
229910052717 sulfur Inorganic materials 0.000 claims description 44
229910052760 oxygen Inorganic materials 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 38
125000000547 substituted alkyl group Chemical group 0.000 claims description 37
125000003545 alkoxy group Chemical group 0.000 claims description 34
150000002431 hydrogen Chemical class 0.000 claims description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
125000003710 aryl alkyl group Chemical group 0.000 claims description 32
125000004475 heteroaralkyl group Chemical group 0.000 claims description 27
239000012453 solvate Substances 0.000 claims description 27
125000003107 substituted aryl group Chemical group 0.000 claims description 27
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
230000015572 biosynthetic process Effects 0.000 claims description 23
150000001204 N-oxides Chemical class 0.000 claims description 22
125000002947 alkylene group Chemical group 0.000 claims description 22
125000004450 alkenylene group Chemical group 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 16
229940002612 prodrug Drugs 0.000 claims description 15
239000000651 prodrug Substances 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
108010014173 Factor X Proteins 0.000 claims description 13
125000004419 alkynylene group Chemical group 0.000 claims description 13
125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 13
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
208000007536 Thrombosis Diseases 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
APAMKXUATGRDBB-UHFFFAOYSA-N 6-chloro-1-benzothiophene Chemical compound ClC1=CC=C2C=CSC2=C1 APAMKXUATGRDBB-UHFFFAOYSA-N 0.000 claims description 9
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 9
230000000903 blocking effect Effects 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
239000003112 inhibitor Substances 0.000 claims description 7
238000001356 surgical procedure Methods 0.000 claims description 7
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 7
230000002792 vascular Effects 0.000 claims description 7
206010000891 acute myocardial infarction Diseases 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
FZZZBNKUTAVJOH-UHFFFAOYSA-N 1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound O=C1CNCCN1CC1=CC2=CN=CC=C2N1 FZZZBNKUTAVJOH-UHFFFAOYSA-N 0.000 claims description 5
SXJRFJQQWDUBFI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(O)=O)=CC2=C1 SXJRFJQQWDUBFI-UHFFFAOYSA-N 0.000 claims description 5
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
PDZBZJIOBNYCCF-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)COC1=CC=C(Cl)S1 PDZBZJIOBNYCCF-KRWDZBQOSA-N 0.000 claims description 4
TVJGEUWLKHSCRW-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 TVJGEUWLKHSCRW-SFHVURJKSA-N 0.000 claims description 4
BSPUWRUTIOUGMZ-BYPYZUCNSA-N (3s)-3-methylpiperazin-2-one Chemical compound C[C@@H]1NCCNC1=O BSPUWRUTIOUGMZ-BYPYZUCNSA-N 0.000 claims description 4
LBSSLHSDLKSISQ-INIZCTEOSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-3-methyl-1-[[4-(methylamino)quinolin-7-yl]methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(C([C@@H]3C)=O)CC=3C=C4N=CC=C(C4=CC=3)NC)=CC2=C1 LBSSLHSDLKSISQ-INIZCTEOSA-N 0.000 claims description 4
XLAFJOJHGYYPNC-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 XLAFJOJHGYYPNC-UHFFFAOYSA-N 0.000 claims description 4
UBDHHNYVNUTFEY-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 UBDHHNYVNUTFEY-UHFFFAOYSA-N 0.000 claims description 4
FSRMNBLCZIURKT-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 FSRMNBLCZIURKT-UHFFFAOYSA-N 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
IKMGUSTUEXADKO-UHFFFAOYSA-N 4-[(6-bromo-1-benzothiophen-2-yl)sulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Br)=CC2=C1 IKMGUSTUEXADKO-UHFFFAOYSA-N 0.000 claims description 4
TVKPIDAZMYJGTO-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-methylpyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound N1=CC=C2N(C)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 TVKPIDAZMYJGTO-UHFFFAOYSA-N 0.000 claims description 4
PCHBMNCFKJKQPA-UHFFFAOYSA-N 5-chlorothiophen-2-amine Chemical compound NC1=CC=C(Cl)S1 PCHBMNCFKJKQPA-UHFFFAOYSA-N 0.000 claims description 4
206010002388 Angina unstable Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
208000007814 Unstable Angina Diseases 0.000 claims description 4
210000001367 artery Anatomy 0.000 claims description 4
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
210000004204 blood vessel Anatomy 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
201000004332 intermediate coronary syndrome Diseases 0.000 claims description 4
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
IQMUCKYJXRBUEM-HNNXBMFYSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-chlorothiophen-2-yl)-2-(methoxymethyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)NC1=CC=C(Cl)S1 IQMUCKYJXRBUEM-HNNXBMFYSA-N 0.000 claims description 3
OCMQMXOWCUTTLQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4C=C5C=CC(Cl)=CC5=CC=4)[C@H](C3=O)C)=CC=C21 OCMQMXOWCUTTLQ-INIZCTEOSA-N 0.000 claims description 3
YNNCDVMRFAUEHB-HNNXBMFYSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)C)=CC=C21 YNNCDVMRFAUEHB-HNNXBMFYSA-N 0.000 claims description 3
IUUKZAPRHHDBRY-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC1=CC=C(Cl)S1 IUUKZAPRHHDBRY-INIZCTEOSA-N 0.000 claims description 3
LYIBOOBVUFKTLK-NRFANRHFSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC(Br)=CS1 LYIBOOBVUFKTLK-NRFANRHFSA-N 0.000 claims description 3
XUKLJATTXIDZOK-FQEVSTJZSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 XUKLJATTXIDZOK-FQEVSTJZSA-N 0.000 claims description 3
RHJMEECUWIXNDR-IBGZPJMESA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(N)N=C1 RHJMEECUWIXNDR-IBGZPJMESA-N 0.000 claims description 3
YEIRMODVXOUDEP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazine-2-carboxylic acid Chemical compound ClC1=CC=C2NC(CN3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(O)=O)=CC2=C1 YEIRMODVXOUDEP-UHFFFAOYSA-N 0.000 claims description 3
MRMLNJBZDDXHBY-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-n-(2-hydroxyethyl)-6-oxopiperazine-2-carboxamide Chemical compound ClC1=CC=C2NC(CN3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(=O)NCCO)=CC2=C1 MRMLNJBZDDXHBY-UHFFFAOYSA-N 0.000 claims description 3
ANFOMGVCGLRXAC-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=CC=C2NC(C(=O)O)=CC2=C1 ANFOMGVCGLRXAC-UHFFFAOYSA-N 0.000 claims description 3
FPISLDUFKABQLS-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-(2-imidazol-1-ylethyl)acetamide Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(=O)NCCN1C=CN=C1 FPISLDUFKABQLS-UHFFFAOYSA-N 0.000 claims description 3
WKMYFMYQGXBZCX-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-(2-pyridin-4-ylethyl)acetamide Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(=O)NCCC1=CC=NC=C1 WKMYFMYQGXBZCX-UHFFFAOYSA-N 0.000 claims description 3
VAAIOIFSTKQGBX-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-(3-imidazol-1-ylpropyl)acetamide Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(=O)NCCCN1C=CN=C1 VAAIOIFSTKQGBX-UHFFFAOYSA-N 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
VFYPUDNGFNHFJW-UHFFFAOYSA-N 4-[[4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(CC=2NC3=CC(Cl)=CC=C3N=2)CC1 VFYPUDNGFNHFJW-UHFFFAOYSA-N 0.000 claims description 3
208000010378 Pulmonary Embolism Diseases 0.000 claims description 3
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230000003187 abdominal effect Effects 0.000 claims description 3
230000002159 abnormal effect Effects 0.000 claims description 3
230000001154 acute effect Effects 0.000 claims description 3
239000003146 anticoagulant agent Substances 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
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UBCPLXUXFBZCHR-NRFANRHFSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-butyl-n-(4-chlorophenyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)NC1=CC=C(Cl)C=C1 UBCPLXUXFBZCHR-NRFANRHFSA-N 0.000 claims description 2
CPWSNMQMFPMTGF-INIZCTEOSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorothiophen-2-yl)-2-(3-oxopropyl)piperazine-1-carboxamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C[C@@H]1CCC=O)CCN1C(=O)NC1=CC(Cl)=CS1 CPWSNMQMFPMTGF-INIZCTEOSA-N 0.000 claims description 2
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XLSBKTYOXPAHKE-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]-3-ethylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4C=C5C=CC(Cl)=CC5=CC=4)[C@H](C3=O)CC)=CC=C21 XLSBKTYOXPAHKE-DEOSSOPVSA-N 0.000 claims description 2
FGHDWIUNRFSFFB-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chloroanilino)acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CNC1=CC=C(Cl)C=C1 FGHDWIUNRFSFFB-FQEVSTJZSA-N 0.000 claims description 2
GAYCSJLTVUUHFI-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorophenoxy)acetyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC1=CC=C(Cl)C=C1 GAYCSJLTVUUHFI-FQEVSTJZSA-N 0.000 claims description 2
WDEJJPNCFNYSGS-RUINGEJQSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC=C(Cl)S1 WDEJJPNCFNYSGS-RUINGEJQSA-N 0.000 claims description 2
ZWIVYFALKIOQLP-LBPRGKRZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)COC1=CC=C(Cl)S1 ZWIVYFALKIOQLP-LBPRGKRZSA-N 0.000 claims description 2
XJLLMXJBKSKJEV-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromophenyl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(Br)C=C1 XJLLMXJBKSKJEV-NRFANRHFSA-N 0.000 claims description 2
JGPUUXNCEMSQHF-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-bromothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC=C(Br)S1 JGPUUXNCEMSQHF-ZDUSSCGKSA-N 0.000 claims description 2
UZGGHAZVCFWUCI-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)but-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=C(C)C1=CC=C(Cl)S1 UZGGHAZVCFWUCI-SFHVURJKSA-N 0.000 claims description 2
MLBCOMHEHVFVSU-PKDNWHCCSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)C=CC1=CC=C(Cl)S1 MLBCOMHEHVFVSU-PKDNWHCCSA-N 0.000 claims description 2
PIQLXJIFTJKKML-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)propanoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)CCC1=CC=C(Cl)S1 PIQLXJIFTJKKML-SFHVURJKSA-N 0.000 claims description 2
FSUYPAIFVPOMGN-HNNXBMFYSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=CC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)C)=CC=C21 FSUYPAIFVPOMGN-HNNXBMFYSA-N 0.000 claims description 2
DPVOUFWSGIVGEM-PKDNWHCCSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC=C(Cl)S1 DPVOUFWSGIVGEM-PKDNWHCCSA-N 0.000 claims description 2
FUJIFMFKHBAPDZ-AWEZNQCLSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC(Br)=CS1 FUJIFMFKHBAPDZ-AWEZNQCLSA-N 0.000 claims description 2
FPUMBAUAQAVAQQ-FQEVSTJZSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(Cl)S1 FPUMBAUAQAVAQQ-FQEVSTJZSA-N 0.000 claims description 2
UGSAIWINCXVYTE-AWEZNQCLSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC=C(Cl)S1 UGSAIWINCXVYTE-AWEZNQCLSA-N 0.000 claims description 2
FXTXFJBVDHNYSY-KRWDZBQOSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-1-[[4-(ethylamino)quinolin-7-yl]methyl]-3-methylpiperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(C([C@@H]3C)=O)CC=3C=C4N=CC=C(C4=CC=3)NCC)=CC2=C1 FXTXFJBVDHNYSY-KRWDZBQOSA-N 0.000 claims description 2
BFLDPLPFCJQHRA-QFIPXVFZSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-3-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)COC)=CC2=C1 BFLDPLPFCJQHRA-QFIPXVFZSA-N 0.000 claims description 2
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QPMDRTXSMAQJQN-XBGMYJNYSA-N (3s)-4-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-3-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)COC)C(=O)\C=C\C1=CC=C(Cl)C=C1 QPMDRTXSMAQJQN-XBGMYJNYSA-N 0.000 claims description 2
RHESQXOYNCWQQP-FQEVSTJZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C=CC1=CC=C(N)N=C1 RHESQXOYNCWQQP-FQEVSTJZSA-N 0.000 claims description 2
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YVKIOYNKAVZPGJ-UHFFFAOYSA-N (6-chloro-1,3-benzoxazol-2-yl)methyl 4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazine-1-carboxylate Chemical compound C1=C(Cl)C=C2OC(COC(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 YVKIOYNKAVZPGJ-UHFFFAOYSA-N 0.000 claims description 2
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MELLWKWWNBDFBM-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroquinolin-3-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=CC2=CC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CN=C21 MELLWKWWNBDFBM-UHFFFAOYSA-N 0.000 claims description 2
AUJGNFAMGLGVTO-ZZXKWVIFSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(5-bromothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Br)S1 AUJGNFAMGLGVTO-ZZXKWVIFSA-N 0.000 claims description 2
SZLJRSQDUPBXJX-ZZXKWVIFSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Cl)S1 SZLJRSQDUPBXJX-ZZXKWVIFSA-N 0.000 claims description 2
VETFOERZUYQSAV-GQCTYLIASA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(6-chloro-1-benzothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(/C=C/C(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 VETFOERZUYQSAV-GQCTYLIASA-N 0.000 claims description 2
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VRFJPBDEXLTGGM-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)COC1=CC=C(Cl)S1 VRFJPBDEXLTGGM-UHFFFAOYSA-N 0.000 claims description 2
LUMULQIYXABLTQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-phenylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC(C=1)=CC=CC=1C1=CC=CC=C1 LUMULQIYXABLTQ-UHFFFAOYSA-N 0.000 claims description 2
IPSHUAIHILKQKU-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-phenylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC(C=C1)=CC=C1C1=CC=CC=C1 IPSHUAIHILKQKU-UHFFFAOYSA-N 0.000 claims description 2
GJVUGAVNWDVJAQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-prop-2-ynylpiperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN1CCN(CC#C)CC1=O GJVUGAVNWDVJAQ-UHFFFAOYSA-N 0.000 claims description 2
ALOOOPAWECXXQA-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-n-benzyl-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazine-2-carboxamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(CN(CC=1NC2=CC=C(Cl)C=C2C=1)C1)=O)C1C(=O)NCC1=CC=CC=C1 ALOOOPAWECXXQA-UHFFFAOYSA-N 0.000 claims description 2
RTALUUJEFBQNKW-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CC=C(C4=CC=3)N)=CC2=C1 RTALUUJEFBQNKW-UHFFFAOYSA-N 0.000 claims description 2
HOKVDVWDNLPHCS-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)C=CC1=CC=C(Cl)S1 HOKVDVWDNLPHCS-UHFFFAOYSA-N 0.000 claims description 2
JZJQEMMSTBRCLW-UHFFFAOYSA-N 1-[2-(pyridin-4-ylamino)ethyl]-4-thieno[2,3-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C=2SC3=NC=CC=C3C=2)CCN1CCNC1=CC=NC=C1 JZJQEMMSTBRCLW-UHFFFAOYSA-N 0.000 claims description 2
IPJUOWGTGHKFKN-UHFFFAOYSA-N 1-benzothiophene-5-carbonitrile Chemical compound N#CC1=CC=C2SC=CC2=C1 IPJUOWGTGHKFKN-UHFFFAOYSA-N 0.000 claims description 2
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
YICDGDQVHIITHG-KRWDZBQOSA-N 2-[2-[2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-2-oxoethoxy]-5-chlorothiophen-3-yl]acetic acid Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC=1SC(Cl)=CC=1CC(O)=O YICDGDQVHIITHG-KRWDZBQOSA-N 0.000 claims description 2
WBHNYUXNVGXADU-KRWDZBQOSA-N 2-[2-[2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-ethyl-3-oxopiperazin-1-yl]-2-oxoethoxy]-5-chlorothiophen-3-yl]acetic acid Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC=1SC(Cl)=CC=1CC(O)=O WBHNYUXNVGXADU-KRWDZBQOSA-N 0.000 claims description 2
UVJOUYXWFNHFIO-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]pyrrolo[3,2-c]pyridin-1-yl]acetamide Chemical compound N1=CC=C2N(CC(=O)N)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 UVJOUYXWFNHFIO-UHFFFAOYSA-N 0.000 claims description 2
ZEIJZPONRSMWPA-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-(2-pyridin-2-ylethyl)acetamide Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(=O)NCCC1=CC=CC=N1 ZEIJZPONRSMWPA-UHFFFAOYSA-N 0.000 claims description 2
HDXMCPUBYMWVNU-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]acetamide Chemical compound N1=CSC(CCNC(=O)CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1C HDXMCPUBYMWVNU-UHFFFAOYSA-N 0.000 claims description 2
WCDARHCRCJMTKX-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-methyl-n-pyridin-4-ylacetamide Chemical compound C1CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(=O)N(C)C1=CC=NC=C1 WCDARHCRCJMTKX-UHFFFAOYSA-N 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
AVXKXPDUVAYPFZ-UHFFFAOYSA-N 3-[[3-oxo-4-[(3-phenylphenyl)methyl]piperazin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2CC(=O)N(CC=3C=C(C=CC=3)C=3C=CC=CC=3)CC2)=C1 AVXKXPDUVAYPFZ-UHFFFAOYSA-N 0.000 claims description 2
NIJAEPFMFVZVEG-UHFFFAOYSA-N 3-[[4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2C(CN(CC=3NC4=CC(Cl)=CC=C4N=3)CC2)=O)=C1 NIJAEPFMFVZVEG-UHFFFAOYSA-N 0.000 claims description 2
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125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
FDYICBIXKAIKOA-UHFFFAOYSA-N 4-(1h-benzimidazol-2-ylsulfonyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC=C2NC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=NC2=C1 FDYICBIXKAIKOA-UHFFFAOYSA-N 0.000 claims description 2
GJXURDUUEYEMRQ-UHFFFAOYSA-N 4-(3-aminophenyl)sulfonyl-1-[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound NC1=CC=CC(S(=O)(=O)N2CC(=O)N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=C1 GJXURDUUEYEMRQ-UHFFFAOYSA-N 0.000 claims description 2
YXBVWWLBELAFNZ-UHFFFAOYSA-N 4-(5-chloro-1h-indole-2-carbonyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)C(=O)C=3NC4=CC=C(C=C4C=3)Cl)=CC2=C1 YXBVWWLBELAFNZ-UHFFFAOYSA-N 0.000 claims description 2
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MMLVQVYPEVEZGN-UHFFFAOYSA-N 4-(6-chlorothieno[2,3-b]pyridin-2-yl)sulfonyl-1-[2-(pyridin-4-ylamino)ethyl]piperazin-2-one Chemical compound S1C2=NC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CCNC1=CC=NC=C1 MMLVQVYPEVEZGN-UHFFFAOYSA-N 0.000 claims description 2
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SIFRVUXVQGVNGB-UHFFFAOYSA-N 4-[(5-chloro-1h-indol-2-yl)methyl]-1-[(4-chloroquinolin-7-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=NC2=CC(CN3CCN(CC3=O)CC=3NC4=CC=C(C=C4C=3)Cl)=CC=C21 SIFRVUXVQGVNGB-UHFFFAOYSA-N 0.000 claims description 2
FKTOGINWCZSRPX-UHFFFAOYSA-N 4-[(5-chloro-1h-indol-2-yl)methyl]-1-[[4-(2-hydroxyethylamino)quinolin-7-yl]methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CC=C(C4=CC=3)NCCO)=CC2=C1 FKTOGINWCZSRPX-UHFFFAOYSA-N 0.000 claims description 2
FTDXWBPXALILLG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(1,2,3,4-tetrahydroisoquinolin-6-ylmethyl)piperazin-2-one Chemical compound C1NCCC2=CC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC=C21 FTDXWBPXALILLG-UHFFFAOYSA-N 0.000 claims description 2
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ZFEMZURPEYWMCK-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(thieno[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2SC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 ZFEMZURPEYWMCK-UHFFFAOYSA-N 0.000 claims description 2
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ZTGGRTOLTZKBLG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-chloro-3-hydroxyphenyl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C(O)=CC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1 ZTGGRTOLTZKBLG-UHFFFAOYSA-N 0.000 claims description 2
GAFDXQLFXQXSRS-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-chlorophenyl)methyl]piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 GAFDXQLFXQXSRS-UHFFFAOYSA-N 0.000 claims description 2
QTGODLHCEUZWTR-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(5-hydroxypyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3N=C4C=CN(C=C4C=3)O)=CC2=C1 QTGODLHCEUZWTR-UHFFFAOYSA-N 0.000 claims description 2
MBROHYWUDGAGES-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[2-(pyridin-4-ylamino)ethyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CCNC1=CC=NC=C1 MBROHYWUDGAGES-UHFFFAOYSA-N 0.000 claims description 2
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HIBQXOYYVVAPHE-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-ethylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC)=CC=C21 HIBQXOYYVVAPHE-QHCPKHFHSA-N 0.000 claims 1
MHDJUZWRNRKHFV-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(2,3-dichlorophenoxy)acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=CC(Cl)=C1Cl MHDJUZWRNRKHFV-SFHVURJKSA-N 0.000 claims 1
XRQOAAVQXKNQTP-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chloro-5-methoxyphenoxy)acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC(Cl)=CC(OC)=C1 XRQOAAVQXKNQTP-NRFANRHFSA-N 0.000 claims 1
WIXGFFANUNUPPC-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chlorophenoxy)acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=CC(Cl)=C1 WIXGFFANUNUPPC-FQEVSTJZSA-N 0.000 claims 1
IYGKCNVPPPZLQE-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC(Cl)=CS1 IYGKCNVPPPZLQE-KRWDZBQOSA-N 0.000 claims 1
OOFKXVRAOJTQHF-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC1=CC(Cl)=CS1 OOFKXVRAOJTQHF-KRWDZBQOSA-N 0.000 claims 1
HDXIXQGVVFWHOU-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chloropyridin-3-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CN=CC(Cl)=C1 HDXIXQGVVFWHOU-IBGZPJMESA-N 0.000 claims 1
PQHRNGOKTQKUIQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)sulfanylacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CSC1=CC=C(Cl)S1 PQHRNGOKTQKUIQ-INIZCTEOSA-N 0.000 claims 1
ULVVVFNFXFHWSH-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CSC(Cl)=C1 ULVVVFNFXFHWSH-KRWDZBQOSA-N 0.000 claims 1
DIJYSOSJXAPYLC-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(6-chloropyridin-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=CC(Cl)=N1 DIJYSOSJXAPYLC-KRWDZBQOSA-N 0.000 claims 1
LKOMQQCIRWZDMF-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-[(6-chloropyridin-3-yl)amino]acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CNC1=CC=C(Cl)N=C1 LKOMQQCIRWZDMF-SFHVURJKSA-N 0.000 claims 1
KZSCTHBSZQVPTL-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-bromophenyl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=CC(Br)=C1 KZSCTHBSZQVPTL-NRFANRHFSA-N 0.000 claims 1
AXXIWXDROTYGFT-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-chlorophenyl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=CC(Cl)=C1 AXXIWXDROTYGFT-NRFANRHFSA-N 0.000 claims 1
NWCAWUFBLUEHKZ-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC(Br)=CS1 NWCAWUFBLUEHKZ-IBGZPJMESA-N 0.000 claims 1
BRLIDOSZZOYYBZ-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC(Br)=CS1 BRLIDOSZZOYYBZ-ZDUSSCGKSA-N 0.000 claims 1
KQSVXMPQUMBFSM-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorophenyl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(Cl)C=C1 KQSVXMPQUMBFSM-NRFANRHFSA-N 0.000 claims 1
AFBXZJRPVFJXNX-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorophenyl)propanoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)CCC1=CC=C(Cl)C=C1 AFBXZJRPVFJXNX-NRFANRHFSA-N 0.000 claims 1
PNSHQYXZORXFSB-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC(Cl)=CS1 PNSHQYXZORXFSB-IBGZPJMESA-N 0.000 claims 1
BYRCHTQDKADKBB-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC(Cl)=CS1 BYRCHTQDKADKBB-ZDUSSCGKSA-N 0.000 claims 1
CFUCEQZLZAMMLJ-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C=CC1=CC(Cl)=CS1 CFUCEQZLZAMMLJ-FQEVSTJZSA-N 0.000 claims 1
KFNNWEUHPLOBFM-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)but-2-enyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)CC=C(C)C1=CC=C(Cl)S1 KFNNWEUHPLOBFM-IBGZPJMESA-N 0.000 claims 1
JLEJMDXRGFSELX-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(Cl)S1 JLEJMDXRGFSELX-SFHVURJKSA-N 0.000 claims 1
RMBMHASNSWAOHY-PKDNWHCCSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethyl-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 RMBMHASNSWAOHY-PKDNWHCCSA-N 0.000 claims 1
POXQQNYNFKHQDV-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C=CC1=CC=C(Cl)S1 POXQQNYNFKHQDV-IBGZPJMESA-N 0.000 claims 1
BSSQYTLAFHGVAR-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-3-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CSC(Cl)=C1 BSSQYTLAFHGVAR-SFHVURJKSA-N 0.000 claims 1
PLGIBGUEBNPJSD-INIZCTEOSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=CC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)C)=CC=C21 PLGIBGUEBNPJSD-INIZCTEOSA-N 0.000 claims 1
CRBQZAIDKNSNSG-DTIOYNMSSA-N (3s)-1-[(4-chloroquinolin-7-yl)methyl]-3,5-dimethylpiperazin-2-one Chemical compound O=C1[C@H](C)NC(C)CN1CC1=CC=C(C(Cl)=CC=N2)C2=C1 CRBQZAIDKNSNSG-DTIOYNMSSA-N 0.000 claims 1
YBIPCKUOLFEIKF-ZDUSSCGKSA-N (3s)-3-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound O=C1[C@H](COC)NCCN1CC1=CC2=CN=CC=C2N1 YBIPCKUOLFEIKF-ZDUSSCGKSA-N 0.000 claims 1
YMFSGCWZLVFIES-KBPBESRZSA-N (3s,5s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3,5-dimethylpiperazin-2-one Chemical compound N1([C@@H](C)C(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)C[C@@H]1C)C(=O)C=CC1=CC=C(Cl)S1 YMFSGCWZLVFIES-KBPBESRZSA-N 0.000 claims 1
OTVJALKAUIMVDT-UHFFFAOYSA-N 1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-thieno[2,3-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound C1=CN=C2SC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=C1 OTVJALKAUIMVDT-UHFFFAOYSA-N 0.000 claims 1
YIQKAPCYLQPOKQ-UHFFFAOYSA-N 1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-thieno[3,2-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound C1=CC=C2SC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=N1 YIQKAPCYLQPOKQ-UHFFFAOYSA-N 0.000 claims 1
PZQGRGDARNXLSP-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2,5-dimethylpyrrole Chemical compound CC1=CC=C(C)N1C1=CC(Cl)=CC(Cl)=C1 PZQGRGDARNXLSP-UHFFFAOYSA-N 0.000 claims 1
SEKKRDRUSDOVRH-UHFFFAOYSA-N 1-[(1-aminoisoquinolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=C4C=CN=C(C4=C3)N)=CC2=C1 SEKKRDRUSDOVRH-UHFFFAOYSA-N 0.000 claims 1
YEUZWNMZCJAJLS-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-(6-chlorothieno[2,3-b]pyridin-2-yl)sulfonylpiperazin-2-one Chemical compound C1=C(Cl)N=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC4=CC=C(N=C4C=C3)N)=CC2=C1 YEUZWNMZCJAJLS-UHFFFAOYSA-N 0.000 claims 1
VAJHDXWBJMGSQJ-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(4-methoxyphenyl)methyl]piperazin-2-one Chemical compound C1=CC(OC)=CC=C1CN1CC(=O)N(CC=2C=C3C=CC(N)=NC3=CC=2)CC1 VAJHDXWBJMGSQJ-UHFFFAOYSA-N 0.000 claims 1
NNHTYOYEVGEYDN-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC4=CC=C(N=C4C=C3)N)=CC2=C1 NNHTYOYEVGEYDN-UHFFFAOYSA-N 0.000 claims 1
NDFNUQOROBVJAA-XBXARRHUSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C1=CC2=NC(N)=CC=C2C=C1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Cl)S1 NDFNUQOROBVJAA-XBXARRHUSA-N 0.000 claims 1
ORAFZAGZZVMVSE-UHFFFAOYSA-N 1-[(3-amino-1h-indazol-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3)=O)CC=3C=C4NN=C(C4=CC=3)N)=CC2=C1 ORAFZAGZZVMVSE-UHFFFAOYSA-N 0.000 claims 1
PJTCXZKNDPPAQB-UHFFFAOYSA-N 1-[(4-amino-1h-pyrrolo[3,2-c]pyridin-2-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3NC=4C=CN=C(C=4C=3)N)=CC2=C1 PJTCXZKNDPPAQB-UHFFFAOYSA-N 0.000 claims 1
UCGMUNYQWRKBOE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-(1-methoxyethyl)piperazin-2-one Chemical compound O=C1C(C(C)OC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 UCGMUNYQWRKBOE-UHFFFAOYSA-N 0.000 claims 1
SEPPQPTZSZNXPZ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound O=C1C(CC(C)C)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 SEPPQPTZSZNXPZ-UHFFFAOYSA-N 0.000 claims 1
YULQKYGTFCAZQO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-(ethoxymethyl)piperazin-2-one Chemical compound O=C1C(COCC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 YULQKYGTFCAZQO-UHFFFAOYSA-N 0.000 claims 1
MQPPDURTNZUCEJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound O=C1C(COC)NCC(C)N1CC1=CC=C(C(N)=NC=N2)C2=C1 MQPPDURTNZUCEJ-UHFFFAOYSA-N 0.000 claims 1
HDCLQBCLRJGSGR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound O=C1C(COC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 HDCLQBCLRJGSGR-UHFFFAOYSA-N 0.000 claims 1
VRHFVXWZTMLFLT-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-benzylpiperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C1=O)CCNC1CC1=CC=CC=C1 VRHFVXWZTMLFLT-UHFFFAOYSA-N 0.000 claims 1
PQBLMXHPUJIRFO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-butylpiperazin-2-one Chemical compound O=C1C(CCCC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 PQBLMXHPUJIRFO-UHFFFAOYSA-N 0.000 claims 1
RGKINQODOCLLDW-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-ethylpiperazin-2-one Chemical compound O=C1C(CC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 RGKINQODOCLLDW-UHFFFAOYSA-N 0.000 claims 1
NMUOQCRCNSXVLC-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-methylpiperazin-2-one Chemical compound O=C1C(C)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 NMUOQCRCNSXVLC-UHFFFAOYSA-N 0.000 claims 1
MKGCGHVUNHUNTJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-propan-2-ylpiperazin-2-one Chemical compound O=C1C(C(C)C)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 MKGCGHVUNHUNTJ-UHFFFAOYSA-N 0.000 claims 1
XKSPVFNZBIDNPC-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-3-propylpiperazin-2-one Chemical compound O=C1C(CCC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 XKSPVFNZBIDNPC-UHFFFAOYSA-N 0.000 claims 1
UXMSIRHWNBNVRZ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(1h-benzimidazol-2-ylmethyl)piperazin-2-one Chemical compound C1=CC=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 UXMSIRHWNBNVRZ-UHFFFAOYSA-N 0.000 claims 1
DEPKQAACNKYEPW-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=NC=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 DEPKQAACNKYEPW-UHFFFAOYSA-N 0.000 claims 1
RLHZDEXEVGRRTQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(3-chloro-1h-indole-6-carbonyl)piperazin-2-one Chemical compound C1=C2C(Cl)=CNC2=CC(C(=O)N2CCN(C(C2)=O)CC=2C=C3N=CN=C(C3=CC=2)N)=C1 RLHZDEXEVGRRTQ-UHFFFAOYSA-N 0.000 claims 1
AYIRDMGAXISONP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(4-methyl-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC3=O)CC=3SC=4C=CC=C(C=4C=3)C)=CC=C21 AYIRDMGAXISONP-UHFFFAOYSA-N 0.000 claims 1
URNXXYSVPPVRPK-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5,7-dichloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC(Cl)=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 URNXXYSVPPVRPK-UHFFFAOYSA-N 0.000 claims 1
QFPJLWTUZOFRPA-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1-benzofuran-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=C2OC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 QFPJLWTUZOFRPA-UHFFFAOYSA-N 0.000 claims 1
HDFNWMFVGWFMHI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1-methylindol-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=C2N(C)C(CN3CC(=O)N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=CC2=C1 HDFNWMFVGWFMHI-UHFFFAOYSA-N 0.000 claims 1
WVBPBECTCVJFFR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-n-[2-(methylamino)-2-oxoethyl]-6-oxopiperazine-2-carboxamide Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)CC3C(=O)NCC(=O)NC)=CC=C21 WVBPBECTCVJFFR-UHFFFAOYSA-N 0.000 claims 1
VPZLWZLCESJIJL-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6,7-dichloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C(Cl)=C2SC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 VPZLWZLCESJIJL-UHFFFAOYSA-N 0.000 claims 1
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230000001717 pathogenic effect Effects 0.000 claims 1
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125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
PEILIKNAQRIDJS-NSCUHMNNSA-N methyl (e)-3-(4-chlorothiophen-2-yl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC(Cl)=CS1 PEILIKNAQRIDJS-NSCUHMNNSA-N 0.000 description 1
SVBPOUYXRNTUMN-UHFFFAOYSA-N methyl 2-[[3-[tert-butyl(dimethyl)silyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-phenylmethoxycarbonylamino]acetate Chemical compound CC(C)(C)[Si](C)(C)OCC(NC(=O)OC(C)(C)C)CN(CC(=O)OC)C(=O)OCC1=CC=CC=C1 SVBPOUYXRNTUMN-UHFFFAOYSA-N 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000002297 mitogenic effect Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
HWWVAHCWJLGKLW-UHFFFAOYSA-N n,n-dimethylhydroxylamine;hydron;chloride Chemical compound Cl.CN(C)O HWWVAHCWJLGKLW-UHFFFAOYSA-N 0.000 description 1
PEAZSVAAOGKKJD-UHFFFAOYSA-N n-(3-chlorophenyl)-2-methyl-3-phenylprop-2-enamide Chemical compound C=1C=CC(Cl)=CC=1NC(=O)C(C)=CC1=CC=CC=C1 PEAZSVAAOGKKJD-UHFFFAOYSA-N 0.000 description 1
MJFCOXATGBYERZ-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=N1 MJFCOXATGBYERZ-UHFFFAOYSA-N 0.000 description 1
BTHPYVXLLWGRIE-UHFFFAOYSA-N n-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]acetamide Chemical compound CC(=O)NCCC=1SC=NC=1C BTHPYVXLLWGRIE-UHFFFAOYSA-N 0.000 description 1
YYTKWJLYWZAXFP-UHFFFAOYSA-N n-[4-(dimethylamino)-1,3,5-triazin-2-yl]acetamide Chemical compound CN(C)C1=NC=NC(NC(C)=O)=N1 YYTKWJLYWZAXFP-UHFFFAOYSA-N 0.000 description 1
YMRQGDVRCHGJPW-UHFFFAOYSA-N n-benzyl-2,3,5,6-tetrachloropyridin-4-amine Chemical compound ClC1=NC(Cl)=C(Cl)C(NCC=2C=CC=CC=2)=C1Cl YMRQGDVRCHGJPW-UHFFFAOYSA-N 0.000 description 1
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MPBMBTVWEVCXNU-UHFFFAOYSA-N n-methyl-n-pyridin-4-ylacetamide Chemical compound CC(=O)N(C)C1=CC=NC=C1 MPBMBTVWEVCXNU-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MVCZKPMTGFFULA-UHFFFAOYSA-N n-pyrimidin-4-ylacetamide Chemical compound CC(=O)NC1=CC=NC=N1 MVCZKPMTGFFULA-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000012026 peptide coupling reagents‎ Substances 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical class O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 1
BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 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
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229940039716 prothrombin Drugs 0.000 description 1
108010014806 prothrombinase complex Proteins 0.000 description 1
230000005588 protonation Effects 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
238000007614 solvation Methods 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000008685 targeting Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
FCMLWBBLOASUSO-UHFFFAOYSA-N tert-butyl 3-oxopiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNC(=O)C1 FCMLWBBLOASUSO-UHFFFAOYSA-N 0.000 description 1
MADJAJBGQFKOGI-UHFFFAOYSA-N tert-butyl N-(3-tert-butylsilyloxy-3-methyl-1-oxobutan-2-yl)carbamate Chemical compound C(C)(C)(C)OC(NC(C=O)C(O[SiH2]C(C)(C)C)(C)C)=O MADJAJBGQFKOGI-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-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
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
ZASCXWTVGGZQIZ-UHFFFAOYSA-N thieno[3,2-d]pyrimidin-2-amine Chemical compound NC1=NC=C2SC=CC2=N1 ZASCXWTVGGZQIZ-UHFFFAOYSA-N 0.000 description 1
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
210000005167 vascular cell Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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BG104633A 1998-01-27 2000-07-25 ЗАМЕСТЕНИ ОКСОАЗАХЕТЕРОЦИКЛЕНИ ИНХИБИТОРИ НА ФАКТОР Ха BG104633A (bg)

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US7270798P	1998-01-27	1998-01-27
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AU (1)	AU745425B2 (et)
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- 1999-01-27 UA UA2000085034A patent/UA59433C2/uk unknown
- 1999-01-27 CN CN99803501A patent/CN1291892A/zh active Pending
- 1999-01-27 JP JP2000528286A patent/JP4676613B2/ja not_active Expired - Fee Related
- 1999-01-27 TR TR2000/02182T patent/TR200002182T2/xx unknown
- 1999-01-27 AT AT99906684T patent/ATE346050T1/de not_active IP Right Cessation
- 1999-01-27 EP EP99906684A patent/EP1051176B1/en not_active Expired - Lifetime
- 1999-01-27 KR KR1020007008221A patent/KR20010034442A/ko not_active Withdrawn
- 1999-01-27 ZA ZA9900607A patent/ZA99607B/xx unknown
- 1999-01-27 DE DE69934093T patent/DE69934093T2/de not_active Expired - Lifetime
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- 1999-01-27 CA CA2319198A patent/CA2319198C/en not_active Expired - Fee Related
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- 1999-01-27 BR BR9907300-5A patent/BR9907300A/pt not_active IP Right Cessation
- 1999-01-27 AU AU26533/99A patent/AU745425B2/en not_active Ceased
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2000
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Also Published As

Publication number	Publication date
AU745425B2 (en)	2002-03-21
EP1051176B1 (en)	2006-11-22
YU47600A (sh)	2002-09-19
UA59433C2 (uk)	2003-09-15
SK11082000A3 (sk)	2001-01-18
AU2653399A (en)	1999-08-09
EP1051176A1 (en)	2000-11-15
ATE346050T1 (de)	2006-12-15
PL342243A1 (en)	2001-06-04
EE200000435A (et)	2002-02-15
ZA99607B (en)	1999-07-27
CA2319198C (en)	2011-02-22
DE69934093T2 (de)	2007-06-21
NO20003808L (no)	2000-09-26
BR9907300A (pt)	2000-10-24
KR20010034442A (ko)	2001-04-25
IL137517A (en)	2006-12-10
WO1999037304A1 (en)	1999-07-29
DE69934093D1 (de)	2007-01-04
US7612075B2 (en)	2009-11-03
IL137517A0 (en)	2001-07-24
EP1051176A4 (en)	2002-06-12
EA200000768A1 (ru)	2001-06-25
AP2000001889A0 (en)	2000-09-30
US20040102450A1 (en)	2004-05-27
JP4676613B2 (ja)	2011-04-27
HUP0101810A3 (en)	2002-05-28
IS5574A (is)	2000-07-25
CA2319198A1 (en)	1999-07-29
NO20003808D0 (no)	2000-07-25
HUP0101810A2 (hu)	2002-04-29
TR200002182T2 (tr)	2000-12-21
JP2002501024A (ja)	2002-01-15
CN1291892A (zh)	2001-04-18

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JP4829449B2 (ja)	2011-12-07	置換オキソアザヘテロシクリル化合物
JP2003529531A (ja)	2003-10-07	置換オキソアザへテロシクリルＸａ因子阻害剤
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US6602864B1 (en)	2003-08-05	Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds
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HK1035489A (en)	2001-11-30	Substituted oxoazaheterocyclyl factor xa inhibitors