HRP20192041T1 - [derivati 7-(morfolinil)-2-(n-piperazinil) metil tieno [2, 3-c]piridina kao lijekovi protiv raka] - Google Patents
[derivati 7-(morfolinil)-2-(n-piperazinil) metil tieno [2, 3-c]piridina kao lijekovi protiv raka] Download PDFInfo
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- HRP20192041T1 HRP20192041T1 HRP20192041TT HRP20192041T HRP20192041T1 HR P20192041 T1 HRP20192041 T1 HR P20192041T1 HR P20192041T T HRP20192041T T HR P20192041TT HR P20192041 T HRP20192041 T HR P20192041T HR P20192041 T1 HRP20192041 T1 HR P20192041T1
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- Prior art keywords
- methyl
- compound
- thieno
- pyridin
- substituted
- Prior art date
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- UFCFTDIPQQTTNA-UHFFFAOYSA-N 2-methylthieno[2,3-c]pyridine Chemical class C1=NC=C2SC(C)=CC2=C1 UFCFTDIPQQTTNA-UHFFFAOYSA-N 0.000 title 1
- 239000002246 antineoplastic agent Substances 0.000 title 1
- 229940041181 antineoplastic drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- -1 -nitro Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- IMKNPBUMAAHTIS-UHFFFAOYSA-N 5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]pyrimidin-2-amine Chemical compound CS(=O)(=O)N1CCN(CC1)CC1=CC=2C(=C(N=C(C=2)C=2C=NC(=NC=2)N)N2CCOCC2)S1 IMKNPBUMAAHTIS-UHFFFAOYSA-N 0.000 claims 2
- AMGBXXUJMHVBSM-UHFFFAOYSA-N 5-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]pyrimidin-2-amine Chemical compound CC1=C(CN2CCN(CC2)S(C)(=O)=O)SC2=C(N=C(C=C12)C1=CN=C(N)N=C1)N1CCOCC1 AMGBXXUJMHVBSM-UHFFFAOYSA-N 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- SSZRNGWQSZSKBU-UHFFFAOYSA-N 3-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]aniline Chemical compound CS(=O)(=O)N1CCN(CC1)CC1=CC=2C(=C(N=C(C=2)C=2C=C(N)C=CC=2)N2CCOCC2)S1 SSZRNGWQSZSKBU-UHFFFAOYSA-N 0.000 claims 1
- IIBMYJSHHPAGQC-UHFFFAOYSA-N 3-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]aniline Chemical compound CC1=C(SC2=C(N=C(C=C21)C=1C=C(N)C=CC=1)N1CCOCC1)CN1CCN(CC1)S(=O)(=O)C IIBMYJSHHPAGQC-UHFFFAOYSA-N 0.000 claims 1
- DKDJQHYEAWNROW-UHFFFAOYSA-N 4-(3-methyl-2-piperazin-1-ylthieno[2,3-c]pyridin-7-yl)morpholine Chemical compound N1(CCOCC1)C=1N=CC=C2C=1SC(=C2C)N1CCNCC1 DKDJQHYEAWNROW-UHFFFAOYSA-N 0.000 claims 1
- MMJMBEKLSXKBIG-UHFFFAOYSA-N 4-[5-(1H-indazol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-c]pyridin-7-yl]morpholine Chemical compound N1N=CC2=C(C=CC=C12)C=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2)CN1CCN(CC1)S(=O)(=O)C MMJMBEKLSXKBIG-UHFFFAOYSA-N 0.000 claims 1
- UWSXGUKESNKSQW-UHFFFAOYSA-N 4-[5-(1H-indazol-4-yl)-3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-c]pyridin-7-yl]morpholine Chemical compound N1N=CC2=C(C=CC=C12)C=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2C)CN1CCN(CC1)S(=O)(=O)C UWSXGUKESNKSQW-UHFFFAOYSA-N 0.000 claims 1
- XXZJJUGGOYPFPK-UHFFFAOYSA-N 4-[5-bromo-2-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-c]pyridin-7-yl]morpholine Chemical compound BrC=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2)CN1CCN(CC1)S(=O)(=O)C XXZJJUGGOYPFPK-UHFFFAOYSA-N 0.000 claims 1
- YRNSYSUWAQYNAO-UHFFFAOYSA-N 4-[5-bromo-3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-nitrothieno[2,3-c]pyridin-7-yl]morpholine Chemical compound CC1=C(CN2CCN(CC2)S(C)(=O)=O)SC2=C(N=C(Br)C(=C12)[N+]([O-])=O)N1CCOCC1 YRNSYSUWAQYNAO-UHFFFAOYSA-N 0.000 claims 1
- FDNIYAIHKXIPBV-UHFFFAOYSA-N 4-[5-bromo-3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-c]pyridin-7-yl]morpholine Chemical compound BrC=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2C)CN1CCN(CC1)S(=O)(=O)C FDNIYAIHKXIPBV-UHFFFAOYSA-N 0.000 claims 1
- WKZIPHBTVNBQNF-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-4-amine Chemical compound NC1=NC=C(C=N1)C1=C(C2=C(C(=N1)N1CCOCC1)SC(=C2C)CN1CCN(CC1)S(=O)(=O)C)N WKZIPHBTVNBQNF-UHFFFAOYSA-N 0.000 claims 1
- DLCLCOVJKZCKFE-UHFFFAOYSA-N 5-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-yl-4-nitrothieno[2,3-c]pyridin-5-yl]pyrimidin-2-amine Chemical compound CC1=C(SC2=C(N=C(C(=C21)[N+](=O)[O-])C=1C=NC(=NC=1)N)N1CCOCC1)CN1CCN(CC1)S(=O)(=O)C DLCLCOVJKZCKFE-UHFFFAOYSA-N 0.000 claims 1
- YICCQOVABJYMIB-UHFFFAOYSA-N 5-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-yl-4-nitrothieno[2,3-c]pyridin-5-yl]pyrimidine-2,4-diamine Chemical compound CC1=C(SC2=C(N=C(C(=C21)[N+](=O)[O-])C=1C(=NC(=NC=1)N)N)N1CCOCC1)CN1CCN(CC1)S(=O)(=O)C YICCQOVABJYMIB-UHFFFAOYSA-N 0.000 claims 1
- QKTQFYLQIUZNKS-UHFFFAOYSA-N 5-[4-amino-3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]pyrimidine-2,4-diamine Chemical compound NC1=C2C(=C(N=C1C=1C(=NC(=NC=1)N)N)N1CCOCC1)SC(=C2C)CN1CCN(CC1)S(=O)(=O)C QKTQFYLQIUZNKS-UHFFFAOYSA-N 0.000 claims 1
- ODYRRICDXVGAEO-UHFFFAOYSA-N 5-bromo-3-methyl-7-morpholin-4-ylthieno[2,3-c]pyridine-2-carbaldehyde Chemical compound BrC=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2C)C=O ODYRRICDXVGAEO-UHFFFAOYSA-N 0.000 claims 1
- MOSLIQJOGHBIMD-UHFFFAOYSA-N 5-bromo-7-morpholin-4-ylthieno[2,3-c]pyridine-2-carbaldehyde Chemical compound BrC=1C=C2C(=C(N=1)N1CCOCC1)SC(=C2)C=O MOSLIQJOGHBIMD-UHFFFAOYSA-N 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- IPJDTFRAZJWZMM-UHFFFAOYSA-N [3-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]phenyl]methanol Chemical compound CS(=O)(=O)N1CCN(CC1)CC1=CC=2C(=C(N=C(C=2)C=2C=C(C=CC=2)CO)N2CCOCC2)S1 IPJDTFRAZJWZMM-UHFFFAOYSA-N 0.000 claims 1
- NIBSXRSWNVIYQR-UHFFFAOYSA-N [3-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-ylthieno[2,3-c]pyridin-5-yl]phenyl]methanol Chemical compound CC1=C(CN2CCN(CC2)S(C)(=O)=O)SC2=C(N=C(C=C12)C1=CC=CC(CO)=C1)N1CCOCC1 NIBSXRSWNVIYQR-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (13)
1. Spoj 7-(morfolinil)-2-(N-piperazinil) metil tieno[2, 3-c]piridina formule I ili njegova farmaceutski prihvatljiva sol,
naznačeno time, što:
R1 je H, C1-C6 alkil, C3-C6 cikloalkil, -C(O)R5, -S(O)2R5, -C(O)2R5, C1-C6 alkil supstituiran s R6, C3-C6 supstituiran s R6, aril, aril supstituiran s R6 ili heteroaril supstituiran s R6;
R2, R3 i R4 su svaki zasebno H, -OH, -SH, halo, amino, cijano, -nitro, C1-C6 alkil, C3-C6 cikloalkil, aril, -C(O)R5, -S(O)2R5, -C(O)2R5, -C=C(H)-R6, aminokarbonil supstituiran s R6, alkilamino grupa supstituirana s R6 i opcionalno sadrži C3-C6 cikloalkil, alkilaminokarbonil, heteroaril opcionalno supstituiran s H ili amino, spojeni biciklični ili triciklični heteroaril koji sadrži 1, 2 ili 3 heteroatoma odabrana iz N, O i S, ili aril opcionalno supstituiran s hidroksilom, hidroksialkilom, amino, aminoalkilom, aminokarbinilom, cijano, halogenom, ariloksijem ili R6;
R5 je H, alkil, amino, aril supstituiran s R6, heteroaril supstituiran s R6, spojeni heteroaril supstituiran s R6 ili -trifluorometilom;
R6 je H, hidroksi, halogen, cijano, nitro, amino ili C1-C6 alkil.
2. Spoj prema patentnom zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, pri čemu je spoj:
i) 5-[3-metil-2-[(4-metil sulfonilpiperazin-1-il)metil]-7-morfolinotieno[2,3-c]piridin-5-il]pirimidin-2-amin;
ii) 5-[2-[(4-metilsulfonil piperazin-1-il)metil]-7-morfolino-tieno[2,3-c]piridin-5-il]pirimidin-2-amin;
iii) 4-[5-(1H-indazol-4-il)-2-[(4-metilsulfonil piperazin-1-il)metil]tieno[2,3-c]piridin-7-il] morfolin;
iv) [3-[2-[(4-metilsulfonil piperazin-1-il)metil]-7-morfolino-tieno[2,3-c]piridin-5-il]fenil]metanol;
v) 3-[2-[(4-metilsulfonil piperazin-1-il)metil]-7-morfolino-tieno[2,3-c] piridin-5-il]anilin;
vi) 4-[5-(1H-indazol-4-il)-3-metil-2-[(4-metil sulfonil piperazin-1-il) metil]tieno[2,3-c]piridin-7-il]morfolin;
vii) [3-[3-metil-2-[(4-metil sulfonilpiperazin-1-il)metil]-7-morfolinotieno[2,3-c]piridin-5-il]fenil]metanol;
viii) 3-[3-metil-2-[(4-metil sulfonilpiperazin-1-il)metil]-7-morfolinotieno[2,3-c]piridin-5-il]anilin;
ix) 5-[3-metil-2-[(4-metilsulfonilpiperazin-1-il)metil]-7-morfolino-4-nitrotieno[2,3-c]piridin-5-il]pirimidin-2-amin;
x) 5-(2-amino-pirimidin-5-il)-3-metil-2-[(4-metilsulfonil piperazin-1-il)metil]-7-morfolino-tieno[2,3-c]piridin-4-amin;
xi) 5-[3-metil-2-[(4-metilsulfonilpiperazin-1-il)metil]-7-morfolino-4-nitrotieno[2,3-c]piridin-5-il]pirimidin-2,4-diamin; ili
xii) 5-[4-amino-3-metil-2-[(4-metilsulfonilpiperazin-1-il)metil]-7-morfolinotieno[2,3-c]piridin-5-il]pirimidin-2,4-diamin
3. Spoj prema patentnom zahtjevu 1, pri čemu je spoj 5-[3-metil-2-[(4-metil sulfonilpiperazin-1-il) metil]-7-morfolino-tieno[2,3-c]piridin-5-il]pirimidin-2-amin ili njegova farmaceutski prihvatljiva sol.
4. Spoj prema patentnom zahtjevu 1, koji je 5-[2-[(4-metilsulfonil piperazin-1-il)metil]-7-morfolino-tieno[2,3-c]piridin-5-il]pirimidin-2-amin ili njegova farmaceutski prihvatljiva sol.
5. Spoj prema patentnom zahtjevu 1, koji je spoj spoja formule II
naznačen time, što je X halogen.
6. Spoj prema patentnom zahtjevu 5, pri čemu je spoj:
i) 4-[5-bromo-3-metil-2-[(4metilsulfonilpiperazin-1-il) metil]-4-nitro-tieno[2,3-c]piridin-7-il]morfolin;
ii) 4-[5-bromo-2-[(4-metilsulfonilpiperazin-1-il) metil] tieno [2, 3-c] piridin-7-il] morfolin; ili
iii) 4-[5-bromo-3-metil-2-[(4-metilsullfonilpiperazin-1-il) metil]tieno[2, 3-c] piridin-7-il] morfolin.
7. Spoj formule III,
naznačen time, što:
R2 i R3 su svaki zasebno H, -OH, -SH, halo, amino, cijano, -nitro, C1-C6 alkil, C3-C6 cikloalkil, aril, -C(O)R5, -S(O)2R5, -C(O)2R5, -C=C(H)-R6, aminokarbonil supstituiran s R6, alkilamino grupa supstituirana s R6 i opcionalno sadrži C3-C6 cikloalkil, alkilaminokarbonil, heteroaril opcionalno supstituiran s H ili amino, spojeni biciklični ili triciklični heteroaril koji sadrži 1, 2 ili 3 heteroatoma odabrana iz N, O i S, ili aril opcionalno supstituiran s hidroksilom, hidroksialkilom, amino, aminoalkilom, aminokarbinilom, cijano, halogenom, ariloksijem ili R6;
a X je halogen.
8. Spoj prema patentnom zahtjevu 7, pri čemu je spoj:
i) 5-bromo-3-metil-7-moefolino-4-nitro-tieno[2,3-c]piridin-2-karbaldehid;
ii) 5-bromo-3-metil-7-morfolino-tieno[2,3-c]piridin-2-karbaldehid; ili
iii) 5-bromo-7-morfolino-tieno [2, 3-c] piridin-2-karbaldehid.
9. Farmaceutski pripravak koji sadrži:
a) terapijski djelotvornu količinu spoja kako je definirano prema patentnom zahtjevu 1 ili patentnom zahtjevu 2 ili njegovu farmaceutski prihvatljivu sol; i
b) farmaceutski prihvatljivi nosač, razrjeđivač ili neaktivni nosač.
10. Spoj definiran prema bilo kojem patentnom zahtjevu od 1 do 4 ili njegova farmaceutski prihvatljiva sol za primjenu u liječenu čovjeka ili životinje.
11. Spoj definiran prema bilo kojem patentnom zahtjevu od 1 do 4 ili njegova farmaceutski prihvatljiva sol za primjenu u liječenju raka.
12. Spoj za primjenu prema patentnom zahtjevu 11, naznačen time, što je rak rak pluća, rak gušterače, rak prostate, rak dojke, rak mozga ili rak jajnika.
13. Spoj za primjenu prema bilo kojem patentnom zahtjevu 11 i 12, naznačen time, što se liječenje raka sastoji od oralne, parenteralne ili rektalne primjene djelotvorne antitumorske količine spoja ili njegove farmaceutski prihvatljive soli kod čovjeka.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP14841337.0A EP3230289B1 (en) | 2014-12-11 | 2014-12-11 | 7-(morpholinyl)-2-(n-piperazinyl) methyl thieno [2, 3-c]pyridine derivatives as anticancer drugs |
PCT/IN2014/000770 WO2016092556A1 (en) | 2014-12-11 | 2014-12-11 | 7-(morpholinyl)-2-(n-piperazinyl) methyl thieno [2, 3-c] pyridine derivatives as anticancer drugs |
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HRP20192041T1 true HRP20192041T1 (hr) | 2020-02-07 |
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HRP20192041TT HRP20192041T1 (hr) | 2014-12-11 | 2019-11-12 | [derivati 7-(morfolinil)-2-(n-piperazinil) metil tieno [2, 3-c]piridina kao lijekovi protiv raka] |
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US (1) | US10106554B2 (hr) |
EP (1) | EP3230289B1 (hr) |
JP (1) | JP6454419B2 (hr) |
KR (1) | KR102328921B1 (hr) |
CN (1) | CN107074873B (hr) |
AP (1) | AP2017009749A0 (hr) |
AU (1) | AU2014413483B2 (hr) |
BR (1) | BR112017005518B1 (hr) |
CA (1) | CA2959980C (hr) |
CO (1) | CO2017002266A2 (hr) |
CY (1) | CY1122080T1 (hr) |
DK (1) | DK3230289T3 (hr) |
EA (1) | EA036819B1 (hr) |
ES (1) | ES2750268T3 (hr) |
HR (1) | HRP20192041T1 (hr) |
HU (1) | HUE047144T2 (hr) |
IL (1) | IL252254B (hr) |
LT (1) | LT3230289T (hr) |
MA (1) | MA40110B2 (hr) |
MX (1) | MX2017004782A (hr) |
MY (1) | MY188946A (hr) |
NZ (1) | NZ729078A (hr) |
PH (1) | PH12017500342A1 (hr) |
PL (1) | PL3230289T3 (hr) |
PT (1) | PT3230289T (hr) |
RS (1) | RS59409B1 (hr) |
SG (1) | SG11201702162PA (hr) |
SI (1) | SI3230289T1 (hr) |
UA (1) | UA117318C2 (hr) |
WO (1) | WO2016092556A1 (hr) |
ZA (1) | ZA201701036B (hr) |
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MX2022004390A (es) * | 2019-10-11 | 2022-08-08 | Incyte Corp | Aminas biciclicas como inhibidores de la cinasa dependiente de ciclina 2 (cdk2). |
CN115103840A (zh) | 2019-12-20 | 2022-09-23 | 拜耳公司 | 取代的噻吩甲酰胺、噻吩甲酸及其衍生物 |
JP2024517127A (ja) * | 2021-04-21 | 2024-04-19 | ナトコ ファーマ リミテッド | 7-(モルホリニル)-2-(N-ピペラジニル)メチルチエノ[2,3-c]ピリジン誘導体の調製のための改良プロセス |
US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US3579526A (en) | 1968-11-13 | 1971-05-18 | Research Corp | Preparation of thienopyridines |
FR2411838A1 (fr) | 1977-12-19 | 1979-07-13 | Parcor | Nouveaux derives des thieno (2-3-c) et (3,2-c) pyridines, leurs procede de preparation et leur application therapeutique |
US4839365A (en) | 1987-05-19 | 1989-06-13 | Shinogi & Co., Ltd. | Thienopyridine derivatives useful in treating gastric ulcers |
US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
EP1181296A1 (en) | 1999-06-03 | 2002-02-27 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
US20060074102A1 (en) | 2004-05-14 | 2006-04-06 | Kevin Cusack | Kinase inhibitors as therapeutic agents |
KR20090021155A (ko) * | 2006-04-26 | 2009-02-27 | 에프. 호프만-라 로슈 아게 | Pi3k 억제제로서의 피리미딘 유도체 |
GB0608264D0 (en) * | 2006-04-26 | 2006-06-07 | Piramed Ltd | Pharmaceutical compounds |
US8247397B2 (en) * | 2007-09-12 | 2012-08-21 | Genentech, Inc. | Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use |
GB0723748D0 (en) | 2007-12-04 | 2008-01-16 | Ucb Pharma Sa | Therapeutic agents |
KR101626996B1 (ko) | 2008-03-31 | 2016-06-02 | 제넨테크, 인크. | 벤조피란 및 벤족세핀 pi3k 저해제 화합물 및 이의 사용 방법 |
EA024252B1 (ru) * | 2009-01-08 | 2016-08-31 | Кьюрис, Инк. | Ингибиторы фосфоинозитид-3-киназ с цинксвязывающей группой |
US8569296B2 (en) * | 2009-09-29 | 2013-10-29 | Xcovery Holding Company, Llc | PI3K (delta) selective inhibitors |
EP2526102B1 (en) | 2010-01-22 | 2017-03-08 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | Inhibitors of PI3 kinase |
CA2825028A1 (en) * | 2011-02-09 | 2012-08-16 | F. Hoffman-La Roche Ag | Heterocyclic compounds as pi3 kinase inhibitors |
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