NO321334B1 - 5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. - Google Patents
5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. Download PDFInfo
- Publication number
- NO321334B1 NO321334B1 NO20015701A NO20015701A NO321334B1 NO 321334 B1 NO321334 B1 NO 321334B1 NO 20015701 A NO20015701 A NO 20015701A NO 20015701 A NO20015701 A NO 20015701A NO 321334 B1 NO321334 B1 NO 321334B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- trifluoromethyl
- bis
- benzyl
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 8
- 201000010099 disease Diseases 0.000 title claims abstract 4
- 239000003814 drug Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- LVXOXXGCJHYEOS-UHFFFAOYSA-N 5-phenylpyrimidine Chemical class C1=CC=CC=C1C1=CN=CN=C1 LVXOXXGCJHYEOS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- -1 amino, hydroxy Chemical group 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims abstract description 4
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 18
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229940047889 isobutyramide Drugs 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- NJSCUZLQCLYCIE-UHFFFAOYSA-N 5-(2-methylphenyl)-2-methylsulfanylpyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=NC(SC)=NC=C1C1=CC=CC=C1C NJSCUZLQCLYCIE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- FFYPMPCDMDDUCS-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[5-(2-chlorophenyl)-2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-n,2-dimethylpropanamide Chemical compound N=1C(N2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FFYPMPCDMDDUCS-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- UDRXMUSKHDXOJG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-n-methyl-2-[(4-methylpiperazin-1-yl)methyl]pyrimidine-4-carboxamide Chemical compound N=1C(CN2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UDRXMUSKHDXOJG-UHFFFAOYSA-N 0.000 claims 1
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- 101100412446 Caenorhabditis elegans rer-1 gene Proteins 0.000 abstract 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99110482 | 1999-05-31 | ||
| PCT/EP2000/004702 WO2000073278A2 (en) | 1999-05-31 | 2000-05-24 | 5-phenyl-pyrimidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20015701D0 NO20015701D0 (no) | 2001-11-22 |
| NO20015701L NO20015701L (no) | 2001-11-22 |
| NO321334B1 true NO321334B1 (no) | 2006-04-24 |
Family
ID=8238270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20015701A NO321334B1 (no) | 1999-05-31 | 2001-11-22 | 5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6756380B1 (sl) |
| EP (1) | EP1187814B1 (sl) |
| JP (1) | JP3590591B2 (sl) |
| KR (1) | KR100478369B1 (sl) |
| CN (1) | CN1187338C (sl) |
| AR (1) | AR024145A1 (sl) |
| AT (1) | ATE273962T1 (sl) |
| AU (1) | AU769265B2 (sl) |
| BR (1) | BR0011097A (sl) |
| CA (1) | CA2375670C (sl) |
| CO (1) | CO5170529A1 (sl) |
| CZ (1) | CZ20014273A3 (sl) |
| DE (1) | DE60013127T2 (sl) |
| DK (1) | DK1187814T3 (sl) |
| ES (1) | ES2225144T3 (sl) |
| GC (1) | GC0000338A (sl) |
| HK (1) | HK1046411B (sl) |
| HR (1) | HRP20010867A2 (sl) |
| HU (1) | HU225016B1 (sl) |
| IL (2) | IL146519A0 (sl) |
| JO (1) | JO2308B1 (sl) |
| MA (1) | MA26794A1 (sl) |
| MX (1) | MXPA01011704A (sl) |
| MY (1) | MY136258A (sl) |
| NO (1) | NO321334B1 (sl) |
| NZ (1) | NZ515408A (sl) |
| PE (1) | PE20010203A1 (sl) |
| PL (1) | PL353492A1 (sl) |
| PT (1) | PT1187814E (sl) |
| RU (1) | RU2244710C2 (sl) |
| SI (1) | SI1187814T1 (sl) |
| TR (1) | TR200103460T2 (sl) |
| TW (1) | TWI263638B (sl) |
| WO (1) | WO2000073278A2 (sl) |
| YU (1) | YU85001A (sl) |
| ZA (1) | ZA200109496B (sl) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
| CA2412010A1 (en) | 2000-06-13 | 2001-12-20 | Basf Aktiengesellschaft | Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines |
| CA2432642A1 (en) | 2000-12-21 | 2002-08-08 | Subhash P. Khanapure | Substituted aryl compounds as novel cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| WO2004004731A1 (en) | 2002-07-02 | 2004-01-15 | F. Hoffmann-La Roche Ag | 2, 5-substituted pyrimidine derivatives as ccr-3 receptor antagonists ix |
| US7935698B2 (en) * | 2003-11-10 | 2011-05-03 | Synta Pharmaceuticals Corporation | Heteroaryl-hydrazone compounds |
| JP2007217282A (ja) * | 2004-03-04 | 2007-08-30 | Astellas Pharma Inc | 置換ピリミジン誘導体 |
| WO2006053227A2 (en) * | 2004-11-10 | 2006-05-18 | Synta Pharmaceuticals Corp. | Il-12 modulatory compounds |
| RU2007129642A (ru) | 2005-02-25 | 2009-03-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Таблетки с улучшенным распределением лекарственного вещества |
| US9013997B2 (en) | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
| AU2014232383B2 (en) | 2013-03-15 | 2019-01-17 | Epigen Biosciences, Inc. | Heterocyclic compounds useful in the treatment of disease |
| GB201316600D0 (en) * | 2013-09-18 | 2013-10-30 | Redx Pharma Ltd | Agricultural chemicals |
| WO2016021562A1 (ja) * | 2014-08-06 | 2016-02-11 | キッセイ薬品工業株式会社 | シアノチオフェン誘導体 |
| MX2017009843A (es) | 2015-01-30 | 2017-11-02 | Basf Se | Fenilpirimidinas herbicidas. |
| WO2018015180A1 (en) | 2016-07-20 | 2018-01-25 | Basf Se | Herbicidal compositions comprising phenylpyrimidines |
| BR112018076518A2 (pt) | 2016-07-25 | 2019-04-02 | Basf Se | compostos de pirimidina, utilização de compostos de pirimidina, composições herbicidas, composição, método para o controle da vegetação indesejada e utilização das composições |
| AU2017302982A1 (en) | 2016-07-25 | 2019-01-03 | Basf Se | Herbicidal pyrimidine compounds |
| EP3490985B1 (en) | 2016-07-26 | 2020-08-05 | Basf Se | Herbicidal pyrimidine compounds |
| WO2018019765A1 (en) | 2016-07-27 | 2018-02-01 | Basf Se | Herbicidal pyrimidine compounds |
| US20210345613A1 (en) | 2016-07-28 | 2021-11-11 | Basf Se | Herbicidal pyrimidine compounds |
| AU2018283422A1 (en) | 2017-06-14 | 2019-12-19 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121408A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121374A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121373A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121352A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| EP3853219B1 (de) * | 2018-09-19 | 2023-07-12 | Bayer Aktiengesellschaft | Herbizid wirksame substituierte phenylpyrimidinhydrazide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208171A1 (es) | 1972-09-29 | 1976-12-09 | Ciba Geigy Ag | Procedimiento para la obtencion de nuevos derivados del acido cef-3-em-4-carboxilico |
| EP0737192B1 (en) | 1993-12-29 | 2001-10-31 | Merck Sharp & Dohme Ltd. | Substituted morpholine derivatives and their use as therapeutic agents |
| WO1997009315A1 (en) | 1995-09-01 | 1997-03-13 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
-
2000
- 2000-01-02 JO JO200082A patent/JO2308B1/en active
- 2000-05-19 TW TW089109624A patent/TWI263638B/zh not_active IP Right Cessation
- 2000-05-22 US US09/575,789 patent/US6756380B1/en not_active Expired - Fee Related
- 2000-05-24 EP EP00935104A patent/EP1187814B1/en not_active Expired - Lifetime
- 2000-05-24 MX MXPA01011704A patent/MXPA01011704A/es active IP Right Grant
- 2000-05-24 DE DE60013127T patent/DE60013127T2/de not_active Expired - Fee Related
- 2000-05-24 TR TR2001/03460T patent/TR200103460T2/xx unknown
- 2000-05-24 AU AU50708/00A patent/AU769265B2/en not_active Ceased
- 2000-05-24 SI SI200030472T patent/SI1187814T1/sl unknown
- 2000-05-24 YU YU85001A patent/YU85001A/sh unknown
- 2000-05-24 HU HU0201527A patent/HU225016B1/hu not_active IP Right Cessation
- 2000-05-24 DK DK00935104T patent/DK1187814T3/da active
- 2000-05-24 JP JP2000621344A patent/JP3590591B2/ja not_active Expired - Fee Related
- 2000-05-24 CZ CZ20014273A patent/CZ20014273A3/cs unknown
- 2000-05-24 WO PCT/EP2000/004702 patent/WO2000073278A2/en not_active Application Discontinuation
- 2000-05-24 KR KR10-2001-7015319A patent/KR100478369B1/ko not_active IP Right Cessation
- 2000-05-24 AT AT00935104T patent/ATE273962T1/de not_active IP Right Cessation
- 2000-05-24 IL IL14651900A patent/IL146519A0/xx not_active IP Right Cessation
- 2000-05-24 NZ NZ515408A patent/NZ515408A/xx unknown
- 2000-05-24 PT PT00935104T patent/PT1187814E/pt unknown
- 2000-05-24 BR BR0011097-3A patent/BR0011097A/pt not_active Application Discontinuation
- 2000-05-24 RU RU2001133456/04A patent/RU2244710C2/ru not_active IP Right Cessation
- 2000-05-24 CN CNB008082847A patent/CN1187338C/zh not_active Expired - Fee Related
- 2000-05-24 ES ES00935104T patent/ES2225144T3/es not_active Expired - Lifetime
- 2000-05-24 CA CA002375670A patent/CA2375670C/en not_active Expired - Fee Related
- 2000-05-24 PL PL00353492A patent/PL353492A1/xx unknown
- 2000-05-26 PE PE2000000509A patent/PE20010203A1/es not_active Application Discontinuation
- 2000-05-29 MY MYPI20002385A patent/MY136258A/en unknown
- 2000-05-29 CO CO00039601A patent/CO5170529A1/es not_active Application Discontinuation
- 2000-05-29 AR ARP000102642A patent/AR024145A1/es not_active Application Discontinuation
- 2000-05-30 GC GCP2000685 patent/GC0000338A/en active
-
2001
- 2001-11-15 IL IL146519A patent/IL146519A/en unknown
- 2001-11-16 ZA ZA200109496A patent/ZA200109496B/en unknown
- 2001-11-22 HR HR20010867A patent/HRP20010867A2/hr not_active Application Discontinuation
- 2001-11-22 NO NO20015701A patent/NO321334B1/no not_active Application Discontinuation
- 2001-11-26 MA MA26425A patent/MA26794A1/fr unknown
-
2002
- 2002-11-05 HK HK02108020.5A patent/HK1046411B/zh not_active IP Right Cessation
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |