NO318891B1 - Antihistaminske spiroforbindelser - Google Patents
Antihistaminske spiroforbindelser Download PDFInfo
- Publication number
- NO318891B1 NO318891B1 NO20012710A NO20012710A NO318891B1 NO 318891 B1 NO318891 B1 NO 318891B1 NO 20012710 A NO20012710 A NO 20012710A NO 20012710 A NO20012710 A NO 20012710A NO 318891 B1 NO318891 B1 NO 318891B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- piperidine
- imidazo
- benzazepine
- hydrogen
- Prior art date
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- -1 Antihistamine Spiro Compounds Chemical class 0.000 title claims description 28
- 239000000739 antihistaminic agent Substances 0.000 title description 4
- 230000001387 anti-histamine Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 156
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 33
- 239000002585 base Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000003003 spiro group Chemical group 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 19
- 239000012442 inert solvent Substances 0.000 claims description 19
- 150000001412 amines Chemical group 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- BOYLPLUVCXUHDJ-UHFFFAOYSA-N hydron;spiro[5,6-dihydroimidazo[2,1-b][3]benzazepine-11,4'-piperidine]-3-carboxamide;dichloride Chemical compound Cl.Cl.NC(=O)C1=CN=C2N1CCC1=CC=CC=C1C21CCNCC1 BOYLPLUVCXUHDJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 238000001212 derivatisation Methods 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000000844 transformation Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- QJFZHZBEBWETLO-UHFFFAOYSA-N NC(=O)C1=CN=C2N1CCC1=CC=CC=C1C21CCN(C(O)=O)CC1 Chemical compound NC(=O)C1=CN=C2N1CCC1=CC=CC=C1C21CCN(C(O)=O)CC1 QJFZHZBEBWETLO-UHFFFAOYSA-N 0.000 claims 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 103
- 239000000460 chlorine Substances 0.000 description 87
- 239000000543 intermediate Substances 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000003480 eluent Substances 0.000 description 43
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- 229910002027 silica gel Inorganic materials 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
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- 239000002244 precipitate Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000004440 column chromatography Methods 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
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- 239000000706 filtrate Substances 0.000 description 19
- 125000005843 halogen group Chemical group 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 9
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
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- DELUWFVKRUOYDD-UHFFFAOYSA-N spiro[11-thia-4,7-diazatricyclo[8.3.0.03,7]trideca-1(10),3,5,8,12-pentaene-2,4'-piperidine] Chemical compound C1CNCCC21C1=NC=CN1C=CC1=C2C=CS1 DELUWFVKRUOYDD-UHFFFAOYSA-N 0.000 description 1
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- GMXZOQODAZRCAN-UHFFFAOYSA-N spiro[5,6-dihydroimidazo[2,1-b][3]benzazepine-11,4'-piperidine]-3-ylmethanol Chemical compound OCC1=CN=C2N1CCC1=CC=CC=C1C21CCNCC1 GMXZOQODAZRCAN-UHFFFAOYSA-N 0.000 description 1
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- WWWDRKSCWCFVAJ-UHFFFAOYSA-N tert-butyl 3-formylspiro[5,6-dihydroimidazo[2,1-b][3]benzazepine-11,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC21C1=CC=CC=C1CCN1C(C=O)=CN=C12 WWWDRKSCWCFVAJ-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
- 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
- C07D487/12—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 three hetero rings
- C07D487/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Dental Preparations (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98204347 | 1998-12-19 | ||
| PCT/EP1999/010176 WO2000037470A1 (en) | 1998-12-19 | 1999-12-15 | Antihistaminic spiro compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20012710L NO20012710L (no) | 2001-06-01 |
| NO20012710D0 NO20012710D0 (no) | 2001-06-01 |
| NO318891B1 true NO318891B1 (no) | 2005-05-18 |
Family
ID=8234498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20012710A NO318891B1 (no) | 1998-12-19 | 2001-06-01 | Antihistaminske spiroforbindelser |
Country Status (37)
| Country | Link |
|---|---|
| US (2) | US7148214B1 (pt) |
| EP (1) | EP1144411B1 (pt) |
| JP (1) | JP4601175B2 (pt) |
| KR (1) | KR100598725B1 (pt) |
| CN (1) | CN1258533C (pt) |
| AR (1) | AR021888A1 (pt) |
| AT (1) | ATE294178T1 (pt) |
| AU (1) | AU764820C (pt) |
| BG (1) | BG65133B1 (pt) |
| BR (1) | BR9916371A (pt) |
| CA (1) | CA2355939C (pt) |
| CO (1) | CO5140116A1 (pt) |
| CZ (1) | CZ301953B6 (pt) |
| DE (1) | DE69925036T2 (pt) |
| DK (1) | DK1144411T3 (pt) |
| EA (1) | EA004500B1 (pt) |
| EE (1) | EE04917B1 (pt) |
| EG (1) | EG24605A (pt) |
| ES (1) | ES2242443T3 (pt) |
| HK (1) | HK1043128B (pt) |
| HR (1) | HRP20010453B1 (pt) |
| HU (1) | HU229406B1 (pt) |
| ID (1) | ID29268A (pt) |
| IL (1) | IL143767A0 (pt) |
| MY (1) | MY129663A (pt) |
| NO (1) | NO318891B1 (pt) |
| NZ (1) | NZ512870A (pt) |
| PL (1) | PL196262B1 (pt) |
| PT (1) | PT1144411E (pt) |
| SA (1) | SA00210113B1 (pt) |
| SI (1) | SI1144411T1 (pt) |
| SK (1) | SK286158B6 (pt) |
| TR (1) | TR200101711T2 (pt) |
| TW (1) | TWI250981B (pt) |
| UA (1) | UA74537C2 (pt) |
| WO (1) | WO2000037470A1 (pt) |
| ZA (1) | ZA200104977B (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100898562B1 (ko) * | 2001-10-15 | 2009-05-20 | 얀센 파마슈티카 엔.브이. | 신규 치환된 4-페닐-4-[1ｈ-이미다졸-2-일]-피페리딘유도체 및 선택적인 비펩타이드 델타 아편유사작용제로서의 그의 용도 |
| DE60216310T2 (de) | 2001-10-15 | 2007-06-21 | Janssen Pharmaceutica N.V. | Substituierte 4-phenyl-4-(1h-imidazol-2-yl)-piperidinderivate zur verringerung von ischämischer schädigung |
| WO2005110685A2 (en) * | 2004-05-11 | 2005-11-24 | Alliss George E | Vegetation trimmer apparatus |
| WO2006028239A1 (ja) * | 2004-09-07 | 2006-03-16 | Banyu Pharmaceutical Co., Ltd. | カルバモイル置換スピロ誘導体 |
| KR101390081B1 (ko) | 2008-04-29 | 2014-04-29 | 노파르티스 아게 | 기생충 질환의 치료를 위한 스피로－인돌 유도체 |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| EA201690713A1 (ru) | 2013-10-04 | 2016-08-31 | Инфинити Фармасьютикалз, Инк. | Гетероциклические соединения и их применения |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| DK3119397T3 (da) | 2014-03-19 | 2022-03-28 | Infinity Pharmaceuticals Inc | Heterocykliske forbindelser til anvendelse i behandling af PI3K-gamma-medierede lidelser |
| EP3186242B1 (en) | 2014-08-29 | 2021-10-06 | Tes Pharma S.r.l. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| WO2017088080A1 (es) | 2015-11-25 | 2017-06-01 | Natural Response S.A. | Método para la obtención de saponinas a partir de plantas |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR20240052355A (ko) | 2022-10-14 | 2024-04-23 | 지이 일렉트리컬 엔지니어링 컴퍼니., 리미티드. | 여과 장치용 커버 |
| KR20240052354A (ko) | 2022-10-14 | 2024-04-23 | 지이 일렉트리컬 엔지니어링 컴퍼니., 리미티드. | 여과 장치 |
| CN117624052B (zh) * | 2024-01-26 | 2024-04-12 | 四川益能康生环保科技有限公司 | 一种用于捕集二氧化碳的离子液体及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464380A (en) | 1983-05-25 | 1984-08-07 | Pfizer Inc. | Imidazolidinedione derivatives |
| PH30434A (en) * | 1989-04-07 | 1997-05-09 | Janssen Pharmaceutica Nv | Hydroxyalkylfuranyl derivatives |
| DE69110685T2 (de) * | 1990-10-10 | 1995-11-09 | Schering Corp | Substituierte imidazobenzazepine und imidazopyridoazepine. |
| IL101851A (en) * | 1991-06-13 | 1996-05-14 | Janssen Pharmaceutica Nv | History 01 -) 4 - Pipridinyl - and Pipridinylidene (- Imidazo] A-1,2 [Pirolo, Thiano or Purano (] 3,2 [Azpin, their preparation and pharmaceutical preparations containing them and composition |
| IL101850A (en) * | 1991-06-13 | 1996-01-31 | Janssen Pharmaceutica Nv | History 11-) 4-Pipridinyl (-Imidazo] B-1, 2 [] 3 [Benzazepine, their preparation and pharmaceutical preparations containing them |
| US5106844A (en) * | 1991-09-10 | 1992-04-21 | Sterling Drug Inc. | Imidazo[2,2-b][3]benzazepine and pyrimido[2,1-b][3]benzazepine antiarrhythmic agents |
| TW382017B (en) | 1995-12-27 | 2000-02-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-(fused imidazole)-piperidine derivatives |
-
1999
- 1999-12-15 HU HU0104779A patent/HU229406B1/hu unknown
- 1999-12-15 WO PCT/EP1999/010176 patent/WO2000037470A1/en active IP Right Grant
- 1999-12-15 UA UA2001064351A patent/UA74537C2/uk unknown
- 1999-12-15 EE EEP200100328A patent/EE04917B1/xx unknown
- 1999-12-15 EA EA200100681A patent/EA004500B1/ru not_active IP Right Cessation
- 1999-12-15 ES ES99964625T patent/ES2242443T3/es not_active Expired - Lifetime
- 1999-12-15 CZ CZ20012069A patent/CZ301953B6/cs not_active IP Right Cessation
- 1999-12-15 CA CA2355939A patent/CA2355939C/en not_active Expired - Lifetime
- 1999-12-15 IL IL14376799A patent/IL143767A0/xx not_active IP Right Cessation
- 1999-12-15 DE DE69925036T patent/DE69925036T2/de not_active Expired - Lifetime
- 1999-12-15 SK SK814-2001A patent/SK286158B6/sk not_active IP Right Cessation
- 1999-12-15 TR TR2001/01711T patent/TR200101711T2/xx unknown
- 1999-12-15 KR KR1020017005016A patent/KR100598725B1/ko active IP Right Grant
- 1999-12-15 DK DK99964625T patent/DK1144411T3/da active
- 1999-12-15 PT PT99964625T patent/PT1144411E/pt unknown
- 1999-12-15 ID IDW00200101298A patent/ID29268A/id unknown
- 1999-12-15 AT AT99964625T patent/ATE294178T1/de active
- 1999-12-15 CN CNB998147052A patent/CN1258533C/zh not_active Expired - Lifetime
- 1999-12-15 NZ NZ512870A patent/NZ512870A/en not_active IP Right Cessation
- 1999-12-15 AU AU30412/00A patent/AU764820C/en not_active Expired
- 1999-12-15 EP EP99964625A patent/EP1144411B1/en not_active Expired - Lifetime
- 1999-12-15 SI SI9930798T patent/SI1144411T1/xx unknown
- 1999-12-15 BR BR9916371-3A patent/BR9916371A/pt not_active Application Discontinuation
- 1999-12-15 JP JP2000589540A patent/JP4601175B2/ja not_active Expired - Lifetime
- 1999-12-15 US US09/868,535 patent/US7148214B1/en not_active Expired - Lifetime
- 1999-12-15 PL PL348295A patent/PL196262B1/pl unknown
- 1999-12-17 TW TW088122194A patent/TWI250981B/zh not_active IP Right Cessation
- 1999-12-17 CO CO99079021A patent/CO5140116A1/es unknown
- 1999-12-17 AR ARP990106513A patent/AR021888A1/es active IP Right Grant
- 1999-12-17 MY MYPI99005537A patent/MY129663A/en unknown
- 1999-12-18 EG EG162699A patent/EG24605A/xx active
-
2000
- 2000-05-21 SA SA00210113A patent/SA00210113B1/ar unknown
-
2001
- 2001-05-29 BG BG105546A patent/BG65133B1/bg unknown
- 2001-06-01 NO NO20012710A patent/NO318891B1/no not_active IP Right Cessation
- 2001-06-15 HR HR20010453A patent/HRP20010453B1/xx not_active IP Right Cessation
- 2001-06-18 ZA ZA200104977A patent/ZA200104977B/en unknown
-
2002
- 2002-07-03 HK HK02104999.1A patent/HK1043128B/zh unknown
-
2004
- 2004-07-26 US US10/898,844 patent/US7087595B2/en not_active Expired - Lifetime
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Legal Events
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| MK1K | Patent expired |