ZA200300167B - Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme. - Google Patents
Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme. Download PDFInfo
- Publication number
- ZA200300167B ZA200300167B ZA200300167A ZA200300167A ZA200300167B ZA 200300167 B ZA200300167 B ZA 200300167B ZA 200300167 A ZA200300167 A ZA 200300167A ZA 200300167 A ZA200300167 A ZA 200300167A ZA 200300167 B ZA200300167 B ZA 200300167B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound according
- arylalkyl
- aryl
- pyrrolidine
- Prior art date
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- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 title claims description 15
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 title claims description 15
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 104
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- -1 arylcarbonylalkyl Chemical group 0.000 claims description 36
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
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- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
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- VTHPWPGJXZCYHN-GGAORHGYSA-N 4-[methyl-[2-[methyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetyl]amino]benzoic acid Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC(=O)N(C)C1=CC=C(C(O)=O)C=C1 VTHPWPGJXZCYHN-GGAORHGYSA-N 0.000 claims description 2
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- RPXYGMUPGVJLRX-NOZRDPDXSA-N methyl 4-[[2-[[(2s,4r)-4-acetylsulfanyl-1-naphthalen-2-ylsulfonylpyrrolidine-2-carbonyl]amino]acetyl]-methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N(C)C(=O)CNC(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@H](SC(C)=O)C1 RPXYGMUPGVJLRX-NOZRDPDXSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- 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
- A61P9/06—Antiarrhythmics
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
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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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no 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
- C07D207/12—Oxygen or sulfur atoms
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no 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
- C07D207/16—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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Toxicology (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00114947 | 2000-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300167B true ZA200300167B (en) | 2004-04-07 |
Family
ID=8169224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300167A ZA200300167B (en) | 2000-07-19 | 2003-01-07 | Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6541638B2 (ja) |
| EP (1) | EP1303485A1 (ja) |
| JP (1) | JP4068452B2 (ja) |
| KR (1) | KR100568841B1 (ja) |
| CN (1) | CN1620433A (ja) |
| AR (1) | AR033984A1 (ja) |
| AU (1) | AU2001270627A1 (ja) |
| BR (1) | BR0112580A (ja) |
| CA (1) | CA2414311C (ja) |
| GT (1) | GT200100145A (ja) |
| MX (1) | MXPA03000223A (ja) |
| PA (1) | PA8522501A1 (ja) |
| PE (1) | PE20020294A1 (ja) |
| UY (1) | UY26847A1 (ja) |
| WO (1) | WO2002006222A1 (ja) |
| ZA (1) | ZA200300167B (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7847901A (en) * | 2000-07-19 | 2002-02-05 | Hoffmann La Roche | Pyrrolidine derivatives as metalloprotease inhibitors |
| CA2430978C (en) * | 2000-12-28 | 2012-05-15 | Daiichi Pharmaceutical Co., Ltd. | Vla-4 inhibitors |
| DE60336986D1 (de) | 2002-03-05 | 2011-06-16 | Sumitomo Chemical Co | Verfahren zur herstellung von biarylverbindungen |
| WO2004089294A2 (en) | 2003-04-04 | 2004-10-21 | Incyte Corporation | Compositions, methods and kits relating to her-2 cleavage |
| MXPA05010883A (es) | 2003-04-10 | 2006-01-23 | Amgen Inc | Derivados de amina ciclica y su uso en el tratamiento de trastornos inflamatorios relacionados mediados por bradiquinina. |
| MXPA05010884A (es) | 2003-04-10 | 2007-01-15 | Amgen Inc | Compuestos biciclicos que tienen afinidad por receptores de bradicinina y composiciones farmaceuticas de los mismos. |
| CA2529314A1 (en) | 2003-06-20 | 2005-07-07 | Amgen Inc. | Piperazine derivatives and methods of use |
| JP4676884B2 (ja) | 2003-07-24 | 2011-04-27 | 第一三共株式会社 | シクロヘキサンカルボン酸類 |
| CN1294120C (zh) * | 2003-10-21 | 2007-01-10 | 山东大学 | 吡咯烷类基质金属蛋白酶抑制剂及其应用 |
| JP2009533420A (ja) * | 2006-04-13 | 2009-09-17 | アクテリオン ファーマシューティカルズ リミテッド | 早期特発性肺線維症の治療 |
| ES2350548B1 (es) * | 2009-06-25 | 2011-09-29 | Institut Univ. De Ciència I Tecnologia, S.A. | N-fenil-1-sulfonil-2-pirrolidinacarboxamidas para la identificacion de actividad biologica y farmacologica. |
| EP2730571A1 (en) * | 2012-11-12 | 2014-05-14 | Universitat De Barcelona | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| WO2019009317A1 (ja) * | 2017-07-05 | 2019-01-10 | 日産化学株式会社 | ベンジル化合物 |
| CN110078593A (zh) * | 2018-11-15 | 2019-08-02 | 南通正达农化有限公司 | 一种苹果蠹蛾性信息素的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1283906C (en) * | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| AU644008B2 (en) * | 1990-08-10 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Beta-lactam compounds, and their production and use |
| JP3091297B2 (ja) * | 1992-01-10 | 2000-09-25 | 住友製薬株式会社 | ピロリジン誘導体およびその製造方法 |
| AU741893B2 (en) * | 1996-08-28 | 2001-12-13 | Procter & Gamble Company, The | Substituted cyclic amine metalloprotease inhibitors |
| BR9712792A (pt) * | 1996-08-28 | 1999-12-14 | Procter & Gamble | Inibidores de metaloprotease bidentada. |
| AU736136B2 (en) * | 1997-07-10 | 2001-07-26 | Merck Sharp & Dohme Corp. | Crystalline forms of antibiotic side chain intermediates |
| CN1163494C (zh) * | 1998-05-01 | 2004-08-25 | 京都药品工业株式会社 | 碳青霉烯衍生物、其用途及其中间体化合物 |
-
2001
- 2001-07-10 MX MXPA03000223A patent/MXPA03000223A/es not_active Application Discontinuation
- 2001-07-10 WO PCT/EP2001/007950 patent/WO2002006222A1/en not_active Application Discontinuation
- 2001-07-10 KR KR1020037000781A patent/KR100568841B1/ko not_active IP Right Cessation
- 2001-07-10 BR BR0112580-0A patent/BR0112580A/pt not_active IP Right Cessation
- 2001-07-10 EP EP01949485A patent/EP1303485A1/en not_active Withdrawn
- 2001-07-10 CA CA002414311A patent/CA2414311C/en not_active Expired - Fee Related
- 2001-07-10 AU AU2001270627A patent/AU2001270627A1/en not_active Abandoned
- 2001-07-10 CN CNA018130232A patent/CN1620433A/zh active Pending
- 2001-07-10 JP JP2002512128A patent/JP4068452B2/ja not_active Expired - Fee Related
- 2001-07-16 PA PA20018522501A patent/PA8522501A1/es unknown
- 2001-07-16 PE PE2001000711A patent/PE20020294A1/es not_active Application Discontinuation
- 2001-07-17 UY UY26847A patent/UY26847A1/es not_active Application Discontinuation
- 2001-07-17 US US09/907,135 patent/US6541638B2/en not_active Expired - Fee Related
- 2001-07-17 AR ARP010103416A patent/AR033984A1/es unknown
- 2001-07-18 GT GT200100145A patent/GT200100145A/es unknown
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2003
- 2003-01-07 ZA ZA200300167A patent/ZA200300167B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP4068452B2 (ja) | 2008-03-26 |
| MXPA03000223A (es) | 2003-06-06 |
| PE20020294A1 (es) | 2002-04-17 |
| CA2414311C (en) | 2008-01-08 |
| GT200100145A (es) | 2002-05-16 |
| EP1303485A1 (en) | 2003-04-23 |
| AR033984A1 (es) | 2004-01-21 |
| US6541638B2 (en) | 2003-04-01 |
| JP2004504297A (ja) | 2004-02-12 |
| CN1620433A (zh) | 2005-05-25 |
| US20020049243A1 (en) | 2002-04-25 |
| BR0112580A (pt) | 2003-06-17 |
| CA2414311A1 (en) | 2002-01-24 |
| AU2001270627A1 (en) | 2002-01-30 |
| KR20030016416A (ko) | 2003-02-26 |
| UY26847A1 (es) | 2002-01-31 |
| WO2002006222A1 (en) | 2002-01-24 |
| KR100568841B1 (ko) | 2006-04-10 |
| PA8522501A1 (es) | 2002-09-17 |
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