HRP20161530T1 - 2-(azaindol-2-il)benzimidazoli kao pad4 inhibitori - Google Patents
2-(azaindol-2-il)benzimidazoli kao pad4 inhibitori Download PDFInfo
- Publication number
- HRP20161530T1 HRP20161530T1 HRP20161530TT HRP20161530T HRP20161530T1 HR P20161530 T1 HRP20161530 T1 HR P20161530T1 HR P20161530T T HRP20161530T T HR P20161530TT HR P20161530 T HRP20161530 T HR P20161530T HR P20161530 T1 HRP20161530 T1 HR P20161530T1
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- Prior art keywords
- pyrrolo
- pyridin
- methanone
- benzo
- methyl
- Prior art date
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- VEZJRJGLFIXQHG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-1h-benzimidazole Chemical class C1=CC=C2NC(C=3NC4=CC=CC=C4N=3)=NC2=C1 VEZJRJGLFIXQHG-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 7
- -1 (R)-3-aminopiperidin-1-yl Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- PYUZHTRYLVLMAP-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCCC(N)C1 PYUZHTRYLVLMAP-UHFFFAOYSA-N 0.000 claims 1
- YEKXWBBPTLBIFX-UHFFFAOYSA-N (3-aminopiperidin-1-yl)-[2-(1-ethylpyrrolo[3,2-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CN=CC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCCC(N)C1 YEKXWBBPTLBIFX-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- DFMWXZVRHCUIDX-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[1-methyl-2-[1-(2,2,2-trifluoroethyl)pyrrolo[2,3-b]pyridin-2-yl]benzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC(F)(F)F)=NC2=CC=1C(=O)N1CCC[C@@H](N)C1 DFMWXZVRHCUIDX-MRXNPFEDSA-N 0.000 claims 1
- QWCHTDZPCMJADP-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-hydroxypyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(O)=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 QWCHTDZPCMJADP-MRXNPFEDSA-N 0.000 claims 1
- CUZDPEBQVSHMAS-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-methoxypyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(OC)=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 CUZDPEBQVSHMAS-QGZVFWFLSA-N 0.000 claims 1
- MKKDRCQQVXGTHG-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethyl-5-methoxypyrrolo[2,3-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC(OC)=NC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 MKKDRCQQVXGTHG-QGZVFWFLSA-N 0.000 claims 1
- XMKOCOWOTAXPIB-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-1-methyl-7-(trifluoromethoxy)benzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC(F)(F)F)C=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 XMKOCOWOTAXPIB-MRXNPFEDSA-N 0.000 claims 1
- PYUZHTRYLVLMAP-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 PYUZHTRYLVLMAP-QGZVFWFLSA-N 0.000 claims 1
- JCCVZBCVMBEDEN-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=CN=C2N(CC)C=1C(N(C1=C(OC)C=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 JCCVZBCVMBEDEN-QGZVFWFLSA-N 0.000 claims 1
- PXEKOCDKODNCAO-QGZVFWFLSA-N [(3r)-3-aminopiperidin-1-yl]-[2-(1-ethylpyrrolo[2,3-c]pyridin-2-yl)-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C2=CC=NC=C2N(CC)C=1C(N(C1=CC=2)C)=NC1=CC=2C(=O)N1CCC[C@@H](N)C1 PXEKOCDKODNCAO-QGZVFWFLSA-N 0.000 claims 1
- PZGSGOGBUMTSJY-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC3CC3)=NC2=CC=1C(=O)N1CCC[C@@H](N)C1 PZGSGOGBUMTSJY-LJQANCHMSA-N 0.000 claims 1
- KNMCDXAIVNPMQX-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C=2C(OC)=CC(C(=O)N3C[C@H](N)CCC3)=CC=2N=C1C1=CC2=CC=CN=C2N1CC1CC1 KNMCDXAIVNPMQX-LJQANCHMSA-N 0.000 claims 1
- NGVGPCGPMJWOCO-MRXNPFEDSA-N [(3r)-3-aminopiperidin-1-yl]-[7-methoxy-1-methyl-2-[1-(2,2,2-trifluoroethyl)pyrrolo[2,3-b]pyridin-2-yl]benzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(F)(F)F)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 NGVGPCGPMJWOCO-MRXNPFEDSA-N 0.000 claims 1
- FQGRLSQSAFNRCE-LJQANCHMSA-N [(3r)-3-aminopiperidin-1-yl]-[7-methoxy-2-[1-(2-methoxy-2-methylpropyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=2N=C(C=3N(C4=NC=CC=C4C=3)CC(C)(C)OC)N(C)C=2C(OC)=CC=1C(=O)N1CCC[C@@H](N)C1 FQGRLSQSAFNRCE-LJQANCHMSA-N 0.000 claims 1
- LGMQWHDIEKFXIE-PGRDOPGGSA-N [(3s,4r)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-1-methylbenzimidazol-5-yl]methanone Chemical compound C=1C=C2N(C)C(C=3N(C4=NC=CC=C4C=3)CC3CC3)=NC2=CC=1C(=O)N1CC[C@@H](O)[C@@H](N)C1 LGMQWHDIEKFXIE-PGRDOPGGSA-N 0.000 claims 1
- SHBUAYSOPVZNDD-GHTZIAJQSA-N [(3s,4r)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone Chemical compound CN1C=2C(OC)=CC(C(=O)N3C[C@H](N)[C@H](O)CC3)=CC=2N=C1C1=CC2=CC=CN=C2N1CC1CC1 SHBUAYSOPVZNDD-GHTZIAJQSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
Classifications
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
-
- 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
- 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
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (14)
1. Spoj sa formulom (I):
[image]
gdje;
R1 je vodik ili C1-6alkil;
R2 je vodik, C1-6alkil, perhalometilC0-5alkil-O-, ili C1-6alkoksi;
R3 je vodik, C1-6alkil, ili C1-6alkoksiC1-6alkil;
R4 je vodik, C1-6alkil, perhalometilC1-6alkil; ili nesupstituirani C3-6cikloalkilC1-6alkil;
A je C-R5 ili N;
B je C-R6 ili N;
D je C-R7 ili N;
uz uvjet da najmanje jedan od A, B, i D, je N;
R5 je vodik ili C1-6alkil;
R6 je vodik ili C1-6alkil;
R7 je vodik, C1-6alkil, C1-6alkoksi, ili hidroksi;
R8 je vodik ili C1-6alkil, uz uvjet da jedan od R4 i R8 je vodik;
R9 je vodik ili hidroksi;
R10 je vodik ili C1-6alkil;
ili njegova sol.
2. Spoj sa formulom (I) ili njegova sol prema patentnom zahtjevu 1 gdje R1 je vodik.
3. Spoj sa formulom (I) ili njegova sol prema patentnom zahtjevu 1 ili patentnom zahtjevu 2 gdje R2 je vodik ili C1-6alkoksi.
4. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R3 je C1-6alkil.
5. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R4 je C1-6alkil, nesupstituirani C3-6cikloalkilC1-6alkil, ili perhalometilC1-6alkil.
6. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R6 je vodik.
7. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R7 je vodik.
8. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R8 je vodik.
9. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R9 je vodik.
10. Spoj sa formulom (I) ili njegova sol prema bilo kojem od prethodnih patentnih zahtjeva gdje R10 je vodik.
11. Spoj sa formulom (I) ili njegova sol prema patentnom zahtjevu 1, odabrano sa liste koji se sastoji od:
1-{[2-(1-etil-1H-pirolo[3,2-c]piridin-2-il)-1-metil-1H-benzimidazol-5-il]karbonil}-3-piperidinamin;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-c]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(1-metil-2-(1-(2,2,2-trifluoroetil)-1H-pirolo[2,3-b]piridin-2-il)-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-(ciklopropilmetil)-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-5-metoksi-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-5-metoksi-1H-pirolo[2,3-c]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
2-(5-{[(3R)-3-amino-1-piperidinil]karbonil}-1-metil-1H-benzimidazol-2-il)-1-etil-1H-pirolo[2,3-b]piridin-5-ol;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-(ciklopropilmetil)-1 H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-
benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(7-metoksi-1-metil-2-(1-(2,2,2-trifluoroetil)-1H-pirolo[2,3-b]piridin-2-il)-1H-benzo[d]imidazol-5-il)metanon;
(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
((3S,4R)-3-amino-4-hidroksipiperidin-1-il)(2-(1-(ciklopropilmetil)-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
((3S,4R)-3-amino-4-hidroksipiperidin-1-il)(2-(1-(ciklopropilmetil)-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-1-metil-7-(trifluorometoksi)-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(7-metoksi-1-metil-2-(1-neopentil-1H-pirolo[2,3-b]piridin-2-il)-1H-benzo[d]imidazol-5-il)metanon;
((R)-3-aminopiperidin-1-il)(7-metoksi-1-metil-2-(1-(2-metilbutil)-1H-pirolo[2,3-b]piridin-2-il)-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-1-etil-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-(2-metoksietil)-1H-benzo[d]imidazol-5-il)metanon;
(S)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-etil-1H-pirolo[2,3-b]piridin-2-il)-1-izobutil-7-metoksi-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(7-metoksi-2-(1-(2-metoksi-2-metilpropil)-1H-pirolo[2,3-b]piridin-2-il)-1-metil-1H-benzo[d]imidazol-5-il)metanon;
(R)-(3-aminopiperidin-1-il)(2-(1-izobutil-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-benzo[d]imidazol-5-il)metanon, i;
((cis)-5-amino-2-metilpiperidin-1-il)(2-(1-(ciklopropilmetil)-1H-pirolo[2,3-b]piridin-2-il)-7-metoksi-1-metil-1H-benzo[d]imidazol-5-il)metanon,
i njihovih soli.
12. Spoj sa formulom (I) prema bilo kojem od patentnih zahtjeva 1 do 11 je farmaceutski prihvatljiva sol.
13. Spoj sa formulom (I) kao što je definirano prema bilo kojem od patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol, za primjenu u liječenju reumatoidnog artritisa, vaskulitisa, eritemskog sistemskog lupusa, ulcerativnog kolitisa, raka, cistične fibroze, astme, kutanog eritemskog lupusa, ili psorijaze.
14. Farmaceutska kompozicija koja sadrži spoj sa formulom (I) kao što je definirano prema bilo kojem od patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol, i jedan ili više farmaceutski prihvatljivih ekscipijenasa..
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2012/064649 WO2014015905A1 (en) | 2012-07-26 | 2012-07-26 | 2 - (azaindol- 2 -yl) benz imidazoles as pad4 inhibitors |
| EP12740581.9A EP2877467B1 (en) | 2012-07-26 | 2012-07-26 | 2-(azaindol-2-yl)benzimidazoles as pad4 inhibitors |
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| HRP20161530T1 true HRP20161530T1 (hr) | 2017-02-10 |
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| HRP20161530TT HRP20161530T1 (hr) | 2012-07-26 | 2016-11-21 | 2-(azaindol-2-il)benzimidazoli kao pad4 inhibitori |
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| US (4) | US9127003B2 (hr) |
| EP (1) | EP2877467B1 (hr) |
| JP (1) | JP6063567B2 (hr) |
| KR (1) | KR101916443B1 (hr) |
| CN (1) | CN104470919B (hr) |
| AU (1) | AU2012386257B2 (hr) |
| BR (1) | BR112015001545B1 (hr) |
| CA (1) | CA2879341C (hr) |
| CY (1) | CY1118524T1 (hr) |
| DK (1) | DK2877467T3 (hr) |
| ES (1) | ES2609126T3 (hr) |
| HR (1) | HRP20161530T1 (hr) |
| HU (1) | HUE033294T2 (hr) |
| IN (1) | IN2014KN02935A (hr) |
| LT (1) | LT2877467T (hr) |
| PL (1) | PL2877467T3 (hr) |
| PT (1) | PT2877467T (hr) |
| RS (1) | RS55684B1 (hr) |
| RU (1) | RU2611010C2 (hr) |
| SI (1) | SI2877467T1 (hr) |
| SM (1) | SMT201700052B (hr) |
| WO (1) | WO2014015905A1 (hr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6703553B2 (ja) * | 2015-05-21 | 2020-06-03 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｐａｄ４阻害剤としてのベンゾイミダゾール誘導体 |
| AR107032A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores bicíclicos de pad4 |
| AR107030A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores aza-bencimidazol de pad4 |
| CA3015482A1 (en) * | 2016-02-23 | 2017-08-31 | Padlock Therapeutics, Inc. | Heteroaryl inhibitors of pad4 |
| CN107188867A (zh) * | 2016-03-14 | 2017-09-22 | 中国科学院天津工业生物技术研究所 | 精氨酸脱亚氨酶4的抑制剂 |
| US10703741B2 (en) | 2016-07-27 | 2020-07-07 | Padlock Therapeutics, Inc. | Covalent inhibitors of PAD4 |
| KR102502992B1 (ko) * | 2016-09-12 | 2023-02-24 | 패들락 테라퓨틱스, 인코포레이티드 | Pad4의 헤테로아릴 억제제 |
| US11208386B2 (en) | 2016-12-02 | 2021-12-28 | University Of Massachusetts | Inhibitors of protein arginine deiminases (PADs) and methods of preparation and use thereof |
| CN108689946B (zh) * | 2017-04-12 | 2022-10-18 | 中国科学院上海药物研究所 | 2-取代硫基乙酰胺类化合物及其制备方法和应用 |
| CA3073656C (en) | 2017-09-22 | 2024-03-05 | Jubilant Epipad LLC | Heterocyclic compounds as pad inhibitors |
| AU2018352142B2 (en) * | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| SG11202004143XA (en) | 2017-11-06 | 2020-06-29 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| CN111542523B (zh) | 2017-11-24 | 2024-03-29 | 朱比连特埃皮斯科瑞有限责任公司 | 作为prmt5抑制剂的杂环化合物 |
| JP2021515043A (ja) | 2018-02-26 | 2021-06-17 | 南京薬捷安康生物科技有限公司Ｎａｎｊｉｎｇ Ｔｒａｎｓｔｈｅｒａ Ｂｉｏｓｃｉｅｎｃｅｓ Ｃｏ．， Ｌｔｄ． | ペプチジルアルギニンデイミナーゼ阻害剤及びその使用 |
| CA3093527A1 (en) | 2018-03-13 | 2019-09-19 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| KR20210042932A (ko) * | 2018-08-08 | 2021-04-20 | 브리스톨-마이어스 스큅 컴퍼니 | Pad4 억제제로서의 치환된 벤즈이미다졸 |
| JP7447080B2 (ja) | 2018-08-08 | 2024-03-11 | ブリストル－マイヤーズ スクイブ カンパニー | Ｐａｄ４阻害剤としての置換チエノピロール |
| CN112805067A (zh) * | 2018-08-08 | 2021-05-14 | 百时美施贵宝公司 | Pad酶的吲哚及氮杂吲哚抑制剂 |
| CN112789087A (zh) * | 2018-08-08 | 2021-05-11 | 百时美施贵宝公司 | Pad酶的苯并咪唑抑制剂 |
| CN109369513B (zh) * | 2018-11-20 | 2020-08-25 | 都创(上海)医药科技有限公司 | 一种fbdd常用分子片段的制备方法 |
| US20230002328A1 (en) * | 2019-07-03 | 2023-01-05 | University Of Massachusetts | Inhibitors of protein arginine deiminase 1 and methods of preparation and use thereof |
| TW202115083A (zh) * | 2019-09-27 | 2021-04-16 | 大陸商南京藥捷安康生物科技有限公司 | 肽醯精胺酸脫亞胺酶抑制劑及其用途 |
| EP4100405A1 (en) * | 2020-02-06 | 2022-12-14 | Bristol-Myers Squibb Company | Macrocyclic pad4 inhibitors useful as immunosuppressant |
| TW202140477A (zh) * | 2020-02-12 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 雜環ｐａｄ４抑制劑 |
| CN111265526B (zh) * | 2020-04-09 | 2021-03-19 | 黑龙江中医药大学 | 一种治疗胃癌的药物及其制备方法 |
| EP4143189A1 (en) | 2020-04-30 | 2023-03-08 | Gilead Sciences, Inc. | Macrocyclic inhibitors of peptidylarginine deiminases |
| EP4211171A2 (en) | 2020-09-10 | 2023-07-19 | Precirix N.V. | Antibody fragment against fap |
| US20230365589A1 (en) | 2020-09-18 | 2023-11-16 | Sumitomo Pharma Co., Ltd. | Novel amine derivatives |
| TW202241884A (zh) | 2020-12-22 | 2022-11-01 | 美商基利科學股份有限公司 | 肽基精胺酸去亞胺酶之抑制劑 |
| CA3238577A1 (en) | 2021-11-15 | 2023-05-19 | Regor Therapeutics, Inc. | Pad4 inhibitors and use thereof |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| WO2023213801A1 (en) | 2022-05-02 | 2023-11-09 | Precirix N.V. | Pre-targeting |
| WO2023230609A1 (en) * | 2022-05-26 | 2023-11-30 | Celgene Corporation | Heterocyclic pad4 inhibitors |
| WO2024109945A1 (en) * | 2022-11-24 | 2024-05-30 | Helios Huaming Biopharma Co., Ltd. | Selenium containing heterocycle compounds and use thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU570439B2 (en) | 1983-03-28 | 1988-03-17 | Compression Labs, Inc. | A combined intraframe and interframe transform coding system |
| DE69637257T2 (de) | 1995-04-14 | 2008-06-12 | Smithkline Beecham Corp. | Verfahren zur Herstellung eines Dosierinhalators |
| TW533865U (en) | 1997-06-10 | 2003-05-21 | Glaxo Group Ltd | Dispenser for dispensing medicament and actuation indicating device |
| DE69928414T2 (de) * | 1998-09-18 | 2006-08-03 | Abbott Gmbh & Co. Kg | 4-aminopyrrolopyrimidine als kinaseinhibitoren |
| US6119853A (en) | 1998-12-18 | 2000-09-19 | Glaxo Wellcome Inc. | Method and package for storing a pressurized container containing a drug |
| US6390291B1 (en) | 1998-12-18 | 2002-05-21 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6315112B1 (en) | 1998-12-18 | 2001-11-13 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6352152B1 (en) | 1998-12-18 | 2002-03-05 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| EP1226119B1 (en) * | 1999-10-19 | 2005-03-16 | MERCK & CO. INC. | Tyrosine kinase inhibitors |
| EP1263759B1 (en) | 1999-12-24 | 2010-09-08 | Aventis Pharma Limited | Azaindoles |
| GB0115393D0 (en) | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| WO2003000690A1 (en) | 2001-06-25 | 2003-01-03 | Aventis Pharmaceuticals Inc. | Synthesis of heterocyclic compounds employing microwave technology |
| ES2388434T3 (es) | 2003-11-03 | 2012-10-15 | Glaxo Group Limited | Dispositivo de administración de fluido |
| JP2007511596A (ja) | 2003-11-17 | 2007-05-10 | ファイザー・プロダクツ・インク | 癌の治療において有用なピロロピリミジン化合物 |
| FR2862971B1 (fr) | 2003-11-28 | 2006-03-24 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et d'imidazo-pyridine et leur utilisation en tant que medicament |
| US7429611B2 (en) | 2004-09-23 | 2008-09-30 | Bristol-Myers Squibb Company | Indole inhibitors of 15-lipoxygenase |
| EP2205085A1 (en) | 2007-09-25 | 2010-07-14 | Merck Sharp & Dohme Corp. | 2-aryl or heteroaryl indole derivatives |
| US20090311217A1 (en) | 2008-05-28 | 2009-12-17 | Wyeth | 3-substituted-1h-indole compounds, their use as mtor kinase and pi3 kinase inhibitors, and their syntheses |
| RU2011106786A (ru) * | 2008-07-23 | 2012-08-27 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Ингибиторы пиразолопиридинкиназы |
| CN104030987B (zh) * | 2009-04-02 | 2017-04-12 | 默克雪兰诺有限公司 | 二氢乳清酸脱氢酶抑制剂 |
| WO2010118208A1 (en) | 2009-04-09 | 2010-10-14 | Exelixis, Inc. | Benzoxazepin-4- (5h) -yl derivatives and their use to treat cancer |
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