SK12498A3 - Thalidomide analogues from the piperidine-2,6-dione class - Google Patents

Thalidomide analogues from the piperidine-2,6-dione class Download PDF

Info

Publication number: SK12498A3
Authority: SK; Slovakia
Prior art keywords: substituted; piperidine; dione; hydrogen; formula
Prior art date: 1997-02-01

Application number

SK124-98A

Other languages

English (en)

Slovak (sk)

Inventor

Oswald Zimmer

Werner Winter

Stephan Wnendt

Kai Zwingenberger

Kurt Eger

Uwe Teubert

Original Assignee

Gruenenthal Gmbh

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.)

1997-02-01

Filing date

1998-01-29

Publication date

1998-08-05

1998-01-29 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

1998-08-05 Publication of SK12498A3 publication Critical patent/SK12498A3/sk

Links

150000005459 piperidine-2,6-diones Chemical class 0.000 title claims description 12
UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 title description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000005543 phthalimide group Chemical group 0.000 claims abstract description 5
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 8
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
-1 hydroxy, methoxy Chemical group 0.000 claims description 3
150000003949 imides Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
235000013922 glutamic acid Nutrition 0.000 claims description 2
239000004220 glutamic acid Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
NPWMTBZSRRLQNJ-UHFFFAOYSA-N pyroglutamine Chemical group NC1CCC(=O)NC1=O NPWMTBZSRRLQNJ-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
YZJUCSJIJAZADS-UHFFFAOYSA-N 4-amino-3h-pyridine-2,6-dione Chemical group NC1=CC(=O)NC(=O)C1 YZJUCSJIJAZADS-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000002955 immunomodulating agent Substances 0.000 claims 1
229940121354 immunomodulator Drugs 0.000 claims 1
230000002584 immunomodulator Effects 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 abstract description 2
125000001072 heteroaryl group Chemical group 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
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102000000588 Interleukin-2 Human genes 0.000 description 9
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210000001744 T-lymphocyte Anatomy 0.000 description 7
230000000638 stimulation Effects 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
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CNLJMMLBJYVTPG-UHFFFAOYSA-N 2-(2,6-dioxo-5-phenylpiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C(NC1=O)=O)CC1C1=CC=CC=C1 CNLJMMLBJYVTPG-UHFFFAOYSA-N 0.000 description 5
PXEMWOBLTOCKAW-UHFFFAOYSA-N 2-(5-ethyl-2,6-dioxo-5-phenylpiperidin-3-yl)isoindole-1,3-dione Chemical compound C1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)NC(=O)C1(CC)C1=CC=CC=C1 PXEMWOBLTOCKAW-UHFFFAOYSA-N 0.000 description 5
239000000427 antigen Substances 0.000 description 5
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239000002904 solvent Substances 0.000 description 5
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238000003786 synthesis reaction Methods 0.000 description 5
BGXFWODZPIPOKE-UHFFFAOYSA-N 2-(5-methyl-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1NC(=O)C(C)CC1N1C(=O)C2=CC=CC=C2C1=O BGXFWODZPIPOKE-UHFFFAOYSA-N 0.000 description 4
KRKRAOXTGDJWNI-UHFFFAOYSA-N 4-Methylglutamic acid Chemical compound OC(=O)C(C)CC(N)C(O)=O KRKRAOXTGDJWNI-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
238000005516 engineering process Methods 0.000 description 4
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210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 4
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UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
YFUKGSPPGJKWNX-UHFFFAOYSA-N 2-(5-ethyl-2,6-dioxo-5-phenylpyridin-3-yl)-4,5-dimethoxyisoindole-1,3-dione Chemical compound C1=C(N2C(C3=C(OC)C(OC)=CC=C3C2=O)=O)C(=O)NC(=O)C1(CC)C1=CC=CC=C1 YFUKGSPPGJKWNX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
210000003719 b-lymphocyte Anatomy 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000008629 immune suppression Effects 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KPYSVDPUAXYRHZ-GKAPJAKFSA-N (2s)-2-amino-4-phenylpentanedioic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)C1=CC=CC=C1 KPYSVDPUAXYRHZ-GKAPJAKFSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
101000914514 Homo sapiens T-cell-specific surface glycoprotein CD28 Proteins 0.000 description 2
101000686985 Mouse mammary tumor virus (strain C3H) Protein PR73 Proteins 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
101000794214 Staphylococcus aureus Toxic shock syndrome toxin-1 Proteins 0.000 description 2
102100027213 T-cell-specific surface glycoprotein CD28 Human genes 0.000 description 2
208000002399 aphthous stomatitis Diseases 0.000 description 2
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210000004027 cell Anatomy 0.000 description 2
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210000003038 endothelium Anatomy 0.000 description 2
239000012894 fetal calf serum Substances 0.000 description 2
239000012997 ficoll-paque Substances 0.000 description 2
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
230000001506 immunosuppresive effect Effects 0.000 description 2
239000003018 immunosuppressive agent Substances 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
210000004400 mucous membrane Anatomy 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
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231100000617 superantigen Toxicity 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
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DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
FPYMWUSMIRXSEA-UHFFFAOYSA-N 4,5-dimethoxy-2-benzofuran-1,3-dione Chemical compound COC1=CC=C2C(=O)OC(=O)C2=C1OC FPYMWUSMIRXSEA-UHFFFAOYSA-N 0.000 description 1
IMSDRBDUANUSRL-UHFFFAOYSA-N 5,6-dimethoxy-2-benzofuran-1,3-dione Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2=O IMSDRBDUANUSRL-UHFFFAOYSA-N 0.000 description 1
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101000685085 Centruroides noxius Toxin Cn1 Proteins 0.000 description 1
101001028688 Chironex fleckeri Toxin CfTX-1 Proteins 0.000 description 1
101000644407 Cyriopagopus schmidti U6-theraphotoxin-Hs1a Proteins 0.000 description 1
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BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
101000679608 Phaeosphaeria nodorum (strain SN15 / ATCC MYA-4574 / FGSC 10173) Cysteine rich necrotrophic effector Tox1 Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000024932 T cell mediated immunity Effects 0.000 description 1
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102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
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239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
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239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
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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 1
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239000003623 enhancer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
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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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Immunology (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Indole Compounds (AREA)

SK124-98A 1997-02-01 1998-01-29 Thalidomide analogues from the piperidine-2,6-dione class SK12498A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19703763A DE19703763C1 (de)	1997-02-01	1997-02-01	Thalidomidanaloge Verbindungen aus der Klasse der Piperidin-2,6-Dione

Publications (1)

Publication Number	Publication Date
SK12498A3 true SK12498A3 (en)	1998-08-05

Family

ID=7819009

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK124-98A SK12498A3 (en)	1997-02-01	1998-01-29	Thalidomide analogues from the piperidine-2,6-dione class

Country Status (27)

Country	Link
US (1)	US6110941A (no)
EP (1)	EP0856513B1 (no)
JP (1)	JPH10316675A (no)
KR (1)	KR19980070959A (no)
CN (1)	CN1109032C (no)
AR (1)	AR010107A1 (no)
AT (1)	ATE311381T1 (no)
AU (1)	AU729733B2 (no)
BR (1)	BR9800253A (no)
CA (1)	CA2228385A1 (no)
CO (1)	CO4940441A1 (no)
CZ (1)	CZ27598A3 (no)
DE (2)	DE19703763C1 (no)
DK (1)	DK0856513T3 (no)
ES (1)	ES2253790T3 (no)
HU (1)	HUP9800146A3 (no)
IL (1)	IL122372A (no)
NO (1)	NO313007B1 (no)
NZ (1)	NZ329325A (no)
PE (1)	PE57499A1 (no)
PL (1)	PL188700B1 (no)
RU (1)	RU2184733C2 (no)
SI (1)	SI0856513T1 (no)
SK (1)	SK12498A3 (no)
UA (1)	UA45408C2 (no)
UY (1)	UY24870A1 (no)
ZA (1)	ZA98749B (no)

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DE10002509A1 (de)	2000-01-21	2001-07-26	Gruenenthal Gmbh	Substituierte Glutarimide
US7320991B2 (en)	2001-02-27	2008-01-22	The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health	Analogs of thalidomide as potential angiogenesis inhibitors
CN100398534C (zh) *	2003-09-15	2008-07-02	天津和美生物技术有限公司	合成酞胺哌啶酮及其衍生物的方法
US7973057B2 (en) *	2003-09-17	2011-07-05	The United States Of America As Represented By The Department Of Health And Human Services	Thalidomide analogs
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WO2007120669A1 (en) *	2006-04-13	2007-10-25	The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services	Tetrahalogenated compounds useful as inhibitors of angiogenesis
JP2013537172A (ja)	2010-09-09	2013-09-30	トリフォイリウムエーピーエス	血管新生阻害剤の気道投与
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1997
- 1997-02-01 DE DE19703763A patent/DE19703763C1/de not_active Expired - Fee Related
- 1997-12-01 IL IL12237297A patent/IL122372A/en not_active IP Right Cessation
- 1997-12-04 NZ NZ329325A patent/NZ329325A/en unknown
1998
- 1998-01-09 AT AT98100259T patent/ATE311381T1/de not_active IP Right Cessation
- 1998-01-09 EP EP98100259A patent/EP0856513B1/de not_active Expired - Lifetime
- 1998-01-09 ES ES98100259T patent/ES2253790T3/es not_active Expired - Lifetime
- 1998-01-09 SI SI9830810T patent/SI0856513T1/sl unknown
- 1998-01-09 DK DK98100259T patent/DK0856513T3/da active
- 1998-01-09 DE DE59813233T patent/DE59813233D1/de not_active Expired - Lifetime
- 1998-01-16 BR BR9800253A patent/BR9800253A/pt not_active IP Right Cessation
- 1998-01-19 PE PE1998000038A patent/PE57499A1/es not_active Application Discontinuation
- 1998-01-23 AR ARP980100306A patent/AR010107A1/es unknown
- 1998-01-28 HU HU9800146A patent/HUP9800146A3/hu unknown
- 1998-01-29 SK SK124-98A patent/SK12498A3/sk unknown
- 1998-01-29 ZA ZA98749A patent/ZA98749B/xx unknown
- 1998-01-29 CO CO98004231A patent/CO4940441A1/es unknown
- 1998-01-29 US US09/015,624 patent/US6110941A/en not_active Expired - Fee Related
- 1998-01-29 CZ CZ98275A patent/CZ27598A3/cs unknown
- 1998-01-29 UA UA98010495A patent/UA45408C2/uk unknown
- 1998-01-30 AU AU52840/98A patent/AU729733B2/en not_active Ceased
- 1998-01-30 UY UY24870A patent/UY24870A1/es unknown
- 1998-01-30 RU RU98103164/04A patent/RU2184733C2/ru not_active IP Right Cessation
- 1998-01-30 JP JP10019744A patent/JPH10316675A/ja not_active Withdrawn
- 1998-01-30 PL PL98324588A patent/PL188700B1/pl not_active IP Right Cessation
- 1998-01-30 NO NO19980416A patent/NO313007B1/no unknown
- 1998-01-30 CA CA002228385A patent/CA2228385A1/en not_active Abandoned
- 1998-01-31 KR KR1019980002615A patent/KR19980070959A/ko not_active Ceased
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Also Published As

Publication number	Publication date
CZ27598A3 (cs)	1998-08-12
UY24870A1 (es)	2001-05-31
CN1190096A (zh)	1998-08-12
HK1015363A1 (en)	1999-10-15
IL122372A0 (en)	1998-06-15
PL188700B1 (pl)	2005-03-31
CN1109032C (zh)	2003-05-21
ATE311381T1 (de)	2005-12-15
AR010107A1 (es)	2000-05-17
HU9800146D0 (en)	1998-03-30
ZA98749B (en)	1998-08-03
NO980416L (no)	1998-08-03
NZ329325A (en)	1998-07-28
KR19980070959A (ko)	1998-10-26
JPH10316675A (ja)	1998-12-02
EP0856513A3 (de)	1998-09-23
UA45408C2 (uk)	2002-04-15
DE19703763C1 (de)	1998-10-01
DK0856513T3 (da)	2005-12-27
DE59813233D1 (de)	2006-01-05
HUP9800146A2 (hu)	1998-12-28
US6110941A (en)	2000-08-29
BR9800253A (pt)	1999-08-24
PL324588A1 (en)	1998-08-03
PE57499A1 (es)	1999-07-10
SI0856513T1 (sl)	2006-02-28
IL122372A (en)	2002-12-01
HUP9800146A3 (en)	2000-06-28
AU729733B2 (en)	2001-02-08
RU2184733C2 (ru)	2002-07-10
EP0856513B1 (de)	2005-11-30
EP0856513A2 (de)	1998-08-05
CA2228385A1 (en)	1998-08-01
NO980416D0 (no)	1998-01-30
AU5284098A (en)	1998-08-06
NO313007B1 (no)	2002-07-29
CO4940441A1 (es)	2000-07-24
ES2253790T3 (es)	2006-06-01

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RU2163603C2 (ru)	2001-02-27	Замещенные имидазолидин-2,4-дионовые соединения в качестве фармацевтических действующих веществ
KR880000968B1 (ko)	1988-06-07	1, 2-디아미노 시클로부텐-3, 4-디온 및 그의 제조방법
KR960009570B1 (ko)	1996-07-20	이미다졸린 유도체 및 그의 제조방법
US6500845B1 (en)	2002-12-31	Lactam derivatives as immunomodulating agents
HUP9902181A2 (hu)	2000-04-28	Immunomoduláló hatással rendelkező acilezett N-(hidroxi-metil)-thalidomid prodrugok
IE49496B1 (en)	1985-10-16	A 1,4-dihydropyridine derivative,its preparation and pharmaceutical compositions containing it
SK12498A3 (en)	1998-08-05	Thalidomide analogues from the piperidine-2,6-dione class
JPH055829B2 (no)	1993-01-25
PT90475B (pt)	1994-08-31	Processo para a preparacao de pro-farmacos de 2',3'-didehidro-2',3'-didesoxinucleosidos com accao anti-viral
MXPA98000014A (en)	1999-02-24	Analogue compounds of thalidomide from the class of piperidin-2,6-dio
HK1015363B (en)	2004-02-06	Compounds analogous to thalidomide from the class comprising piperidine-2, 6-diones
US6303608B1 (en)	2001-10-16	2-{4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-fluoropyrimidine, its preparation and its therapeutic use
RU2814498C2 (ru)	2024-02-29	Кристаллическая форма ингибитора фосфодиэстеразы, способ ее получения и ее применение
SK122996A3 (en)	1997-05-07	Novel crystal forms of 1-£5-methanesulfonamidoindolyl-2- -carbonyl\|-4-£3-(1-methylethylamino)-2-pyridinyl\|piperazine
HK1011541A (en)	1999-07-16	Compound analogous to thalidomide from the class comprising piperidine-2, 6-diones
JPH01135785A (ja)	1989-05-29	４ｈ―キノリジン―４―オン誘導体
JPH0453870B2 (no)	1992-08-27
JPH01149784A (ja)	1989-06-12	４ｈ−キノリジン−４−オン誘導体
JP2000256327A (ja)	2000-09-19	新規イソキノリン誘導体
CA2168231A1 (en)	1995-02-09	(thio)carbimidinic acid derivatives and pharmaceutical agents containing them
MXPA98007998A (en)	1999-04-06	Acrylic prodrogas of n-hydroxymethyl talidomide with immunomodula activity
JPH085884B2 (ja)	1996-01-24	５Ｈ−ピラゾロ〔４，３−ａ〕キノリジン−５−オン誘導体