BG106562A - Трициклени инхибитори на поли (adp-рибоза) полимерази - Google Patents

Трициклени инхибитори на поли (adp-рибоза) полимерази Download PDF

Info

Publication number: BG106562A
Authority: BG; Bulgaria
Prior art keywords: aryl; cycloalkyl; alkynyl; alkenyl; heterocycloalkyl
Prior art date: 1999-08-31

Application number

BG106562A

Other languages

Bulgarian (bg)

English (en)

Inventor

Stephen Webber

Donald SKALITZKY

Jayashree Tikhe

Arnold KUMPF

Joseph MARAKOVITS

Walter EASTMAN

Original Assignee

Agouron Pharmaceuticals, Inc.

Cancer Research Campaign Technology Limited

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.)

1999-08-31

Filing date

2002-03-29

Publication date

2003-03-31

2002-03-29 Application filed by Agouron Pharmaceuticals, Inc., Cancer Research Campaign Technology Limited filed Critical Agouron Pharmaceuticals, Inc.

2003-03-31 Publication of BG106562A publication Critical patent/BG106562A/bg

Links

229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims description 18
239000003112 inhibitor Substances 0.000 title description 12
102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 7
108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 316
230000000694 effects Effects 0.000 claims abstract description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 229
-1 hydroxy, nitro, amino Chemical group 0.000 claims description 205
238000000034 method Methods 0.000 claims description 202
125000003118 aryl group Chemical group 0.000 claims description 187
125000001072 heteroaryl group Chemical group 0.000 claims description 156
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 147
125000000753 cycloalkyl group Chemical group 0.000 claims description 144
125000000304 alkynyl group Chemical group 0.000 claims description 142
125000003342 alkenyl group Chemical group 0.000 claims description 138
125000000547 substituted alkyl group Chemical group 0.000 claims description 125
125000000217 alkyl group Chemical group 0.000 claims description 98
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 58
150000003839 salts Chemical class 0.000 claims description 50
230000005764 inhibitory process Effects 0.000 claims description 43
102000004190 Enzymes Human genes 0.000 claims description 40
108090000790 Enzymes Proteins 0.000 claims description 40
239000012453 solvate Substances 0.000 claims description 37
125000004093 cyano group Chemical group *C#N 0.000 claims description 36
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
239000000651 prodrug Substances 0.000 claims description 36
229940002612 prodrug Drugs 0.000 claims description 36
239000002207 metabolite Substances 0.000 claims description 35
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
239000003795 chemical substances by application Substances 0.000 claims description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 30
230000002401 inhibitory effect Effects 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 25
241000124008 Mammalia Species 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 12
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
238000003556 assay Methods 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
238000004458 analytical method Methods 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
230000003389 potentiating effect Effects 0.000 claims description 6
231100000433 cytotoxic Toxicity 0.000 claims description 5
230000001472 cytotoxic effect Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 3
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102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 11
125000005017 substituted alkenyl group Chemical group 0.000 claims 4
SRNWOUGRCWSEMX-TYASJMOZSA-N ADP-D-ribose Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=2N=CN=C(C=2N=C1)N)OP(O)(=O)OP(O)(=O)OC[C@H]1OC(O)[C@H](O)[C@@H]1O SRNWOUGRCWSEMX-TYASJMOZSA-N 0.000 claims 2
125000005248 alkyl aryloxy group Chemical group 0.000 claims 1
230000002255 enzymatic effect Effects 0.000 claims 1
208000006011 Stroke Diseases 0.000 abstract description 9
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238000005481 NMR spectroscopy Methods 0.000 description 310
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 294
239000007787 solid Substances 0.000 description 248
229910052739 hydrogen Inorganic materials 0.000 description 237
229910052799 carbon Inorganic materials 0.000 description 219
235000019439 ethyl acetate Nutrition 0.000 description 146
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 116
239000011541 reaction mixture Substances 0.000 description 106
238000004128 high performance liquid chromatography Methods 0.000 description 96
239000000047 product Substances 0.000 description 92
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239000000243 solution Substances 0.000 description 85
150000001412 amines Chemical class 0.000 description 65
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238000000354 decomposition reaction Methods 0.000 description 56
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238000006243 chemical reaction Methods 0.000 description 48
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150000004985 diamines Chemical class 0.000 description 31
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WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 29
231100000135 cytotoxicity Toxicity 0.000 description 29
230000003013 cytotoxicity Effects 0.000 description 29
239000000203 mixture Substances 0.000 description 29
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 27
239000012044 organic layer Substances 0.000 description 27
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238000011282 treatment Methods 0.000 description 22
150000001299 aldehydes Chemical class 0.000 description 21
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RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
230000035484 reaction time Effects 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
239000012267 brine Substances 0.000 description 17
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
239000012661 PARP inhibitor Substances 0.000 description 14
229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 14
229910052763 palladium Inorganic materials 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
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239000000725 suspension Substances 0.000 description 13
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150000002576 ketones Chemical class 0.000 description 11
238000010992 reflux Methods 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000011734 sodium Substances 0.000 description 11
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
XQVZDADGTFJAFM-UHFFFAOYSA-N Indole-7-carboxaldehyde Chemical compound O=CC1=CC=CC2=C1NC=C2 XQVZDADGTFJAFM-UHFFFAOYSA-N 0.000 description 10
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229960000583 acetic acid Drugs 0.000 description 10
239000002253 acid Substances 0.000 description 10
125000001588 azulen-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C([H])C2=C1* 0.000 description 10
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
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TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
PZDPUQUIZKCNOF-UHFFFAOYSA-N tert-butyl 2-(4-bromophenyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C1=CC=C(Br)C=C1 PZDPUQUIZKCNOF-UHFFFAOYSA-N 0.000 description 1
XUZPXVRIGTVCLR-UHFFFAOYSA-N tert-butyl 2-(4-bromophenyl)pyrrolidine-1-carboxylate;tert-butyl 2-(4-formylphenyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C1=CC=C(Br)C=C1.CC(C)(C)OC(=O)N1CCCC1C1=CC=C(C=O)C=C1 XUZPXVRIGTVCLR-UHFFFAOYSA-N 0.000 description 1
IWFWSTSIZXLBFI-UHFFFAOYSA-N tert-butyl 2-(4-formylphenyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C1=CC=C(C=O)C=C1 IWFWSTSIZXLBFI-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
WARKYKQCOXTIAO-UHFFFAOYSA-N tributyl(2-ethoxyethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C/OCC WARKYKQCOXTIAO-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011534 wash buffer Substances 0.000 description 1
GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG106562A 1999-08-31 2002-03-29 Трициклени инхибитори на поли (adp-рибоза) полимерази BG106562A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15214299P	1999-08-31	1999-08-31
PCT/US2000/023882 WO2001016136A2 (en)	1999-08-31	2000-08-31	Tricyclic inhibitors of poly(adp-ribose) polymerases

Publications (1)

Publication Number	Publication Date
BG106562A true BG106562A (bg)	2003-03-31

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Application Number	Title	Priority Date	Filing Date
BG106562A BG106562A (bg)	1999-08-31	2002-03-29	Трициклени инхибитори на поли (adp-рибоза) полимерази

Country Status (48)

Country	Link
US (1)	US6548494B1 (ja)
EP (1)	EP1208104B1 (ja)
JP (1)	JP4272375B2 (ja)
KR (1)	KR20020038742A (ja)
CN (1)	CN1384835A (ja)
AP (1)	AP1553A (ja)
AR (1)	AR035162A1 (ja)
AT (1)	ATE287406T1 (ja)
AU (1)	AU781826B2 (ja)
BG (1)	BG106562A (ja)
BR (1)	BR0015051A (ja)
CA (1)	CA2382404C (ja)
CO (1)	CO5200769A1 (ja)
CR (1)	CR6577A (ja)
CZ (1)	CZ2002613A3 (ja)
DE (1)	DE60017575T2 (ja)
DK (1)	DK1208104T3 (ja)
DO (1)	DOP2000000069A (ja)
DZ (1)	DZ3216A1 (ja)
EA (1)	EA200200306A1 (ja)
EC (1)	ECSP003637A (ja)
EE (1)	EE200200100A (ja)
ES (1)	ES2234657T3 (ja)
GE (1)	GEP20043268B (ja)
GT (1)	GT200000145A (ja)
HK (1)	HK1045509B (ja)
HR (1)	HRP20020271A2 (ja)
HU (1)	HUP0202703A3 (ja)
IL (1)	IL147863A0 (ja)
IS (1)	IS6289A (ja)
MA (1)	MA25876A1 (ja)
MX (1)	MXPA02002138A (ja)
MY (1)	MY135910A (ja)
NO (1)	NO322475B1 (ja)
NZ (1)	NZ516793A (ja)
OA (1)	OA12016A (ja)
PA (1)	PA8501801A1 (ja)
PE (1)	PE20010538A1 (ja)
PL (1)	PL354242A1 (ja)
PT (1)	PT1208104E (ja)
SI (1)	SI1208104T1 (ja)
SK (1)	SK2592002A3 (ja)
SV (1)	SV2003000162A (ja)
UA (1)	UA73144C2 (ja)
UY (1)	UY26323A1 (ja)
WO (1)	WO2001016136A2 (ja)
YU (1)	YU15102A (ja)
ZA (1)	ZA200200830B (ja)

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2000
- 2000-08-29 EC EC2000003637A patent/ECSP003637A/es unknown
- 2000-08-30 MY MYPI20004039A patent/MY135910A/en unknown
- 2000-08-30 GT GT200000145A patent/GT200000145A/es unknown
- 2000-08-30 CO CO00065062A patent/CO5200769A1/es not_active Application Discontinuation
- 2000-08-31 AT AT00961437T patent/ATE287406T1/de not_active IP Right Cessation
- 2000-08-31 AR ARP000104549A patent/AR035162A1/es unknown
- 2000-08-31 GE GEAP20006389A patent/GEP20043268B/en unknown
- 2000-08-31 AU AU73389/00A patent/AU781826B2/en not_active Ceased
- 2000-08-31 SK SK259-2002A patent/SK2592002A3/sk unknown
- 2000-08-31 UY UY26323A patent/UY26323A1/es not_active Application Discontinuation
- 2000-08-31 BR BR0015051-7A patent/BR0015051A/pt not_active Application Discontinuation
- 2000-08-31 MX MXPA02002138A patent/MXPA02002138A/es active IP Right Grant
- 2000-08-31 DZ DZ003216A patent/DZ3216A1/fr active
- 2000-08-31 SV SV2000000162A patent/SV2003000162A/es unknown
- 2000-08-31 NZ NZ516793A patent/NZ516793A/en unknown
- 2000-08-31 DE DE60017575T patent/DE60017575T2/de not_active Expired - Lifetime
- 2000-08-31 HR HR20020271A patent/HRP20020271A2/hr not_active Application Discontinuation
- 2000-08-31 KR KR1020027002629A patent/KR20020038742A/ko not_active Abandoned
- 2000-08-31 PL PL00354242A patent/PL354242A1/xx not_active Application Discontinuation
- 2000-08-31 JP JP2001519702A patent/JP4272375B2/ja not_active Expired - Lifetime
- 2000-08-31 DK DK00961437T patent/DK1208104T3/da active
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- 2000-08-31 WO PCT/US2000/023882 patent/WO2001016136A2/en not_active Ceased
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- 2000-08-31 PE PE2000000896A patent/PE20010538A1/es not_active Application Discontinuation
- 2000-08-31 US US09/653,184 patent/US6548494B1/en not_active Expired - Lifetime
- 2000-08-31 CA CA002382404A patent/CA2382404C/en not_active Expired - Fee Related
- 2000-08-31 CZ CZ2002613A patent/CZ2002613A3/cs unknown
- 2000-08-31 HK HK02106977.2A patent/HK1045509B/en not_active IP Right Cessation
- 2000-08-31 CN CN00815066A patent/CN1384835A/zh active Pending
- 2000-08-31 EA EA200200306A patent/EA200200306A1/ru unknown
- 2000-08-31 UA UA2002042574A patent/UA73144C2/uk unknown
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- 2000-08-31 AP APAP/P/2002/002449A patent/AP1553A/en active
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- 2000-08-31 PT PT00961437T patent/PT1208104E/pt unknown
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2002
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- 2002-01-30 ZA ZA200200830A patent/ZA200200830B/en unknown
- 2002-02-01 CR CR6577A patent/CR6577A/es not_active Application Discontinuation
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Also Published As

Publication number	Publication date
AR035162A1 (es)	2004-05-05
AU7338900A (en)	2001-03-26
EP1208104A2 (en)	2002-05-29
IL147863A0 (en)	2002-08-14
UA73144C2 (en)	2005-06-15
AP1553A (en)	2006-01-18
SI1208104T1 (en)	2005-06-30
PA8501801A1 (es)	2002-08-26
GT200000145A (es)	2002-02-21
PE20010538A1 (es)	2001-05-22
AU781826B2 (en)	2005-06-16
NZ516793A (en)	2004-03-26
SK2592002A3 (en)	2002-10-08
CR6577A (es)	2003-12-05
UY26323A1 (es)	2001-04-30
DZ3216A1 (fr)	2001-03-08
WO2001016136A3 (en)	2001-06-21
CZ2002613A3 (cs)	2002-08-14
BR0015051A (pt)	2002-06-25
HRP20020271A2 (en)	2005-12-31
YU15102A (sh)	2004-12-31
NO20020421L (no)	2002-04-25
MXPA02002138A (es)	2003-08-20
CO5200769A1 (es)	2002-09-27
GEP20043268B (en)	2004-06-25
US6548494B1 (en)	2003-04-15
WO2001016136A2 (en)	2001-03-08
NO20020421D0 (no)	2002-01-28
PL354242A1 (en)	2003-12-29
DK1208104T3 (da)	2005-05-02
EE200200100A (et)	2003-06-16
DOP2000000069A (es)	2002-08-30
IS6289A (is)	2002-02-27
ZA200200830B (en)	2003-03-26
WO2001016136B1 (en)	2001-11-15
EP1208104B1 (en)	2005-01-19
NO322475B1 (no)	2006-10-09
JP4272375B2 (ja)	2009-06-03
JP2003513015A (ja)	2003-04-08
MY135910A (en)	2008-07-31
HK1045509A1 (en)	2002-11-29
HUP0202703A2 (hu)	2002-12-28
MA25876A1 (fr)	2003-10-01
OA12016A (en)	2006-04-19
SV2003000162A (es)	2003-07-29
CA2382404C (en)	2009-03-24
KR20020038742A (ko)	2002-05-23
PT1208104E (pt)	2005-04-29
HK1045509B (en)	2005-04-29
ECSP003637A (es)	2002-03-25
HUP0202703A3 (en)	2004-12-28
EA200200306A1 (ru)	2002-08-29
CA2382404A1 (en)	2001-03-08
DE60017575T2 (de)	2005-06-09
DE60017575D1 (de)	2005-02-24
ES2234657T3 (es)	2005-07-01
ATE287406T1 (de)	2005-02-15
CN1384835A (zh)	2002-12-11

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