HRP20110473T1 - Supstituirani derivati 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril 1-h-pirola kao inhibitori kiselinske sekrecije - Google Patents
Supstituirani derivati 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril 1-h-pirola kao inhibitori kiselinske sekrecije Download PDFInfo
- Publication number
- HRP20110473T1 HRP20110473T1 HR20110473T HRP20110473T HRP20110473T1 HR P20110473 T1 HRP20110473 T1 HR P20110473T1 HR 20110473 T HR20110473 T HR 20110473T HR P20110473 T HRP20110473 T HR P20110473T HR P20110473 T1 HRP20110473 T1 HR P20110473T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- optionally
- mono
- atoms
- alkyl
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract 6
- 239000003112 inhibitor Substances 0.000 title claims 4
- 230000009858 acid secretion Effects 0.000 title claims 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 58
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 23
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract 22
- 125000001769 aryl amino group Chemical group 0.000 claims abstract 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 20
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 20
- 125000005842 heteroatom Chemical group 0.000 claims abstract 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 19
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims abstract 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 17
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 16
- 125000001424 substituent group Chemical group 0.000 claims abstract 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 14
- -1 thiocarbamoyl Chemical group 0.000 claims abstract 14
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 12
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims abstract 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 11
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 10
- 125000003277 amino group Chemical group 0.000 claims abstract 10
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract 10
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims abstract 10
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract 10
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims abstract 10
- 125000005110 aryl thio group Chemical group 0.000 claims abstract 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 9
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims abstract 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 9
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims abstract 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims abstract 7
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims abstract 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical group 0.000 claims 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 14
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 13
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 6
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 208000008469 Peptic Ulcer Diseases 0.000 claims 4
- 230000002496 gastric effect Effects 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 208000011906 peptic ulcer disease Diseases 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 206010063655 Erosive oesophagitis Diseases 0.000 claims 2
- 208000007882 Gastritis Diseases 0.000 claims 2
- 206010017866 Gastritis haemorrhagic Diseases 0.000 claims 2
- 206010020601 Hyperchlorhydria Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 206010042220 Stress ulcer Diseases 0.000 claims 2
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 230000037328 acute stress Effects 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 208000000718 duodenal ulcer Diseases 0.000 claims 2
- 201000006549 dyspepsia Diseases 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 208000017215 gastric mucosa-associated lymphoid tissue lymphoma Diseases 0.000 claims 2
- 201000000052 gastrinoma Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000000689 peptic esophagitis Diseases 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 230000035882 stress Effects 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- GKYNXSVMESZZIF-UHFFFAOYSA-N 1-(4-fluoro-5-phenyl-1-pyridin-3-ylsulfonylpyrrol-3-yl)-n-methylmethanamine Chemical group FC=1C(CNC)=CN(S(=O)(=O)C=2C=NC=CC=2)C=1C1=CC=CC=C1 GKYNXSVMESZZIF-UHFFFAOYSA-N 0.000 claims 1
- GLTCPTOZHSIXQA-UHFFFAOYSA-N 1-[5-(2-fluorophenyl)-1-(6-methylpyridin-3-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical group C=1C=C(C)N=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1F GLTCPTOZHSIXQA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SRTTWNYIEACZDL-UHFFFAOYSA-N n-methyl-1-[5-(2-methylphenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]methanamine Chemical group C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1C SRTTWNYIEACZDL-UHFFFAOYSA-N 0.000 claims 1
- RXQZPPFNPSUVQJ-UHFFFAOYSA-N n-methyl-1-[5-(4-methylthiophen-3-yl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]methanamine Chemical group C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CSC=C1C RXQZPPFNPSUVQJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- BFDBKMOZYNOTPK-UHFFFAOYSA-N vonoprazan Chemical group C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1F BFDBKMOZYNOTPK-UHFFFAOYSA-N 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/12—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 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
Abstract
Spoj predstavljen formulom (I): ,naznačen time, da R1 je aromatska ili zasićena ili nezasićena nearomatska monociklička heterociklička skupina koja sadrži dušik, te sadrži atom kao sastavni dio prstena, barem jedan dušikov atom i opcijski je kondenzirana sa benzenskim prstenom ili aromatskim ili nearomatskim heterociklom, dok je monociklička heterociklička skupina koja sadrži dušik opcijski kondenzirana s benzenskim prstenom ili heterociklom koji opcijski ima 1 to 5 supstituenata odabranih iz skupine koja sadrži (1) atom halogena, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14ariloksi, (7) C7-16aralkiloksi, (8) merkapto, (9) C1-5alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6alkil-karbonil, (21) C6-14aril-karbonil, (22) karboksil, (23) C1-6alkoksi-karbonil, (24) C6-14ariloksikarbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-5 alkoksi-karbonilamino, (38) C1-5 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 arilkarbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim jednog dušikovog atoma i atom ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atom kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi, R2 je (i) C6-14 aril skupina koja opcijski ima 1 do 5 supstituenata odabranih iz skupine koja se sastoji od (1) halogen atoma, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ar
Claims (20)
1. Spoj predstavljen formulom (I):
[image]
,
naznačen time, da
R1je aromatska ili zasićena ili nezasićena nearomatska monociklička heterociklička skupina koja sadrži dušik, te sadrži atom kao sastavni dio prstena, barem jedan dušikov atom i opcijski je kondenzirana sa benzenskim prstenom ili aromatskim ili nearomatskim heterociklom, dok je monociklička heterociklička skupina koja sadrži dušik opcijski kondenzirana s benzenskim prstenom ili heterociklom koji opcijski ima 1 to 5 supstituenata odabranih iz skupine koja sadrži (1) atom halogena, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14ariloksi, (7) C7-16aralkiloksi, (8) merkapto, (9) C1-5alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6alkil-karbonil, (21) C6-14aril-karbonil, (22) karboksil, (23) C1-6alkoksi-karbonil, (24) C6-14ariloksikarbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-5 alkoksi-karbonilamino, (38) C1-5 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 arilkarbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim jednog dušikovog atoma i atom ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atom kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi,
R2je
(i) C6-14 aril skupina koja opcijski ima 1 do 5 supstituenata odabranih iz skupine koja se sastoji od (1) halogen atoma, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkilkarbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi,
(ii) tienil skupina koja opcijski ima 1 do 4 supstituenata odabrana iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 to 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) monoC1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do10-člana aromatska heterociklička skupina koja sadrži osim atoma ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi, ili
(iii) piridil skupina koja opcijski ima 1 do 4 supstituenta odabrana iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14ariloksi, (7) C7-16aralkiloksi, (8) merkapto, (9) C1-6alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6alkil-karbonil, (21) C6-14aril-karbonil, (22) karboksil, (23) C1-6alkoksi-karbonil, (24)C6-14ariloksikarbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim atoma dušika i atom ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži osim atoma ugljika, 1 ili 2 vrste 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atom kisika, (48) C1-3 alkilendioksi, (49) C3-7cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi,
R3 i R4 su svaki atom vodika, ili jedan od R3 i R4 je atom vodika a drugi je
(i) C1-4 alkil skupina koja opcijski ima 1 do 3 supstituenta odabranih iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži osim atoma ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3 alkilendioksi, i (49) C3-7 cikloalkil,
(ii) acil skupina odabrana iz skupine koju sačinjavaju C1-7 alkanoil skupina, C6-14 aril-karbonil skupina, C1-6 alkoksi-karbonil skupina, C6-14 ariloksi-karbonil skupina, C7-19 aralkil-karbonil skupina, C7-19 aralkiloksi-karbonil skupina, 5-ili 6-člana heterociklo-karbonil skupina ili njezina kondenzirana heterociklo-karbonil skupina, i 5-ili 6-člana heterociklo-acetil skupina, pri čemu kada acil skupina je C1-7 alkanoil skupina ili C1-6 alkoksi-karbonil skupina, acil skupina je opcijski supstituirana sa 1 do 3 C1-4 alkiltio skupina, halogenom, C1-6 alkoksi skupinama, nitro skupinom, C1-6 alkoksi-karbonil skupinama, mono-ili di-C1-6 alkilamino skupinama, C1-6 alkoksiimino skupinama ili hidroksiiminom, dok je acil skupina C6-14 aril-karbonil skupina, C6-14 ariloksi-karbonil skupina, C7-19 aralkil-karbonil skupina, C7-19 aralkiloksikarbonil skupina, 5-ili 6-člana heterociklo-karbonil skupina ili 5-ili 6-člana heterociklo-acetil skupina, tada acil skupina je opcijski supstituirana sa 1 do 5-članim C1-6 alkil skupinama, C3-6 cikloalkil skupinama, C2-6 alkenil skupinama, C2-6 alkinil skupinama, C1-6 alkoksi skupinama, C1-7 alkanoil skupinama, C6-14 aril-karbonil skupinama, C1-6 alkoksi-karbonil skupinama, C6-14 ariloksi-karbonil skupinama, C7-19 aralkil-karbonil skupinama, C7-19 aralkiloksi-karbonil skupinama, nitro, amino, hidroksi, cijano, sulfamoil, merkapto, halogen, ili C1-4 alkiltio skupinama,
(iii) halogen atom, (iv) cijano skupina ili (v) nitro skupina,i
R5 je C1-6 alkil skupina,
ili njegova sol.
2. Spoj prema zahtjevu 1 i predstavljen formulom (I):
[image]
gdje
R1je monociklička koja sadrži dušik heterociklička skupina opcijski kondenzirana sa benzenskim prstenom ili heterociklom, monociklička koja sadrži dušik heterociklička skupina opcijski je kondenzirana s benzenskim prstenom ili heterociklom koji opcijski ima 1 do 5 supstituenata odabranih iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6alkil-karbamoil, (28) di-C1-6alkil-karbamoil, (29) C6-14aril-karbamoil, (30) C1-6alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži, osim jednog atoma dušika atom i atom ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atom kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3alkilendioksi, (49) C3-7cikloalkil, (50) C1-6alkil skupina opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi,
R2je
(i) C6-14 aril skupina koja opcijski ima 1 do 5 supstituenata odabranih iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14ariltio, (11) C7-16aralkiltio, (12) amino, (13) mono-C1-6alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) diC1-6alkil-karbamoil, (29) C6-14aril-karbamoil, (30) C1-6alkilsulfonil, (31) C6-14arilsulfonil, (32) C1-6alkilsulfinil, (33) C6-1 4 arilsulfinil, (34) formilamino, (35) C1-6 alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksi-karbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karboniloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-car-bamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži, osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6alkinil skupina, (53) C1-6alkil skupina supstituirana sa 1 do 3 hidroksi, ili
(ii) tienil skupina koja opcijski ima 1 do 4 supstituenta odabranih iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6 alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-6 alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6alkil-karbamoil, (28) di-C1-6alkil-karbamoil, (29) C6-14aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6alkil-karbonilamino, (36) C6-14aril-karbonilamino, (37) C1-6alkoksi-karbonilamino, (38) C1-6alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6 alkoksi-karbo-iloksi, (43) mono-C1-6 alkil-karbamoiloksi, (44) di-C1-6 alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži, osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10 člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (48) C1-3 alkilendioksi, (49) C3-7 cikloalkil, (50) C1-6 alkil skupina koja opcijski ima 1 do 3 halogen atoma, (51) C2-6 alkenil skupina koja opcijski ima 1 do 3 halogen atoma, (52) C2-6 alkinil skupina, i (53) C1-6 alkil skupina supstituirana sa 1 do 3 hidroksi,
R3 i R4su svaki vodikov atom, ili jedan od R3 i R4 je vodikov atom a drugi je
(i) C1-4alkil skupina koja opcijski ima 1 do 3 supstituenata odabranih iz skupine koja sadrži (1) halogen atom, (2) nitro, (3) cijano, (4) hidroksi, (5) C1-6alkoksi koji opcijski ima 1 do 3 halogen atoma, (6) C6-14 ariloksi, (7) C7-16 aralkiloksi, (8) merkapto, (9) C1-6 alkiltio koji opcijski ima 1 do 3 halogen atoma, (10) C6-14 ariltio, (11) C7-16 aralkiltio, (12) amino, (13) mono-C1-6 alkilamino, (14) mono-C6-14 arilamino, (15) mono-C7-16 aralkilamino, (16) di-C1-6 alkilamino, (17) di-C6-14 arilamino, (18) di-C7-16 aralkilamino, (19) formil, (20) C1-5alkil-karbonil, (21) C6-14 aril-karbonil, (22) karboksil, (23) C1-6 alkoksi-karbonil, (24) C6-14 ariloksi-karbonil, (25) karbamoil, (26) tiokarbamoil, (27) mono-C1-6 alkil-karbamoil, (28) di-C1-6 alkil-karbamoil, (29) C6-14 aril-karbamoil, (30) C1-6 alkilsulfonil, (31) C6-14 arilsulfonil, (32) C1-6 alkilsulfinil, (33) C6-14 arilsulfinil, (34) formilamino, (35) C1-6alkil-karbonilamino, (36) C6-14 aril-karbonilamino, (37) C1-6 alkoksikarbonilamino, (38) C1-6 alkilsulfonilamino, (39) C6-14 arilsulfonilamino, (40) C1-6 alkil-karboniloksi, (41) C6-14 aril-karboniloksi, (42) C1-6alkoksi-karboniloksi, (43) mono-C1-6alkil-karbamoiloksi, (44) di-C1-6alkil-karbamoiloksi, (45) C6-14 aril-karbamoiloksi, (46) 5-do 7-člana zasićena ciklička amino skupina koja opcijski sadrži, osim jednog atoma dušika i atom ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atoma sumpora i atoma kisika, (47) 5-do 10-člana aromatska heterociklička skupina koja sadrži, osim atoma ugljika, 1 ili 2 vrste od 1 do 4 heteroatoma odabranih od atoma dušika, atom sumpora i atom kisika, (48) C1-3 alkilen-5-dioksi, i (49) C3-7 cikloalkil,
(ii) acil skupina odabrana iz skupine koja sadrži C1-7alkanoil skupinu, C6-14 aril-karbonil skupinu, C1-6 alkoksi-karbonil skupinu, C6-14 ariloksi-karbonil skupinu, C7-19 aralkil-karbonil skupinu, C7-19aralkiloksi-karbonil skupinu, 5- ili 6-članu heterociklo-karbonil skupinu ili njezinu kondenziranu heterociklo-karbonil skupinu, i 5-ili 6-članu heterociklo-acetil skupinu, pri čemu kada acil skupina je C1-7 alkanoil skupina ili C1-6 alkoksi-karbonil skupina, tada acil skupina je opcijski supstituirana sa 1 do 3 C1-4 alkiltio skupinama, halogenom, C1-6alkoksi skupinama, nitro skupinom, C1-6alkoksi-karbonil skupinama, mono- ili di-C1-6alkilamino skupinama, C1-6 alkoksiimino skupinama ili hidroksiiminom, gdje kada acil skupina je C6-14 aril-karbonil skupina, C6-14 ariloksi-karbonil skupina, C7-19 aralkil-karbonil skupina, C7-19 aralkiloksikarbonil skupina, 5-ili 6-člana heterociklo-karbonil skupina ili 5-ili 6-člana heterociklo-acetil skupina, tada acil skupina je opcijski supstituirana sa 1 do 5 C1-6 alkil skupinama, C3-6 cikloalkil skupinama, C2-6 alkenil skupinama, C2-6 alkinil skupinama, C1-6 alkoksi skupinama, C1-7 alkanoil skupinama, C6-14 aril-karbonil skupinama, C1-6 alkoksi-karbonil skupinama, C6-14 ariloksi-karbonil skupinama, C7-19 aralkil-karbonil skupinama, C7-19 aralkiloksi-karbonil skupinama, nitro, amino, hidroksi, cijano, sulfamoil, merkapto, halogen, ili C1-4 alkiltio skupinama,
(iii) halogen atom, (iv) cijano skupina ili (v) nitro skupina, i
R5je C1-6 alkil skupina,
ili njegova sol.
3. Spoj prema zahtjevu 1 ili 2, naznačen time, da R1 je monociklička koja sadrži dušik heterociklička skupina.
4. Spoj prema zahtjevu 1 ili 2, naznačen time, da monociklička koja sadrži dušik heterociklička skupina je piridil skupina.
5. Spoj prema zahtjevu 1 ili 2, naznačen time, da R2 je fenilna skupina opcijski supstituirana sa 1 do 5 supstituenata odabranih od (i) halogen atoma i (ii) C1-6 alkila opcijski supstituiranog sa 1 do 3 halogen atoma.
6. Spoj prema zahtjevu 1, naznačen time, da R2 je piridilna skupina opcijski supstituirana sa 1 do 4 supstituenata odabranih od C1-6 alkila, halogen atoma, C1-6 alkoksi, cijano, acil, nitro i amino.
7. Spoj prema zahtjevu 1 ili 2, naznačen time, da R3 i R4 su svaki atom vodika.
8. Spoj prema zahtjevu 1 ili 2, naznačen time, da R5 je metilna skupina.
9. Spoj prema zahtjevu 1 predstavljen formulom (I):
[image]
naznačen time, da R1 je piridilna skupina opcijski supstituirana sa 1 do 3 supstituenata odabranih od (i) C1-6 alkil opcijski supstituiran sa 1 do 3 halogen atoma i (ii) C1-6 alkoksi opcijski supstituiran sa 1 do 3 halogen atoma, R2 je fenilna skupina opcijski supstituirana sa 1 do 5 supstituenata odabranih od (i) halogen atoma i (ii) C1-6alkila opcijski supstituiranih sa 1 do 3 halogen atoma, R3 i R4 su svaki atom vodika, i R5 je metil.
10. Spoj prema zahtjevu 1, naznačen time, da je to 1-{5-(2-fluorofenil)-1-[(6-metilpiridin-3-il)sulfonil]-1H-pirol-3-il}-N-metilmetanamin ili njegova sol.
11. Spoj prema zahtjevu 1, naznačen time, da je to 1-[4-fluoro-5-fenil-1-(piridin-3-ilsulfonil)-1H-pirol-3-il]-N-metilmetanamin ili njegova sol.
12. Spoj prema zahtjevu 1, naznačen time, da je to N-metil-1-[5-(4-metil-3-tienil)-1-(piridin-3-ilsulfonil)-1H-pirol-3-il]metanamin ili njegova sol.
13. Spoj prema zahtjevu 1, naznačen time, da je to 1-[5-(2-fluoropiridin-3-il)-1-(piridin-3-ilsulfonil)-1H-pirol-3-il]-N-5 metilmetanamin ili njegova sol.
14. Spoj prema zahtjevu 1, naznačen time, da je to 1-[5-(2-fluorofenil)-1-(piridin-3-ilsulfonil)-1H-pirol-3-il]-N-metilmetanamin ili njegova sol.
15. Spoj prema zahtjevu 1, naznačen time, da je to N-metil-1-[5-(2-metilfenil)-1-(piridin-3-ilsulfonil)-1H-pirol-3-il]metanamin ili njegova sol.
16. Farmaceutski sastav, naznačen time, da sadrži spoj prema zahtjevu 1 ili 2.
17. Farmaceutski sastav prema zahtjevu 16, naznačen time, da je to inhibitor kiselinske sekrecije.
18. Farmaceutski sastav prema zahtjevu 16, naznačen time, da je to blokator kiseline kao konkurent kaliju.
19. Farmaceutski sastav prema zahtjevu 16, naznačen time, da je to sredstvo za liječenje ili profilaksu peptičkog čira, sindroma Zollinger-Ellison, gastritisa, erozivnog ezofagitisa, refluks-ezofagitisa, simptomatične gastroezofagijalne refluks bolesti (simptomatični GERD), funkcionalne dispepsije, gastričnog raka, gastričnog-MALT-limfoma ili gastrične hiperkiselosti; ili je inhibitor gornje gastrointestinalne hemoralgije uzrokovane peptičkim čirom, akutnim stresom ulkusa, akutnim hemoralgičnim gastritisom ili invazivnim stresom.
20. Uporaba spoja prema zahtjevu 1 ili 2, naznačena time, da je za proizvodnju farmaceutskog sastava za liječenje ili profilaksu peptičkog čira, sindroma Zollinger-Ellison, gastritisa, erozivnog ezofagitisa, refluks-ezofagitisa, simptomatične gastroezofagijalne refluks bolesti (simptomatični GERD), funkcionalne dispepsije, gastričnog raka, gastričnog-MALT-limfoma ili gastrične hiperkiselosti; ili kao inhibitora gornje gastrointestinalne hemoralgije uzrokovane peptičkim čirom, akutnim stresom ulkusa, akutnim hemoralgičnim gastritisom ili invazivnim stresom.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005250356 | 2005-08-30 | ||
JP2006100626 | 2006-03-31 | ||
PCT/JP2006/317408 WO2007026916A1 (en) | 2005-08-30 | 2006-08-29 | 1-heterocyclylsulfonyl, 2-aminomethyl, 5- (hetero-) aryl substituted 1-h-pyrrole derivatives as acid secretion inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20110473T1 true HRP20110473T1 (hr) | 2011-07-31 |
Family
ID=37517870
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20110473T HRP20110473T1 (hr) | 2005-08-30 | 2011-06-27 | Supstituirani derivati 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril 1-h-pirola kao inhibitori kiselinske sekrecije |
HRP20120792TT HRP20120792T1 (hr) | 2005-08-30 | 2012-10-03 | 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril supstituirani 1-h-pirol derivati kao inhibitori sekrecije želuäśanje kiseline |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20120792TT HRP20120792T1 (hr) | 2005-08-30 | 2012-10-03 | 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril supstituirani 1-h-pirol derivati kao inhibitori sekrecije želuäśanje kiseline |
Country Status (33)
Country | Link |
---|---|
US (7) | US7498337B2 (hr) |
EP (2) | EP1919865B1 (hr) |
JP (3) | JP4035559B1 (hr) |
KR (2) | KR101408561B1 (hr) |
CN (1) | CN101300229B (hr) |
AR (1) | AR055144A1 (hr) |
AT (1) | ATE504567T1 (hr) |
AU (1) | AU2006285641A1 (hr) |
BR (2) | BRPI0615111B8 (hr) |
CA (1) | CA2621182C (hr) |
CR (1) | CR9755A (hr) |
CY (2) | CY1111922T1 (hr) |
DE (1) | DE602006021195D1 (hr) |
DK (2) | DK1919865T3 (hr) |
ES (2) | ES2364498T3 (hr) |
GE (1) | GEP20105044B (hr) |
HK (2) | HK1118547A1 (hr) |
HR (2) | HRP20110473T1 (hr) |
IL (1) | IL189375A (hr) |
JO (1) | JO2791B1 (hr) |
MA (1) | MA29773B1 (hr) |
ME (1) | ME00610B (hr) |
NO (1) | NO341894B1 (hr) |
NZ (1) | NZ566378A (hr) |
PE (2) | PE20110009A1 (hr) |
PL (2) | PL2327692T3 (hr) |
PT (2) | PT2327692E (hr) |
RS (2) | RS52473B9 (hr) |
SI (2) | SI1919865T1 (hr) |
TW (1) | TWI358296B (hr) |
UA (1) | UA94424C2 (hr) |
WO (1) | WO2007026916A1 (hr) |
ZA (1) | ZA200802488B (hr) |
Families Citing this family (98)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RS52473B9 (sr) * | 2005-08-30 | 2019-07-31 | Takeda Pharmaceuticals Co | 1-heterociklilsulfonil, 2-aminometil, 5-(hetero-)aril supstituisani derivati 1-h-pirola kao inhibitori sekrecije kiseline |
US8933105B2 (en) * | 2007-02-28 | 2015-01-13 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
KR101559597B1 (ko) | 2007-09-28 | 2015-10-12 | 다케다 야쿠힌 고교 가부시키가이샤 | 5―원 헤테로시클릭 화합물 |
KR101558011B1 (ko) * | 2007-09-28 | 2015-10-06 | 다케다 야쿠힌 고교 가부시키가이샤 | 양성자 펌프 억제제로서의 5-원 이종원자고리 화합물 |
JP5450083B2 (ja) | 2007-11-01 | 2014-03-26 | 武田薬品工業株式会社 | 複素環化合物 |
US9186411B2 (en) * | 2008-07-28 | 2015-11-17 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition |
WO2010021149A1 (ja) * | 2008-08-21 | 2010-02-25 | 武田薬品工業株式会社 | 酸分泌抑制スピロ化合物 |
AR073136A1 (es) | 2008-08-27 | 2010-10-13 | Takeda Pharmaceutical | Compuestos de pirrol |
ES2609980T3 (es) * | 2009-02-25 | 2017-04-25 | Takeda Pharmaceutical Company Limited | Procedimiento para producir compuesto de pirrol |
CA2756086A1 (en) | 2009-03-26 | 2010-09-30 | Takeda Pharmaceutical Company Limited | Pyrazole compound |
WO2011004882A1 (ja) | 2009-07-09 | 2011-01-13 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
WO2012095691A1 (en) * | 2011-01-15 | 2012-07-19 | Jubilant Life Sciences Ltd. | An improved process for producing aminopyridines |
CN102863371B (zh) * | 2011-07-06 | 2016-04-13 | 中国科学院上海有机化学研究所 | 氟代二氢吡咯或氟代吡咯 |
NZ703528A (en) * | 2012-06-27 | 2016-08-26 | Takeda Pharmaceutical | Liquid preparations of amines and organic acids stabilized by salts |
WO2014019442A1 (zh) * | 2012-08-03 | 2014-02-06 | 上海恒瑞医药有限公司 | 苯并呋喃类衍生物、其制备方法及其在医药上的应用 |
RU2015122126A (ru) * | 2012-11-19 | 2017-01-10 | Цзянсу Хэнсох Фармасьютикал Ко., Лтд. | Производное пиррол сульфонамида, метод его получения и применение в медицине |
EP2963019B1 (en) | 2013-02-28 | 2020-08-12 | Takeda Pharmaceutical Company Limited | Method for producing pyridine-3-sulfonyl chloride |
KR102084185B1 (ko) * | 2013-08-29 | 2020-03-04 | 주식회사 대웅제약 | 테트라히드로사이클로펜타피롤 유도체 및 이의 제조방법 |
KR102129842B1 (ko) | 2013-10-02 | 2020-07-06 | 주식회사 대웅제약 | 술포닐인돌 유도체 및 이의 제조방법 |
CN103951652B (zh) * | 2014-04-18 | 2015-09-23 | 潍坊博创国际生物医药研究院 | 5-(2-氟苯基)-n-甲基-1-(3-吡啶基磺酰基)-1h-吡咯-3-甲胺水溶性有机酸盐和注射剂及它们的制备方法 |
CN105367550A (zh) * | 2014-08-11 | 2016-03-02 | 江苏柯菲平医药股份有限公司 | 四氢环戊二烯并[c]吡咯类衍生物、其制备方法及其在医药上的应用 |
CN105646451A (zh) * | 2014-11-12 | 2016-06-08 | 江苏豪森药业集团有限公司 | 钾离子竞争性酸阻滞剂的晶型及其制备方法 |
CN104447491B (zh) * | 2014-11-19 | 2017-06-23 | 连云港恒运医药有限公司 | 含吡咯环质子泵抑制剂的半富马酸盐及其中间体和医药用途 |
CN104447490B (zh) * | 2014-11-19 | 2017-06-06 | 连云港恒运医药有限公司 | 一种质子泵抑制剂的晶型、制备中间体及其合成方法和医药用途 |
WO2016078594A1 (zh) * | 2014-11-19 | 2016-05-26 | 江苏豪森药业集团有限公司 | 含吡咯环质子泵抑制剂的半富马酸盐及其晶型、中间体和医药用途 |
CN105693693A (zh) * | 2014-11-27 | 2016-06-22 | 江苏柯菲平医药股份有限公司 | 一种吡咯类胃酸分泌和抑制剂化合物盐的制备 |
CN104356043B (zh) * | 2014-11-27 | 2016-10-26 | 重庆威尔德浩瑞医药化工有限公司 | 一种制备5-(2-氟苯基)-1h-吡咯-3-甲醛的方法 |
CN105708812A (zh) * | 2014-12-02 | 2016-06-29 | 江苏柯菲平医药股份有限公司 | 一种5-(2-氟苯基)-n-甲基-1-(3-吡啶基磺酰基)-1h-吡咯-3-甲氨冻干粉针及其制备方法 |
CN104860923B (zh) * | 2015-01-21 | 2018-01-12 | 山东康美乐医药科技有限公司 | 富马酸沃诺拉赞的制备方法 |
CN105985278A (zh) * | 2015-01-27 | 2016-10-05 | 江苏柯菲平医药股份有限公司 | 吡咯磺酰类衍生物、其制备方法及其在医药上的应用 |
CN105982867A (zh) * | 2015-02-27 | 2016-10-05 | 江苏柯菲平医药股份有限公司 | 一种h009冻干粉针及其制备方法 |
CN106031710B (zh) * | 2015-03-16 | 2019-03-12 | 南京优科制药有限公司 | 一种富马酸氟呐普拉赞的注射剂及其制备方法 |
CN104814964B (zh) * | 2015-04-16 | 2018-07-31 | 广东赛烽医药科技有限公司 | 一种抗胃幽门螺旋杆菌的药物组合物、制备方法及其应用 |
KR101613245B1 (ko) | 2015-04-27 | 2016-04-18 | 주식회사 대웅제약 | 신규의 4-메톡시 피롤 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
CN105315258A (zh) * | 2015-05-16 | 2016-02-10 | 南京海纳医药科技有限公司 | 富马酸沃诺拉赞多晶型及其制备方法 |
CN104860926B (zh) * | 2015-06-10 | 2017-06-30 | 浙江诚意药业股份有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN104945313A (zh) * | 2015-06-19 | 2015-09-30 | 洪帅金 | 一种2-甲基-3-溴吡啶的制备方法 |
CN104926790B (zh) * | 2015-06-29 | 2017-07-07 | 江苏奥赛康药业股份有限公司 | 一种高纯度Vonoprazan Fumarate化合物及其中间体、杂质以及它们的制备方法 |
MY184283A (en) | 2015-06-30 | 2021-03-30 | Takeda Pharmaceuticals Co | Method for producing pyrrole compound |
CN104974082A (zh) * | 2015-07-26 | 2015-10-14 | 陈吉美 | 一种2-甲基-4-溴吡啶的制备方法 |
CN106432191A (zh) * | 2015-08-10 | 2017-02-22 | 陕西合成药业股份有限公司 | 一种新的吡咯类衍生物、其制备方法及其在医药上的应用 |
CN105106203B (zh) * | 2015-08-17 | 2019-04-05 | 江苏豪森药业集团有限公司 | 富马酸沃诺拉赞的药物组合物及其制备方法 |
CN105085484B (zh) * | 2015-08-21 | 2017-11-24 | 南京济群医药科技股份有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN105030725B (zh) * | 2015-08-26 | 2019-12-10 | 迪沙药业集团有限公司 | 一种富马酸沃诺拉赞肠溶组合物及其制备方法 |
CN105030720B (zh) * | 2015-08-26 | 2019-12-10 | 迪沙药业集团有限公司 | 一种富马酸沃诺拉赞肠溶片及其制备方法 |
CN106478597A (zh) * | 2015-09-02 | 2017-03-08 | 中美华世通生物医药科技(武汉)有限公司 | 富马酸沃诺拉赞单晶及其制备方法和用途 |
CN106511344A (zh) * | 2015-09-14 | 2017-03-22 | 王虹 | 一种胃酸分泌抑制剂的新用途 |
CN106632246A (zh) * | 2015-10-30 | 2017-05-10 | 江苏柯菲平医药股份有限公司 | 一种吡咯类胃酸分泌抑制剂化合物盐的晶型及其制备 |
CN105198802A (zh) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | 一种2-甲基-3-溴吡啶的制备方法 |
CN105294653B (zh) * | 2015-11-16 | 2017-08-15 | 山东罗欣药业集团股份有限公司 | 富马酸沃诺拉赞的制备工艺 |
CN105440019A (zh) * | 2015-12-17 | 2016-03-30 | 昆明贵研药业有限公司 | 一种治疗胃酸疾病药物的制备方法 |
CN105503828A (zh) * | 2015-12-24 | 2016-04-20 | 北京康立生医药技术开发有限公司 | 一种吡咯衍生物的富马酸盐的制备方法 |
CN105461690B (zh) * | 2015-12-24 | 2018-07-24 | 南京济群医药科技股份有限公司 | 高纯度((5-(2-氟苯基)-1-(吡啶-3-基磺酰基)-1h-吡咯-3-基)甲基)(甲基)氨基甲酸叔丁酯的制备方法 |
KR20170113040A (ko) | 2016-03-25 | 2017-10-12 | 주식회사 대웅제약 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민의 신규한 산부가염 |
KR102081920B1 (ko) | 2016-03-25 | 2020-02-26 | 주식회사 대웅제약 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민 염의 신규한 결정형 |
CN106074406A (zh) * | 2016-06-12 | 2016-11-09 | 佛山市腾瑞医药科技有限公司 | 一种富马酸沃诺拉赞分散片及其制备方法 |
CN108191830B (zh) * | 2016-06-30 | 2019-06-14 | 珠海赛隆药业股份有限公司(长沙)医药研发中心 | 一种富马酸沃诺拉赞中间体ⅳ及其制备方法 |
KR101777971B1 (ko) | 2016-07-05 | 2017-09-12 | 제일약품주식회사 | 이미다조[1,2-a]피리딘 유도체, 이의 제조방법 및 이의 용도 |
CN106187852B (zh) * | 2016-07-07 | 2019-01-15 | 江西同和药业股份有限公司 | 一种富马酸沃诺拉赞中间体的制备方法 |
CN106431871A (zh) * | 2016-08-17 | 2017-02-22 | 济南贝莱尔化学科技有限公司 | 一种2′‑溴代邻氟苯乙酮的制备方法 |
CN106243008B (zh) * | 2016-08-22 | 2018-09-04 | 山东金城生物药业有限公司 | 富马酸沃诺拉赞中间体5-(2-氟苯基)-1h-吡咯-3-甲醛的制备方法 |
CN107778207A (zh) * | 2016-08-25 | 2018-03-09 | 广东东阳光药业有限公司 | 富马酸沃诺拉赞中间体及其制备方法和用途 |
CN106380464A (zh) * | 2016-08-31 | 2017-02-08 | 山东新华制药股份有限公司 | 氟呐普拉赞关键中间体的制备方法 |
CN106397404A (zh) * | 2016-08-31 | 2017-02-15 | 山东新华制药股份有限公司 | 5‑(2‑氟苯基)‑1‑(吡啶‑3‑基磺酰基)‑1h‑吡咯‑3‑甲醛的制备方法 |
CN115385845A (zh) * | 2016-09-12 | 2022-11-25 | 江苏柯菲平医药股份有限公司 | 一种吡咯磺酸类化合物盐型制备 |
CN107879964B (zh) * | 2016-09-29 | 2023-02-10 | 江苏柯菲平医药股份有限公司 | 1-(5-(2-氟苯基)-1-(3-(3-甲氧丙氧基)苯磺酰氯)-1h-吡咯-3-基)-n-甲基胺的制备方法 |
CN108069891B (zh) * | 2016-11-16 | 2022-09-20 | 江苏柯菲平医药股份有限公司 | 一类甲基甲胺盐酸盐的a晶型、制备及其应用 |
CN106892900A (zh) * | 2017-04-10 | 2017-06-27 | 山东裕欣药业有限公司 | 一种富马酸沃诺拉赞及其制备方法 |
CN107011327A (zh) * | 2017-04-19 | 2017-08-04 | 刘德鹏 | 一种治疗消化性溃疡的药物化合物及其制备方法 |
CN106905216A (zh) * | 2017-04-19 | 2017-06-30 | 刘德鹏 | 一种质子泵抑制剂药物化合物及其制备方法 |
CN108794449B (zh) * | 2017-05-05 | 2023-08-04 | 广东东阳光药业有限公司 | 一种氘代富马酸沃诺拉赞代谢物的合成方法 |
KR102233455B1 (ko) | 2017-06-21 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
PE20200442A1 (es) * | 2017-07-10 | 2020-02-28 | Takeda Pharmaceuticals Co | Preparacion que comprende vonoprazan |
KR20190057569A (ko) | 2017-11-20 | 2019-05-29 | 제일약품주식회사 | 7-아미노-1h-인돌-5-카르복사미드 유도체 및 이의 용도 |
WO2019131695A1 (ja) * | 2017-12-27 | 2019-07-04 | 日本ケミファ株式会社 | 1-[5-(2-フルオロフェニル)-1-(ピリジン-3-イルスルホニル)-1h-ピロ-ル-3-イル]-n-メチルメタンアミンモノフマル酸塩の製造法 |
CN108558831B (zh) * | 2018-06-08 | 2021-07-27 | 上海璃道医药科技有限公司 | 取代吡咯-4-烷基胺类化合物及其用途 |
CN109053684A (zh) * | 2018-08-09 | 2018-12-21 | 珠海润都制药股份有限公司 | 一种富马酸沃诺拉赞及其中间体的制备方法 |
CN110272409A (zh) * | 2019-03-11 | 2019-09-24 | 南京百迪尔生物医药有限公司 | 一步法合成沃诺拉赞的新方法 |
KR102222443B1 (ko) | 2019-04-11 | 2021-03-03 | 일동제약(주) | 1-[5-(2-플루오로페닐)-1-(피리딘-3-일술포닐)-1h-피롤-3-일]-n-메틸메탄아민의 신규염, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
CN112300123B (zh) * | 2019-08-02 | 2023-07-18 | 上海天慈国际药业有限公司 | 一种沃诺拉赞中间体的制备方法 |
CN110627628A (zh) * | 2019-09-24 | 2019-12-31 | 上海应用技术大学 | 一种β-碘代二氟丙酮类衍生物及其制备方法 |
CN112830920A (zh) * | 2019-11-25 | 2021-05-25 | 杭州华东医药集团新药研究院有限公司 | 一种杂环衍生物、其药物组合物及用途 |
CN111018835B (zh) * | 2019-12-16 | 2022-09-20 | 株洲千金药业股份有限公司 | 一种沃诺拉赞的纯化方法 |
CN113527536B (zh) * | 2020-04-21 | 2024-03-22 | 杭州德柯医疗科技有限公司 | 一种含氟多糖高分子化合物及其制备方法 |
CN114349737B (zh) * | 2020-04-26 | 2023-06-09 | 南京烁慧医药科技有限公司 | 一种含磺酰胺结构的化合物及其应用、一种药物组合物及其应用 |
CN111484458B (zh) * | 2020-05-25 | 2022-12-27 | 南京竹园医药科技有限公司 | 一种2-羟基-5-磺酸基嘧啶的制备方法 |
KR20210156235A (ko) * | 2020-06-17 | 2021-12-24 | 일동제약(주) | 신규한 산 분비 억제제 및 이의 용도 |
CN111943932B (zh) * | 2020-08-06 | 2023-07-14 | 四川国康药业有限公司 | 一种可以治疗消化性溃疡的3-吡啶磺酰-1-n-杂吡咯衍生物及其制备方法和用途 |
CN112812099B (zh) * | 2021-01-19 | 2022-04-26 | 珠海赛隆药业股份有限公司 | 一种用于治疗消化性溃疡的化合物及其制法和用途 |
CN114989138B (zh) * | 2021-03-02 | 2023-06-13 | 天地恒一制药股份有限公司 | 沃诺拉赞盐及其晶型、制备方法和用途 |
WO2023280290A1 (zh) * | 2021-07-09 | 2023-01-12 | 天地恒一制药股份有限公司 | 一种吡咯磺酰类衍生物、及其制备方法与应用 |
CN113620930B (zh) * | 2021-07-12 | 2022-08-16 | 南京烁慧医药科技有限公司 | 一种含磺酰胺结构的化合物及其制备方法和应用、一种药物组合物及应用 |
CN114105962A (zh) * | 2021-10-26 | 2022-03-01 | 南京烁慧医药科技有限公司 | 一种含磺酰胺结构的化合物及其制备方法和应用、一种药物组合物及应用 |
KR20230102353A (ko) * | 2021-12-30 | 2023-07-07 | 주식회사 대웅제약 | 삼중음성유방암의 예방 또는 치료용 약학적 조성물 |
KR20230114147A (ko) | 2022-01-24 | 2023-08-01 | 순천향대학교 산학협력단 | 칼륨 경쟁적 위산분비 억제제의 신규한 공결정, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
CN115232107A (zh) * | 2022-07-29 | 2022-10-25 | 南京唯创远医药科技有限公司 | 一种高纯度富马酸伏诺拉生的制备方法 |
CN116023364A (zh) * | 2023-01-31 | 2023-04-28 | 山东铂源药业股份有限公司 | 一种富马酸沃诺拉赞的制备方法 |
CN117462507B (zh) * | 2023-12-28 | 2024-03-15 | 山东齐都药业有限公司 | 富马酸伏诺拉生药物组合物及其制备方法 |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0259085B1 (en) | 1986-08-29 | 1991-08-21 | Pfizer Inc. | 2-guanidino-4-arylthiazoles for treatment of peptic ulcers |
US5128366A (en) | 1990-07-05 | 1992-07-07 | Shinogi & Co., Ltd. | Pyrrole derivatives |
WO1992004025A1 (en) | 1990-08-31 | 1992-03-19 | Warner-Lambert Company | Amino acid analogs as cck antagonists |
HU219131B (hu) | 1991-10-18 | 2001-02-28 | Monsanto Co. | Módszer és fungicid készítmény növények torsgombabetegségének gátlására és a hatóanyagok |
MX9205392A (es) | 1991-10-29 | 1993-04-01 | Du Pont | Triazolcarbozamidas herbicidas y procedimiento para su obtencion. |
JPH06135961A (ja) | 1992-10-23 | 1994-05-17 | Nippon Iyakuhin Kogyo Kk | 新規ジフェニルピロリルフラン誘導体 |
US5286742A (en) * | 1992-11-03 | 1994-02-15 | American Cyanamid Company | Pyrrole thiocarboxamide insecticidal and acaricidal agents |
US5480902A (en) * | 1993-08-31 | 1996-01-02 | American Cyanamid Company | Thienylpyrrole fungicidal agents |
JPH08119936A (ja) | 1994-10-18 | 1996-05-14 | Fujisawa Pharmaceut Co Ltd | 複素環式誘導体 |
JPH0930967A (ja) | 1995-07-17 | 1997-02-04 | Chugai Pharmaceut Co Ltd | 抗潰瘍剤 |
RU2221782C2 (ru) | 1996-08-28 | 2004-01-20 | Дзе Проктер Энд Гэмбл Компани | Замещенные циклические аминовые ингибиторы металлопротеаз |
SK86699A3 (en) | 1996-12-23 | 2000-11-07 | Du Pont Pharm Co | Nitrogen containing heteroaromatics as factor xa inhibitors |
JPH11209344A (ja) | 1998-01-26 | 1999-08-03 | Kyowa Hakko Kogyo Co Ltd | 含窒素複素環化合物 |
GB9817548D0 (en) * | 1998-08-12 | 1998-10-07 | Novartis Ag | Organic compounds |
US7105564B1 (en) | 1999-03-10 | 2006-09-12 | Shionogi & Co., Ltd. | Pharmaceutical composition comprising a dual antagonist against PGD2/TXA2 receptors having a [2.2.1] or [3.1.1] bicyclic skeleton |
TW575561B (en) | 1999-03-25 | 2004-02-11 | Hoffmann La Roche | 1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives |
DE19913483A1 (de) | 1999-03-25 | 2000-09-28 | Goedecke Ag | Verfahren zur Herstellung von Heterocyclischen Carbamaten aus Aza-Heterocyclen und Kohlendioxid |
AU3783100A (en) | 1999-06-14 | 2000-12-21 | Dow Agrosciences Llc | Substituted triazoles, imidazoles and pyrazoles as herbicides |
DE60024120T2 (de) * | 1999-08-26 | 2006-07-27 | Aventis Pharmaceuticals Inc. | Substituierte (aminoiminomethyl oder aminomethyl) dihydrobenzofurane und benozopyrane |
US6911468B2 (en) | 2000-05-22 | 2005-06-28 | Takeda Chemical Industries, Ltd. | Tyrosine phosphatase inhibitors |
US6589978B2 (en) | 2000-06-30 | 2003-07-08 | Hoffman-La Roche Inc. | 1-sulfonyl pyrrolidine derivatives |
GB0016453D0 (en) | 2000-07-04 | 2000-08-23 | Hoffmann La Roche | Pyrrole derivatives |
CN1582281A (zh) | 2001-10-01 | 2005-02-16 | 大正制药株式会社 | Mch受体拮抗剂 |
MXPA04004464A (es) | 2001-11-08 | 2004-08-11 | Upjohn Co | Compuestos de heteroarilo sustituido con azabiciclo para el tratamiento de enfermedades. |
AU2002342909A1 (en) | 2001-11-22 | 2003-06-10 | Ciba Specialty Chemicals Holding Inc. | Pyrrole synthesis |
US20050101657A1 (en) | 2001-12-28 | 2005-05-12 | Takeda Chemical Industries Ltd. | Androgen receptor antagonists |
AU2003216274A1 (en) | 2002-02-11 | 2003-09-04 | Neurocrine Biosciences, Inc. | Pyrrole derivatives as ligands of melanocortin receptors |
AU2003209114A1 (en) | 2002-02-14 | 2003-09-04 | Wyeth | Pyrrolylalkylidene-hydrazinecarboximidamide derivatives as 5-hydroxytryptamine-6 ligands |
TW200306191A (en) | 2002-02-22 | 2003-11-16 | Teijin Ltd | Pyrrolopyrimidine derivatives |
EP1505964B1 (en) * | 2002-05-17 | 2007-11-21 | Merckle Gmbh | Annelated pyrrole compounds as proton pump inhibitors for treating ulcer |
BR0311707A (pt) | 2002-06-13 | 2005-03-15 | Du Pont | Composto, composição e método de controle de pelo menos uma praga invertebrada |
DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
CA2495216A1 (en) | 2002-08-12 | 2004-02-19 | Sugen, Inc. | 3-pyrrolyl-pyridopyrazoles and 3-pyrrolyl-indazoles as novel kinase inhibitors |
JP2004315511A (ja) | 2003-03-31 | 2004-11-11 | Taisho Pharmaceut Co Ltd | Mch受容体アンタゴニスト |
EP1628957B1 (en) | 2003-05-26 | 2010-09-29 | Takeda Pharmaceutical Company Limited | Sulfopyrroles |
JP2005044740A (ja) | 2003-07-25 | 2005-02-17 | Taniguchi Heaters Kk | 空焚きセンサー内蔵の液中用ヒーター |
JP4239860B2 (ja) | 2004-03-08 | 2009-03-18 | ヤマハ株式会社 | 擦弦楽器用駒および擦弦楽器 |
EP1769092A4 (en) | 2004-06-29 | 2008-08-06 | Europ Nickel Plc | IMPROVED LIXIVIATION OF BASE METALS |
JP2006100626A (ja) | 2004-09-30 | 2006-04-13 | Fuji Photo Film Co Ltd | 半導体発光装置 |
JP5173192B2 (ja) | 2004-09-30 | 2013-03-27 | 武田薬品工業株式会社 | プロトンポンプ阻害薬 |
EP1655284A1 (en) | 2004-10-26 | 2006-05-10 | Aponetics AG | 2-Phenylsulfopyrroles |
RS52473B9 (sr) * | 2005-08-30 | 2019-07-31 | Takeda Pharmaceuticals Co | 1-heterociklilsulfonil, 2-aminometil, 5-(hetero-)aril supstituisani derivati 1-h-pirola kao inhibitori sekrecije kiseline |
KR101366856B1 (ko) * | 2007-03-29 | 2014-02-21 | 삼성전자주식회사 | 다양한 포트를 통해 입력되는 영상을 디스플레이하는디스플레이 장치 |
-
2006
- 2006-08-29 RS RS20120448A patent/RS52473B9/sr unknown
- 2006-08-29 KR KR1020117017886A patent/KR101408561B1/ko active IP Right Grant
- 2006-08-29 PE PE2010001016A patent/PE20110009A1/es active IP Right Grant
- 2006-08-29 WO PCT/JP2006/317408 patent/WO2007026916A1/en active Application Filing
- 2006-08-29 CN CN2006800407897A patent/CN101300229B/zh active Active
- 2006-08-29 US US11/512,629 patent/US7498337B2/en active Active
- 2006-08-29 PL PL11155996T patent/PL2327692T3/pl unknown
- 2006-08-29 PE PE2006001053A patent/PE20070540A1/es active IP Right Grant
- 2006-08-29 AU AU2006285641A patent/AU2006285641A1/en not_active Abandoned
- 2006-08-29 SI SI200631038T patent/SI1919865T1/sl unknown
- 2006-08-29 AR ARP060103754A patent/AR055144A1/es active IP Right Grant
- 2006-08-29 PT PT11155996T patent/PT2327692E/pt unknown
- 2006-08-29 ME MEP-2009-100A patent/ME00610B/me unknown
- 2006-08-29 BR BRPI0615111A patent/BRPI0615111B8/pt active IP Right Grant
- 2006-08-29 TW TW095131827A patent/TWI358296B/zh active
- 2006-08-29 EP EP06797335A patent/EP1919865B1/en active Active
- 2006-08-29 BR BR122017028096A patent/BR122017028096B8/pt active IP Right Grant
- 2006-08-29 SI SI200631443T patent/SI2327692T1/sl unknown
- 2006-08-29 RS RS20110233A patent/RS51697B/en unknown
- 2006-08-29 CA CA2621182A patent/CA2621182C/en active Active
- 2006-08-29 US US11/991,307 patent/US7977488B2/en active Active
- 2006-08-29 JO JO2006287A patent/JO2791B1/en active
- 2006-08-29 PT PT06797335T patent/PT1919865E/pt unknown
- 2006-08-29 ZA ZA200802488A patent/ZA200802488B/xx unknown
- 2006-08-29 UA UAA200803949A patent/UA94424C2/ru unknown
- 2006-08-29 EP EP11155996.9A patent/EP2327692B9/en active Active
- 2006-08-29 JP JP2007524121A patent/JP4035559B1/ja active Active
- 2006-08-29 DE DE602006021195T patent/DE602006021195D1/de active Active
- 2006-08-29 KR KR1020087006439A patent/KR101115857B1/ko active Protection Beyond IP Right Term
- 2006-08-29 ES ES06797335T patent/ES2364498T3/es active Active
- 2006-08-29 DK DK06797335.4T patent/DK1919865T3/da active
- 2006-08-29 DK DK11155996.9T patent/DK2327692T5/da active
- 2006-08-29 GE GEAP200610602A patent/GEP20105044B/en unknown
- 2006-08-29 NZ NZ566378A patent/NZ566378A/en unknown
- 2006-08-29 ES ES11155996T patent/ES2391757T3/es active Active
- 2006-08-29 PL PL06797335T patent/PL1919865T3/pl unknown
- 2006-08-29 AT AT06797335T patent/ATE504567T1/de active
-
2007
- 2007-06-12 JP JP2007155692A patent/JP5204426B2/ja active Active
-
2008
- 2008-02-07 IL IL189375A patent/IL189375A/en active IP Right Grant
- 2008-02-22 CR CR9755A patent/CR9755A/es unknown
- 2008-03-11 MA MA30739A patent/MA29773B1/fr unknown
- 2008-03-25 NO NO20081464A patent/NO341894B1/no unknown
- 2008-09-10 HK HK08110065.1A patent/HK1118547A1/xx unknown
-
2009
- 2009-01-26 US US12/359,762 patent/US8415368B2/en active Active
-
2011
- 2011-03-01 US US13/037,690 patent/US8338461B2/en active Active
- 2011-06-08 US US13/156,226 patent/US8338462B2/en active Active
- 2011-06-08 US US13/156,204 patent/US8436187B2/en active Active
- 2011-06-08 US US13/156,216 patent/US8299261B2/en active Active
- 2011-06-27 HR HR20110473T patent/HRP20110473T1/hr unknown
- 2011-06-30 CY CY20111100637T patent/CY1111922T1/el unknown
- 2011-11-29 HK HK11112910.9A patent/HK1158627A1/xx unknown
-
2012
- 2012-10-03 HR HRP20120792TT patent/HRP20120792T1/hr unknown
- 2012-10-12 CY CY20121100943T patent/CY1114415T1/el unknown
-
2013
- 2013-01-08 JP JP2013001273A patent/JP5687293B2/ja active Active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20110473T1 (hr) | Supstituirani derivati 1-heterociklilsulfonil, 2-aminometil, 5-(hetero)-aril 1-h-pirola kao inhibitori kiselinske sekrecije | |
WO2007125405A3 (en) | Substituted 2-amino-fused heterocyclic compounds | |
AR112074A2 (es) | Derivados de 2-carboxamida-cicloamino-urea como inhibidores de pi-3 | |
EA201071232A1 (ru) | Триазины как ингибиторы киназы pi3 и mtor | |
EA201001772A1 (ru) | Производные 3,5-диамино-6-хлорпиразин-2-карбоновой кислоты и их применение в качестве блокаторов эпителиальных натриевых каналов для лечения заболеваний дыхательных путей | |
EA201170520A1 (ru) | Ингибитор p38 mapk-киназы | |
EP2140867A4 (en) | PHARMACEUTICAL COMPOSITION | |
DK2840080T3 (da) | Nitrogenholdig heterocyklisk forbindelse eller salt deraf | |
PE20091556A1 (es) | Derivado heterociclico fusionado y su uso | |
TW200628154A (en) | Organic compounds | |
HRP20060073B1 (hr) | Fluoro supstituirana omega-karboksiaril difenil urea za lijeäśenje i prevenciju bolesti i stanja | |
ATE486872T1 (de) | Maleimid-derivate, pharmazeutische zusammensetzungen und verfahren zur behandlung von krebs | |
CY1108445T1 (el) | Νεα μεθοδος συνθεσης και νεα κρυσταλλικη μορφη της αγομελατινης καθως και φαρμακευτικες συνθεσεις που την περιεχουν | |
AR041303A1 (es) | Compuestos de piperidinil-imidazopiridina n-sustituidos como moduladores del receptor 5-ht4" | |
EA201270546A1 (ru) | ЗАМЕЩЕННЫЕ ПИПЕРИДИНЫ, КОТОРЫЕ ПОВЫШАЮТ АКТИВНОСТЬ p53, И ИХ ПРИМЕНЕНИЕ | |
EA200900812A1 (ru) | Производные 4-имидазолил-1,2,3,4-тетрагидрохинолина и их применение в качестве ингибиторов альдостерон/11-бета-гидроксилазы | |
CY1112921T1 (el) | Ενεργοποιητες γλυκοκινασης πυρρολιδινονης | |
MX2012007030A (es) | Derivados de acido carboxilico de pirrolidina o tiazolidina, composicion farmaceutica y metodos para su uso en el tratamiento de transtornos metabolicos, como agonistas del receptor 43 acoplado por proteina-g (gpr43). | |
EA201070871A1 (ru) | Бициклические производные азабициклических карбоксамидов, их получение и их применение в терапии | |
BRPI0711310B8 (pt) | composto inibidor de p38 map cinase, composição farmacêutica compreendendo o mesmo e uso do mesmo | |
TW200616958A (en) | New alkyl-pyridines as 11-beta inhibitors for diabetes | |
AR058720A1 (es) | Derivados 2-feniletilamino y composicion farmaceutica | |
HRP20171425T1 (hr) | Derivati oksazolidin-2-on-pirimidina | |
AR092797A1 (es) | Inhibidores de pirazolopirimidinilo de enzima activadora de ubicuitina | |
ES2258780T3 (es) | Derivados de aminocicloalquilpirrolidina sustituidos. |