SK4272000A3 - The use of dolastatin-15 derivative in the treatment and prevention of rheumatoid arthritis - Google Patents

The use of dolastatin-15 derivative in the treatment and prevention of rheumatoid arthritis Download PDF

Info

Publication number: SK4272000A3
Authority: SK; Slovakia
Prior art keywords: prolyl; tert; carbonyl; val; formula
Prior art date: 1997-10-06

Application number

SK427-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Teresa Barlozzari

Subhashis Banerjee

Andreas Haupt

Original Assignee

Basf Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-10-06

Filing date

1998-09-24

Publication date

2001-02-12

1998-09-24 Application filed by Basf Ag filed Critical Basf Ag

2001-02-12 Publication of SK4272000A3 publication Critical patent/SK4272000A3/sk

Links

206010039073 rheumatoid arthritis Diseases 0.000 title claims abstract description 33
238000011282 treatment Methods 0.000 title claims abstract description 33
LQKSHSFQQRCAFW-CCVNJFHASA-N [(2s)-1-[(2s)-2-benzyl-3-methoxy-5-oxo-2h-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl] (2s)-1-[(2s)-1-[(2s)-2-[[(2s)-2-[[(2s)-2-(dimethylamino)-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxyl Chemical class C([C@@H]1N(C(=O)C=C1OC)C(=O)[C@@H](OC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H](C(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C)C(C)C)C(C)C)C1=CC=CC=C1 LQKSHSFQQRCAFW-CCVNJFHASA-N 0.000 title claims description 40
230000002265 prevention Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 77
-1 2,2-dimethylglycyl Chemical group 0.000 claims description 218
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 23
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
229950003188 isovaleryl diethylamide Drugs 0.000 claims description 20
125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 12
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
238000011321 prophylaxis Methods 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001203 alloisoleucine group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000005412 pyrazyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 2
125000002114 valyl group Chemical group 0.000 claims 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
125000001998 leucyl group Chemical group 0.000 claims 2
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
125000000405 phenylalanyl group Chemical group 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000005454 tryptophanyl group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 33
239000000203 mixture Substances 0.000 abstract description 17
229940124347 antiarthritic drug Drugs 0.000 abstract description 15
230000001629 suppression Effects 0.000 abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 92
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000011347 resin Substances 0.000 description 35
229920005989 resin Polymers 0.000 description 35
108090000765 processed proteins & peptides Proteins 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 31
229940024606 amino acid Drugs 0.000 description 24
239000000047 product Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
150000001413 amino acids Chemical class 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
241001465754 Metazoa Species 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
239000012074 organic phase Substances 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
108010077112 prolyl-proline Proteins 0.000 description 16
208000024891 symptom Diseases 0.000 description 16
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
RWCOTTLHDJWHRS-YUMQZZPRSA-N Pro-Pro Chemical compound OC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 RWCOTTLHDJWHRS-YUMQZZPRSA-N 0.000 description 14
230000003053 immunization Effects 0.000 description 13
238000002649 immunization Methods 0.000 description 13
241000699670 Mus sp. Species 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
230000002917 arthritic effect Effects 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
208000009386 Experimental Arthritis Diseases 0.000 description 10
235000015165 citric acid Nutrition 0.000 description 10
125000006239 protecting group Chemical group 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
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UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 9
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FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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UGNIYGNGCNXHTR-SFHVURJKSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](C(C)C)C(O)=O)C3=CC=CC=C3C2=C1 UGNIYGNGCNXHTR-SFHVURJKSA-N 0.000 description 5
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FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 4
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238000007911 parenteral administration Methods 0.000 description 1
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235000011007 phosphoric acid Nutrition 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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150000003953 γ-lactams Chemical group 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Microbiology (AREA)
Mycology (AREA)
Gastroenterology & Hepatology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Chemistry (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

SK427-2000A 1997-10-06 1998-09-24 The use of dolastatin-15 derivative in the treatment and prevention of rheumatoid arthritis SK4272000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/944,479 US6015790A (en)	1997-10-06	1997-10-06	Methods and compositions for treating rheumatoid arthritis
PCT/US1998/019841 WO1999017792A1 (en)	1997-10-06	1998-09-24	Methods and compositions for treating rheumatoid arthritis

Publications (1)

Publication Number	Publication Date
SK4272000A3 true SK4272000A3 (en)	2001-02-12

Family

ID=25481479

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK427-2000A SK4272000A3 (en)	1997-10-06	1998-09-24	The use of dolastatin-15 derivative in the treatment and prevention of rheumatoid arthritis

Country Status (24)

Country	Link
US (1)	US6015790A (de)
EP (1)	EP1021200B1 (de)
JP (1)	JP2001518515A (de)
KR (1)	KR20010081900A (de)
CN (1)	CN1278734A (de)
AR (1)	AR017298A1 (de)
AT (1)	ATE212855T1 (de)
AU (2)	AU748465B2 (de)
BG (1)	BG104292A (de)
BR (1)	BR9812875A (de)
CA (1)	CA2305688A1 (de)
DE (1)	DE69803792D1 (de)
DK (1)	DK1021200T3 (de)
ES (1)	ES2173626T3 (de)
HR (1)	HRP20000265A2 (de)
HU (1)	HUP0101715A3 (de)
IL (1)	IL135167A0 (de)
NO (1)	NO20001758L (de)
PL (1)	PL339731A1 (de)
PT (1)	PT1021200E (de)
SK (1)	SK4272000A3 (de)
TR (1)	TR200000903T2 (de)
WO (2)	WO1999017792A1 (de)
ZA (1)	ZA989036B (de)

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* Cited by examiner, † Cited by third party
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US20010009901A1 (en) *	1996-12-11	2001-07-26	Basf Aktiengesellschaft Germany	Antineoplastic peptides
KR100261114B1 (ko) *	1998-01-24	2000-07-01	박종헌	히스톤을 함유하는 류마티스 관절염 치료제 조성물
CA2383026A1 (en) *	1999-09-14	2001-03-22	Pfizer Products Inc.	Combination treatment with il-1ra and compounds that inhibit il-1 processing and release
WO2001041789A1 (fr) *	1999-12-07	2001-06-14	Santen Pharmaceutical Co., Ltd.	Medicament contre les rhumatismes contenant un derive tetrapeptidique en tant qu'ingredient actif
MXPA02006163A (es) *	1999-12-24	2002-12-05	Hoffmann La Roche	Derivados de nitrilo como inhibidores de la catepsina k.
RU2009130455A (ru) *	2007-01-09	2011-02-20	Байер Шеринг Фарма Акциенгезельшафт (DE)	Введение радиоактивного изотопа путем фторирования азиридинов
WO2010147547A1 (en) *	2009-06-18	2010-12-23	Neobiotics Ab	Novel peptide derivatives for treatment, prevention or alleviation of a condition associated with bone loss or low bone density or to inhibit osteoclast differentiation and stimulation
CN104903320B (zh) *	2013-01-11	2018-11-13	富士胶片株式会社	含氮杂环化合物或其盐
KR102372512B1 (ko) *	2017-11-20	2022-03-10	가톨릭대학교 산학협력단	폴리감마글루탐산 및 메토트렉세이트를 유효성분으로 포함하는 관절염 예방 또는 치료용 조성물
CN115281149A (zh) *	2021-05-12	2022-11-04	四川大学华西医院	一种临床前类风湿关节炎(Pre-RA)小鼠模型

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4816444A (en) *	1987-07-10	1989-03-28	Arizona Board Of Regents, Arizona State University	Cell growth inhibitory substance
US4879278A (en) *	1989-05-16	1989-11-07	Arizona Board Of Regents	Isolation and structural elucidation of the cytostatic linear depsipeptide dolastatin 15
AU662551B2 (en) *	1991-08-09	1995-09-07	Teikoku Hormone Mfg. Co., Ltd.	Novel tetrapeptide derivative
US5831002A (en) *	1992-05-20	1998-11-03	Basf Aktiengesellschaft	Antitumor peptides
PL178766B1 (pl) *	1992-12-16	2000-06-30	Basf Ag	Nowe peptydy
US5504191A (en) *	1994-08-01	1996-04-02	Arizona Board Of Regents Acting On Behalf Of Arizona State University	Human cancer inhibitory pentapeptide methyl esters
US5530097A (en) *	1994-08-01	1996-06-25	Arizona Board Of Regents Acting On Behalf Of Arizona State University	Human cancer inhibitory peptide amides
US5583153A (en) *	1994-10-06	1996-12-10	Regents Of The University Of California	Use of taxol in the treatment of rheumatoid arthritis

1997
- 1997-10-06 US US08/944,479 patent/US6015790A/en not_active Expired - Fee Related
1998
- 1998-09-24 PL PL98339731A patent/PL339731A1/xx not_active Application Discontinuation
- 1998-09-24 BR BR9812875-2A patent/BR9812875A/pt not_active IP Right Cessation
- 1998-09-24 AU AU95024/98A patent/AU748465B2/en not_active Ceased
- 1998-09-24 DE DE69803792T patent/DE69803792D1/de not_active Expired - Fee Related
- 1998-09-24 ES ES98948455T patent/ES2173626T3/es not_active Expired - Lifetime
- 1998-09-24 WO PCT/US1998/019841 patent/WO1999017792A1/en not_active Ceased
- 1998-09-24 CN CN98811034A patent/CN1278734A/zh active Pending
- 1998-09-24 JP JP2000514663A patent/JP2001518515A/ja not_active Withdrawn
- 1998-09-24 CA CA002305688A patent/CA2305688A1/en not_active Abandoned
- 1998-09-24 DK DK98948455T patent/DK1021200T3/da active
- 1998-09-24 HR HR20000265A patent/HRP20000265A2/hr not_active Application Discontinuation
- 1998-09-24 TR TR2000/00903T patent/TR200000903T2/xx unknown
- 1998-09-24 EP EP98948455A patent/EP1021200B1/de not_active Expired - Lifetime
- 1998-09-24 AT AT98948455T patent/ATE212855T1/de not_active IP Right Cessation
- 1998-09-24 SK SK427-2000A patent/SK4272000A3/sk unknown
- 1998-09-24 HU HU0101715A patent/HUP0101715A3/hu unknown
- 1998-09-24 KR KR1020007003706A patent/KR20010081900A/ko not_active Withdrawn
- 1998-09-24 IL IL13516798A patent/IL135167A0/xx unknown
- 1998-09-24 PT PT98948455T patent/PT1021200E/pt unknown
- 1998-09-30 AU AU95926/98A patent/AU9592698A/en not_active Withdrawn
- 1998-09-30 WO PCT/US1998/020465 patent/WO1999017709A2/en not_active Ceased
- 1998-10-05 ZA ZA9809036A patent/ZA989036B/xx unknown
- 1998-10-06 AR ARP980104972A patent/AR017298A1/es not_active Application Discontinuation
2000
- 2000-04-03 BG BG104292A patent/BG104292A/xx unknown
- 2000-04-05 NO NO20001758A patent/NO20001758L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP0101715A2 (hu)	2001-11-28
ATE212855T1 (de)	2002-02-15
DK1021200T3 (da)	2002-05-27
BG104292A (en)	2000-12-29
NO20001758D0 (no)	2000-04-05
CN1278734A (zh)	2001-01-03
BR9812875A (pt)	2000-08-08
HUP0101715A3 (en)	2001-12-28
AU9502498A (en)	1999-04-27
CA2305688A1 (en)	1999-04-15
WO1999017792A1 (en)	1999-04-15
KR20010081900A (ko)	2001-08-29
EP1021200A1 (de)	2000-07-26
NO20001758L (no)	2000-06-05
AU9592698A (en)	1999-04-27
ES2173626T3 (es)	2002-10-16
EP1021200B1 (de)	2002-02-06
WO1999017709A2 (en)	1999-04-15
JP2001518515A (ja)	2001-10-16
TR200000903T2 (tr)	2001-07-23
PL339731A1 (en)	2001-01-02
IL135167A0 (en)	2001-05-20
ZA989036B (en)	2000-04-05
US6015790A (en)	2000-01-18
DE69803792D1 (de)	2002-03-21
HRP20000265A2 (en)	2000-12-31
PT1021200E (pt)	2002-07-31
AR017298A1 (es)	2001-09-05
AU748465B2 (en)	2002-06-06

Publication	Publication Date	Title
AU679479B2 (en)	1997-07-03	Dolostatin analog
RU2195462C2 (ru)	2002-12-27	Производные доластатина 15
AU669710B2 (en)	1996-06-20	Derivatives of dolastatin
EP0832104A1 (de)	1998-04-01	Neue derivate von dolastatin, dreen herstellung un verwendung
SK4272000A3 (en)	2001-02-12	The use of dolastatin-15 derivative in the treatment and prevention of rheumatoid arthritis
EP0981358B1 (de)	2003-05-28	Zusammensetzungen, die dolastatin-15-analoge in kombination mit taxane und dessen derivaten enthalten
SK76798A3 (en)	1999-02-11	Antineoplastic peptides
CZ20001211A3 (cs)	2001-06-13	Prostředky pro léčení revmatoidní artritidy
US20010009901A1 (en)	2001-07-26	Antineoplastic peptides
MXPA00003289A (en)	2001-06-26	Methods and compositions for treating rheumatoid arthritis