IL125982A - Modules-2 (Arylphenyl) Amino-imidazoline, their preparation and pharmaceutical preparations containing them - Google Patents
Modules-2 (Arylphenyl) Amino-imidazoline, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL125982A IL125982A IL12598298A IL12598298A IL125982A IL 125982 A IL125982 A IL 125982A IL 12598298 A IL12598298 A IL 12598298A IL 12598298 A IL12598298 A IL 12598298A IL 125982 A IL125982 A IL 125982A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- phenyl
- amino
- imidazoline
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 65
- 238000002360 preparation method Methods 0.000 title claims description 48
- MSYFITFSZJKRQJ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-amine Chemical class NN1CCN=C1 MSYFITFSZJKRQJ-UHFFFAOYSA-N 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 254
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 21
- 239000013078 crystal Chemical group 0.000 claims abstract description 20
- 208000002193 Pain Diseases 0.000 claims abstract description 19
- 230000036407 pain Effects 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000003839 salts Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000036303 septic shock Effects 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 6
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- 206010061218 Inflammation Diseases 0.000 claims abstract description 5
- 230000004054 inflammatory process Effects 0.000 claims abstract description 5
- 208000005279 Status Asthmaticus Diseases 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 124
- -1 isobuty Chemical group 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 239000004615 ingredient Substances 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- HSUNTNVKARKFSK-UHFFFAOYSA-N 4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]-N-(2-methylpropyl)benzamide Chemical compound CC(C)CNC(=O)c1ccc(Cc2ccc(cc2)C2=NCCN2N)cc1 HSUNTNVKARKFSK-UHFFFAOYSA-N 0.000 claims description 2
- GMPVPGBTHQYYCE-UHFFFAOYSA-N 4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]-N-benzylbenzamide Chemical compound NN1CCN=C1c1ccc(Cc2ccc(cc2)C(=O)NCc2ccccc2)cc1 GMPVPGBTHQYYCE-UHFFFAOYSA-N 0.000 claims description 2
- ZODCLJXQLFWUHZ-UHFFFAOYSA-N n-[4-[[4-(oxan-4-yloxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(OC2CCOCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 ZODCLJXQLFWUHZ-UHFFFAOYSA-N 0.000 claims description 2
- JTGYESHCFUAHOD-UHFFFAOYSA-N 4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]-N-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)c1ccc(Cc2ccc(cc2)C2=NCCN2N)cc1 JTGYESHCFUAHOD-UHFFFAOYSA-N 0.000 claims 1
- PNIKVPRTLDFVGX-UHFFFAOYSA-N 4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]-n-butylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCC)=CC=C1CC1=CC=C(C=2N(CCN=2)N)C=C1 PNIKVPRTLDFVGX-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 249
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 168
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 72
- 239000002904 solvent Substances 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
- 238000004458 analytical method Methods 0.000 description 66
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- 229940093499 ethyl acetate Drugs 0.000 description 56
- 235000019439 ethyl acetate Nutrition 0.000 description 56
- 239000007787 solid Substances 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 50
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 48
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 20
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Classifications
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- 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
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4168—1,3-Diazoles having a nitrogen attached in position 2, e.g. clonidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P11/06—Antiasthmatics
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- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/10—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 carbon chain containing aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (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)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Lenses (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5780897P | 1997-09-04 | 1997-09-04 | |
US8991698P | 1998-06-19 | 1998-06-19 |
Publications (2)
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IL125982A0 IL125982A0 (en) | 1999-04-11 |
IL125982A true IL125982A (en) | 2002-09-12 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IL12598298A IL125982A (en) | 1997-09-04 | 1998-08-28 | Modules-2 (Arylphenyl) Amino-imidazoline, their preparation and pharmaceutical preparations containing them |
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EP (1) | EP0902018B1 (zh) |
JP (1) | JP3040752B2 (zh) |
KR (1) | KR100309191B1 (zh) |
CN (1) | CN1110484C (zh) |
AT (1) | ATE402151T1 (zh) |
AU (1) | AU746480B2 (zh) |
CA (1) | CA2245755A1 (zh) |
CZ (1) | CZ278198A3 (zh) |
DE (1) | DE69839753D1 (zh) |
DK (1) | DK0902018T3 (zh) |
HK (1) | HK1019334A1 (zh) |
HU (1) | HUP9801950A3 (zh) |
IL (1) | IL125982A (zh) |
MA (1) | MA26541A1 (zh) |
NO (1) | NO312294B1 (zh) |
NZ (1) | NZ331480A (zh) |
PT (1) | PT902018E (zh) |
RU (1) | RU2211834C2 (zh) |
TW (1) | TW432046B (zh) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2001068591A1 (en) | 2000-03-16 | 2001-09-20 | F. Hoffmann-La Roche Ag | Carboxylic acid derivatives as ip antagonists |
CN1468227A (zh) * | 2000-08-08 | 2004-01-14 | ����-������ҩƷ��˾ | 非咪唑芳氧基烷基胺 |
JP4909487B2 (ja) * | 2000-08-30 | 2012-04-04 | 学校法人神奈川大学 | オキセタン変性化合物とそれから誘導される光硬化性化合物、それらの製造方法及びそれらを含有する硬化性組成物 |
PL362549A1 (en) * | 2000-11-14 | 2004-11-02 | F.Hoffmann-La Roche Ag | Substituted 2-phenylaminoimidazoline phenyl ketone derivatives as ip antagonists |
US20060171945A1 (en) * | 2003-02-14 | 2006-08-03 | Critchley Hilary Octavia D | Ip receptor antagonists for the treatment of pathological uterine conditions |
EP1622611A1 (en) * | 2003-05-01 | 2006-02-08 | F. Hoffmann-La Roche Ag | Imidazolin-2-ylaminophenyl amides as ip antagonists |
EP1656350A2 (en) * | 2003-07-09 | 2006-05-17 | F.Hoffmann-La Roche Ag | Thiophenylaminoimidazolines as prostaglandin i2 antagonists |
EP2513064B1 (en) | 2009-12-17 | 2018-07-04 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Compounds, compositions and methods for controlling biofilms |
US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
EP2600864B1 (en) * | 2010-08-04 | 2019-01-09 | University Of Virginia Patent Foundation | Compositions and methods for treating inflammatory diseases |
WO2014032755A2 (en) * | 2012-08-29 | 2014-03-06 | Merck Patent Gmbh | Ddr2 inhibitors for the treatment of osteoarthritis |
US9321745B2 (en) | 2013-03-12 | 2016-04-26 | Allergan, Inc. | Inhibition of neovascularization by inhibition of prostanoid IP receptors |
WO2014143591A1 (en) | 2013-03-12 | 2014-09-18 | Allergan, Inc. | Inhibition of neovascularization by simultaneous inhibition of prostanoid ip and ep4 receptors |
WO2016043260A1 (ja) * | 2014-09-19 | 2016-03-24 | 塩野義製薬株式会社 | 環状グアニジンまたはアミジン化合物 |
US9827225B2 (en) | 2016-01-25 | 2017-11-28 | Jenivision Inc. | Use of prostacyclin antagonists for treating ocular surface nociception |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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NL7711390A (nl) | 1977-10-18 | 1979-04-20 | Philips Nv | Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen. |
NL7810350A (nl) | 1978-10-16 | 1980-04-18 | Duphar Int Res | Preparaat met groeiregulerende werking en gebruik van dit preparaat in land- en tuinbouw. |
CA1138451A (en) | 1979-04-03 | 1982-12-28 | Ikuo Ueda | 2-imidazoline derivatives, process for the preparation thereof and the pharmaceutical composition of the same |
US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
US4889868A (en) | 1984-12-20 | 1989-12-26 | Rorer Pharmaceutical Corporation | Bis-imidazolinoamino derivatives as antiallergy compounds |
WO1993017681A1 (en) | 1992-03-02 | 1993-09-16 | Abbott Laboratories | Angiotensin ii receptor antagonists |
GB9506188D0 (en) | 1995-03-27 | 1995-05-17 | Fujisawa Pharmaceutical Co | Amidine derivatives |
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1998
- 1998-08-20 NZ NZ331480A patent/NZ331480A/en unknown
- 1998-08-26 EP EP98116091A patent/EP0902018B1/en not_active Expired - Lifetime
- 1998-08-26 DE DE69839753T patent/DE69839753D1/de not_active Expired - Fee Related
- 1998-08-26 DK DK98116091T patent/DK0902018T3/da active
- 1998-08-26 AT AT98116091T patent/ATE402151T1/de not_active IP Right Cessation
- 1998-08-26 PT PT98116091T patent/PT902018E/pt unknown
- 1998-08-27 CA CA002245755A patent/CA2245755A1/en not_active Abandoned
- 1998-08-28 IL IL12598298A patent/IL125982A/en not_active IP Right Cessation
- 1998-08-31 HU HU9801950A patent/HUP9801950A3/hu unknown
- 1998-09-01 CZ CZ982781A patent/CZ278198A3/cs unknown
- 1998-09-01 MA MA25239A patent/MA26541A1/fr unknown
- 1998-09-02 JP JP10248047A patent/JP3040752B2/ja not_active Expired - Fee Related
- 1998-09-03 NO NO19984044A patent/NO312294B1/no not_active IP Right Cessation
- 1998-09-03 RU RU98117245/04A patent/RU2211834C2/ru not_active IP Right Cessation
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- 1998-09-04 KR KR1019980036524A patent/KR100309191B1/ko not_active IP Right Cessation
- 1998-09-08 TW TW087114724A patent/TW432046B/zh active
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1999
- 1999-10-07 HK HK99104374A patent/HK1019334A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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NO312294B1 (no) | 2002-04-22 |
HUP9801950A3 (en) | 2001-12-28 |
CN1110484C (zh) | 2003-06-04 |
EP0902018A2 (en) | 1999-03-17 |
HK1019334A1 (en) | 2000-02-03 |
NZ331480A (en) | 2000-02-28 |
EP0902018B1 (en) | 2008-07-23 |
CZ278198A3 (cs) | 1999-04-14 |
NO984044L (no) | 1999-03-05 |
MA26541A1 (fr) | 2004-12-20 |
AU746480B2 (en) | 2002-05-02 |
PT902018E (pt) | 2008-09-05 |
CA2245755A1 (en) | 1999-03-04 |
NO984044D0 (no) | 1998-09-03 |
EP0902018A3 (en) | 2001-05-02 |
KR19990029550A (ko) | 1999-04-26 |
HUP9801950A2 (hu) | 1999-03-29 |
RU2211834C2 (ru) | 2003-09-10 |
JPH11140057A (ja) | 1999-05-25 |
DE69839753D1 (de) | 2008-09-04 |
DK0902018T3 (da) | 2008-10-20 |
IL125982A0 (en) | 1999-04-11 |
HU9801950D0 (en) | 1998-10-28 |
ATE402151T1 (de) | 2008-08-15 |
TW432046B (en) | 2001-05-01 |
JP3040752B2 (ja) | 2000-05-15 |
CN1216762A (zh) | 1999-05-19 |
AU8309498A (en) | 1999-03-18 |
KR100309191B1 (ko) | 2001-12-12 |
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