DD289529A5 - Verfahren zur herstellung heterozyklischer verbindungen - Google Patents

Verfahren zur herstellung heterozyklischer verbindungen Download PDF

Info

Publication number: DD289529A5
Authority: DD; German Democratic Republic
Prior art keywords: carbamate; group; formula; imidazo; methyl
Prior art date: 1987-08-15

Application number

DD88318868A

Other languages

German (de)

English (en)

Inventor

Simon T Hodgson

Original Assignee

��@��@��@��k��

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.)

1987-08-15

Filing date

1988-08-12

Publication date

1991-05-02

1988-08-12 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1991-05-02 Publication of DD289529A5 publication Critical patent/DD289529A5/de

Links

150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 3
238000004519 manufacturing process Methods 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 154
238000000034 method Methods 0.000 claims abstract description 44
206010028980 Neoplasm Diseases 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 16
229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 10
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
-1 3,5-dimethoxybenzyloxy Chemical group 0.000 claims description 98
229910052739 hydrogen Inorganic materials 0.000 claims description 83
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 25
239000003814 drug Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
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125000005842 heteroatom Chemical group 0.000 claims description 4
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125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
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239000005457 ice water Substances 0.000 description 1
239000007943 implant Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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238000001802 infusion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
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150000002513 isocyanates Chemical class 0.000 description 1
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229940099563 lactobionic acid Drugs 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
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CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
231100000782 microtubule inhibitor Toxicity 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
CXGFWBPQQXZELI-UHFFFAOYSA-N n-ethylpyridin-2-amine Chemical compound CCNC1=CC=CC=N1 CXGFWBPQQXZELI-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
ZFACJPAPCXRZMQ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O ZFACJPAPCXRZMQ-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000013074 reference sample Substances 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008137 solubility enhancer Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 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
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

DD88318868A 1987-08-15 1988-08-12 Verfahren zur herstellung heterozyklischer verbindungen DD289529A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878719368A GB8719368D0 (en)	1987-08-15	1987-08-15	Heterocyclic compounds

Publications (1)

Publication Number	Publication Date
DD289529A5 true DD289529A5 (de)	1991-05-02

Family

ID=10622364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318868A DD289529A5 (de)	1987-08-15	1988-08-12	Verfahren zur herstellung heterozyklischer verbindungen

Country Status (28)

Country	Link
US (5)	US5091531A (fr)
EP (1)	EP0305093B1 (fr)
JP (1)	JPS6468375A (fr)
KR (1)	KR890003764A (fr)
CN (2)	CN1031532A (fr)
AP (1)	AP89A (fr)
AT (1)	ATE103919T1 (fr)
AU (1)	AU613392B2 (fr)
CA (1)	CA1336432C (fr)
DD (1)	DD289529A5 (fr)
DE (1)	DE3888897T2 (fr)
DK (1)	DK168954B1 (fr)
ES (1)	ES2063039T3 (fr)
FI (1)	FI89600C (fr)
GB (1)	GB8719368D0 (fr)
HU (1)	HU204052B (fr)
IL (1)	IL87435A (fr)
MC (1)	MC1969A1 (fr)
MX (1)	MX12655A (fr)
MY (1)	MY103602A (fr)
NO (1)	NO168305C (fr)
NZ (1)	NZ225808A (fr)
PH (1)	PH25741A (fr)
PL (3)	PL160044B1 (fr)
PT (1)	PT88260B (fr)
RU (3)	RU1769759C (fr)
YU (3)	YU47200B (fr)
ZA (1)	ZA885996B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8719368D0 (en) *	1987-08-15	1987-09-23	Wellcome Found	Heterocyclic compounds
PH27291A (en) *	1989-01-31	1993-05-04	Takeda Chemical Industries Ltd	Imidazolpyrimidazines their production and use
EP0440119A1 (fr) *	1990-01-31	1991-08-07	Takeda Chemical Industries, Ltd.	Composés de imidazopyridazine, leur préparation et utilisation
EP0444549B1 (fr) *	1990-03-01	1995-01-25	Takeda Chemical Industries, Ltd.	Imidazopyridazines, leur préparation et leur application
WO2000023450A1 (fr) *	1998-10-21	2000-04-27	Takeda Chemical Industries, Ltd.	Derives fusionnes de pyridazine, procede de preparation correspondant et utilisation de ces derives
CA2413802A1 (fr) *	2000-06-30	2002-01-10	Mark R. Schmitt	Triazolopyrimidines substitues comme agents anticancereux
JP3767352B2 (ja)	2000-09-18	2006-04-19	トヨタ自動車株式会社	内燃機関の制御装置
US6960584B2 (en) *	2001-04-10	2005-11-01	Merck & Co., Inc.	Inhibitors of Akt activity
JP5238697B2 (ja) *	2006-08-04	2013-07-17	武田薬品工業株式会社	縮合複素環誘導体およびその用途
WO2008058126A2 (fr) *	2006-11-06	2008-05-15	Supergen, Inc.	Dérivés d'imidazo[1,2-b]pyridazine et de pyrazolo[1,5-a]pyrimidine et utilisation de ceux-ci comme inhibiteurs de protéines kinases
BRPI0815503A2 (pt) *	2007-08-17	2014-09-30	Icagen Inc	Composto, composição farmacêutica, e, métodos para modular a atividade de um canal de íon potássio em um indivíduo, para aumentar o fluxo de íon por meio de canais de potássio dependentes da voltagem em uma célula e para tratar, prevenir, inibir ou aliviar um distúrbio ou condição do sistema nervoso central ou periférico
US8431608B2 (en)	2007-08-17	2013-04-30	Icagen Inc.	Heterocycles as potassium channel modulators
UY31676A1 (es) *	2008-02-28	2009-09-30		"derivados de 3-metil-imidiazo-[1,2-b]-piridazina"
EP2444403A1 (fr) *	2008-04-18	2012-04-25	Shionogi Co., Ltd.	Composé hétérocyclique doté d'une activité inhibitrice sur PI3K
UY32049A (es) *	2008-08-14	2010-03-26	Takeda Pharmaceutical	Inhibidores de cmet
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1987
- 1987-08-15 GB GB878719368A patent/GB8719368D0/en active Pending
1988
- 1988-08-10 AP APAP/P/1988/000098A patent/AP89A/en active
- 1988-08-11 MC MC882000A patent/MC1969A1/fr unknown
- 1988-08-12 IL IL87435A patent/IL87435A/xx not_active IP Right Cessation
- 1988-08-12 MX MX1265588A patent/MX12655A/es unknown
- 1988-08-12 KR KR1019880010374A patent/KR890003764A/ko not_active Ceased
- 1988-08-12 NZ NZ225808A patent/NZ225808A/en unknown
- 1988-08-12 PH PH37401A patent/PH25741A/en unknown
- 1988-08-12 RU SU884356488A patent/RU1769759C/ru active
- 1988-08-12 DE DE3888897T patent/DE3888897T2/de not_active Expired - Fee Related
- 1988-08-12 ZA ZA885996A patent/ZA885996B/xx unknown
- 1988-08-12 AT AT88307513T patent/ATE103919T1/de not_active IP Right Cessation
- 1988-08-12 ES ES88307513T patent/ES2063039T3/es not_active Expired - Lifetime
- 1988-08-12 HU HU884333A patent/HU204052B/hu not_active IP Right Cessation
- 1988-08-12 DK DK451588A patent/DK168954B1/da not_active IP Right Cessation
- 1988-08-12 AU AU20979/88A patent/AU613392B2/en not_active Ceased
- 1988-08-12 DD DD88318868A patent/DD289529A5/de not_active IP Right Cessation
- 1988-08-12 PT PT88260A patent/PT88260B/pt not_active IP Right Cessation
- 1988-08-12 CA CA000574614A patent/CA1336432C/fr not_active Expired - Fee Related
- 1988-08-12 CN CN88106693A patent/CN1031532A/zh active Pending
- 1988-08-12 NO NO883613A patent/NO168305C/no unknown
- 1988-08-12 JP JP63200321A patent/JPS6468375A/ja active Pending
- 1988-08-12 MY MYPI88000935A patent/MY103602A/en unknown
- 1988-08-12 YU YU156988A patent/YU47200B/sh unknown
- 1988-08-12 PL PL1988290245A patent/PL160044B1/pl unknown
- 1988-08-12 PL PL1988274216A patent/PL159008B1/pl unknown
- 1988-08-12 FI FI883758A patent/FI89600C/fi not_active IP Right Cessation
- 1988-08-12 US US07/231,894 patent/US5091531A/en not_active Expired - Fee Related
- 1988-08-12 PL PL1988290246A patent/PL160045B1/pl unknown
- 1988-08-12 EP EP88307513A patent/EP0305093B1/fr not_active Expired - Lifetime
1989
- 1989-06-19 RU SU894614566A patent/RU2017741C1/ru active
- 1989-07-25 RU SU894614684A patent/RU1836372C/ru active
- 1989-10-18 YU YU202889A patent/YU47212B/sh unknown
- 1989-10-18 YU YU202789A patent/YU47130B/sh unknown
1993
- 1993-03-31 CN CN93103896A patent/CN1085901A/zh active Pending
- 1993-09-17 US US08/122,699 patent/US5371219A/en not_active Expired - Fee Related
- 1993-09-17 US US08/123,529 patent/US5380759A/en not_active Expired - Fee Related
1994
- 1994-07-08 US US08/272,009 patent/US5447956A/en not_active Expired - Fee Related
1995
- 1995-06-02 US US08/458,225 patent/US5538970A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5380759A (en)	1995-01-10
MC1969A1 (fr)	1989-09-29
CN1085901A (zh)	1994-04-27
AP89A (en)	1990-06-14
HUT50473A (en)	1990-02-28
FI883758A0 (fi)	1988-08-12
YU202789A (en)	1990-04-30
PH25741A (en)	1991-10-18
PL274216A1 (en)	1989-05-02
YU47212B (sh)	1995-01-31
NO168305B (no)	1991-10-28
FI89600B (fi)	1993-07-15
CN1031532A (zh)	1989-03-08
YU202889A (en)	1990-04-30
MX12655A (es)	1993-10-01
YU47130B (sh)	1994-12-28
NO168305C (no)	1992-02-05
DK168954B1 (da)	1994-07-18
FI89600C (fi)	1993-10-25
JPS6468375A (en)	1989-03-14
ATE103919T1 (de)	1994-04-15
US5447956A (en)	1995-09-05
RU1769759C (ru)	1992-10-15
IL87435A0 (en)	1989-01-31
AU2097988A (en)	1989-02-16
AU613392B2 (en)	1991-08-01
US5538970A (en)	1996-07-23
PT88260A (pt)	1989-09-14
AP8800098A0 (en)	1988-08-01
ES2063039T3 (es)	1995-01-01
FI883758A7 (fi)	1989-02-16
NO883613D0 (no)	1988-08-12
DK451588D0 (da)	1988-08-12
PL159008B1 (pl)	1992-11-30
IL87435A (en)	1993-01-31
KR890003764A (ko)	1989-04-17
EP0305093B1 (fr)	1994-04-06
US5091531A (en)	1992-02-25
HU204052B (en)	1991-11-28
YU156988A (en)	1990-04-30
US5371219A (en)	1994-12-06
EP0305093A1 (fr)	1989-03-01
MY103602A (en)	1993-08-28
PL160044B1 (pl)	1993-02-26
NO883613L (no)	1989-02-16
PL160045B1 (en)	1993-02-26
YU47200B (sh)	1995-01-31
NZ225808A (en)	1991-07-26
PT88260B (pt)	1995-03-01
RU2017741C1 (ru)	1994-08-15
ZA885996B (en)	1990-04-25
DE3888897T2 (de)	1994-10-20
RU1836372C (ru)	1993-08-23
GB8719368D0 (en)	1987-09-23
DK451588A (da)	1989-02-16
CA1336432C (fr)	1995-07-25
DE3888897D1 (de)	1994-05-11

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1999-07-08	ENJ	Ceased due to non-payment of renewal fee

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EP0682027B1 (fr)	1997-10-15	Dérivés de la pyrrolopyrimidine avec une activité anti-proliférative
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DE69804743T2 (de)	2002-08-08	Pyrazolo[4,3-d]pyrimidin-Derivate und diese enthaltende pharmazeutische Zubereitungen
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EP0180833A1 (fr)	1986-05-14	Dérivés de la 4-oxopyrido[2,3-d]pyrimidine, procédé pour leur préparation et médicaments les contenant
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DE2240043A1 (de)	1973-03-01	(phenyl-tolyl)-1,2,4-triazole und verfahren zu ihrer herstellung