RU2002128007A - Содержащие гетероциклическую боковую цепь n-замещенные ингибиторы металлопротеазы - Google Patents
Содержащие гетероциклическую боковую цепь n-замещенные ингибиторы металлопротеазыInfo
- Publication number
- RU2002128007A RU2002128007A RU2002128007/04A RU2002128007A RU2002128007A RU 2002128007 A RU2002128007 A RU 2002128007A RU 2002128007/04 A RU2002128007/04 A RU 2002128007/04A RU 2002128007 A RU2002128007 A RU 2002128007A RU 2002128007 A RU2002128007 A RU 2002128007A
- Authority
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- Prior art keywords
- group
- alkyl
- heterocycloalkyl
- compound according
- heteroalkyl
- Prior art date
Links
- 239000003475 metalloproteinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- -1 halsgenalkyl Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 238000009776 industrial production Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (13)
1. Соединение, имеющее структуру в соответствии с формулой (I)
отличающееся тем, что (A) R1 выбирают из -ОН и -NHOH;
(B) R2 выбирают из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкилалкил, гетероциклоалкилалкил, арилалкил и гетероарилалкил, или R2 может быть связан с А, как описано в (D);
(C) R3 выбирают из группы, включающей алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкил, гетероциклоалкил, арилалкил и гетероарилалкил;
D) А означает замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле, из которых 1-3 являются гетероатомами, или А связан с R2, где вместе они образуют замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле, из которых 1-3 являются гетероатомами;
(Е) n = 0-4;
(F) Е выбирают из группы, включающей ковалентную связь, С1-С4-алкил, -С(=O)-, -С (=O)O-, C(=O)N(R4)-, -SO2 или С(=S)N(R4)-, где R4 выбирают из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкил, гетероциклоалкил, арил, арилалкил, гетероарил и гетероарилалкил, или R4 и Х соединены с образованием цикла, указанного в (G) (2);
(G) (1) X выбирают из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галсгеналкил, арил, арилалкил, гетероарил, гетероарилалкил, циклоалкил и гетероциклоалкил, или (2) Х и R4 соединены, образуя замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле, из которых 1-3 являются гетероатомами;
(Н) G выбирают из группы, включающей: -S-, -О-, -N(R5)-, -C(R5)=C(R5’)-, -N=C(R5)- и -N=N-, где каждый из R5 и R5’ независимо выбирают из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, арил, гетероарил, циклоалкил и гетероциклоалкил,
(I) G’ выбирают из группы, включающей -S-, -О-, -N(R6)-, -C(R6)=C(R6’)-, -N=C(R6)- и -N=N-, где каждый из R6 и R6’ независимо выбирают из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, арил, гетероарил, циклоалкил и гетероциклоалкил;
(J) М выбирают из –СН- и -N-;
(К) Z означает (CR7R7’)a-L-R8, где (1) а = 0-4, (2) каждый из R7 и R7’ независимо выбирают из группы, включающей: водород, алкил, алкенил, алкинил, арил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил, галоген, галогеналкил, гидрокси и алкокси, (3) L выбирают из группы, включающей ковалентную связь, -О-, -SOb-, -С(=O)-, C(=O)N(R9)-, -N(R9)- и -N(R9)С(=O)-; где b = 0-2 и R9 выбирают из группы, включающей водород, алкил, алкенил, алкинил, арил, гетероарил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил и галогеналкил, или R7 и R9, вместе с атомами, к которым они химически присоединены, объединяются, образуя необязательно замещенный гетероцикл, содержащий 5-8 атомов, из которых 1-3 являются гетероатомами, и (4) R8 выбирают из группы, включающей водород, алкил, алкенил, алкинил, галоген, гетероалкил, галогеналкил, арил, гетероарил, циклоалкил и гетероциклоалкил, или R8 и R9, вместе с атомами, к которым они химически присоединены, объединяются, образуя необязательно замещенный гетероцикл, содержащий 5-8 атомов, из которых 1-3 являются гетероатомами,
или оптический изомер, диастереомер или энантиомер соединения формулы (I), или их фармацевтически приемлемая соль, или биогидролизуемый амид, сложный эфир или имид.
2. Соединение по п.1, отличающееся тем, что А и R2 не объединяются с образованием цикла и, отличающееся тем, что А означает замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле и 1-3 гетероатомами.
3. Соединение по п.1, отличающееся тем, что А и R2 вместе образуют замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле и 1-3 гетероатомами.
4. Соединение по любому из пп.1, 2 или 3, отличающееся тем, что Х выбирают из группы, включающей водород, алкил, гетероалкил, арил, арилалкил, гетероарил, гетероарилалкил, циклоалкил или гетероциклоалкил.
5. Соединение по любому из пп.1, 2 или 3, отличающееся тем, что Х и R4 объединяются, образуя замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в цикле и 1-3 гетероатомами в цикле.
6. Соединение по любому из предшествующих пунктов, отличающееся тем, что G выбирают из –S- и -СН=СН-, G’ выбирают из –S- и -СН=СН-, и М означает -СН-.
7. Соединение по любому из предшествующих пунктов, отличающееся тем, что Е выбирают из группы, включающей (ковалентную) связь, С1-С4-алкил, -С(=О), -С(=О)О-, -C(=О)N(R4)- и -SO2-.
8. Соединение по любому из предшествующих пунктов, отличающееся тем, что R3 выбирают из группы, включающей алкил, гетероалкил, гетероциклоалкилалкил, арилалкил и гетероарилалкил.
9. Соединение по любому из предшествующих пунктов, отличающееся тем, что R2 означает водород или алкил и n = 0 или 1.
10. Фармацевтическая композиция, включающая (a) безопасное и эффективное количество соединения по любому из предшествующих пунктов и b) фармацевтически приемлемый носитель.
11. Соединение по любому из пп.1-9, применимое для промышленного получения лекарственного средства для лечения болезни, связанной с нежелательной активностью металлопротеаз в организме млекопитающего.
12. Соединение по п.11, отличающееся тем, что болезнь представляет собой артрит и выбрана из группы, включающей остеоартрит и ревматсидный артрит.
13. Соединение по п.11, отличающееся тем, что нарушение представляет собой раковую опухоль, и лечение предупреждает или останавливает рост опухоли и метастазов.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19130200P | 2000-03-21 | 2000-03-21 | |
| US60/191,302 | 2000-03-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002128007A true RU2002128007A (ru) | 2004-02-27 |
| RU2245876C2 RU2245876C2 (ru) | 2005-02-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002128007/04A RU2245876C2 (ru) | 2000-03-21 | 2001-03-02 | Производные сульфонамидов и фармацевтическая композиция на их основе |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6949545B2 (ru) |
| EP (1) | EP1265864A1 (ru) |
| JP (1) | JP2003528080A (ru) |
| KR (1) | KR20020081465A (ru) |
| CN (1) | CN1425004A (ru) |
| AR (1) | AR030197A1 (ru) |
| AU (1) | AU2001245891A1 (ru) |
| BR (1) | BR0109328A (ru) |
| CA (1) | CA2404131A1 (ru) |
| CZ (1) | CZ20023145A3 (ru) |
| HU (1) | HUP0300235A2 (ru) |
| IL (1) | IL151125A0 (ru) |
| MA (1) | MA26884A1 (ru) |
| MX (1) | MXPA02009311A (ru) |
| NO (1) | NO20024520L (ru) |
| NZ (1) | NZ520657A (ru) |
| PE (1) | PE20011137A1 (ru) |
| PL (1) | PL365444A1 (ru) |
| RU (1) | RU2245876C2 (ru) |
| SK (1) | SK12842002A3 (ru) |
| WO (1) | WO2001070691A1 (ru) |
| ZA (1) | ZA200206298B (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1249239B1 (en) * | 1999-12-28 | 2008-05-21 | Teikoku Seiyaku Co., Ltd. | Antipruritic agents for external use |
| JP2003528079A (ja) * | 2000-03-21 | 2003-09-24 | ザ プロクター アンド ギャンブル カンパニー | 複素環式側鎖含有メタロプロテアーゼ阻害剤 |
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2001
- 2001-03-02 SK SK1284-2002A patent/SK12842002A3/sk unknown
- 2001-03-02 AU AU2001245891A patent/AU2001245891A1/en not_active Abandoned
- 2001-03-02 CZ CZ20023145A patent/CZ20023145A3/cs unknown
- 2001-03-02 PL PL01365444A patent/PL365444A1/xx not_active Application Discontinuation
- 2001-03-02 IL IL15112501A patent/IL151125A0/xx unknown
- 2001-03-02 CA CA002404131A patent/CA2404131A1/en not_active Abandoned
- 2001-03-02 NZ NZ520657A patent/NZ520657A/en unknown
- 2001-03-02 BR BR0109328-2A patent/BR0109328A/pt not_active IP Right Cessation
- 2001-03-02 JP JP2001568903A patent/JP2003528080A/ja not_active Withdrawn
- 2001-03-02 WO PCT/US2001/008931 patent/WO2001070691A1/en not_active Ceased
- 2001-03-02 HU HU0300235A patent/HUP0300235A2/hu unknown
- 2001-03-02 KR KR1020027012313A patent/KR20020081465A/ko not_active Ceased
- 2001-03-02 RU RU2002128007/04A patent/RU2245876C2/ru not_active IP Right Cessation
- 2001-03-02 MX MXPA02009311A patent/MXPA02009311A/es unknown
- 2001-03-02 CN CN01806655A patent/CN1425004A/zh active Pending
- 2001-03-02 EP EP01918867A patent/EP1265864A1/en not_active Withdrawn
- 2001-03-20 AR ARP010101310A patent/AR030197A1/es not_active Application Discontinuation
- 2001-03-21 PE PE2001000265A patent/PE20011137A1/es not_active Application Discontinuation
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2004
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| ZA200206298B (en) | 2003-04-11 |
| WO2001070691A1 (en) | 2001-09-27 |
| KR20020081465A (ko) | 2002-10-26 |
| NO20024520D0 (no) | 2002-09-20 |
| MXPA02009311A (es) | 2003-03-12 |
| US20040127498A1 (en) | 2004-07-01 |
| RU2245876C2 (ru) | 2005-02-10 |
| MA26884A1 (fr) | 2004-12-20 |
| CN1425004A (zh) | 2003-06-18 |
| US20030139414A1 (en) | 2003-07-24 |
| CA2404131A1 (en) | 2001-09-27 |
| HUP0300235A2 (hu) | 2003-08-28 |
| JP2003528080A (ja) | 2003-09-24 |
| AR030197A1 (es) | 2003-08-13 |
| AU2001245891A1 (en) | 2001-10-03 |
| EP1265864A1 (en) | 2002-12-18 |
| NO20024520L (no) | 2002-09-20 |
| PE20011137A1 (es) | 2001-12-04 |
| NZ520657A (en) | 2004-11-26 |
| PL365444A1 (en) | 2005-01-10 |
| US6949545B2 (en) | 2005-09-27 |
| SK12842002A3 (sk) | 2003-02-04 |
| IL151125A0 (en) | 2003-04-10 |
| CZ20023145A3 (cs) | 2003-01-15 |
| BR0109328A (pt) | 2003-06-10 |
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