NO321026B1 - Nitrogen-inneholdende heterosykliske karboksamidderivater eller salter derav - Google Patents
Nitrogen-inneholdende heterosykliske karboksamidderivater eller salter derav Download PDFInfo
- Publication number
- NO321026B1 NO321026B1 NO20010836A NO20010836A NO321026B1 NO 321026 B1 NO321026 B1 NO 321026B1 NO 20010836 A NO20010836 A NO 20010836A NO 20010836 A NO20010836 A NO 20010836A NO 321026 B1 NO321026 B1 NO 321026B1
- Authority
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- Norway
- Prior art keywords
- group
- virus
- ring
- nitrogen
- containing heterocyclic
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 36
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title abstract description 7
- 241000712461 unidentified influenza virus Species 0.000 claims abstract description 17
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 Nitrogen-containing heterocyclic carboxamide Chemical class 0.000 claims description 41
- 241000700605 Viruses Species 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003443 antiviral agent Substances 0.000 claims description 8
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- 231100000283 hepatitis Toxicity 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 241000709661 Enterovirus Species 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 241000711404 Avian avulavirus 1 Species 0.000 claims description 3
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- 241001631646 Papillomaviridae Species 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 206010022000 influenza Diseases 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 210000003501 vero cell Anatomy 0.000 description 4
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- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 108010072147 type V-S pancreatic trypsin Proteins 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229960003636 vidarabine Drugs 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
-
- 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
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
Landscapes
- 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)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25044198 | 1998-08-20 | ||
| JP14592299 | 1999-05-26 | ||
| PCT/JP1999/004429 WO2000010569A1 (en) | 1998-08-20 | 1999-08-18 | Nitrogenous heterocyclic carboxamide derivatives or salts thereof and antiviral agents containing both |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010836D0 NO20010836D0 (no) | 2001-02-19 |
| NO20010836L NO20010836L (no) | 2001-04-18 |
| NO321026B1 true NO321026B1 (no) | 2006-02-27 |
Family
ID=26476908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010836A NO321026B1 (no) | 1998-08-20 | 2001-02-19 | Nitrogen-inneholdende heterosykliske karboksamidderivater eller salter derav |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US6787544B2 (cs) |
| EP (1) | EP1112743B1 (cs) |
| JP (1) | JP3453362B2 (cs) |
| KR (1) | KR100585240B1 (cs) |
| CN (2) | CN1275947C (cs) |
| AT (1) | ATE376418T1 (cs) |
| AU (1) | AU756635B2 (cs) |
| BR (1) | BRPI9913097B8 (cs) |
| CA (1) | CA2339272C (cs) |
| CY (1) | CY1107001T1 (cs) |
| CZ (1) | CZ301763B6 (cs) |
| DE (1) | DE69937405T2 (cs) |
| DK (1) | DK1112743T3 (cs) |
| ES (1) | ES2296399T3 (cs) |
| HU (1) | HU227475B1 (cs) |
| ID (1) | ID28806A (cs) |
| IL (1) | IL141150A (cs) |
| MX (1) | MXPA01001843A (cs) |
| NO (1) | NO321026B1 (cs) |
| NZ (1) | NZ509748A (cs) |
| PL (1) | PL200955B1 (cs) |
| PT (1) | PT1112743E (cs) |
| RU (1) | RU2224520C2 (cs) |
| TR (1) | TR200100574T2 (cs) |
| WO (1) | WO2000010569A1 (cs) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE294185T1 (de) * | 2000-02-16 | 2005-05-15 | Toyama Chemical Co Ltd | Neue pyrazin-derivate oder salze davon, pharmazeutische zusammensetzungen, die die derivate oder deren salze enthalten und intermediäre zur herstellung der derivate |
| BR0211900A (pt) * | 2001-08-14 | 2004-08-24 | Toyama Chemical Co Ltd | Método para inibição do desenvolvimento de vìrus e/ou virucida, análogos de nucleotìdeo de pirazina e de nucleosìdeo de pirazina, precursor do inibidor da polimerase de rna, inibidor da polimerase de rna, método para tratar pacientes infectados por vìrus, e, usos de um análogo de nucleotìdeo de pirazina ou um sal deste e de um análogo de nucleosìdeo de pirazina ou um sal deste |
| CN102229605B (zh) | 2001-10-26 | 2015-01-14 | Msd意大利有限公司 | 关于hiv整合酶的n-取代的羟基嘧啶酮甲酰胺抑制剂 |
| ATE355064T1 (de) | 2001-10-26 | 2006-03-15 | Angeletti P Ist Richerche Bio | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| JP4200758B2 (ja) * | 2002-12-26 | 2008-12-24 | 株式会社日立ハイテクノロジーズ | パネルの樹脂塗布方法、ディスプレイ用パネルの製造方法及び樹脂塗布装置 |
| EP1691747B1 (en) * | 2003-11-13 | 2012-05-23 | CardioPolymers, Inc. | Control of cardiac arrhythmias by modification of neuronal conduction within fat pads of the heart |
| TWI355894B (en) * | 2003-12-19 | 2012-01-11 | Du Pont | Herbicidal pyrimidines |
| CN1560035A (zh) * | 2004-03-12 | 2005-01-05 | 沈阳药科大学 | 5－羟基吲哚－3－羧酸脂类衍生物 |
| KR100700676B1 (ko) * | 2005-06-24 | 2007-03-28 | (주) 비엔씨바이오팜 | 6―（4―치환된―아닐리노）피리미딘 유도체, 그 제조방법및 이를 포함하는 항바이러스용 약학적 조성물 |
| PL2022786T3 (pl) | 2006-05-31 | 2012-06-29 | Toyama Chemical Co Ltd | Środek przeciwko wirusowi pryszczycy dla zwierząt należących do rodziny Suidae lub owiec i sposób zapobiegania lub leczenia pryszczycy u zwierząt należących do rodziny Suidae lub owiec |
| ZA200905536B (en) * | 2007-02-16 | 2010-10-27 | Toyama Chemical Co Ltd | Pharmaceutical composition comprising pyrazine derivative, and method of using pyrazine derivative in combination |
| CN101289455B (zh) * | 2007-04-17 | 2010-11-10 | 靳广毅 | 一种抗流感病毒前体药及其应用 |
| RU2527766C2 (ru) * | 2009-03-13 | 2014-09-10 | Тояма Кемикал Ко., Лтд. | Таблетки и гранулированные порошки, содержащие 6-фтор-3-гидрокси-2-пиразинкарбоксамид |
| JP5739618B2 (ja) * | 2009-03-18 | 2015-06-24 | 富山化学工業株式会社 | ３−ヒドロキシ−２−ピラジンカルボキサミドの製造法 |
| US20130217708A1 (en) * | 2010-09-30 | 2013-08-22 | Toyama Chemical Co., Ltd. | Meglumine salt of 6-fluoro-3-hydroxy-2-pyrazine carboxamide |
| PH12013500604A1 (en) * | 2010-09-30 | 2013-05-06 | Toyama Chemical Co Ltd | Sodium salt of 6-fluoro-3-hydroxy-2-pyrazine carboxamide |
| WO2012063931A1 (ja) * | 2010-11-12 | 2012-05-18 | 富士フイルム株式会社 | ピラジノ〔２，３－ｄ〕イソオキサゾール誘導体 |
| CN102850282B (zh) * | 2011-07-01 | 2015-09-16 | 中国人民解放军军事医学科学院毒物药物研究所 | 3-取代氧基-2-吡嗪甲酰胺类化合物及其用途 |
| CN102846617B (zh) * | 2011-07-01 | 2016-01-13 | 中国人民解放军军事医学科学院毒物药物研究所 | 3－(丁基氧基)－2－吡嗪甲酰氨的制备方法和用途 |
| WO2013004092A1 (zh) * | 2011-07-01 | 2013-01-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 3-氧代-3，4-二氢-2-吡嗪甲酰氨类衍生物、其药物组合物、其制备方法及用途 |
| CN102617491B (zh) * | 2011-07-01 | 2015-05-06 | 中国人民解放军军事医学科学院毒物药物研究所 | 3-氧代-3,4-二氢-2-吡嗪甲酰氨类衍生物、其药物组合物、其制备方法及用途 |
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| WO2013180149A1 (ja) * | 2012-05-30 | 2013-12-05 | 富山化学工業株式会社 | 重水素化含窒素複素環カルボキサミド誘導体またはその塩 |
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| CN106588786B (zh) * | 2015-10-14 | 2019-03-08 | 山东省药学科学院 | 一种高纯度法匹拉韦杂质的制备方法 |
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| CN106083745B (zh) * | 2016-08-15 | 2018-08-21 | 山东百诺医药股份有限公司 | 6-氟-3-羟基-2-吡嗪酰胺的合成方法 |
| CN107226794A (zh) * | 2017-07-17 | 2017-10-03 | 郑州大学 | 一种法匹拉韦的合成方法 |
| BR112020009101A2 (pt) | 2017-12-28 | 2020-10-20 | Fujifilm Toyama Chemical Co., Ltd. | método para produção de formulação congelada |
| WO2020138067A1 (ja) | 2018-12-25 | 2020-07-02 | 富士フイルム富山化学株式会社 | ピラジン誘導体と細胞内におけるピラジン誘導体リボース三リン酸体の量を増加させる化合物とを組み合わせてなるｒｎａウイルス感染症治療剤 |
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| US3631036A (en) * | 1969-11-04 | 1971-12-28 | American Home Prod | 5-amino-2 6-substituted-7h-pyrrolo(2 3-d) pyrimidines and related compounds |
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-
1999
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- 1999-08-18 MX MXPA01001843A patent/MXPA01001843A/es active IP Right Grant
- 1999-08-18 PT PT99938504T patent/PT1112743E/pt unknown
- 1999-08-18 RU RU2001104536/15A patent/RU2224520C2/ru active
- 1999-08-18 BR BRPI9913097A patent/BRPI9913097B8/pt not_active IP Right Cessation
- 1999-08-18 CN CNB2004100325508A patent/CN1275947C/zh not_active Expired - Lifetime
- 1999-08-18 AT AT99938504T patent/ATE376418T1/de active
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- 1999-08-18 PL PL346172A patent/PL200955B1/pl unknown
- 1999-08-18 AU AU53004/99A patent/AU756635B2/en not_active Expired
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- 1999-08-18 HU HU0103453A patent/HU227475B1/hu unknown
- 1999-08-18 NZ NZ509748A patent/NZ509748A/xx not_active IP Right Cessation
- 1999-08-18 WO PCT/JP1999/004429 patent/WO2000010569A1/ja not_active Ceased
- 1999-08-18 ID IDW20010396A patent/ID28806A/id unknown
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- 1999-08-18 KR KR1020017001690A patent/KR100585240B1/ko not_active Expired - Lifetime
- 1999-08-18 JP JP2000565890A patent/JP3453362B2/ja not_active Expired - Lifetime
- 1999-08-18 DK DK99938504T patent/DK1112743T3/da active
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2001
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2010
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