NO310235B1 - Pyrimidin-derivater, anvendelse av dem og farmasöytiske blandinger inneholdende dem - Google Patents
Pyrimidin-derivater, anvendelse av dem og farmasöytiske blandinger inneholdende dem Download PDFInfo
- Publication number
- NO310235B1 NO310235B1 NO19980959A NO980959A NO310235B1 NO 310235 B1 NO310235 B1 NO 310235B1 NO 19980959 A NO19980959 A NO 19980959A NO 980959 A NO980959 A NO 980959A NO 310235 B1 NO310235 B1 NO 310235B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxyphenoxy
- compound
- synthesis
- butyl
- butylphenylsulfonylamino
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title claims description 20
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
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- 239000000203 mixture Substances 0.000 claims description 21
- 102000002045 Endothelin Human genes 0.000 claims description 16
- 108050009340 Endothelin Proteins 0.000 claims description 16
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 16
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- 201000010099 disease Diseases 0.000 claims description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 230000006806 disease prevention Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 61
- 238000003786 synthesis reaction Methods 0.000 description 61
- 238000000034 method Methods 0.000 description 47
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 108010091212 pepstatin Proteins 0.000 description 1
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- OZIWEYQVUCTOIU-UHFFFAOYSA-K sodium;trichlororuthenium Chemical compound [Na].Cl[Ru](Cl)Cl OZIWEYQVUCTOIU-UHFFFAOYSA-K 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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
- UYQCMUNLWYSDCN-UHFFFAOYSA-N tert-butyl 4-[4-[(4-tert-butylphenyl)sulfonylamino]-5-(2-methoxyphenoxy)-6-[3-oxo-3-(2-propan-2-ylanilino)propoxy]pyrimidin-2-yl]piperazine-1-carboxylate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)N2CCN(CC2)C(=O)OC(C)(C)C)OCCC(=O)NC=2C(=CC=CC=2)C(C)C)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 UYQCMUNLWYSDCN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D239/52—Two oxygen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22890795 | 1995-09-06 | ||
| PCT/JP1996/002494 WO1997009318A1 (fr) | 1995-09-06 | 1996-09-04 | Derives de la pyrimidine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO980959L NO980959L (no) | 1998-03-05 |
| NO980959D0 NO980959D0 (no) | 1998-03-05 |
| NO310235B1 true NO310235B1 (no) | 2001-06-11 |
Family
ID=16883731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19980959A NO310235B1 (no) | 1995-09-06 | 1998-03-05 | Pyrimidin-derivater, anvendelse av dem og farmasöytiske blandinger inneholdende dem |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5883092A (fr) |
| EP (1) | EP0852226B1 (fr) |
| KR (1) | KR100453097B1 (fr) |
| CN (1) | CN1105711C (fr) |
| AT (1) | ATE254607T1 (fr) |
| AU (1) | AU703892B2 (fr) |
| CA (1) | CA2230516C (fr) |
| DE (1) | DE69630799T2 (fr) |
| ES (1) | ES2210384T3 (fr) |
| HU (1) | HUP9903526A3 (fr) |
| NO (1) | NO310235B1 (fr) |
| PT (1) | PT852226E (fr) |
| RU (1) | RU2170734C2 (fr) |
| WO (1) | WO1997009318A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0801062B1 (fr) * | 1994-12-28 | 2003-04-23 | Kowa Co. Ltd. | Derives pyrimidiniques |
| WO1999049866A1 (fr) | 1998-03-31 | 1999-10-07 | Tanabe Seiyaku Co., Ltd. | Agents prophylactiques/therapeutiques contre les troubles urinaires |
| CA2315614C (fr) | 1999-07-29 | 2004-11-02 | Pfizer Inc. | Pyrazoles |
| DE60025803T2 (de) * | 2000-01-25 | 2006-11-02 | F. Hoffmann-La Roche Ag | Herstellung von sulfonamiden |
| US6387915B2 (en) | 2000-05-31 | 2002-05-14 | Pfizer Inc. | Isoxazole-sulfonamide endothelin antagonists |
| US6670362B2 (en) | 2000-09-20 | 2003-12-30 | Pfizer Inc. | Pyridazine endothelin antagonists |
| EP2399903A1 (fr) | 2002-05-24 | 2011-12-28 | Millennium Pharmaceuticals, Inc. | Inhibiteurs de CCR9 et leurs procédés dýutilisation |
| WO2011078143A1 (fr) * | 2009-12-22 | 2011-06-30 | 塩野義製薬株式会社 | Dérivés de pyrimidine et composition pharmaceutique les contenant |
| WO2014192903A1 (fr) | 2013-05-31 | 2014-12-04 | 興和株式会社 | Nouvelle forme de composé pyrimidinique ayant une structure dibenzylamine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU751007A1 (ru) * | 1979-02-05 | 1990-11-07 | Институт биохимии АН ЛитССР | 2- @ N-[4-(3,3-Диметилтриазено)-бензолсульфонил]-амидо @ -4,6-диметилпиримидин, про вл ющий противовоспалительное действие |
| HU177184B (en) * | 1979-05-11 | 1981-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 2,3- and 3,4-disubstituted-hexahydro-pyrimido-square bracket-1,2-a-square bracket closed-asepines |
| FI64367C (fi) * | 1980-02-26 | 1986-08-05 | Orion Yhtymae Oy | Foerfarande foer framstaellning av alfa-form av prazosinhydroklorid |
| US4490374A (en) * | 1982-09-30 | 1984-12-25 | Ortho Pharmaceutical Corporation | 5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use |
| US4612376A (en) * | 1983-03-25 | 1986-09-16 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent |
| SU1433958A1 (ru) * | 1985-07-26 | 1988-10-30 | Институт Органического Синтеза Ан Латвсср | 2-Оксо-4-(о-дифторметилтиофенил)-5-метоксикарбонил-6-метил-1,2,3,4-тетрагидропиримидин, обладающий коронарорасшир ющим действием |
| SU1533693A1 (ru) * | 1987-05-14 | 1990-01-07 | 1-Й Московский Медицинский Институт Им.И.М.Сеченова | Способ лечени больных инфарктом миокарда |
| TW270116B (fr) * | 1991-04-25 | 1996-02-11 | Hoffmann La Roche | |
| RU2086544C1 (ru) * | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| DE4128116C1 (fr) * | 1991-08-24 | 1993-02-25 | Schmidt Reuter Ingenieurgesellschaft Mbh & Partner Kg, 5000 Koeln, De | |
| TW287160B (fr) * | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| TW394761B (en) * | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
| IL111959A (en) * | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
| EP0801062B1 (fr) * | 1994-12-28 | 2003-04-23 | Kowa Co. Ltd. | Derives pyrimidiniques |
-
1996
- 1996-09-04 US US09/029,244 patent/US5883092A/en not_active Expired - Fee Related
- 1996-09-04 EP EP96929512A patent/EP0852226B1/fr not_active Expired - Lifetime
- 1996-09-04 KR KR10-1998-0701163A patent/KR100453097B1/ko not_active Expired - Fee Related
- 1996-09-04 AT AT96929512T patent/ATE254607T1/de not_active IP Right Cessation
- 1996-09-04 ES ES96929512T patent/ES2210384T3/es not_active Expired - Lifetime
- 1996-09-04 WO PCT/JP1996/002494 patent/WO1997009318A1/fr not_active Ceased
- 1996-09-04 AU AU68890/96A patent/AU703892B2/en not_active Ceased
- 1996-09-04 RU RU98106104/04A patent/RU2170734C2/ru not_active IP Right Cessation
- 1996-09-04 CA CA002230516A patent/CA2230516C/fr not_active Expired - Fee Related
- 1996-09-04 PT PT96929512T patent/PT852226E/pt unknown
- 1996-09-04 CN CN96196812A patent/CN1105711C/zh not_active Expired - Fee Related
- 1996-09-04 DE DE69630799T patent/DE69630799T2/de not_active Expired - Lifetime
- 1996-09-04 HU HU9903526A patent/HUP9903526A3/hu unknown
-
1998
- 1998-03-05 NO NO19980959A patent/NO310235B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0852226A4 (fr) | 1998-09-02 |
| EP0852226A1 (fr) | 1998-07-08 |
| WO1997009318A1 (fr) | 1997-03-13 |
| DE69630799D1 (en) | 2003-12-24 |
| KR19990037684A (ko) | 1999-05-25 |
| KR100453097B1 (ko) | 2004-12-31 |
| AU6889096A (en) | 1997-03-27 |
| ES2210384T3 (es) | 2004-07-01 |
| HUP9903526A2 (hu) | 2000-06-28 |
| HUP9903526A3 (en) | 2000-07-28 |
| US5883092A (en) | 1999-03-16 |
| CA2230516A1 (fr) | 1997-03-13 |
| PT852226E (pt) | 2004-03-31 |
| RU2170734C2 (ru) | 2001-07-20 |
| EP0852226B1 (fr) | 2003-11-19 |
| NO980959L (no) | 1998-03-05 |
| DE69630799T2 (de) | 2004-08-12 |
| HK1016591A1 (en) | 1999-11-05 |
| CA2230516C (fr) | 2008-11-18 |
| ATE254607T1 (de) | 2003-12-15 |
| NO980959D0 (no) | 1998-03-05 |
| CN1196051A (zh) | 1998-10-14 |
| CN1105711C (zh) | 2003-04-16 |
| AU703892B2 (en) | 1999-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |