CH648312A5 - 6-hydrazono-pyrido(2,1-b)chinazolin-11-on-derivate und verfahren zuderen herstellung. - Google Patents

6-hydrazono-pyrido(2,1-b)chinazolin-11-on-derivate und verfahren zuderen herstellung. Download PDF

Info

Publication number: CH648312A5
Authority: CH; Switzerland
Prior art keywords: general formula; compounds; pyrido; same; meaning
Prior art date: 1980-06-24

Application number

CH4143/81A

Other languages

German (de)

English (en)

Inventor

Istvan Hermecz

Jozsef Koekoesi

Agnes Horvath

Zoltan Meszaros

Gyoergy Szasz

Tibor Breining

Lelle-Debreczy Vasvari

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1980-06-24

Filing date

1981-06-23

Publication date

1985-03-15

1981-06-23 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1985-03-15 Publication of CH648312A5 publication Critical patent/CH648312A5/de

Links

238000000034 method Methods 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 60
-1 nitro, carboxyl Chemical group 0.000 claims description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
239000012954 diazonium Substances 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
150000001989 diazonium salts Chemical class 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 4
NFSBKHUHALQOAO-UHFFFAOYSA-N 1h-pyrido[2,1-b]quinazoline Chemical compound C1=CC=CN2C=C3CC=CC=C3N=C21 NFSBKHUHALQOAO-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Chemical group 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
OKXPYKHKJCATPX-UHFFFAOYSA-N quinazoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=NC=C21 OKXPYKHKJCATPX-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
150000002429 hydrazines Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
RMZDXTBIBYDFHR-UHFFFAOYSA-N 2h-quinazoline-3-carboxylic acid Chemical compound C1=CC=CC2=CN(C(=O)O)CN=C21 RMZDXTBIBYDFHR-UHFFFAOYSA-N 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000002585 base Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
239000001632 sodium acetate Substances 0.000 description 7
235000017281 sodium acetate Nutrition 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000155 melt Substances 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
ACVGWSKVRYFWRP-UHFFFAOYSA-N Rutecarpine Chemical compound C1=CC=C2C(=O)N(CCC=3C4=CC=CC=C4NC=33)C3=NC2=C1 ACVGWSKVRYFWRP-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 2
150000003246 quinazolines Chemical class 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
UIBPFAMKRHUUTO-UHFFFAOYSA-N 11-oxo-6,7,8,9-tetrahydropyrido[2,1-b]quinazoline-6-carbaldehyde Chemical compound C1=CC=C2C(=O)N3CCCC(C=O)C3=NC2=C1 UIBPFAMKRHUUTO-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
JPHQWUWVHZOOBW-UHFFFAOYSA-N 9-methyl-6-(phenylhydrazinylidene)-8,9-dihydro-7h-pyrido[2,1-b]quinazolin-11-one Chemical compound C12=NC3=CC=CC=C3C(=O)N2C(C)CCC1=NNC1=CC=CC=C1 JPHQWUWVHZOOBW-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical class C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000003790 chinazolinyl group Chemical group 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- G—PHYSICS
- G16—INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR SPECIFIC APPLICATION FIELDS
- G16H—HEALTHCARE INFORMATICS, i.e. INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR THE HANDLING OR PROCESSING OF MEDICAL OR HEALTHCARE DATA
- G16H10/00—ICT specially adapted for the handling or processing of patient-related medical or healthcare data
- G16H10/60—ICT specially adapted for the handling or processing of patient-related medical or healthcare data for patient-specific data, e.g. for electronic patient records
- G—PHYSICS
- G16—INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR SPECIFIC APPLICATION FIELDS
- G16H—HEALTHCARE INFORMATICS, i.e. INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR THE HANDLING OR PROCESSING OF MEDICAL OR HEALTHCARE DATA
- G16H40/00—ICT specially adapted for the management or administration of healthcare resources or facilities; ICT specially adapted for the management or operation of medical equipment or devices
- G16H40/60—ICT specially adapted for the management or administration of healthcare resources or facilities; ICT specially adapted for the management or operation of medical equipment or devices for the operation of medical equipment or devices
- G16H40/67—ICT specially adapted for the management or administration of healthcare resources or facilities; ICT specially adapted for the management or operation of medical equipment or devices for the operation of medical equipment or devices for remote operation
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A90/00—Technologies having an indirect contribution to adaptation to climate change
- Y02A90/10—Information and communication technologies [ICT] supporting adaptation to climate change, e.g. for weather forecasting or climate simulation

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Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Primary Health Care (AREA)
Medical Informatics (AREA)
Epidemiology (AREA)
Biomedical Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Business, Economics & Management (AREA)
General Business, Economics & Management (AREA)
Hematology (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH4143/81A 1980-06-24 1981-06-23 6-hydrazono-pyrido(2,1-b)chinazolin-11-on-derivate und verfahren zuderen herstellung. CH648312A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU801559A HU183173B (en)	1980-06-24	1980-06-24	Process for producing 6-hydrazono-pyrido-aracket-2,1-b-bracket closed-quinazolin-11-ones

Publications (1)

Publication Number	Publication Date
CH648312A5 true CH648312A5 (de)	1985-03-15

Family

ID=10955013

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4143/81A CH648312A5 (de)	1980-06-24	1981-06-23	6-hydrazono-pyrido(2,1-b)chinazolin-11-on-derivate und verfahren zuderen herstellung.

Country Status (25)

Country	Link
JP (1)	JPS5738781A (hu)
AT (1)	AT379393B (hu)
AU (1)	AU544360B2 (hu)
BE (1)	BE889339A (hu)
CA (1)	CA1167842A (hu)
CH (1)	CH648312A5 (hu)
CS (1)	CS296285A2 (hu)
DD (1)	DD160060A5 (hu)
DE (1)	DE3124577A1 (hu)
DK (1)	DK277281A (hu)
ES (1)	ES8203370A1 (hu)
FI (1)	FI70897C (hu)
FR (1)	FR2485534A1 (hu)
GB (1)	GB2080291B (hu)
GR (1)	GR74608B (hu)
HU (1)	HU183173B (hu)
IL (1)	IL63061A (hu)
IT (1)	IT1144814B (hu)
NL (1)	NL8102935A (hu)
NO (1)	NO157142C (hu)
PL (2)	PL129635B1 (hu)
PT (1)	PT73248B (hu)
SE (1)	SE441829B (hu)
SU (2)	SU1192614A3 (hu)
YU (1)	YU42722B (hu)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ194196A (en) *	1979-07-17	1983-07-15	Ici Australia Ltd	-(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors
AT377586B (de) *	1981-06-30	1985-04-10	Erba Farmitalia	Verfahren zur herstellung von substituierten pyrrolo-(2,1-b)-chinazolinen und pyrido(2,1-b)chinazolinen
JPS5987269A (ja) *	1982-11-12	1984-05-19	Nissan Motor Co Ltd	燃料噴射弁
JPS61126367A (ja) *	1984-11-24	1986-06-13	Mitsubishi Heavy Ind Ltd	燃料噴射装置
JPS61129457A (ja) *	1984-11-27	1986-06-17	Mitsubishi Heavy Ind Ltd	多燃料弁噴射装置

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178496B (en) *	1977-12-29	1982-05-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity

1980
- 1980-06-24 HU HU801559A patent/HU183173B/hu not_active IP Right Cessation
1981
- 1981-06-09 IL IL63061A patent/IL63061A/xx unknown
- 1981-06-18 NL NL8102935A patent/NL8102935A/nl not_active Application Discontinuation
- 1981-06-18 CS CS852962A patent/CS296285A2/cs unknown
- 1981-06-22 GR GR65305A patent/GR74608B/el unknown
- 1981-06-22 FR FR8112209A patent/FR2485534A1/fr active Granted
- 1981-06-22 ES ES503266A patent/ES8203370A1/es not_active Expired
- 1981-06-23 PT PT73248A patent/PT73248B/pt unknown
- 1981-06-23 AT AT0277081A patent/AT379393B/de not_active IP Right Cessation
- 1981-06-23 PL PL1981235214A patent/PL129635B1/pl unknown
- 1981-06-23 PL PL1981231826A patent/PL129623B1/pl unknown
- 1981-06-23 SU SU813301195A patent/SU1192614A3/ru active
- 1981-06-23 SE SE8103940A patent/SE441829B/sv not_active IP Right Cessation
- 1981-06-23 DE DE19813124577 patent/DE3124577A1/de not_active Withdrawn
- 1981-06-23 YU YU1564/81A patent/YU42722B/xx unknown
- 1981-06-23 DK DK277281A patent/DK277281A/da not_active Application Discontinuation
- 1981-06-23 AU AU72081/81A patent/AU544360B2/en not_active Ceased
- 1981-06-23 GB GB8119298A patent/GB2080291B/en not_active Expired
- 1981-06-23 BE BE0/205178A patent/BE889339A/fr not_active IP Right Cessation
- 1981-06-23 IT IT67869/81A patent/IT1144814B/it active
- 1981-06-23 NO NO812143A patent/NO157142C/no unknown
- 1981-06-23 CA CA000380416A patent/CA1167842A/en not_active Expired
- 1981-06-23 CH CH4143/81A patent/CH648312A5/de not_active IP Right Cessation
- 1981-06-23 FI FI811970A patent/FI70897C/fi not_active IP Right Cessation
- 1981-06-24 JP JP9813381A patent/JPS5738781A/ja active Pending
- 1981-06-26 DD DD81231194A patent/DD160060A5/de not_active IP Right Cessation
1982
- 1982-05-18 SU SU823436303A patent/SU1191449A1/ru active

Also Published As

Publication number	Publication date
FI70897B (fi)	1986-07-18
SE8103940L (sv)	1981-12-25
PL235214A1 (hu)	1982-10-25
GB2080291A (en)	1982-02-03
IL63061A (en)	1985-04-30
FR2485534B1 (hu)	1985-01-11
PL129635B1 (en)	1984-05-31
PL129623B1 (en)	1984-05-31
IL63061A0 (en)	1981-09-13
IT8167869A0 (it)	1981-06-23
ES503266A0 (es)	1982-04-01
PL231826A1 (hu)	1982-07-05
FR2485534A1 (fr)	1981-12-31
SU1192614A3 (ru)	1985-11-15
JPS5738781A (en)	1982-03-03
AU544360B2 (en)	1985-05-23
GR74608B (hu)	1984-06-29
DK277281A (da)	1981-12-25
YU156481A (en)	1983-09-30
IT1144814B (it)	1986-10-29
FI811970L (fi)	1981-12-25
GB2080291B (en)	1984-01-18
AU7208181A (en)	1982-01-07
DE3124577A1 (de)	1982-09-23
CA1167842A (en)	1984-05-22
SU1191449A1 (ru)	1985-11-15
AT379393B (de)	1985-12-27
PT73248A (en)	1981-07-01
NO157142C (no)	1988-01-27
HU183173B (en)	1984-04-28
PT73248B (en)	1982-07-22
ES8203370A1 (es)	1982-04-01
NO812143L (no)	1981-12-28
YU42722B (en)	1988-12-31
NO157142B (no)	1987-10-19
DD160060A5 (de)	1983-04-27
ATA277081A (de)	1985-05-15
SE441829B (sv)	1985-11-11
CS296285A2 (en)	1991-01-15
FI70897C (fi)	1986-10-27
BE889339A (fr)	1981-10-16
NL8102935A (nl)	1982-01-18

Publication	Publication Date	Title
DE69530989T2 (de)	2004-05-19	Neue pyrimidinderivate und verfahren zu ihrer herstellung
DE69605746T2 (de)	2000-04-27	Naphtholderivate und ein verfahren zu ihrer herstellung
CH635586A5 (de)	1983-04-15	Verfahren zur herstellung von 1,3-dihydroimidazo(4,5-b)pyridin-2-onen.
EP0386628B1 (de)	1993-06-23	Verfahren zur Herstellung von Indolcarbonsäurederivaten
DD251971A5 (de)	1987-12-02	Verfahren zur herstellung einer pharmazeutisch aktiven oxindol-verbindung
DE2809720C2 (hu)	1992-01-16
DE1670523A1 (de)	1970-12-03	Verfahren zur Herstellung neuer substituierter Aminopyridine
DE1132560B (de)	1962-07-05	Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten
CH648312A5 (de)	1985-03-15	6-hydrazono-pyrido(2,1-b)chinazolin-11-on-derivate und verfahren zuderen herstellung.
DE3605743A1 (de)	1987-08-27	1,6-naphthyridin-derivate, verfahren zu deren herstellung und deren verwendung
DD261598A5 (de)	1988-11-02	Verfahren zur herstellung von chinazolin-dionen und pyrido-pyrimidin-dionen
DE1246722B (de)	1967-08-10	Verfahren zur Herstellung von Harnstoffderivaten
DE2649855C2 (de)	1987-01-22	Substituierte 5-Acetyl-4-hydroxy-3-phenylamino-2H-pyran-2,6(3H)-dione, Verfahren zu deren Herstellung und deren Verwendung
CH433352A (de)	1967-04-15	Verfahren zur Herstellung neuer 4-Oxo-1,2,3,4-tetrahydrochinazoline, deren Säureadditionssalzen und ihre Verwendung zur Herstellung von quaternären Ammoniumverbindungen
DE3129718A1 (de)	1982-04-15	4-oximino-1,2,3,4-tetrahydrochinolinderivate und verfahren zu ihrer herstellung
DE3311753A1 (de)	1984-10-04	Substituierte 6-aryl-1,2,4-triazolo(4,3-b)pyridazine - ihre herstellung und verwendung -
EP0189898A1 (de)	1986-08-06	1,6-Naphthyridinon-Derivate und Verfahren zu deren Herstellung
CH630350A5 (en)	1982-06-15	Process for the preparation of aromatically substituted sulphamoylbenzoic acid derivatives.
AT339294B (de)	1977-10-10	Verfahren zur herstellung von 4-(5- oder 7-)-benzoylindolin-2-onen
DE2436032A1 (de)	1976-02-05	Neue aromatische o-hydroxyaldehyde, verfahren zu ihrer herstellung und ihre verwendung
CH612186A5 (en)	1979-07-13	Process for the preparation of 2(1H)-quinazolinone derivatives
DE2314242A1 (de)	1974-09-26	Neue 3-substituierte 2-oxo-4-hydroxy1,2,3,4-tetrahydrochinazolin-4-carbonsaeurehydrazide
DE2650780A1 (de)	1977-05-18	Pyrazolo eckige klammer auf 1,5-a eckige klammer zu pyrido eckige klammer auf 3,2-e eckige klammer zu pyrimidin-7-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH438308A (de)	1967-06-30	Verfahren zur Herstellung neuer Isochinolinverbindungen
AT230371B (de)	1963-12-10	Verfahren zur Herstellung neuer Indolderivate

Legal Events

Date	Code	Title	Description
1991-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased