RU2001129708A - Производные дибензоазулена, предназначенные для лечения тромбоза, остеопороза, артериосклероза - Google Patents
Производные дибензоазулена, предназначенные для лечения тромбоза, остеопороза, артериосклерозаInfo
- Publication number
- RU2001129708A RU2001129708A RU2001129708/04A RU2001129708A RU2001129708A RU 2001129708 A RU2001129708 A RU 2001129708A RU 2001129708/04 A RU2001129708/04 A RU 2001129708/04A RU 2001129708 A RU2001129708 A RU 2001129708A RU 2001129708 A RU2001129708 A RU 2001129708A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- solvates
- compounds
- atoms
- physiologically acceptable
- Prior art date
Links
- 208000007536 Thrombosis Diseases 0.000 title claims 3
- 206010003210 Arteriosclerosis Diseases 0.000 title claims 2
- 208000001132 Osteoporosis Diseases 0.000 title claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 230000009977 dual effect Effects 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- -1 1,4,5,6-tetrahydropyrimidin-2-ylamino Chemical group 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- GHNLFEZEYKRRQL-UHFFFAOYSA-N C1=C2CC(C3=4)=CC=CC=4C(CC(=O)O)CC3CC2=CC=C1OCCCNC1=NCCCN1 Chemical compound C1=C2CC(C3=4)=CC=CC=4C(CC(=O)O)CC3CC2=CC=C1OCCCNC1=NCCCN1 GHNLFEZEYKRRQL-UHFFFAOYSA-N 0.000 claims 1
- CCOMBIIAONTHLJ-UHFFFAOYSA-N C1=C2CC(C3=4)=CC=CC=4CC(C(=O)O)=C3CC2=CC=C1OCCCNC1=CC=CC=N1 Chemical compound C1=C2CC(C3=4)=CC=CC=4CC(C(=O)O)=C3CC2=CC=C1OCCCNC1=CC=CC=N1 CCOMBIIAONTHLJ-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 102100025306 Integrin alpha-IIb Human genes 0.000 claims 1
- 101710149643 Integrin alpha-IIb Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000002491 angiogenic effect Effects 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- HGLFWLLFPGIKOT-UHFFFAOYSA-N azulene-1-carboxylic acid Chemical compound C1=CC=CC=C2C(C(=O)O)=CC=C21 HGLFWLLFPGIKOT-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229940125798 integrin inhibitor Drugs 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- A61P27/02—Ophthalmic agents
-
- 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
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/10—Antimycotics
-
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
Claims (10)
1. Соединения формулы I
в которой R1 обозначает OR4, NHR4 или NA''2;
R2 представляет собой Н, Hal, NO2, NHR4, NA"2, OR4, SO3R4, SO2R4 или SR4;
R3 обозначает NH2, H2N-C(=NH) или H2N-(C=NH)-NH, где первичные аминогруппы также могут иметь обычные защитные группы аминогруппы, или R5-NH-;
R4 представляет собой Н, А, Ar или Aralk;
R5 обозначает одно- или двухъядерный гетероцикл с 1-4 атомами N, O и/или S, который может быть незамещенным либо моно-, дву- или тризамещенным Hal, A'', -CO-A', ОА', CN, СООА', CONH2, NO2, =NH или =O;
А представляет собой алкил с 1-15 атомами С или циклоалкил с 3-15 атомами С, незамещенный либо моно-, дву- или тризамещенный R6, в котором одна, две либо три метиленовые группы могут быть замещены N, O и/или S;
R6 обозначает Hal, NO2, NHA', NA''2, OA', фенокси, СО-А', SO3А', CN, NHCOA', COOA', CONA'2 или SO2A';
А’ представляет собой Н или алкил с 1-6 атомами С;
А'' обозначает алкил с 1-6 атомами С;
Ar представляет собой одно- или двухъядерную систему ароматического кольца, незамещенную либо моно-, дву- или тризамещенную алкилом с 1-6 атомами С и/или R6 - замещенную одно- либо двухъядерную систему ароматического кольца с 0, 1, 2, 3 или 4 атомами N, O и/или S;
Aralk обозначает аралкилен с 7-14 атомами С, незамещенный или моно-, дву- либо тризамещенный R6, в котором одна, две или три метиленовые группы могут быть замещенными N, O и/или S;
Hal представляет собой F, C1, Br или I;
каждая из переменных m, n независимо от другой равна 0, 1, 2, 3 или 4,
и их физиологически приемлемые соли и сольваты.
2. Энантиомеры или диастереомеры соединений формулы I по п.1.
3. Соединения формулы I по п. 1
а) 8-[3-(пиридин-2-иламино)пропокси]-6,11-дигидро-2Н-дибензо[cd, g]азулен-1-карбоновая кислота,
б) 8-[3-(1,4,5,6-тетрагидропиримидин-2-иламино)пропокси]-2,6,11,11а-тетрагидро-2H-дибензо[cd,g]азулен-1-карбоновая кислота,
в) {8-[3-(1,4,5,6-тетрагидропиримидин-2-иламино)пропокси]-2,6,11,11a-тетрагидро-1H-дибензо[cd,g]азулен-2-ил}уксусная кислота,
и их физиологически приемлемые соли и сольваты.
4. Способ получения соединений формулы I по п.1 и их солей и сольватов, отличающийся тем, что а) путем обработки агентом сольволиза или гидрогенолиза соединение формулы I высвобождают из одной из его производных, содержащих функциональную группу, или б) радикал R1, R2 и/или R3 переводят в другой радикал R1, R2 и/или R3, путем, например, i) введения аминогруппы в реакцию с агентом амидирования и, таким образом, ее перевода в гуанидиновую группу, ii) гидролизования сложного эфира, iii) восстановления карбоновой кислоты до спирта, iv) гидрогенизации гидроксиамидина и, таким образом, его перевода в амидин и/или основание или кислоту формулы I переводят в одну из его (ее) солей.
5. Соединения формулы I по п.1 и их физиологически приемлемые соли и сольваты как антагонисты GPIIb/IIIa, предназначенные для устранения тромбозов, инфаркта миокарда, коронарных болезней и артериосклероза.
6. Соединения формулы I по п.1 и их физиологические соли и сольваты как ингибиторы интегрина αv, предназначенные для снятия патологически ангиогенных расстройств, тромбозов, инфаркта миокарда, коронарных болезней, артериосклероза, опухолей, остеопороза и ревматоидного артрита.
7. Фармацевтический препарат, отличающийся тем, что он содержит по меньшей мере одно соединение формулы I по п.1 и/или одну (один) из его физиологически приемлемых солей или сольватов.
8. Способ изготовления фармацевтического препарата, отличающийся тем, что соединение формулы I по п.1 и/или одну (один) из его физиологически приемлемых солей или сольватов соответствующим образом дозируют в комбинации с по меньшей мере одним твердым, жидким или полужидким связующим или эксципиентом.
9. Применение соединений формулы I по п.1 и их физиологически приемлемых солей и сольватов в качестве терапевтически активных соединений.
10. Применение соединений формулы I по п.1 и их физиологически приемлемых солей и сольватов при изготовлении лекарственного средства, предназначенного для применения в качестве ингибитора интегрина αv.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19916837.7 | 1999-04-14 | ||
| DE19916837A DE19916837A1 (de) | 1999-04-14 | 1999-04-14 | Dibenzoazulenderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2001129708A true RU2001129708A (ru) | 2004-02-27 |
Family
ID=7904536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001129708/04A RU2001129708A (ru) | 1999-04-14 | 2000-04-01 | Производные дибензоазулена, предназначенные для лечения тромбоза, остеопороза, артериосклероза |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6521646B1 (ru) |
| EP (1) | EP1169306A1 (ru) |
| JP (1) | JP2002542231A (ru) |
| KR (1) | KR20010102570A (ru) |
| CN (1) | CN1345312A (ru) |
| AR (1) | AR023496A1 (ru) |
| AU (1) | AU3817400A (ru) |
| BR (1) | BR0009690A (ru) |
| CA (1) | CA2367359A1 (ru) |
| CZ (1) | CZ20013704A3 (ru) |
| DE (1) | DE19916837A1 (ru) |
| HU (1) | HUP0200643A3 (ru) |
| MX (1) | MXPA01010294A (ru) |
| NO (1) | NO20014976D0 (ru) |
| PL (1) | PL350354A1 (ru) |
| RU (1) | RU2001129708A (ru) |
| SK (1) | SK14342001A3 (ru) |
| WO (1) | WO2000063178A1 (ru) |
| ZA (1) | ZA200109343B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2806082B1 (fr) * | 2000-03-07 | 2002-05-17 | Adir | Nouveaux composes bicycliques antagonistes des recepteurs de la vitronectine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1299405B1 (en) * | 2000-06-30 | 2009-05-13 | Dow Global Technologies Inc. | Polycyclic, fused ring compounds, metal complexes and polymerization process |
| US20050107350A1 (en) * | 2003-08-22 | 2005-05-19 | Pharmacia Corporation | Method for the treatment or prevention of bone disorders with a cyclooxygenase-2 inhibitor alone and in combination with a bone disorder treatment agent and compositions therewith |
| CA2568750C (en) | 2004-06-04 | 2014-05-27 | The Scripps Research Institute | Compositions and methods for treatment of neovascular diseases |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3795709A (en) * | 1968-02-07 | 1974-03-05 | Sandoz Ag | Benzobenzazulenes |
| AU5173796A (en) * | 1995-03-09 | 1996-10-02 | Ortho Pharmaceutical Corporation | Substituted dibenz{a,f}azulenes and methods of preparation |
| JP3960482B2 (ja) * | 1995-06-29 | 2007-08-15 | スミスクライン・ビーチャム・コーポレイション | インテグリン受容体アンタゴニスト |
| AP806A (en) * | 1996-03-20 | 2000-01-28 | Aventis Pharma Sa | Tricyclic compounds having activity specific for integrins, particularly avB3 integrins, method for preparing same, intermediates therefor, use of said compounds as drugs, and pharmaceutical compositions containing same. |
| CO4920232A1 (es) * | 1997-01-08 | 2000-05-29 | Smithkline Beecham Corp | Acidos aceticos dibenzo [a,d] cicloheptano con actividad antagonista del receptor de vitronectin |
-
1999
- 1999-04-14 DE DE19916837A patent/DE19916837A1/de not_active Withdrawn
-
2000
- 2000-04-01 CZ CZ20013704A patent/CZ20013704A3/cs unknown
- 2000-04-01 BR BR0009690-3A patent/BR0009690A/pt not_active Application Discontinuation
- 2000-04-01 US US09/958,812 patent/US6521646B1/en not_active Expired - Fee Related
- 2000-04-01 RU RU2001129708/04A patent/RU2001129708A/ru unknown
- 2000-04-01 HU HU0200643A patent/HUP0200643A3/hu unknown
- 2000-04-01 EP EP00917037A patent/EP1169306A1/de not_active Withdrawn
- 2000-04-01 CN CN00805748A patent/CN1345312A/zh active Pending
- 2000-04-01 KR KR1020017011575A patent/KR20010102570A/ko not_active Application Discontinuation
- 2000-04-01 PL PL00350354A patent/PL350354A1/xx unknown
- 2000-04-01 CA CA002367359A patent/CA2367359A1/en not_active Abandoned
- 2000-04-01 MX MXPA01010294A patent/MXPA01010294A/es unknown
- 2000-04-01 SK SK1434-2001A patent/SK14342001A3/sk unknown
- 2000-04-01 AU AU38174/00A patent/AU3817400A/en not_active Abandoned
- 2000-04-01 WO PCT/EP2000/002925 patent/WO2000063178A1/de not_active Application Discontinuation
- 2000-04-01 JP JP2000612271A patent/JP2002542231A/ja active Pending
- 2000-04-14 AR ARP000101738A patent/AR023496A1/es unknown
-
2001
- 2001-10-12 NO NO20014976A patent/NO20014976D0/no not_active Application Discontinuation
- 2001-11-13 ZA ZA200109343A patent/ZA200109343B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002542231A (ja) | 2002-12-10 |
| CN1345312A (zh) | 2002-04-17 |
| WO2000063178A1 (de) | 2000-10-26 |
| ZA200109343B (en) | 2003-04-30 |
| PL350354A1 (en) | 2002-12-02 |
| AU3817400A (en) | 2000-11-02 |
| KR20010102570A (ko) | 2001-11-15 |
| DE19916837A1 (de) | 2000-10-19 |
| HUP0200643A3 (en) | 2003-10-28 |
| HUP0200643A2 (hu) | 2002-07-29 |
| EP1169306A1 (de) | 2002-01-09 |
| BR0009690A (pt) | 2002-01-08 |
| CA2367359A1 (en) | 2000-10-26 |
| NO20014976L (no) | 2001-10-12 |
| SK14342001A3 (sk) | 2002-04-04 |
| NO20014976D0 (no) | 2001-10-12 |
| CZ20013704A3 (cs) | 2002-02-13 |
| MXPA01010294A (es) | 2002-05-06 |
| US6521646B1 (en) | 2003-02-18 |
| AR023496A1 (es) | 2002-09-04 |
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